CN108264486A - A kind of novel glyoxaline compound and its preparation and electroluminescent device - Google Patents
A kind of novel glyoxaline compound and its preparation and electroluminescent device Download PDFInfo
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
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- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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Abstract
The present invention provides a kind of new imdazole derivatives, anthracene structure are introduced in imidazolium compounds, by connecting R1、R2And R3Group improves the three-dimensional performance of compound, and the advantages that by adjusting molecular weight and ligand species that can improve performance, the device prepared using the new imdazole derivatives of the present invention has the features such as high brightness, outstanding heat resistance, long-life and high efficiency.
Description
Technical field
The present invention relates to organic electroluminescent compounds and include its organic electroluminescence device.Specifically, it is related to
And novel glyoxaline compound is as electroluminescent material, and uses them as an organic electroluminescence device.
Background technology
General organic luminescent device (OLED) is the organic matter layer structure by being inserted between cathode, anode and cathode and anode
Into, the composition of device is transparent ITO anode, hole injection layer(TIL), hole transmission layer(HTL), luminescent layer(EL, hole resistance
Barrier(HBL), electron transfer layer(ETL), electron injecting layer(EIL), the cathodes such as LiAl formed, it is organic that 1 ~ 2 can be omitted on demand
Layer.Voltage is formed between two electrodes of device on one side from cathode electronics injection another side anode injection hole.Electrons and holes
In luminescent layer in conjunction with excitation state is formed, when excitation state returns to stable ground state, the fluorescent molecular of luminescent layer shines.
Luminescent material is divided into fluorescent material and phosphor material, and the forming method of luminescent layer is that phosphorus is adulterated in fluorescent host material
Luminescent material(Organic metal)Method and fluorescent host material doping fluorescent(Organic matter comprising nitrogen)The method and hair of dopant
Dopant is utilized in body of light(DCM, Rubrene, DCJTB etc.)The method of the existing long wavelength of tool, improvement of mixing in this way shine
The factors such as wavelength, efficiency, driving voltage, service life.Generally form emitting layer material be with benzene, naphthalene, fluorenes, two fluorenes of spiral shell, anthracene, pyrene,
The ligands such as the centerbodies such as carbazole and benzene, biphenyl, naphthalene, heterocycle;Contraposition, meta position, the binding site at ortho position and cyano, fluorine, methyl, uncle
The replacing structures such as butyl.
Present oled panel develops to enlargement, the finer and smoother and distincter material of color is needed, wherein the emphasis solved
Blue material, especially need it is light blue move on to navy blue high performance material, the chromaticity coordinates of another aspect emission wavelength with
And low driving voltage, high efficiency light-emitting efficiency and the good high glass transition temperature material of thermal stability.
Heteroaromatic compound such as oxadiazole, thiadiazole, pyrimidine etc. may be used as being formed the material of electron transfer layer, be used for
The material of electron transfer layer need to have preferable thermal stability, higher electron mobility, the high efficiency of illuminator and long-life,
It is more more superior than same type of material performance at this stage that the present invention provides new imdazole derivatives.
Invention content
The present invention provides a kind of new imdazole derivatives, anthracene structure are introduced in imidazolium compounds, by connecting Ar1Base
Group improves the three-dimensional performance of compound, in addition adjustment ligand R1And R2The advantages that molecular weight and ligand species can improve performance.
Technical scheme is as follows, and the general structure of the new imdazole derivatives is shows shown in chemical formula 1:
[chemical formula 1]
R1、R2And R3It represents identical or differs group, substituted or non-substituted C6~C60Aryl, substituted or non-substituted C5~C60
Heterocycle, substituted or non-substituted C6~C60Aryl amine;The substituted group is hydrogen, halogen, C1~C60Alkyl, C1~C60
Alkoxy, C1~C60Alkylamino radical, C6~C60Aryl amine, C1~C60Alkane sulfydryl, C6~C60Aromatic thiohydroxy, C2~C60Alkylene,
C2~C60Alkynes base, C3~C60Cycloalkyl, C6~C60Aryl, C8~C60Arylalkenyl, silicon substrate and C5~C60Heterocycle.
Preferably, R1、R2And R3It can be identical or differ group, any one composition is special in following chemical formula
Fixed new glyoxaline compound:
Wherein X and Y can as or different group, hydrogen atom, halogen, cyano, C1~C30Alkyl, C1~C30Alcoxyl
Base, the alkenyl of carbon atom number 2 ~ 30, the aralkyl of carbon atom number 7 ~ 30, the aralkoxy of carbon atom number 7 ~ 30, carbon atom number 6 ~
30 aryl, the aryloxy group of carbon atom number 6 ~ 30, the heterocycle of carbon atom number 5 ~ 30, carbon atom number 6 ~ 30 aromatic amine.
Preferably, the R1、R2And R3It is independent selected from phenyl, 1- naphthalenes, 1- naphthalenes, pyrenyl, pyridyl group, triarylamine,
Carbazyl, xenyl, quinolyl, substituted carbazyl;The substituent group is selected from phenyl.
Preferably, the compound has the structure shown in following 001 ~ 017:
001,002,
003,004,
005,006,
007,008,
009,010,
011,012,
013,014,
015,016,017。
Present invention also provides a kind of preparation method of the compound described in said program, including:
By formula(A)The compound and formula of structure(B)The compound of structure generates the new imidazoles of chemical formula 1 by coupling reaction
Derivative;
(A),(B),(1),
X is Cl, Br, I;
Wherein, formula(A)Compound be by formula(C)It is obtained by NBS bromo-reactions;
(C),(A), X Cl, Br, I;
Wherein, formula(C)Compound be by formula(E)And formula(F)Cyclization is obtained by the reaction;
(E),(F),(C);
Wherein, R1、R2And R3It is to represent identical or differ group, substituted or non-substituted C1 ~ C60 alkyl is substituted or non-substituted
C6 ~ C60 aryl, substituted or non-substituted C5 ~ C60 heterocycles, substituted or non-substituted C7 ~ C60 condensed ring radicals substitution or non-take
The aryl amine of the C6 ~ C60 in generation;The substituted group includes hydrogen, halogen, the alkyl of C1 ~ C60, C1 ~ C60 alkoxies, C1 ~ C60
Alkylamino radical, the aryl amine of C6 ~ C60, the alkane sulfydryl of C1 ~ C60, the aromatic thiohydroxy of C6 ~ C60, the alkylene of C2 ~ C60, C2 ~ C60
Alkynes base, the cycloalkyl of C3 ~ C60, the aryl of C6 ~ C60, the arylalkenyl of C8 ~ C60, silicon substrate and C5 ~ C60 any one of heterocycle.
Prepared by the preparation method present invention also provides the compound described in a kind of said program or described in said program
Application of the compound as luminescent material in organic electroluminescence device is prepared.
The present invention provides a kind of new imdazole derivatives, anthracene structure are introduced in imidazolium compounds, by improving chemical combination
The three-dimensional performance of object adjusts ligand R1 and R2, R3 molecular weight and the advantages that ligand species can improve performance, uses that the present invention's is new
Imdazole derivatives prepare device have the features such as long-life and high efficiency.
Still further aspect of the present invention is to provide the manufactured Organic Electricity of the new imidazole derivative including chemical formula 1 above
Electroluminescence device.Including first electrode, second electrode and the one or more organic compound layers being placed between two electrode,
It is characterized in that, at least one organic compound layer includes at least one new glyoxaline compound of the present invention.
Above-mentioned new imdazole derivatives are single form or include in above-mentioned organic layer with other material mixing forms.
Above-mentioned organic matter layer wherein at least includes hole injection layer, hole transmission layer, had both had hole injection but also with sky
Technical ability layer is transmitted in cave, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer and both has electronics biography
Defeated any one layer but also in electron injecting layer.
Above-mentioned hole injection layer, above-mentioned hole transmission layer, it is above-mentioned both had hole injection but also with hole transport technical ability layer
In it is at least one be conventional hole injecting material, hole transporting material and both have hole injection but also with hole transport technical ability
Substance, it is also possible to be the substance of electron-transporting material generation.
" organic matter layer " refers to the whole disposed between organic electronic device first electrode and second electrode in this patent
The term of layer.
For example, above-mentioned organic layer includes luminescent layer, above-mentioned organic layer includes phosphorescence host, fluorescent host, phosphorescence doping
And more than one in fluorescence doping, including aromatic amine derivative in above-mentioned luminescent layer, i) above-mentioned fluorescent host can be
Aromatic amine derivative;Ii) above-mentioned fluorescence doping can be aromatic amine derivative;iii)Above-mentioned fluorescent host and fluorescence doping
It can be aromatic amine derivative.
Above-mentioned luminescent layer is can also red, yellow or cyan luminescent layer.For example, aromatic amine during above-mentioned luminescent layer cyan
Derivative use adulterates purposes in cyan main body or cyan, provides organic hair of high efficiency, high brightness, high-resolution and long-life
Optical device.
And above-mentioned organic layer includes electron transfer layer, and above-mentioned electron transfer layer includes above-mentioned new imdazole derivatives.
Wherein above-mentioned electron transfer layer is to include the compound containing metal other than above-mentioned new imdazole derivatives again.
Above-mentioned organic layer all includes luminescent layer and electron transfer layer, and above-mentioned luminescent layer and electron transfer layer respectively include above-mentioned
Imdazole derivatives(Above-mentioned luminescent layer and electron transfer layer include above-mentioned new imdazole derivatives can also it is identical can not also
Together).
Above-mentioned organic electronic device is had using the new imdazole derivatives and conventional material and preparation of chemical formula 1
It is prepared by the method for machine electronic device.
Another aspect of the present invention is that above-mentioned device can be used in organic luminescent device(OLED), organic photovoltaic cell
(OSC), Electronic Paper(e-Paper), Organophotoreceptor(OPC)Or Organic Thin Film Transistors(OTFT).Organic luminescent device is profit
With evaporation metal and conductive oxide on substrate the methods of film vapor deposition, electron beam evaporation, physical vapour deposition (PVD) and
Their alloy forms anode, and layer, luminescent layer, hole blocking layer and electron transfer layer are conveyed in above-mentioned hole injection layer, hole
It is prepared by the method for its later above-mentioned evaporation cathode.Cathode substance starts organic matter layer, anode material on substrate other than above method
Vapor deposition makes organic luminescent device in order.
Above-mentioned organic matter layer is can also to include hole injection layer, hole reception and registration layer, luminescent layer, hole blocking layer and electronics
The multilayered structure of transport layer, and above-mentioned organic matter layer is to substitute evaporation coating method using various high molecular material solvent engineering,
For example, spin-coating(spin-coating), strip molding(tape-casting), scraping blade method(doctor-blading), silk
Wire mark brush(Screen-Printing), ink jet printing or number of plies manufacture is reduced the methods of thermal imaging (Thermal-Imaging).
Organic assembly according to the present invention be by the material used can also front shine, back side illuminated or lighting at two sides.
The compound of the present invention is organic photovoltaic cell, illumination OLED, flexibility OLED, Organophotoreceptor, organic crystal
Organic luminescent device can also be applied in the organic assemblies such as pipe and be applicable in similar principle.
Specific embodiment:
It is clearly and completely described below in conjunction with the technical solution of the embodiment of the present invention, it is clear that described embodiment is only
Only it is part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, ordinary skill
Personnel's all other embodiments obtained without making creative work, shall fall within the protection scope of the present invention.
The synthesis of 1 intermediate M1 of embodiment
9- anthraldehydes(10.0g 48.5mmol)With adjacent aminodiphenylamine(8.9g, 48.5mmol)It is placed in dry DMF(100ml)
In, add in sodium pyrosulfite(11.0g 58.2mmol), 155 DEG C are reacted 18h, after reaction, are cooled to room temperature, and are washed, second
Acetoacetic ester extracts, dry, and solvent evaporated, re crystallization from toluene obtains intermediate M1(14.7g, y=82%).
Embodiment 2
According to preparation method synthetic intermediate M2 ~ M5 of above-mentioned intermediate M1, table 1 is 2 reactive material of the embodiment of the present invention, generation
Substance and yield summarize.
Table 1 is that 2 reactive material of the embodiment of the present invention, generation substance and yield summarize
Embodiment 3:The synthesis of intermediate N1
Intermediate M1(14.7g 39.6mmol)It is dissolved in dichloromethane(100ml), it is placed in ice-water bath, adds in NBS(7.0g
39.6mol)2h is reacted, after reaction, is washed, liquid separation, dry organic phase, solvent evaporated obtains solid bromo-derivative, layer of silica gel
Column separating purification is analysed, obtains intermediate N1(15.6g, y=88%).
Embodiment 4
According to preparation method synthetic intermediate N2 ~ N5 of above-mentioned intermediate N1, table 2 is 4 reactive material of the embodiment of the present invention, generation
Substance and yield summarize.
2 embodiment of the present invention of table, 4 reactive material, generation substance and yield summarize
Embodiment 5:The synthesis of compound 001
Intermediate N1 (15.6g, 34.7mmol), diphenylamines(6.4g, 38.1mmol), sodium tert-butoxide(6.6g, 69.4mol)It adds in
To toluene solution(150ml)In, nitrogen protection adds in catalyst(0.2g, 0.3mmol)With phosphorus ligand(0.1g, 0.6mmol),
It is warming up to back flow reaction 12 hours, after reaction, washing detaches organic phase, dry to concentrate, silica gel column chromatography column separating purification,
Obtain compound(13.4g,y=72%).Mass spectrum:537.24.
Embodiment 6
According to above compound 001 preparation method synthesize compound 002 ~ 017, table 3 be 6 reactive material of the embodiment of the present invention,
Generation substance and yield summarize.
3 embodiment of the present invention of table, 6 reactive material, generation substance and yield summarize
Embodiment 7
Glyoxaline compound 001 ~ 040 prepared by the embodiment of the present invention 5 ~ 6 is configured to a concentration of 1 × 10 respectively-6Mol/L's
Solution, using Edinburdh-FL S920 equipment, spin-coating method is fabricated to film, tests their luminous efficiency respectively, specifically
Data such as the following table 4.
The luminous efficiency of compound prepared by 4 embodiment 5 ~ 6 of table
The luminous effect of imidazole derivative that the embodiment of the present invention is prepared in weak solution is can be seen that from the data of table 4
Rate is 94.03%, and the luminous efficiency in film reaches 64.63%.The luminous efficiency of imidazole derivative i.e. provided by the invention compared with
Height disclosure satisfy that the requirement of OLED, it has been found that this kind of material is the electroluminescent organic material of function admirable, is before having very much
A kind of electroluminescent organic material of scape.
Embodiment 8
The present embodiment prepares blue phosphorescent organic electroluminescent device by the following method:Clean ITO (tin indium oxide) glass:Point
Ito glass is not cleaned with deionized water, acetone, EtOH Sonicate each 15 minutes, 2 points are then handled in plasma cleaner
Clock;The spin coating PEDOT on anode ito glass:For PSS as hole injection layer, rotating speed is 4000 revs/min, in air 200 DEG C
Annealing 5 minutes, then in nitrogen 200 DEG C anneal 15 minutes, thickness 28nm;In PEDOT:Vacuum evaporation is empty on PSS layer
Cave transport layer TCTA, rate 0.5nm/min, thickness 40nm.On hole transmission layer TCTA, co-evaporation luminescent layer MCP
And mass ratio shared by FIrpic, FIrpic is 8%, total liquid evaporation rate is 1.0nm/min, thickness 10nm;In luminescent layer
Vacuum evaporation electron transfer layer compound is using the compound C-1 ~ C-62 represented in preparation example, speed on MCP&FIrpic
0.5 nm/min thickness 40nm of rate;The vacuum evaporation LiF on electron transfer layer TPPB, rate thickness 0.5nm;On LiF
Vacuum evaporation cathode Al, thickness 120nm.The structure of device is ITO/PEDOT:PSS(28nm)/TCTA(40nm)/MCP:
FIrpic8% (10nm)/compound C-1 ~ C-62 (40nm)/LiF (0.5nm)/Al (120nm).Using the manufacture of DOV companies
EL evaporators carry out vacuum evaporation.It measures using 235 type source measuring unit of KEITHLEY Keithleys, SpectrascanPR650 light
Spectrum scanning colorimeter, to evaluate driving voltage, light emission luminance, luminous efficiency, luminescent color, the results are shown in Table 5:
The partial data of device is made in compound prepared by 5 embodiment 5 ~ 6 of table
It should be understood that the application of the present invention is not limited to the above, for those of ordinary skills, Ke Yigen
It is improved or converted according to above description, all these modifications and variations should all belong to the protection model of appended claims of the present invention
It encloses.
Claims (6)
1. a kind of new glyoxaline compound, which is characterized in that the new glyoxaline compound general molecular formula is:
[chemical formula 1]
R1、R2And R3It represents identical or differs group, substituted or non-substituted C6~C60Aryl, substituted or non-substituted C5~C60
Heterocycle, substituted or non-substituted C6~C60Aryl amine;The substituted group is hydrogen, halogen, C1~C60Alkyl, C1~C60
Alkoxy, C1~C60Alkylamino radical, C6~C60Aryl amine, C1~C60Alkane sulfydryl, C6~C60Aromatic thiohydroxy, C2~C60Alkylene,
C2~C60Alkynes base, C3~C60Cycloalkyl, C6~C60Aryl, C8~C60Arylalkenyl, silicon substrate and C5~C60Heterocycle.
A kind of 2. new glyoxaline compound according to claim 1, which is characterized in that R1、R2And R3Can be it is identical or
Group is differed, the specific new glyoxaline compound of any one composition in following chemical formula:
Wherein X and Y can as or different group, hydrogen atom, halogen, cyano, C1~C30Alkyl, C1~C30Alcoxyl
Base, the alkenyl of carbon atom number 2 ~ 30, the aralkyl of carbon atom number 7 ~ 30, the aralkoxy of carbon atom number 7 ~ 30, carbon atom number 6 ~
30 aryl, the aryloxy group of carbon atom number 6 ~ 30, the heterocycle of carbon atom number 5 ~ 30, carbon atom number 6 ~ 30 aromatic amine.
A kind of 3. new glyoxaline compound according to claim 1, which is characterized in that R1、R2And R3Independent is selected from
Hydrogen, methyl, phenyl, 1- naphthalenes, 1- naphthalenes, pyrenyl, pyridyl group, triarylamine, carbazyl, xenyl, quinolyl, substituted click
Oxazolyl;The substituent group is selected from phenyl.
4. a kind of new glyoxaline compound according to claim 1, which is characterized in that the compound has as follows
Structure shown in 001 ~ 017:
001,002,
003,004,
005,006,
007,008,
009,010,
011,012,
013,014,
015,016,017。
5. a kind of preparation method of compound described in claim 1, including:
By formula(A)The compound and formula of structure(B)The compound of structure generates the new imidazoles of chemical formula 1 by coupling reaction
Derivative;
(A),(B),(1),
X is Cl, Br, I;
Wherein, formula(A)Compound be by formula(C)It is obtained by NBS bromo-reactions;
(C),(A), X Cl, Br, I;
Wherein, formula(C)Compound be by formula(E)And formula(F)Cyclization is obtained by the reaction;
(E),(F),(C);
Wherein, R1、R2And R3It is to represent identical or differ group, substituted or non-substituted C1 ~ C60 alkyl is substituted or non-substituted
C6 ~ C60 aryl, substituted or non-substituted C5 ~ C60 heterocycles, substituted or non-substituted C7 ~ C60 condensed ring radicals substitution or non-take
The aryl amine of the C6 ~ C60 in generation;The substituted group includes hydrogen, halogen, the alkyl of C1 ~ C60, C1 ~ C60 alkoxies, C1 ~ C60
Alkylamino radical, the aryl amine of C6 ~ C60, the alkane sulfydryl of C1 ~ C60, the aromatic thiohydroxy of C6 ~ C60, the alkylene of C2 ~ C60, C2 ~ C60
Alkynes base, the cycloalkyl of C3 ~ C60, the aryl of C6 ~ C60, the arylalkenyl of C8 ~ C60, silicon substrate and C5 ~ C60 any one of heterocycle.
6. chemical combination prepared by the preparation method described in the compound or claim 5 described in a kind of claim 1 ~ 4 any one
Application of the object as luminescent material in organic electroluminescence device is prepared.
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