CN104650040B - A kind of organic electroluminescent compounds of azophenlyene analog derivative - Google Patents
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Abstract
The invention provides a kind of organic electroluminescent compounds of azophenlyene analog derivative, it is the compound with following structure Formulas I.The organic electroluminescent compounds of the present invention can be used for preparing organic electroluminescence device.
Description
Technical field
The present invention relates to field of organic electroluminescence, more particularly to a kind of organic electroluminescent of azophenlyene analog derivative
Compound.
Background technology
Organic electroluminescence device (OLEDs) is to pass through spin coating or vacuum evaporation deposition one between two metal electrodes
The device that layer organic material is prepared from, a classical three layer organic electroluminescence device comprises hole transmission layer, luminescent layer
And electron transfer layer.The hole being produced by anode through hole transmission layer with the electronics that produced by negative electrode through combined with electron transfer layer
Luminescent layer forms exciton, then lights.Organic electroluminescence device can be adjusted as desired by the material changing luminescent layer
Section launches the light of various needs.
Organic electroluminescence device, as a kind of new Display Technique, has self-luminous, wide viewing angle, low energy consumption, efficiency
High, thin, rich color, fast response time, Applicable temperature scope are wide, low driving voltage, can make flexible with transparent
The particular advantages such as display floater and environmental friendliness, can apply on flat faced display and a new generation's illumination it is also possible to conduct
The backlight of LCD.
Since inventing at the bottom of the eighties in 20th century, organic electroluminescence device has industrially been applied, such as
As screens such as camera and mobile phones, but current OLED is low due to efficiency, and it is wider that the factor such as service life is short restricts it
General application, particularly large screen display.And restricting one of key factor is exactly in organic electroluminescence device
The performance of electroluminescent organic material.Additionally, due to OLED when applied voltage is run, Joule heat can be produced so that
Organic material is susceptible to crystallize, and have impact on life-span and the efficiency of device, therefore it is also desirable to develop the organic electroluminescence of stability and high efficiency
Luminescent material.
In OLED material, because the speed of most electroluminescent organic material transporting holes is than the speed transmitting electronics
Hurry up, the electronics and the number of cavities that easily cause luminescent layer are uneven, and the efficiency of such device is just than relatively low.Three (8-hydroxyquinolines)
Aluminum (Alq3) since invention, be extensively studied, but as its electron mobility of electron transport material still very
Low, and the intrinsic characteristic that itself can degrade, with the device as electron transfer layer in it may appear that voltage situation about declining,
Simultaneously as relatively low electron mobility is so that substantial amounts of hole enters into Alq3In layer, excessive hole is with the shape of non-luminescent
Formula emittance, and when as electron transport material, due to the characteristic of its green light, application is restricted.Cause
This, development stability and there is the electron transport material of larger electron mobility, organic electroluminescence device is widely used
There is great value.
Content of the invention
Present invention firstly provides a kind of organic electroluminescent compounds of azophenlyene analog derivative, it is to have following structural formula
The compound of I：
Wherein, R1、R2、R3、R4、R5、R6、R7、R8、R10Separately be selected from hydrogen, D-atom, halogen, hydroxyl, cyano group,
Nitro, the substituted or unsubstituted alkyl or cycloalkyl of C1-C12, the alkoxyl of C1-C8, the replacement of C6-C30 or unsubstituted
Aryl, C3-C30 replace or unsubstituted heteroaryl, C2-C8 replace or unsubstituted thiazolinyl, C2-C8 replacement
Or unsubstituted alkynyl；
L is selected from sky, singly-bound, the substituted or unsubstituted alkyl of C1-C6, the substituted or unsubstituted aryl of C6-C30, C3-
The replacement of C30 or unsubstituted heteroaryl；
X1、X2Separately it is selected from CH, N；
Ar is replacement or unsubstituted aryl or the heteroaryl of C3-C60；
Wherein preferably mode is：
R1、R2、R3、R4、R5、R6、R7、R8、R10Separately be selected from hydrogen, halogen, cyano group, nitro, the alkyl of C1-C8,
The alkoxyl of C1-C8, phenyl, naphthyl, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinoline；
L is independently selected from sky, singly-bound, phenyl, the phenyl being replaced by C1-C4 alkyl, naphthyl, replaced by C1-C4 alkyl
Naphthyl, xenyl, the xenyl being replaced by C1-C4 alkyl；
Ar is dibenzothiophenes base, dibenzofuran group, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazines
Base, quinolyl, benzimidazolyl；
Wherein above-mentioned dibenzothiophenes base, dibenzofuran group, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical,
Three nitrogen piperazine bases, quinolyl, benzimidazolyl can be replaced by the aryl of the alkyl of C1-C4 or C6-C30 further；
Further preferred mode is：
R1、R2、R3、R4、R5、R6、R7、R8、R10Separately it is selected from hydrogen, fluorine, nitro, methyl, ethyl, propyl group, isopropyl
Base, the tert-butyl group, normal-butyl, n-hexyl, phenyl, naphthyl；
Ar is
Wherein Ar1And Ar2It independently is hydrogen, the substituted or unsubstituted alkyl of C1-C12, the replacement of C6-C60 or do not take
The aryl in generation, the replacement of C3-C60 or unsubstituted heteroaryl；
Wherein X3And X4Independently it is expressed as CH and N；
Wherein R11、R12、R13、R14Separately be selected from hydrogen, D-atom, halogen, cyano group, nitro,
The substituted or unsubstituted alkyl of C1-C12, the alkoxyl of C1-C8, the replacement of C6-C30 or unsubstituted virtue
Base, C3-C30 replace or unsubstituted heteroaryl, C2-C8 replace or unsubstituted thiazolinyl, the replacement of C2-C8 or
Unsubstituted alkynyl；
Wherein X5Selected from O, S, Se, NR15；
R15For hydrogen, the substituted or unsubstituted alkyl of C1-C12, the replacement of C6-C60 or unsubstituted aryl, C3-C60
Replacement or unsubstituted heteroaryl；
Further preferred mode is：
R11～R14Separately be selected from hydrogen, fluorine, nitro, methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl,
N-hexyl, phenyl, naphthyl；
Wherein X5For NR15；
R15、Ar1And Ar2Selected from hydrogen, methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, by C1-C8
The substituted or unsubstituted following aryl of alkyl or heteroaryl：
It is further preferred that the organic electroluminescent compounds of the azophenlyene analog derivative of the present invention are following structural 1-86
Compound：
The organic electroluminescent compounds of the azophenlyene analog derivative of the present invention can be prepared into by Suzuki coupling reaction
Arrive.
The organic electroluminescent compounds of the azophenlyene analog derivative of the present invention can be applied in organic electroluminescence device, has
Machine solaode, OTFT or organophotoreceptorswith field.
Present invention also offers a kind of organic electroluminescence device, this device comprises anode, negative electrode and organic layer, organic layer
Comprise in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer or electron transfer layer one layer or
More than one layer, at least one layer Organic Electricity containing the azophenlyene analog derivative as described in structural formula (I) in wherein said organic layer
Electro luminescent compounds：
Wherein R1-R10、Ar、L、X1-X2Defined as described above.
Wherein organic layer is luminescent layer and electron transfer layer；
Or organic layer is luminescent layer, hole transmission layer and electron transfer layer
Or organic layer is luminescent layer, hole injection layer, hole transmission layer and electron transfer layer；
Or organic layer is luminescent layer, hole injection layer, hole transmission layer, electron transfer layer and electron injecting layer；
Or organic layer is luminescent layer, hole injection layer, hole transmission layer, electron transfer layer, electron injecting layer and stop
Layer；
Or organic layer is luminescent layer, hole transmission layer, electron transfer layer, electron injecting layer and barrier layer；
Or organic layer is luminescent layer, hole transmission layer, electron injecting layer and barrier layer；
The layer that the organic electroluminescent compounds of the azophenlyene analog derivative wherein as described in structure formula (I) are located passes for electronics
Defeated layer or electron injecting layer；
The organic electroluminescent compounds of the azophenlyene analog derivative wherein described in structure formula (I) are the chemical combination of structural formula 1-86
Thing；
The organic electroluminescent compounds of the azophenlyene analog derivative as described in structure Formulas I can be used alone it is also possible to and
Other compounds are used in mixed way；The organic electroluminescent compounds of the azophenlyene analog derivative as described in structure Formulas I can individually make
With a kind of compound therein it is also possible to simultaneously using two or more the compound in structure Formulas I.
The organic electroluminescence device of the present invention, further preferred mode is that this organic electroluminescence device comprises sun
In pole, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, wherein electron transfer layer or electron injecting layer
Compound containing structure formula (I)；It is further preferred that the compound in electron transfer layer or electron injecting layer is structural formula
The compound of 1-86.
The organic electroluminescence device of the present invention, Compounds of structural formula I is as can also also serve as electronics during electron transfer layer
Implanted layer.
The gross thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
The organic electroluminescence device of the present invention when having the compound of structure Formulas I using the present invention, it is possible to use takes
Join other materials, such as hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and barrier layer etc., and
Obtain blue and green light, gold-tinted, HONGGUANG or white light.
The hole transmission layer of organic electroluminescence device of the present invention and hole injection layer, material requested has good hole
Transmission performance, can be transferred to hole luminescent layer from anode effectively.Other small molecules can be included and macromolecule is organic
Compound, including but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine
Class compound, the miscellaneous triphen (hexanitrilehexaazatriphenylene) of six cyano group six, the fluoro- 7,7' of 2,3,5,6- tetra-, 8,
8'- tetra- cyanogen dimethyl-parabenzoquinone (F4-TCNQ), Polyvinyl carbazole, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of the organic electroluminescence device of the present invention, has the good characteristics of luminescence, can adjust as needed
The scope of visible ray.Following compound, including but not limited to naphthalene compounds, pyrene compound, fluorenes class chemical combination can be contained
Thing, luxuriant and rich with fragrance class compound, bend class compound, glimmering anthracene compound, anthracene compound, Benzo[b class compound, class compound, two
Aromatic ethylene class compound, triphenylamine ethylene compounds, aminated compoundss, carbazole compound, benzimidazoles compound, furan
Class of muttering compound, metal organic fluorescence complex, metal Phosphorescent complex (such as Ir, Pt, Os, Cu, Au), polyethylene click
The organic polymer luminescent materials such as azoles, poly-organosilicon compound, polythiophene, they can be used alone it is also possible to multiple mixing
Thing uses.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires there is good electronic transmission performance, energy
Enough effectively electronics from cathode transport to luminescent layer in, there is very big electron mobility.Except the present invention, there is structure Formulas I
Chemical combination beyond the region of objective existence, can also select following compound, but not limited to this, oxa- oxazole, thiazole compound, triazole chemical combination
Thing, three nitrogen piperazine class compounds, triazine class compound, quinoline class compound, phenodiazine anthracene compound, siliceous heterocyclic chemical combination
Thing, quinolines, luxuriant and rich with fragrance quinoline class compound, metallo-chelate (as Alq3), fluorine substituted benzene compound, benzimidazole
Compound.
The electron injecting layer of organic electroluminescence device of the present invention, effectively can be injected into organic layer electronics from negative electrode
In, except the present invention there is Compounds of structural formula I in addition to, be mainly selected from alkali metal or alkali-metal compound, or be selected from alkaline earth
The compound of metal or alkaline-earth metal or alkali metal complex, can select following compound, but not limited to this, alkali gold
Genus, alkaline-earth metal, rare earth metal, alkali-metal oxide or halogenide, the oxide of alkaline-earth metal or halogenide, rare earth
The oxide of metal or the organic complex of halogenide, alkali metal or alkaline-earth metal；Be preferably lithium, lithium fluoride, lithium oxide,
Lithium nitride, 8-hydroxyquinoline lithium, caesium, cesium carbonate, 8-hydroxyquinoline caesium, calcium, calcium fluoride, calcium oxide, magnesium, Afluon (Asta), magnesium carbonate,
Magnesium oxide, these compounds can be used alone and can also mixture use it is also possible to join with other electroluminescent organic materials
Close and use.
Each layer of organic layer in the organic electroluminescence device of the present invention, can be steamed by vacuum vapour deposition, molecular beam
Prepared by the modes such as plating method, the dip coating being dissolved in solvent, spin-coating method, stick coating method or inkjet printing.Can make for metal motor
It is prepared with vapour deposition method or sputtering method.
Device experimental shows, the organic electroluminescent compounds of azophenlyene analog derivative as described in structure formula (I) for the present invention,
There is preferable heat stability, high-luminous-efficiency, high luminance purity.The organic electroluminescence being made using this organic electroluminescent compounds
Luminescent device has the advantages that electroluminescent efficiency is good and excitation is excellent and life-span length.
Brief description
Fig. 1 is the hydrogen nuclear magnetic spectrogram of compound 1.
Fig. 2 is a kind of organic electroluminescence device structural representation of the present invention
Wherein, 110 it is represented as glass substrate, 120 are represented as anode, 130 are represented as hole transmission layer, 140 are represented as sending out
Photosphere, 150 are represented as electron transfer layer, and 160 are represented as electron injecting layer, and 170 are represented as negative electrode.
Specific embodiment
In order to describe the present invention in more detail, especially exemplified by example below, but not limited to this.
Embodiment 1
The synthesis of compound 1
The synthesis of intermediate 1-1
In the 100ml single port bottle being dried, sequentially add phenanthrenequione (2g, 9.6mmol), the bromo- o-phenylenediamine of 4- (1.8g,
9.6mmol), dehydrated alcohol 50ml, acetic acid 25ml.After stirring 0.5h under room temperature, filter, obtain faint yellow solid 2.3g, yield
For 67%.1H NMR(400MHz,CDCl3)δ:9.36 (d, J=7.9Hz, 2H), 8.57 (d, J=8.0Hz, 2H), 8.52 (d, J
=2.1Hz, 1H), 8.19 (d, J=9.0Hz, 1H), 7.91 (dd, J=9.0,2.1Hz, 1H), 7.82 (t, J=7.5Hz, 2H),
7.75 (t, J=7.5Hz, 2H).
The synthesis of compound 1
In the 50ml single port bottle being dried, sequentially add intermediate 1-1 (0.3g, 8.4mmol), 4- (1- phenyl -1H- benzene
And imidazoles -2- base) phenylboric acid (0.27g, 8.4mmol), K2CO3(2.3g, 16.8mmol), THF (30ml), water (5ml) and four or three
Phenylphosphine palladium (50mg, 0.05mmol), under argon protection, reactant liquor is heated to backflow, stirs 3h.After reaction stops, recovering
To room temperature, wash, dichloromethane extracts, merge organic faciess, be spin-dried for, column chromatography for separation (petroleum ether：Ethyl acetate=1:3), obtain
To faint yellow solid 0.18g, yield is 38%.1H NMR(400MHz,CDCl3)δ:9.42 (d, J=7.8Hz, 2H), 8.59 (d,
J=8.0Hz, 2H), 8.56 (d, J=1.9Hz, 1H), 8.39 (d, J=8.8Hz, 1H), 8.14 (dd, J=8.9,1.9Hz,
1H), 7.94 (d, J=8.1Hz, 1H), 7.80 (m, 8H), 7.58 (m, 4H), 7.42 (d, J=6.9Hz, 2H), 7.31 (d, J=
5.8Hz,2H).
Embodiment 2
The synthesis of compound 17
The synthesis of intermediate 17-1
Synthetic method, similar to the synthesis of intermediate 1-1, finally obtains absinthe-green solid, and yield is 60%.1H NMR
(400MHz,CDCl3)δ:9.59 (ddd, J=8.1,5.0,1.8Hz, 2H), 9.29 (dd, J=4.4,1.7Hz, 2H), 8.55
(d, J=2.1Hz, 1H), 8.21 (d, J=9.0Hz, 1H), 7.98 (dd, J=9.0,2.2Hz, 1H), 7.80 (ddd, J=8.1,
4.5,1.4Hz,2H).
The synthesis of compound 17
In the 50ml single port bottle being dried, sequentially add intermediate 17-1 (0.3g, 0.84mmol), 4- (1- phenyl -1H-
Benzimidazolyl-2 radicals-yl) phenylboric acid (0.27g, 0.84mmol), K2CO3(2.3g, 16.8mmol), THF (30ml), water (5ml) and
Tetra-triphenylphosphine palladium (50mg, 0.05mmol), under argon protection, reactant liquor is heated to backflow, after stirring 3h. reaction stops,
Recover to room temperature, wash, dichloromethane extracts, merge organic faciess, be spin-dried for, column chromatography for separation (petroleum ether：Ethyl acetate=1:
1), obtain faint yellow solid 0.21g, yield is 46%.ESI,m/z:[M+H]+：551.22.
Embodiment 3
The synthesis of compound 47
The synthesis of intermediate 47-1
Add compound 2- (4- bromophenyl) -4,6- diphenyl -1,3,5-triazines (2g, 5.1mmol) in flask, join boron
Acid frequency receives alcohol ester (1.5g, 6.18mmol), potassium acetate (15.4mmol), Pd (dppf)2Cl2(100mg), the N of 40ml, N- diformazan
Base Methanamide, is heated to 90 DEG C under nitrogen protection and reacts 12 hours, and cooling is poured into water, and with dichloromethane extraction, uses anhydrous sulfur
Sour sodium is dried, and concentrates, and crude product silica column purification obtains 1.5g white solid, and yield is 68%.1H NMR(400MHz,CDCl3,
δ):8.75-8.80 (m, 6H), 8.00-8.02 (d, J=8Hz, 2H), 7.57-7.63 (m, 6H), 1.40 (s, 12H).
The synthesis of compound 47
In the 50ml single port bottle being dried, sequentially add intermediate 47-1 (0.4g, 0.92mmol), intermediate 1-1
(0.33g, 0.92mmol), K2CO3(2.3g, 16.8mmol), THF (30ml), water (5ml) and tetra-triphenylphosphine palladium (50mg,
0.05mmol), under argon protection, reactant liquor is heated to backflow, stirs 3h.After reaction stops, recovering to room temperature, wash, two
Chloromethanes extract, and merge organic faciess, are spin-dried for, column chromatography for separation (petroleum ether：Ethyl acetate=1:3), obtain faint yellow solid
0.27g, yield is 50%.ESI,m/z:[M+H]+：588.65.
Embodiment 4
The synthesis of compound 75
In the 50ml single port bottle being dried, sequentially add intermediate 47-1 (0.4g, 0.92mmol), intermediate 17-1
(0.3g, 0.7mmol), K2CO3(2.3g, 16.8mmol), THF (30ml), water (5ml) and tetra-triphenylphosphine palladium (50mg,
0.05mmol), under argon protection, reactant liquor is heated to backflow, after stirring 3h. reaction stops, recovering to room temperature, wash, two
Chloromethanes extract, and merge organic faciess, are spin-dried for, column chromatography for separation (petroleum ether：Ethyl acetate=1:3), obtain faint yellow solid
0.15g, yield is 37%.ESI,m/z:[M+H]+：590.33.
Embodiment 5
The preparation of organic electroluminescence device
Compound 1 using embodiment 1 prepares OLED
First, by electrically conducting transparent ito glass substrate 110 (carrying anode 120 above) (the limited public affairs of South China glass group share
Department) warp successively：Deionized water, ethanol, acetone and deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, it is deposited with NPB, form the thick hole transmission layer 130 of 60nm.
Then, the thick Alq of evaporation 37.5nm on hole transmission layer3Adulterate 1% weight ratio C545T as luminescent layer
140.
Then, the thick compound 1 of 37.5nm is deposited with luminescent layer as electron transfer layer 150.
Finally, it is deposited with 1nm LiF for electron injecting layer 160 and 100nm Al as device cathodes 170.
Prepared device (structural representation is shown in Fig. 2) is recorded in 20mA/ with Photo Research PR650 spectrogrph
cm2Electric current density under power efficiency be 6.2lm/W, launch green glow.
Comparative example 1
First, by electrically conducting transparent ito glass substrate 110 (carrying anode 120 above) (the limited public affairs of South China glass group share
Department) warp successively：Deionized water, ethanol, acetone and deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, it is deposited with NPB, form the thick hole transmission layer 130 of 60nm.
Then, the thick Alq of evaporation 37.5nm on hole transmission layer31%C545T is as luminescent layer 140 for doping.
Then, the thick Alq of evaporation 37.5nm on luminescent layer3As electron transfer layer 150.
Finally, it is deposited with 1nm LiF for electron injecting layer 160 and 100nm Al as device cathodes 170.
Prepared device is recorded in 20mA/cm with Photo Research PR650 spectrogrph2Electric current density under
Power efficiency is 5.0lm/W, launches green glow.
At identical conditions, the organic electroluminescent electron transport material preparation of the azophenlyene analog derivative of the application present invention
Organic electroluminescence device efficiency be higher than comparative example, as described above, the compound of the present invention has high stability, this
The organic electroluminescence device of bright preparation has high efficiency and optical purity.
Structural formula described in device
Claims (6)
1. a kind of organic electroluminescent compounds of azophenlyene analog derivative are it is characterised in that it is the change with following structure Formulas I
Compound：
Wherein, R1、R2、R3、R4、R5、R6、R7、R8、R10Separately be selected from hydrogen, the substituted or unsubstituted alkyl of C1-C12 or
Cycloalkyl；
L is selected from the substituted or unsubstituted aryl of C6-C30；
X1、X2For CH；
Ar is
Wherein R11、R12、R13、R14Separately it is selected from hydrogen, the substituted or unsubstituted alkyl of C1-C12；
Wherein X5For NR15；
R15Replacement for C6-C60 or unsubstituted aryl.
2. the organic electroluminescent compounds of azophenlyene analog derivative according to claim 1 are it is characterised in that wherein：
R1、R2、R3、R4、R5、R6、R7、R8、R10Separately it is selected from hydrogen, the alkyl of C1-C8；
L be selected from phenyl, replaced by C1-C4 alkyl phenyl, naphthyl, the naphthyl being replaced by C1-C4 alkyl, xenyl, by C1-C4
The xenyl that alkyl replaces.
3. the organic electroluminescent compounds of azophenlyene analog derivative according to claim 1 are it is characterised in that wherein：
R1、R2、R3、R4、R5、R6、R7、R8、R10Separately it is selected from hydrogen, methyl, ethyl, propyl group, isopropyl, the tert-butyl group, positive fourth
Base, n-hexyl.
4. the organic electroluminescent compounds of azophenlyene analog derivative according to claim 3 are it is characterised in that wherein：
R11～R14Separately it is selected from hydrogen, methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl；
R15Selected from by the substituted or unsubstituted following aryl of the alkyl of C1-C8：
5. the azophenlyene analog derivative according to any one of claim 1-4 organic electroluminescent compounds it is characterised in that
It is the compound of following structural：
6. the organic electroluminescent compounds of the azophenlyene analog derivative described in any one of claim 1-5 are in organic electroluminescence
Application in part.
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| KR102639569B1 (en) * | 2016-06-20 | 2024-02-23 | 삼성디스플레이 주식회사 | Condensed compound and organic light emitting device comprising the same |
| CN107827879B (en) * | 2017-09-14 | 2021-06-04 | 奥来德(上海)光电材料科技有限公司 | Material for flexible display, preparation method thereof and organic electroluminescent device |
| CN109748918A (en) * | 2019-01-10 | 2019-05-14 | 江苏理工学院 | Double pyridine anchoring group dye sensitizing agents and preparation method and application |
| CN110628022B (en) * | 2019-09-25 | 2021-06-22 | 福州大学 | Phenazine group-containing organic polymer, preparation method thereof and catalytic application thereof to benzylamine oxidative coupling reaction |
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| CN104650040A (en) | 2015-05-27 |
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