CN104650040A - Organic electroluminescent compound of phenazine derivative - Google Patents
Organic electroluminescent compound of phenazine derivative Download PDFInfo
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Abstract
The invention provides an organic electroluminescent compound of a phenazine derivative. The organic electroluminescent compound is a compound shown in a structural formula I. The organic electroluminescent compound can be used for preparing an organic electroluminescent apparatus. The formula is shown in the description.
Description
Technical field
The present invention relates to field of organic electroluminescence, relate to a kind of organic electroluminescent compounds of azophenlyene analog derivative specifically.
Background technology
Organic electroluminescence device (OLEDs) is deposit by spin coating or vacuum evaporation the device that one deck organic materials is prepared between two metal electrodes, classical three layers of organic electroluminescence device comprise hole transmission layer, luminescent layer and electron transfer layer.The hole produced by anode is followed through hole transmission layer the electronics produced by negative electrode to be combined in luminescent layer through electron transfer layer and is formed exciton, then luminous.Organic electroluminescence device can regulate by the material changing luminescent layer the light launching various needs as required.
Organic electroluminescence device is as a kind of novel technique of display, there is luminous, wide viewing angle, less energy-consumption, efficiency are high, thin, rich color, fast response time, Applicable temperature scope wide, low driving voltage, flexible and the particular advantages such as transparent display panel and environmental friendliness can be made, can be applied in flat-panel monitor and a new generation's illumination, also can as the backlight of LCD.
Since invention at the bottom of the eighties in 20th century, organic electroluminescence device is industrially applied to some extent, such as the screen such as camera and mobile phone, but current OLED due to efficiency low, the factors such as work-ing life is short restrict it and apply widely, particularly large screen display.And restrict the performance that one of them important factor is exactly the electroluminescent organic material in organic electroluminescence device.In addition because OLED is when applying voltage-operated, can joule heating be produced, make organic materials easily crystallization occur, have impact on life-span and the efficiency of device, therefore, also need the electroluminescent organic material developing stability and high efficiency.
In OLED material, because the speed of most electroluminescent organic material transporting holes is faster than the speed of transmission electronic, easily cause electronics and the number of cavities imbalance of luminescent layer, the efficiency of such device is just lower.Three (oxine) aluminium (Alq
3) since invention, be extensively studied, but it is still very low as its electronic mobility of electron transport material, and the intrinsiccharacteristic that self can degrade, with in the device of electron transfer layer, there will be the situation of voltage drop, simultaneously, due to lower electronic mobility, a large amount of holes is made to enter into Alq
3in layer, excessive hole with the form quantity of radiant energy of non-luminescent, and when as electron transport material, due to the characteristic of its green light, application is restricted.Therefore, development stability and have the electron transport material of larger electronic mobility, has great value to widely using of organic electroluminescence device.
Summary of the invention
First the present invention provides a kind of organic electroluminescent compounds of azophenlyene analog derivative, and it is the compound with following structural formula I:
Wherein, R
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8, R
10separately be selected from hydrogen, D atom, halogen, hydroxyl, cyano group, nitro, the substituted or unsubstituted alkyl or cycloalkyl of C1-C12, the alkoxyl group of C1-C8, the replacement of C6-C30 or unsubstituted aryl, the replacement of C3-C30 or unsubstituted heteroaryl, the replacement of C2-C8 or unsubstituted thiazolinyl, the replacement of C2-C8 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, the replacement of C3-C30 or unsubstituted heteroaryl;
X
1, X
2separately be selected from CH, N;
Ar is the replacement of C3-C60 or unsubstituted aryl or heteroaryl;
Wherein preferred mode is:
R
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8, R
10separately be selected from hydrogen, halogen, cyano group, nitro, the alkyl of C1-C8, the alkoxyl group of C1-C8, phenyl, naphthyl, pyridyl, pyrimidyl, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinoline;
L is independently selected from sky, singly-bound, phenyl, the phenyl replaced by C1-C4 alkyl, naphthyl, the naphthyl replaced by C1-C4 alkyl, xenyl, the xenyl that replaced by C1-C4 alkyl;
Ar is dibenzothiophene base, dibenzofuran group, pyridyl, pyrimidyl, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinolyl, benzimidazolyl-;
Wherein above-mentioned dibenzothiophene base, dibenzofuran group, pyridyl, pyrimidyl, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinolyl, benzimidazolyl-can further replace by the aryl of the alkyl of C1-C4 or C6-C30;
Preferred mode is further:
R
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8, R
10separately be selected from hydrogen, fluorine, nitro, methyl, ethyl, propyl group, sec.-propyl, the tertiary butyl, normal-butyl, n-hexyl, phenyl, naphthyl;
Ar is
Wherein Ar
1and Ar
2be hydrogen, the substituted or unsubstituted alkyl of C1-C12, the replacement of C6-C60 or unsubstituted aryl, the replacement of C3-C60 or unsubstituted heteroaryl independently;
Wherein X
3and X
4be expressed as CH and N independently;
Wherein R
11, R
12, R
13, R
14separately be selected from hydrogen, D atom, halogen, cyano group, nitro,
The replacement of the replacement of the replacement of the substituted or unsubstituted alkyl of C1-C12, the alkoxyl group of C1-C8, the replacement of C6-C30 or unsubstituted aryl, C3-C30 or unsubstituted heteroaryl, C2-C8 or unsubstituted thiazolinyl, C2-C8 or unsubstituted alkynyl;
Wherein X
5be selected from O, S, Se, NR
15;
R
15for replacement or the unsubstituted heteroaryl of the substituted or unsubstituted alkyl of hydrogen, C1-C12, the replacement of C6-C60 or unsubstituted aryl, C3-C60;
Preferred mode is further:
R
11~ R
14separately be selected from hydrogen, fluorine, nitro, methyl, ethyl, propyl group, sec.-propyl, the tertiary butyl, normal-butyl, n-hexyl, phenyl, naphthyl;
Wherein X
5for NR
15;
R
15, Ar
1and Ar
2be selected from hydrogen, methyl, ethyl, propyl group, sec.-propyl, the tertiary butyl, normal-butyl, n-hexyl, by the substituted or unsubstituted following aryl of the alkyl of C1-C8 or heteroaryl:
Preferred further, the organic electroluminescent compounds of azophenlyene analog derivative of the present invention is the compound of following structural 1-86:
The organic electroluminescent compounds of azophenlyene analog derivative of the present invention can be prepared by Suzuki linked reaction.
The organic electroluminescent compounds of azophenlyene analog derivative of the present invention can be applied in organic electroluminescence device, organic solar batteries, OTFT or organophotoreceptorswith field.
Present invention also offers a kind of organic electroluminescence device, this device comprises anode, negative electrode and organic layer, it is one or more layers that organic layer comprises in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer or electron transfer layer, has one deck at least containing, for example the organic electroluminescent compounds of the azophenlyene analog derivative described in structural formula (I) in wherein said organic layer:
Wherein R
1-R
10, Ar, L, X
1-X
2definition as previously mentioned.
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 blocking layer;
Or organic layer is luminescent layer, hole transmission layer, electron transfer layer, electron injecting layer and blocking layer;
Or organic layer is luminescent layer, hole transmission layer, electron injecting layer and blocking layer;
The layer at the organic electroluminescent compounds place of the azophenlyene analog derivative wherein as described in structural formula (I) is electron transfer layer or electron injecting layer;
The organic electroluminescent compounds of the azophenlyene analog derivative wherein described in structural formula (I) is the compound of structural formula 1-86;
The organic electroluminescent compounds of the azophenlyene analog derivative as described in structural formula I can be used alone, and also can use with other compound; The organic electroluminescent compounds of the azophenlyene analog derivative as described in structural formula I can be used alone a kind of compound wherein, also can use two or more the compound in structural formula I simultaneously.
Organic electroluminescence device of the present invention, preferred mode is further, this organic electroluminescence device comprises anode, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, the compound wherein containing structural formula (I) in electron transfer layer or electron injecting layer; Further preferred, the compound in electron transfer layer or electron injecting layer is the compound of structural formula 1-86.
Organic electroluminescence device of the present invention, Compounds of structural formula I also doublely can do electron injecting layer as during electron transfer layer.
The total thickness of organic electroluminescence device organic layer of the present invention is 1-1000nm, preferred 50-500nm.
Organic electroluminescence device of the present invention is when using the present invention to have the compound of structural formula I, collocation other materials can be used, as hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and blocking layer etc., and obtain blue light, green glow, gold-tinted, ruddiness or white light.
The hole transmission layer of organic electroluminescence device of the present invention and hole injection layer, material requested has good hole transport performance, can effectively hole be transferred to luminescent layer from anode.Other small molecules and macromolecular organic compound can be comprised, include but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine-like compound, six cyano group six mix triphen (hexanitrilehexaazatriphenylene), 2,3,5,6-tetra-fluoro-7,7', 8,8'-tetra-cyanogen dimethyl-parabenzoquinone (F4-TCNQ), Polyvinyl carbazole, Polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of organic electroluminescence device of the present invention, has the good characteristics of luminescence, can regulate the scope of visible ray as required.Can containing, for example lower compound, include, but are not limited to naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance compounds, bend compounds, fluoranthene compounds, anthracene compounds, pentacene compounds, perylene compounds, two aromatic ethylene compounds, triphenylamine ethylene compounds, aminated compounds, carbazole compound, benzimidazoles compound, furfuran compound, metal organic fluorescence complex compound, metal Phosphorescent complex compound is (as Ir, Pt, Os, Cu, Au), polyvinyl carbazole, poly organic silicon compound, the organic polymer luminescent materials such as Polythiophene, they can be used alone, also can use by multiple mixture.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires to have good electronic transmission performance, effectively during electronics is from cathode transport to luminescent layer, can have very large electronic mobility.Have except Compounds of structural formula I except of the present invention, following compound can also be selected, but be not limited thereto, oxa-oxazole, thiazole compound, triazole compound, three nitrogen piperazine compounds, triazine compounds, quinoline compounds, phenazine compounds, siliceous heterocyclic compound, quinolines, phenanthroline compounds, metallo-chelate (as Alq3), fluorine substituted benzene compound, benzimidazoles compound.
The electron injecting layer of organic electroluminescence device of the present invention, can effectively electronics be injected into organic layer from negative electrode, have except Compounds of structural formula I except of the present invention, mainly be selected from basic metal or alkali-metal compound, or be selected from compound or the alkali metal complex of alkaline-earth metal or alkaline-earth metal, following compound can be selected, but be not limited thereto, basic metal, alkaline-earth metal, rare earth metal, alkali-metal oxide compound or halogenide, the oxide compound of alkaline-earth metal or halogenide, the oxide compound of rare earth metal or halogenide, the organic complex of basic metal or alkaline-earth metal, be preferably lithium, lithium fluoride, Lithium Oxide 98min, lithium nitride, oxine lithium, caesium, cesium carbonate, oxine caesium, calcium, Calcium Fluoride (Fluorspan), calcium oxide, magnesium, magnesium fluoride, magnesiumcarbonate, magnesium oxide, these compounds can be used alone also can mixture use, also can with other electroluminescent organic materials with the use of.
Every one deck of organic layer in organic electroluminescence device of the present invention, can be prepared by modes such as vacuum vapour deposition, molecular beam vapour deposition method, the dip coating being dissolved in solvent, spin-coating method, stick coating method or spray ink Printings.Vapour deposition method or sputtering method can be used to be prepared for metal motor.
Device experimental shows, the organic electroluminescent compounds of the azophenlyene analog derivative of the present invention as described in structural formula (I), has better thermostability, high-luminous-efficiency, high luminance purity.The organic electroluminescence device adopting this organic electroluminescent compounds to make has the advantage that electroluminescent efficiency is good and purity of color is excellent and the life-span is long.
Accompanying drawing explanation
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 are represented as glass substrate, and 120 are represented as anode, and 130 are represented as hole transmission layer, and 140 are represented as luminescent layer, and 150 are represented as electron transfer layer, and 160 are represented as electron injecting layer, and 170 are represented as negative electrode.
Embodiment
In order to more describe the present invention in detail, especially exemplified by following example, but be not limited thereto.
Embodiment 1
The synthesis of compound 1
The synthesis of intermediate 1-1
In the 100ml single port bottle of drying, add phenanthrenequione (2g, 9.6mmol) successively, the bromo-O-Phenylene Diamine (1.8g, 9.6mmol) of 4-, dehydrated alcohol 50ml, acetic acid 25ml.After stirring 0.5h under normal temperature, filter, obtain faint yellow solid 2.3g, productive rate is 67%.
1H NMR(400MHz,CDCl
3)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 of drying, add intermediate 1-1 (0.3g, 8.4mmol) successively, 4-(1-phenyl-1H-benzimidazolyl-2 radicals-Ji) phenylo boric acid (0.27g, 8.4mmol), K
2cO
3(2.3g, 16.8mmol), THF (30ml), water (5ml) and tetra-triphenylphosphine palladium (50mg, 0.05mmol), under argon shield, be heated to backflow by reaction solution, stirs 3h.Reaction returns to room temperature after stopping, washing, dichloromethane extraction, and merge organic phase, be spin-dried for, column chromatography for separation (sherwood oil: ethyl acetate=1:3), obtain faint yellow solid 0.18g, productive rate is 38%.
1H NMR(400MHz,CDCl
3)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 is similar to the synthesis of intermediate 1-1, finally obtains absinthe-green solid, and productive rate is 60%.
1H NMR(400MHz,CDCl
3)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 of drying, add intermediate 17-1 (0.3g, 0.84mmol) successively, 4-(1-phenyl-1H-benzimidazolyl-2 radicals-Ji) phenylo boric acid (0.27g, 0.84mmol), K
2cO
3(2.3g, 16.8mmol), THF (30ml); water (5ml) and tetra-triphenylphosphine palladium (50mg, 0.05mmol), under argon shield; reaction solution is heated to backflow, after stirring 3h. reaction stopping, returns to room temperature; washing, dichloromethane extraction, merges organic phase; be spin-dried for; column chromatography for separation (sherwood oil: ethyl acetate=1:1), obtain faint yellow solid 0.21g, productive rate is 46%.ESI,m/z:[M+H]
+：551.22.
Embodiment 3
The synthesis of compound 47
The synthesis of intermediate 47-1
Compound 2-(4-bromophenyl)-4,6-phenylbenzene-1,3 is added in flask, 5-triazine (2g, 5.1mmol), connection boric acid frequently receives alcohol ester (1.5g, 6.18mmol), Potassium ethanoate (15.4mmol), Pd (dppf)
2cl
2(100mg), the DMF of 40ml, is heated to 90 DEG C of reactions 12 hours under nitrogen protection; cooling, is poured into water, with dichloromethane extraction, with anhydrous sodium sulfate drying; concentrated, crude product silica column purification obtains 1.5g white solid, and productive rate is 68%.
1H NMR(400MHz,CDCl
3,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 of drying, add intermediate 47-1 (0.4g, 0.92mmol) successively, intermediate 1-1 (0.33g, 0.92mmol), K
2cO
3(2.3g, 16.8mmol), THF (30ml), water (5ml) and tetra-triphenylphosphine palladium (50mg, 0.05mmol), under argon shield, be heated to backflow by reaction solution, stirs 3h.Reaction returns to room temperature after stopping, washing, dichloromethane extraction, and merge organic phase, be spin-dried for, column chromatography for separation (sherwood oil: ethyl acetate=1:3), obtain faint yellow solid 0.27g, productive rate is 50%.ESI,m/z:[M+H]
+：588.65.
Embodiment 4
The synthesis of compound 75
In the 50ml single port bottle of drying, add intermediate 47-1 (0.4g, 0.92mmol) successively, intermediate 17-1 (0.3g, 0.7mmol), K
2cO
3(2.3g, 16.8mmol), THF (30ml); water (5ml) and tetra-triphenylphosphine palladium (50mg, 0.05mmol), under argon shield; reaction solution is heated to backflow, after stirring 3h. reaction stopping, returns to room temperature; washing, dichloromethane extraction, merges organic phase; be spin-dried for; column chromatography for separation (sherwood oil: ethyl acetate=1:3), obtain faint yellow solid 0.15g, productive rate is 37%.ESI,m/z:[M+H]
+：590.33.
Embodiment 5
The preparation of organic electroluminescence device
The compound 1 of embodiment 1 is used to prepare OLED
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (China Nanbo Group Co) warp successively: deionized water, ethanol, acetone and deionized water are cleaned, then use oxygen plasma treatment 30 seconds.
Then, evaporation NPB, forms the hole transmission layer 130 that 60nm is thick.
Then, the Alq that evaporation 37.5nm is thick on hole transmission layer
3the C545T of 1% weight ratio of adulterating is as luminescent layer 140.
Then, the compound 1 that evaporation 37.5nm is thick on luminescent layer is as electron transfer layer 150.
Finally, evaporation 1nm LiF is that electron injecting layer 160 and 100nm Al are as device cathodes 170.
Prepared device (structural representation is shown in Fig. 2) records at 20mA/cm with Photo Research PR650 spectrograph
2current density under power efficiency be 6.2lm/W, transmitting green light.
Comparative example 1
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (China Nanbo Group Co) warp successively: deionized water, ethanol, acetone and deionized water are cleaned, then use oxygen plasma treatment 30 seconds.
Then, evaporation NPB, forms the hole transmission layer 130 that 60nm is thick.
Then, the Alq that evaporation 37.5nm is thick on hole transmission layer
31%C545T is as luminescent layer 140 in doping.
Then, the Alq that evaporation 37.5nm is thick on luminescent layer
3as electron transfer layer 150.
Finally, evaporation 1nm LiF is that electron injecting layer 160 and 100nm Al are as device cathodes 170.
Prepared device Photo Research PR650 spectrograph records at 20mA/cm
2current density under power efficiency be 5.0lm/W, transmitting green light.
At identical conditions, the efficiency of organic electroluminescence device prepared by the organic electroluminescent electron transport material applying azophenlyene analog derivative of the present invention is higher than comparative example, as mentioned above, compound of the present invention has high stability, and organic electroluminescence device prepared by the present invention has high efficiency and optical purity.
Structural formula described in device
Claims (6)
1. an organic electroluminescent compounds for azophenlyene analog derivative, is characterized in that it is the compound with following structural formula I:
Wherein, R
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8, R
10separately be selected from hydrogen, D atom, halogen, hydroxyl, cyano group, nitro, the substituted or unsubstituted alkyl or cycloalkyl of C1-C12, the alkoxyl group of C1-C8, the replacement of C6-C30 or unsubstituted aryl, the replacement of C3-C30 or unsubstituted heteroaryl, the replacement of C2-C8 or unsubstituted thiazolinyl, the replacement of C2-C8 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, the replacement of C3-C30 or unsubstituted heteroaryl;
X
1, X
2separately be selected from CH, N;
Ar is the replacement of C3-C60 or unsubstituted aryl or heteroaryl.
2. the organic electroluminescent compounds of azophenlyene analog derivative according to claim 1, is characterized in that wherein:
R
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8, R
10separately be selected from hydrogen, halogen, cyano group, nitro, the alkyl of C1-C8, the alkoxyl group of C1-C8, phenyl, naphthyl, pyridyl, pyrimidyl, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinoline;
L is independently selected from sky, singly-bound, phenyl, the phenyl replaced by C1-C4 alkyl, naphthyl, the naphthyl replaced by C1-C4 alkyl, xenyl, the xenyl that replaced by C1-C4 alkyl;
Ar is dibenzothiophene base, dibenzofuran group, pyridyl, pyrimidyl, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinolyl, benzimidazolyl-.
3. the organic electroluminescent compounds of azophenlyene analog derivative according to claim 1, is characterized in that wherein:
R
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8, R
10separately be selected from hydrogen, fluorine, nitro, methyl, ethyl, propyl group, sec.-propyl, the tertiary butyl, normal-butyl, n-hexyl, phenyl, naphthyl;
Ar is
with
Wherein Ar
1and Ar
2be hydrogen, the substituted or unsubstituted alkyl of C1-C12, the replacement of C6-C60 or unsubstituted aryl, the replacement of C3-C60 or unsubstituted heteroaryl independently;
Wherein X
3and X
4be expressed as CH and N independently;
Wherein R
11, R
12, R
13, R
14separately be selected from hydrogen, D atom, halogen, cyano group, nitro, the substituted or unsubstituted alkyl of C1-C12, the alkoxyl group of C1-C8, the replacement of C6-C30 or unsubstituted aryl, the replacement of C3-C30 or unsubstituted heteroaryl, the replacement of C2-C8 or unsubstituted thiazolinyl, the replacement of C2-C8 or unsubstituted alkynyl;
Wherein X
5be selected from O, S, Se, NR
15;
R
15for replacement or the unsubstituted heteroaryl of the substituted or unsubstituted alkyl of hydrogen, C1-C12, the replacement of C6-C60 or unsubstituted aryl, C3-C60.
4. the organic electroluminescent compounds of azophenlyene analog derivative according to claim 3, is characterized in that wherein:
R
11~ R
14separately be selected from hydrogen, fluorine, nitro, methyl, ethyl, propyl group, sec.-propyl, the tertiary butyl, normal-butyl, n-hexyl, phenyl, naphthyl;
Wherein X
5for NR
15;
R
15, Ar
1and Ar
2be selected from hydrogen, methyl, ethyl, propyl group, sec.-propyl, the tertiary butyl, normal-butyl, n-hexyl, by the substituted or unsubstituted following aryl of the alkyl of C1-C8 or heteroaryl:
5. the organic electroluminescent compounds of the azophenlyene analog derivative according to any one of claim 1-4, is characterized in that it is the compound of following structural 1-86:
6. the application of organic electroluminescent compounds in organic electroluminescence device of the azophenlyene analog derivative described in any one of claim 1-5.
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| KR20170143116A (en) * | 2016-06-20 | 2017-12-29 | 삼성디스플레이 주식회사 | Condensed compound and organic light emitting device comprising the same |
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| CN110628022A (en) * | 2019-09-25 | 2019-12-31 | 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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| CN106558654A (en) * | 2015-09-30 | 2017-04-05 | 北京鼎材科技有限公司 | A kind of phenonaphthazine derivant and its application in organic electroluminescence device |
| CN106558654B (en) * | 2015-09-30 | 2020-01-14 | 北京鼎材科技有限公司 | Benzophenazine derivative and application thereof in organic electroluminescent device |
| KR20170143116A (en) * | 2016-06-20 | 2017-12-29 | 삼성디스플레이 주식회사 | Condensed compound and organic light emitting device comprising the same |
| KR102639569B1 (en) | 2016-06-20 | 2024-02-23 | 삼성디스플레이 주식회사 | Condensed compound and organic light emitting device comprising the same |
| CN107827879A (en) * | 2017-09-14 | 2018-03-23 | 上海珂力恩特化学材料有限公司 | A kind of material available for Flexible Displays and preparation method thereof and organic electroluminescence device |
| 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 |
| CN110628022A (en) * | 2019-09-25 | 2019-12-31 | 福州大学 | Phenazine group-containing organic polymer, preparation method thereof and catalytic application thereof to benzylamine oxidative coupling reaction |
| 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 |
| CN113248451A (en) * | 2020-04-27 | 2021-08-13 | 广东聚华印刷显示技术有限公司 | Quinoxaline compound, polymer, organic electronic device and display panel |
| CN113248451B (en) * | 2020-04-27 | 2023-04-28 | 广东聚华印刷显示技术有限公司 | Quinoxaline compound, polymer, organic electronic device and display panel |
| CN114644632A (en) * | 2022-03-01 | 2022-06-21 | 苏州大学 | Thermal activation delayed fluorescence material based on bispyridophenazine receptor and preparation method and application thereof |
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