CN104617224A - Organic electroluminescence device - Google Patents
Organic electroluminescence device Download PDFInfo
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
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- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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Abstract
The invention provides an organic electroluminescence device. The organic electroluminescence device comprises a positive pole, a negative pole and an organic layer, wherein the organic layer contains one or more than one of a hole injection layer, a hole transmission layer, a luminescence layer, a barrier layer, an electron injection layer and an electron transmission layer. The organic electroluminescence device is characterized in that at least one layer in the organic layer comprises a compound based on a carbazole derivative, which has the structure formula (I) in the specification.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, relate to a kind of organic electroluminescence device specifically.
Technical background
Organic electroluminescence device (OLEDs) is deposit by spin coating or vacuum evaporation the device that one deck organic material 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 Display Technique, there is self-luminous, wide viewing angle, low 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 floater 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 useful life is short restrict it and apply widely, particularly large screen display, therefore needs the efficiency improving device.And restrict the performance that one of them key factor is exactly the electroluminescent organic material in organic electroluminescence device.In addition because OLED is when applying voltage-operated, can Joule heat be produced, make organic material 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.
Organic electrophosphorescenpolymer phenomenon, breach organic electroluminescent quantum efficiency lower than 25% theory restriction, rise to 100% (Baldo M.A., Forrest S.R.Et al, Nature, 1998,395,151-154), its application also greatly increases the efficiency of organic electroluminescence device.Usually, electroluminescent phosphorescence needs to adopt host-guest system technology, the conventional CBP (4 as phosphorescent light body material, 4'-bis (9-carbazolyl)-biphenyl) there is efficient and high triplet energy level, when it is as material of main part, triplet energy state can effectively from light emitting host material transfer to object phosphorescent light-emitting materials.But the hole due to CBP is easily transmitted and the characteristic of electronics difficulty flowing, and make the charge unbalance of luminescent layer, result reduces the efficiency of device.
Summary of the invention
First the present invention provides a kind of compound based on carbazole derivates, and it is the compound with following structural formula I:
Wherein L is sky, singly-bound, the substituted or unsubstituted alkyl of C1-C8, the substituted or unsubstituted aryl of C6-C30, the replacement of C3-C30 or unsubstituted heteroaryl;
Wherein X
1and X
2be expressed as CH or N independently;
Wherein Ar
1be selected from the substituted or unsubstituted alkyl of C1-C12, the replacement of C6-C60 or unsubstituted aryl, the replacement of C3-C60 or unsubstituted heteroaryl, the replacement of C2-C8 or unsubstituted thiazolinyl, the replacement of C2-C8 or unsubstituted alkynyl;
Wherein Ar
2be selected from as following structural:
Wherein A, B, C, D, E and F are independently selected from O, S, NAr
3or CAr
4ar
5;
Wherein, Ar
3, Ar
4and Ar
5separately be selected from the substituted or unsubstituted alkyl of C1-C8, the alkoxyl 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 preferred mode is:
The phenyl that L is selected from phenyl, replaced by C1-C4 alkyl, naphthyl, the naphthyl replaced by C1-C4 alkyl, xenyl or the xenyl replaced by C1-C4 alkyl;
Ar
1, Ar
3, Ar
4and Ar
5separately be selected from the alkyl of C1-C8, the alkoxyl of C1-C8, phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylene base, fluoranthene base, (9,9-dialkyl group) fluorenyl, (9,9-bis-replaces or unsubstituted aryl) fluorenyl, 9,9-Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinolyl, triaromatic amine base, carbazyl;
Wherein above-mentioned phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylene base, fluoranthene base, (9,9-dialkyl group) fluorenyl, (9,9-bis-replaces or unsubstituted aryl) fluorenyl, 9,9-Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinolyl can further replace by the aryl of the alkyl of C1-C4 or C6-C30;
Wherein said alkyl can be straight chain, side chain or for cycloalkyl;
Preferred mode is further:
L is selected from phenyl, naphthyl, xenyl;
Wherein Ar
1, Ar
3, Ar
4and Ar
5be selected from methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, by the substituted or unsubstituted following aryl of C1-C4 alkyl and heteroaryl:
Preferred further, the compound based on carbazole derivates of the present invention is the compound of following structural 1-30:
Compound based on carbazole derivates of the present invention can be prepared by Suzuki coupling reaction and Buchwald-Hartwig reaction.
Compound based on carbazole derivates 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 compound based on carbazole derivates described in structural formula (I) in wherein said organic layer:
Wherein X
1, X
2, Ar
1, Ar
2and the definition of L as previously mentioned.
Wherein organic layer is luminescent layer;
Or organic layer is luminescent layer and electron transfer layer;
Or organic layer is luminescent layer, electron transfer layer and electron injecting layer;
Or organic layer is hole transmission layer and luminescent layer;
Or organic layer is hole injection layer, hole transmission layer and luminescent layer;
Or organic layer is hole transmission layer, luminescent layer and electron transfer layer;
Or organic layer is hole injection layer, hole transmission layer, luminescent layer and electron transfer layer;
Or organic layer is hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer;
Or organic layer is hole injection layer, hole transmission layer, barrier layer, luminescent layer, electron transfer layer and electron injecting layer;
Or organic layer is hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and hole blocking layer;
Or organic layer is hole transmission layer, luminescent layer, electron injecting layer and hole blocking layer;
The layer at the compound place based on carbazole derivates wherein as described in structural formula (I) is luminescent layer;
The compound based on carbazole derivates wherein described in structural formula (I) is the compound of structural formula 1-30;
When the compound based on carbazole derivates as described in structural formula I is prepared for luminescent device, can be used alone, also can use with other compound; The compound based on carbazole derivates 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 injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, the compound wherein containing one or more structural formula (I) in luminescent layer; Preferred further, the compound containing one or more structural formula 1-30 in luminescent layer.
The luminescent layer of organic electroluminescence device contains phosphorescence light emitting guest material and has the compound of structural formula (I) as material of main part, wherein structural formula (I) compound is as material of main part, its concentration is the 20-99.9% of whole luminescent layer weight, preferred 80-99%, is more preferably 90-99%.
The gross 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 barrier 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 molecular 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.There is Compounds of structural formula I as except phosphorescent light body material except of the present invention, can also arrange in pairs or groups other phosphorescent light body materials, phosphorescence light emitting guest material can comprise the metal-organic complex of at least one metal be selected from ruthenium, copper, rhodium, silver, iridium, platinum, gold and osmium.
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 electron mobility.Following compound can be selected, but be not limited thereto, oxa-oxazole, thiazole compound, triazole compound, three nitrogen piperazine compounds, triazine compounds, quinoline compounds, phenazine compounds, siliceous heterocycle compound, quinolines, ferrosin 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, mainly be selected from alkali 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, the oxide of alkali metal, alkaline-earth metal, rare earth metal, alkali-metal oxide or halide, alkaline-earth metal or halide, the oxide of rare earth metal or the organic complex of halide, alkali metal or alkaline-earth metal; Be preferably lithium, lithium fluoride, lithia, lithium nitride, oxine lithium, caesium, cesium carbonate, oxine caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, 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 inkjet printings.Vapour deposition method or sputtering method can be used to be prepared for metal motor.
Device experimental shows, the compound based on carbazole derivates of the present invention as described in structural formula (I), has better thermal stability, high-luminous-efficiency, high luminance purity.The organic electroluminescence device adopting this compound based on carbazole derivates to make has the advantage that electroluminescent efficiency is good and colorimetric purity is excellent and the life-span is long.
Accompanying drawing explanation
Fig. 1 is the hydrogen nuclear magnetic spectrogram of compound 18.
Fig. 2 is the hydrogen nuclear magnetic spectrogram of compound 19.
Fig. 3 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 injection layer, and 140 are represented as hole transmission layer, and 150 are represented as luminescent layer, and 160 are represented as electron transfer layer, and 170 are represented as electron injecting layer, and 180 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.
The synthesis of embodiment 1 compound 18
The synthesis of intermediate 18-1
3-bromobenzaldehyde (5.5g) is added, phenanthrenequione (6g), aniline (4.5g) in there-necked flask; ammonium acetate (8g) and acetic acid (100ml); add hot reflux under nitrogen protection 12 hours, cooling, adds water; with dichloromethane extraction; anhydrous sodium sulfate drying, concentrated, crude product ethanol and carrene recrystallization; obtain product 8.5g, productive rate 65%.
1H NMR(400MHz,CDCl
3):δ8.46-8.86(d,J＝7.6Hz,1H),8.76-8.78(d,J＝8.4Hz,1H),8.70-8.72(d,J＝8.4Hz,1H),7.83(s,1H),7.10-7.77(m,13H).
The synthesis of intermediate 18-2
In single port flask, add compound 18-1 (4.49g, 10mmol), connection boric acid frequently receives alcohol ester (3.0g, 12mmol), potassium acetate (3.0g), dichloro two triphenylphosphine palladium (50mg), dioxane (60mL), be heated to 100 DEG C of reaction 12h, cross silica gel while hot, use washed with dichloromethane filter cake, revolve solvent evaporated, thick product column chromatography purification, obtains product 3.2g, productive rate 64.5%.
1H NMR(400MHz,CDCl
3):δ8.88-8.90(d,J＝7.6Hz,1H),8.77-8.79(d,J＝8.4Hz,1H),8.71-8.72(d,J＝8.4Hz,1H),8.14(s,1H),7.21-7.76(m,13H),1.33(s,12H).
The synthesis of intermediate 18-3
Bromo-9, the 9-dimethyl fluorenes (140g, 0.5mol) of 2-are added in reaction bulb; o-chloraniline (95g, 0.75mol), potassium tert-butoxide (90g; 0.8mol), palladium (3.3g, 15mmol); tri-butyl phosphine tetrafluoroborate (8.7g, 30mmol) and toluene (1.5L), add hot reflux 24 hours under nitrogen protection; cooling, washing, dry; removing toluene, thick product is crossed post purifying and is obtained 90g product, productive rate 57%.
The synthesis of intermediate 18-4
In flask, add intermediate 18-3 (40g, 0,125mol), sodium carbonate (40g, 0.38mol), palladium (0.5g, 2.2mmol), tricyclohexyl phosphine tetrafluoroborate (1.6g, 4.4mmol) and dimethylacetylamide (0.5L), add hot reflux 5 hours, cooling, subtract and steam remove portion solvent, cooling, is added to the water, is extracted with ethyl acetate, drying, crosses post purifying and obtains 15g product, productive rate 43%.
1H NMR(400MHz,CDCl
3):δ8.38(s,1H),8.05-8.14(m,2H),7.82-7.84(d,J＝7.6Hz,1H),7.23-7.45(m,7H),1.55(s,6H).
The synthesis of intermediate 18-5
Intermediate 18-4 (10g is added in reaction bulb; 35.3mmol); to bromo-iodobenzene (12g, 42mmol), potassium tert-butoxide (7.9g; 70.6mmol); palladium (0.3g, 1.3mmol), tri-butyl phosphine tetrafluoroborate (0.8g; 2.7mmol) with toluene (150mL); hot reflux is added 24 hours, cooling, removing toluene under nitrogen protection; add carrene; washing, dry, thick product crosses post; obtain 10g product, productive rate 57%.
The synthesis of compound 18
In single port flask, add intermediate 18-5 (0.6g, 1.4mmol), intermediate 18-2 (0.7g, 1.4mmol), potash (1.38g, 10mmol), tetra-triphenylphosphine palladium (10mg), oxolane (9mL), water (4mL), is heated to 80 DEG C of reaction 8h, cooling, with dichloromethane extraction, with anhydrous sodium sulfate drying, concentrate and obtain thick product, 0.31g product is being obtained, productive rate 30% through column chromatography for separation.
1h NMR (400MHz, CDCl
3): δ 8.91-8.93 (d, J=8.0Hz, 1H), 8.79-8.81 (d, J=8.4Hz, 1H), 8.72-8.74 (d, J=8.4Hz, 1H), 8.46 (s, 1H), 8.20-8.22 (d, J=7.6Hz, 1H), 7.97 (s, 1H), 7.86-7.88 (d, J=7.2Hz, 1H), 7.23-7.79 (m, 24H), 1.54 (s, 6H). the hydrogen nuclear magnetic spectrogram of compound 18 is shown in Fig. 1.
The synthesis of embodiment 2 compound 19
The synthesis of intermediate 19-1
Intermediate 18-4 (10g is added in reaction bulb; 35.3mmol); between bromo-iodobenzene (12g, 42mmol), potassium tert-butoxide (7.9g; 70.6mmol); palladium (0.3g, 1.3mmol), tri-butyl phosphine tetrafluoroborate (0.8g; 2.7mmol) with toluene (150mL); hot reflux is added 24 hours, cooling, removing toluene under nitrogen protection; add carrene; washing, dry, thick product crosses post; obtain 11g product, productive rate 71%.
1H NMR(400MHz,CDCl
3):δ8.43(s,1H),8.18-8.20(d,J＝7.6Hz,1H),7.85-7.87(d,J＝7.6Hz,1H),7.83-7.88(m,1H),7.64-7.66(m,1H),7.28-7.59(m,9H),1.52(s,6H).
The synthesis of compound 19
Intermediate 19-1 (2.1g, 4.8mmol) is added, intermediate 18-2 (2.4g in single port flask, 4.8mmol), potash (3g), tetra-triphenylphosphine palladium (30mg), oxolane (20mL), water (11mL), is heated to 80 DEG C of reaction 24h, cooling, with dichloromethane extraction, with anhydrous sodium sulfate drying, concentrate and obtain thick product, product 1.64g is being obtained, productive rate 47% through column chromatography for separation.
1h NMR (400MHz, CDCl
3): δ 8.86-8.88 (d, J=7.6Hz, 1H), 8.74-8.76 (d, J=8.0Hz, 1H), 8.69-8.71 (d, J=8.4Hz, 1H), 8.51 (s, 1H), 8.26-8.28 (d, J=8.4Hz, 1H), 7.89-7.90 (d, J=7.2Hz, 1H), 7.81-7.83 (d, J=7.6Hz, 1H), 7.01-7.76 (m, 24H). the hydrogen nuclear magnetic spectrogram of compound 19 is shown in Fig. 2.
Embodiment 3
The preparation of organic electroluminescence device
The compound 19 of embodiment 2 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, the HAT-CN that evaporation 5nm is thick on ITO is hole injection layer 130
Then, evaporation TAPC, forms the hole transmission layer 140 that 65nm is thick.
Then, hole transmission layer steams and crosses the thick luminescent layer of 10nm 150, wherein, compound 19 is main body luminescent material, and the guest materials that adulterates using the Ir of 7% weight ratio (ppy) 2acac as phosphorescence.
Then, the TmPyPB that evaporation 50nm is thick on luminescent layer is as electron transfer layer 160.
Finally, evaporation 1nm LiF is that electron injecting layer 170 and 100nm Al are as device cathodes 180.
Prepared device (structural representation is shown in Fig. 3) records at 100mA/cm with Photo Research PR650 spectrometer
2drive current under power efficiency be 21lm/W, be green spectral.
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, the HAT-CN that evaporation 5nm is thick on ITO is hole injection layer 130
Then, evaporation TAPC, forms the hole transmission layer 140 that 65nm is thick.
Then, hole transmission layer steams and crosses the thick luminescent layer 150 of 10nm, wherein, Compound C BP is main body luminescent material, and with the Ir of 7% weight ratio (ppy)
2acac to adulterate guest materials as phosphorescence.
Then, the TmPyPB that evaporation 50nm is thick on luminescent layer is as electron transfer layer 160.
Finally, evaporation 1nm LiF is that electron injecting layer 170 and 100nm Al are as device cathodes 180.
Prepared device (structural representation is shown in Fig. 3) records at 100mA/cm with Photo Research PR650 spectrometer
2drive current under power efficiency be 16lm/W, be green spectral.
Under identical drive-current condition, the power efficiency of organic electroluminescence device prepared by the phosphorescent light body material applying carbazole derivates of the present invention is higher than comparative example, as mentioned above, compound of the present invention has high stability, and the organic electroluminescence device of preparation has high efficiency and optical purity.
The structural formula of compound described in device is as follows:
。
Claims (9)
1. an organic electroluminescence device, it comprises anode, negative electrode and organic layer, it is one or more layers that organic layer comprises in hole injection layer, hole transmission layer, luminescent layer, barrier layer, electron injecting layer and electron transfer layer, it is characterized in that in organic layer, at least one deck includes the compound based on carbazole derivates of following structural formula (I):
Wherein L is sky, singly-bound, the substituted or unsubstituted alkyl of C1-C8, the substituted or unsubstituted aryl of C6-C30, the replacement of C3-C30 or unsubstituted heteroaryl;
Wherein X
1and X
2be expressed as CH or N independently;
Wherein Ar
1be selected from the substituted or unsubstituted alkyl of C1-C12, the replacement of C6-C60 or unsubstituted aryl, the replacement of C3-C60 or unsubstituted heteroaryl, the replacement of C2-C8 or unsubstituted thiazolinyl, the replacement of C2-C8 or unsubstituted alkynyl;
Wherein Ar
2be selected from following structural:
Wherein A, B, C, D, E and F are independently selected from O, S, NAr
3or CAr
4ar
5;
Wherein, Ar
3, Ar
4and Ar
5separately be selected from the substituted or unsubstituted alkyl of C1-C8, the alkoxyl 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.
2. organic electroluminescence device according to claim 1, is characterized in that wherein
The phenyl that L is selected from phenyl, replaced by C1-C4 alkyl, naphthyl, the naphthyl replaced by C1-C4 alkyl, xenyl or the xenyl replaced by C1-C4 alkyl;
Ar
1, Ar
3, Ar
4and Ar
5separately be selected from the alkyl of C1-C8, the alkoxyl of C1-C8, phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylene base, fluoranthene base, (9,9-dialkyl group) fluorenyl, (9,9-bis-replaces or unsubstituted aryl) fluorenyl, 9,9-Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinolyl, triaromatic amine base, carbazyl;
Wherein above-mentioned phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylene base, fluoranthene base, (9,9-dialkyl group) fluorenyl, (9,9-bis-replaces or unsubstituted aryl) fluorenyl, 9,9-Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinolyl can further replace by the aryl of the alkyl of C1-C4 or C6-C30.
3. organic electroluminescence device according to claim 1 and 2, is characterized in that wherein
L is selected from phenyl, naphthyl, xenyl;
Wherein Ar
1, Ar
3, Ar
4and Ar
5be selected from methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, by the substituted or unsubstituted following aryl of C1-C4 alkyl and heteroaryl:
4. organic electroluminescence device according to claim 1, wherein the compound based on carbazole derivates of structural formula (I) is the compound of following structural 1-30:
5. organic electroluminescence device according to claim 1, is characterized in that the layer at the compound place based on carbazole derivates as described in structural formula (I) is luminescent layer.
6. organic electroluminescence device according to claim 1, is characterized in that the compound based on carbazole derivates as described in structural formula (I) can be used alone, also can use with other compound.
7. organic electroluminescence device according to claim 1, the compound based on carbazole derivates that it is characterized in that 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.
8. organic electroluminescence device according to claim 1, it comprises anode, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, it is characterized in that the compound based on carbazole derivates containing structural formula (I) in luminescent layer.
9. organic electroluminescence device according to claim 8, the compound that it is characterized in that in luminescent layer is the compound of structural formula 1-30.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510080324.5A CN104617224B (en) | 2015-02-14 | 2015-02-14 | Organic electroluminescence device |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107840841A (en) * | 2017-11-02 | 2018-03-27 | 上海道亦化工科技有限公司 | A kind of carbazole pyridine derivate and application thereof and organic electroluminescence device |
| CN107880055A (en) * | 2016-09-30 | 2018-04-06 | 南京高光半导体材料有限公司 | A kind of blue-fluorescence dopant and the organic electroluminescence device comprising this material |
| CN108623480A (en) * | 2017-03-17 | 2018-10-09 | 吉林奥来德光电材料股份有限公司 | New organic luminescent compounds and use its organic electroluminescence device |
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| CN102190627A (en) * | 2010-12-10 | 2011-09-21 | 吉林大学 | 9,10-phenanthroimidazole derivatives and use thereof as electroluminescent materials |
| KR20140008024A (en) * | 2012-07-10 | 2014-01-21 | 에스에프씨 주식회사 | Aromatic compound and organic light-emitting diode comprising the compound |
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| CN102190627A (en) * | 2010-12-10 | 2011-09-21 | 吉林大学 | 9,10-phenanthroimidazole derivatives and use thereof as electroluminescent materials |
| KR20140008024A (en) * | 2012-07-10 | 2014-01-21 | 에스에프씨 주식회사 | Aromatic compound and organic light-emitting diode comprising the compound |
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| CN108623480A (en) * | 2017-03-17 | 2018-10-09 | 吉林奥来德光电材料股份有限公司 | New organic luminescent compounds and use its organic electroluminescence device |
| CN107840841A (en) * | 2017-11-02 | 2018-03-27 | 上海道亦化工科技有限公司 | A kind of carbazole pyridine derivate and application thereof and organic electroluminescence device |
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