CN105061439A - Organic electroluminescent compound and organic electroluminescent device thereof - Google Patents
Organic electroluminescent compound and organic electroluminescent device thereof Download PDFInfo
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- CN105061439A CN105061439A CN201510481891.1A CN201510481891A CN105061439A CN 105061439 A CN105061439 A CN 105061439A CN 201510481891 A CN201510481891 A CN 201510481891A CN 105061439 A CN105061439 A CN 105061439A
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- 0 *1c(cccc2)c2C2=CC=CCC12 Chemical compound *1c(cccc2)c2C2=CC=CCC12 0.000 description 1
- NDKLHGIKOMUGPE-UHFFFAOYSA-N C(C12)C=CC=C1c(cc(cc1)-c3c4[s]c5ccccc5c4ccc3)c1N2c1cc(-c2nccc3c2c(cccc2)c2[s]3)ccc1 Chemical compound C(C12)C=CC=C1c(cc(cc1)-c3c4[s]c5ccccc5c4ccc3)c1N2c1cc(-c2nccc3c2c(cccc2)c2[s]3)ccc1 NDKLHGIKOMUGPE-UHFFFAOYSA-N 0.000 description 1
- FUVMKKHFNMJZIR-UHFFFAOYSA-N OB(c1cccc(-[n]2c(ccc(-c3cccc4c3[o]c3c4cccc3)c3)c3c3c2cccc3)c1)O Chemical compound OB(c1cccc(-[n]2c(ccc(-c3cccc4c3[o]c3c4cccc3)c3)c3c3c2cccc3)c1)O FUVMKKHFNMJZIR-UHFFFAOYSA-N 0.000 description 1
- RPWTWYRTWSEUEP-UHFFFAOYSA-N c(cc1c2c3ccc(-c4c5[s]c(cccc6)c6c5ccc4)c2)ccc1[n]3-c(cc1)ccc1-c1ccc(c2cccnc2[o]2)c2c1 Chemical compound c(cc1c2c3ccc(-c4c5[s]c(cccc6)c6c5ccc4)c2)ccc1[n]3-c(cc1)ccc1-c1ccc(c2cccnc2[o]2)c2c1 RPWTWYRTWSEUEP-UHFFFAOYSA-N 0.000 description 1
- QWLJBHTXFVNNIK-UHFFFAOYSA-N c(cc1c2c3ccc(-c4c5[s]c(cccc6)c6c5ccc4)c2)ccc1[n]3-c(cc1)ccc1-c1ncc(c(cccc2)c2[s]2)c2c1 Chemical compound c(cc1c2c3ccc(-c4c5[s]c(cccc6)c6c5ccc4)c2)ccc1[n]3-c(cc1)ccc1-c1ncc(c(cccc2)c2[s]2)c2c1 QWLJBHTXFVNNIK-UHFFFAOYSA-N 0.000 description 1
- JFXDOKDYWQAQSR-UHFFFAOYSA-N c(cc1c2c3ccc(-c4c5[s]c(cccc6)c6c5ccc4)c2)ccc1[n]3-c1cc(-c2ncc(c3ccccc3[s]3)c3c2)ccc1 Chemical compound c(cc1c2c3ccc(-c4c5[s]c(cccc6)c6c5ccc4)c2)ccc1[n]3-c1cc(-c2ncc(c3ccccc3[s]3)c3c2)ccc1 JFXDOKDYWQAQSR-UHFFFAOYSA-N 0.000 description 1
- GGQPQPWHVWBPLI-UHFFFAOYSA-N c(cc1c2c3ccc(-c4c5[s]c6ccccc6c5ccc4)c2)ccc1[n]3-c(cc1)ccc1-c(cc1)cc2c1c(cncc1)c1[o]2 Chemical compound c(cc1c2c3ccc(-c4c5[s]c6ccccc6c5ccc4)c2)ccc1[n]3-c(cc1)ccc1-c(cc1)cc2c1c(cncc1)c1[o]2 GGQPQPWHVWBPLI-UHFFFAOYSA-N 0.000 description 1
- PFGVANAAERAPTF-UHFFFAOYSA-N c(cc1c2c3ccc(-c4c5[s]c6ccccc6c5ccc4)c2)ccc1[n]3-c(cc1)ccc1-c1nccc2c1c(cccc1)c1[s]2 Chemical compound c(cc1c2c3ccc(-c4c5[s]c6ccccc6c5ccc4)c2)ccc1[n]3-c(cc1)ccc1-c1nccc2c1c(cccc1)c1[s]2 PFGVANAAERAPTF-UHFFFAOYSA-N 0.000 description 1
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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Abstract
The present invention provides a novel organic electroluminescent compound as shown in formula I. With good thermal stability, high luminous efficiency, and high luminous purity, the compound can be used to manufacture an organic electroluminescent device applying to the field of an organic solar cell, an organic thin film transistor or an organic photoreceptor. The present invention also provides an organic electroluminescent device. The device comprises an anode, a cathode and an organic layer, wherein the organic layer comprises one or more of a light emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer, and an electron transport layer. At least one layer of the organic layer contains the compound as showm in formula I. The formula I is as shown in the specification.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, be specifically related to a kind of novel electroluminescent compound and organic electroluminescence device thereof, belong to organic electroluminescence device technique of display field.
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, therefore needs the efficiency improving device.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.
Organic electrophosphorescenpolymer phenomenon, breaches organic electroluminescent quantum yield lower than the theory restriction of 25%, rises to 100% (BaldoM.A., ForrestS.R.Etal, 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 novel organic electroluminescent compounds, and it is the compound with following structural formula I:
Wherein, L
1and L
2separately be selected from singly-bound, the replacement of C6-C30 or unsubstituted aryl, the replacement of C3-C30 or the unsubstituted heteroatomic aryl containing one or more;
Z
1-Z
8in have one for N, all the other are CH;
A and B is separately selected from O, S, SO, SO
2, Se, CR
1r
2;
R
1and R
2separately be selected from C1-C8 alkoxyl group, the replacement of C6-C30 or unsubstituted aryl, the replacement of C3-C30 or unsubstituted containing one or more heteroatomic aryl.
Preferably, L
1and L
2separately be selected from singly-bound, phenyl, naphthyl, pyridyl, quinolyl, xenyl, fluorenyl, dibenzothiophene base, dibenzofuran group, carbazyl, benzimidazolyl-, benzothiazolyl, pyrimidyl, benzothiazolyl, oxazolyl, thiazolyl;
A and B is separately selected from O, S.
More preferably, L
1and L
2separately be selected from singly-bound, phenyl, naphthyl, xenyl.
Further preferably, novel electroluminescent compound of the present invention is the compound of following structural 1-36:
Novel cpd 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, electron transfer layer, has one deck at least containing, for example the novel cpd described in structural formula I in wherein said organic layer:
Wherein L
1-L
2, Z
1-Z
8, A and B definition 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, blocking 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.
Preferably, the layer at the novel cpd place wherein as described in structural formula I is luminescent layer;
Preferably, the novel cpd wherein described in structural formula I is the compound of structural formula 1-36;
When compound as described in structural formula I is prepared for luminescent device, can be used alone, also can use with other compound; Compound 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; Further preferably, the compound containing one or more structural formula 1-36 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 the compound of structural formula I is as material of main part, its concentration is the 20-99.9% of whole luminescent layer weight, and preferred 80-99%, is more preferably 90-99%.
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, can to arrange in pairs or groups use other materials, as medium at hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and hole blocking layer, 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.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 material, phosphorescence light emitting guest material can comprise the organometallic 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 electronic 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 heterocyclic compound, quinolines, phenanthroline compounds, metallo-chelate are (as Alq
3), 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 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: the oxide compound of basic metal, alkaline-earth metal, rare earth metal, alkali-metal oxide compound or halogenide, alkaline-earth metal or halogenide, the oxide compound of rare earth metal or the organic complex of halogenide, 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 material 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 novel cpd 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 novel cpd 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 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.
Embodiment 1
The synthesis of compound 1
The synthesis of intermediate 1-1
In there-necked flask; add 3-bromine carbazole (24.5g, 0.1mol), 4-diphenylene-oxide boric acid (21.2g, 0.1mol), salt of wormwood (27.2g; 0.2mol), 300ml tetrahydrofuran (THF), 100ml water and tetra-triphenylphosphine palladium (0.5g); reflux 12 hours under nitrogen protection, cooling, is extracted with ethyl acetate; dry; concentrated, thick product recrystallizing methanol obtains 30.6g product, and productive rate is 92%.
The synthesis of intermediate 1-2
In there-necked flask; add intermediate 1-1 (25g; 0.075mol), a bromo-iodobenzene (28.1g; 0.1mol), potassium hydroxide (5.6g; 0.1mol), cuprous iodide (1.9g), phenanthroline (2.5g) and 300ml sym-trimethylbenzene; reflux 24 hours under nitrogen protection; cooling; removal of solvent under reduced pressure, adds water and methylene dichloride, layering; organic phase anhydrous sodium sulfate drying; concentrated, thick product column chromatography purification obtains 29.2g product, and productive rate is 80%.
The synthesis of intermediate 1-3
In there-necked flask, add intermediate 1-2 (15g, 0.031mol), the tetrahydrofuran (THF) of 180ml drying,-78 are cooled to spend, under nitrogen protection, hexane solution (the 15ml of the n-Butyl Lithium of slow dropping 2.5M, 0.037mmol), react 2 hours at this temperature, then triisopropyl borate ester (8.7g is slowly added, 0.046mol), drip off, slowly rise to room temperature reaction 12 hours, the dilute hydrochloric acid solution of slow dropping 1N, be extracted with ethyl acetate, use anhydrous sodium sulfate drying again, concentrated, 9.1g product is obtained with ether and normal hexane recrystallization, productive rate is 65%.
The synthesis of compound 1
In there-necked flask, add the chloro-cumarone [3 of intermediate 1-3 (2.5g, 5.5mmol), 3-; 2-c] pyridine (1.2g; 5.9mmol), salt of wormwood (1.5g, 11mmol), 30ml tetrahydrofuran (THF), 10ml water and tetra-triphenylphosphine palladium (50mg), under nitrogen protection reflux 12 hours; cooling; with dichloromethane extraction, dry, concentrated; thick product column chromatography for separation obtains 2.5g product, and productive rate is 78%.
Embodiment 2
The synthesis of compound 9
In there-necked flask, add the chloro-thionaphthene [3 of intermediate 1-3 (2.5g, 5.5mmol), 3-; 2-c] pyridine (1.3g; 6.0mmol), salt of wormwood (1.5g, 11mmol), 30ml tetrahydrofuran (THF), 10ml water and tetra-triphenylphosphine palladium (50mg), under nitrogen protection reflux 12 hours; cooling; with dichloromethane extraction, dry, concentrated; thick product column chromatography for separation obtains 2.4g product, and productive rate is 73%.
Embodiment 3
The synthesis of compound 19
The synthesis of intermediate 19-1
In there-necked flask; add 3-bromine carbazole (24.5g, 0.1mol), 4-diphenylene-oxide boric acid (22.8g, 0.1mol), salt of wormwood (27.2g; 0.2mol), 300ml tetrahydrofuran (THF), 100ml water and tetra-triphenylphosphine palladium (0.5g); reflux 12 hours under nitrogen protection, cooling, is extracted with ethyl acetate; dry; concentrated, thick product recrystallizing methanol obtains 31g product, and productive rate is 89%.
The synthesis of intermediate 19-2
In there-necked flask; add intermediate 19-1 (25g; 0.072mol), a bromo-iodobenzene (28.1g; 0.1mol); potassium hydroxide (5.6g; 0.1mol), cuprous iodide (1.9g), phenanthroline (2.5g) and 300ml sym-trimethylbenzene; reflux 24 hours under nitrogen protection, cooling, removal of solvent under reduced pressure; add water and methylene dichloride; layering, organic phase anhydrous sodium sulfate drying, concentrated; thick product column chromatography purification obtains 26.1g product, and productive rate is 72%.
The synthesis of intermediate 19-3
In there-necked flask, add intermediate 19-2 (15g, 0.030mol), the tetrahydrofuran (THF) of 180ml drying,-78 are cooled to spend, under nitrogen protection, hexane solution (the 15ml of the n-Butyl Lithium of slow dropping 2.5M, 0.037mmol), react 2 hours at this temperature, then triisopropyl borate ester (8.7g is slowly added, 0.046mol), drip off, slowly rise to room temperature reaction 12 hours, the dilute hydrochloric acid solution of slow dropping 1N, be extracted with ethyl acetate, use anhydrous sodium sulfate drying again, concentrated, 10g product is obtained with ether and normal hexane recrystallization, productive rate is 71%.
The synthesis of compound 19
In there-necked flask, add the chloro-cumarone [3 of intermediate 19-3 (2.5g, 5.3mmol), 3-; 2-c] pyridine (1.2g; 5.9mmol), salt of wormwood (1.5g, 11mmol), 30ml tetrahydrofuran (THF), 10ml water and tetra-triphenylphosphine palladium (50mg), under nitrogen protection reflux 12 hours; cooling; with dichloromethane extraction, dry, concentrated; thick product column chromatography for separation obtains 2.6g product, and productive rate is 82%.
Embodiment 4
The synthesis of compound 27
In there-necked flask, add the chloro-thionaphthene [3 of intermediate 19-3 (2.5g, 5.3mmol), 3-; 2-c] pyridine (1.3g; 6.0mmol), salt of wormwood (1.5g, 11mmol), 30ml tetrahydrofuran (THF), 10ml water and tetra-triphenylphosphine palladium (50mg), under nitrogen protection reflux 12 hours; cooling; with dichloromethane extraction, dry, concentrated; thick product column chromatography for separation obtains 2.7g product, and productive rate is 85%.
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, 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 1 is main body luminescent material, and the guest materials that adulterates using 7%Ir (ppy) 2acac as phosphorescence.
Then, the TmPyPB that evaporation 50nm is thick on luminescent layer is as electron transfer layer 160.
Finally, evaporation 1nmLiF is that electron injecting layer 170 and 100nmAl are as device cathodes 180.
Prepared device (structural representation is shown in Fig. 1) records at 100mA/cm with PhotoResearchPR650 spectrograph
2current density under driving voltage be 5.6V, be green spectral.
Embodiment 6
The method of fabricate devices is the same with embodiment 5, except replacing compound 1 with compound 9.
Prepared device PhotoResearchPR650 spectrograph records at 100mA/cm
2current density under driving voltage be 5.7V, be green spectral.
Embodiment 7
The method of fabricate devices is the same with embodiment 5, except replacing compound 1 with compound 19.
Prepared device PhotoResearchPR650 spectrograph records at 100mA/cm
2current density under driving voltage be 5.8V, be green spectral.
Embodiment 8
The method of fabricate devices is the same with embodiment 5, except replacing compound 1 with compound 27.
Prepared device PhotoResearchPR650 spectrograph records at 100mA/cm
2current density under driving voltage be 5.5V, be green spectral.
Comparative example
The method of fabricate devices is the same with embodiment 5, except replacing compound 1 with Compound C BP.
Prepared device PhotoResearchPR650 spectrograph records at 100mA/cm
2current density under driving voltage be 6.7V, be green spectral.
Verified, novel organic electroluminescent compounds of the present invention has more excellent photoelectric property than conventional material, and the organic electroluminescence device prepared by the present invention has high efficiency and optical purity.
The structural formula of compound described in device is as follows:
More than describe preferred embodiment of the present invention in detail.Should be appreciated that the ordinary skill of this area just design according to the present invention can make many modifications and variations without the need to creative work.Therefore, all technician in the art, all should by the determined protection domain of claims under this invention's idea on the basis of existing technology by the available technical scheme of logical analysis, reasoning, or a limited experiment.
Claims (10)
1. an organic electroluminescent compounds, is characterized in that it is the compound with following structural formula I:
Wherein, L
1and L
2separately be selected from singly-bound, the replacement of C6-C30 or unsubstituted aryl, the replacement of C3-C30 or the unsubstituted heteroatomic aryl containing one or more;
Z
1-Z
8in have one for N, all the other are CH;
A and B is separately selected from O, S, SO, SO
2, Se, CR
1r
2;
R
1and R
2separately be selected from C1-C8 alkoxyl group, the replacement of C6-C30 or unsubstituted aryl, the replacement of C3-C30 or unsubstituted containing one or more heteroatomic aryl.
2. organic electroluminescent compounds according to claim 1, is characterized in that wherein,
L
1and L
2separately be selected from singly-bound, phenyl, naphthyl, pyridyl, quinolyl, xenyl, fluorenyl, dibenzothiophene base, dibenzofuran group, carbazyl, benzimidazolyl-, benzothiazolyl, pyrimidyl, benzothiazolyl, oxazolyl, thiazolyl;
A and B is separately selected from O, S.
3. organic electroluminescent compounds according to claim 1 and 2, is characterized in that, wherein L
1and L
2separately be selected from singly-bound, phenyl, naphthyl, xenyl.
4. organic electroluminescent compounds as claimed in claim 1, is characterized in that it is the compound of following structural 1-36:
5. an organic electroluminescence device, it 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, electron transfer layer, it is characterized in that in organic layer, at least one deck includes organic electroluminescent compounds as claimed in claim 1.
6. organic electroluminescence device according to claim 5, is characterized in that the layer at the organic electroluminescent compounds place as described in structural formula I is luminescent layer.
7. organic electroluminescence device according to claim 5, is characterized in that the organic electroluminescence compound as described in structural formula I is used alone, or and other compound use.
8. organic electroluminescence device according to claim 5, the organic electroluminescence compound that it is characterized in that as described in structural formula I is used alone a kind of compound wherein, or uses two or more the compound in structural formula I simultaneously.
9. organic electroluminescence device according to claim 5, it comprises anode, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, it is characterized in that the compound containing one or more structural formula I in luminescent layer.
10. organic electroluminescence device according to claim 5, it comprises anode, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, it is characterized in that the compound containing one or more structural formula 1-36 in luminescent layer.
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