CN105218541A - A kind of phosphorescence host compound and organic electroluminescence device thereof - Google Patents
A kind of phosphorescence host compound and organic electroluminescence device thereof Download PDFInfo
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Abstract
The invention provides a kind of phosphorescence host compound as structural formula I, this compound has good thermostability, high-luminous-efficiency, high luminance purity, may be used for being manufactured with organic electroluminescence devices, be applied to organic solar batteries, OTFT or organophotoreceptorswith field.Present invention also offers a kind of 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, and in organic layer, at least one deck includes the compound as structural formula I.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, be specifically related to a kind of phosphorescence host 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, and 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 phosphorescence host compound, and it is the compound with following structural formula I:
Wherein, Ar
1~ Ar
3separately be selected from hydrogen, deuterium, 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;
L is selected from the substituted or unsubstituted aryl of C6-C30, the replacement of C3-C30 or unsubstituted heteroaryl;
Z
1~ Z
4be separately CH or N, wherein have at least one to be N;
Z
5~ Z
7be separately CH or N, wherein have at least one to be N.
Wherein, a kind of preferred mode is:
Ar
1~ Ar
3separately be selected from hydrogen, the alkyl of C1-C8, the alkoxyl group of C1-C8, phenyl, naphthyl, xenyl, fluorenyl, dibenzofuran group, dibenzothiophene base, pyridyl, pyrimidyl, tolyl, phenanthryl, benzo phenanthryl, thienyl, furyl, quinolyl, or more aryl replaced by C1-C4 alkyl further;
L is selected from phenyl, xenyl.
Further preferably, phosphorescence host compound of the present invention is the compound of following structural 1-26:
Phosphorescence host compound of the present invention can be prepared by Suzuki linked reaction, Buchwald-Hartwig reaction and ullmann reaction.
Phosphorescence host compound 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 phosphorescence host compound described in structural formula I in wherein said organic layer:
Wherein Ar
1-Ar
3, Z
1~ R
7and the definition of L as previously mentioned.
Organic layer is wherein had to be 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;
Or organic layer is hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer and electron transfer layer;
Or organic layer is hole injection layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer and electron injecting layer;
Or organic layer is hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer and electron transfer layer;
Or organic layer is hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer and electron injecting layer;
Preferably, the layer at the phosphorescence host compound place wherein as described in structural formula I is luminescent layer;
Preferably, the phosphorescence host compound wherein as described in structural formula I is the compound of structural formula 1-26.
When phosphorescence host compound as described in structural formula I is prepared for luminescent device, can be used alone, also can use with other compound; Phosphorescence host 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 transmission layer, electronic barrier layer, luminescent layer, hole blocking 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 1-26 in luminescent layer.
Preferably, the luminescent layer of organic electroluminescence device contains compound and the phosphorescence light emitting guest material of structural formula I, and wherein Compounds of structural formula I is as material of main part, and its concentration is the 20-99.9% of whole luminescent layer weight, 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 on hole blocking layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and 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 phosphorescence host compound of the present invention as described in structural formula I, has good thermostability, high-luminous-efficiency, high luminance purity.The organic electroluminescence device adopting this phosphorescence host compound 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 mass spectrum of compound 2;
Fig. 2 is the mass spectrum of compound 9;
Fig. 3 is the mass spectrum of compound 19;
Fig. 4 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, 140 are represented as electronic barrier layer, and 150 are represented as luminescent layer, and 160 are represented as hole blocking layer, 170 are represented as electron transfer layer, and 180 are represented as electron injecting layer, and 190 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 2
The synthesis of intermediate 2-1
In there-necked flask, add 9H-pyridine [3,4-b] indoles (2.0g, 12mmol) and DMF (30ml), then slowly add N-bromo-succinimide (2.3g, 13mmol).React 12 hours under room temperature, then add water, filter, by recrystallizing methanol, obtain 2.3g product, productive rate is 80%.
The synthesis of intermediate 2-2
In single port flask, add intermediate 2-1 (2.0g, 8.1mmol), iodobenzene (1.7g, 8.3mmol), potassium hydroxide (0.9g, 16.2mmol), cuprous iodide (0.4g, 0.2mmol), phenanthroline (0.36,0.2mmol) and 30 milliliters of o-Xylols.Under nitrogen protection, reactant reflux 12 hours, cooling, except desolventizing, thick product obtains 1.1g through column chromatography purification, productive rate 43%.
The synthesis of intermediate 2-3
In single port flask; add intermediate 2-2 (1.5g; 4.7mmol), (9H-carbazole-3-base) pinacol borate (1.1g; 5.2mmol), salt of wormwood (1.3g; 9.4mmol), the adjacent palladium (50mg) of water (10mL), tetrahydrofuran (THF) (20mL) and four triphenyls; reflux 12 hours under nitrogen protection; cooling; with dichloromethane extraction; dry; concentrated, thick product obtains 1.4g through column chromatography for separation, productive rate 76%.
The synthesis of compound 2
In flask, add intermediate 2-3 (0.5g, 1.2mmol), 4-(4-bromophenyl)-2; 6-phenylbenzene pyridine (0.46; g, 1.2mmol), the o-Xylol of potassium tert.-butoxide (0.27g, 2.4mmol), palladium (20mg), X-phos (60mg) and 20ml; reflux 10 hours under nitrogen protection; cooling, concentrated, thick product obtains 0.61g through column chromatography purification; product is 71%, and mass spectrum is as Fig. 1.
Embodiment 2
The synthesis of compound 9
The synthesis of compound 9 is the same with the synthesis technique of compound 2, and except replacing outside 4-(4-bromophenyl)-2,6-phenylbenzene pyridine with compound 4-(4-bromophenyl)-2,6-diphenylpyrimidin, productive rate is 69%, and mass spectrum is as Fig. 2.
Embodiment 3
The synthesis of compound 19
The synthesis of compound 19 is the same with the synthesis technique of compound 2, and except replacing outside 4-(4-bromophenyl)-2,6-phenylbenzene pyridine with compound 2-(4-bromophenyl)-4,6-phenylbenzene-1,3,5-triazines, productive rate is 72%, and mass spectrum is as Fig. 3.
Embodiment 4
The synthesis of compound 23
The synthesis of compound 23 is the same with the synthesis technique of compound 2, except with compound 2-(3-bromophenyl)-4,6-phenylbenzene-1,3,5-triazine replaces outside 4-(4-bromophenyl)-2,6-phenylbenzene pyridine, productive rate is 65%, and mass spectrum is 717.2785.
Embodiment 5
The preparation of organic electroluminescence device
The compound 2 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 2-TNATA that evaporation 60nm is thick on ITO is hole transmission layer 130.
Then, evaporation TCTA, forms the electronic barrier layer 140 that 10nm is thick.
Then, the luminescent layer 150 that evaporation 25nm is thick on electronic barrier layer; Wherein, compound 2 is main body luminescent material, and the guest materials that adulterates using the RD of 8% weight ratio as phosphorescence.
Then, the TPBi that evaporation 10nm is thick on luminescent layer is as hole blocking layer 160.
Then, the Bphen that evaporation 30nm is thick on luminescent layer is as electron transfer layer 170.
Finally, evaporation 1nmLiF is that electron injecting layer 180 and 80nmAl are as device cathodes 190.
Prepared device (structural representation is shown in Fig. 4) records at 100mA/cm with PhotoResearchPR650 spectrograph
2current density under external quantum efficiency be 7.5%.
Embodiment 6
The preparation method of device is the same with embodiment 5, except replacing compound 2 with compound 9.
Prepared device PhotoResearchPR650 spectrograph records at 100mA/cm
2current density under external quantum efficiency be 7.8%.
Embodiment 7
The preparation method of device is the same with embodiment 5, except replacing compound 2 with compound 19.
Prepared device PhotoResearchPR650 spectrograph records at 100mA/cm
2current density under external quantum efficiency be 8.1%.
Embodiment 8
The preparation method of device is the same with embodiment 5, except replacing compound 2 with compound 23.
Prepared device PhotoResearchPR650 spectrograph records at 100mA/cm
2current density under external quantum efficiency be 8.0%.
Comparative example
Prepared device is the same with embodiment 5, except replacing compound 2 with Compound C BP.
Prepared device PhotoResearchPR650 spectrograph records at 100mA/cm
2current density under external quantum efficiency be 5.2%.
Under identical current density, apply the current efficiency of organic electroluminescence device prepared by compound of the present invention and external quantum efficiency all 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:
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. a phosphorescence host compound, is characterized in that it is the compound with following structural formula I:
Wherein, Ar
1~ Ar
3separately be selected from hydrogen, deuterium, 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;
L is selected from the substituted or unsubstituted aryl of C6-C30, the replacement of C3-C30 or unsubstituted heteroaryl;
Z
1~ Z
4be separately CH or N, wherein have at least one to be N;
Z
5~ Z
7be separately CH or N, wherein have at least one to be N.
2. phosphorescence host compound according to claim 1, is characterized in that wherein,
Ar
1~ Ar
3separately be selected from hydrogen, the alkyl of C1-C8, the alkoxyl group of C1-C8, phenyl, naphthyl, xenyl, fluorenyl, dibenzofuran group, dibenzothiophene base, pyridyl, pyrimidyl, tolyl, phenanthryl, benzo phenanthryl, thienyl, furyl, quinolyl, or more aryl replaced by C1-C4 alkyl further;
L is selected from phenyl, xenyl.
3. phosphorescence host compound as claimed in claim 1, is characterized in that it is the compound of following structural 1-26:
4. 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 having at least one deck to include phosphorescence host compound as claimed in claim 1 in described organic layer.
5. organic electroluminescence device according to claim 4, is characterized in that the layer at the phosphorescence host compound place as described in structural formula I is luminescent layer.
6. organic electroluminescence device according to claim 4, is characterized in that the phosphorescence host compound as described in structural formula I is used alone, or and other compound use.
7. organic electroluminescence device according to claim 4, the phosphorescence host 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.
8. organic electroluminescence device according to claim 4, it comprises anode, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer and negative electrode, it is characterized in that the compound containing one or more structural formulas I in luminescent layer.
9. organic electroluminescence device according to claim 4, it comprises anode, hole transmission layer, luminescent layer, electron transfer layer and negative electrode, it is characterized in that the compound containing one or more structural formulas 1-26 in luminescent layer.
10. organic electroluminescence device according to claim 4, it is characterized in that luminescent layer contains compound and the phosphorescence light emitting guest material of structural formula I, wherein Compounds of structural formula I is as material of main part, and its concentration is the 20-99.9% of whole luminescent layer weight.
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| WO2019066250A1 (en) * | 2017-09-29 | 2019-04-04 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using same, and electronic device comprising same |
| CN111164079A (en) * | 2017-09-29 | 2020-05-15 | 德山新勒克斯有限公司 | Compound for organic electric element, organic electric element using same, and electronic device using same |
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| US20140225088A1 (en) * | 2013-02-12 | 2014-08-14 | Cheil Industries Inc. | Compound for organic optoelectronic device, organic light emitting diode including the same, and display including the organic light emitting diode |
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