CN104167498B - A kind of organic electroluminescence device - Google Patents

A kind of organic electroluminescence device Download PDF

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CN104167498B
CN104167498B CN201410414995.6A CN201410414995A CN104167498B CN 104167498 B CN104167498 B CN 104167498B CN 201410414995 A CN201410414995 A CN 201410414995A CN 104167498 B CN104167498 B CN 104167498B
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compound
organic
electroluminescence device
organic electroluminescence
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CN104167498A (en
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黄锦海
苏建华
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Shanghai Taoe Chemical Technology Co Ltd
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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

Abstract

The invention provides a kind of organic electroluminescence device, it comprises anode, negative electrode and organic layer, organic layer comprises one or more layers 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 that one deck at least includes the compound of following structural formula (I).

Description

A kind of organic electroluminescence device
Technical field
The present invention relates to organic electroluminescent field, relate to specifically a kind of organic electroluminescence device.
Background technology
Organic electroluminescence device (OLEDs) is by spin coating or vacuum evaporation deposition one between two metal electrodesThe device that layer organic material is prepared from, three layers of classical organic electroluminescence device comprise hole transmission layer, luminescent layerAnd electron transfer layer. The hole being produced by anode follows the electronics being produced by negative electrode to be combined in through electron transfer layer through hole transmission layerLuminescent layer forms exciton, then luminous. Organic electroluminescence device can be adjusted by the material that changes luminescent layer as requiredThe light of the various needs of joint transmitting.
Organic electroluminescence device, as a kind of novel Display Technique, has self-luminous, wide visual angle, low energy consumption, efficiencyHigh, thin, rich color, fast response time, Applicable temperature scope are wide, low driving voltage, can make flexible and transparentThe particular advantages such as display floater and environmental friendliness, can be applied in flat-panel monitor and a new generation's illumination is upper, also can be used asThe backlight of LCD.
Since invention at the bottom of the eighties in 20th century, organic electroluminescence device is industrially application to some extent, such asThe factors such as the screen such as camera and mobile phone, but current OLED device is because efficiency is low, and service life is short restrict that it is widerGeneral application, particularly large screen display. Be exactly in organic electroluminescence device and restrict one of them key factorThe performance of electroluminescent organic material. Because OLED device is applying voltage-operated time, can produce Joule heat in addition, makeEasily there is crystallization in organic material, has affected life-span and the efficiency of device, therefore, also needs to develop the organic electroluminescence of stability and high efficiencyLuminescent material.
In OLED material, because the speed of most electroluminescent organic material transporting holes is than the speed of transmission electronicHurry up, easily cause electronics and the number of cavities imbalance of luminescent layer, the efficiency of device is just lower like this. Three (oxines)Aluminium (Alq3) since invention, be extensively studied, but as its electron mobility of electron transport material still veryLow, and the intrinsic characteristic that self can degrade, taking in the device of electron transfer layer, there will be the situation of voltage drop,Meanwhile, due to lower electron mobility, make a large amount of holes enter into Alq3In layer, excessive hole is with non-luminous shapeFormula emittance, and when as electron transport material, due to the characteristic of its green light, in application, be restricted. CauseThis, development stability and have the electron transport material of larger electron mobility, to being widely used of organic electroluminescence deviceThere is great value.
Summary of the invention
First the present invention provides a kind of electric transmission compound based on benzimidazole, and it is to have following structural formula I'sCompound:
Wherein, R1、R2、R3、R4、R5、R6、R7And R8Respectively independently selected from hydrogen, D-atom, halogen, cyano group, nitro, C1-The replacement of the replacement of the alkyl of C8, C1-C8 alkoxyl, C6-C30 or unsubstituted aryl, C3-C30 or unsubstituted assortedThe replacement of the replacement of aryl, C2-C8 or unsubstituted thiazolinyl, C2-C8 or unsubstituted alkynyl;
L1And L2Respectively independently selected from the replacement of the alkyl of sky, singly-bound, C1-C6, C6-C30 or unsubstituted aryl, C3-The replacement of C30 or unsubstituted heteroaryl,
X1And X2Respectively independently selected from O, S, S=O, S (O)2、Se、NAr；
A is selected from O, S, S=O, S (O)2、Se；
Wherein Ar be selected from the replacement of hydrogen, C1-C12 alkyl, C6-C60 or unsubstituted aryl, C3-C60 replacement orUnsubstituted heteroaryl;
Wherein preferred mode is:
R1、R2、R3、R4、R5、R6、R7And R8Respectively independently selected from hydrogen, halogen, cyano group, nitro, C1-C8 alkyl, C1-C8Alkoxyl, phenyl, naphthyl, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinoline;
L1And L2Respectively independently selected from sky, singly-bound, phenyl, the phenyl being replaced by C1-C4 alkyl, naphthyl, by C1-C4 alkaneThe naphthyl that base replaces;
X1And X2Respectively independently selected from O, S, S=O, S (O)2、NAr；
A is selected from O, S, S=O, S (O)2；
Ar is selected from alkyl, phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylene base, fluoranthene base, (9,9-dialkyl group) fluorenes of C1-C8Base, (9,9-bis-replaces or unsubstituted aryl) fluorenyl, 9,9-is Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, pyridineBase, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinolyl;
Wherein above-mentioned phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylene base, fluoranthene base, (9,9-dialkyl group) fluorenyl, (9,9-Two replace or unsubstituted aryl) fluorenyl, 9,9-is Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, pyridine radicals, pyrimidineBase, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinolyl can further be got by the aryl of the alkyl of C1-C4 or C6-C30Generation;
Further preferred mode is:
R1、R2、R3、R4、R5、R6、R7And R8Respectively independently selected from hydrogen, fluorine, nitro, methyl, ethyl, propyl group, isopropyl,The tert-butyl group, normal-butyl, n-hexyl, phenyl, naphthyl;
L1And L2Respectively independently selected from sky, singly-bound, phenyl, naphthyl;
X1And X2Respectively independently selected from O, S, NAr;
A is selected from O and S;
Wherein Ar be selected from that methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, C1-C4 alkyl replace orUnsubstituted following aryl and heteroaryl:
Further preferred, the electric transmission compound based on benzimidazole of the present invention is the change of following structural 1-70Compound.
Electric transmission compound based on benzimidazole of the present invention can prepare by Suzuki coupling reaction.
Electric transmission compound based on benzimidazole of the present invention can be applied in organic electroluminescence device, You JitaiSun can battery, OTFT or organophotoreceptorswith field.
The present invention also provides a kind of organic electroluminescence device, and this device comprises anode, negative electrode and organic layer, organic layerComprise one deck in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer or electron transfer layer orMore than one deck, in wherein said organic layer, have at least one deck to contain just like the electronics based on benzimidazole structural formula (I) Suo Shu and passDefeated compound:
Wherein R1-R8、Ar、A、X1-X2And L1-L2Definition as previously mentioned.
Wherein organic layer is luminescent 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 stopsLayer;
Or organic layer is luminescent layer, hole transmission layer, electron transfer layer, electron injecting layer and barrier layer;
Or organic layer is luminescent layer, hole transmission layer, electron injecting layer and barrier layer;
Wherein the layer at the electric transmission compound place based on benzimidazole as described in structural formula (I) is electron transfer layerOr electron injecting layer;
Wherein the described electric transmission compound based on benzimidazole of structural formula (I) is the compound of structural formula 1-70;
The electric transmission compound based on benzimidazole as described in structural formula I can use separately, also can and otherCompound is used; The electric transmission compound based on benzimidazole as described in structural formula I can use separately whereinA kind of compound also can use two or more the compound in structural formula I simultaneously.
Organic electroluminescence device of the present invention, further preferred mode is that this organic electroluminescence device comprises sunThe utmost point, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, wherein in electron transfer layer or electron injecting layerThe compound that contains structural formula (I); Further preferred, the compound in electron transfer layer or electron injecting layer is structural formulaThe compound of 1-70.
Organic electroluminescence device of the present invention, structural formula I compound also can doublely do electronics during as electron transfer layerImplanted layer.
The gross thickness of organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
Organic electroluminescence device of the present invention, in the time using the present invention to have the compound of structural formula I, can use and takeJoin other materials, as hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and barrier layer etc., andObtain 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 holeTransmission performance, can be transferred to hole luminescent layer from anode effectively. Can comprise that other little molecules and macromolecule are organicCompound, includes but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanineCompounds, the assorted triphen (hexanitrilehexaazatriphenylene), 2,3,5 of six cyano group six, 6-tetrafluoro-7,7', 8,8'-tetra-cyanogen dimethyl 1,4-benzoquinone (F4-TCNQ), PVK, 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 as requiredThe scope of visible ray. Following compound be can contain, naphthalene compounds, pyrene compound, fluorenes class chemical combination included, but are not limited toThing, luxuriant and rich with fragrance compounds, compounds in the wrong, fluoranthene compounds, anthracene compounds, pentacene compounds, perylene compounds, twoAromatic ethylene compounds, triphenylamine ethylene compounds, aminated compounds, carbazole compound, benzimidazoles compound, furanMutter compounds, metal organic fluorescence complex compound, the organic phosphorescence complex compound of metal (as Ir, Pt, Os, Cu), polyvinylcarbazole, poly-The organic polymer luminescent material such as organo-silicon compound, polythiophene, they can use separately, also can make by multiple mixtureWith.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires to have good electronic transmission performance, energyEnough effectively during electronics is from cathode transport to luminescent layer, there is very large electron mobility. Remove the structural formula I that has of the present inventionOutside compound, can also select following compound, but be not limited to this, oxa-oxazole, thiazole compound, triazole chemical combinationThing, three nitrogen piperazine compounds, triazine compounds, quinoline compounds, phenazine compounds, siliceous heterocyclic chemical combinationThing, quinolines, ferrosin compounds, metallo-chelate (as Alq3), fluorine substituted benzene compound, benzimidazoleCompound.
The electron injecting layer of organic electroluminescence device of the present invention, can effectively be injected into organic layer electronics from negative electrodeIn, have structural formula I compound except of the present invention, be mainly selected from alkali metal or alkali-metal compound, or be selected from alkaline earthThe compound of metal or alkaline-earth metal or alkali metal complex, can select following compound, but be not limited to this, alkali goldThe oxide of genus, alkaline-earth metal, rare earth metal, alkali-metal oxide or halide, alkaline-earth metal or halide, rare earthThe organic complex of the oxide of metal or 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,Magnesia, these compounds can use separately also and can use by mixture, also can join with other electroluminescent organic materialsClose use.
Every one deck of organic layer in organic electroluminescence device of the present invention, can pass through vacuum vapour deposition, molecular beam steamingPrepared by the modes such as plating method, the dip coating that is dissolved in solvent, spin-coating method, excellent painting method or inkjet printing. Can make for metal motorBe prepared with vapour deposition method or sputtering method.
Device experimental shows, the electric transmission compound based on benzimidazole of the present invention as described in structural formula (I), hasBetter heat endurance, high-luminous-efficiency, high luminance purity. The organic electroluminescent that adopts this organic electroluminescent compounds to makeDevice have advantages of the good and excitation excellence of electroluminescent efficiency and the life-span long.
Brief description of the drawings
Fig. 1 is the hydrogen nuclear magnetic spectrogram of compound 31.
Fig. 2 is the hydrogen nuclear magnetic spectrogram of compound 51.
Fig. 3 is that compound 31 and compound 51 are 1 × 10 in concentration-5Under the dichloromethane solution of mole every liter, use VarianThe uv-visible absorption spectra that Cary500 ultraviolet-visible spectrophotometer records.
Fig. 4 is that compound 31 and compound 51 are 1 × 10 in concentration-5Under the dichloromethane solution of mole every liter, use VarianThe fluorescence emission spectrum that CaryEclipse sepectrophotofluorometer records.
Fig. 5 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 be represented as send outPhotosphere, 150 are represented as electron transfer layer, and 160 are represented as electron injecting layer, and 170 are represented as negative electrode.
Fig. 6 is that embodiment 3 is at 25mA/cm2Current density under emission spectrum.
Detailed description of the invention
In order more to describe the present invention in detail, especially exemplified by following example, but be not limited to this.
Embodiment 1
Synthesizing of compound 31
Intermediate 31-1's is synthetic
In flask, add the acetic acid of thioxanthones (5.0g, 24mmol) and 45ml, add hot reflux, slowly drip bromine(9.6g, 60mmol), drips off, and adds hot reflux 12 hours, cooling, filters, and obtains 6.2g yellow solid, and productive rate is 70%.1HNMR(400MHz,CDCl3,δ):8.74(s,2H),7.73-7.75(d,J＝8.4Hz,2H),7.46-7.48(d,J＝8.4Hz,2H).
Intermediate 31-2 and intermediate 31-3's is synthetic
In there-necked flask, add magnesium chips (0.32g, 13.5mmol), add the iodine of catalytic amount, slowly drip and be dissolved with 2-bromine15ml oxolane (THF) solution of biphenyl (3g, 13.5mmol), adds hot reflux 2 hours, and cooling, the liquid of gained slowly dripsBe added to the 30ml tetrahydrofuran solution that is dissolved with intermediate 31-1 (2.5g, 6.8mmol), dropwise, reflux 6 hours, cooling,Reactant liquor is poured into water, and is extracted with ethyl acetate three times, merges organic phase, dry, the concentrated intermediate 31-2 that obtains. Past gainedIntermediate 31-2 adds the acetic acid of 30ml, adds hot reflux, drips the concentrated hydrochloric acid of 0.5ml, refluxes 2 hours, and cooling, filtration obtains2.4g white solid, productive rate is 71%.1HNMR(400MHz,CDCl3,δ):7.79-7.81(d,J＝7.6Hz,2H),7.52-7.54(d,J＝7.6Hz,2H),7.41-7.45(m,2H),7.23-7.26(m,6H),6.60(s,2H).
Synthesizing of compound 31
In single port flask, add compound 31-3 (0.25g, 0.5mmol), 4-(1-phenyl-1H-benzimidazolyl-2 radicals-Base) phenyl boric acid (0.4g, 1.24mmol), the THF of 20ml and the 2MK of 8ml2CO3The aqueous solution, under nitrogen protection, adds 10mgFour (triphenyl phosphorus) palladium (0.0075mmol), then adds hot reflux 5 hours, has reacted, cooling, uses dichloromethane extraction three times,Organic layer anhydrous sodium sulfate drying, organic solvent is removed in rotation, and crude product carries out column chromatography purification, obtains 0.42g off-white colorSolid, productive rate is 95%.1HNMR(400MHz,CDCl3,δ):7.85-7.87(d,J＝8.0Hz,2H),7.77-7.79(d,J＝7.6Hz,2H),7.63-7.64(d,J＝7.6Hz,2H),7.20-7.48(m,28H),7.13-7.15(d,J＝8.0Hz,4H),6.75(s,2H).
The hydrogen nuclear magnetic spectrogram of compound 31 is shown in Fig. 1. Compound 31 is 1 × 10 in concentration-5The carrene of mole every liter is moltenThe maximum absorption wavelength recording with VarianCary500 ultraviolet-visible spectrophotometer under liquid is 350nm, and ultraviolet-visible is inhaledReceive spectrum and see Fig. 3, Fig. 4 is that compound 31 is 1 × 10 in concentration-5Under the dichloromethane solution of mole every liter, use VarianCaryThe fluorescence emission spectrum that Eclipse sepectrophotofluorometer records, the maximum emission wavelength recording is 410nm.
Embodiment 2
Synthesizing of compound 51
In single port flask, add compound 31-3 (0.25g, 0.5mmol), 3-(1-phenyl-1H-benzimidazolyl-2 radicals-Base) phenyl boric acid (0.4g, 1.24mmol), the THF of 20ml and the 2MK of 8ml2CO3The aqueous solution, under nitrogen protection, adds 10mgFour (triphenyl phosphorus) palladium (0.0075mmol), then adds hot reflux 5 hours, has reacted, cooling, uses dichloromethane extraction three times,Organic layer anhydrous sodium sulfate drying, organic solvent is removed in rotation, and crude product carries out column chromatography purification, obtains 0.31g off-white colorSolid, productive rate is 70%.1HNMR(400MHz,CDCl3,δ):7.86-7.88(d,J＝7.6Hz,2H),7.77-7.79(d,J＝7.6Hz,2H),7.60-7.62(d,J＝7.6Hz,2H),7.16-7.51(m,28H),7.07-7.10(m,4H),6.70(s,2H).
The hydrogen nuclear magnetic spectrogram of compound 51 is shown in Fig. 2. Compound 51 is 1 × 10 in concentration-5The carrene of mole every liter is moltenThe maximum absorption wavelength recording with VarianCary500 ultraviolet-visible spectrophotometer under liquid is 330nm, and ultraviolet-visible is inhaledReceive spectrum and see Fig. 3, Fig. 4 is that compound 31 is 1 × 10 in concentration-5Under the dichloromethane solution of mole every liter, use VarianCaryThe fluorescence emission spectrum that Eclipse sepectrophotofluorometer records, the maximum emission wavelength recording is 380nm.
Embodiment 3
The preparation of organic electroluminescence device
Use the compound 51 of embodiment 2 to prepare OLED
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (the limited public affairs of South China glass group shareDepartment) warp successively: deionized water, ethanol, acetone and deionized water are cleaned, then use oxygen plasma treatment 30 seconds.
Then, evaporation NPB, forms the thick hole transmission layer 130 of 60nm.
Then the compd A lq that, evaporation 30nm is thick on hole transmission layer3As luminescent layer 140.
Then the compound 51 that, evaporation 20nm is thick on luminescent layer is as electron transfer layer 150.
Finally, evaporation 1nmLiF is that electron injecting layer 160 and 100nmAl are as device cathodes 170.
Prepared device (structural representation is shown in Fig. 5) records at 25mA/ with PhotoResearchPR650 spectrometercm2Current density under efficiency be 0.5cd/A, the current density under the driving voltage of 8V is 346mA/cm2, Fig. 6 represents thisThe organic electroluminescence device of embodiment is at 25mA/cm2Current density under emission spectrum, be green spectral.
Comparative example 1
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (the limited public affairs of South China glass group shareDepartment) warp successively: deionized water, ethanol, acetone and deionized water are cleaned, then use oxygen plasma treatment 30 seconds.
Then, evaporation NPB, forms the thick hole transmission layer 130 of 60nm.
Then, the thick Alq of evaporation 30nm on hole transmission layer3As luminescent layer 140.
Then, the thick Alq of evaporation 20nm on luminescent layer3As electron transfer layer 150.
Finally, evaporation 1nmLiF is that electron injecting layer 160 and 100nmAl are as device cathodes 170.
Prepared device records at 25mA/cm with PhotoResearchPR650 spectrometer2Current density underEfficiency is 0.28cd/A, and the current density under the driving voltage of 8V is 168mA/cm2, transmitting green light.
Under identical condition, apply organic electroluminescence prepared by the electric transmission compound based on benzimidazole of the present inventionThe efficiency of luminescent device and current density are higher than comparative example, and as mentioned above, compound of the present invention has high stability, thisThe organic electroluminescence device of bright preparation has high efficiency and optical purity.
Structural formula described in device

Claims (4)

1. an organic electroluminescence device, it comprises anode, negative electrode and organic layer, organic layer comprises hole injection layer, holeMore than the one deck in transport layer, luminescent layer, barrier layer, electron injecting layer and electron transfer layer, in described organic layer, at least compriseElectron transfer layer or electron injecting layer, is characterized in that in described electron transfer layer and described electron injecting layer that at least one deck comprisesThere is the compound of following structural formula (I):
Wherein, R1、R2、R3、R4、R5、R6、R7And R8Respectively independently selected from hydrogen, C1-C8 alkyl;
L1And L2Respectively independently selected from phenyl, the phenyl that replaced by C1-C4 alkyl, naphthyl, the naphthyl that replaced by C1-C4 alkyl;
X1And X2Respectively independently selected from NAr;
A is selected from O and S;
Wherein Ar is selected from the replacement of C1-C4 alkyl or unsubstituted following aryl:
2. organic electroluminescence device according to claim 1, wherein the compound of structural formula (I) is following structural formulaCompound:
3. organic electroluminescence device according to claim 1, is characterized in that the compound list as described in structural formula (I)Solely use, or and other compound uses.
4. organic electroluminescence device according to claim 1, is characterized in that the compound list as described in structural formula (I)Solely use a kind of compound wherein, or use the two or more compound in structural formula (I) simultaneously.
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