CN103887447B - A kind of organic electroluminescence device - Google Patents

A kind of organic electroluminescence device Download PDF

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CN103887447B
CN103887447B CN201410128310.1A CN201410128310A CN103887447B CN 103887447 B CN103887447 B CN 103887447B CN 201410128310 A CN201410128310 A CN 201410128310A CN 103887447 B CN103887447 B CN 103887447B
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organic electroluminescence
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CN103887447A (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
    • 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
    • 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]
    • H10K50/14—Carrier transporting layers
    • 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]
    • H10K50/17—Carrier injection layers
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene

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Abstract

The invention provides 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 hole injection layer, hole transmission layer, luminescent layer, barrier layer, electron injecting layer and electron transfer layer, and wherein in organic layer, at least one deck includes the compound of following structural formula (I).

Description

A kind of organic electroluminescence device
Technical field
The present invention relates to field of organic electroluminescence, relate to a kind of organic electroluminescence device specifically.
Background technology
Organic electroluminescence device (OLEDs) is steam by spin coating or vacuum the device crossing deposition one deck organic material and be 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.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.
In OLED material, because the speed of most electroluminescent organic material transporting holes is faster than the speed of transmission electronic, easily cause electronics and the number of cavities imbalance of luminescent layer, the efficiency of such device is just lower.Three (oxine) aluminium (Alq 3) since invention, be extensively studied, but it is still very low as its electron mobility of electron transport material, and the intrinsic characteristic that self can degrade, with in the device of electron transfer layer, there will be the situation of voltage drop, simultaneously, due to lower electron mobility, a large amount of holes is made to enter into Alq 3in layer, excessive hole with the form emittance of non-luminescent, and when as electron transport material, due to the characteristic of its green light, application is restricted.Therefore, development stability and have the electron transport material of larger electron mobility, has great value to widely using of organic electroluminescence device.
Summary of the invention
First the present invention provides a kind of organic electroluminescent compounds, and it is the compound with following structural formula I:
Wherein, R 1-R 8be separately hydrogen, D-atom, halogen, cyano group, nitro, C1-C8 alkyl, C1-C8 alkoxyl, the replacement of C6-C30 or unsubstituted aryl, the replacement of C3-C30 or unsubstituted heteroaryl, the replacement of C2-C8 or unsubstituted allylic alkylation, the replacement of C2-C8 or unsubstituted alkynes alkyl;
Ar 1, Ar 2and Ar 3be separately C1-C8 alkyl, the replacement of C6-C60 or unsubstituted aryl, the replacement of C3-C60 or unsubstituted heteroaryl;
L 1and L 2it is separately the substituted or unsubstituted aryl of sky, singly-bound, C6-C30.
Wherein preferred mode is:
R 1-R 8be separately hydrogen, halogen, cyano group, nitro, C1-C8 alkyl, C1-C8 alkoxyl, the replacement of C2-C8 or unsubstituted allylic alkylation, the replacement of C2-C8 or unsubstituted alkynes alkyl, phenyl, naphthyl, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinoline;
Ar 1, Ar 2and Ar 3be separately the phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylene base, the fluoranthene base that are replaced by C1-C4 alkyl or C6-C30 aryl; Or Ar 1, Ar 2and Ar 3be separately (9,9-dialkyl group) fluorenyl, (9,9-bis-replaces or unsubstituted aryl) fluorenyl, 9,9-Spirofluorene-based, replace or unsubstituted dibenzothiophenes base, replacement or unsubstituted dibenzofuran group, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinoline;
L 1and L 2be separately sky, singly-bound, phenyl, the phenyl replaced by C1-C4 alkyl, naphthyl, the naphthyl that replaced by C1-C4 alkyl;
Wherein above-mentioned phenyl, naphthyl, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinoline can further replace by the alkyl of C1-C4;
Preferred mode is further:
R 1-R 8independently be selected from hydrogen, methoxyl group, fluorine, methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, phenyl, naphthyl, pyridine radicals, pyrimidine radicals, triazol radical, three nitrogen piperazine bases, quinolyl;
L 1and L 2separately be selected from sky, singly-bound, phenyl, naphthyl;
Ar 1, Ar 2and Ar 3independently be selected from methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, phenyl, naphthyl, pyridine radicals, pyrimidine radicals, triazol radical, three nitrogen piperazine bases, quinolyl, substituted or unsubstituted following aryl:
Wherein above-mentioned phenyl, naphthyl, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinoline can further replace by the alkyl of C1-C4.
Preferred further, organic electroluminescent compounds of the present invention is the compound of following structural 1-36.
Organic electroluminescent compounds of the present invention can be prepared by Suzuki coupling and Buchwald-Hartwig reaction.
Organic electroluminescent compounds 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 and electron transfer layer, has one deck at least containing, for example the organic electroluminescent compounds described in structural formula (I) in wherein said organic layer:
Structural formula I
Wherein R 1-R 8, Ar 1-Ar 3, and L 1-L 2definition as previously mentioned.
Wherein organic layer is luminescent layer;
Or organic layer is luminescent layer and hole injection layer;
Or organic layer is luminescent layer and hole transmission layer;
Or 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 barrier layer;
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;
The layer at the organic electroluminescent compounds place wherein as described in structural formula (I) is luminescent layer, electron transfer layer or hole injection layer;
Organic electroluminescent compounds wherein described in structural formula (I) is the compound of structural formula 1-36;
Organic electroluminescent compounds as described in structural formula I can be used alone, and also can use with other compound; Organic electroluminescent compounds as described in structural formula I can be used alone a kind of compound wherein, also can use two or more the compound in structural formula I simultaneously.
Organic electroluminescence device of the present invention, preferred mode is further, this organic electroluminescence device comprises anode, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, the compound wherein containing structural formula (I) in electron transfer layer; Preferred further, the compound in electron transfer layer is the compound of structural formula 1-36.
When Compounds of structural formula I is as luminescent layer, can as non-impurity-doped luminescent layer or doping luminescent layer.
Described doping luminescent layer comprises material of main part and guest materials, and when structural formula (I) compound 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%.When structural formula (I) compound is as guest materials, its concentration is 0.01-80% of this luminescent layer weight, and preferred 1-20%, is more preferably 1-10%.
Two of structural formula I compounds can be used to make material of main part and guest materials respectively simultaneously.
The gross thickness of organic electroluminescence device organic layer of the present invention is 1-1000nm, preferred 50-500nm.
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.Have except structural formula (I) described compound except above-mentioned, other Small molecular and macromolecular organic compound can also be comprised, include but not limited to 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 '-four 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.Except containing except phenol piperazine compounds of the present invention, can also containing, for example lower compound, include, but are not limited to naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance compounds, bend compounds, fluoranthene compounds, anthracene compounds, pentacene compounds, perylene compounds, two aromatic ethylene compounds, triphenylamine ethylene compounds, aminated compounds, carbazole compound, benzimidazoles compound, furfuran compound, metal organic fluorescence complex compound, metal Phosphorescent complex compound is (as Ir, Pt, Os, Cu), polyvinylcarbazole, poly-organosilicon compound, the organic polymer luminescent materials such as polythiophene, they can be used alone, also can use by multiple mixture.The thickness of luminescent layer is preferably 10-50nm.
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.
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 gold brush or halide, the oxide of 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 cross the modes such as method, molecular beam vapour deposition method, the dip coating being dissolved in solvent, spin-coating method, stick coating method or inkjet printing by vacuum steaming and prepare.Vapour deposition method or sputtering method can be used to be prepared for metal motor.
Device experimental shows, the organic electroluminescent compounds 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 organic electroluminescent compounds 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 a kind of organic electroluminescence device structural representation of the present invention
Wherein, 110 are represented as glass substrate, and 120 are represented as anode, and 130 are represented as hole transmission layer, and 140 are represented as luminescent layer, and 150 are represented as electron transfer layer, and 160 are represented as electron injecting layer, and 170 are represented as negative electrode.
Fig. 2 is that embodiment 2 is at 100mA/em 2current density under emission spectrum.
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 15
The synthesis of intermediate 15-2
In flask, add compound 15-1 (2g, 5.1mmol), connection boric acid frequently receives alcohol ester (1.5g, 6.18mmol), potassium acetate (15.4mmol), Pd (dppf) 2cl 2(100mg), the DMF of 40ml, is heated to 90 DEG C of reactions 12 hours under nitrogen protection; cooling, is poured into water, with dichloromethane extraction, with anhydrous sodium sulfate drying; concentrated, crude product silica column purification obtains 1.5g white solid, and productive rate is 68%.
1HNMR(400MHz，CDCl 3，δ)：8.75-8.80(m，6H)，8.00-8.02(d，J=8Hz，2H)，7.57-7.63(m，6H)，1.40(s，12H)。
The synthesis of intermediate 15-3 and 15-4
In flask, add the NMP (1-METHYLPYRROLIDONE) of N-phenyl-1,2-phenylenediamine (9.2g, 50mmol) and 80ml, then add 4-bromo-benzoyl chloride (10.9g, 50mmol) stirred at ambient temperature reaction spend the night.React, reactant liquor is poured into water, has a large amount of solid to separate out, filter, filter cake THF (oxolane) and recrystallizing methanol, the white solid that obtains (intermediate 15-3) adds 100ml acetic acid and adds hot reflux 12 hours, has reacted, removal of solvent under reduced pressure, add 50ml methyl alcohol, filter, obtain 12g white solid (intermediate 15-4), productive rate is 69%.Wherein the nuclear-magnetism of 15-4 is:
1HNMR(400MHz，DMSO，δ)：7.78-7.81(d，J=7.6Hz，1H)，7.54-7.60(m，5H)，7.43-7.46(m，4H)，7.26-7.34(m，2H)，7.17-7.19(d，J=7.2Hz，1H).
The synthesis of intermediate 15-5
Under nitrogen protection, in the there-necked flask that THF dried for intermediate 15-4 (10.6g, 29mmol) and 100ml adds, but to-78 DEG C.N-BuLi hexane solution (the 20mL of 2.5M is under agitation slowly injected subsequently with syringe; 50mmol); and then add triisopropyl borate ester (8.1g; 43mmol); continue stirring 1 hour at this temperature; then slowly rise to room temperature, stir under nitrogen protection and spend the night.React, reactant liquor has been poured in the dilute hydrochloric acid solution of 2N, and be extracted with ethyl acetate three times, merged organic phase, use salt solution and washing successively, then use anhydrous sodium sulfate drying.Except desolventizing, crude product ethyl acetate and n-hexane recrystallization obtain 8.3g white solid, and productive rate is 74%. 1HNMR(400MHz，DMSOδ)：8.14(s，2H)，7.34-7.82(m，3H)，7.43-7.50(m，7H)，7.20-7.35(m，3H)。
The synthesis of intermediate 15-6
In flask, add 9-bromine anthracene (0.77g, 3mmol), the 2MK of THF and 10ml of intermediate 15-5 (0.92g, 3mmol), 10ml 2cO 3the aqueous solution; under nitrogen protection, add 50mg tetra-(triphenyl phosphorus) palladium, then heat 12 hours; react; cooling, with dichloromethane extraction three times, organic over anhydrous dried over sodium sulfate; decompression removing organic solvent; crude product ethyl alcohol recrystallization, obtains 0.94g yellow solid, and productive rate is 70%. 1HNMR(400MHz，CDCl 3，δ)：8.49(s，1H)，8.03-8.05(d，J=8.4Hz，2H)，7.94-7.96(d，J=8.0Hz，1H)，7.78-7.80(d，J=8.4Hz，2H)，7.57-7.63(m，4H)，7.44-7.54(m，5H)，7.31—7.40(m，7H).
The synthesis of intermediate 15-7
In flask, add intermediate 15-6 (0.95g, 2.13mmol), NBS (N-bromo-succinimide) (0.4g, 2.13mmol) and 10ml chloroform.Under nitrogen protection, 50 DEG C of reactions 12 hours are heated to.Reacted, removing chloroform, crude product acetone and methanol mixed solvent recrystallization obtain 0.75g yellow solid, and productive rate is 68%. 1HNMR(400MHz，CDCl 3，δ)：8.60-8.62(d，J=8.4Hz，2H)，7.94-7.96(d，J=8.0Hz，1H)，7.79-7.81(d，J=8.0Hz，2H)，7.54-7.62(m，7H)，7.47-7.48(d，J=8.4Hz，2H)，7.33-7.41(m，5H)，7.32(m，2H).
The synthesis of compound 15
In single port flask; add intermediate 15-2 (0.3g; 0.68mmol); the oxolane of intermediate 15-7 (0.3g, 0.57mmol), 10ml and the 2M wet chemical of 10ml; under nitrogen protection; add four (triphenyl phosphorus) palladium (10mg, 0.0075mmol), then add hot reflux 12 hours; react; cooling, with dichloromethane extraction three times, organic over anhydrous dried over sodium sulfate; rotate removing organic solvent; crude product carries out column chromatography purification, obtains 0.31g yellow solid, and productive rate is 72%.
ESI, m/z:[M+H] +calcdforC 54h 36n 5, theoretical value is: 754.30; Measured value: 754.29.
Embodiment 2
The preparation of organic electroluminescence device
The compound 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, steam and cross NPB, form the hole transmission layer 130 that 60nm is thick.
Then, on hole transmission layer, the thick compd A lq of 30nm is crossed in steaming 3as luminescent layer 140.
Then, on luminescent layer, steaming crosses the thick compound of 20nm 15 as electron transfer layer 150.
Finally, steam that to cross 1nmLiF be that electron injecting layer 160 and 100nmAl are as device cathodes 170.
Prepared device PhotoResearchPR650 spectrometer records at 50mA/cm 2current density under efficiency be 2.13cd/A, 100mA/cm 2current density under efficiency be that 2.54cd/A, Fig. 2 represent that the organic electroluminescence device of the present embodiment is at 100mA/cm 2current density under emission spectrum, 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, steam and cross NPB, form the hole transmission layer 130 that 60nm is thick.
Then, on hole transmission layer, the thick Alq of 30nm is crossed in steaming 3as luminescent layer 140.
Then, on luminescent layer, the thick Alq of 20nm is crossed in steaming 3as electron transfer layer 150.
Finally, steam that to cross 1nmLiF be that electron injecting layer 160 and 100nmAl are as device cathodes 170.
Prepared device PhotoResearchPR650 spectrometer records at 50mA/cm 2current density under efficiency be 0.55cd/A, 50mA/cm 2current density under efficiency be 0.94cd/A, transmitting green light
At identical conditions, the efficiency of organic electroluminescence device prepared by organic electroluminescent compounds of the present invention is applied higher than comparative example.As mentioned above, compound of the present invention has high stability, and organic electroluminescence device prepared by the present invention has high efficiency and optical purity.
Structural formula described in device

Claims (4)

1. an organic electroluminescence device, it comprises anode, negative electrode and organic layer, organic layer comprises more than one deck 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 of following structural formula (I)
Wherein, R 1-R 8be separately hydrogen;
Ar 1, Ar 2and Ar 3it is separately phenyl;
L 1and L 2it is separately phenyl.
2. organic electroluminescence device according to claim 1, is characterized in that the layer at the compound place as described in structural formula (I) is luminescent layer, electron transfer layer or hole injection layer.
3. organic electroluminescence device according to claim 1, is characterized in that the compound as described in structural formula (I) is used alone, or and other compound use.
4. 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 containing structural formula (I) in electron transfer layer.
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