CN105047830B - A kind of organic electroluminescence device - Google Patents
A kind of organic electroluminescence device Download PDFInfo
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- CN105047830B CN105047830B CN201510290415.1A CN201510290415A CN105047830B CN 105047830 B CN105047830 B CN 105047830B CN 201510290415 A CN201510290415 A CN 201510290415A CN 105047830 B CN105047830 B CN 105047830B
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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Abstract
The invention provides a kind of organic electroluminescence device, it includes anode, negative electrode and organic layer, organic layer includes one or more layers in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, it is characterised in that at least one layer includes the compound of following lamps structure formula (I) in organic layer：
Description
Technical field
The present invention relates to technical field of organic electroluminescence, more particularly to a kind of organic electroluminescence device.
Background technology
Organic electroluminescence device (OLEDs) is by spin coating or vacuum evaporation deposition one between two metal electrodes
The device that layer organic material is prepared from, a classical three layer organic electroluminescence device includes hole transmission layer, luminescent layer
And electron transfer layer.The hole produced by anode through hole transmission layer with the electronics that is produced by negative electrode through combined with electron transfer layer
Luminescent layer formation exciton, then lights.Organic electroluminescence device can be adjusted as desired by the material of luminescent layer is changed
The light of the various needs of section transmitting.
Organic electroluminescence device is as a kind of new Display Technique, with self-luminous, wide viewing angle, low energy consumption, efficiency
High, thin, rich color, fast response time, Applicable temperature scope are wide, low driving voltage, can make flexible with it is transparent
Display panel and the particular advantages such as environment-friendly, can be applied on flat-panel monitor and a new generation's illumination, can also conduct
LCD backlight.
Since invention at the bottom of 1980s, organic electroluminescence device has industrially been applied, such as
As screens such as camera and mobile phones, but current OLED is low due to efficiency, and it is wider that the factor such as service life is short restricts it
General application, particularly large screen display.And restrict during one of key factor is exactly organic electroluminescence device
The performance of electroluminescent organic material.Additionally, due to OLED when applying voltage-operated, Joule heat can be produced so that
Organic material is easily crystallized, and have impact on life-span and the efficiency of device, therefore, it is also desirable to develop the organic electroluminescence of stability and high efficiency
Luminescent material.
Organic electrophosphorescenpolymer phenomenon breaches theoretical limitation of the organic electroluminescent quantum efficiency less than 25%, and lifting is arrived
100% (Baldo M.A., Forrest S.R.Et al, Nature, 1998,395,151-154), its application is also greatly carried
The high efficiency of organic electroluminescence device.Usually, electroluminescent phosphorescence needs to use host-guest system technology, conventional to be used as phosphorus
The CBP (4,4'-bis (9-carbazolyl)-biphenyl) of light material of main part has efficient and high triplet energy level, when its work
During for material of main part, triplet energy state effectively can be transferred to object phosphorescent light-emitting materials from light emitting host material.But by
Easily transmitted and the characteristic of electronics hardly possible flowing in CBP hole so that the charge unbalance of luminescent layer, as a result reduce the effect of device
Rate.Therefore, those skilled in the art are directed to a kind of efficient electroluminescent organic material of exploitation.
The content of the invention
Present invention firstly provides a kind of organic electroluminescent compounds with spiro structure, it is with following structural formula
(I) compound：
Wherein, R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Separately it is selected from hydrogen, deuterium, halogen, cyano group, nitro, C1-
C12 alkyl, C1-C8 alkoxyl, C6-C30 substitution or unsubstituted aryl, C3-C30 substitution or unsubstituted heteroaryl
Base；
A and B are separately selected from O, S, Se, NR11、CR12R13；
Wherein, R11~R13Separately selected from hydrogen, deuterium, halogen, C1-C12 alkyl, C1-C8 alkoxyl, C6-C30
Substitution or unsubstituted aryl, C3-C60 substitution or unsubstituted heteroaryl, C2-C8 substitution or unsubstituted alkene
Base, C2-C8 substitution or unsubstituted alkynyl.
Wherein preferred mode is：
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Separately it is selected from hydrogen, deuterium, halogen, C1-C8 alkyl, C1-C8 alkane
Epoxide, phenyl, naphthyl, pyridine radicals；
A and B are separately selected from O, S, NR11、CR12R13；
R11~R13Separately it is selected from hydrogen, deuterium, halogen, C1-C8 alkyl, C1-C8 alkoxyl, phenyl, naphthyl, pyridine
Base；
Further preferred mode is：
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13Separately it is selected from hydrogen, fluorine, nitro, methyl, second
Base, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, phenyl, naphthyl, pyridine radicals；
It is further preferred that the organic electroluminescent compounds with spiro structure of the present invention are following structural 1-33's
Compound：
The compound with spiro structure of the present invention can be applied in organic electroluminescence device, organic solar batteries,
OTFT or organophotoreceptorswith field.
The organic electroluminescent compounds of the present invention can be prepared by following synthetic method：
A in formula represented by B with structure formula (I) with defining, and R is expressed as methyl or ethyl.
Present invention also offers a kind of organic electroluminescence device, the device includes anode, negative electrode and organic layer, organic layer
Include one layer or one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer
More than layer, wherein the compound with spiro structure that at least one layer contains as described in structural formula (I) in the organic layer：
Wherein R1-R10, A and B it is defined as described above.
Wherein organic layer is luminescent layer；
Or organic layer is luminescent layer and electron transfer layer；
Or organic layer is luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole transmission layer and luminescent layer；
Or organic layer is hole injection layer, hole transmission layer and luminescent layer；
Or organic layer is hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole injection layer, hole transmission layer, barrier layer, luminescent layer, electron transfer layer and electron injection
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, wherein the layer where the compound with spiro structure as described in structure formula (I) is luminescent layer；
Preferably, the compound with spiro structure wherein described in structure formula (I) is structural formula 1-33 compound；
When the compound with spiro structure as described in structure formula (I) is used for luminescent device preparation, it can be used alone,
It can be used in mixed way with other compounds；The compound with spiro structure as described in structure formula (I) can be used alone wherein
A kind of compound, can also simultaneously use structure formula (I) in two or more compound.
The organic electroluminescence device of the present invention, further preferred mode is that the organic electroluminescence device includes sun
Contain in pole, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, wherein luminescent layer
The compound of one or more kinds of structure formula (I)s；It is further preferred that containing one or more kinds of knots in luminescent layer
Structure formula 1-33 compound.
The luminescent layer of organic electroluminescence device contains phosphorescence light emitting guest material and the compound with structure formula (I) is made
For material of main part, wherein structure formula (I) compound is as material of main part, and its concentration is the 20-99.9% of whole luminous layer weight,
It is preferred that 80-99%, more preferably 90-99%.
The gross thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
The organic electroluminescence device of the present invention can be used when having the compound of structure formula (I) using the present invention
Collocation other materials, such as hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and barrier layer,
And obtain blue and green light, gold-tinted, feux rouges or white light.
The hole transmission layer and hole injection layer of organic electroluminescence device of the present invention, material requested have good hole
Transmission performance, can effectively be transferred to hole on luminescent layer from anode.There is compound described in structure formula (I) except above-mentioned
Outside, other small molecules and macromolecular organic compound, including but not limited to carbazole compound, triaromatic amine can also be included
Compound, benzidine compound, compound of fluorene class, phthalocyanine-like compound, the miscellaneous triphen of six cyano group six
(hexanitrilehexaazatriphenylene), the cyanogen dimethyl-parabenzoquinone (F4- of 2,3,5,6- tetra- fluoro- 7,7', 8,8'- tetra-
TCNQ), PVK, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of the organic electroluminescence device of the present invention, with the good characteristics of luminescence, can be adjusted as needed
The scope of visible ray.Except the present invention have structure formula (I) compound as phosphorescent light body material in addition to, can also arrange in pairs or groups other phosphorus
Light material of main part, phosphorescence light emitting guest material can be included selected from least one of ruthenium, copper, rhodium, silver, iridium, platinum, gold and osmium gold
The metal-organic complex of category.
The Organic Electron Transport Material requirement of organic electroluminescence device of the present invention has good electronic transmission performance, energy
It is enough effectively electronics from cathode transport to luminescent layer in, with very big electron mobility.Following compound can be selected, but
It is not limited to this：Oxa- oxazole, thiazole compound, triazole compound, three nitrogen piperazine class compounds, triazine class chemical combination
Thing, quinoline class compound, phenodiazine anthracene compound, siliceous heterocycle compound, quinolines, ferrosin class compound,
Metallo-chelate (such as Alq3), fluorine substituted benzene compound, benzimidazoles compound.
Electronics, effectively can be injected into organic layer by the electron injecting layer of organic electroluminescence device of the present invention from negative electrode
In, it is mainly selected from the compound of alkali metal or alkali metal, or compound or alkali selected from alkaline-earth metal or alkaline-earth metal
Metal complex, can select following compound, but not limited to this：Alkali metal, alkaline-earth metal, rare earth metal, alkali metal
Oxide or halide, the oxide of alkaline-earth metal or halide, the oxide of rare earth metal or halide, alkali metal
Or the organic complex of alkaline-earth metal；Preferably lithium, lithium fluoride, lithia, lithium nitride, 8-hydroxyquinoline lithium, caesium, carbonic acid
Caesium, 8-hydroxyquinoline caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesia, these compounds can individually make
With can also mixture use, can also be used cooperatively with other electroluminescent organic materials.
Each layer of organic layer in the organic electroluminescence device of the present invention, can be steamed by vacuum vapour deposition, molecular beam
It is prepared by the modes such as plating method, the dip coating for being dissolved in solvent, spin-coating method, stick coating method or inkjet printing.It can make for metal motor
Prepared with vapour deposition method or sputtering method.
Device experimental shows, compound with spiro structure of the present invention as described in structure formula (I), with preferable thermally-stabilised
Property, high-luminous-efficiency, high luminance purity.The organic electroluminescence device tool made using this based on the compound with spiro structure
Have the advantages that electroluminescent efficiency is good and excitation is excellent and long lifespan.
Brief description of the drawings
Fig. 1 is the hydrogen nuclear magnetic spectrogram of compound 7.
Fig. 2 is the hydrogen nuclear magnetic spectrogram of compound 15.
Fig. 3 is a kind of organic electroluminescence device structural representation of the invention
Wherein, 110 glass substrate is represented as, 120 are represented as anode, and 130 are represented as hole injection layer, and 140 are represented as sky
Cave transport layer, 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 the moon
Pole.
Embodiment
In order to describe the present invention in more detail, especially exemplified by example below, but not limited to this.
Embodiment 1
The synthesis of compound 7
Intermediate 7-1 synthesis
In three-necked flask, addition 4- dibenzofurans boric acid (10.5g, 50mmol), o-bromobenzoic acid methyl esters (11.7g,
55mmol), potassium carbonate (13.8g, 10mmol), tetra-triphenylphosphine palladium (100mg, 0.075mmol), 50ml water, the four of 100ml
Hydrogen furans, reacts 10 hours, cooling, adds dichloromethane extraction, dries, concentration, and crude product obtains 13.4g through column chromatography and produced
Product, yield is 89%, FAB-MS:302.1.
Intermediate 7-2 synthesis
In three-necked flask, intermediate 7-1 (10g, 33mmol) is added, 50g polyphosphoric acids heated under nitrogen is to 160 degree
Reaction 5 hours, cooling, pours into frozen water, is extracted with ethyl acetate, and dries, concentration, and crude product obtains 6g productions with ethyl alcohol recrystallization
Product, yield is 67%, FAB-MS:270.3.
Intermediate 7-3 synthesis
In three-necked flask, 9,9- dimethyl-boric acid of fluorenes -2 (10g, 42mmol) is added, adjacent bromo-iodobenzene (23.6g,
84mmol), potassium carbonate (13.8g, 10mmol), tetra-triphenylphosphine palladium (100mg, 0.075mmol), 50ml water, the four of 100ml
Hydrogen furans, reacts 10 hours, cooling, adds dichloromethane extraction, dries, concentration, crude product obtains 12g products through column chromatography,
Yield is 82%, FAB-MS:348.1.
The synthesis of compound 7
In three-necked flask, intermediate 7-3 (5g, 14.3mmol) is added, 50ml dry tetrahydrofuran is cooled to -78
Degree, adds the hexane solution (14.3mmol) of 5.8ml 2.5M n-BuLi, reacts 2 hours, and addition is dissolved with intermediate
7-2 tetrahydrofuran solution (3.9g, 14.3mmol), is then slowly raised to room temperature reaction and stays overnight, and adds in frozen water, uses acetic acid second
Ester is extracted, and is concentrated to give intermediate 7-4 crude product, is then added 50ml acetic acid and 5ml concentrated hydrochloric acid, is heated to reflux 5 small
When, solvent is removed, dichloromethane extraction is added, dries, concentration, crude product obtains 3.8g products through column chromatography, yield 51%,
FAB-MS:522.2,1H NMR (400MHz, CDCl3, δ):8.41-8.43 (d, J=7.6Hz, 1H), 7.90-7.95 (m, 3H),
7.69-7.77 (m, 2H), 7.36-7.54 (m, 6H), 7.06-7.20 (m, 5H), 6.74-6.87 (m, 3H), 1.60 (s, 6H).Core
Magnetic spectrum figure is as shown in Figure 1.
Embodiment 2
The synthesis of compound 15
Intermediate 15-1 synthesis
In three-necked flask, addition 4- dibenzothiophenes boric acid (11.5g, 50mmol), o-bromobenzoic acid methyl esters (11.7g,
55mmol), potassium carbonate (13.8g, 10mmol), tetra-triphenylphosphine palladium (100mg, 0.075mmol), 50ml water, the four of 100ml
Hydrogen furans, reacts 10 hours, cooling, adds dichloromethane extraction, dries, concentration, and crude product obtains 12.6g through column chromatography and produced
Product, yield is 79%, FAB-MS:318.0.
Intermediate 15-2 synthesis
In three-necked flask, intermediate 15-1 (10g, 31mmol), 50g polyphosphoric acids heated under nitrogen to 160 are added
Degree reaction 5 hours, cooling is poured into frozen water, is extracted with ethyl acetate, and is dried, and concentration, crude product is obtained with ethyl alcohol recrystallization
6.3g products, yield is 70%, FAB-MS:286.1.
The synthesis of compound 15
In three-necked flask, intermediate 7-3 (5g, 14.3mmol) is added, 50ml dry tetrahydrofuran is cooled to -78
Degree, adds the hexane solution (14.3mmol) of 5.8ml 2.5M n-BuLi, reacts 2 hours, and addition is dissolved with intermediate
15-2 tetrahydrofuran solution (4.1g, 14.3mmol), is then slowly raised to room temperature reaction and stays overnight, and adds in frozen water, uses acetic acid
Ethyl ester is extracted, and is concentrated to give intermediate 15-3 crude product, is then added 50ml acetic acid and 5ml concentrated hydrochloric acid, is heated to reflux 5
Hour, solvent is removed, dichloromethane extraction is added, dries, concentration, crude product obtains 4.1g products through column chromatography, yield 53%,
FAB-MS:538.2,
1H NMR (400MHz, CDCl3, δ):8.13-8.17 (m, 2H), 7.91-8.03 (m, 4H), 7.36-7.56 (m,
6H), 7.06-7.22 (m, 5H), 6.88-6.93 (m, 2H), 6.73-6.75 (d, J=7.6Hz, 1H), 1.60 (s, 6H).Nuclear-magnetism
Spectrogram is as shown in Figure 2.
Embodiment 3
The synthesis of compound 1
Intermediate 1-1 synthesis
With intermediate 7-3 synthetic method, except replacing the fluorenes boron of 9,9- dimethyl -2 with 3- dibenzofurans boric acid
Acid, yield is 75%, FAB-MS:322.5.
The synthesis of compound 1
With the synthetic method of compound 7, intermediate 7-3 is replaced with intermediate 1-1, yield is 49%, FAB-MS:
496.1.Embodiment 4
The synthesis of compound 10
The synthetic method of compound 10 with the synthetic method of compound 15, intermediate 7-3 is replaced with intermediate 1-1,
Yield is 37%, FAB-MS:512.3.
Embodiment 5
The synthesis of compound 6
Intermediate 6-1 synthesis
With intermediate 7-3 synthetic method, replacing the fluorenes boric acid of 9,9- dimethyl -2 with 9- phenyl-carbazole -2- boric acid,
Yield is 73%, FAB-MS:397.6.
The synthesis of compound 6
Synthetic method with intermediate 6-1 with the synthetic method of compound 7, replacing intermediate 7-3, yield 31%,
FAB-MS:571.2。
Embodiment 6
The synthesis of compound 13
Synthetic method with intermediate 6-1 with the synthetic method of compound 15, replacing intermediate 7-3, yield 48%,
FAB-MS:587.2
Embodiment 7
The preparation of organic electroluminescence device
As shown in figure 3, preparing OLED using the compound 7 of embodiment 1
First, by electrically conducting transparent ito glass substrate 110 (carrying anode 120 above) (the limited public affairs of South China glass group share
Department) pass through successively：Deionized water, ethanol, acetone and deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, it is hole injection layer 130 that the thick HAT-CN of 5nm are deposited on ITO.
Then, TAPC is deposited, the thick hole transmission layers 140 of 65nm are formed.
Then, steamed on hole transmission layer and cross the thick luminescent layers 150 of 10nm, wherein, compound 7 is main body luminescent material, and
With 7%Ir (ppy)2Acac is used as phosphorescence doping guest materials.
Then, the thick TmPyPB of 50nm are deposited on luminescent layer and are used as electron transfer layer 160.
Finally, evaporation 1nm LiF are that electron injecting layer 170 and 100nm Al are used as device cathodes 180.
Embodiment 8-12
It is other with implementing in addition to replacing material of main part of the compound 7 as luminescent layer with embodiment 2-6 compound
The equally progress of example 7 prepares device.
Prepared device (structural representation is shown in Fig. 3) is measured with Photo Research PR650 spectrometers
1000cd/m2Embodiment 7-12 device performance such as table 1 under brightness.
Comparative example 1
First, by electrically conducting transparent ito glass substrate 110 (carrying anode 120 above) (the limited public affairs of South China glass group share
Department) pass through successively：Deionized water, ethanol, acetone and deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, it is hole injection layer 130 that the thick HAT-CN of 5nm are deposited on ITO.
Then, TAPC is deposited, the thick hole transmission layers 140 of 65nm are formed.
Then, steamed on hole transmission layer and cross the thick luminescent layers 150 of 10nm, wherein, compound CBP is main body luminescent material,
And with 7%Ir (ppy)2Acac is used as phosphorescence doping guest materials.
Then, the thick TmPyPB of 50nm are deposited on luminescent layer and are used as electron transfer layer 160.
Finally, evaporation 1nm LiF are that electron injecting layer 170 and 100nm Al are used as device cathodes 180.
Prepared device (structural representation is shown in Fig. 3) is measured with Photo Research PR650 spectrometers
1000cd/m2Performance such as table 1 under brightness.
Table 1
| Compound | Driving voltage (V) | Current efficiency (cd/A) | Spectrum | |
| Embodiment 7 | 7 | 4.3 | 35.4 | Green glow |
| Embodiment 8 | 15 | 4.0 | 36.7 | Green glow |
| Embodiment 9 | 1 | 4.5 | 33.2 | Green glow |
| Embodiment 10 | 10 | 4.1 | 35.8 | Green glow |
| Embodiment 11 | 6 | 4.0 | 37.5 | Green glow |
| Embodiment 12 | 13 | 3.9 | 39.6 | Green glow |
| Comparative example 1 | CBP | 5.6 | 20.1 | Green glow |
Under identical brightness, the drive of the organic electroluminescence device prepared using the material of main part of the spiro structure of the present invention
Dynamic voltage ratio is relatively low, and efficiency comparison is high, as described above, the compound of the present invention has high stability, prepared by the present invention
Organic electroluminescence device there is high efficiency and low driving voltage.
Structural formula described in device
。
Claims (7)
1. a kind of organic electroluminescence device, it includes anode, negative electrode and organic layer, and organic layer injects comprising luminescent layer, hole
It is one or more layers in layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, it is characterised in that hair
Photosphere includes the compound of following structure formula (I)：
Wherein, R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Separately it is selected from hydrogen, deuterium, C1-C12 alkyl；
There is one to be selected from O, S in A and B, another is selected from O, S, NR11、CR12R13；
Wherein, R11Selected from hydrogen, deuterium, C1-C12 alkyl, phenyl, naphthyl；
R12~R13Separately it is selected from hydrogen, deuterium, C1-C12 alkyl.
2. organic electroluminescence device according to claim 1, it is characterised in that wherein
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Separately it is selected from hydrogen, deuterium, C1-C8 alkyl.
3. organic electroluminescence device according to claim 1, it is characterised in that wherein
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13Separately it is selected from hydrogen, methyl, ethyl, propyl group, isopropyl
Base, the tert-butyl group, normal-butyl, n-hexyl.
4. organic electroluminescence device according to claim 1, it is characterised in that the compound of structure formula (I) is following knot
The compound of structure formula：
5. organic electroluminescence device according to claim 1, it is characterised in that the compound list as described in structure formula (I)
A kind of compound therein is solely used, or uses two or more the compound in structure formula (I) simultaneously.
6. organic electroluminescence device according to claim 1, it includes anode, hole injection layer, hole transmission layer, hair
Photosphere, electron transfer layer, electron injecting layer and negative electrode, it is characterised in that contain one or more kinds of structural formulas in luminescent layer
(I) compound.
7. organic electroluminescence device according to claim 1, it includes anode, hole injection layer, hole transmission layer, hair
Photosphere, electron transfer layer, electron injecting layer and negative electrode, it is characterised in that be containing one or more kinds of structural formulas in luminescent layer
1-8,10-16,18-22,27-29 compound.
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