CN104892487B - A kind of anthracene class organic electroluminescent compounds and its organic electroluminescence device - Google Patents
A kind of anthracene class organic electroluminescent compounds and its organic electroluminescence device Download PDFInfo
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Abstract
The invention provides a kind of as structural formula I anthracene class organic electroluminescent compounds, the compound have preferable heat endurance, high-luminous-efficiency, high luminance purity, it can be used for making organic electroluminescence device, applied to organic solar batteries, OTFT or organophotoreceptorswith field.Present invention also offers 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, at least one layer of compound comprising just like structural formula I in organic layer.
Description
Technical field
The present invention relates to technical field of organic electroluminescence, and in particular to a kind of anthracene class organic electroluminescent compounds and its
Organic electroluminescence device, belong to organic electroluminescence device display technology field.
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, a classical three layer organic electroluminescence device include hole transmission layer, luminescent layer
And electron transfer layer.Hole follows the electronics as caused by negative electrode to be incorporated in through electron transfer layer through hole transmission layer as caused by anode
Luminescent layer forms exciton, then lights.Organic electroluminescence device can be adjusted as desired by the material for changing luminescent layer
Section launches the light of various needs.
Organic electroluminescence device has self-luminous, wide viewing angle, low energy consumption, efficiency as a kind of new Display Technique
High, thin, rich in 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, it can apply on flat-panel monitor and a new generation's illumination, can also conduct
LCD backlight.
Since the invention at the bottom of the 1980s, organic electroluminescence device has industrially been applied, such as
As screens such as camera and mobile phones, but current OLED, because efficiency is low, it is wider that the factors such as service life is short restrict it
General application, particularly large screen display, it is therefore desirable to improve the efficiency of device.And restrict one of key factor just
It is the performance of the electroluminescent organic material in organic electroluminescence device.It is voltage-operated in application additionally, due to OLED
When, Joule heat can be produced so that organic material easily crystallizes, and have impact on life-span and the efficiency of device, therefore, it is also desirable to
Develop the electroluminescent organic material of stability and high efficiency.
Among three primary colors (red, blue, green), feux rouges and green light material have been achieved for very big development recently, also comply with
The market demand of panel.For stable and efficient blue light material or seldom, due to the high energy gap of blue light so that for material
Requirement it is higher, and the problem of stability due to blue phosphor materials and optical purity are present, therefore develop the indigo plant of efficient stable
Color fluorescent material is particularly important.
The content of the invention
Present invention firstly provides a kind of anthracene derivative, and it is the compound with following structural formula I：
Wherein, Ar1And Ar2The separately substitution selected from C6-C30 or unsubstituted aryl；
Ar3Substitute unsubstituted phenyl, xenyl, fluorenyl, naphthyl selected from singly-bound, C6-C30；
R1And R2Separately it is selected from the substitution or unsubstituted of C1-C12 alkyl, C1-C8 alkoxy, C6-C30
Aryl.
Preferably, wherein
Ar1And Ar2Separately selected from tolyl, phenyl, 1- naphthyls, 2- naphthyls, xenyl, fluorenyl；
Ar3Selected from singly-bound, phenyl, naphthyl, xenyl, fluorenyl；
R1And R2Separately selected from methyl, ethyl, propyl group, isopropyl, isobutyl group, normal-butyl, the tert-butyl group, n-pentyl,
Isopentyl, n-hexyl, cyclohexyl, octyl group.
It is further preferred that the anthracenes luminescent compounds of the present invention are following structural 1-18 compound：
The anthracene compound of the present invention can be prepared into by Suzuki coupling reactions and Buchwald-Hartwig reactions
Arrive.
The anthracene compound of the present invention can be applied in organic electroluminescence device, organic solar batteries, organic film
Transistor or organophotoreceptorswith field.
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 at least one layer anthracene compound contained as described in structural formula I in the organic layer：
Wherein Ar1、Ar2、Ar3、R1、R2It 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 anthracene compound as described in structural formula I is luminescent layer；
Preferably, the anthracene compound wherein described in structural formula I is structural formula 1-18 compound；
When anthracene compound as described in structural formula I is used for luminescent device and prepared, can be used alone, can also and other
Compound is used in mixed way；Anthracene compound as described in structural formula I can be used alone a kind of compound therein, can also be same
When use two or more the compound in structural formula I.
The organic electroluminescence device of the present invention, further preferred mode are that the organic electroluminescence device includes sun
Contain one or more kinds of structural formula I in pole, hole transmission layer, luminescent layer, electron transfer layer and negative electrode, wherein luminescent layer
Compound；It is further preferred that the compound containing one or more kinds of structural formula 1-18 in luminescent layer.
The structural formula I of present invention compound can be used as the single luminescent layer of non-impurity-doped or doping luminescent layer, wherein structure
Compound of formula I is 20-99.9%, the preferably 80-99% of whole luminous layer weight as material of main part, its concentration, is more preferably
90-99%；During as guest materials, its concentration is the 0.1-50%, preferably 0.5%-10% of whole luminescent layer.
The gross thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
When having structural formula I compound using the present invention, can arrange in pairs or groups makes the organic electroluminescence device of the present invention
With other materials, such as in hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer or barrier layer
Deng, 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, effectively hole can be transferred on luminescent layer from anode.Other small molecules can be included and macromolecule is organic
Compound, including but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine
Class compound, six cyano group, six miscellaneous triphen (hexanitrilehexaazatriphenylene), 2,3,5,6- tetra- fluoro- 7,7', 8,
The cyanogen dimethyl-parabenzoquinones (F4-TCNQ) of 8'- tetra-, PVK, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of the organic electroluminescence device of the present invention, has the good characteristics of luminescence, can adjust as needed
The scope of visible ray.Except the present invention there is Compounds of structural formula I in addition to, can also contain following compound, but not limited to this,
Naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance class compound, class compound in the wrong, glimmering anthracene compound, anthracene class chemical combination
Thing, pentacene class compound, class compound, two aromatic ethylene class compounds, triphenylamine ethylene compounds, aminated compounds,
Benzimidazoles compound, furfuran compound, organic metal chelate complex.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires good electronic transmission performance, energy
It is enough effectively electronics from cathode transport to luminescent layer in, there is very big electron mobility.Following compound can be selected, but
This is not limited to, 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.
The electron injecting layer of organic electroluminescence device of the present invention, electronics effectively can be injected into organic layer 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 either 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 either 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, it 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 that anthracene compound of the present invention as described in structural formula I has preferable heat endurance, and height lights
Efficiency, high luminance purity.Using the anthracene compound make organic electroluminescence device have electroluminescent efficiency well and
Excitation is excellent and the advantages of long lifespan.
Brief description of the drawings
Fig. 1 is the high resolution mass spectrum figure of compound 2；
Fig. 2 is the high resolution mass spectrum figure of compound 7；
Fig. 3 is a kind of organic electroluminescence device structural representation of the present 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；Fig. 4 is device current density-current efficiency figure of compound 2.
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 2
Intermediate 2-1 synthesis
Bromo- 9, the 9- dimethyl fluorenes (140g, 0.5mol) of 2-, o-chloraniline (95g, 0.75mol), uncle are added into reaction bulb
Butanol potassium (90g, 0.8mol), palladium (3.3g, 15mmol), tri-butyl phosphine tetrafluoroborate (8.7g, 30mmol) and first
Benzene (1.5L), it is heated to reflux 24 hours, cools down under nitrogen protection, wash, dry, remove toluene, crude product crosses post and purifies to obtain
90g products, yield 57%.MS(m/z):319.1.
Intermediate 2-2 synthesis
In flask, add intermediate 2-1 (40g, 0.125mol), sodium carbonate (40g, 0.38mol), palladium (0.5g,
2.2mmol), tricyclohexyl phosphine tetrafluoroborate (1.6g, 4.4mmol) and dimethyl acetamide (0.5L), it is small to be heated to reflux 5
When, cooling, subtract and partial solvent is evaporated off, cool down, be added to the water, be extracted with ethyl acetate, dry, cross post and purify to obtain 15g productions
Product, yield 43%.MS(m/z):283.3.
The synthesis of compound 2
In three-necked flask, 2- bromo- 9,10- bis- (2- naphthyls) anthracene (0.53g, 1.05mmol), intermediate 2-2 are added
(0.30g, 1.05mmol), potassium tert-butoxide (0.22g, 2mmol), palladium (10mg), S-phos (36mg) and 30ml 1,3,5-
Trimethylbenzene, it is heated to reflux 8 hours, cools down under nitrogen protection, wash, dry, crude product is purified to obtain 0.4g productions with column chromatography
Product, yield are 53%, HRMS (m/z):711.2954, as shown in Figure 1.
Embodiment 2
The synthesis of compound 7
Intermediate 7-1 synthesis
Intermediate 2-2 (10g, 35.3mmol) is added into reaction bulb, to bromo-iodobenzene (12g, 42mmol), potassium tert-butoxide
(7.9g, 70.6mmol), palladium (0.3g, 1.3mmol), tri-butyl phosphine tetrafluoroborate (0.8g, 2.7mmol) and toluene
(150mL), it is heated to reflux 24 hours, cools down under nitrogen protection, remove toluene, add dichloromethane, wash, dry, crude product
Post is crossed, obtains 10g products, yield 57%.MS(m/z):437.0.
Intermediate 7-2 synthesis
In single-necked flask add compound 7-1 (4.37g, 10mmol), connection boric acid frequency receive alcohol ester (3.0g, 12mmol),
Potassium acetate (3.0g), the triphenylphosphine palladium of dichloro two (50mg), dioxane (60mL), 100 DEG C of reaction 12h are heated to, while hot mistake
Silica gel, filter cake is washed with dichloromethane, revolves solvent evaporated, crude product is purified with column chromatography, obtains product 2.8g, yield 60%.
MS(m/z):469.5。
The synthesis of compound 7
In flask add 2- bromo- 9,10- bis- (2- naphthyls) anthracene (0.38g, 0.75mmol), intermediate 7-2 (0.24g,
0.5mmol), tetra-triphenylphosphine palladium (50mg), 10mL 2M wet chemical, 20mL tetrahydrofuran, nitrogen protect
Under be heated to reflux 12 hours, cool down, extracted with dichloromethane, dried, concentration, crude product obtains 0.26g products by column chromatography,
Yield 66%, HRMS (m/z):783.3313, as shown in Figure 2.
Embodiment 3
The synthesis of compound 11
Intermediate 11-1 synthesis
Synthetic method is as intermediate 7-1 synthetic method, except being replaced with a bromo-iodobenzene to bromo-iodobenzene, yield
63%.MS(m/z):437.0.
Intermediate 11-2 synthesis
Synthetic method is as intermediate 7-2 synthetic method, except replacing intermediate 7-1, yield with intermediate 11-1
70%.MS(m/z):469.5.
The synthesis of compound 11
Synthetic method is as the synthetic method of compound 7, except replacing 7-2, yield 65%, HRMS with intermediate 11-2
(m/z):783.3313。
Embodiment 4
The preparation of organic electroluminescence device
OLED is prepared using the compound 2 of the embodiment of the present invention 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, PEDOT thick spin coating 50nm on ITO:(PEDOT is 3,4-ethylene dioxythiophene monomer-polymer to PSS；
PSS is poly styrene sulfonate) it is hole injection layer 130.
Then, NPB is deposited, forms the thick hole transmission layers 140 of 60nm.
Then, steaming crosses the thick compounds 2 of 40nm and is used as luminescent layer 150 on hole transmission layer.
Then, the thick TPBI of 20nm are deposited on luminescent layer as electron transfer layer 160.
Finally, evaporation 1nm LiF are electron injecting layer 170 and 100nm Al as device cathodes 180.
Prepared device (structural representation is shown in Fig. 3) is measured in 50mA/ with Photo Research PR650 spectrometers
cm2Driving current under current power be 2.0cd/A, be blue color spectrum, efficiency chart is as indicated at 4.
Embodiment 5
In addition to replacing compound 2 with compound 7, others are as the preparation method of embodiment 3.
Prepared device (structural representation is shown in Fig. 3) is measured in 50mA/ with Photo Research PR650 spectrometers
cm2Driving current under current power be 1.0cd/A, be blue color spectrum.
Embodiment 6
In addition to replacing compound 2 with compound 11, others are as the preparation method of embodiment 3.
Prepared device (structural representation is shown in Fig. 3) is measured in 50mA/ with Photo Research PR650 spectrometers
cm2Driving current under current power be 1.2cd/A, be blue color spectrum.
Comparative example 1
In addition to replacing compound 2 with MADN, others are as the preparation method of embodiment 3.
Prepared device (structural representation is shown in Fig. 3) is measured in 50mA/ with Photo Research PR650 spectrometers
Current power under cm2 driving current is 0.8cd/A, is blue color spectrum.
The structural formula of compound described in device is as follows：
Claims (8)
1. a kind of anthracene class organic electroluminescent compounds, it is characterised in that it is the compound with following structural formula I：
Wherein, Ar1And Ar2Separately selected from tolyl, phenyl, 1- naphthyls, 2- naphthyls, xenyl, fluorenyl；
Ar3Selected from singly-bound, phenyl, naphthyl, xenyl, fluorenyl；
R1And R2Separately selected from methyl, ethyl, propyl group, isopropyl, isobutyl group, normal-butyl, the tert-butyl group, n-pentyl, isoamyl
Base, n-hexyl, cyclohexyl, octyl group.
2. anthracene class organic electroluminescent compounds according to claim 1, it is characterised in that its be following structural 1-4,
6-15 compound：
3. any one of the claim 1-2 anthracene class organic electroluminescent compounds are preparing organic electroluminescence device, organic
Application in solar cell, OTFT or organophotoreceptorswith.
4. a kind of organic electroluminescence device, it includes anode, negative electrode and organic layer, and organic layer includes luminescent layer, hole is injected
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 to have
At least one layer includes anthracene compound as claimed in claim 1 in machine layer.
5. organic electroluminescence device according to claim 4, it is characterised in that the anthracene compound as described in structural formula I
The layer at place is luminescent layer.
6. organic electroluminescence device according to claim 4, it is characterised in that the anthracene compound as described in structural formula I
A kind of compound therein is used alone, or uses two or more the compound in structural formula I simultaneously.
7. organic electroluminescence device according to claim 4, it includes anode, hole transmission layer, luminescent layer, electronics and passed
Defeated layer and negative electrode, it is characterised in that the compound containing one or more kinds of structural formula I in luminescent layer.
8. organic electroluminescence device according to claim 4, it includes anode, hole transmission layer, luminescent layer, electronics and passed
Defeated layer and negative electrode, it is characterised in that contain the compound that one or more kinds of structural formulas is 1-4,6-15 in luminescent layer.
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