CN104037340B - Organic electroluminescence device - Google Patents
Organic electroluminescence device Download PDFInfo
- Publication number
- CN104037340B CN104037340B CN201410293595.4A CN201410293595A CN104037340B CN 104037340 B CN104037340 B CN 104037340B CN 201410293595 A CN201410293595 A CN 201410293595A CN 104037340 B CN104037340 B CN 104037340B
- Authority
- CN
- China
- Prior art keywords
- layer
- compound
- electroluminescence device
- organic electroluminescence
- organic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- 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
- H10K50/16—Electron transporting layers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
-
- 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
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides an organic electroluminescence device. The organic electroluminescence device comprises an anode, a cathode and an organic layer; the organic layer comprises one or more of a hole injection layer, a hole transmission layer, a lighting layer, a barrier layer, an electron injection layer and an electron transmission layer. The organic electroluminescence device is characterized in that at least one layer in the organic layer contains a compound as shown in the structural formula (I). Structural formula is as shown in the specification.
Description
Technical field
The present invention relates to field of organic electroluminescence, more particularly to a kind of organic electroluminescence device.
Background technology
Organic electroluminescence device (oleds) is to pass through 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 comprises hole transmission layer, luminescent layer
And electron transfer layer.The hole being produced by anode combines through electron transfer layer and exists with the electronics that produced by negative electrode through hole transmission layer
Luminescent layer forms exciton, then lights.Organic electroluminescence device can be adjusted as desired by the material changing luminescent layer
Section launches the light of various needs.
Organic electroluminescence device, as a kind of new Display Technique, has 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 transparent
The particular advantages such as display floater and environmental friendliness, can apply on flat-panel monitor and a new generation's illumination it is also possible to conduct
The backlight of lcd.
Since inventing at the bottom of the eighties in 20th century, organic electroluminescence device has industrially been applied, such as
As screens such as camera and mobile phones, but current oled device 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 restricting one of key factor is exactly in organic electroluminescence device
The performance of electroluminescent organic material.Additionally, due to oled device when applied voltage is run, Joule heat can be produced so that
Organic material is susceptible to crystallize, 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.
In oled material, because the speed of most electroluminescent organic material transporting holes is than the speed transmitting electronics
Hurry up, the electronics and the number of cavities that easily cause luminescent layer are uneven, and the efficiency of such device is just than relatively low.Three (8-hydroxyquinolines)
Aluminium (alq3) since invention, be extensively studied, but as its electron mobility of electron transport material still very
Low, and the intrinsic characteristic that can be degraded due to itself, with the device as electron transfer layer in it may appear that the feelings that decline of voltage
Condition, simultaneously as relatively low electron mobility is so that substantial amounts of hole enters into alq3In layer, excessive hole is with non-luminescent
Form emittance, and when as electron transport material, due to the characteristic of its green light, application receives limit
System.Therefore, development stability and there is the electron transport material of larger electron mobility, extensive to organic electroluminescence device
Using having great value.
Content of the invention
Present invention firstly provides a kind of organic electronic transport compound, it is the compound with following structural formula i:
Wherein, r1、r2、r3、r4、r5、r6、r7、r8、r9、r10、r11、r12Separately it is selected from hydrogen, D-atom, halogen, cyanogen
Base, nitro, the alkyl of c1-c12, the alkoxyl of c1-c8, the replacement of c6-c30 or the replacement of unsubstituted aryl, c3-c30
Or unsubstituted heteroaryl, c2-c8 replace or unsubstituted thiazolinyl, the replacement of c2-c8 or unsubstituted alkynyl；
l1And l2Separately it is selected from sky, singly-bound, the alkyl of c1-c6, the substituted or unsubstituted aryl of c6-c30, c3-
The replacement of c30 or unsubstituted heteroaryl；
x1、x2Separately it is selected from o, s, se, nr13；
r13For hydrogen, the alkyl of c1-c12, the replacing or unsubstituted aryl, the replacement of c3-c60 or do not take of c6-c60
The heteroaryl in generation；
Wherein preferably mode is:
r1、r2、r3、r4、r5、r6、r7、r8、r9、r10、r11、r12Separately it is selected from hydrogen, halogen, cyano group, nitro, c1-
The alkyl of c8, the alkoxyl of c1-c8, phenyl, naphthyl, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinoline
Quinoline；
l1And l2Separately be selected from sky, singly-bound, phenyl, the phenyl being replaced by c1-c4 alkyl, naphthyl, by c1-c4 alkane
The naphthyl that base replaces；
x1、x2Separately it is selected from o, s, nr13；
r13For
C1-c8 alkyl, phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9,9-
Two replacements or unsubstituted aryl) fluorenyl, 9,9- be Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, pyridine radicals, pyrimidine
Base, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinolyl；
Wherein above-mentioned phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, dibenzothiophenes base, dibenzo furan
Mutter base, pyridine radicals, pyrimidine radicals, thiadiazolyl group, triazol radical, three nitrogen piperazine bases, quinolyl can further by the alkyl of c1-c4 or
The aryl of c6-c30 is replaced；
Further preferred mode is:
r1、r2、r3、r4、r5、r6、r7、r8、r9、r10、r11、r12Separately be selected from hydrogen, fluorine, nitro, methyl, ethyl,
Propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, phenyl, naphthyl；
l1And l2Separately it is selected from sky, singly-bound, phenyl, naphthyl；
x1、x2Separately it is selected from nr13；
r13Selected from methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, by c1-c4 alkyl replace or
Unsubstituted following aryl or heteroaryl:
It is further preferred that the organic electronic transport compound of the present invention is the compound of following structural 1-52:
The organic electronic transport compound of the present invention can be anti-by suzuki coupling reaction, aldehyde radical and amino cyclic condensation
Should prepare.
The organic electronic transport compound of the present invention can be applied in organic electroluminescence device, organic solar batteries,
OTFT or organophotoreceptorswith field.
Present invention also offers a kind of organic electroluminescence device, this device comprises anode, negative electrode and organic layer, organic layer
Comprise in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer and electron transfer layer one layer or
More than one layer, at least one layer organic electronic transport compound containing as described in structural formula (i) in wherein said organic layer:
Wherein r1-r12、x1、x2And l1-l2Defined as described above.
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 stop
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 that organic electronic transport compound wherein as described in structural formula (i) is located is electron transfer layer or electronics note
Enter one or more layers in layer；
Organic electronic transport compound wherein described in structural formula (i) is the compound of structural formula 1-52；
Organic electronic transport compound as described in structural formula i can be used alone it is also possible to mix with other compounds
Use；Organic electronic transport compound as described in structural formula i can be used alone a kind of compound therein it is also possible to simultaneously
Using two or more the compound in structural formula i.
The organic electroluminescence device of the present invention, further preferred mode is that this organic electroluminescence device comprises sun
In pole, hole transmission layer, luminescent layer, electron transfer layer, hole injection layer and negative electrode, wherein electron transfer layer or electron injecting layer
Compound containing structural formula (i)；It is further preferred that the compound in electron transfer layer or electron injecting layer is structural formula
The compound of 1-52.
The organic electroluminescence device of the present invention, structural formula i compound is as can also also serve as electronics during electron transfer layer
Implanted layer.
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 when having the compound of structural formula i using the present invention, it is possible to use takes
Join other materials, such as hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and exciton barrier-layer
Deng, and obtain blue and green light, gold-tinted, ruddiness or white light.
The hole transmission layer of organic electroluminescence device of the present invention and hole injection layer, material requested has good hole
Transmission performance, can be transferred to hole luminescent layer from anode effectively.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, the miscellaneous triphen (hexanitrilehexaazatriphenylene) of six cyano group six, the fluoro- 7,7' of 2,3,5,6- tetra-, 8,
8'- tetra- cyanogen dimethyl-parabenzoquinone (f4-tcnq), 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.Following compound, including but not limited to naphthalene compounds, pyrene compound, fluorenes class chemical combination can be contained
Thing, luxuriant and rich with fragrance class compound, bend class compound, glimmering anthracene compound, anthracene compound, pentacene class compound, class compound, two
Aromatic ethylene class compound, triphenylamine ethylene compounds, aminated compounds, carbazole compound, benzimidazoles compound, furan
Class of muttering compound, metal organic fluorescence complex compound, metal Phosphorescent complex compound (such as ir, pt, os, cu), polyvinylcarbazole, poly-
The organic polymer luminescent materials such as organo-silicon compound, polythiophene, they can be used alone it is also possible to multiple mixture makes
With.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires there is good electronic transmission performance, energy
Enough effectively electronics from cathode transport to luminescent layer in, there is very big electron mobility.Except the present invention, there is structural formula i
Chemical combination beyond the region of objective existence, can also select following compound, but not limited to this, oxa- oxazole, thiazole compound, triazole chemical combination
Thing, three nitrogen piperazine class compounds, triazine class compound, quinoline class compound, phenodiazine anthracene compound, siliceous heterocyclic chemical combination
Thing, quinolines, luxuriant and rich with fragrance quinoline class compound, metallo-chelate (as alq3), fluorine substituted benzene compound, benzimidazole
Compound.
The electron injecting layer of organic electroluminescence device of the present invention, effectively can be injected into organic layer electronics from negative electrode
In, it is mainly selected from alkali metal or alkali-metal compound, or the compound selected from alkaline-earth metal or alkaline-earth metal or alkali
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；It is 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 it is also possible to use 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
Prepared by the modes such as plating method, the dip coating being dissolved in solvent, spin-coating method, stick coating method or inkjet printing.Can make for metal motor
It is prepared with vapour deposition method or sputtering method.
Experiment shows, organic electronic transport compound as described in structural formula (i) for the present invention, has preferable heat endurance,
High-luminous-efficiency, high luminance purity.Had electroluminescent using the organic electroluminescence device that this organic electronic transport compound makes
Luminous efficiency is good and excitation is excellent and the advantage of life-span length.
Brief description
Fig. 1 is the hydrogen nuclear magnetic spectrogram of compound 15.
Fig. 2 is the hydrogen nuclear magnetic spectrogram of compound 29.
Fig. 3 is a kind of organic electroluminescence device structural representation of the present invention
Wherein, 110 it is represented as glass substrate, 120 are represented as anode, 130 are represented as hole transmission layer, 140 are represented as sending out
Photosphere, 150 are represented as electron transfer layer, and 160 are represented as electron injecting layer, and 170 are represented as negative electrode.
Fig. 4 is embodiment 3 in 20ma/cm2Current density under emission spectrum.
Specific 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 15
The synthesis of compound 15-1
In there-necked flask, add phenanthrenequione (6.24g, 30mmol), the concentrated sulfuric acid (50ml), at 0 DEG C, be slowly added to nbs
(11.2g, 63mmol), reacts 2 hours, reactant liquor is poured slowly in frozen water, filters, and gained solid dimethyl sulfoxide recrystallizes
Obtain 5.6g orange solids, yield is 50%.1h nmr(400mhz,cdcl3, δ): 8.25-8.27 (d, j=8.8hz, 2h),
8.08-8.09 (d, 2h), 7.95-7.98 (dd, j=8.4hz, 2h).
The synthesis of compound 15-2
In there-necked flask, add compound 15-1 (3.66g, 10mmol), o-phenylenediamine (1.2g, 11mmol), acetic acid
(40m) with ethanol (80ml), it is heated to reflux 3 hours, cold filtration obtains 4.2g faint yellow solid, yield is 96%.1h nmr
(400mhz,cdcl3,δ):9.53-9.54(d,2h),8.34-8.40(m,4h),7.88-7.93(m,4h).
The synthesis of compound 15-3 and 15-4
Add n- phenyl -1,2- phenylenediamine (9.2g, 50mmol) and nmp (80ml, n- methyl pyrrolidone) in flask,
Add under 4- bromo-benzoyl chloride (10.9g, 50mmol) room temperature stirring reaction overnight.React, reactant liquor has been poured into water, had
A large amount of solids separate out, and filter, filter cake thf (oxolane) and recrystallizing methanol, obtained white solid (compound 15-3)
Add acetic acid (100ml) to be heated to reflux 12 hours, reacted, removal of solvent under reduced pressure, add methyl alcohol (50ml), filter, obtain 12g
White solid (compound 15-4), yield is 69%.The wherein nuclear-magnetism of 15-4 is:
1H nmr (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 compound 15-5
Under nitrogen protection, compound 15-4 (10.6g, 29mmol) and dried oxolane (100ml) are added
There-necked flask in, be cooled to -78 DEG C.Subsequently under agitation with syringe be slowly injected into 2.5 moles every liter of n-buli just oneself
Alkane solution (20ml, 50mmol), then adds triisopropyl borate ester (8.1g, 43mmol), continues stirring 1 at this temperature
Hour, then it is slowly increased to room temperature, be stirred overnight under nitrogen protection.React, watery hydrochloric acid reactant liquor being poured into 2n is molten
In liquid, and it is extracted with ethyl acetate three times, merges organic phase, use salt solution and washing successively, then use anhydrous sodium sulfate drying.Remove
Solvent, crude product ethyl acetate and n-hexane are recrystallized to give 8.3g white solid, and yield is 74%.1h nmr(400mhz,
dmso,δ):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 compound 15
In single-necked flask, add compound 15-2 (0.3g, 0.68mmol), compound 15-5 (0.6g, 1.78mmol),
Oxolane (20ml) and 2m k2co3The aqueous solution (10ml), under nitrogen protection, addition four (triphenyl phosphorus) palladium (10mg,
0.0075mmol), then it is heated to reflux 5 hours, reacted, cooling, extracted three times with dichloromethane, organic layer anhydrous slufuric acid
Sodium is dried, and rotation removes organic solvent, and crude product carries out column chromatography purification, obtains 0.4g yellow solid, and yield is 72%.1h
nmr(400mhz,cdcl3,δ):9.68(s,2h),8.65(d,2h),8.39-8.41(m,2h),8.07-8.09(m,2h),
7.80-7.98(m,12h),7.56-7.61(m,6h),7.33-7.41(m,10h).
Embodiment 2
The synthesis of compound 29
The synthesis of compound 29-2
In flask, add m-bromobenzoic acid (5.9g, 29mmol) and thionyl chloride (6ml), be heated to reflux 2 hours, cold
But, unnecessary thionyl chloride be removed under reduced pressure, add solvent nmp (n- methyl pyrrolidone, 50ml), adjacent amido diphenylamines (5.3g,
29mmol) with triethylamine (5ml), stirring at normal temperature overnight, is poured in frozen water, filtration, filter cake oxolane and recrystallizing methanol,
Gained solid adds acetic acid (50ml) to be heated to reflux 12 hours, has reacted, removal of solvent under reduced pressure, adds 25ml methyl alcohol, filters, obtains
To 7.2g white solid, yield is 71%.1h nmr(400mhz,cdcl3,δ):7.88-7.93(m,2h),7.49-7.58(m,
4h),7.29-7.40(m,6h),7.14-7.18(m,1h).
The synthesis of compound 29-3
Under nitrogen protection, compound 29-2 (3.8g, 11mmol) and dried oxolane (40ml) are added
In there-necked flask, it is cooled to -78 DEG C.Subsequently it is slowly injected into the n-buli hexane solution of 2.5m under agitation with syringe
(6.4ml, 16mmol), then adds triisopropyl borate ester (3g, 16mmol), continues stirring 1 hour at this temperature, so
After be slowly increased to room temperature, be stirred overnight under nitrogen protection.React, reactant liquor has been poured in the dilute hydrochloric acid solution of 2n, and
It is extracted with ethyl acetate three times, merges organic phase, use salt solution and washing successively, then use anhydrous sodium sulfate drying.Remove solvent, slightly
Product ethyl acetate and n-hexane are recrystallized to give 2.7g white solid, and yield is 78%.
The synthesis of compound 29
In single-necked flask, add compound 29-3 (0.31g, 1mmol), compound 15-2 (0.15g, 0.34mmol),
With oxolane (20ml) and 2m k2co3The aqueous solution (10ml), under nitrogen protection, addition four (triphenyl phosphorus) palladium (10mg,
0.0075mmol), then it is heated to reflux 5 hours, reacted, cooling, extracted three times with dichloromethane, organic layer anhydrous slufuric acid
Sodium is dried, and rotation removes organic solvent, and crude product carries out column chromatography purification, obtains 0.15g yellow solid, and yield is 54%.1h
nmr(400mhz,cdcl3, δ): 9.68 (s, 2h), 8.46-8.48 (d, j=8.8hz, 2h), 8.30-8.32 (m, 2h), 8.05
(s,2h),7.71-7.90(m,8h),7.24-7.54(m,20h).
Embodiment 3
The preparation of organic electroluminescence device
Compound 15 using embodiment 1 prepares oled
First, by electrically conducting transparent ito glass substrate 110 (carrying anode 120 above) (the limited public affairs of South China glass group share
Department) warp successively: deionized water, ethanol, acetone and deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, evaporating n pb, forms the thick hole transmission layer 130 of 60nm.
Then, the thick compound a lq of evaporation 30nm on hole transmission layer3As luminescent layer 140.
Then, the thick compound 15 of 20nm is deposited with luminescent layer as electron transfer layer 150.
Finally, it is deposited with 1nm lif for electron injecting layer 160 and 100nm al as device cathodes 170.Device architecture is as schemed
3
Prepared device is recorded in 200ma/cm with photo research pr650 spectrometer2Current density under
Efficiency is 2.2cd/a, and Fig. 4 represents the organic electroluminescence device of the present embodiment in 20ma/cm2Current density under launching light
Spectrum, is green spectral.
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) warp successively: deionized water, ethanol, acetone and deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, evaporating n pb, 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, it is deposited with 1nm lif for electron injecting layer 160 and 100nm al as device cathodes 170.
Prepared device is recorded in 200ma/cm with photo research pr650 spectrometer2Current density under
Efficiency is 1.5cd/a.
At identical conditions, the organic electroluminescence device that prepared by the organic electronic transport compound of the application present invention
Efficiency is higher than comparative example.As described above, the compound of the present invention has high stability, the organic electroluminescent of present invention preparation
Device has high efficiency and optical purity.
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 comprises hole injection layer, hole
In transport layer, luminescent layer, barrier layer, electron injecting layer and electron transfer layer more than one layer it is characterised in that in organic layer extremely
The few one layer compound including following structural formula (i):
Wherein r1、r2、r3、r4、r5、r6、r7、r8、r9、r10、r11、r12Separately it is selected from hydrogen, methyl, ethyl, propyl group, isopropyl
Base, the tert-butyl group, normal-butyl, n-hexyl；
l1And l2Separately it is selected from phenyl, naphthyl；
x1、x2Separately it is selected from nr13；
r13Selected from methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, by c1-c4 alkyl replace or do not take
The following aryl in generation:
2. organic electroluminescence device according to claim 1 is it is characterised in that the compound of structural formula (i) is following knot
The compound of structure formula:
3. organic electroluminescence device according to claim 1 is it is characterised in that compound institute as described in structural formula (i)
Layer be in electron transfer layer or electron injecting layer more than one layer.
4. organic electroluminescence device according to claim 1 is it is characterised in that compound list as described in structural formula (i)
Solely use or be used in mixed way with other compounds.
5. organic electroluminescence device according to claim 1 is it is characterised in that compound list as described in structural formula (i)
Solely use a kind of compound therein, or simultaneously using the two or more compound in structural formula (i).
6. organic electroluminescence device according to claim 1, it comprises anode, hole transmission layer, luminescent layer, electronics biography
Defeated layer, electron injecting layer and negative electrode are it is characterised in that contain the compound of structural formula (i) in electron transfer layer.
7. organic electroluminescence device according to claim 6 is it is characterised in that the structural formula that contains in electron transfer layer
I the compound of () is selected from one or more of following structural compound:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410293595.4A CN104037340B (en) | 2014-06-25 | 2014-06-25 | Organic electroluminescence device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410293595.4A CN104037340B (en) | 2014-06-25 | 2014-06-25 | Organic electroluminescence device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104037340A CN104037340A (en) | 2014-09-10 |
| CN104037340B true CN104037340B (en) | 2017-01-25 |
Family
ID=51468033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410293595.4A Active CN104037340B (en) | 2014-06-25 | 2014-06-25 | Organic electroluminescence device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104037340B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105679807B (en) * | 2016-04-15 | 2020-04-28 | 深圳市华星光电技术有限公司 | OLED display device and manufacturing method thereof |
| CN107827879B (en) * | 2017-09-14 | 2021-06-04 | 奥来德(上海)光电材料科技有限公司 | Material for flexible display, preparation method thereof and organic electroluminescent device |
| CN109096210A (en) * | 2018-09-05 | 2018-12-28 | 武汉市晟承宇科技有限公司 | Compound and application for organic electroluminescence device |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1777592A (en) * | 2003-04-18 | 2006-05-24 | 株式会社半导体能源研究所 | Quinoxaline derivatives, and organic semiconductor devices, electroluminescent devices and electronic appliances, made by using the derivatives |
| CN101003516A (en) * | 2006-01-18 | 2007-07-25 | 中国科学院化学研究所 | Dentritic pattern compound, preparation method and application |
| CN101687814A (en) * | 2007-03-29 | 2010-03-31 | 巴斯夫欧洲公司 | heterocyclic bridged biphenyls |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5593696B2 (en) * | 2007-11-08 | 2014-09-24 | コニカミノルタ株式会社 | Method for manufacturing organic electroluminescence device |
| CN103456897B (en) * | 2012-05-30 | 2016-03-09 | 京东方科技集团股份有限公司 | Organic electroluminescence device |
| CN103468243B (en) * | 2012-06-06 | 2015-08-19 | 广东阿格蕾雅光电材料有限公司 | Organic electronic material and organic electroluminescence device |
| CN103730581B (en) * | 2012-10-15 | 2016-05-18 | 乐金显示有限公司 | Organic light emitting apparatus and the organic light-emitting display device that uses it |
-
2014
- 2014-06-25 CN CN201410293595.4A patent/CN104037340B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1777592A (en) * | 2003-04-18 | 2006-05-24 | 株式会社半导体能源研究所 | Quinoxaline derivatives, and organic semiconductor devices, electroluminescent devices and electronic appliances, made by using the derivatives |
| CN101003516A (en) * | 2006-01-18 | 2007-07-25 | 中国科学院化学研究所 | Dentritic pattern compound, preparation method and application |
| CN101687814A (en) * | 2007-03-29 | 2010-03-31 | 巴斯夫欧洲公司 | heterocyclic bridged biphenyls |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104037340A (en) | 2014-09-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104030988B (en) | A kind of electron transport compound based on benzimidazole | |
| CN105481811B (en) | A kind of compound and its organic electroluminescence device with spiro structure | |
| CN104650040B (en) | A kind of organic electroluminescent compounds of azophenlyene analog derivative | |
| CN109336772A (en) | A kind of triaromatic amine compound containing spiro structure and application thereof and luminescent device | |
| CN104193738A (en) | Benzimidazole-based electronic transmission compound | |
| CN109535175A (en) | A kind of double triaromatic amine compounds, application and the luminescent device of the spiro structure containing five-membered ring | |
| CN104086447B (en) | A kind of hole transport compound based on fluorenes | |
| CN103865525B (en) | A kind of organic electroluminescent compounds | |
| CN105175314A (en) | Hole transporting compound and organic electroluminescent device thereof | |
| CN104073248B (en) | A kind of hole transport compound based on fluorenes | |
| CN104073249B (en) | A kind of organic electronic transport compound | |
| KR101401847B1 (en) | Novel compound derivative, process for preparing the same, and organic electronic device using the same | |
| CN104037340B (en) | Organic electroluminescence device | |
| CN104167498B (en) | A kind of organic electroluminescence device | |
| CN106749234A (en) | Organic electroluminescent electron transport compound and its luminescent device based on anthracene | |
| CN104037361B (en) | A kind of organic electroluminescence device | |
| KR20140021294A (en) | Novel compounds and organic light emitting device display using the same | |
| CN103887447B (en) | A kind of organic electroluminescence device | |
| CN113372289A (en) | Organic electronic material containing phenanthrene azole compound and preparation method and application thereof | |
| JP6516861B2 (en) | Organic electroluminescent material | |
| CN104638146B (en) | A kind of organic electroluminescence device | |
| CN104037339B (en) | A kind of organic electroluminescence device | |
| CN104037338B (en) | A kind of organic electroluminescence device | |
| CN108976196A (en) | A kind of aromatic amine compound of the spiro structure containing five-membered ring and application thereof and luminescent device | |
| CN107501201A (en) | A kind of spiral shell azole organic electroluminescent compounds and its organic electroluminescence device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |