CN101891673B - Organic material and application thereof in organic electroluminescence devices - Google Patents
Organic material and application thereof in organic electroluminescence devices Download PDFInfo
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- CN101891673B CN101891673B CN 200910234760 CN200910234760A CN101891673B CN 101891673 B CN101891673 B CN 101891673B CN 200910234760 CN200910234760 CN 200910234760 CN 200910234760 A CN200910234760 A CN 200910234760A CN 101891673 B CN101891673 B CN 101891673B
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- 0 C*c1ccc(-c2ccc(C)cc2)nc1 Chemical compound C*c1ccc(-c2ccc(C)cc2)nc1 0.000 description 2
- OJYAWVUBTIOZEI-UHFFFAOYSA-N Brc(cc1)cnc1-c(c1c2cccc1)c(cccc1)c1c2-c(cc1)ncc1Br Chemical compound Brc(cc1)cnc1-c(c1c2cccc1)c(cccc1)c1c2-c(cc1)ncc1Br OJYAWVUBTIOZEI-UHFFFAOYSA-N 0.000 description 1
- SYACRXBYRNYMLN-UHFFFAOYSA-N Brc1c(cccc2)c2c(-c2cccc3ccccc23)c2c1cccc2 Chemical compound Brc1c(cccc2)c2c(-c2cccc3ccccc23)c2c1cccc2 SYACRXBYRNYMLN-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention relates to an organic material and organic electroluminescence devices made of the same. The structural formula of the material is shown in the specification, wherein Ar is C6-C30 sub-polycyclic aromatic hydrocarbon, or C6-C30 polyheterocyclic aromatic hydrocarbon; and n is an integer from 1 to 3. The organic material of the invention can be used as an electronic transmission layer in the organic electroluminescence devices.
Description
Technical field
The present invention relates to a kind of novel organic materials, and the application in organic electroluminescence device, the ORGANIC ELECTROLUMINESCENCE DISPLAYS technical field belonged to.
Background technology
The electron transport material that tradition is used in electroluminescence device is Alq
3, but Alq
3Electronic mobility lower (greatly about 10
-6Cm
2/ Vs).In order to improve the electronic transmission performance of electroluminescence device, the researchist has done a large amount of exploratory study work.The LG chemistry has been reported the derivative of a series of pyrenes in the patent specification of China, be used as electric transmission and injecting material in electroluminescence device, has improved the luminous efficiency (publication number CN 101003508A) of device.The people such as Cao Yong synthesize FFF-Blm4 (J.Am.Chem.Soc.; (Communication); 2008; 130 (11); 3282-3283) as electric transmission and input horizon material (with Ba/Al and compare as negative electrode with Al separately), improve widely electronic injection and the transmission of device, improved electroluminescence efficient.Kodak is in United States Patent (USP) (publication number US 2006/0204784 and US 2007/0048545), mention the mixed electronic transport layer, adopt a kind of material of low lumo energy and another kind of electron transport material and the doping such as other materials such as metallic substance of having hanged down bright voltage to form.Based on the device of this mixed electronic transport layer, efficient and life-span etc. all is improved, but has increased the complicacy of device fabrication, is unfavorable for reducing the OLED cost.Electron transport material and/or the electron injection material of exploitation stability and high efficiency, thus bright voltage reduced, improve device efficiency, prolong device lifetime, have very important actual application value.
Desirable electron transport material should have the characteristic of following several respects: have reversible electrochemical reducting reaction; HOMO and lumo energy are suitable; Electronic mobility is high; Good film-forming property; Tg is high; Preferably can blocking hole.From the compound structure aspect, require molecule to contain the electron deficiency structural unit, have the good electronic capability of accepting; Molecular weight is enough large, guarantees to have higher Tg, thereby has good thermostability, and molecular weight can not be too large simultaneously, is beneficial to the vacuum evaporation film forming.
The compound that contains phenylpyridyl is typical electron deficiency system, has the good electronic capability of accepting.Therefore the present invention introduces phenyl ring and links to each other with the phenylpyridyl of electron deficiency on condensed ring system basis, forms to a certain degree song at space multistory and turns round, and increases its film-forming properties.Consider difficulty or ease and the Practical Performance of vacuum evaporation, its molecular weight of electron transport material of the present invention generally is no more than 800.
Based on above consideration, this patent is developed a kind of novel organic materials, and this material has good thermostability, and high electron mobility can be used as electron transfer layer in organic electroluminescence device.
Summary of the invention
The objective of the invention is to propose a kind of novel organic materials, its general structure is as follows:
In the following formula, it is 6 to 30 inferior condensed-nuclei aromatics that Ar is selected from carbonatoms, or to be selected from carbonatoms be 6 to 30 inferior fused heterocycle aromatic hydrocarbons, for example, Ar can be naphthylidene, connection naphthylidene, anthrylene, benzo anthrylene, Ya perylene base, inferior pyrenyl, phenylene pyridyl, diphenylene pyridyl,
, dibenzo
Deng; N is selected from 1 to 3 integer.
In the above-mentioned general formula, the structure of Ar is as follows when n=1:
The structure of Ar is as follows during n=2:
The structure of Ar is as follows during n=3:
The structure of the phenylpyridine group in the material general formula of the present invention is as follows:
In order more to clearly demonstrate content of the present invention, the preferred structure in the type of compounds that lower mask body narration the present invention relates to:
1, when n=1, some main electron transport material structures following (only as an example of anthracene example it is described here, the compound that other Ar residue forms is therewith in like manner):
2, when n=2, some main electron transport material structures are as follows:
6, organic materials claimed in claim 1 is used as the electric transmission layer material in organic electroluminescence device.
7, a kind of organic electroluminescence device wherein comprises pair of electrodes and is arranged on this to the organic light emitting medium between the electrode, comprises at least a kind of material claimed in claim 1 that is selected from this organic light emitting medium.
8, organic electroluminescence device according to claim 7 is characterized in that, the described material that is selected from claim 1 is arranged in the electron transfer layer of this organic light emitting medium.
3, when n=3, typical electron transport material structure is as follows:
Organic materials of the present invention is used as electron transfer layer in organic electroluminescence device.
The present invention also proposes a kind of organic electroluminescence device, comprises above-mentioned general formula compound in its organic function layer, and this compounds is as the electron transport material in the organic function layer.
Organic materials of the present invention has higher electronic mobility, can be used as electron transfer layer in display of organic electroluminescence.
Embodiment
Used various phenylpyridine boric acid among the present invention, various bromo anthracene, bromine for the basic chemical industry raw materials such as perylene, bromo pyrene, anthraquinone, benzo anthraquinone all at home Chemicals market conveniently bought, various phenylpyridine ylboronic acids all available common organic method are synthetic.
Embodiment
Compou nd synthesis method in the present invention divides work three classes: the synthetic of asymmetric compound (during n=1) all can carry out with reference to embodiment 1; Symmetrical compound and a part of asymmetric compound (during n=2) can carry out with reference to embodiment 5, embodiment 7 and embodiment 18 methods; Part symmetrical compound and a part of asymmetric compound (during n=3) can carry out with reference to embodiment 18 methods.The below sets forth the synthetic method of part main compound in this patent.
Embodiment 1 compound 1-1's is synthetic
(1) the first step reaction
The experimental equation formula
At a there-necked flask reflux condensing tube and nitrogen protection device are installed.Add 9-bromine anthracene 4g (purity 91.40%, 0.0142), 1-naphthalene boronic acids 3.18g (purity 99.0%, 0.0183mol), Palladous chloride 0.19g (purity AR, 0.0011mol), triphenylphosphine 0.58g (purity AR, 0.0022mol), salt of wormwood 6.99g (purity AR, 0.0066mol), toluene 50ml, ethanol 38ml, water 25ml wherein naphthalene boronic acids graded add.With water pump bleed the ventilation three times after, back flow reaction under nitrogen protection.
React again 2.5hr after adding the 1g naphthalene boronic acids behind the reaction 1hr, the some plate, raw material point disappears.Stopped reaction.Separatory filters with the high silicagel column of 15cm, and organic impurity does not separate.Cross post with the high silicagel column of 35cm, pure sherwood oil flushing, colour band digs out product silica gel after separating, and ethyl acetate drip washing obtains the 3.95g intermediate, and HPLC analyzes: 83.78/3.212min, pure yield 76.66%.
(2) second step reaction
Reaction equation
In the 1000ml there-necked flask, and adding the first step product 4g (purity 83.78%, 0.01102mol), cupric bromide 10g (purity AR, 0.04433mol), chlorobenzene 300ml, magnetic agitation, reflux, reaction 1.5hr, emit without obvious HBr, off-response is after the room temperature, the silicagel column high with about 10cm filters out CuBr, and toluene is washed silica gel, and decompression is spin-dried for and obtains the brown dope, add petroleum ether and stirring, obtain yellow-green colour solid 4.9g, HPLC 89.39/4.891min.Pure productive rate: 100%.Further do not process and directly drop into the next step.
(3) three-step reactions
Reaction equation
At a there-necked flask reflux condensing tube and nitrogen protection device are installed, and adding second step reaction product 7.5g (purity 89.39%, 0.01755mol); 2-phenylpyridine-4-boric acid 5.1g (purity 90.0%, 0.0228mol), Palladous chloride 0.5g (purity AR; 0.00282mol); triphenylphosphine 1.49g (purity AR, 0.005687mol), salt of wormwood 23.5g (purity AR; 0.1703mol); toluene 124ml, ethanol 80ml, water 113ml.With water pump bleed the ventilation three times after, back flow reaction under nitrogen protection.
Put plate behind the reaction 5hr, react completely stopped reaction.Let cool filtration, solid extracts with apparatus,Soxhlet's, and toluene is extracting solution, obtains the faint yellow solid product.Product is used chlorobenzene/toluene=1/10, and heat is boiled, and lets cool filtration, and this process until purity reaches more than 99%, obtains the 5.67g product, molecular weight 457, purity 99.1%, yield 70.4% repeatedly.
Product MS (m/e): 457; Ultimate analysis (C
35H
23N): theoretical value C:91.87%, H:5.07%, N:3.06%; Measured value C:91.85%, H:5.08%, N:3.07%.
Embodiment 2 compound 1-3's is synthetic
Select 9-bromine anthracene, the 1-naphthalene boronic acids, 5-phenylpyridine-3-boric acid is raw material, the three-step reaction through identical with embodiment 1 obtains compound 1-3.
Product MS (m/e): 457; Ultimate analysis (C
35H
23N): theoretical value C:91.87%, H:5.07%, N:3.06%; Measured value C:91.77%, H:5.15%, N:3.08%.
Embodiment 3 compound 1-5's is synthetic
Select 9-bromine anthracene, the 2-naphthalene boronic acids, 5-phenylpyridine-2-boric acid is raw material, the three-step reaction through identical with embodiment 1 obtains compound 1-5.
Product MS (m/e): 457; Ultimate analysis (C
35H
23N): theoretical value C:91.87%, H:5.07%, N:3.06%; Measured value C:91.87%, H:5.08%, N:3.05%.
Embodiment 4 compound 1-7's is synthetic
Select 9-bromine anthracene, the 2-naphthalene boronic acids, 5-phenylpyridine-3-boric acid is raw material, the three-step reaction through identical with embodiment 1 obtains compound 1-5.
Product MS (m/e): 457; Ultimate analysis (C
35H
23N): theoretical value C:91.87%, H:5.07%, N:3.06%; Measured value C:91.71%, H:5.18%, N:3.11%.
Embodiment 5 compound 2-1's is synthetic
(1) the first step reaction
500 milliliters of there-necked flasks are joined magnetic agitation, after the argon replaces successively by above-mentioned amount add 2-iodo-5-bromopyridine 13.4g (purity 99%, 0.0473mol), THF200ml.At-83 ℃ of lower BuLi19ml (concentration 2.5M, 0.0475mol) that drip, add immediately anthraquinone 4.8g (purity 99%, 0.023mol).After adding, naturally be warming up to room temperature, solution is glassy yellow.Add the hydrolysis of 200ml water, use ethyl acetate extraction, solvent evaporated adds acetic acid 300ml, the KI of 18g and the inferior sodium phosphate of 18g, reflux, reacted 1 hour, cooling, evaporate to dryness acetic acid, wash it with water, obtain the 5.05g yellow product, purity 87.42%, productive rate 39.19%.
(2) second step reaction
N gas protection is lower, adds 9,10-two (5-bromopyridine-2-yl) anthracene 6.0g (molecular weight 490 in-500mL there-necked flask; purity 87.42%, 0.0106mol), phenylo boric acid 3.73g (purity 98%; 0.03mol), Palladous chloride 0.21g (purity AR, 0.00124mol); triphenylphosphine 0.63g (purity AR, 0.0024mol), salt of wormwood 5.3g (purity AR; 0.0486mol); toluene 86ml, ethanol 60ml, water 72ml.Above-mentioned material, reflux is added secondary phenylo boric acid (each 1g).Stopped reaction after 4 hours lets cool, and filters, and filter cake boils filtration with toluene heat, removes catalyzer, evaporates toluene, and solid boils with water/THF of 1/10, lets cool to leach, and repeats two times.Obtain 4.1g lime look product, purity 99.14%, productive rate 77.97%.
Product MS (m/e): 484; Ultimate analysis (C
36H
24N
2): theoretical value C:89.23%, H:4.99%, N:5.78%; Measured value C:89.10%, H:5.08%, N:5.82%.
Embodiment 6 compound 2-3's is synthetic
Select anthraquinone, 2-iodo-5-bromopyridine, phenylo boric acid, the two steps reaction through identical with embodiment 5 obtains faint yellow compound 2-3.
Product MS (m/e): 484; Ultimate analysis (C
36H
24N
2): theoretical value C:89.23%, H:4.99%, N:5.78%; Measured value C:89.21%, H:5.05%, N:5.74%.
Embodiment 7 compound 2-5's is synthetic
500 milliliters of there-necked flasks are joined magnetic agitation, behind the nitrogen replacement successively by above-mentioned amount add 2-phenyl-5-bromopyridine 6.75g (purity 95.45%, 0.0274mol), THF110mol.At-70 ℃ of lower butyllithium 13ml (concentration 2.5M, 0.0325mol) that drip, stir after 10 minutes, adding anthraquinone 2.6g (purity 99%, 000124mol).After adding, naturally be warming up to room temperature, solution is glassy yellow.Add the hydrolysis of 200ml water, use ethyl acetate extraction, solvent evaporated.Add acetic acid 220ml, each 22g of KI and inferior sodium phosphate refluxes.Reacted 1 hour, cooling, cooling leaches, and gets the faint yellow product of 2.8g.Water/THF with 15/100 boiled 1 hour, let cool to leach, and is repeated multiple times, obtains 2.1g pale solid product, purity 99.0%, productive rate 20.48%.
Product MS (m/e): 484; Ultimate analysis (C
36H
24N
2): theoretical value C:89.23%, H:4.99%, N:5.78%; Measured value C:89.30%, H:5.01%, N:5.69%.
Embodiment 8 compound 2-7's is synthetic
Select anthraquinone, 2-phenyl-4-bromopyridine, the reaction through identical with embodiment 7 obtains faint yellow compound 2-7.
Product MS (m/e): 484; Ultimate analysis (C
36H
24N
2): theoretical value C:89.23%, H:4.99%, N:5.78%; Measured value C:89.22%, H:5.03%, N:5.75%.
Embodiment 9 compound 2-9's is synthetic
Select anthraquinone, 2-phenyl-4-bromopyridine, the reaction through identical with embodiment 7 obtains faint yellow compound 2-9.
Product MS (m/e): 484; Ultimate analysis (C
36H
24N
2): theoretical value C:89.23%, H:4.99%, N:5.78%; Measured value C:89.18%, H:5.03%, N:5.79%.
Embodiment 10 compound 2-11's is synthetic
Select 2,6-two (3-pyridyl) anthraquinone, 5-phenyl-2-bromopyridine, the reaction through identical with embodiment 7 obtains yellow compound 2-11.
Product MS (m/e): 484; Ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.40%, H:4.79%, N:8.81%.
Embodiment 11 compound 2-13's is synthetic
Select 2,6-two (3-pyridyl) anthraquinone, 5-phenyl-2-bromopyridine, the reaction through identical with embodiment 7 obtains yellow compound 2-13.
Product MS (m/e): 638; Ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.40%, H:4.79%, N:8.81%.
Embodiment 12 compound 2-15's is synthetic
Select the benzo anthraquinone, 4-phenyl-2-bromopyridine, the reaction through identical with embodiment 7 obtains yellow compound 2-15.
Product MS (m/e): 534; Ultimate analysis (C
40H
26N
2): theoretical value C:89.86%, H:4.90%, N:5.24%; Measured value C:89.80%, H:4.91%, N:5.29%.
Embodiment 13 compound 2-17's is synthetic
Select the benzo anthraquinone, 2-phenyl-4-bromopyridine, the reaction through identical with embodiment 7 obtains yellow compound 2-17.
Product MS (m/e): 534; Ultimate analysis (C
40H
26N
2): theoretical value C:89.86%, H:4.90%, N:5.24%; Measured value C:89.85%, H:4.82%, N:5.33%.
Embodiment 14 compound 2-19's is synthetic
Select the benzo anthraquinone, 2-phenyl-5-bromopyridine, the reaction through identical with embodiment 7 obtains yellow compound 2-19.
Product MS (m/e): 534; Ultimate analysis (C
40H
26N
2): theoretical value C:89.86%, H:4.90%, N:5.24%; Measured value C:89.70%, H:5.02%, N:5.28%.
Embodiment 15 compound 2-21's is synthetic
Select the benzo anthraquinone, 5-phenyl-2-bromopyridine, the reaction through identical with embodiment 7 obtains yellow compound 2-21.
Product MS (m/e): 584; Ultimate analysis (C
44H
28N
2): theoretical value C:90.38%, H:4.83%, N:4.79%; Measured value C:90.46%, H:4.70%, N:4.84%.
Embodiment 16 compound 2-23's is synthetic
Select phenanthrenequione, 5-phenyl-2-bromopyridine, the reaction through identical with embodiment 7 obtains yellow compound 2-23.
Product MS (m/e): 484; Ultimate analysis (C
36H
24N
2): theoretical value C:89.23%, H:4.99%, N:5.78%; Measured value C:89.40%, H:4.85%, N:5.75%.
Embodiment 17 compound 2-25's is synthetic
Select phenanthrenequione, 5-phenyl-3-bromine is given a tongue-lashing pyridine, and the reaction through identical with embodiment 7 obtains yellow compound 2-25.
Product MS (m/e): 484; Ultimate analysis (C
36H
24N
2): theoretical value C:89.23%, H:4.99%, N:5.78%; Measured value C:89.25%, H:4.88%, N:5.87%.
Embodiment 18 compound 2-27's is synthetic
N gas protection is lower, adds 3,9-2-Xiu perylene 4.32g (purity 95% in-500mL there-necked flask; 0.01mol), 6-phenylpyridine-3-boric acid 5.1g (purity 98%, 0.025mol); Palladous chloride 0.21g (purity AR, 0.0012mol), triphenylphosphine 0.63g (purity AR; 0.0024mol); salt of wormwood 5.3g (purity AR, 0.0486mol), toluene 86ml; ethanol 60ml, water 72ml.Above-mentioned material, reflux.Stopped reaction after 4 hours lets cool, and filters, and filter cake boils filtration with toluene heat, removes catalyzer, evaporates toluene, and solid boils with water/THF of 1/10, lets cool to leach, and repeats two times.Obtain 4.2g beige product, purity 99.10%, productive rate 75.26%.
Product MS (m/e): 558; Ultimate analysis (C
42H
26N
2): theoretical value C:90.29%, H:4.69%, N:5.01%; Measured value C:90.11%, H:4.88%, N:5.01%.
Embodiment 18 compound 2-29's is synthetic
Select 3,9-, 2-Xiu perylenes, 5-phenylpyridine-3-boric acid, the reaction through identical with embodiment 18 obtains yellow compound 2-29.
Product MS (m/e): 558; Ultimate analysis (C
42H
26N
2): theoretical value C:90.29%, H:4.69%, N:5.01%; Measured value C:90.11%, H:4.88%, N:5.01%.
Embodiment 19 compound 2-31's is synthetic
Select 6,12-, two-bromine to bend, 4-phenylpyridine-2-boric acid, the reaction through identical with embodiment 18 obtains yellow compound 2-31.
Product MS (m/e): 534; Ultimate analysis (C
40H
26N
2): theoretical value C:89.86%, H:4.90%, N:5.24%; Measured value C:90.01%, H:4.86%, N:5.13%.
Embodiment 20 compound 2-33's is synthetic
Select 6,12-, two-bromine to bend, 5-phenylpyridine-3-boric acid, the reaction through identical with embodiment 18 obtains yellow compound 2-33.
Product MS (m/e): 534; Ultimate analysis (C
40H
26N
2): theoretical value C:89.86%, H:4.90%, N:5.24%; Measured value C:89.80%, H:4.93%, N:5.27%.
Embodiment 21 compound 2-35's is synthetic
Select 1,6-, two-bromine pyrene, 4-phenylpyridine-2-boric acid, the reaction through identical with embodiment 18 obtains yellow compound 2-35.
Product MS (m/e): 508; Ultimate analysis (C
38H
24N
2): theoretical value C:89.74%, H:4.76%, N:5.51%; Measured value C:89.81%, H:4.70%, N:5.49%.
Embodiment 22 compound 2-37's is synthetic
Select 1,6-, two-bromine pyrene, 2-phenylpyridine-4-boric acid, the reaction through identical with embodiment 18 obtains yellow compound 2-37.
Product MS (m/e): 508; Ultimate analysis (C
38H
24N
2): theoretical value C:89.74%, H:4.76%, N:5.51%; Measured value C:89.70%, H:4.81%, N:5.49%.
Embodiment 23 compound 2-39's is synthetic
Select 1,6-, two-bromine pyrene, 5-phenylpyridine-2-boric acid, the reaction through identical with embodiment 18 obtains yellow compound 2-39.
Product MS (m/e): 508; Ultimate analysis (C
38H
24N
2): theoretical value C:89.74%, H:4.76%, N:5.51%; Measured value C:89.68%, H:4.71%, N:5.61%.
Embodiment 24 compound 2-41's is synthetic
Select 4,9-, two-bromonaphthalene and thiadiazoles, 6-phenylpyridine-3-boric acid, the reaction through identical with embodiment 18 obtains red compound 2-41.
Product MS (m/e): 492; Ultimate analysis (C
32H
20N
4S): theoretical value C:78.02%, H:4.09%, N:11.37%, S:6.51%; Measured value C:78.10%, H:4.06%, N:11.42%, S:6.42%.
Embodiment 25 compound 2-42's is synthetic
Select 4,9-, two-bromonaphthalene and thiadiazoles, 5-phenylpyridine-3-boric acid, the reaction through identical with embodiment 18 obtains red compound 2-42.
Product MS (m/e): 492; Ultimate analysis (C
32H
20N
4S): theoretical value C:78.02%, H:4.09%, N:11.37%, S:6.51%; Measured value C:78.05%, H:4.10%, N:11.40%, S:6.45%.
Embodiment 26 compound 3-1's is synthetic
Select 1,3,5-, three bromonaphthalenes, 5-phenylpyridine-2-boric acid, the reaction through identical with embodiment 18 obtains faint yellow compound 3-1.
Product MS (m/e): 587; Ultimate analysis (C
43H
29N
3): theoretical value C:87.88%, H:4.97%, N:7.15%; Measured value C:87.81%, H:4.95%, N:5.24%.
Embodiment 27 compound 3-3's is synthetic
Select 4,6,8-, three bromoquinolines, 5-phenylpyridine-2-boric acid, the reaction through identical with embodiment 18 obtains yellow compound 3-3.
Product MS (m/e): 588; Ultimate analysis (C
42H
28N
4): theoretical value C:85.69%, H:4.79%, N:9.52%; Measured value C:85.72%, H:4.85%, N:9.43%.
The below is the Application Example of the compounds of this invention:
Embodiment 28: the preparation of electroluminescence device and result
The preferred implementation of fabricate devices:
(1) designs
For the convenient relatively transmission performance of these electron transport materials, the present invention has designed a simple electroluminescence device (substrate/anode/hole transmission layer (HTL)/organic luminous layer (EL)/electron transfer layer (ETL)/negative electrode), only use compound 2-1 and 2-5 as the electron transport material illustration, efficent electronic transport material Bphen is material as a comparison, (EM1 is material of main part to EM1 as the luminescent material illustration, it is not luminescent material, purpose is not to pursue high-level efficiency, but verifies the possibility of these material practicalities).The structure of Bphen and EM1 is:
Substrate can use the substrate in traditional organic luminescent device, for example: glass or plastics.Select glass substrate in element manufacturing of the present invention, ITO makes anode material.
Hole transmission layer can adopt various tri-arylamine group materials.Selected hole mobile material is NPB in element manufacturing of the present invention.
Negative electrode can adopt metal and composition thereof structure, such as Mg:Ag, Ca:Ag etc., also can be electron injecting layer/metal-layer structure, such as LiF/Al, Li
2The common cathode construction such as O.Selected electron injection material is LiF in element manufacturing of the present invention, and cathode material is Al.
(2) element manufacturing
Sheet glass supersound process in commercial clean-out system of ITO transparency conducting layer will be coated with, wash in deionized water, at acetone: ultrasonic oil removing in the alcohol mixed solvent is baked under clean environment and removes moisture content fully, with UV-light and ozone clean, and with low energy positively charged ion bundle bombarded surface;
Above-mentioned glass substrate with anode is placed in the vacuum chamber, be evacuated to 1 * 10
-5～9 * 10
-3Pa, vacuum evaporation NPB is as hole transmission layer on above-mentioned anode tunic, and evaporation speed is 0.1nm/s, and the evaporation thickness is 50nm;
Vacuum evaporation EM1 or EM2 are as the luminescent layer of device on hole transmission layer, and evaporation speed is 0.1nm/s, and the evaporation total film thickness is 30nm;
Vacuum evaporation one deck compound 1-7 or 2-7 be as the electron transfer layer of device on luminescent layer, and other adopts Bphen of the prior art as the electron transfer layer of device as a comparison case, and its evaporation speed is 0.1nm/s, and the evaporation total film thickness is 50nm;
At the negative electrode of the upper vacuum evaporation Al layer of electron transfer layer (ETL) as device, thickness is 150nm.
Device performance see the following form (device architecture: ITO/NPB (40nm)/EM1 (30nm)/ETL material (20nm)/LiF (0.5nm)/Al (150nm))
| The embodiment numbering | The ETL material | Require brightness cd/m2 | Voltage V | Current density A/m2 | Electric current mA | Current efficiency cd/A | Luminous efficiency 1m/W |
| Embodiment 1 | Compound 1-7 | 1000.00 | 5.74 | 825.0 | 7.4 | 1.21 | 0.66 |
| Embodiment 2 | Compound 2-7 | 1000.00 | 6.17 | 1047.68 | 9.4 | 0.95 | 0.49 |
| Comparative Examples | Bphen | 1000.00 | 6.28 | 1008.97 | 9.1 | 0.99 | 0.50 |
Above result shows that novel organic materials of the present invention can be preferably used as electron transfer layer in organic electroluminescence device.
Although describe the present invention in conjunction with the embodiments, the present invention is not limited to above-described embodiment, should be appreciated that those skilled in the art can carry out various modifications and improvement under the guiding of the present invention's design, and claims have been summarized scope of the present invention.
Claims (5)
1. organic materials, its general structure is as follows:
In the following formula, n is 1 or 2;
The structure of Ar is as follows during n=1:
The structure of Ar is as follows during n=2:
2. organic materials claimed in claim 1, structural formula is as follows:
3. organic materials claimed in claim 1 is used as the electric transmission layer material in organic electroluminescence device.
4. an organic electroluminescence device wherein comprises pair of electrodes and is arranged on this to the organic light emitting medium between the electrode, comprises at least a kind of material claimed in claim 1 that is selected from this organic light emitting medium.
5. organic electroluminescence device according to claim 4 is characterized in that, the described material that is selected from claim 1 is arranged in the electron transfer layer of this organic light emitting medium.
Priority Applications (7)
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| CN 200910234760 CN101891673B (en) | 2009-11-13 | 2009-11-13 | Organic material and application thereof in organic electroluminescence devices |
| PCT/CN2009/076276 WO2011057461A1 (en) | 2009-11-13 | 2009-12-30 | Organic materials and organic electroluminescent apparatuses using the same |
| PL09851216T PL2500343T3 (en) | 2009-11-13 | 2009-12-30 | Organic materials and organic electroluminescent apparatuses using the same |
| US13/497,131 US9412951B2 (en) | 2009-11-13 | 2009-12-30 | Organic materials and organic electroluminescent apparatuses using the same |
| JP2012527175A JP5498580B2 (en) | 2009-11-13 | 2009-12-30 | ORGANIC MATERIAL AND ORGANIC EL DEVICE USING THE MATERIAL |
| EP09851216.3A EP2500343B1 (en) | 2009-11-13 | 2009-12-30 | Organic materials and organic electroluminescent apparatuses using the same |
| KR1020127004954A KR101411122B1 (en) | 2009-11-13 | 2009-12-30 | Organic material and organic EL device using the same material |
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| WO2015101257A1 (en) | 2013-12-31 | 2015-07-09 | 北京维信诺科技有限公司 | Organic electroluminescent and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2012070535A1 (en) * | 2010-11-25 | 2012-05-31 | Jnc株式会社 | Electron transport material, and organic electroluminescent element using same |
| CN103579528B (en) * | 2012-07-31 | 2016-03-30 | 昆山维信诺显示技术有限公司 | Electron transfer layer, containing the organic electroluminescence device of this electron transfer layer and preparation |
| CN102916134B (en) * | 2012-10-31 | 2016-06-29 | 昆山维信诺科技有限公司 | Electron transfer layer, organic electroluminescence device containing this layer and manufacture method thereof |
| CN103794731A (en) * | 2013-12-31 | 2014-05-14 | 北京维信诺科技有限公司 | Organic light-emitting display device and organic light-emitting display thereof |
| CN103762318B (en) * | 2013-12-31 | 2017-01-18 | 昆山工研院新型平板显示技术中心有限公司 | Top emission OLED device |
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| CN1362464A (en) * | 2002-01-15 | 2002-08-07 | 清华大学 | Organic electroluminescent material |
| CN101077971A (en) * | 2006-05-25 | 2007-11-28 | 清华大学 | Organic electroluminescent phosphorescence luminescent material and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1362464A (en) * | 2002-01-15 | 2002-08-07 | 清华大学 | Organic electroluminescent material |
| CN101077971A (en) * | 2006-05-25 | 2007-11-28 | 清华大学 | Organic electroluminescent phosphorescence luminescent material and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2015101257A1 (en) | 2013-12-31 | 2015-07-09 | 北京维信诺科技有限公司 | Organic electroluminescent and preparation method thereof |
| US10256417B2 (en) | 2013-12-31 | 2019-04-09 | Beijing Visionox Technology Co., Ltd. | Organic electroluminescent and preparation method thereof |
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