CN101407493B - Organic material and use thereof in organic EL device - Google Patents
Organic material and use thereof in organic EL device Download PDFInfo
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- CN101407493B CN101407493B CN2008101136732A CN200810113673A CN101407493B CN 101407493 B CN101407493 B CN 101407493B CN 2008101136732 A CN2008101136732 A CN 2008101136732A CN 200810113673 A CN200810113673 A CN 200810113673A CN 101407493 B CN101407493 B CN 101407493B
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- 239000011368 organic material Substances 0.000 title claims abstract description 15
- 239000000463 material Substances 0.000 claims abstract description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 22
- 238000005401 electroluminescence Methods 0.000 claims description 20
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 11
- 125000004653 anthracenylene group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 17
- 230000005540 biological transmission Effects 0.000 abstract description 11
- 125000006615 aromatic heterocyclic group Chemical group 0.000 abstract description 3
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 239000011159 matrix material Substances 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 41
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 229910052757 nitrogen Inorganic materials 0.000 description 35
- 239000000047 product Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 238000003756 stirring Methods 0.000 description 23
- 229910052739 hydrogen Inorganic materials 0.000 description 22
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 15
- 239000012265 solid product Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- -1 heterocycle aromatic hydrocarbons Chemical class 0.000 description 13
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- 238000006243 chemical reaction Methods 0.000 description 12
- 239000002994 raw material Substances 0.000 description 12
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- 238000004458 analytical method Methods 0.000 description 11
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- 230000008020 evaporation Effects 0.000 description 9
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- 238000010189 synthetic method Methods 0.000 description 8
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 8
- WFKJYSOCZZVMEP-UHFFFAOYSA-N 4-bromobenzo[e][1,2,3]benzothiadiazole Chemical class Brc1cc2ccccc2c2nnsc12 WFKJYSOCZZVMEP-UHFFFAOYSA-N 0.000 description 7
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- 239000004327 boric acid Substances 0.000 description 7
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- 238000010992 reflux Methods 0.000 description 4
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- NTZCFGZBDDCNHI-UHFFFAOYSA-N 2-phenylanthracene-9,10-dione Chemical compound C=1C=C2C(=O)C3=CC=CC=C3C(=O)C2=CC=1C1=CC=CC=C1 NTZCFGZBDDCNHI-UHFFFAOYSA-N 0.000 description 1
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- AJZDHLHTTJRNQJ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[2-(tetrazol-1-yl)ethyl]benzamide Chemical compound N1(N=NN=C1)CCNC(C1=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)=O AJZDHLHTTJRNQJ-UHFFFAOYSA-N 0.000 description 1
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
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- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
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- 229910000474 mercury oxide Inorganic materials 0.000 description 1
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- Pyridine Compounds (AREA)
Abstract
The invention relates to an organic material and an organic light-emitting device containing the material. The structural formula of the material is shown in the right, wherein, Ar is chosen from sub-polycyclic aromatic hydrocarbon with 6-30 of carbon atoms or is chosen from sub-fused heterocyclic aromatic hydrocarbon with 6-30 of carbon atoms; R1-R8 are respectively and independently chosen fromalkyl with 1-4 of hydrogen atoms and carbon atoms, aromatic group with 6-24 carbon atoms, heterocyclic aryl with 6-24 carbon atoms; and n is chosen from integers of 2 to 4. The organic material can be used as electronic transmission matrix in the organic light-emitting device.
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.People such as Yang Yang in electroluminescence device with nano level carbonic acid caesium as electric transmission and injecting material, improved device luminous efficiency (Advanced Functional Materials, 2007,17,1966-1973).People such as Cao Yong synthesize FFF-Blm4 (structure as follows) (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), improved the electronics injection of device widely and transmitted, improved electroluminescence efficient; People such as Cao Yong also use air and variousization
The structure of FFF-Blm4
Learn all stable gold of corrosion as efficent electronic injection type cathode material, improved electroluminescence device the electronics injectability (Organic Electronics, 6 (2005), 118-128).Kodak is in United States Patent (USP) (publication number US2006/0204784 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 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.The electron transport material and/or the electronics injecting material of exploitation stability and high efficiency, thus bright voltage reduced, improve device efficiency, prolong device lifetime, have very important application value.
The ideal electron transport material should have the characteristic of following several respects: have the reversible electrochemical reducting reaction; HOMO and lumo energy are suitable; The electronic mobility height; Good film-forming property; The Tg height; Preferably can blocking hole.From the compound structure aspect, require molecular configuration near the plane, the π when increasing molecular stacks between the molecule-π interacts, and requires molecular structure plane fully simultaneously, prevents because molecular crystal influences film forming properties; Require molecule to contain the electron deficiency structural unit, have the good electronic capability of accepting; Molecular weight is enough big, guarantees to have higher Tg, thereby has good thermostability, and molecular weight can not be too big simultaneously, is beneficial to the vacuum evaporation film forming.
The compound that contains pyridyl is typical electron deficiency system, has the good electronic capability of accepting; The plane regularity of condensed-nuclei aromatics is better, and the condensed ring system is big more, and planarity is good more, and the π-π track that helps molecule more piles up and forms electron channel.But too big condensed ring system then easily makes molecule form crystallization and is difficult for film forming, so the present invention introduces phenyl ring and link to each other with the pyridyl of electron deficiency on condensed ring system basis, forms to a certain degree song and turn round on space multistory, increases its film-forming properties.Consider the 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:
Wherein, 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; R
1-R
8Be independently selected from hydrogen atom, carbonatoms respectively and be 1 to 4 alkyl, carbonatoms and be 6 to 24 aromatic group, carbonatoms and be 6 to 24 heterocyclic aromatic base; N is selected from 2 to 4 integer.
Shown in compound structure general formula of the present invention is specific as follows:
Wherein, 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; N is selected from 2 to 4 integer.
In the above-mentioned general formula Ar preferably from naphthylidene, connection naphthylidene, anthrylene, Ya perylene base, inferior pyrenyl, quinolinediyl, connection quinolinediyl,
, dibenzo
In order more to clearly demonstrate content of the present invention, the preferred structure in the type of compounds that following mask body narration the present invention relates to:
L, n are 2 o'clock
2, n is 3 o'clock
3, n is 4 o'clock
Organic materials of the present invention is used as electron transfer layer in organic electroluminescence device.
The present invention also protects a kind of organic electroluminescence device, wherein comprises pair of electrodes and is arranged on organic light emitting medium between this counter electrode, comprises a kind of material that is selected from following general structure in this organic light emitting medium at least:
Wherein, 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; R
1-R
8Be independently selected from hydrogen atom, carbonatoms respectively and be 1 to 4 alkyl, carbonatoms and be 6 to 24 aromatic group, carbonatoms and be 6 to 24 heterocyclic aromatic base; N is selected from 2 to 4 integer.
Organic materials of the present invention has higher electronic mobility, can be used as electron transfer layer in display of organic electroluminescence.
Description of drawings
The hole transport performance measurement result of Fig. 1 compound 1-1.
The electronic transmission performance measurement result of Fig. 2 compound 1-1.
Fig. 3 electroluminescence efficiency diagram (reference Alq3, in figure 1-1 represent compound 1-1) of compound 1-1 as the electroluminescence device of electron transfer layer preparation
Fig. 4 voltage and the current density graph of a relation (reference Alq3, in figure 1-1 represent compound 1-1) of compound 1-1 as the electroluminescence device of electron transfer layer preparation
Embodiment
It is from 3-(to bromophenyl) pyridine that organic materials of the present invention has all been used in building-up process.
One, the preparation of intermediate 3-(to bromophenyl) pyridine and boric acid thereof
1,3-pyridine boric acid is synthetic
Under the Ar gas shiled; 200ml toluene and 50mlTHF are chilled to-70 ℃; (concentration is 2.86M to the BuLi of adding 60ml; be total to 0.171mol); slowly drip 3-bromopyridine 16.38ml (d=1.639, molecular weight 157,0.171mol altogether) (using the 20ml dilution with toluene) down at-70 ℃; stir half an hour, be warming up to naturally about-30 ℃.Again be chilled to-70 ℃, drip 46ml triisopropyl boric acid ester (d=0.815, molecular weight 188,0.199mol altogether), heat up naturally stirring after 2 hours temperature rise to 10 ℃.
The HCl that adds 160ml2.7N stirs, and separatory is collected water layer.Organic layer extracts once with the HCl of 50ml2.7N, and 20ml water extracts once again, combining water layer.Have a large amount of light white little yellow mercury oxides to separate out when being neutralized to pH=7 with dense NaOH, filter, oven dry obtains the light white little yellow solid product of 16.8g, productive rate 79.87%, purity 93.68%.
If replace the 3-bromopyridine with 2-methyl-5-bromopyridine, can obtain corresponding 2-methyl-5-pyridine boric acid white solid product.
2, which alcohol ester of 3-pyridine boric acid Knit-the-brows is synthetic
Add the toluene of which pure and mild 300ml of Knit-the-brows of 15g in 15g3-pyridine boric acid, reflux water-dividing is approximately used 3 hours.In solid, add the 70ml sherwood oil behind the evaporate to dryness toluene and refluxed 15 minutes, thoroughly cooling, the pale solid product is separated out, and filters, and oven dry obtains the 21.7g product, productive rate 86.8%, purity 98.7%.
3,3-(4-bromophenyl) pyridine is synthetic
Under nitrogen protection, in a reaction flask, add 4.10g gram 3-pyridine boric acid Knit-the-brows any alcohol ester (molecular weight 205,0.02mol altogether) successively; 5.66g to bromo-iodobenzene (molecular weight 282.9; be total to 0.02mol), 0.266g gram Palladous chloride (molecular weight 177.4,0.0015mol altogether); 0.9825 gram triphenylphosphine (molecular weight 262; be total to 0.00375mol), 6.36g yellow soda ash, 32 milliliters of toluene; 32 milliliter of 95% ethanol, 16 ml waters.Stirring is warming up to backflow, with TLC board monitoring reaction process.React after 4 hours, cooling slightly adds 100ml toluene, removes by filter catalyzer, and 20ml toluene is washed solid.Separatory, organic layer washes it with water, and water layer is again with ethyl acetate extraction once.Merge organic layer, evaporate to dryness adds 100 ml waters, and the dense HCl of 20ml fully shakes, and product changes water layer over to, and the impurity that will be insoluble to acid with ethyl acetate proposes separatory.Water layer is neutralized to more than the pH=8 with NaOH, uses the ethyl acetate extraction product.Evaporate to dryness obtains oily product 3.13g, productive rate 67.17%, purity 97.70%.
4,3-(3-bromophenyl) pyridine is synthetic
Under nitrogen protection, in a reaction flask, add 4.10g gram 3-pyridine boric acid Knit-the-brows any alcohol ester (molecular weight 205,0.02mol altogether) successively; a 5.66g bromo-iodobenzene (molecular weight 282.9; be total to 0.02mol), 0.266g gram Palladous chloride (molecular weight 177.4,0.0015mol altogether); 0.9825 gram triphenylphosphine (molecular weight 262; be total to 0.00375mol), 6.36g yellow soda ash, 32 milliliters of toluene; 32 milliliter of 95% ethanol, 16 ml waters.Stirring is warming up to backflow, with TLC board monitoring reaction process.React after 4 hours, cooling slightly adds 100ml toluene, removes by filter catalyzer, and 20ml toluene is washed solid.Separatory, organic layer washes it with water, and water layer is again with ethyl acetate extraction once.Merge organic layer, evaporate to dryness adds 100 ml waters, and the dense HCl of 20ml fully shakes, and product changes water layer over to, and the impurity that will be insoluble to acid with ethyl acetate proposes separatory.Water layer is neutralized to more than the pH=8 with NaOH, uses the ethyl acetate extraction product.Evaporate to dryness obtains oily product 3.96g, productive rate 85.52%, and purity 94.61% is purified (with ethyl acetate/petroleum ether=1/2 drip washing) with column chromatography, obtains the faint yellow oily product of 3.78g, purity 96.78%.
5,4-(3-pyridyl) phenylo boric acid is synthetic
Under the Ar gas shiled; the anhydrous diethyl ether that in a 500mL there-necked flask, adds 160ml; be chilled to-78 ℃; stir BuLi (the concentration 2.9M that adds 25ml down; 0.0725mol); the solution that 3-(4-bromophenyl) pyridine 11.7g (content 97.70%, molecular weight 234,0.0488mol altogether) is dissolved in the 200ml ether drips wherein down at-78 ℃.After finishing, stirred 1 hour, be warming up to-20 ℃ naturally.Be cooled to-78 ℃ once more, drip 10ml (0.111mol) trimethyl borate, stir naturally and be warming up to room temperature, at room temperature stir 30min again.With NaOH and 3 hydrolysis of 50ml moisture of the 0.5M of 50ml with extract the aryl boric acid sodium that generates, united extraction liquid, if organic ether impurity enters water layer, available ether is counter to be extracted.Water layer is neutralized to pH=6 with dense HCl, has a large amount of white aryl boric acids to separate out.Filter, oven dry obtains the 5.0g product.Productive rate 51.22%, purity 92.39%.
6,3-(3-pyridyl) phenylo boric acid is synthetic
Building-up process obtains the 4.5g product with 5.Productive rate 46.10%, purity 94.30%.
Two, embodiment
Under the Ar gas shiled; in a 500mL there-necked flask, add 3-(4-bromophenyl) pyridine 3.42g (molecular weight 234; 0.01385mol); the THF of 50ml is chilled to-78 ℃, stirs to add 5.35ml (concentration 2.8M down; 0.014mol) BuLi (with the THF of 20ml dissolving); add with 30min, solution is black, stirs 30min down at-78 ℃.
Under-78 ℃, anthraquinone 1.25g (0.0058mol) solid is added wherein, add 20mlTHF.After finishing, stir naturally and be warming up to room temperature, at room temperature stir 2hr again.The water that adds 200ml stirs.Use ethyl acetate extraction, the evaporate to dryness ethyl acetate.Add 45ml acetate, 4.2gKI, 4.2g inferior sodium phosphate in the solid.Stir reflux down, solution is very fast to be reddened by brown, becomes cream colour, precipitation again.After stirring 1hr, filter, wash with acetate, washing, 30% ethanol water stirs lotion, and filtering drying obtains faint yellow solid 2.8g, purity 97.68%, productive rate about 100%.
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:89.20%, H:4.97%, N:5.83%.
Compound 1-21's is synthetic identical therewith, just the 3-in the raw material (4-bromophenyl) pyridine is changed to 3-(3-bromophenyl) pyridine and gets final product, and product is a faint yellow solid.
Reaction process is same as embodiment 1, just the raw material anthraquinone is changed to 2-phenyl anthraquinone, obtains the faint yellow solid product.
Product MS (m/e): 560; Ultimate analysis (C
42H
28N
2): theoretical value C:89.97%, H:5.03%, N:5.00%; Measured value C:89.95%, H:5.01%, N:5.04%.
Embodiment 3 compound 1-5's is synthetic
(1) the class anthraquinone ring is synthetic
In a reaction flask, add 10gN-phenyl-2,5-dimethyl pyrrole, the anhydrous AlCl of 2g
3(molecular weight 133 0.015mol), stirs, and maintains the temperature at about 80 ℃, slowly drip the 1.06g Tetra hydro Phthalic anhydride (molecular weight 148,0.007mol).Finished insulated and stirred 2 hours.Pour into immediately in the frozen water that contains a little HCL after cold slightly, the solid product washing secondary that obtains, the column chromatography separation obtains target intermediate 1.75g, productive rate 80.0%, Ms analyzes 319, meets.
Above-mentioned 1.75g product is added in the dry reaction bottle, add the 6g vitriol oil again, be heated to about 145 ℃ under stirring and be incubated 1 hour, about 170 ℃, be incubated 4 hours again.In the impouring trash ice, filter under stirring cold slightly back, washing, and buck is washed, washing, drying.Obtain yellow solid product 1.52g, productive rate 90.0%.
Product MS (m/e): 301; Ultimate analysis (C
20H
15NO
2): theoretical value C:79.72%, H:5.02%, N:4.65%, O:10.62%; Measured value C:79.80%, H:5.01%, N:4.58%.
(2) compound 1-5's is synthetic
Reaction process is same as embodiment 1, just the raw material anthraquinone is changed to above-mentioned class anthraquinone ring compound, obtains yellow solid product.
Product MS (m/e): 577; Ultimate analysis (C
42H
28N
2): theoretical value C:87.32%, H:5.41%, N:7.27%; Measured value C:87.28%, H:5.50%, N:7.22%.
(1) the class anthraquinone ring is synthetic
Synthetic method is same as embodiment 3 (1), and just with raw material N-phenyl-2, the 5-dimethyl pyrrole is changed to 2, and the 5-thioxene obtains yellow solid product.
(2) compound 1-7's is synthetic
Synthetic method is same as embodiment 1, just the raw material anthraquinone is changed to embodiment 4 (1) products, obtains yellow solid product.
Product MS (m/e): 518; Ultimate analysis (C
36H
26N
2S): theoretical value C:83.36%, H:5.05%, N:5.40%, S:6.18%; Measured value C:83.38%, H:5.020%, N:5.42%.
Compound 1-8,1-9 and 1-10 are available synthetic with quadrat method, just according to the difference of product structure, change starting raw material.
(1) 1,4-two bromo-2,3-diaminonaphthalene synthetic
(2) 4,9-two bromo-naphtho-thiadiazoles are synthetic
At N
2Protection in a there-necked flask, adds 30ml chloroform, 12ml pyridine and 5ml thionyl chloride (0.067mol) down, the ice bath cooling.Under vigorous stirring, drip the solution of 3.2g (0.01mol) A in the 100ml chloroform, solution becomes red-brown, and about 0.5h drips off.Dropwise, stir 1h under the ice bath cooling, stirring at room 2h refluxes and stirs 2h.Reaction finishes, and is spin-dried for all solvents, gets brown solid.With toluene/sherwood oil (1/1) is eluent, column chromatography separate orange red solid B, HPLC analyzes 95.6%, productive rate: 71.4%.
(2) compound 1-11's is synthetic
Reflux condensing tube and nitrogen protection device are installed on a there-necked flask.Under nitrogen protection, add: 1g (2.76mmol) 4,9-two bromo-naphtho-thiadiazoles, 1.37g (6.9mmol) 4-(3-pyridyl) phenylo boric acid, 0.097g (0.276 * 2mmol) PdCl
2, 0.289g (0.276 * 4mmol) PPh
3, 4.57g (2.76 * 12mmol) K
2CO
3Bleed after the ventilation five times with water pump, add 45ml water, 30ml ethanol and 48ml toluene.With water pump bleed the ventilation five times after, back flow reaction 24h under nitrogen protection.
Put to room temperature reaction flask is put more than the freezing 4h of refrigerator.Suction filtration, solid water, hot water wash, oven dry solid.Solid dissolves with toluene, heating, heat filtering.It is freezing that filtrate concentrates rearmounted refrigerator, filter the red solid product.
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:3.92%, N:11.40%.
Synthetic method is same as embodiment 5 (2), and just with raw material 4,9-two bromo-naphtho-thiadiazoles are changed to 2,3-phenylbenzene-4, and 9-dibromo benzo (1,2-g) quinoxaline obtains yellow solid product.
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:86.50%, H:4.77%, N:8.72%.
Synthetic method is same as embodiment 5 (2), and just with raw material 4,9-two bromo-naphtho-thiadiazoles are changed to 5,5 '-dibromo 8, and 8 ' diquinolyl obtains the faint yellow solid product.
Product MS (m/e): 562; Ultimate analysis (C
40H
26N
4): theoretical value C:85.38%, H:4.66%, N:9.96%; Measured value C:85.49%, H:4.53%, N:9.98%.
Synthetic method is same as embodiment 5 (2), and just with raw material 4,9-two bromo-naphtho-thiadiazoles are changed to 2, and 7-dibromo pyrene obtains little yellow solid product.
Product MS (m/e): 508; Ultimate analysis (C
38H
24N
2): theoretical value C:89.74%, H:4.76%, N:5.50%; Measured value C:89.79%, H:4.70%, N:5.51%.
Embodiment 9 compound 1-19's is synthetic
Synthetic method is same as embodiment 5 (2), and just with raw material 4,9-two bromo-naphtho-thiadiazoles are changed to 6, and 12-dibromo chrysene obtains little yellow solid product.
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:89.82%, H:4.86%, N:5.32%.
Synthetic method is same as embodiment 5 (2), and just with raw material 4,9-two bromo-naphtho-thiadiazoles are changed to 3,5, and 8-three bromoquinolines obtain yellow solid product.
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:85.63%, H:4.82%, N:9.55%.
All the other compounds among the present invention, for example compound 2-2, compound 2-3, compound 2-4, compound 3-1 etc. are to select corresponding many bromo-derivatives for use, and are synthetic in this way.
Synthesizing of 3-among the present invention (3-pyridyl) phenyl derivatives, for example compound 1-21 to compound 1-28, compound 2-5 to compound 2-7, compound 3-2 etc., identical with top synthetic method, just the 3-in the raw material (4-bromophenyl) pyridine is changed to 3-(3-bromophenyl) pyridine and gets final product.
Be the Application Example of The compounds of this invention below:
Embodiment 11: the hole transport performance of measuring compound 1-1
Solid film method with evaporation is measured, and voltage is 20V, hole mobility 1.07*10
-3Cm
2/ Vs, concrete measurement result is seen accompanying drawing 1.
Embodiment 12: the electronic transmission performance of measuring compound 1-1
Solid film method with evaporation is measured, and voltage is 20V, electronic mobility 8.22*10
-3Cm
2/ Vs, concrete determination data is seen accompanying drawing 2.
The preferred implementation of fabricate devices:
The typical structure of OLED device is: substrate/anode/hole transmission layer (HTL)/organic luminous layer (EL)/electron transfer layer (ETL)/negative electrode.
Substrate can use the substrate in traditional organic luminescent device, for example: glass or plastics.Anode material can adopt transparent high conductivity material, indium tin oxygen (ITO) for example, indium zinc oxygen (IZO), tindioxide (SnO
2), zinc oxide (ZnO) etc.Select glass substrate for use in element manufacturing of the present invention, ITO makes anode material.
Hole transmission layer can adopt N, N '-two (3-tolyl)-N, N '-phenylbenzene-[1, the 1-xenyl]-4,4 '-diamines (TPD) or N, N '-phenylbenzene-N, N '-two (1-naphthyl)-(1,1 '-xenyl)-4,4 '-diamines tri-arylamine group materials such as (NPB).Selected hole mobile material is NPB in element manufacturing of the present invention.
Device architecture can also can be the multi-luminescent layer structure for the single-shot photosphere; Every layer of luminescent layer can also can be doped structure for single-shot light body luminescent material structure; Luminescent dye can select for use fluorescent material also can select phosphor material for use; Glow color is not limit, can for as red, yellow, blue, green etc.Selected luminescent material is BH04 in element manufacturing of the present invention.
The electric transmission layer material uses Alq3 usually, uses compound 1-1 in element manufacturing of the present invention, also uses Alq3 as a comparison simultaneously.
Negative electrode can adopt metal and composition thereof structure, as Mg:Ag, Ca:Ag etc., also can be electron injecting layer/metal-layer structure, as LiF/Al, Li
2Common cathode construction such as O, wherein electron injecting layer can be simple substance, compound or the mixture of basic metal, alkaline-earth metal, transition metal, also can be the composite cathode structure that multilayer material constitutes.Selected cathode material is Mg:Ag/Ag in element manufacturing of the present invention.
The different materials of using among the present invention is as follows:
The preparation and the result of embodiment 11 electroluminescence devices
Preparation OLED-1: sheet glass supersound process in commercial clean-out system that will be coated with the ITO transparency conducting layer, in deionized water, wash, at acetone: ultrasonic oil removing in the alcohol mixed solvent, under clean environment, be baked to and remove moisture content fully, with UV-light and ozone clean, and with low energy positively charged ion bundle bombarded surface.
The above-mentioned anodic glass substrate that has 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 one deck NNPA is as the luminescent layer of device on hole transmission layer, and its evaporation speed is 0.1nm/s, and the evaporation total film thickness is 50nm;
Vacuum evaporation one deck compound 1-1 (or Alq3) is as the electron transfer layer of device on luminescent layer, and its evaporation speed is 0.1nm/s, and the evaporation total film thickness is 50nm;
On electron transfer layer successively vacuum evaporation Mg:Ag alloy layer and Ag layer as the negative electrode of device, wherein the Mg:Ag alloy layer the doping ratio be 10: 1, thickness is 100nm, the evaporation speed of Ag layer is 0.3nm/s, thickness is 50nm.
Device performance sees Table 1 and accompanying drawing 3 and accompanying drawing 4, (device architecture: ITO/NPB/A/Mg:Ag/Ag, the composition of A sees the following form, and x and y represent the chromaticity coordinates of device, EQE% represents external quantum efficiency):
| NNPA/Alq3(2 0nm) | 1000 | 11.76 | 1217.75 | 0.82 | 0.22 | 0.1727 | 0.142 3 | 0.6 9 |
| NNPA/ compound 1-1 (20nm) | 1000 | 8.14 | 1029.82 | 0.97 | 0.37 | 0.1597 | 0.102 5 | 1.0 7 |
| NNPA/ compound 1-1 (30nm) | 1000 | 9.95 | 1124.58 | 0.89 | 0.28 | 0.1658 | 0.126 2 | 0.8 3 |
| Condition | Require brightness cd/m2 | Voltage V | Current density A/m2 | Current efficiency cd/A | Luminous efficiency lm/W | x | y | EQE ％ |
| NNPA/ compound 1-1 (20nm)/Alq3 (10nm) | 1000 | 11.12 | 1300.58 | 0.77 | 0.22 | 0.1695 | 0.132 1 | 0.6 9 |
As can be seen from Table 1, compare with Alq3, when electron transfer layer adopted compound 1-1, brightness reached 1000cd/m
2The time voltage lower, current efficiency, luminous efficiency and external quantum efficiency are all higher, red shift does not take place in chromaticity coordinates.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, but the present invention is not limited to the foregoing description and accompanying drawing, should be appreciated that under the guiding of the present invention's design, those skilled in the art can carry out various modifications and improvement, and claims have been summarized scope of the present invention.
Claims (6)
1. organic materials, its general structure is as follows:
Wherein, Ar is selected from anthrylene; R
1-R
8Be independently selected from hydrogen atom respectively; N is selected from 2 to 4 integer.
2. according to the organic materials of claim 1, it is characterized in that its general structure is as follows:
Wherein, Ar is selected from anthrylene; N is selected from 2 to 4 integer.
3. according to the organic materials of claim 1 or 2, it is characterized in that preferred compound is as follows:
4. the described organic materials of claim 1 is used as electron transfer layer in organic electroluminescence device.
5. organic electroluminescence device wherein comprises pair of electrodes and is arranged on organic light emitting medium between this counter electrode, comprises a kind of described material of claim 1 that is selected from this organic light emitting medium at least.
6. organic electroluminescence device according to claim 5 is characterized in that, comprises a kind of compound that is selected from following structure in this organic light emitting medium at least as electron transport material:
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| JP5353233B2 (en) * | 2007-12-27 | 2013-11-27 | Ｊｎｃ株式会社 | Anthracene derivative compound having pyridylphenyl group and organic electroluminescence device |
| WO2010113743A1 (en) | 2009-03-30 | 2010-10-07 | 東レ株式会社 | Light-emitting element material and light-emitting element |
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| CN101898996A (en) * | 2009-05-31 | 2010-12-01 | 清华大学 | Organic material and application thereof to organic electroluminescent devices |
| KR20120083215A (en) | 2009-06-05 | 2012-07-25 | 베이징 비젼녹스 테크놀로지 컴퍼니 리미티드 | Organic electroluminescent device and testing method thereof |
| CN101597255B (en) * | 2009-07-07 | 2012-10-24 | 清华大学 | Organic material and application thereof in organic electroluminescence device (OELD) |
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| US20160118598A1 (en) * | 2013-04-04 | 2016-04-28 | Jnc Corporation | Electron transport material and organic electroluminescent device using same |
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| KR102431667B1 (en) * | 2017-09-21 | 2022-08-12 | 삼성디스플레이 주식회사 | Heterocyclic compound, organic electroluminescence device and organic electroluminescence display device including the same |
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