CN101898996A - Organic material and application thereof to organic electroluminescent devices - Google Patents
Organic material and application thereof to organic electroluminescent devices Download PDFInfo
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- CN101898996A CN101898996A CN2009100850734A CN200910085073A CN101898996A CN 101898996 A CN101898996 A CN 101898996A CN 2009100850734 A CN2009100850734 A CN 2009100850734A CN 200910085073 A CN200910085073 A CN 200910085073A CN 101898996 A CN101898996 A CN 101898996A
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Abstract
The invention relates to an organic material and application thereof to organic electroluminescent devices. The material has a structural general formula below, wherein Ar is one of sub-condensed aromatics having 6 to 30 carbon atoms or sub-condensed heterocyclic aromatics having 6 to 30 carbon atoms; Py is a pyridyl group at the gamma site; and n is an integer in a range from 2 to 4. The organic material can be used as an electron transmission layer in the organic electroluminescent 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.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 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 shown in the formula shown in (1) or (2):
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; Py is selected from the pyridyl of γ position; N is selected from 2 to 4 integer.
In the above-mentioned general formula, Ar is preferably from naphthylidene, connection naphthylidene, anthrylene, Ya perylene base, inferior pyrenyl, Asia
Basic, inferior dibenzo
Base.
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:
1, when n=2,
2, when n=3,
3, when n=4,
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; Py is selected from the pyridyl of γ position; 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.
Embodiment
It is from 4-(to bromophenyl) pyridine that organic materials of the present invention has all been used in building-up process.
One, the preparation of intermediate 4-(to bromophenyl) pyridine and boric acid thereof
1,4-(4-bromophenyl) pyridine is synthetic
Under nitrogen protection, in a reaction flask, add 2.46g gram 4-pyridine boric acid (molecular weight 123,0.02mol 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 Na0H, uses the ethyl acetate extraction product.Evaporate to dryness obtains oily product 3.13g, productive rate 67.17%, purity 97.70%.
2,4-(3-bromophenyl) pyridine is synthetic
Under nitrogen protection, in a reaction flask, add 2.46g gram 4-pyridine boric acid (molecular weight 123,0.02mol 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%.
3,4-(4-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 4-(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%.
4,3-(4-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
Embodiment 1 compound 1-1's is synthetic
Under the Ar gas shiled; in a 500mL there-necked flask, add 4-(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 ℃, naphthoquinones 0.918g (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 2.49g, purity 97.68%, productive rate 99.02%.
Product MS (m/e): 434; Ultimate analysis (C
32H
22N
2): theoretical value C:88.45%, H:5.10%, N:6.45%; Measured value C:88.44%, H:5.07%, N:6.49%.
Compound 1-2's is synthetic identical therewith, just the 4-in the raw material (4-bromophenyl) pyridine is changed to 4-(3-bromophenyl) pyridine and gets final product, and product is a faint yellow solid.
Embodiment 2 compound 1-9's is synthetic
Under the Ar gas shiled; in a 500mL there-necked flask, add 4-(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 1-10's is synthetic identical therewith, just the 4-in the raw material (4-bromophenyl) pyridine is changed to 4-(3-bromophenyl) pyridine and gets final product, and product is a faint yellow solid.
Embodiment 3 compound 1-13's is synthetic
Reaction process is same as embodiment 2, just the raw material anthraquinone is changed to 1, and 2-benzo anthraquinone obtains the faint 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:89.85%, H:4.93%, N:5.22%.
Embodiment 4 compound 1-19's is synthetic
Reflux condensing tube and nitrogen protection device are installed on a there-necked flask.Under nitrogen protection, add: 1g (2.78mmol) 2,7-dibromo pyrene, 1.37g (6.9mmol) 4-(4-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 three times with water pump, add 45ml water, 30ml ethanol and 48ml toluene.With water pump bleed the ventilation three 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 little yellow solid product 0.99g, productive rate 70.18%.
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 5 compound 1-20's is synthetic
Synthetic method is same as embodiment 4, and just with raw material 2,7-dibromo pyrene is 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%.
Be the Application Example of The compounds of this invention below:
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 a phenylbenzene-9 in element manufacturing of the present invention, 10-dinaphthyl anthracene (PADN).
The electric transmission layer material uses Alq3 usually, uses compound 1-9 and 1-13 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.
Preparation OLED-1:
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.
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 PAND 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 30nm;
Vacuum evaporation one deck compound 1-9 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 20nm or 30nm;
On electron transfer layer successively vacuum evaporation Mg:Ag alloy layer and Ag layer as the negative electrode of device, wherein Mg: the 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, (device architecture: ITO/NPB/PADN/ compound 1-9/Mg:Ag/Ag).
Preparation OLED-2:
According to the method for preparing OLED-1, the material of electron transfer layer is changed to compound 1-13, device performance sees Table 1, device architecture: (ITO/NPB/PADN/ compound 1-13/Mg:Ag/Ag).
Preparation OLED-3 (Comparative Examples):
According to the method for preparing OLED-1, the material of electron transfer layer is changed to compd A lq3, device performance sees Table 1.
Table 1:
As can be seen from Table 1, compare with Alq3, when electron transfer layer adopted compound 1-13, brightness reached 1000cd/m
2The time voltage lower, current efficiency, luminous efficiency are all higher.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 the foregoing description, 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 (8)
1. organic materials, its general structure is selected from following general formula (1) or (2):
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; Py is selected from the pyridyl of γ position; N is selected from 2 to 4 integer.
2. according to the organic materials of claim 1, it is characterized in that Ar is preferably from naphthylidene, connection naphthylidene, anthrylene, Ya perylene base, inferior pyrenyl, Asia
Basic or inferior dibenzo
Base etc.
3. according to the organic materials of claim 1, it is characterized in that:
When n=2, the structure of Ar residue is as follows:
When n=3, the structure of Ar residue is as follows:
When n=4, the structure of Ar residue is as follows:
4. according to the organic materials of claim 1, concrete molecular structure is as follows:
5. the described organic materials of claim 1 is used as electron transfer layer in organic electroluminescence device.
6. organic electroluminescence device wherein comprises pair of electrodes and is arranged on organic light emitting medium between this counter electrode, comprises a kind of following general formula (1) or (2) described material of being selected from 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; Py is selected from the pyridyl of γ position; N is selected from 2 to 4 integer.
7. organic electroluminescence device according to claim 6 is characterized in that, general formula (1) or (2) described material, and when n=2, the structure of Ar residue is as follows:
When n=3, the structure of Ar residue is as follows:
When n=4, the structure of Ar residue is as follows:
8. organic electroluminescence device according to claim 6 is characterized in that, general formula (1) or (2) described material are as electron transport material.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013114941A1 (en) * | 2012-02-03 | 2013-08-08 | Jnc株式会社 | Anthracene derivative and organic electroluminescent element using same |
| JP2015051966A (en) * | 2013-08-07 | 2015-03-19 | Jnc株式会社 | Electron transport material and organic electroluminescent element using the same |
| KR20150062241A (en) * | 2013-11-28 | 2015-06-08 | 엘지디스플레이 주식회사 | Compound and organic light emitting device comprising the same |
| JP2019096823A (en) * | 2017-11-27 | 2019-06-20 | Jnc株式会社 | Organic electroluminescent element |
| CN110010774A (en) * | 2018-01-05 | 2019-07-12 | 固安鼎材科技有限公司 | Organic electroluminescence device |
| WO2020232852A1 (en) * | 2019-05-20 | 2020-11-26 | 武汉华星光电半导体显示技术有限公司 | Organic light-emitting material and preparation method therefor, and organic light-emitting device |
| US11312691B2 (en) | 2017-02-21 | 2022-04-26 | Lg Chem, Ltd. | Heterocyclic compounds and organic light emitting device using the same |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013114941A1 (en) * | 2012-02-03 | 2013-08-08 | Jnc株式会社 | Anthracene derivative and organic electroluminescent element using same |
| JPWO2013114941A1 (en) * | 2012-02-03 | 2015-05-11 | Jnc株式会社 | Anthracene derivative and organic electroluminescence device using the same |
| TWI547481B (en) * | 2012-02-03 | 2016-09-01 | 捷恩智股份有限公司 | Anthracene derivative and organic electroluminescence element using the same, electron transporting material, display device and lighting device |
| US9478750B2 (en) | 2012-02-03 | 2016-10-25 | Jnc Corporation | Anthracene derivative and organic electroluminescent element using the same |
| JP2015051966A (en) * | 2013-08-07 | 2015-03-19 | Jnc株式会社 | Electron transport material and organic electroluminescent element using the same |
| KR20150062241A (en) * | 2013-11-28 | 2015-06-08 | 엘지디스플레이 주식회사 | Compound and organic light emitting device comprising the same |
| KR102228323B1 (en) * | 2013-11-28 | 2021-03-16 | 엘지디스플레이 주식회사 | Compound and organic light emitting device comprising the same |
| US11312691B2 (en) | 2017-02-21 | 2022-04-26 | Lg Chem, Ltd. | Heterocyclic compounds and organic light emitting device using the same |
| JP2019096823A (en) * | 2017-11-27 | 2019-06-20 | Jnc株式会社 | Organic electroluminescent element |
| CN110010774A (en) * | 2018-01-05 | 2019-07-12 | 固安鼎材科技有限公司 | Organic electroluminescence device |
| CN110010774B (en) * | 2018-01-05 | 2023-06-27 | 固安鼎材科技有限公司 | Organic electroluminescent device |
| WO2020232852A1 (en) * | 2019-05-20 | 2020-11-26 | 武汉华星光电半导体显示技术有限公司 | Organic light-emitting material and preparation method therefor, and organic light-emitting device |
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Application publication date: 20101201 |