CN101967079B - Organic material and application thereof in organic electroluminescent devices - Google Patents
Organic material and application thereof in organic electroluminescent devices Download PDFInfo
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- CN101967079B CN101967079B CN 200910151161 CN200910151161A CN101967079B CN 101967079 B CN101967079 B CN 101967079B CN 200910151161 CN200910151161 CN 200910151161 CN 200910151161 A CN200910151161 A CN 200910151161A CN 101967079 B CN101967079 B CN 101967079B
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Abstract
The invention relates to an organic material and application thereof to organic electroluminescent devices. The organic material has a general structural formula, wherein R1 and R2 may be the same or different from each other, and are independently aryl groups or substituted aryl groups; and L is an alkylidene group or a cycloalkylidene group and comprises a straight chain, a branched chain or the alkylidene group with a naphthenic base. The organic material can be used for the organic electroluminescent devices.
Description
Technical field
The present invention relates to a kind of organic compound, this organic compound can be applied to organic electroluminescence device.
Background technology
Organic light emitting display has luminous, wide visual angle, and advantages such as higher brightness, contrast gradient and low energy expenditure as flat panel display of new generation, have obtained increasing concern.
After C.W.TANG in 1987 etc. have found that the oled that drives with low voltage is luminous, along with going deep into of oled research, increasing organic materials is developed, and is used for oled and shows, and along with the development of technology, the multilayered structure of oled has progressively occupied position of mainstream.In the oled of multilayered structure display equipment, main a kind of structure is anode/hole injection layer/hole transmission layer/luminescent layer/electron transfer layer/electron injecting layer/negative electrode.Luminescent layer generally is made up of two portions, and a kind of is material of main part, and another is dopant dye, in main body body material, and problem such as blue light material still exists the life-span short, and efficient is low.
General blue light material of main part is to be the compound of parent with the anthracene now, for example among the US5935721, the application of compound in blue-light device of dinaphthyl anthracene class described, equally, at CN1821341, also describe a kind of improved application of compound in blue oled device that contains anthracene, also described the application of the derivative of improved anthracene in addition among the WO04/013073.But all these materials have a lot of shortcomings, and for example luminous efficiency is not high, and material filming is bad, and glow color colourity is impure, and the carrier transport ability of material is lower etc.
Therefore we can recognize that the improvement of luminous material of main part comprises luminous efficiency for the various performances of improving the oled device, film-forming properties, and current efficiency, having is very much the effect of key.
Summary of the invention
For luminescent material is improved, we have carried out deep research, and higher in the hope of finding an efficient, the blue light material of main part that colourity is purer found that, the compound of following structure, can success as the blue light material of main part:
Wherein R1 and R2 can be identical or different, and independently are the aryl of aryl or replacement separately.L is alkylidene group, comprises straight chain, side chain or has the alkylidene group of cycloalkyl.
In above general formula I, the typical structure of L is as follows:
Among the I, R1 and R2 can be identical or different in above general formula, and its typical structure is as follows:
For above general formula I is described better, list following structure, be not limited only to following structure but the present invention includes:
After organic materials of the present invention is made organic electroluminescence device, have luminous efficiency and power efficiency preferably.
Embodiment:
Below introduce embodiments of the present invention:
The embodiment of compound:
Embodiment 1: compound (10) synthetic
A) 2-methyl-9,10-diphenylanthrancene synthetic
250 milliliters of there-necked flasks; nitrogen protection; to the tetrahydrofuran (THF) that wherein adds 50 milliliters of dryings; 4.71 gram bromobenzene (0.03Mol); be cooled to-78 ℃ with acetone the dry ice bath, stirring and slowly dripping 10Ml concentration down is the hexane solution of the n-Butyl Lithium of 2.5Mol/L, and reaction solution was kept 1 hour down in-78 ℃; to wherein adding 2.22 gram 2-methylanthraquinones (0.01Mol), slowly be warming up to 25 ℃ of reactions 4 hours then.In the aqueous solution of the Glacial acetic acid that impouring is 100 milliliter 5%, separate out yellow solid, suction filtration, washing.The yellow solid that obtains is added 250 milliliters of there-necked flasks, add 60 milliliters of Glacial acetic acid, 9 grams, one hydration inferior sodium phosphate (0.085Mol), 9 gram potassiumiodides (0.054Mol), be heated to back flow reaction 2 hours under stirring, the cooling back adds 100 ml waters, filters the 20Ml water washing, the 20ML washing with alcohol, obtain yellow solid 3.0 grams, high performance liquid chromatography content 98.2%, productive rate 87.2%.Mass spectrum m/e 344.
B) 2-brooethyl-9,10-diphenylanthrancene synthetic
250 milliliters of there-necked flasks are to wherein adding 50 milliliters of tetracol phenixin, 3.0 gram 2-methyl-9,10-diphenylanthrancene (0.0087Mol), 1.7 gram N-bromo-succinimides (0.0096Mol) add a small amount of BPO, stir temperature rising reflux reaction down 8 hours, cooling is filtered, mother liquor is evaporated to dried, the gained yellow solid is separated with silicagel column, and the sherwood oil wash-out gets yellow solid 2.80 grams, high performance liquid chromatography content 99.1%, productive rate 76%.Mass spectrum m/e 422.
C) compound (10) is synthetic
250 milliliters of there-necked flasks; nitrogen protection; the tetrahydrofuran (THF) that adds 50 milliliters of dryings, 0.077 gram MAGNESIUM METAL (0.0032Mol), an iodine; with 2.54 gram 2-brooethyls-9; 20 milliliters of tetrahydrofuran solutions of 10-diphenylanthrancene (0.006Mol) are to wherein dripping about 1 milliliter, and question response causes the back and stirs the remaining 2-brooethyl-9 of dropping down, the tetrahydrofuran solution of 10-diphenylanthrancene; finish and refluxed 30 minutes; be down to 25 ℃ then, to the hydrochloric acid soln that wherein slowly adds 100 milliliter 5%, separatory; the organic layer evaporate to dryness; silicagel column separates, and the sherwood oil wash-out gets yellow solid 1.10 grams; high performance liquid chromatography content 99.5%, productive rate 53%.Mass spectrum m/e 686.
Embodiment 2: compound (13) synthetic
A) 2-methyl-9,10-two (1-naphthyl) anthracene synthetic
With 2-methyl-9, synthesizing of 10-diphenylanthrancene just changes bromobenzene into the 1-bromonaphthalene, product high performance liquid chromatography content 98.9%, productive rate 80.1%.Mass spectrum m/e 444.
2-brooethyl-9,10-two (1-naphthyl) anthracene synthetic
With 2-brooethyl-9, synthesizing of 10-diphenylanthrancene is that the 10-diphenylanthrancene changes 2-methyl-9 into, 10-two (1-naphthyl) anthracene, product high performance liquid chromatography content 99.2%, productive rate 78% with 2-methyl-9.Mass spectrum m/e 522.
C) compound (13) is synthetic
Synthesizing of same compound (10), just with 2-brooethyl-9, the 10-diphenylanthrancene changes 2-brooethyl-9 into, 10-(1-naphthyl) anthracene, product high performance liquid chromatography content 99.6%, productive rate 60%.Mass spectrum m/e 886.
Organic electroluminescence device embodiment:
In following examples, with the material preparation organic electroluminescence device among the present invention, do hole transmission layer with NPB, the material among the present invention is used as the blue light main body, does dyestuff with DPAVBi, does electron transfer layer with AlQ3, negative electrode LiF/Al.
Embodiment 3: utilize compound (13) as material of main part doped, blue dyestuff DPAVBi, the preparation blue electroluminescent devices.Device architecture is ITO/NPB (40nm)/compound (13): DPAVBi (6%) (x nm)/AlQ3 (20nm)/LiF (0.5nm)/Al (150nm).
On the glass substrate that an Indium sesquioxide-stannic oxide that cleaned (ITO) covers, the NPB of method continuous evaporating-plating 40nm by vacuum evaporation, the blue dyes DPAVBi of the compound among the present invention (13) and 6% (mass percent), and then the thick AlQ3 of evaporation 20nm, the Al of the LiF of evaporation 0.5nm and 150nm does negative electrode again.The thickness that changes luminescent layer is 40,30,20nm, has prepared the device of three kinds of structures, and wherein when light emitting layer thickness was 30nm, opening bright voltage was 5V, and maximum luminous efficiency can reach 7.5cd/A, and maximum power efficiency is 3.8lm/W, has photoelectric properties preferably.Specific targets are shown in Table 1.
The performance perameter of table 1:ITO/NPB (40nm)/compound (13): DPAVBi (6%) (x nm)/AlQ3 (20nm)/LiF (0.5nm)/Al (150nm) main devices
Embodiment 4: utilize compound (10) as material of main part doped, blue dyestuff DPAVBi, the preparation blue electroluminescent devices.Device architecture is ITO/NPB (40nm)/compound (10): DPAVBi (6%) (x nm)/AlQ3 (20nm)/LiF (0.5nm)/Al (150nm).
On the glass substrate that an Indium sesquioxide-stannic oxide that cleaned (ITO) covers, the NPB of method continuous evaporating-plating 40nm by vacuum evaporation, the blue dyes DPAVBi of the compound among the present invention (10) and 6% (mass percent), and then the thick AlQ3 of evaporation 20nm, the Al of the LiF of evaporation 0.5nm and 150nm does negative electrode again.The thickness that changes luminescent layer is 40,30,20nm, has prepared the device of three kinds of structures, and wherein when light emitting layer thickness was 30nm, opening bright voltage was 6V, and maximum luminous efficiency can reach 5.5cd/A, and maximum power efficiency is 2.8lm/W, has photoelectric properties preferably.Specific targets are shown in Table 2.
The performance perameter of table 2:ITO/NPB (40nm)/compound (10): DPAVBi (6%) (x nm)/AlQ3 (20nm)/LiF (0.5nm)/Al (150nm) main devices
Claims (2)
1. organic compound, its structure is as shown below:
General formula I
R wherein
1And R
2Identical, be phenyl or naphthyl, L is ethylidene.
2. an organic luminescent device comprises cathode layer, and anode layer, and middle organic luminous layer is characterized in that organic luminous layer wherein comprises the described organic compound of claim 1, and this organic materials is done the blue light material of main part.
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| CN101967079B true CN101967079B (en) | 2013-09-04 |
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Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105601557B (en) * | 2013-12-10 | 2018-06-26 | 京东方科技集团股份有限公司 | Containing anthracene compound, preparation method and its application, organic luminescent device |
| CN104744346B (en) * | 2013-12-27 | 2021-03-02 | 江苏和成新材料有限公司 | Dianthracene compound with pyridyl at tail end and application thereof |
| CN104744347B (en) * | 2013-12-27 | 2021-03-02 | 江苏和成新材料有限公司 | Dianthracene compound with pyridyl at tail end and application thereof |
| KR102090364B1 (en) * | 2017-04-10 | 2020-03-17 | 주식회사 엘지화학 | Anthracene derivatives and organic light emitting device using the same |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5935721A (en) * | 1998-03-20 | 1999-08-10 | Eastman Kodak Company | Organic electroluminescent elements for stable electroluminescent |
| CN1675148A (en) * | 2002-08-02 | 2005-09-28 | 出光兴产株式会社 | Anthracene derivatives and organic electroluminescent devices made therefrom |
| CN1821341A (en) * | 2004-12-07 | 2006-08-23 | Lg.菲利浦Lcd株式会社 | Organic electroluminescent devices |
-
2009
- 2009-07-28 CN CN 200910151161 patent/CN101967079B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5935721A (en) * | 1998-03-20 | 1999-08-10 | Eastman Kodak Company | Organic electroluminescent elements for stable electroluminescent |
| CN1675148A (en) * | 2002-08-02 | 2005-09-28 | 出光兴产株式会社 | Anthracene derivatives and organic electroluminescent devices made therefrom |
| CN1821341A (en) * | 2004-12-07 | 2006-08-23 | Lg.菲利浦Lcd株式会社 | Organic electroluminescent devices |
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