CN101935523A - Novel efficient metallic iridium coordination compound red organic electrophosphorescent material and organic electroluminescent device thereof - Google Patents
Novel efficient metallic iridium coordination compound red organic electrophosphorescent material and organic electroluminescent device thereof Download PDFInfo
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Abstract
The invention discloses a novel efficient metallic iridium coordination compound red organic electrophosphorescent material and an organic electroluminescent device thereof. The organic electroluminescent device is in a lamellar doping type structure, wherein a luminescent layer adopts Zn(BTZ)2 as a phosphorescent main material and a series Ir (III) coordination compound as a doping agent. The metallic iridium coordination compound red organic electrophosphorescent material taking pyridazine united aromatic hydrocarbon as a basic skeleton structure can realize saturated red phosphorescence emission of 610-620 nanometers with colour purity (0.65, 0.35) by combining with the structure optimization of the organic electroluminescent device taking the metallic iridium coordination compound red organic electrophosphorescent material as the doping agent and has maximum current efficiency of 12 cd/A and service life of 20000 hours; and compared with the traditional red light material, the metallic iridium coordination compound red organic electrophosphorescent material has the advantages of higher efficiency, more saturated colour purity and obvious red phosphorescent emission of the service life of the excellent device. The invention has flexible manufacture process and provides excellent materials for full color display and illumination application.
Description
Technical field
The invention belongs to organic electromechanical phosphorescent material and device technology field, be specifically related to red organic electromechanical phosphorescent material of a kind of pyridazine biaryl metal iridium complexes and preparation method thereof and based on the organic electroluminescence device of this title complex.
Background technology
Because organic electroluminescence device has the display characteristic that surmounts LCD, becomes follow-on main flow indicating meter most probably, each large enterprises, research institution drop into the exploitation that a large amount of development resources is absorbed in its material and is shown science and technology one after another both at home and abroad; The target of research is the panchromatic demonstration of development, finally realizes industrialization, and red-green-blue is one of important aspect that realizes panchromatic demonstration, and therefore the three primary colours material of the synthetic excellent property of design is crucial.1999, the Thompson professor of American South University of California and professor Forrest of Princeton University took the lead in that three (2-phenylpyridines) are closed iridium and [are called for short Ir (ppy)
3] be doped to N, [be called for short CBP] in the N-two carbazole biphenyl, successfully prepared green electro phosphorescent device, maximum external quantum efficiency reaches 8% (Appl.Phys.Lett, 1999,11,3709), begins to cause insider's concern.Though fluorescent material has been widely used in luminescent material, but theoretically, phosphor material is owing to can effectively utilize triplet exciton, and internal quantum can bring up to 100% from 25% of fluorescence, and this phosphorescent glow is to have one of breakthrough key development in recent years.
At present, redness, green and blue material have all reached the practicability requirement substantially, but red light material is subject to factors such as its less energy gap and material of main part coupling, and also some is barely satisfactory for the luminous efficiency of red material and purity of color, so red material is the emphasis and the difficult point of research always.The more excellent red phosphorescence material of known performance comprises: two (2-thionaphthene pyridine) acetyl acetone iridium [is called for short (Btp)
2Ir (acac)], its peak luminous wavelength 616nm, chromaticity coordinates (0.68,0.32), maximum external quantum efficiency is 7.0 ± 0.5% (Appl.Phys.Lett, 2001,11,1622).There are three (1-phenyl isoquinolin quinolines) to close iridium in addition and [are called for short (Piq)
3Ir] show the scarlet characteristics of luminescence, and have higher efficient (J.Am.Chem.Soc, 2003,42,12971).
Though the research of red organic electromechanical phosphorescent material is increasing in recent years, the material that has greater efficiency, the pure and mild good life performance of saturated colour concurrently rarely has report.
Summary of the invention
Because the restriction of purity of color and efficient, and the life-span often can not satisfy the commercialization requirement, traditional red light material has bigger limitation when being applied to organic electroluminescence device (OLED).Therefore preparation has the material of more excellent luminescent properties and uses it for the doping type device than traditional red phosphorescence material and has important practical significance.For remedying this deficiency, the object of the invention is to provide red organic electromechanical phosphorescent material of a kind of new and effective metal iridium complex and organic electroluminescence device thereof, uses this title complex to have greater efficiency, the pure and mild good life performance of saturated colour as the relative conventional red luminescent material of organic electroluminescence device of doping agent.
Technical solution of the present invention is: the red organic electromechanical phosphorescent material of a kind of new and effective metal iridium complex, and described title complex comprises the structure of formula 1 expression:
Formula 1:
Wherein, Ar-is respectively: one of 1-naphthyl, 2-naphthyl, 2-thienyl, 2-benzothienyl, 9-phenanthryl.R
1, R
2Independently choose one of hydrogen, methyl, ethyl, propyl group, the tertiary butyl, phenyl respectively.
Described Ar-is one of 1-naphthyl, 2-naphthyl, 2-thienyl, 2-benzothienyl, 9-phenanthryl, R
1Be hydrogen, R
2Be hydrogen.
A kind of organic electroluminescence device of stratiform doping type structure, be followed successively by substrate (1), nesa coating (2), hole injection layer (3), hole transmission layer (4), luminescent layer (5), hole blocking layer (6), electron transfer layer (7), electron injecting layer (8), negative electrode (9) by substrate to negative electrode, luminescent layer (5) is taked substrate material: two (2-hydroxy phenyl) benzothiazole closes zinc and [is called for short Zn (BTZ)
2] and doping agent Ir (III) title complex codeposition form, doping agent Ir (III) title complex is selected pyridazine biaryl metal iridium complexes, its chemical formula as shown in Equation 1,
Formula 1:
Wherein, Ar-is respectively: one of 1-naphthyl, 2-naphthyl, 2-thienyl, 2-benzothienyl, 9-phenanthryl.R
1, R
2Independently choose one of hydrogen, methyl, ethyl, propyl group, the tertiary butyl, phenyl respectively.
The mass ratio of matrix and doping agent is 100: 4～10.
Useful result of the present invention is: the invention provides a kind of is the red organic electromechanical phosphorescent material of metal iridium complex of basic skeleton structure with the pyridazine biaryl, in conjunction with being the optimization of the organic electroluminescence device structure of doping agent with it, can realize 610-620nm, purity of color is the saturated red phosphorescent emissions of (0.65,0.35).Its maximum current efficient 12cd/A, life-span 20000h has high-level efficiency more, the red phosphorescent emission remarkable advantages of saturated colour pure and mild good device lifetime more with respect to the conventional red luminescent material.This manufacture craft is flexible, and using for full-color demonstration and illumination provides excellent material.This manufacture craft is flexible, and using for full-color demonstration and illumination provides excellent material.
Description of drawings
Fig. 1 is an organic electroluminescence device structural representation of the present invention.
Embodiment
The present invention is described further below in conjunction with drawings and Examples, and content of the present invention includes but not limited to following each embodiment.
The present invention includes a kind of red organic electromechanical phosphorescent material of pyridazine biaryl metal iridium complexes that contains.General structure is as follows:
Wherein, Ar-is respectively: one of 1-naphthyl, 2-naphthyl, 2-thienyl, 2-benzothienyl, 9-phenanthryl.R
1, R
2Independently choose one of hydrogen, methyl, ethyl, propyl group, the tertiary butyl, phenyl respectively.
The described pyridazine biaryl of this general structure metal iridium complexes comprises but is not limited only to following several:
Compound 1 compound 2
Compound 3 compounds 4
Compound 5
Organic electroluminescence device of the present invention is a stratiform doping type device architecture, is followed successively by substrate 1, nesa coating 2, hole injection layer 3, hole transmission layer 4, luminescent layer 5, hole blocking layer 6, electron transfer layer 7, electron injecting layer 8, negative electrode 9 by substrate to negative electrode.Hole-injecting material is: 4,4 ', 4 " three (N-phenyl-N-(2-naphthyl)) triphenylamine [being called for short 2T-NATA], thickness is 10～60nm; Hole mobile material is: two (N-phenyl-N-(1-naphthyls))-4,4 '-benzidine [being called for short NPB], thickness is 25～50nm; Luminescent layer is the matrix of codeposition: Zn (BTZ)
2With doping agent series Ir (III) title complex, the weight ratio of matrix and doping agent is 100: 4～10, and thickness is 30～40nm; Hole blocking layer is: 2, and 9-dimethyl-4,7-phenylbenzene-1, the luxuriant and rich with fragrance Lip river of 10-quinoline [being called for short BCP], thickness is 5～25nm; Electron transfer layer selects for use three (oxine) aluminium [to be called for short Alq
3], thickness is 20～40nm; Electron injecting layer adopts LiF, and thickness is 0.5～2nm; Negative electrode adopts metal A l, and thickness is 100～200nm.External circuit 10 is the direct drive power supply, can select 3～20v, and the positive pole of external circuit is connected with the side of nesa coating in abutting connection with substrate, and negative pole is connected with negative electrode.11 red phosphorescent light for the organic electroluminescence device emission.
The preparation method of pyridazine biaryl metal iridium complexes mainly contains two steps: first step is the preparation of pyridazine biaryl hydro carbons part; Second step is the preparation of part and trivalent metal iridium salt and the formed metal iridium complex organic electromechanical phosphorescent material of methyl ethyl diketone or derivatives thereof.Concrete technology and operation explanation in conjunction with the embodiments.
Embodiment
Synthetic example 1: synthetic compound 1
According to following reaction formula synthetic compound 1.
Synthetic intermediate 1a
Levulinic acid (2.32g, 19.97mmol), stir in the system of ethanol 80ml and drip hydrazine hydrate down (1.60g 31.96mmol), dropwises post-heating and is warmed up to backflow, continues reaction 2h.Be cooled to room temperature, ethanol is reclaimed in air distillation.Residue is cooled to room temperature, separates out white needle-like crystals.Filtration drain intermediate 1a (1.91g).
Synthetic intermediate 1b
Stir down to intermediate 1a (6.60g, 58.81mmol), (11.0g 68.82mmol), dropwises the back temperature control at 60 ℃～70 ℃ reaction 3h slowly to drip bromine in the system of Glacial acetic acid 29ml.Being cooled to room temperature places ice-water bath that solid is separated out.Filter, filter cake ethyl acetate drip washing is transferred pH=9 with strong aqua, adds a small amount of methylene dichloride after-filtration and drains, and gets off-white color intermediate 1b (6.30g).
Synthetic intermediate 1c
Intermediate 1b (2.20g, 19.98mmol), (15.01g, 97.90mmol) mixed system stir back flow reaction 2h down to phosphorus oxychloride.After being cooled to room temperature reaction solution is stirred in the following slow impouring frozen water, slowly add Anhydrous potassium carbonate and transfer pH=8～9, the dichloromethane extraction water, merging is washed to neutrality, anhydrous magnesium sulfate drying.Filter, filtrate decompression reclaims solvent, obtains yellow synthetic intermediate 1c (1.25g).
Synthetic intermediate 1d
Intermediate 1c (6.45g, 50.17mmol), the 1-naphthalene boronic acids (8.70g, 50.58mmol), DMF195ml, water 40ml, Tetrabutyl amonium bromide 8.10g, Anhydrous potassium carbonate 13.80g, four (triphenyl is seen) close palladium 0.60g, stirring and refluxing 3h under the nitrogen atmosphere.Reaction solution is cooled to room temperature, and dichloromethane extraction, separatory are washed to neutrality, anhydrous magnesium sulfate drying.Filter, filtrate decompression reclaims solvent and gets yellow intermediate 1d (9.72g).
Synthetic intermediate 1e
Intermediate 1d (14.50g, 65.82mmol), the hydration iridous chloride (10.55g, 29.92mmol), water 52ml, ethylene glycol monomethyl ether 158ml, stirring and refluxing 30h under the nitrogen atmosphere.Be cooled to room temperature, filter, water, ethanol, acetone drip washing successively gets red intermediate 1e (16.20g).
Synthetic compound 1
Intermediate 1e (5g, 3.75mmol), methyl ethyl diketone (7.5g, 74.91mmol), ethylene glycol monomethyl ether 85ml, Anhydrous potassium carbonate 5.17g, stirring and refluxing reaction 12h under the nitrogen atmosphere.Reaction solution is cooled to room temperature, filters water, acetone drip washing successively.With the methylene dichloride is that eluent carries out column chromatography.Decompression and solvent recovery gets red powder shape compound 1 (1.2g).
NMR(400M，CDCl
3)
8.62-8.64(2H)，8.34-8.36(2H)，7.26-7.62(8H)，7.02-7.04(2H)，6.36-6.38(2H)，5.30(1H)，2.73(6H)，1.83(6H).
Embodiment 1
The embodiment of the invention is selected 7% doping content doping, and compound 1 is made doping agent in the synthetic embodiment 1, selects CBP and Zn (BTZ) respectively for use
2As the luminescent layer substrate material, adopt thermal evaporation prepared high-performance electroluminescent device.Substrate 1 is selected glass or transparent plastics for use, nesa coating 2 be 20 Ω/sq ITO (tin indium oxide) film as anode, with behind the substrate cleaning at high-purity O
2Plasma under the atmosphere (plasma bombardment) handled 10 minutes, then in high vacuum (3～2 * 10
-4Pa) under, deposit thickness is the hole injection layer 3 of 45nm on nesa coating 2, selects 2T-NATA for use; Deposition hole transmission layer 4 on hole injection layer 3 is selected NPB for use then, and thickness is 25nm; Depositing light emitting layer 5 on hole transmission layer then, luminescent layer 5 adopts co-deposition methods to evaporate A simultaneously, and wherein A is CBP or Zn (BTZ)
2And the compound 1 in the synthetic embodiment 1, its mass ratio is 100: 7, light emitting layer thickness is 25nm; Deposition hole blocking layer 6 above the luminescent layer, the material of hole blocking layer 6 is BCP, thickness is 10nm; Deposit electron transfer layer 7 afterwards on hole blocking layer, electron transfer layer 7 is selected Alq
3, thickness be 25nm; Deposition LiF is as electron injecting layer 8 on electron transfer layer 7 afterwards, and its thickness is 1nm; Deposition cathode 9 on electron injecting layer 8 is selected metal A l for use at last, and its thickness is 200nm.All films adopt the thermal evaporation process deposits to finish.
The thickness of film adopts the film thickness monitoring instrument to monitor, measure luminosity with luminance meter, the vaporator rate of all organic materialss is 3
/ second, the vaporator rate of LiF is 1
/ second, the vaporator rate of metal A l is 10
/ second.
When using device architecture: ITO/2T-NATA (45nm)/NPB (25nm)/A: title complex 1 (10%, 25nm)/BCP (10nm)/Alq
3(25nm)/ device performance during LiF (1nm)/Al (200nm) is as shown in table 2:
Table 1: the performance graph of different substrates material devices
Embodiment 2
In the embodiment of the invention, making processes is with embodiment 1, and luminescent layer 5 is selected Zn (BTZ)
2Do the compound 1 in luminescent layer matrix and the synthetic embodiment 1, its mass ratio is 100: X, and x=4,6,8,10 wherein, the light emitting layer thickness with different levels of doping is 25nm;
When using device architecture: ITO/2T-NATA (45nm)/NPB (25nm)/Zn (BTZ)
2: title complex 4=100: X, (X=4,6,8,10,25nm)/BCP (10nm)/Alq
3(25nm)/ device performance during LiF (1nm)/Al (200nm) is as shown in table 1:
Table 1: the performance graph of different concns device
Claims (4)
1. red organic electromechanical phosphorescent material of new and effective metal iridium complex is characterized in that: described complex structure as shown in Equation 1:
Formula 1:
Wherein, Ar is one of 1-naphthyl, 2-naphthyl, 2-thienyl, 2-benzothienyl, 9-phenanthryl, R
1, R
2Independently choose one of hydrogen, methyl, ethyl, propyl group, the tertiary butyl, phenyl respectively.
2. the red organic electromechanical phosphorescent material of new and effective metal iridium complex according to claim 1, it is characterized in that: described Ar-is one of 1-naphthyl, 2-naphthyl, 2-thienyl, 2-benzothienyl, 9-phenanthryl, R
1Be hydrogen, R
2Be hydrogen.
3. organic electroluminescence device, it is a stratiform doping type structure, be followed successively by substrate (1), nesa coating (2), hole injection layer (3), hole transmission layer (4), luminescent layer (5), hole blocking layer (6), electron transfer layer (7), electron injecting layer (8), negative electrode (9) by substrate to negative electrode, it is characterized in that: luminescent layer (5) is taked substrate material: two (2-hydroxy phenyl) benzothiazole closes zinc and [is called for short Zn (BTZ)
2] and doping agent Ir (III) title complex codeposition form, doping agent Ir (III) title complex selects to contain substituted aryl united quinazoline metal iridium complexes organic electromechanical phosphorescent material, its chemical formula as shown in Equation 1,
Formula 1:
Wherein, Ar-is: one of 1-naphthyl, 2-naphthyl, 2-thienyl, 2-benzothienyl, 9-phenanthryl, R
1, R
2Independently choose one of hydrogen, methyl, ethyl, propyl group, the tertiary butyl, phenyl respectively.
4. organic electroluminescence device as claimed in claim 3 is characterized in that: the mass ratio of matrix and doping agent is 100: 4～10.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013174075A1 (en) * | 2012-05-25 | 2013-11-28 | 南京邮电大学 | Iridium complex containing functional group for hole transporting and electroluminescent device thereof |
| CN103965883A (en) * | 2013-01-30 | 2014-08-06 | 海洋王照明科技股份有限公司 | Blue light-emitting organic electroluminescent material, its preparation method and organic electroluminescent device |
| CN103965868A (en) * | 2013-01-30 | 2014-08-06 | 海洋王照明科技股份有限公司 | Red organic electroluminescent material and its preparation method and application |
| CN104119398A (en) * | 2013-04-28 | 2014-10-29 | 海洋王照明科技股份有限公司 | Blue organic electrophosphorescent material iridium metal complex, preparation method thereof and organic electroluminescent device |
| CN104119394A (en) * | 2013-04-28 | 2014-10-29 | 海洋王照明科技股份有限公司 | Blue organic electrophosphorescent material iridium metal complex, preparation method thereof and organic electroluminescent device |
| US20190194237A1 (en) * | 2017-12-22 | 2019-06-27 | Samsung Electronics Co., Ltd. | Organometallic compound, organic light-emitting device including the organometallic compound, and diagnostic composition including the organometallic compound |
| TWI760235B (en) * | 2021-05-25 | 2022-04-01 | 晶宜科技股份有限公司 | Organic electroluminescent devices and material thereof |
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| US20060024522A1 (en) * | 2004-05-18 | 2006-02-02 | Thompson Mark E | Luminescent compounds with carbene ligands |
| CN101200635A (en) * | 2007-11-27 | 2008-06-18 | 中山大学 | Phosphorescent iridium complex and organic electroluminescent device thereof |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013174075A1 (en) * | 2012-05-25 | 2013-11-28 | 南京邮电大学 | Iridium complex containing functional group for hole transporting and electroluminescent device thereof |
| CN103965883A (en) * | 2013-01-30 | 2014-08-06 | 海洋王照明科技股份有限公司 | Blue light-emitting organic electroluminescent material, its preparation method and organic electroluminescent device |
| CN103965868A (en) * | 2013-01-30 | 2014-08-06 | 海洋王照明科技股份有限公司 | Red organic electroluminescent material and its preparation method and application |
| CN104119398A (en) * | 2013-04-28 | 2014-10-29 | 海洋王照明科技股份有限公司 | Blue organic electrophosphorescent material iridium metal complex, preparation method thereof and organic electroluminescent device |
| CN104119394A (en) * | 2013-04-28 | 2014-10-29 | 海洋王照明科技股份有限公司 | Blue organic electrophosphorescent material iridium metal complex, preparation method thereof and organic electroluminescent device |
| US20190194237A1 (en) * | 2017-12-22 | 2019-06-27 | Samsung Electronics Co., Ltd. | Organometallic compound, organic light-emitting device including the organometallic compound, and diagnostic composition including the organometallic compound |
| TWI760235B (en) * | 2021-05-25 | 2022-04-01 | 晶宜科技股份有限公司 | Organic electroluminescent devices and material thereof |
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