CN101899296A - Red organic electroluminescent phosphorescent material containing aryl united quinazoline metal iridium complexes and organic electroluminescent device thereof - Google Patents
Red organic electroluminescent phosphorescent material containing aryl united quinazoline metal iridium complexes and organic electroluminescent device thereof Download PDFInfo
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- CN101899296A CN101899296A CN 201010225629 CN201010225629A CN101899296A CN 101899296 A CN101899296 A CN 101899296A CN 201010225629 CN201010225629 CN 201010225629 CN 201010225629 A CN201010225629 A CN 201010225629A CN 101899296 A CN101899296 A CN 101899296A
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Abstract
The invention discloses a red organic electroluminescent phosphorescent material containing aryl united quinazoline metal iridium complexes and an organic electroluminescent device thereof. The organic electroluminescent device is in a layered doped structure, wherein Zn(BTZ)2 is selected as a substrate material of a luminescent layer, and serial complexes Ir(III) are selected as dopants. The invention provides a basic skeleton structure, i.e. a red organic electroluminescent phosphorescent material containing the aryl united quinazoline metal iridium complexes, modifies the structure with various different groups, is combined with the structural optimization of the organic electroluminescent device using the groups as dopants and realizes red phosphorescence emission with better purity and higher efficiency as comparison with a traditional red light material. The invention has simple manufacture process and provides excellent material for full color display and illumination application.
Description
Technical field
The invention belongs to organic electromechanical phosphorescent material and device technology field, relate to more specifically and a kind ofly contain the red organic electromechanical phosphorescent material of aryl united quinazoline metal iridium complexes and based on the organic electroluminescence device of this title complex.
Background technology
In order to realize the full-color demonstration of OLED, must design synthesize the three primary colours material of excellent property.Organic electromechanical phosphorescent material is owing to can effectively utilize triplet exciton, and luminous efficiency promotes greatly with respect to fluorescent material.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, in the N-two carbazole biphenyl [be called for short CBP], successfully prepared green electro phosphorescent device, maximum external quantum efficiency reach 8% (Appl.Phys.Lett, 1999,11,3709 ", cause insider's very big concern.
At present, electroluminescent organic material development is the most sophisticated to be the green glow phosphor material, and ruddiness, blue light phosphor material is because limited its less energy gap and material of main part factor such as do not match respectively, and growth momentum lags far behind green light material.The more excellent red phosphorescence material of known performance comprises:
(Btp)
2Ir (acac) and (piq)
2Ir (acac).
Though the research of red organic electromechanical phosphorescent material has in recent years caused people's very big interest, the material that has good efficient and purity of color concurrently rarely has report.This makes design have actual demand than the material that traditional red phosphorescence material has more excellent luminescent properties.
Summary of the invention
Because can not satisfy the requirement of purity of color and efficient simultaneously, traditional red light material has bigger limitation when being applied to organic electroluminescence device (OLED).For remedying this deficiency, the invention provides a kind of novel red organic electromechanical phosphorescent material of aryl united quinazoline metal iridium complexes and organic electroluminescence device of containing.Use this title complex to have higher efficient and purity of color preferably concurrently as the organic electroluminescence device of doping agent.
Technical solution of the present invention is: a kind of novel red organic electromechanical phosphorescent material of aryl united quinazoline metal iridium complexes that contains, and described title complex comprises the structure of formula 1 expression:
Formula 1:
Wherein, Ar-is respectively: one of phenyl, 4-tolyl, 4-trimethylphenylmethane base, 1-naphthyl, 1-(4-methyl) 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 phenyl, 4-tolyl, 4-trimethylphenylmethane base, 1-naphthyl, 1-(4-methyl) 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 aryl united quinazoline metal iridium complexes, its chemical formula as shown in Equation 1,
Formula 1:
Wherein, Ar-is respectively: one of phenyl, 4-tolyl, 4-trimethylphenylmethane base, 1-naphthyl, 1-(4-methyl) 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: 8～12.
Useful result of the present invention is: the invention provides a kind of basic skeleton structure for containing the red organic electromechanical phosphorescent material of aryl united quinazoline metal iridium complexes and this structure being modified with various group, in conjunction with being the optimization of the organic electroluminescence device structure of doping agent with it, realize having better purity of color and the emission of more high efficiency red phosphorescent with respect to the conventional red luminescent material.This manufacture craft is simple, 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 aryl united quinazoline metal iridium complexes that contains.General structure is as follows:
Wherein, Ar-is respectively: one of phenyl, 4-tolyl, 4-trimethylphenylmethane base, 1-naphthyl, 1-(4-methyl) naphthyl, 2-thienyl, 2-benzothienyl, 9-phenanthryl.R
1, R
2Independently choose one of hydrogen, methyl, ethyl, interior base, the tertiary butyl, phenyl respectively.
The described aryl united quinazoline metal iridium complexes of this general structure comprises but is not limited only to following several:
Compound 1 compound 2
Compound 3 compounds 4
Compound 5 compounds 6
Compound 7 compounds 8
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)
2) and doping agent series Ir (III) title complex, the weight ratio of matrix and doping agent is 100: 8～12, 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 nesa coating, and negative pole is connected with negative electrode.11 red phosphorescent light for the organic electroluminescence device emission.
The preparation method who contains aryl united quinazoline metal iridium complexes mainly contains two steps: first step is the preparation of aryl united quinazoline class 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
2-chloro-quinazoline (13.75g, 83.54mmol), phenylo boric acid (11.20g, 91.85mmol), four (triphenyl is seen) close palladium 0.6g, salt of wormwood 23g, Tetrabutyl amonium bromide 13.5g, toluene 150ml, ethanol 100ml, water 50ml, stirring and refluxing 6h under the nitrogen atmosphere.Be cooled to room temperature, separatory, organic phase are washed to neutrality, and anhydrous magnesium sulfate drying filters, and concentrating under reduced pressure gets yellowish brown compound 1a (16g).
Synthetic intermediate 1b
Compound 1a (39g, 189.10mmol), the hydration iridous chloride (26.7g, 75.72mmol), water 133ml, ethylene glycol monomethyl ether 400ml, stirring and refluxing reaction 30h under the nitrogen atmosphere.Reaction solution is cooled to room temperature, filter, water, ethanol and acetone drip washing successively, drain the back dry naturally red-brown compound 1b (42.5g).
Synthetic compound 1
Compound 1b (10g, 7.84mmol), methyl ethyl diketone (3.12g, 31.16mmol), TBAH 50ml, methylene dichloride 300ml, stirring and refluxing 2h under the nitrogen atmosphere.Be cooled to room temperature, separatory, organic phase is washed to neutrality, and dried over mgso is filtered concentrating under reduced pressure.The residue column chromatography purification gets red compound 1 (5.5g).
NMR(400M，CDCl
3)
9.36(2H)，8.12-8.16(4H)，7.94-7.98(2H)，7.88-7.90(2H)，7.63-7.64(2H)，6.91-6.93(2H)，6.77-6.89(2H)，6.30-6.32(2H)，5.25(1H)，1.83(6H)，
Synthetic embodiment 2: synthetic compound 2
Adopt the method synthetic compound 2 of synthetic embodiment 1, difference is to use among the synthetic intermediate 1a 4-methylphenylboronic acid to replace phenylo boric acid.
NMR(400M，CDCl
3)
9.33(2H)，7.86-8.14(8H)，7.61-7.62(2H)，6.73-6.75(2H)，6.12(2H)，5.23(1H)，1.81-2.01(6H)，1.55(6H).
Synthetic embodiment 3: synthetic compound 3
Adopt the method synthetic compound 3 of synthetic embodiment 1, difference is to use among the synthetic intermediate 1a 4-tert.-butylbenzene boric acid to replace phenylo boric acid.
NMR(400M，CDCl
3)
9.35(2H)，7.87-8.12(8H)，7.57-7.61(2H)，6.92-6.94(2H)，6.23(2H)，5.23(1H)，1.56(6H)，0.93(18H).
Synthetic embodiment 4: synthetic compound 4
Adopt the method synthetic compound 4 of synthetic embodiment 1, difference is to use among the synthetic intermediate 1a 1-naphthalene boronic acids to replace phenylo boric acid.
NMR(400M，CDCl
3)
9.41(2H)，7.91-8.33(6H)，7.59-7.67(8H)，7.10-7.33(4H)，6.57-6.59(2H)?，5.27(1H)，1.82(6H).
Embodiment 1
The embodiment of the invention is selected Zn (BTZ)
2Do luminescent layer matrix, compound 4 is made doping agent in the synthetic embodiment 4, adopts the thermal evaporation prepared, preparation 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 Zn (BTZ) simultaneously
2With the compound 4 in the synthetic embodiment 4, its mass ratio is 100: X, and x=8 wherein, 9,10, the light emitting layer thickness with different levels of doping 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 is 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 organic materials 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)/Zn (BTZ)
2: title complex 4=100: X, (X=8,9,10,25nm)/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
Embodiment 2
The present invention selects 10% 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 electro phosphorescent 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; Deposit hole transmission layer 4 then on hole injection layer 3, 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: 10, light emitting layer thickness is 25nm; Deposition hole blocking layer 6 above the luminescent layer, thickness is 10nm; Afterwards on hole blocking layer the deposition electron transfer layer 7, thickness be 25nm; Deposit electron injecting layer 8 afterwards on electron transfer layer 7, its thickness is 1nm; Deposition cathode 9 on electron injecting layer 8 at last, 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 organic materials 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 (10hm)/Alq
3(25nm)/ device performance during LiF (1nm)/Al (200nm) is as shown in table 2:
Table 2: the performance graph of different substrates material devices
Claims (4)
1. contain the red organic electromechanical phosphorescent material of aryl united quinazoline metal iridium complexes, it is characterized in that: described material structure as shown in Equation 1:
Formula 1:
Wherein, Ar-is one of phenyl, 4-tolyl, 4-trimethylphenylmethane base, 1-naphthyl, 1-(4-methyl) 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 aryl united quinazoline metal iridium complexes that contains according to claim 1, it is characterized in that: Ar-is one of phenyl, 4-tolyl, 4-trimethylphenylmethane base, 1-naphthyl, 1-(4-methyl) bitter edible plant base, 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 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 phenyl, 4-tolyl, 4-trimethylphenylmethane base, 1-naphthyl, 1-(4-methyl) 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: 8～12.
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Application publication date: 20101201 |