CN104017179A - Bipolar blue-phosphorescence material, preparation method thereof and organic electroluminescent device - Google Patents
Bipolar blue-phosphorescence material, preparation method thereof and organic electroluminescent device Download PDFInfo
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- CN104017179A CN104017179A CN201310066161.6A CN201310066161A CN104017179A CN 104017179 A CN104017179 A CN 104017179A CN 201310066161 A CN201310066161 A CN 201310066161A CN 104017179 A CN104017179 A CN 104017179A
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Abstract
The invention belongs to organic electroluminescent materials and discloses a bipolar blue-phosphorescence material, a preparation method thereof and an organic electroluminescent device. The material has a following structural formula shown in descriptions, wherein R is C1-C20 alkyl, and n is an integer between 10 and 100. According to the bipolar blue-phosphorescence material disclosed by the invention, triazole is an electron transport unit and is beneficial to charge transport; phenothiazine is an important electroluminescent material and has relatively good hole transport property, and N can be subjected to alkyl modification, so that the solubility and film-forming property of phenothiazine are improved; triazole is introduced to a principal chain of a phenothiazinyl polymer, and then, the charge carrier balance of the electroluminescent device is realized, so that the problem of low efficiency of the organic electroluminescent device is solved.
Description
Technical field
The present invention relates to, relate in particular to a kind of bipolarity blue emitting phosphor material and preparation method thereof.The invention still further relates to a kind of bipolarity blue emitting phosphor material that adopts as the organic electroluminescence device of luminescent layer material of main part.
Background technology
From people's reported first such as the C.W.Tang of Kodak in 1987, by evaporation coating method, prepare with Alq
3since bi-layer devices structure for luminescent material, organic electroluminescent has just obtained people's very big concern.Organic electroluminescent can be divided into fluorescence and phosphorescence electroluminescent.According to spin quantum statistical theory, the formation probability ratio of singlet state exciton and triplet exciton is 1:3, singlet state exciton only account for " electron-hole pair " 25%.Therefore, the fluorescence that comes from the radiative transition of singlet state exciton just only accounts for 25% of total input energy, and the electroluminescent of phosphor material just can utilize the energy of whole excitons, thereby has larger superiority.In present electrophosphorescence device, mostly adopt Subjective and Objective structure, soon phosphorescent emissions material, with certain doped in concentrations profiled in main substance, to avoid burying in oblivion of triplet state-triplet state, improves phosphorescent emissions efficiency.At present, the material of main part in electroluminescent device mainly contains small molecules material of main part and polymer body material two classes.
Utilize small molecules material of main part doping phosphorescent complexes to prepare many efficient electroluminescent devices as luminescent layer.Yet prepare small molecules electroluminescent device, need to adopt the complicated technologies such as vacuum evaporation, greatly improve preparation cost.Meanwhile, small molecules itself is easy to the character such as crystallization and has also greatly limited the stability of device.In recent years, utilize the material doped various phosphorescent complexes objects of polymer body to prepare electroluminescent device as luminescent layer and received more concern.Recently, about thering is the polymer body material of bipolarity carrier transport, also there is report.(the J.Phys.Chem.B.2005 such as Wu, 109,14000.) reported a series of take gather fluorenes as main chain, the polymer body material that side chain contains carbazole and oxadiazole group, a kind of title complex of osmium of take is guest materials, the maximum external quantum efficiency 8.37% of electroluminescent device of preparation, high-high brightness 16720cd/m
2.Yet, the synthetic relatively complexity of the polymer body material with bipolarity transmission performance of having reported at present, preparation condition is harsher.
Summary of the invention
The bipolarity blue emitting phosphor material that provides a kind of luminous efficiency high is provided the object of the invention.
Technical scheme of the present invention is as follows:
A bipolarity blue emitting phosphor material, its structure is suc as formula as follows:
in formula, R is C
1～C
20alkyl, the integer that n is 10-100.
The present invention also provides the preparation method of bipolarity blue emitting phosphor material described above, comprises the steps:
The compd A and the B that provide respectively following structural formula to represent,
Under oxygen-free environment, after the compd A that is 1:1 ~ 1.2 by mol ratio and B add in organic solvent and to dissolve, add again subsequently catalyzer and alkaline solution, at 70～130 ℃, carry out Suzuki coupling reaction 12～96 hours, stopped reaction cool to room temperature, separating-purifying reaction solution, obtains the described bipolarity blue emitting phosphor material that following structural formula represents:
In above-mentioned formula, R is C
1～C
20alkyl, the integer that n is 10-100.
In a preferred embodiment, oxygen-free environment is mainly at least one gas composition in nitrogen and argon gas.
In a preferred embodiment, to be selected from solvent be at least one in toluene, DMF, tetrahydrofuran (THF) to organic solvent.
In a preferred embodiment, described catalyzer is three or two argon benzyl acetone two palladiums and the 2-dicyclohexyl phosphine-2 ' that triphenylphosphine palladium chloride, tetra-triphenylphosphine palladium, the mol ratio palladium that is 1:4 ~ 8 and tri-o-tolyl phosphine mixture or mol ratio are 1:4 ~ 8,6 '-dimethoxy-biphenyl mixture; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
Described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate and sodium hydrogen carbonate solution; The volumetric molar concentration of described alkaline solution is 2mol/L; In described alkaline solution, the mol ratio of alkali and compd A is 20:1.
In a preferred embodiment, the temperature of reaction of Suzuki reaction is 90～120 ℃, and the reaction times is 24～72 hours.
In a preferred embodiment, described Suzuki coupling reaction stops and cool to room temperature, and separating-purifying reaction solution process comprises the steps:
After Suzuki coupling reaction stops, in reaction solution, add methyl alcohol precipitating, and use successively methyl alcohol and normal hexane extracting after filtering by apparatus,Soxhlet's, then take chloroform as solvent extraction is to colourless, collect chloroformic solution and be spin-dried for and obtain solid, by described solid 50 ℃ of dry 24h under vacuum, obtain described bipolarity blue emitting phosphor material.
Another object of the present invention is to provide a kind of organic electroluminescence device, comprise the anode conducting substrate, hole injection layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer and the cathode layer that stack gradually, wherein, the material of described luminescent layer is two (4,6-difluorophenyl pyridine-N, C2) pyridine formyl closes iridium (FIrpic) and according to 10% mass percent, is doped to the doping mixing material obtaining in the bipolarity blue emitting phosphor material (representing with P) that following structural formula represents:
In above-mentioned formula, R is C
1～C
20alkyl, the integer that n is 10-100.
In organic electroluminescence device, anode conducting substrate adopts indium tin oxide (ITO) glass, is called for short ITO; Anode layer is ITO, and substrate is glass;
The material of hole injection layer adopts PEDOT:PSS, and wherein, colon ": " represents to mix; PEDOT is poly-(3,4-Ethylenedioxy Thiophene), and PSS is poly-(styrene sulfonic acid).
The material of hole blocking layer is 2,9-dimethyl-4,7-phenylbenzene-1,10-phenanthroline (BCP);
The material of electron transfer layer is oxine aluminium (Alq
3);
The material of electron injecting layer is LiF;
The material of cathode layer is Al;
Therefore, described organic electroluminescence device can be by following representation, and wherein, brace "/" represents laminate structure:
ITO/PEDOT:PSS/P:FIrpic/BCP/Alq
3/LiF/Al。
Bipolarity blue emitting phosphor material provided by the invention, its triazole is an electric transmission unit, is conducive to electric charge transmission; Thiodiphenylamine is the important electroluminescent material of a class, and it has good hole transport performance, and N is upper can carry out alkyl modified, thereby improves solubility property and the film forming properties of copolymerization carbazole.On carbazolyl polymers main chain, introduce triazole, realize the carrier balance of electroluminescent device, thereby solve organic electroluminescence device low efficiency problem.
Bipolarity blue emitting phosphor material preparation method provided by the invention, has adopted better simply synthetic route, thereby reduces technical process, and starting material are cheap and easy to get, and manufacturing cost is reduced.
Accompanying drawing explanation
Fig. 1 is the thermogravimetic analysis (TGA) figure of the bipolarity blue emitting phosphor material that makes of embodiment 1;
Fig. 2 is the structural representation of the organic electroluminescence device that makes of embodiment 6.
Embodiment
In order to understand better the content of patent of the present invention, below by concrete example and legend, further illustrate technology case of the present invention, specifically comprise material preparation and device preparation, but these embodiments do not limit the present invention, wherein, the monomer of compd A is bought and is obtained from the market, the monomer reference literature (Synth.Met.2007 of compd B, 157,743.) disclosed method is synthetic obtains.
Embodiment 1:
The bipolarity blue emitting phosphor material of the present embodiment, poly-{ N-normal hexane base-3,7-bis-bases-thiodiphenylamine-co-3,5-bis-(3-base-phenyl)-4-phenyl-4H-1,2,4-triazole } (P1) (wherein, R is normal hexane base, and n=42), its structural formula is as follows:
The preparation process of above-mentioned polymkeric substance is as follows:
Reaction formula is as follows:
Under argon shield, by N-normal hexane base-3,7-bis-tetramethyl ethylene ketone boric acid ester thiodiphenylamine (107mg, 0.2mmol), 3,5-bis-(3-bromophenyl)-4-phenyl-4H-1,2,4-triazole (91mg, 0.2mmol) add in the flask that fills 10ml toluene solvant, after fully dissolving, salt of wormwood (2mL, 2mol/L) solution is joined in flask, vacuumize deoxygenation and be filled with argon gas, then add bi triphenyl phosphine dichloride palladium (5.6mg, 0.008mmol); Flask is heated to 100 ℃ and carries out Suzuki coupling reaction 48h.Subsequently, after cooling, stop polyreaction, to dripping in flask, in 50ml methyl alcohol, carry out sedimentation; After filtering by apparatus,Soxhlet's, use successively methyl alcohol and normal hexane extracting 24h.Then the chloroform of take is extremely colourless as solvent extraction, collects chloroformic solution and be spin-dried for to obtain red powder, and under vacuum pump, taking out spends the night obtains P1 product, productive rate 79%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=32.7kDa, M
w/ M
n=2.3.
Fig. 1 is the thermogravimetic analysis (TGA) figure of the bipolarity blue emitting phosphor material that makes of embodiment 1.Thermogravimetic analysis (TGA) is completed by Perkin-Elmer Series 7 Thermo System measurements, and all measurements all complete in atmosphere at room temperature.As shown in Figure 1, the thermal weight loss temperature (T of this material 5%
d) be 421 ℃.
Embodiment 2:
The bipolarity blue emitting phosphor material of the present embodiment, poly-{ N-methyl-3,7-bis-bases-thiodiphenylamine-co-3,5-bis-(3-base-phenyl)-4-phenyl-4H-1,2,4-triazole } (P2) (wherein, R is methyl, and n=89), its structural formula is as follows:
The preparation process of above-mentioned polymkeric substance is as follows:
Reaction formula is as follows:
Under nitrogen and the protection of argon gas gas mixture; N-methyl-3 just; 7-bis-tetramethyl ethylene ketone boric acid ester thiodiphenylamine (140mg; 0.3mmol), 3; 5-bis-(3-bromophenyl)-4-phenyl-4H-1; 2; 4-triazole (137mg; 0.3mmol) add in the two-mouth bottle of 50mL specification with 15mL tetrahydrofuran (THF); after fully dissolving, pass into after the about 20min of gas mixture air-discharging of nitrogen and argon gas, then tetra-triphenylphosphine palladium (4mg, 0.003mmol) is added wherein; after fully dissolving, add again sodium bicarbonate (3mL, 2mol/L) solution.After the about 10min of gas mixture air-discharging of fully logical nitrogen and argon gas, two-mouth bottle is joined to 70 ℃ and carry out Suzuki coupling reaction 96h again.Subsequently, after cooling, stop polyreaction, in two-mouth bottle, add 40mL methyl alcohol precipitating, after filtering by apparatus,Soxhlet's, use successively methyl alcohol and normal hexane extracting 24h.Then the chloroform of take is extremely colourless as solvent extraction, collects chloroformic solution and be spin-dried for to obtain red solid, after collection, under vacuum, after 50 ℃ of dry 24h, obtains P2 product.Productive rate is 84%.Test result is: Molecular weight (GPC, THF, R.I): M
n=50.6kDa, M
w/ M
n=2.0.
Embodiment 3:
The bipolarity blue emitting phosphor material of the present embodiment, i.e. poly-{ N-NSC 62789 base-3,7-bis-bases-thiodiphenylamine-co-3,5-bis-(3-base-phenyl)-4-phenyl-4H-1,2,4-triazole } (P3) (wherein, R is NSC 62789 base, and n=100), its structural formula is as follows:
The preparation process of above-mentioned polymkeric substance is as follows:
Reaction formula is as follows:
Under nitrogen protection, by N-NSC 62789 base-3,7-bis-tetramethyl ethylene ketone boric acid ester thiodiphenylamine (220mg, 0.3mmol), 3,5-bis-(3-bromophenyl)-4-phenyl-4H-1,2,4-triazole (150mg, 0.33mmol), palladium (3.5mg, 0.015mmol) and three (o-methoxyphenyl) phosphine (21mg, 0.06mmol) joins the N that fills 12mL, in the flask of dinethylformamide, after fully dissolving, add salt of wormwood (3mL, 2mol/L) solution, in flask, lead to after the about 30min of nitrogen purge gas subsequently; Flask is heated to 130 ℃ and carries out Suzuki coupling reaction 12h.Subsequently, after cooling, stop polyreaction, in flask, add 40mL methyl alcohol precipitating, after filtering by apparatus,Soxhlet's, use successively methyl alcohol and normal hexane extracting 24h; Then the chloroform of take is extremely colourless as solvent extraction, collects chloroformic solution and be spin-dried for to obtain red powder, after collection, under vacuum, after 50 ℃ of dry 24h, is P3 product, productive rate 82%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=58.9kDa, M
w/ M
n=2.1.
Embodiment 4:
The bipolarity blue emitting phosphor material of the present embodiment, poly-{ N-normal butane base-3,7-bis-bases-thiodiphenylamine-co-3,5-bis-(3-base-phenyl)-4-phenyl-4H-1,2,4-triazole } (P4) (wherein, R is normal butane base, and n=10), its structural formula is as follows:
The preparation process of above-mentioned polymkeric substance is as follows:
Reaction formula is as follows:
Under nitrogen protection; by N-normal butane base-3; 7-bis-tetramethyl ethylene ketone boric acid ester thiodiphenylamine (152mg; 0.3mmol), 3; 5-bis-(3-bromophenyl)-4-phenyl-4H-1; 2; 4-triazole (164mg; 0.36mmol), three or two argon benzyl acetone two palladiums (9mg, 0.009mmol) and 2-dicyclohexyl phosphines-2 ', 6 '-dimethoxy-biphenyl (29mg; 0.072mmol) join the N that fills 12mL; in the flask of dinethylformamide, after fully dissolving, add sodium bicarbonate (3mL, 2mol/L) solution.In flask, lead to after the about 30min of nitrogen purge gas subsequently; Flask is heated to 120 ℃ and carries out Suzuki coupling reaction 36h.Subsequently, after cooling, stop polyreaction, in flask, add 40mL methyl alcohol precipitating, after filtering by apparatus,Soxhlet's, use successively methyl alcohol and normal hexane extracting 24h; Then the chloroform of take is extremely colourless as solvent extraction, collects chloroformic solution and be spin-dried for to obtain red powder, after collection, under vacuum, after 50 ℃ of dry 24h, is P4 product, and productive rate is 75%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=14.4kDa, M
w/ M
n=2.4.
Embodiment 5:
The bipolarity blue emitting phosphor material of the present embodiment, i.e. poly-{ N-dodecyl-3,7-bis-bases-thiodiphenylamine-co-3,5-bis-(3-base-phenyl)-4-phenyl-4H-1,2,4-triazole } (P5) (wherein, R is dodecyl, and n=35), its structural formula is as follows:
The preparation process of above-mentioned polymkeric substance is as follows:
Reaction formula is as follows:
Under nitrogen and the protection of argon gas gas mixture; by N-dodecyl-3; 7-bis-tetramethyl ethylene ketone boric acid ester thiodiphenylamine (186mg; 0.3mmol), 3; 5-bis-(3-bromophenyl)-4-phenyl-4H-1; 2; 4-triazole (164mg; 0.36mmol) add in the two-mouth bottle of 50mL specification with 15mL toluene; after fully dissolving, pass into after the about 20min of gas mixture air-discharging of nitrogen and argon gas, then tetra-triphenylphosphine palladium (8mg, 0.006mmol) is added wherein; add again salt of wormwood (3mL, 2mol/L) solution.After the about 10min of gas mixture air-discharging of fully logical nitrogen and argon gas, two-mouth bottle is joined to 90 ℃ and carry out Suzuki coupling reaction 60h again.Subsequently, after cooling, stop polyreaction, in two-mouth bottle, add 40mL methyl alcohol precipitating, after filtering by apparatus,Soxhlet's, use successively methyl alcohol and normal hexane extracting 24h.Then the chloroform of take is extremely colourless as solvent extraction, collects chloroformic solution and be spin-dried for to obtain red solid, after collection, under vacuum, after 50 ℃ of dry 24h, obtains P5 product.Productive rate is 71%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=36.0kDa, M
w/ M
n=2.2.
Embodiment 6:
The present embodiment is organic electroluminescence device, the bipolarity blue emitting phosphor material that the material of main part of its luminescent layer adopts embodiment 1 to make, i.e. poly-{ N-normal hexane base-3,7-bis-bases-thiodiphenylamine-co-3,5-bis-(3-base-phenyl)-4-phenyl-4H-1,2,4-triazole } (with P1, representing).
This organic electroluminescence device, its structure as shown in Figure 2, comprises the anode conducting substrate 1, hole injection layer 2, luminescent layer 3, hole blocking layer 4, electric transmission 5, electron injecting layer 6 and the cathode layer 7 that stack gradually.
In this organic electroluminescence device, anode conducting substrate 1 adopts indium tin oxide (ITO) glass, and anode layer is ITO, is called for short ITO; Substrate is glass; The thickness of anode conducting substrate 1 is 150nm;
The material of hole injection layer 2 adopts PEDOT:PSS, and wherein, colon ": " represents to mix, and the thickness of hole injection layer 2 is 30nm;
The material of luminescent layer 3 is two (4,6-difluorophenyl pyridine-N, C2) pyridine formyl closes iridium (III) and (FIrpic) according to 10% mass ratio, is doped to poly-{ N-normal hexane base-3,7-bis-bases-thiodiphenylamine-co-3,5-bis-(3-base-phenyl)-4-phenyl-4H-1,2,4-triazole } (representing with P1) mixing material of forming, be expressed as P1:FIrpic; The thickness of luminescent layer 3 is 20nm;
The material of hole blocking layer 4 is 2,9-dimethyl-4,7-phenylbenzene-1, and 10-phenanthroline (BCP), the thickness of hole blocking layer 4 is 30nm;
The material of electron transfer layer 5 is Alq
3, Alq
3be oxine aluminium, the thickness of electron transfer layer 5 is 30nm;
The material of electron injecting layer 6 is LiF; The thickness of electron injecting layer 6 is 1.5nm;
The material of cathode layer 7 is Al; The thickness of cathode layer 7 is 150nm.
Therefore, described organic electroluminescence device can be expressed as: ITO/PEDOT:PSS/P1:FIrpic/BCP/Alq
3/ LiF/Al.
The concrete grammar that this organic electroluminescence device is made is:
Spin coating PEDOT:PSS first on the ITO layer of the anode conducting glass substrate through cleaning, after PEDOT:PSS is dry, PEDOT:PSS surface stacks gradually evaporation P1:FIrpic, BCP, Alq again
3, LiF and Al.
Electric current-brightness-voltage characteristic to prepared organic electroluminescence device is tested, and wherein electric current-brightness-voltage characteristic is to be completed by the Keithley source measuring system with correction silicon photoelectric diode (Keithley2400 Sourcemeter, Keithley 2000 Cuirrentmeter).Test result shows: the maximum current efficiency of this organic electroluminescence device is 6.7cd/A, and high-high brightness is 18320cd/m
2.
The above embodiment has only expressed several embodiment of the present invention, and it describes comparatively concrete and detailed, but can not therefore be interpreted as the restriction to the scope of the claims of the present invention.It should be pointed out that for the person of ordinary skill of the art, without departing from the inventive concept of the premise, can also make some distortion and improvement, these all belong to protection scope of the present invention.Therefore, the protection domain of patent of the present invention should be as the criterion with claims.
Claims (9)
1. a bipolarity blue emitting phosphor material with following structural formula:
In formula, R is C
1～C
20alkyl, the integer that n is 10-100.
2. the preparation method of bipolarity blue emitting phosphor material according to claim 1, is characterized in that, comprises the steps:
Under oxygen-free environment, by structural formula, be
compd A and structural formula be
compd B add in organic solvent and to dissolve after, add again subsequently catalyzer and alkaline solution, and at 70～130 ℃, carry out Suzuki coupling reaction 12～96 hours, stopped reaction cool to room temperature, separating-purifying reaction solution, obtains structural formula and is
described bipolarity blue emitting phosphor material; Wherein, the mol ratio of compd A and compd B is 1:1 ~ 1.2; In formula, R is C
1～C
20alkyl, the integer that n is 10-100.
3. the preparation method of bipolarity blue emitting phosphor material according to claim 2, is characterized in that, described organic solvent is at least one in toluene, DMF, tetrahydrofuran (THF).
4. the preparation method of bipolarity blue emitting phosphor material according to claim 2, is characterized in that, described catalyzer is bi triphenyl phosphine dichloride palladium or tetra-triphenylphosphine palladium; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
5. the preparation method of bipolarity blue emitting phosphor material according to claim 2, it is characterized in that, described catalyzer is that mol ratio is three or two argon benzyl acetone two palladiums and the 2-dicyclohexyl phosphine-2 ' that the palladium of 1:4 ~ 8 and tri-o-tolyl phosphine mixture or mol ratio are 1:4 ~ 8,6 '-dimethoxy-biphenyl mixture; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1: 100.
6. the preparation method of bipolarity blue emitting phosphor material according to claim 2, is characterized in that, described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate and sodium hydrogen carbonate solution; The volumetric molar concentration of described alkaline solution is 2mol/L; In described alkaline solution, the mol ratio of alkali and compd A is 20:1.
7. the preparation method of bipolarity blue emitting phosphor material according to claim 2, is characterized in that, the temperature of reaction of described Suzuki coupling reaction is 90～120 ℃, and the reaction times is 24～72 hours.
8. the preparation method of bipolarity blue emitting phosphor material according to claim 2, is characterized in that, described Suzuki coupling reaction stops and cool to room temperature, and separating-purifying reaction solution comprises the steps:
After Suzuki coupling reaction stops, in reaction solution, add methyl alcohol precipitating, and use successively methyl alcohol and normal hexane extracting after filtering by apparatus,Soxhlet's, then take chloroform as solvent extraction is to colourless, collect chloroformic solution and be spin-dried for and obtain solid, by described solid 50 ℃ of dry 24h under vacuum, obtain described bipolarity blue emitting phosphor material.
9. an organic electroluminescence device, comprise the anode conducting substrate, hole injection layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer and the cathode layer that stack gradually, it is characterized in that, the material of described luminescent layer is two (4,6-difluorophenyl pyridine-N, C2) pyridine formyl closes iridium and according to 10% mass percent, is doped to the doping mixing material obtaining in the bipolarity blue emitting phosphor material that following structural formula represents:
In above-mentioned formula, R is C
1～C
20alkyl, the integer that n is 10-100.
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Cited By (1)
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| CN115536769A (en) * | 2021-06-29 | 2022-12-30 | 京东方科技集团股份有限公司 | Blue light host material and preparation method thereof, light-emitting layer material, organic electroluminescent device and display device |
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| CN115536769A (en) * | 2021-06-29 | 2022-12-30 | 京东方科技集团股份有限公司 | Blue light host material and preparation method thereof, light-emitting layer material, organic electroluminescent device and display device |
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Application publication date: 20140903 |