CN104629015A - Bipolar blue-ray phosphorescent polymer, as well as preparation method and organic electroluminescent device thereof - Google Patents
Bipolar blue-ray phosphorescent polymer, as well as preparation method and organic electroluminescent device thereof Download PDFInfo
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- CN104629015A CN104629015A CN201310568052.4A CN201310568052A CN104629015A CN 104629015 A CN104629015 A CN 104629015A CN 201310568052 A CN201310568052 A CN 201310568052A CN 104629015 A CN104629015 A CN 104629015A
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Abstract
The invention belongs to the field of organic electroluminescent materials, and discloses a bipolar blue-ray phosphorescent polymer, as well as a preparation method and an organic electroluminescent device thereof. The material has a structural formula as shown in the specification, wherein R is alkyl of C1-C20, and n is an integer from 10 to 100. In the bipolar blue-ray phosphorescent polymer, fluorene is of a copular biphenyl structure which has a relatively large rigidity and triplet state level, triazole is a relatively good electron transmission unit, silafluorene is introduced onto the main chain of polytriazole, and the luminescence efficiency of the organic electroluminescent device can be improved.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, particularly relate to a kind of bipolarity blue emitting phosphor polymkeric substance and preparation method thereof.The invention still further relates to a kind of this compound that uses as the organic electroluminescence device of luminescent layer material of main part.
Background technology
Prepared with Alq by evaporation coating method from people's reported first such as Kodak C.W.Tang in 1987
3since bi-layer devices structure for luminescent material, organic electroluminescent just obtains the very big concern of people.Organic electroluminescent can be divided into fluorescence and phosphorescence electroluminescent.According to spin quantum statistical theory, the formation probability ratio of singlet excitons and triplet exciton is 1:3, and namely singlet excitons only accounts for 25% of " electron-hole pair ".Therefore, the fluorescence coming from the radiative transition of singlet excitons just only accounts for 25% of total input energy, and the electroluminescent of phosphor material just can utilize the energy of whole exciton, thus has larger superiority.Mostly adopt Subjective and Objective structure in present electrophosphorescence device, by phosphorescent emissions material with certain doped in concentrations profiled in main substance, burying in oblivion of triplet state-triplet state can be avoided, but phosphorescent emissions efficiency is lower.
Summary of the invention
Problem to be solved by this invention is the bipolarity blue emitting phosphor polymkeric substance providing a kind of phosphorescent emissions efficiency higher.
For achieving the above object, bipolarity blue emitting phosphor polymkeric substance provided by the invention, its structure is such as formula as follows:
in formula, R is C
1~ C
20alkyl, n is the integer of 10-100.
Another object of the present invention is to provide the preparation method of the bipolarity blue emitting phosphor polymkeric substance that a kind of synthetic route is simple, material is cheap and easy to get, described preparation method comprises the steps:
The compd A providing following structural formula to represent respectively and B,
wherein, R is C
1~ C
20alkyl;
Under oxygen-free environment, compd A and B are added in the organic solvent containing catalyzer and alkaline solution and dissolve, compd A and B mol ratio are 1:1 ~ 1.2, the mixing solutions obtained after dissolving carries out Suzuki coupling reaction 12 ~ 96 hours at 70 ~ 130 DEG C, stopped reaction cool to room temperature, separating-purifying reaction solution, obtains bipolarity blue emitting phosphor polymkeric substance described in following structural formula:
In formula, R is C
1~ C
20alkyl, n is the integer of 10-100.
Wherein, described catalyzer is bis-triphenylphosphipalladium palladium dichloride or tetra-triphenylphosphine palladium; Or,
Described catalyzer is the mixture of organic palladium and organophosphorus ligand, and the mol ratio of described organic palladium and organophosphorus ligand is 1:4 ~ 8; Described organic palladium is palladium or three or two argon benzyl acetone two palladiums, and described organophosphorus ligand is three (o-methyl-phenyl-) phosphines or 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl; Preferably, described mixture is the mixture of palladium and tri-o-tolyl phosphine, or described mixture is three or two argon benzyl acetone two palladiums and 2-dicyclohexyl phosphine-2 ', the mixture of 6 '-dimethoxy-biphenyl.
The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
In described preparation method, described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate and sodium hydrogen carbonate solution; In described alkaline solution, the mol ratio of alkali solute and described compd A is 20:1.
In a preferred embodiment, organic solvent is selected from solvent is at least one in toluene, DMF, tetrahydrofuran (THF).
In a preferred embodiment, the temperature of reaction of Suzuki coupling reaction is 90 ~ 120 DEG C, and the reaction times is 36 ~ 60 hours.
In a preferred embodiment, described separating-purifying reaction solution comprises:
After Suzuki coupling reaction stops, methyl alcohol precipitating is added in reaction solution, methyl alcohol and normal hexane extracting is used successively after being filtered by apparatus,Soxhlet's, then be that solvent extraction is to colourless with chloroform, collect chloroformic solution and be spin-dried for and obtain pressed powder, this pressed powder, under vacuo after 50 DEG C of dry 24h, obtains described bipolarity blue emitting phosphor polymkeric substance.
In described preparation method, oxygen-free environment is made up of at least one gas in argon gas, nitrogen.
Above-mentioned preparation method's principle is simple, easy and simple to handle, low for equipment requirements, can wide popularization and application.
Another object of the present invention is to provide a kind of organic electroluminescence device, the material of main part of its luminescent layer adulterates the mixing material of guest materials composition of 10% mass percent, described material of main part is bipolarity blue emitting phosphor polymkeric substance according to claim 1, described guest materials is two (4,6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic conjunction iridium.
In bipolarity blue emitting phosphor polymkeric substance provided by the invention, fluorenes is plane biphenyl structural, and this structure has larger rigidity and triplet; Triazole is a good electric transmission unit, by introducing silicon fluorenes on polytriazoles main chain, thus improves the luminous efficiency of organic electroluminescence device.
The preparation method of above-mentioned bipolarity blue emitting phosphor polymkeric substance, have employed better simply synthetic route, thus 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 polymkeric substance that embodiment 1 obtains;
Fig. 2 is the organic electroluminescence device structural representation that embodiment 6 obtains.
Embodiment
In order to understand the content of patent of the present invention better, technology case of the present invention is further illustrated below by concrete example and legend, specifically comprise material preparation and device preparation, but these embodiments do not limit the present invention, wherein, compd A, compd B are all purchased from Taiwan Jiguang Technology Corporation.
Embodiment 1:
The bipolarity blue emitting phosphor polymkeric substance of the present embodiment, namely { 5 are gathered, 5-di-n-hexyl-3,7-bis-base-5H-dibenzo [b, d] Silole-co-3,5-bis-(4-base-phenyl)-4-phenyl-4H-1,2,4-triazole } (P1) (wherein, R is n-hexyl, n=57), 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 5,5-di-n-hexyl-3,7-bis-tetramethyl ethylene ketone boric acid ester-5H-dibenzo [b, d] Silole (121mg, 0.2mmol), 3,5-bis-(4-bromophenyl)-4-phenyl-4H-1,2,4-triazole (91mg, 0.2mmol) add in the flask filling 10ml toluene solvant, after abundant dissolving, salt of wormwood (2mL, 2mol/L) solution is joined in flask, vacuumize deoxygenation and be filled with argon gas, then bis-triphenylphosphipalladium palladium dichloride (5.6mg, 0.008mmol) is added; Flask is heated to 100 DEG C and carries out Suzuki coupling reaction 48h.Subsequently, after cooling, stop polyreaction, drip in flask in 50ml methyl alcohol and carry out sedimentation; Methyl alcohol and normal hexane extracting 24h is used successively after being filtered by apparatus,Soxhlet's.Then be solvent extraction with chloroform to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, after collection, obtain product P 1, productive rate 82% after 50 DEG C of dry 24h under vacuo.
Test result is: Molecular weight (GPC, THF, R.I): M
n=38.1kDa, M
w/ M
n=2.2.
Fig. 1 is the thermogravimetic analysis (TGA) figure of the bipolarity blue emitting phosphor polymkeric substance that embodiment 1 obtains; Thermogravimetic analysis (TGA) is completed by the measurement of Perkin-Elmer Series7 Thermo System, and all measurements all complete in atmosphere at room temperature.As shown in Figure 1, the thermal weight loss temperature (T of bipolarity blue emitting phosphor polymkeric substance 10%
d) be 407 DEG C.
Embodiment 2: the bipolarity blue emitting phosphor polymkeric substance of the present embodiment, namely { 5 are gathered, 5-bis-NSC 62789 base-3,7-bis-base-5H-dibenzo [b, d] Silole-co-3,5-bis-(4-base-phenyl)-4-phenyl-4H-1,2,4-triazole } (P2) (wherein, R is NSC 62789 base, n=79), 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 argon gas gas mixture are protected, by 5, 5-bis-NSC 62789 base-3, 7-bis-tetramethyl ethylene ketone boric acid ester-5H-dibenzo [b, d] Silole (299mg, 0.3mmol), 3, 5-bis-(4-base-phenyl)-4-phenyl-4H-1, 2, 4-triazole (137mg, 0.3mmol) add in the two-mouth bottle of 50mL specification with 15mL tetrahydrofuran (THF), after the gas mixture air-discharging passing into nitrogen and argon gas after abundant dissolving is about 20min, then by tetra-triphenylphosphine palladium (4mg, 0.003mmol) add wherein, sodium bicarbonate (3mL is added again after abundant dissolving, 2mol/L) solution.After the gas mixture air-discharging of fully logical nitrogen and argon gas is about 10min again, two-mouth bottle is joined 70 DEG C and carry out Suzuki coupling reaction 96h.Subsequently, after cooling, stop polyreaction, in two-mouth bottle, add 40mL methyl alcohol precipitating, after being filtered by apparatus,Soxhlet's, use methyl alcohol and normal hexane extracting 24h successively.Then be solvent extraction with chloroform to colourless, collect chloroformic solution and be spin-dried for and obtain red solid, after collection, obtain product P 2 after 50 DEG C of dry 24h under vacuo.Productive rate is 86%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=74.7kDa, M
w/ M
n=2.1.
Embodiment 3: the bipolarity blue emitting phosphor polymkeric substance of the present embodiment, namely { 5 are gathered, 5-dimethyl-3,7-bis-base-5H-dibenzo [b, d] Silole-co-3,5-bis-(4-base-phenyl)-4-phenyl-4H-1,2,4-triazole } (P3) (wherein, R is methyl, n=57), 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 5,5-dimethyl-3,7-bis-tetramethyl ethylene ketone boric acid ester-5H-dibenzo [b, d] Silole (139mg, 0.3mmol), 3,5-bis-(4-base-phenyl)-4-phenyl-4H-1,2,4-triazole (150mg, 0.33mmol), palladium (3.5mg, 0.015mmol) and three (o-methyl-phenyl-) phosphine (21mg, 0.06mmol) joins the N filling 12mL, in the flask of dinethylformamide, salt of wormwood (3mL, 2mol/L) solution is added, after logical nitrogen purge gas is about 30min in flask subsequently after abundant dissolving; Flask is heated to 130 DEG C and carries out Suzuki coupling reaction 12h.Subsequently, after cooling, stop polyreaction, in flask, add 40mL methyl alcohol precipitating, after being filtered by apparatus,Soxhlet's, use methyl alcohol and normal hexane extracting 24h successively; Then be solvent extraction with chloroform to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, after collection under vacuo after 50 DEG C of dry 24h, be product P 3, productive rate 78%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=35.6kDa, M
w/ M
n=2.1.
Embodiment 4: the bipolarity blue emitting phosphor polymkeric substance of the present embodiment, namely { 5 are gathered, positive decyl-3,7-bis-base-5H-dibenzo [b, the d] Silole-co-3 of 5-bis-, 5-bis-(4-base-phenyl)-4-phenyl-4H-1,2,4-triazole } (P4) (wherein, R is positive decyl, 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 5; the positive decyl-3 of 5-bis-; 7-bis-tetramethyl ethylene ketone boric acid ester-5H-dibenzo [b; d] Silole (215mg; 0.3mmol), 3,5-bis-(4-base-phenyl)-4-phenyl-4H-1,2; 4-triazole (164mg; 0.36mmol), three or two argon benzyl acetones two palladium (9mg, 0.009mmol) and 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl (29mg; 0.072mmol) join the N filling 12mL; in the flask of dinethylformamide, after fully dissolving, add sodium bicarbonate (3mL, 2mol/L) solution.After in flask, logical nitrogen purge gas is about 30min subsequently; Flask is heated to 120 DEG C and carries out Suzuki coupling reaction 36h.Subsequently, after cooling, stop polyreaction, in flask, add 40mL methyl alcohol precipitating, after being filtered by apparatus,Soxhlet's, use methyl alcohol and normal hexane extracting 24h successively; Then be solvent extraction with chloroform to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, after collection under vacuo after 50 DEG C of dry 24h, be product P 4, productive rate is 84%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=14.5kDa, M
w/ M
n=2.4.
Embodiment 5: the bipolarity blue emitting phosphor polymkeric substance of the present embodiment, namely { 5 are gathered, 5-di-n-octyl-3,7-bis-base-5H-dibenzo [b, d] Silole-co-3,5-bis-(4-base-phenyl)-4-phenyl-4H-1,2,4-triazole } (P5) (wherein, R is n-octyl, 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 and argon gas gas mixture are protected; by 5; 5-di-n-octyl-3; 7-bis-tetramethyl ethylene ketone boric acid ester-5H-dibenzo [b; d] Silole (198mg; 0.3mmol), 3; 5-bis-(4-base-phenyl)-4-phenyl-4H-1,2,4-triazole (164mg; 0.36mmol) add in the two-mouth bottle of 50mL specification with 15mL toluene; after the gas mixture air-discharging passing into nitrogen and argon gas after abundant dissolving is about 20min, then tetra-triphenylphosphine palladium (8mg, 0.006mmol) is added wherein; add salt of wormwood (3mL, 2mol/L) solution again.After the gas mixture air-discharging of fully logical nitrogen and argon gas is about 10min again, two-mouth bottle is joined 90 DEG C and carry out Suzuki coupling reaction 60h.Subsequently, after cooling, stop polyreaction, in two-mouth bottle, add 40mL methyl alcohol precipitating, after being filtered by apparatus,Soxhlet's, use methyl alcohol and normal hexane extracting 24h successively.Then be solvent extraction with chloroform to colourless, collect chloroformic solution and be spin-dried for and obtain red solid, after collection, obtain product P 5 after 50 DEG C of dry 24h under vacuo.Productive rate is 81%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=70.8kDa, M
w/ M
n=2.0.
Embodiment 6:
The present embodiment is organic electroluminescence device, the material of main part of its luminescent layer is the bipolarity blue emitting phosphor polymkeric substance that the present invention obtains, what preferred embodiment 1 was obtained gathers { 5,5-di-n-hexyl-3,7-bis-base-5H-dibenzo [b, d] Silole-co-3,5-bis-(4-base-phenyl)-4-phenyl-4H-1,2,4-triazole }.
As shown in Figure 2, the structure of this organic electroluminescence device comprises conductive anode substrate 1 and is sequentially laminated on the hole injection layer 2 of conductive anode substrate, luminescent layer 3, electric transmission/hole blocking layer 4, electron injecting layer 5, cathode layer 6; Wherein:
Conductive anode substrate 1 comprises with substrate of glass, and is deposited on the conductive anode layer of glass basic surface, and the material changing conductive anode layer is indium tin oxide (ITO); Therefore, this conductive anode substrate is also called ito glass;
The material of hole injection layer 2 is PEDOT:PSS;
The material of luminescent layer 3 is poly-{ 5,5-di-n-hexyl-3,7-bis-base-5H-dibenzo [b, d] Silole-co-3,5-bis-(4-base-phenyl)-4-phenyl-4H-1,2,4-triazole } (representing with P1) adulterate two (4 of 10% mass percent, 6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic closes iridium (FIrpic) dopant mixture that forms, is expressed as P1:FIrpic;
The material of electric transmission/hole blocking layer 4 is 1,3,5-tri-(1-phenyl-1H-benzimidazolyl-2 radicals-Ji) benzene (TPBI);
The material of electron injecting layer 5 is LiF;
The material of cathode layer 6 is Al.
The concrete grammar that this organic electroluminescence device makes is:
First, spin coating PEDOT:PSS successively in the conductive anode layer (ITO) of the conductive anode substrate through cleaning, obtained hole injection layer;
Secondly, evaporation luminescent layer (P1:FIrpic), electric transmission/hole blocking layer (TPBI), electron injecting layer (LiF), cathode layer (Al) is stacked gradually on hole injection layer surface; Therefore, the structure of this organic electroluminescence device can also be expressed as:
Glass/ITO(150nm)/PEDOT:PSS (30nm)/P1:FIrpic (20nm)/TPBI (30nm)/LiF (1.5nm)/Al (150nm); Wherein, brace is expressed as laminate structure, and the numeric representation in bracket is the one-tenth-value thickness 1/10 of each functional layer.
To the current versus brightness-voltage characteristic test of this organic electroluminescence device, be complete by with Keithley source measuring system (Keithley2400Sourcemeter) correcting silicon photoelectric diode, all measurements all complete in atmosphere at room temperature.Test result shows: the maximum current efficiency of device is 8.2cd/A, and high-high brightness is 20710cd/m
2.
The above embodiment only have expressed several embodiment of the present invention, and it describes comparatively concrete and detailed, but therefore can not 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 (10)
1. a bipolarity blue emitting phosphor polymkeric substance, is characterized in that, its structure is such as formula as follows:
In formula, R is C
1~ C
20alkyl, n is the integer of 10-100.
2. a preparation method for bipolarity blue emitting phosphor polymkeric substance as claimed in claim 1, it is characterized in that, its step is as follows:
The compd A providing following structural formula to represent respectively and B,
wherein, R is C
1~ C
20alkyl;
Under oxygen-free environment, be dissolve mol ratio during the compd A of 1:1 ~ 1.2 and B are added into containing catalyzer and alkaline solution organic solvent, the mixing solutions obtained carries out Suzuki coupling reaction 12 ~ 96 hours at 70 ~ 130 DEG C, stopped reaction cool to room temperature, separating-purifying reaction solution, obtains the described bipolarity blue emitting phosphor polymkeric substance described in following structural formula:
In formula, R is C
1~ C
20alkyl, n is the integer of 10-100.
3. the preparation method of bipolarity blue emitting phosphor polymkeric substance according to claim 2, is characterized in that, described catalyzer is bis-triphenylphosphipalladium palladium dichloride or tetra-triphenylphosphine palladium; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
4. the preparation method of bipolarity blue emitting phosphor polymkeric substance according to claim 2, is characterized in that, described catalyzer is mol ratio is the organic palladium of 1:4 ~ 8 and the composition mixture of organophosphorus ligand; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
5. the preparation method of bipolarity blue emitting phosphor polymkeric substance according to claim 4, it is characterized in that, described organic palladium is palladium or three or two argon benzyl acetone two palladiums, described organophosphorus ligand is three (o-methyl-phenyl-) phosphines or 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl.
6. the preparation method of bipolarity blue emitting phosphor polymkeric substance according to claim 5, it is characterized in that, described mixture is the mixture of palladium and tri-o-tolyl phosphine, or described mixture is three or two argon benzyl acetone two palladiums and 2-dicyclohexyl phosphine-2 ', the mixture of 6 '-dimethoxy-biphenyl.
7. the preparation method of bipolarity blue emitting phosphor polymkeric substance according to claim 2, it 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; In described alkaline solution, the mol ratio of alkali solute and described compd A is 20:1;
Described organic solvent is selected from as at least one in toluene, DMF, tetrahydrofuran (THF).
8. the preparation method of bipolarity blue emitting phosphor polymkeric substance according to claim 2, is characterized in that, the temperature of reaction of Suzuki coupling reaction is 90 ~ 120 DEG C, and the reaction times is 36 ~ 60 hours.
9. the preparation method of bipolarity blue emitting phosphor polymkeric substance according to claim 2, is characterized in that, described separating-purifying reaction solution comprises:
After Suzuki coupling reaction stops, methyl alcohol precipitating is added in reaction solution, methyl alcohol and normal hexane extracting is used successively after being filtered by apparatus,Soxhlet's, then be that solvent extraction is to colourless with chloroform, collect chloroformic solution and be spin-dried for and obtain pressed powder, this pressed powder, under vacuo after 50 DEG C of dry 24h, obtains described bipolarity blue emitting phosphor polymkeric substance.
10. an organic electroluminescence device, it is characterized in that, the material of its luminescent layer is that material of main part adulterates the mixing material of guest materials composition of 10% mass percent, described material of main part is bipolarity blue emitting phosphor polymkeric substance according to claim 1, described guest materials is two (4,6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic conjunction iridium.
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