CN104292423A - Bipolar copolymer host material, preparation method thereof and organic electroluminescent device - Google Patents
Bipolar copolymer host material, preparation method thereof and organic electroluminescent device Download PDFInfo
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Abstract
Belonging to the field of organic semiconductors, the invention discloses a bipolar copolymer host material, a preparation method thereof and an organic electroluminescent device. The structural general formula of the host material is shown as the specification, wherein n is an integer of 13-94. In the bipolar copolymer host material provided by the invention, a phosphine-oxygen group has a tetrahedral configuration, and is a good electron transmission unit; carbazole is an electron-rich nitrogen heteroaromatic compound and has very good hole transport ability, and through alkyl or phenyl modification on N, and introduction of carbazole to a phosphine-oxygen group polymer main chain, carrier balance of the electroluminescent device can be realized, thereby solving the low efficiency problem of the organic electroluminescent device.
Description
Technical field
The present invention relates to organic semiconductor material field, particularly relate to a kind of bipolarity multipolymer material of main part and preparation method thereof.The invention still further relates to a kind of this bipolarity multipolymer material of main part 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, to avoid burying in oblivion of triplet state-triplet state, improve phosphorescent emissions efficiency.At present, the material of main part in electroluminescent device mainly contains small molecule host material and polymer host material two class, its poor heat stability, and luminous efficiency is low.
Summary of the invention
Based on the problems referred to above, problem to be solved by this invention is to provide a kind of Heat stability is good, the bipolarity multipolymer material of main part that luminous efficiency is high.
Technical scheme of the present invention is as follows:
A kind of bipolarity multipolymer material of main part provided by the invention, its general structure is as follows:
In formula, n is the integer of 13-94
Another object of the embodiment of the present invention is the preparation method providing a kind of bipolarity multipolymer material of main part, comprises the steps:
The compd A providing following structural formula to represent respectively and B,
A:
i.e. 9-phenyl-3-(9-phenyl-2,7-bis-tetramethyl ethylene ketone boric acid ester-9H-fluorenes-9-base)-9H-carbazole alkane;
B:
i.e. (4,4'-(2,7-bis-bromo-9H-fluorenes-9,9-bis-base) two (4,1-penylenes)) two (diphenyl phosphine oxygen);
Under oxygen-free environment (oxygen-free environment of at least one gas composition in preferred argon gas, nitrogen), be after dissolving during the compd A of 1:1 ~ 1.2 and B are added into containing catalyzer and alkaline solution organic solvent by mol ratio, Suzuki coupling reaction is carried out 12 ~ 96 hours at 70 ~ 130 DEG C, polyreaction is stopped after cooling, through separating-purifying reaction solution, obtain the described bipolarity multipolymer material of main part of following general structure:
In formula, n is the integer of 13-94.
Wherein, described catalyzer is described catalyzer is bis-triphenylphosphipalladium palladium dichloride, tetra-triphenylphosphine palladium; Or
Palladium and the tri-o-tolyl phosphine mixture of described catalyzer to be mol ratio be 1:4 ~ 8, or mol ratio is three or two argon benzyl acetone two palladiums and the 2-dicyclohexyl phosphine-2 of 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, and in described alkaline solution, the mol ratio of alkali solute and 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, Suzuki coupling reaction is at 90 ~ 120 DEG C, reacts 36 ~ 60 hours.
In a preferred embodiment, separating-purifying reaction solution comprises step:
After 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 powder, powder after collection under vacuo after 50 DEG C of dry 24h, obtains described bipolarity multipolymer material of main part again.
The present invention also provides a kind of organic electroluminescence device, the material of its luminescent layer is two (4,6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic close iridium (III) according to 8% mass percent be doped to the dopant mixture formed in the bipolarity multipolymer material of main part of following structural formula:
In formula, n is the integer of 13-94.
In bipolarity multipolymer material of main part of the present invention, phosphine oxygen groups has four sides configuration, is a good electric transmission unit; Carbazole is the nitrogen heteroaromatic compound that a class contains electron rich, there is good cavity transmission ability, N is upper can pass through alkyl or phenyl modification, phosphine oxygen based polyalcohol main chain introduces carbazole, realize the carrier balance of electroluminescent device, thus solve organic electroluminescence device low efficiency problem.
The preparation method of above-mentioned bipolarity multipolymer material of main part, have employed better simply synthetic route, thus reduces technical process, and starting material are cheap and easy to get, and manufacturing cost is reduced; And obtained polymeric material constructions is novel, solubility property is good, and film forming properties is excellent, is applicable to organic electroluminescence device.This material has higher electroluminescent efficiency.
Accompanying drawing explanation
Fig. 1 is the differential scanning calorimetric curve of the bipolarity multipolymer material of main part that embodiment 1 obtains;
Fig. 2 is the structural representation of the organic electroluminescence device 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 commercially obtain.
Embodiment 1:
The bipolarity multipolymer material of main part of the present embodiment, i.e. poly-{ 9-phenyl-3-(9-phenyl-2,7-bis-base-9H-fluorenes-9-base)-9H-carbazole-co-(4,4'-(2,7-bis-base-9H-fluorenes-9,9-bis-base) two (4,1-penylenes)) two (diphenyl phosphine oxygen) (representing with P1) (wherein, n=48), 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 9-phenyl-3-(9-phenyl-2,7-bis-tetramethyl ethylene ketone boric acid ester-9H-fluorenes-9-base)-9H-carbazole (147mg, 0.2mmol), (4,4'-(2, the bromo-9H-fluorenes-9 of 7-bis-, 9-bis-base) two (4,1-penylene)) two (diphenyl phosphine oxygen) (175mg, 0.2mmol) add in the flask filling 10ml toluene solvant, by salt of wormwood (2mL after fully dissolving, 2mol/L) solution joins in flask, vacuumize deoxygenation and be filled with argon gas, then adding bis-triphenylphosphipalladium palladium dichloride (5.6mg, 0.008mmol); 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 that solvent extraction is extremely colourless with chloroform, collect chloroformic solution and be spin-dried for obtain red powder, after collection, 50 DEG C of dry 24h obtain P1 product under vacuo, productive rate 82%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=52.7kDa, M
w/ M
n=2.2.
Fig. 1 is the differential scanning calorimetric curve of the bipolarity multipolymer material of main part that embodiment 1 obtains; Wherein, differential scanning calorimetric curve (DSC) is completed by the measurement of Perkin-Elmer DSC-7 Thermo System, has tested in atmosphere at room temperature.As shown in Figure 1, the second-order transition temperature (T of bipolarity multipolymer material of main part
g) be 133 DEG C.
Embodiment 2:
The bipolarity multipolymer material of main part of the present embodiment, i.e. poly-{ 9-phenyl-3-(9-phenyl-2,7-bis-base-9H-fluorenes-9-base)-9H-carbazole-co-(4,4'-(2,7-bis-base-9H-fluorenes-9,9-bis-base) two (4,1-penylenes)) two (diphenyl phosphine oxygen) (representing with P2) (wherein, n=13), 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 9-phenyl-3-(9-phenyl-2, 7-bis-tetramethyl ethylene ketone boric acid ester-9H-fluorenes-9-base)-9H-carbazole (221mg, 0.3mmol), (4, 4'-(2, the bromo-9H-fluorenes-9 of 7-bis-, 9-bis-base) two (4, 1-penylene)) two (diphenyl phosphine oxygen) (263mg, 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 P2 product after 50 DEG C of dry 24h under vacuo.Productive rate is 77%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=14.5kDa, M
w/ M
n=2.4.
Embodiment 3:
The bipolarity multipolymer material of main part of the present embodiment, i.e. poly-{ 9-phenyl-3-(9-phenyl-2,7-bis-base-9H-fluorenes-9-base)-9H-carbazole-co-(4,4'-(2,7-bis-base-9H-fluorenes-9,9-bis-base) two (4,1-penylenes)) two (diphenyl phosphine oxygen) (representing with P3) (wherein, n=94), 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 9-phenyl-3-(9-phenyl-2, 7-bis-tetramethyl ethylene ketone boric acid ester-9H-fluorenes-9-base)-9H-carbazole (221mg, 0.3mmol), (4, 4'-(2, the bromo-9H-fluorenes-9 of 7-bis-, 9-bis-base) two (4, 1-penylene)) two (diphenyl phosphine oxygen) (289mg, 0.33mmol), palladium (3.5mg, 0.015mmol) He three (o-methoxyphenyl) phosphine (21mg, 0.06mmol) join the N filling 12mL, in the flask of dinethylformamide, salt of wormwood (3mL is added after abundant dissolving, 2mol/L) solution, after in flask, logical nitrogen purge gas is about 30min subsequently, 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 P3 product, productive rate 83%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=95.8kDa, M
w/ M
n=2.0.
Embodiment 4:
The bipolarity multipolymer material of main part of the present embodiment, i.e. poly-{ 9-phenyl-3-(9-phenyl-2,7-bis-base-9H-fluorenes-9-base)-9H-carbazole-co-(4,4'-(2,7-bis-base-9H-fluorenes-9,9-bis-base) two (4,1-penylenes)) two (diphenyl phosphine oxygen) (representing with P4) (wherein, n=71), 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 9-phenyl-3-(9-phenyl-2, 7-bis-tetramethyl ethylene ketone boric acid ester-9H-fluorenes-9-base)-9H-carbazole (221mg, 0.3mmol), (4, 4'-(2, the bromo-9H-fluorenes-9 of 7-bis-, 9-bis-base) two (4, 1-penylene)) two (diphenyl phosphine oxygen) (315mg, 0.36mmol), three or two argon benzyl acetone two palladium (9mg, 0.009mmol) with 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl (29mg, 0.072mmol) join the N filling 12mL, in the flask of dinethylformamide, sodium bicarbonate (3mL is added after abundant dissolving, 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 P4 product, productive rate is 72%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=81.5kDa, M
w/ M
n=2.1.
Embodiment 5:
The bipolarity multipolymer material of main part of the present embodiment, i.e. poly-{ 9-phenyl-3-(9-phenyl-2,7-bis-base-9H-fluorenes-9-base)-9H-carbazole-co-(4,4'-(2,7-bis-base-9H-fluorenes-9,9-bis-base) two (4,1-penylenes)) two (diphenyl phosphine oxygen) (representing with P5) (wherein, n=26), 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 9-phenyl-3-(9-phenyl-2, 7-bis-tetramethyl ethylene ketone boric acid ester-9H-fluorenes-9-base)-9H-carbazole (221mg, 0.3mmol), (4, 4'-(2, the bromo-9H-fluorenes-9 of 7-bis-, 9-bis-base) two (4, 1-penylene)) two (diphenyl phosphine oxygen) (315mg, 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 by tetra-triphenylphosphine palladium (8mg, 0.006mmol) add wherein, add salt of wormwood (3mL again, 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 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 P5 product after 50 DEG C of dry 24h under vacuo.Productive rate is 76%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=46.4kDa, M
w/ M
n=2.3.
Embodiment 6:
The present embodiment is organic electroluminescence device, the multipolymer material of main part that its luminescent layer adopts embodiment 1 obtained, i.e. poly-{ 9-phenyl-3-(9-phenyl-2,7-bis-base-9H-fluorenes-9-base)-9H-carbazole-co-(4,4'-(2,7-bis-base-9H-fluorenes-9,9-bis-base) two (4,1-penylene)) two (diphenyl phosphine oxygen) } as the material of main part of luminescent layer, certainly, the arbitrary obtained multipolymer material of main part of embodiment 2 to 5 also can be selected.
As shown in Figure 2, this organic electroluminescence device comprises the structure stacked gradually: conductive substrate layer 1, hole injection layer 2, luminescent layer 3, hole blocking layer 4, electron transfer layer 5, electron injecting layer 6, cathode layer 7; Wherein, the material of each functional layer and thickness as follows:
Conductive substrate layer 1 comprises substrate, and is deposited on the anode layer of substrate surface; In the present embodiment, the material of substrate is preferably glass, and the material of anode layer is indium tin oxide (ITO), and itself and glass combine, and is called for short ito glass, and conventional ITO replaces; The thickness of ITO is 150nm;
The material of hole injection layer 2 is poly-3,4-ethylenedioxy thiazoles (PEDOT) and the mixture of polystyrene-sulfonic acid matrix material (PSS), is expressed as PEDOT:PSS; The thickness of hole injection layer 2 is 30nm;
The material of luminescent layer 3 is two (4,6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic closes iridium (III) (FIrpic) according to the obtained multipolymer material of main part of the embodiment 1 that is doped to of mass percent of 8%, i.e. poly-{ 9-phenyl-3-(9-phenyl-2,7-bis-base-9H-fluorenes-9-base)-9H-carbazole-co-(4,4'-(2,7-bis-base-9H-fluorenes-9,9-bis-base) two (4,1-penylenes)) two (diphenyl phosphine oxygen) } dopant mixture of composition in (representing with P1); 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-1,10-phenanthroline (BCP), and the thickness of hole blocking layer 3 is 30nm;
The material of electron transfer layer 5 is oxine aluminium (Alq
3); 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 aluminium, and the thickness of cathode layer 7 is 150nm.
The structure of this organic electroluminescence device can be expressed as:
Ito glass/PEDOT:PSS/P1:FIrpic/BCP/Alq
3/ LiF/Al; Wherein, brace "/" represents laminate structure.
The concrete grammar that this organic electroluminescence device makes is:
Spin coating PEDOT:PSS successively on conductive glass (ITO) substrate through cleaning, evaporation P1:FIrpic, BCP, Alq successively on its surface again after to be dried
3, LiF, Al, obtained organic electroluminescence device.
In room temperature, air, adopt Keithley source measuring system (Keithley2400Sourcemeter, Keithley2000Cuirrentmeter) with correcting silicon photoelectric diode, electroluminescent spectrum, by French JY company SPEX CCD3000 spectrometer measurement, carries out current versus brightness-voltage characteristic to the organic electroluminescence device of preparation and measures; Test result shows, and the maximum current efficiency of this organic electroluminescence device is 12.0cd/A, and high-high brightness is 25170cd/m
2.Result shows that multipolymer bulk material properties of the present invention is better, is a kind of very promising material of main part.
Should be understood that, the above-mentioned statement for present pre-ferred embodiments is comparatively detailed, and therefore can not think the restriction to scope of patent protection of the present invention, scope of patent protection of the present invention should be as the criterion with claims.
Claims (9)
1. a bipolarity multipolymer material of main part, is characterized in that, its general structure is as follows:
In formula, n is the integer of 13-94.
2. a preparation method for bipolarity multipolymer material of main part, is characterized in that, comprises the steps:
The compd A providing following structural formula to represent respectively and B,
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, Suzuki coupling reaction is carried out 12 ~ 96 hours at 70 ~ 130 DEG C, polyreaction is stopped after cooling, separating-purifying reaction solution, obtains the described bipolarity multipolymer material of main part of following general structure:
In formula, n is the integer of 13-94.
3. the preparation method of bipolarity multipolymer material of main part according to claim 2, is characterized in that, described catalyzer is bis-triphenylphosphipalladium palladium dichloride, tetra-triphenylphosphine palladium; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
4. the preparation method of bipolarity multipolymer material of main part according to claim 2, it is characterized in that, palladium and the tri-o-tolyl phosphine mixture of described catalyzer to be mol ratio be 1:4 ~ 8, or mol ratio is three or two argon benzyl acetone two palladiums and the 2-dicyclohexyl phosphine-2 of 1:4 ~ 8 ', 6 '-dimethoxy-biphenyl mixture; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
5. the preparation method of bipolarity multipolymer material of main part according to claim 2, is characterized in that, described alkaline solution is at 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 compd A is 20:1.
6. the preparation method of bipolarity multipolymer material of main part according to claim 2, it is characterized in that, described organic solvent is selected from least one in toluene, DMF, tetrahydrofuran (THF).
7. the preparation method of bipolarity multipolymer material of main part according to claim 2, is characterized in that, Suzuki coupling reaction temperature is at 90 ~ 120 DEG C, the reaction times is 36 ~ 60 hours.
8. the preparation method of bipolarity multipolymer material of main part according to claim 2, it is characterized in that, separating-purifying reaction solution comprises step:
After 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 powder, powder after collection under vacuo after 50 DEG C of dry 24h, obtains described bipolarity multipolymer material of main part again.
9. an organic electroluminescence device, it is characterized in that, the material of its luminescent layer be two (4,6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic close iridium according to 8% mass percent be doped to the dopant mixture formed in the bipolarity multipolymer material of main part of following structural formula:
in formula, n is the integer of 13-94.
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