CN104513376A - Bipolar polymer blue light host material, preparation method and applications thereof - Google Patents
Bipolar polymer blue light host material, preparation method and applications thereof Download PDFInfo
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Abstract
The invention belongs to the field of organic electroluminescent materials, and discloses a bipolar polymer blue light host material, a preparation method and applications thereof. The structural formula of the host material is shown in the description, wherein in the formula, the R1 and R2 both represent a C1-C20 alkyl group, and the n represents an integer in a range of 10 to 100. In the provided bipolar polymer blue light host material, the diphenyl phosphine oxide contains an electron-absorbing structure P=O, which is a good electron transmission unit; the carbazole is an important electroluminescent material, and has an excellent hole transmission performance, and the nitrogen atom of carbazole can be modified by an alkyl group so as to improve the solubility and film-forming performance of copolymerized carbazole. Dibenzofuran has a large planar and conjugated structure, which is benefit for the charge transmission. Phosphine oxide-carbazole is introduced into the main chain of dibenzofuran polymer so as to improve the luminescent efficiency of organic electroluminescent devices.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, particularly relate to a kind of Bipolar Polymer Blue-light emitting host material and its preparation method and application.
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, some phosphorescent emissions efficiency can be improved.But the luminous efficiency of this phosphor material is low.
Summary of the invention
Problem to be solved by this invention is to provide a kind of luminous efficiency higher good Bipolar Polymer Blue-light emitting host material.
Technical scheme of the present invention is as follows:
Bipolar Polymer Blue-light emitting host material provided by the invention, its structure is such as formula shown:
In formula, R
1, R
2be C
1~ C
20alkyl, n is the integer of 10 ~ 100.
The present invention also provides a kind of preparation method of Bipolar Polymer Blue-light emitting host material described above, comprises the steps:
The compd A providing following structural formula to represent respectively and B,
Under oxygen-free environment, be after the organic solvent dissolution that is added into containing catalyzer and alkaline solution of the compd A of 1:1 ~ 1.2 and B by mol ratio, Suzuki coupling reaction is carried out 12 ~ 96 hours at 70 ~ 130 DEG C, stopped reaction cool to room temperature, separating-purifying reaction solution, obtains the described Bipolar Polymer Blue-light emitting host material that following structural formula represents:
Wherein, R
1, R
2be C
1~ C
20alkyl, n is the integer of 10 ~ 100.
In the preparation method of described Bipolar Polymer Blue-light emitting host material, described catalyzer is bis-triphenylphosphipalladium palladium dichloride or tetra-triphenylphosphine palladium; Or described catalyzer is mol ratio is the organic palladium of 1:4 ~ 8 and the mixture of organophosphorus ligand, and 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; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
In the preparation method of described Bipolar Polymer Blue-light emitting host material, described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate and sodium hydrogen carbonate solution, and in alkaline solution, the mol ratio of alkali solute and compd A is 20:1.
In the preparation method of described Bipolar Polymer Blue-light emitting host material, described organic solvent is selected from least one in toluene, DMF, tetrahydrofuran (THF).
In the preparation method of described Bipolar Polymer Blue-light emitting host material, Suzuki coupling reaction, preferable reaction temperature is 90 ~ 120 DEG C, and the reaction times is 24 ~ 72 hours.
In the preparation method of described Bipolar Polymer Blue-light emitting host material, the oxygen-free environment of one or both compositions in described oxygen-free environment preferred nitrogen, argon gas.
In the preparation method of described Bipolar Polymer Blue-light emitting host material, separating-purifying reaction solution comprises:
After reaction stops, in reaction solution, add methyl alcohol carry out precipitating, then methyl alcohol and normal hexane extracting is used successively after the reaction solution after filtering precipitating by apparatus,Soxhlet's, then be solvent extracting again with chloroform, collect chloroformic solution and be spin-dried for, obtain red powder, the red powder after collection is 50 DEG C of dry 24h under vacuo, obtain described Bipolar Polymer Blue-light emitting host material.
The present invention also provides the application of above-mentioned Bipolar Polymer Blue-light emitting host material in organic electroluminescence device luminescent layer.
In Bipolar Polymer Blue-light emitting host material of the present invention, diphenylphosphine oxygen contains electrophilic P=O, is a good electric transmission unit; Carbazole is the important electroluminescent material of a class, and it has excellent hole transport performance, and N is upper can carry out alkyl modified, thus improves solubility property and the film forming properties of copolymerization carbazole; Benzo two furans has large plane and conjugated structure, is conducive to transferring charge.Benzo difuryl main polymer chain is introduced phosphine oxygen carbazole, thus be conducive to the luminous efficiency improving organic electroluminescence device.
The preparation method of above-mentioned Bipolar Polymer Blue-light emitting host material, 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 material structure is novel, solubility property is good, and film forming properties is excellent, and thermostability is high, is applicable to organic electroluminescence device.This material has higher electroluminescent efficiency.
Accompanying drawing explanation
Fig. 1 is the thermogravimetic analysis (TGA) figure of the Bipolar Polymer Blue-light emitting host material that embodiment 1 obtains;
Fig. 2 is the organic electroluminescence device structural representation of embodiment 6.
Embodiment
In order to understand the content of patent of the present invention better, further illustrate technology case of the present invention 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 and compd B are purchased from scientific and technological in lark prestige.
Embodiment 1: the Bipolar Polymer Blue-light emitting host material of the present embodiment, i.e. poly-{ 2,6-bis-(N, N-di-n-hexyl is amino)-3,7-dicyano benzo [1,2-b:4,5-b'] two furans-co-2,7-bis-base-3,6-bis-(diphenylphosphine oxygen)-9-n-hexyl-9H-carbazole } (P1) (wherein, R1, R2 are n-hexyl, n=41), 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 2,6-bis-(N, N-di-n-hexyl is amino)-3,7-dicyano-4,8-diiodo-benzo [1,2-b:4,5-b'] two furans (165mg, 0.2mmol), 2,7-bis-tetramethyl ethylene ketone boric acid ester-3,6-bis-(diphenylphosphine oxygen)-9-n-hexyl-9H-carbazole (162mg, 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 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 product P 1 under vacuo, productive rate 72%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=46.3kDa, M
w/ M
n=2.3.
Fig. 1 is the thermogravimetic analysis (TGA) figure of the Bipolar Polymer Blue-light emitting host material that embodiment 1 obtains; Wherein, thermogravimetic analysis (TGA) is completed by the measurement of Perkin-Elmer Series7 Thermo System, and measurement completes in atmosphere at room temperature.As shown in Figure 1, the thermal weight loss temperature (T of Bipolar Polymer Blue-light emitting host material 5%
d) be 451 DEG C.
Embodiment 2: the Bipolar Polymer Blue-light emitting host material of the present embodiment, i.e. poly-{ 2,6-bis-(N, N-dimethylamino)-3,7-dicyano benzo [1,2-b:4,5-b'] two furans-co-2,7-bis-base-3,6-bis-(diphenylphosphine oxygen)-9-NSC 62789 base-9H-carbazole } (P2) (wherein, R1 is methyl, and R2 is NSC 62789 base, 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 2, 6-bis-(N, N-dimethylamino)-3, 7-dicyano-4, 8-diiodo-benzo [1, 2-b:4, 5-b'] two furans (164mg, 0.3mmol), 2, 7-bis-tetramethyl ethylene ketone boric acid ester-3, 6-bis-(diphenylphosphine oxygen)-9-NSC 62789 base-9H-carbazole (302mg, 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 83%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=107.4kDa, M
w/ M
n=2.0.
Embodiment 3: the Bipolar Polymer Blue-light emitting host material of the present embodiment, i.e. poly-{ 2,6-bis-(N, N-bis-NSC 62789 base is amino)-3,7-dicyano benzo [1,2-b:4,5-b'] two furans-co-2,7-bis-base-3,6-bis-(diphenylphosphine oxygen)-9-methyl-9H-carbazole } (P3) (wherein, R1 is NSC 62789 base, and R2 is methyl, n=85), 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 2, 6-bis-(N, N-bis-NSC 62789 base is amino)-3, 7-dicyano-4, 8-diiodo-benzo [1, 2-b:4, 5-b'] two furans (484mg, 0.3mmol), 2, 7-bis-tetramethyl ethylene ketone boric acid ester-3, 6-bis-(diphenylphosphine oxygen)-9-methyl-9H-carbazole (244mg, 0.33mmol), palladium (3.5mg, 0.015mmol) He three (o-methyl-phenyl-) 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 78%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=145.1kDa, M
w/ M
n=2.1.
Embodiment 4: the Bipolar Polymer Blue-light emitting host material of the present embodiment, i.e. poly-{ 2,6-bis-(N, N-di-n-butyl is amino)-3,7-dicyano benzo [1,2-b:4,5-b'] two furans-co-2,7-bis-base-3,6-bis-(diphenylphosphine oxygen) the positive decyl of-9--9H-carbazole } (P4) (wherein, R1 is normal-butyl, and R2 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 2, 6-bis-(N, N-di-n-butyl is amino)-3, 7-dicyano-4, 8-diiodo-benzo [1, 2-b:4, 5-b'] two furans (214mg, 0.3mmol), 2, 7-bis-tetramethyl ethylene ketone boric acid ester-3, 6-bis-(diphenylphosphine oxygen) the positive decyl of-9--9H-carbazole (312mg, 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 24h.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 67%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=15.3kDa, M
w/ M
n=2.4.
Embodiment 5:
The Bipolar Polymer Blue-light emitting host material of the present embodiment, i.e. poly-{ 2,6-bis-(N, N-di-n-octyl is amino)-3,7-dicyano benzo [1,2-b:4,5-b'] two furans-co-2,7-bis-base-3,6-bis-(diphenylphosphine oxygen)-9-n-octyl-9H-carbazole } (P5) (wherein, R1, R2 are octane base, 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 and argon gas gas mixture are protected, by 2, 6-bis-(N, N-di-n-octyl is amino)-3, 7-dicyano-4, 8-diiodo-benzo [1, 2-b:4, 5-b'] two furans (281mg, 0.3mmol), 2, 7-bis-tetramethyl ethylene ketone boric acid ester-3, 6-bis-(diphenylphosphine oxygen)-9-n-octyl-9H-carbazole (301mg, 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 72h.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 86%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=134.4kDa, M
w/ M
n=2.0.
Embodiment 6:
Originally organic electroluminescence device is embodied as, its Bipolar Polymer Blue-light emitting host material obtained with the present invention, what preferred embodiment 1 was obtained gathers { 2,6-bis-(N, N-di-n-hexyl is amino)-3,7-dicyano benzo [1,2-b:4,5-b'] two furans-co-2,7-bis-base-3,6-bis-(diphenylphosphine oxygen)-9-n-hexyl-9H-carbazole } as the material of main part of luminescent layer, the Bipolar Polymer Blue-light emitting host material that embodiment 2 to 5 can certainly be adopted obtained is as the material of main part of luminescent layer.
As shown in Figure 2, this organic electroluminescence device comprises the substrate 1 be made up of glass and the conductive anode layer (ITO) that is layered in glass surface, and the hole injection layer 2(material being sequentially laminated on conductive anode layer surface is PEDOE:PSS), luminescent layer 3(material be the embodiment of the present invention 1 obtained poly-{ 2, 6-bis-(N, N-di-n-hexyl is amino)-3, 7-dicyano benzo [1, 2-b:4, 5-b'] two furans-co-2, 7-bis-base-3, 6-bis-(diphenylphosphine oxygen)-9-n-hexyl-9H-carbazole } (representing with P1) as two (4 of material of main part doping 14wt%, 6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic closes the mixing material that iridium (III) (FIrpic) forms, be expressed as P1:FIrpic), (material is 2 to hole blocking layer 4, 9-dimethyl-4, 7-phenylbenzene-1, 10-phenanthroline (BCP)), electron transfer layer 5(material is three-oxine aluminium (Alq
3)), electron injecting layer 6(material is lithium fluoride) and cathode layer 7(material be aluminium).
The concrete grammar that electroluminescent device makes is: spin coating hole injection layer 2(PEDOE:PSS successively in the conductive anode layer (ITO) of the substrate 1 through cleaning); Then stack gradually evaporation luminescent layer 3(P1:FIrpic on hole injection layer surface), hole blocking layer 4(BCP), electron transfer layer 5(Alq
3), electron injecting layer 6(LiF) and cathode layer 7(Al); Wherein, the thickness of each functional layer is respectively: the ITO layer (150nm) of substrate 1, hole injection layer 2 (30nm), luminescent layer 3 (20nm), hole blocking layer 4 (30nm), electron transfer layer 5(30nm), electron injecting layer 6 (1.5nm), cathode layer 7 (150nm).
The structure of this organic electroluminescence device can be expressed as: ITO/PEDOE:PSS/P1:FIrpic/BCP/Alq
3/ LiF/Al; Wherein, brace represents laminate structure.
Known to organic electroluminescence device current versus brightness-voltage characteristic test, the maximum current efficiency of this organic electroluminescence device is 6.4cd/A, and high-high brightness is 16970cd/m
2; Wherein, the test of current versus brightness-voltage characteristic is by with under Keithley source measuring system (Keithley2400Sourcemeter, Keithley2000Cuirrentmeter) of corrected silicon photoelectric diode, complete in atmosphere at room temperature.
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 Bipolar Polymer Blue-light emitting host material, is characterized in that, its structural formula is as follows:
In formula, R
1, R
2be C
1~ C
20alkyl, n is the integer of 10 ~ 100.
2. a preparation method for Bipolar Polymer Blue-light emitting host material as claimed in claim 1, is characterized in that, comprise the steps:
The compd A providing following structural formula to represent respectively and B,
Under oxygen-free environment, be after the organic solvent dissolution that is added into containing catalyzer and alkaline solution of the compd A of 1:1 ~ 1.2 and B by mol ratio, Suzuki coupling reaction is carried out 12 ~ 96 hours at 70 ~ 130 DEG C, stopped reaction cool to room temperature, separating-purifying reaction solution, obtains the described Bipolar Polymer Blue-light emitting host material that following structural formula represents:
Wherein, R
1, R
2be C
1~ C
20alkyl, n is the integer of 10 ~ 100.
3. the preparation method of Bipolar Polymer Blue-light emitting host material according to claim 2, it is characterized in that, described catalyzer is bis-triphenylphosphipalladium palladium dichloride or tetra-triphenylphosphine palladium, and the mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
4. the preparation method of Bipolar Polymer Blue-light emitting host material according to claim 2, it is characterized in that, described catalyzer is mol ratio is the organic palladium of 1:4 ~ 8 and the mixture of organophosphorus ligand, and the mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
5. the preparation method of Bipolar Polymer Blue-light emitting host material according to claim 4, 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 Bipolar Polymer Blue-light emitting host material 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, and in alkaline solution, the mol ratio of alkali solute and compd A is 20:1.
7., according to the preparation method of the arbitrary described Bipolar Polymer Blue-light emitting host material of claim 2 to 6, it is characterized in that, described organic solvent is selected from least one in toluene, DMF, tetrahydrofuran (THF).
8., according to the preparation method of the arbitrary described Bipolar Polymer Blue-light emitting host material of claim 2 to 6, it is characterized in that, the temperature of reaction of Suzuki coupling reaction is 90 ~ 120 DEG C, and the reaction times is 24 ~ 72 hours.
9. the preparation method of Bipolar Polymer Blue-light emitting host material according to claim 2, is characterized in that, separating-purifying reaction solution comprises:
After reaction stops, in reaction solution, add methyl alcohol carry out precipitating, then methyl alcohol and normal hexane extracting is used successively after the reaction solution after filtering precipitating by apparatus,Soxhlet's, then be solvent extracting again with chloroform, collect chloroformic solution and be spin-dried for, obtain red powder, the red powder after collection is 50 DEG C of dry 24h under vacuo, obtain described Bipolar Polymer Blue-light emitting host material.
10. the application of a Bipolar Polymer Blue-light emitting host material according to claim 1 in organic electroluminescence device luminescent layer.
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| CN113461914A (en) * | 2021-06-21 | 2021-10-01 | 上饶师范学院 | D-pi-A type polymer fluorescent material containing 2, 6-diphenyl-4-aryl pyridine structure and synthetic method thereof |
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| CN113461914A (en) * | 2021-06-21 | 2021-10-01 | 上饶师范学院 | D-pi-A type polymer fluorescent material containing 2, 6-diphenyl-4-aryl pyridine structure and synthetic method thereof |
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