CN104513375A - Polymer blue phosphorescence host material containing anthracene-azole and dibenzofuran units, preparation method and applications thereof - Google Patents
Polymer blue phosphorescence host material containing anthracene-azole and dibenzofuran units, preparation method and applications thereof Download PDFInfo
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- QQQTYMCRIPAMAL-UHFFFAOYSA-N BrC1=NC2=CC3=C(c4ccccc4)C(Br)=CCNC=C3C=C2C(c2ccccc2)=C1 Chemical compound BrC1=NC2=CC3=C(c4ccccc4)C(Br)=CCNC=C3C=C2C(c2ccccc2)=C1 QQQTYMCRIPAMAL-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention belongs to the field of organic electroluminescent materials, and discloses a polymer blue phosphorescence host material containing anthracene-azole and dibenzofuran units, a preparation method and applications thereof. The structural formula of the host material is represented in the description, and in the formula the n represents an integer in a range of 15 to 86. In the provided host material, the anthracene-azole unit contains two nitrogen atoms, is an excellent electron transmission unit, and moreover, has good rigidity, planarity, and thermal stability. The tetraphenyl silicon is a host material with an ultrahigh energy gap and has an extremely high triplet state energy level. Tetraphenyl-silicon-substituted dibenzofuran is introduced into the anthracene-azole main chain in order to solve the electro-inertia of tetraphenyl silicon, and thus the efficiency of organic electroluminescent devices is improved.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, particularly relate to a kind of polymkeric substance blue emitting phosphor material of main part containing anthracene azoles and diphenylene-oxide unit 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 the higher polymkeric substance blue emitting phosphor material of main part containing anthracene azoles and diphenylene-oxide unit preferably.
Technical scheme of the present invention is as follows:
The polymkeric substance blue emitting phosphor material of main part containing anthracene azoles and diphenylene-oxide unit provided by the invention, its structure is such as formula shown:
In formula, n is the integer of 15 ~ 86.
The present invention also provides a kind of preparation method containing the polymkeric substance blue emitting phosphor material of main part of anthracene azoles and diphenylene-oxide unit 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 polymkeric substance blue emitting phosphor material of main part containing anthracene azoles and diphenylene-oxide unit that following structural formula represents:
Wherein, n is the integer of 15 ~ 86.
In the preparation method of the described polymkeric substance blue emitting phosphor material of main part containing anthracene azoles and diphenylene-oxide unit, 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 the described polymkeric substance blue emitting phosphor material of main part containing anthracene azoles and diphenylene-oxide unit, 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 the described polymkeric substance blue emitting phosphor material of main part containing anthracene azoles and diphenylene-oxide unit, described organic solvent is selected from least one in toluene, DMF, tetrahydrofuran (THF).
In the preparation method of the described polymkeric substance blue emitting phosphor material of main part containing anthracene azoles and diphenylene-oxide unit, Suzuki coupling reaction, preferable reaction temperature is 90 ~ 120 DEG C, and the reaction times is 24 ~ 72 hours.
In the preparation method of the described polymkeric substance blue emitting phosphor material of main part containing anthracene azoles and diphenylene-oxide unit, oxygen-free environments of one or both compositions in described oxygen-free environment preferred nitrogen, argon gas.
In the preparation method of the described polymkeric substance blue emitting phosphor material of main part containing anthracene azoles and diphenylene-oxide unit, 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 the described polymkeric substance blue emitting phosphor material of main part containing anthracene azoles and diphenylene-oxide unit.
The present invention also provides the above-mentioned application of polymkeric substance blue emitting phosphor material of main part in organic electroluminescence device luminescent layer containing anthracene azoles and diphenylene-oxide unit.
Of the present invention containing in the polymkeric substance blue emitting phosphor material of main part of anthracene azoles and diphenylene-oxide unit, anthracene azoles contains two nitrogen-atoms, and be an excellent electric transmission unit, and have good rigidity and planarity, thermal stability is good; Tetraphenyl-silicon is superelevation energy gap material of main part, has very high triplet; By introducing tetraphenyl-silicon for diphenylene-oxide on anthracene azoles main chain, solving the shortcoming of tetraphenyl-silicon electricity inertia, thus being conducive to the raising of the efficiency of organic electroluminescence device.
The above-mentioned preparation method containing the polymkeric substance blue emitting phosphor material of main part of anthracene azoles and diphenylene-oxide unit, 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 containing the polymkeric substance blue emitting phosphor material of main part of anthracene azoles and diphenylene-oxide unit 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 all purchased from scientific and technological in lark prestige.
Embodiment 1: the polymkeric substance blue emitting phosphor material of main part containing anthracene azoles and diphenylene-oxide unit of the present embodiment, namely { 2 are gathered, 7-bis-base-4,9-diphenylanthrancene azoles-co-3,7-bis-bases-dibenzo [b, d] furans-2,8-bis-(tri-phenyl-silane) } (P1) (wherein, n=38), 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 2,7-bis-bromo-4,9-diphenylanthrancene azoles (98mg, 0.2mmol), 3,7-bis-tetramethyl ethylene ketone boric acid ester dibenzo [b, d] furans-2,8-bis-(tri-phenyl-silane) (187mg, 0.2mmol) adds 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 product P 1 under vacuo, productive rate 71%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=51.7kDa, M
w/ M
n=2.2.
Fig. 1 is the thermogravimetic analysis (TGA) figure containing the polymkeric substance blue emitting phosphor material of main part of anthracene azoles and diphenylene-oxide unit 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, containing the thermal weight loss temperature (T of the polymkeric substance blue emitting phosphor material of main part 5% of anthracene azoles and diphenylene-oxide unit
d) be 434 DEG C.
Embodiment 2: the polymkeric substance blue emitting phosphor material of main part containing anthracene azoles and diphenylene-oxide unit of the present embodiment, namely { 2 are gathered, 7-bis-base-4,9-diphenylanthrancene azoles-co-2,7-bis-base-9-(4-(diphenyl phosphine oxygen base) phenyl)-9H-carbazole } (P2) (wherein, n=23), 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; 7-bis-bromo-4; 9-diphenylanthrancene azoles (147mg; 0.3mmol), 3; 7-bis-tetramethyl ethylene ketone boric acid ester dibenzo [b; d] furans-2; 8-bis-(tri-phenyl-silane) (281mg, 0.3mmol) and 15mL tetrahydrofuran (THF) add in the two-mouth bottle of 50mL specification, after the gas mixture air-discharging passing into nitrogen and argon gas after fully dissolving is about 20min; then by tetra-triphenylphosphine palladium (4mg; 0.003mmol) add wherein, after fully dissolving, add sodium bicarbonate (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 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 74%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=38.2kDa, M
w/ M
n=2.3.
Embodiment 3: the polymkeric substance blue emitting phosphor material of main part containing anthracene azoles and diphenylene-oxide unit of the present embodiment, namely { 2 are gathered, 7-bis-base-4,9-diphenylanthrancene azoles-co-2,7-bis-base-9-(4-(diphenyl phosphine oxygen base) phenyl)-9H-carbazole } (P3) (wherein, n=86), 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 2,7-bis-bromo-4,9-diphenylanthrancene azoles (147mg, 0.3mmol), 3,7-bis-tetramethyl ethylene ketone boric acid ester dibenzo [b, d] furans-2,8-bis-(tri-phenyl-silane) (309mg, 0.33mmol), palladium (3.5mg, 0.015mmol) He three (o-methyl-phenyl-) phosphine (21mg, 0.06mmol) join in the flask of the DMF filling 12mL, after fully dissolving, add salt of wormwood (3mL, 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 product P 3, productive rate 75%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=84.3kDa, M
w/ M
n=2.0.Embodiment 4: the polymkeric substance blue emitting phosphor material of main part containing anthracene azoles and diphenylene-oxide unit of the present embodiment, namely { 2 are gathered, 7-bis-base-4,9-diphenylanthrancene azoles-co-2,7-bis-base-9-(4-(diphenyl phosphine oxygen base) phenyl)-9H-carbazole } (P4) (wherein, n=15), 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; 7-bis-bromo-4; 9-diphenylanthrancene azoles (147mg; 0.3mmol), 3; 7-bis-tetramethyl ethylene ketone boric acid ester dibenzo [b; d] furans-2,8-bis-(tri-phenyl-silane) (337mg, 0.36mmol), three or two argon benzyl acetone two palladium (9mg; 0.009mmol) with 2-dicyclohexyl phosphine-2 '; 6 '-dimethoxy-biphenyl (29mg, 0.072mmol) joins in the flask of the DMF filling 12mL; sodium bicarbonate (3mL, 2mol/L) solution is added after abundant dissolving.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 68%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=12.9kDa, M
w/ M
n=2.4.
Embodiment 5:
The polymkeric substance blue emitting phosphor material of main part containing anthracene azoles and diphenylene-oxide unit of the present embodiment, namely { 2 are gathered, 7-bis-base-4,9-diphenylanthrancene azoles-co-2,7-bis-base-9-(4-(diphenyl phosphine oxygen base) phenyl)-9H-carbazole } (P5) (wherein, n=51), 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; 7-bis-bromo-4; 9-diphenylanthrancene azoles (147mg; 0.3mmol), 3; 7-bis-tetramethyl ethylene ketone boric acid ester dibenzo [b; d] furans-2; 8-bis-(tri-phenyl-silane) (337mg, 0.36mmol) and 15mL toluene add in the two-mouth bottle of 50mL specification, after the gas mixture air-discharging passing into nitrogen and argon gas after fully dissolving is about 20min; then by tetra-triphenylphosphine palladium (8mg; 0.006mmol) add wherein, then add salt of wormwood (3mL, 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 74%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=41.2kDa, M
w/ M
n=2.2.
Embodiment 6:
Originally organic electroluminescence device is embodied as, its polymkeric substance blue emitting phosphor material of main part containing anthracene azoles and diphenylene-oxide unit obtained with the present invention, what preferred embodiment 1 was obtained gathers { 2,7-bis-base-4,9-diphenylanthrancene azoles-co-3,7-bis-bases-dibenzo [b, d] furans-2,8-bis-(tri-phenyl-silane) } as the material of main part of luminescent layer, the polymkeric substance blue emitting phosphor material of main part containing anthracene azoles and diphenylene-oxide unit 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), hole transmission layer 3(material is N, N '-two [(1-naphthyl)-N, N '-phenylbenzene]-1, 1 '-xenyl-4, 4 '-diamines (NPD)), luminescent layer 4(material is poly-{ 2, 7-bis-base-4, 9-diphenylanthrancene azoles-co-3, 7-bis-bases-dibenzo [b, d] furans-2, 8-bis-(tri-phenyl-silane) } (representing with P1) as two (4 of material of main part doping 20wt%, 6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic closes the mixing material that iridium (III) (FIrpic) forms, be expressed as P1:FIrpic), electron injecting layer 5(material is lithium fluoride) and cathode layer 6(material be aluminium).
The concrete grammar that organic electroluminescence 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 hole transmission layer 3(NPD on hole injection layer surface), luminescent layer 4(P1:FIrpic), electron injecting layer 5(LiF) and cathode layer 6(Al); Wherein, the thickness of each functional layer is respectively: the ITO layer (150nm) of substrate 1, hole injection layer 2 (30nm), hole transmission layer 3(40nm), luminescent layer 4 (20nm), electron injecting layer 5 (1.5nm), cathode layer 6 (150nm).
The structure of this organic electroluminescence device can be expressed as: ITO/PEDOE:PSS/NPD/P1:FIrpic/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 6.3cd/A, and high-high brightness is 16430cd/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. contain a polymkeric substance blue emitting phosphor material of main part for anthracene azoles and diphenylene-oxide unit, it is characterized in that, its structural formula is as follows:
In formula, n is the integer of 15 ~ 86.
2. the preparation method containing the polymkeric substance blue emitting phosphor material of main part of anthracene azoles and diphenylene-oxide unit 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 polymkeric substance blue emitting phosphor material of main part containing anthracene azoles and diphenylene-oxide unit that following structural formula represents:
Wherein, n is the integer of 15 ~ 86.
3. the preparation method containing the polymkeric substance blue emitting phosphor material of main part of anthracene azoles and diphenylene-oxide unit 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 containing the polymkeric substance blue emitting phosphor material of main part of anthracene azoles and diphenylene-oxide unit 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 containing the polymkeric substance blue emitting phosphor material of main part of anthracene azoles and diphenylene-oxide unit 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 containing the polymkeric substance blue emitting phosphor material of main part of anthracene azoles and diphenylene-oxide unit 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 arbitrary described preparation method containing the polymkeric substance blue emitting phosphor material of main part of anthracene azoles and diphenylene-oxide unit 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 arbitrary described preparation method containing the polymkeric substance blue emitting phosphor material of main part of anthracene azoles and diphenylene-oxide unit 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 containing the polymkeric substance blue emitting phosphor material of main part of anthracene azoles and diphenylene-oxide unit according to claim 2, it 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 the described polymkeric substance blue emitting phosphor material of main part containing anthracene azoles and diphenylene-oxide unit.
10. the application of polymkeric substance blue emitting phosphor material of main part in organic electroluminescence device luminescent layer containing anthracene azoles and diphenylene-oxide unit according to claim 1.
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