CN103450879A - Copolymer blue light optical material, preparation method, and applications thereof - Google Patents
Copolymer blue light optical material, preparation method, and applications thereof Download PDFInfo
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- CN103450879A CN103450879A CN 201210171880 CN201210171880A CN103450879A CN 103450879 A CN103450879 A CN 103450879A CN 201210171880 CN201210171880 CN 201210171880 CN 201210171880 A CN201210171880 A CN 201210171880A CN 103450879 A CN103450879 A CN 103450879A
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Abstract
The invention belongs to the field of organic semiconductor materials, and discloses a copolymer blue light optical material, a preparation method, and applications thereof. The copolymer blue light optical material has a structure, which is represented in the description, wherein the R represents an alkyl with a carbon number of 1 to 20, and n is an integer in the range of 10 to 100. The copolymer blue light optical material comprises an anthrazole unit, which contains two nitrogen atoms and is an excellent electronic transportation unit. Polyfluorene is an important electroluminescent copolymer, alkyl modification can be carried out on the 9 position of polyfluorene, and thus the solubility property and film-forming property can be improved. Through introducing an anthrazole group into the main chain of polyfluorene, the shortages of polyfluorene are overcome, which is beneficial for improvement of efficiency of organic electroluminescent devices.
Description
Technical field
The present invention relates to the organic semiconductor material field, relate in particular to a kind of multipolymer blue light emitting material, its preparation method and application.
Background technology
Since Burroughes and Friend reported first polymer LED (PLEDs), in recent two decades in the past, PLED, aspect ultra-thin, the full-color and large-area flat-plate demonstration of preparation, having caused the research and development interest that people are strong, has obtained huge progress simultaneously.The solubility processibility of PLEDs, make people to carry out fabricate devices by reducing costs printing technology, and such as spray ink Printing and silk screen printing, than the small molecules Organic Light Emitting Diode of vacuum evaporation, it becomes original lower, commercially also more feasible.In order to realize flat pannel display and the solid-state illumination based on PLEDs, just need high performance red, green, blue luminescence polymer.Wherein the blue light polymkeric substance both can be used as luminescent layer, also can be used as the material of main part of luminous object, by energy, shifted or the mode of carrier capture obtains long wavelength's light.Most representative in existing polymkeric substance blue emitting material is poly-fluorenes, but because 9 easy oxidations of fluorenes form Fluorenone, make material easily form exciplex and the long wave emission when luminous, had a strong impact on the stability of the radiative saturated colour purity of device and glow color.Simultaneously, poly-fluorenes is because lower minimumly occupy molecular orbital(MO) (HOMO) energy level, and causes higher hole to inject obstacle, makes the luminous efficiency of device low.
Summary of the invention
One of problem to be solved by this invention is to provide a kind of multipolymer blue light emitting material of organic electroluminescence device luminous efficiency.
Technical scheme of the present invention is as follows:
A kind of multipolymer blue light emitting material, is characterized in that, it has following general structure:
In formula, R is C
1～C
20alkyl, the integer that n is 10-100.
Two of problem to be solved by this invention is to provide the preparation method of above-mentioned multipolymer blue light emitting material, comprises the steps:
In oxygen-free environment, by general structure, be
compd A and general structure be
the compd B ratio that is 1: 1～1.2 according to mol ratio add in the reactor containing the organic solvent of catalyzer and alkaline solution and carry out the Suzuki coupling reaction, this coupling reaction carries out under 70～130 ℃, and after coupling reaction 12～96h, be cooled to room temperature, stop coupling reaction, make the multipolymer blue light emitting material with following general structure:
Wherein, R is C
1～C
20alkyl, the integer that n is 10-100.
The preparation method of described multipolymer blue light emitting material, preferably, the Suzuki coupling reaction also comprises the purification step to the multipolymer blue light emitting material after finishing:
The Suzuki coupling reaction adds the methyl alcohol precipitating after finishing in reactor, after filtering by apparatus,Soxhlet's subsequently, then uses successively methyl alcohol and normal hexane extracting; Then take chloroform as solvent extraction to colourless, collect chloroformic solution and also be spin-dried for, obtain powder, and then will obtain powder and after 50 ℃ of dry 24h, obtain the multipolymer blue light emitting material of purifying under vacuum.
Above-mentioned catalyzer is bi triphenyl phosphine dichloride palladium or tetra-triphenylphosphine palladium, and the mol ratio of described catalyzer and compd A is 1: 20 ~ 1: 100; Perhaps
The mixture that described catalyzer is organic palladium and organophosphorus ligand, the mol ratio of organic palladium and organophosphorus ligand is 1: 4～8, and the mol ratio of described organic palladium and compd A is 1: 20 ~ 1: 100; Described organic palladium is palladium or three or two argon benzyl acetone two palladiums; Described organophosphorus ligand is tri-o-tolyl phosphine or 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl.
Above-mentioned 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 and compd A is 15: 1～40: 1;
Above-mentioned organic solvent is at least one in toluene, DMF and tetrahydrofuran (THF).
The preparation method of described multipolymer blue light emitting material, preferably, the temperature of reaction of described Suzuki coupling reaction is 90～120 ℃, the reaction times is 24～72h.
Above-mentioned multipolymer blue light emitting material, can be widely used in the luminescent layer of organic electroluminescence device, as the material of main part of luminescent layer.
Multipolymer blue light emitting material provided by the invention, the anthracene azoles of this material structure contains two nitrogen, it is a good electric transmission unit, poly-fluorenes is the important electroluminescent polymer of a class, alkyl modified can be carried out in the 9-position, thereby improves solubility property and the film forming properties of copolymerization fluorenes, by introduce the anthracene azoles on poly-fluorenes main chain, solve the shortcoming of poly-fluorenes, thereby be conducive to the raising of the efficiency of organic electroluminescence device.
Multipolymer blue light emitting material preparation method provided by the invention, adopted better simply synthetic route, thereby reduce technical process, and starting material are cheap and easy to get, makes manufacturing cost reduce; And the polymeric material novel structure made, solubility property is good, and film forming properties is good, applicable to organic electroluminescence device.
The accompanying drawing explanation
Fig. 1 is multipolymer blue light emitting material preparation technology schema of the present invention;
Fig. 2 is the organic electroluminescence device structural representation that embodiment 6 makes;
The electroluminescent spectrum figure that Fig. 3 is the organic electroluminescence device that makes of embodiment 6.
Embodiment
Multipolymer blue light emitting material provided by the invention, belong to electron-transporting type multipolymer blue light emitting material, and it has following general structure:
In formula, R is C
1～C
20alkyl, the integer that n is 10-100.
Multipolymer blue light emitting material provided by the invention, the anthracene azoles of this material structure contains two nitrogen, is a good electric transmission unit, and has rigidity and planarity preferably, and thermal stability is good; Poly-fluorenes is the important electroluminescent polymer of a class, alkyl modified can be carried out in the 9-position, thereby improves solubility property and the film forming properties of copolymerization fluorenes, by introduce the anthracene azoles on poly-fluorenes main chain, solve the shortcoming of poly-fluorenes, thereby be conducive to the raising of the efficiency of organic electroluminescence device.
In view of this, above-mentioned multipolymer blue light emitting material can also be widely used in the luminescent layer of organic electroluminescence device, as the material of main part of luminescent layer.
The present invention also provides the preparation technology of above-mentioned multipolymer blue light emitting material, as shown in Figure 1, comprises the steps:
S1, the compd A that following general structure is provided respectively and compd B:
Wherein, in compd A, R is C
1～C
20alkyl;
S2, under oxygen-free environment (at least one gas in nitrogen, argon gas forms), the ratio that is 1: 1～1.2 according to mol ratio by compd A and B be added into the organic solvent that contains catalyzer and alkaline solution reactor (as, flask or two-mouth bottle) in, carry out Suzuki coupling reaction 12～96h under 70～130 ℃, be cooled to subsequently room temperature, stop coupling reaction, obtain the reaction solution that contains the multipolymer blue light emitting material, this multipolymer blue light emitting material has following general structure:
In formula, the integer that n is 10-100;
After S3, reaction finish, in flask, add the methyl alcohol precipitating, by using successively methyl alcohol and normal hexane extracting after the apparatus,Soxhlet's filtering reacting liquid; Then take chloroform as solvent extraction to colourless, collect chloroformic solution and be spin-dried for and obtain powder, powder after 50 ℃ of dry 24h, is obtained to the multipolymer blue light emitting material of purifying under vacuum.
In the preparation method of above-mentioned multipolymer blue light emitting material, in step S2:
Catalyzer is bi triphenyl phosphine dichloride palladium or tetra-triphenylphosphine palladium, and the mol ratio of described catalyzer and compd A is 1: 20 ~ 1: 100; Perhaps
The mixture that described catalyzer is organic palladium and organophosphorus ligand, the mol ratio of organic palladium and organophosphorus ligand is 1: 4～8, and the mol ratio of described organic palladium and compd A is 1: 20 ~ 1: 100; Described organic palladium is palladium or three or two argon benzyl acetone two palladiums; Described organophosphorus ligand is tri-o-tolyl phosphine or 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl;
Above-mentioned 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 and compd A is 15: 1～40: 1;
Above-mentioned organic solvent is selected from least one in toluene, DMF and tetrahydrofuran (THF).
Preferably, in step S2, the temperature of reaction of Suzuki coupling reaction is 90～120 ℃, and the reaction times is 24～72h.
Multipolymer blue light emitting material preparation method provided by the invention, adopted better simply synthetic route, thereby reduce technical process, and starting material are cheap and easy to get, makes manufacturing cost reduce; And the polymeric material novel structure made, solubility property is good, and film forming properties is good, applicable to organic electroluminescence device.
Below in conjunction with accompanying drawing, preferred embodiment of the present invention is described in further detail.
In following embodiment 1 ~ 5, the monomer of compd A is bought and is obtained from the market, and the disclosed method of the monomer reference literature of compd B (J.AM.CHEM.SOC.9 VOL.125, NO.44,2003) is synthetic to be obtained.
Embodiment 1
The electron-transporting type multipolymer Blue-light emitting host material of the present embodiment, poly-{ 9,9-di-n-octyl-2,7-bis-base fluorenes-co-2,7-bis-bases-4,9-diphenylanthrancene azoles } (P1) (wherein, R is the octane base, and n=59), 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 9,9-di-n-octyl-2,7-bis-pinacol ester fluorenes (128mg, 0.2mmol), 2,7-bis-is bromo-4,9-diphenylanthrancene azoles (98mg, 0.2mmol) add in the flask that fills the 10ml toluene solvant, after fully dissolving, solution of potassium carbonate (2mL, 2mol/L) is joined in flask, vacuumize deoxygenation and be filled with argon gas, then add bi triphenyl phosphine dichloride palladium (5.6mg, 0.008mmol); Flask is heated to 100 ℃ and carries out Suzuki coupling reaction 48h.Subsequently, stop coupling reaction after cooling, to dripping in 50ml methyl alcohol and carry out sedimentation in flask; Use successively methyl alcohol and normal hexane extracting 24h after filtering by apparatus,Soxhlet's.Then take chloroform as solvent extraction to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, by after powder collection under vacuum 50 ℃ of dry 24h gathered { 9,9-di-n-octyl-2,7-bis-base fluorenes-co-2,7-bis-bases-4,9-diphenylanthrancene azoles } product, productive rate 86%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=42.0kDa, M
w/ M
n=2.3.
Embodiment 2:
The electron-transporting type multipolymer Blue-light emitting host material of the present embodiment, poly-{ 9,9-dimethyl-2,7-bis-base fluorenes-co-2,7-bis-bases-4,9-diphenylanthrancene azoles } (P2) (wherein, R is methyl, and n=42), its structural formula is as follows:
The preparation process of above-mentioned polymkeric substance is as follows:
Reaction formula is as follows:
Under nitrogen and the protection of argon gas gas mixture, by 9,9-dimethyl-2; 7-bis-pinacol ester fluorenes (134mg; 0.3mmol), 2,7-bis-is bromo-4,9-diphenylanthrancene azoles (147mg; 0.3mmol) and the 15mL tetrahydrofuran (THF) add in the two-mouth bottle of 50mL specification; after passing into the about 20min of gas mixture air-discharging of nitrogen and argon gas after fully dissolving, then tetra-triphenylphosphine palladium (4mg, 0.003mmol) is added wherein; add again sodium hydrogen carbonate solution (3mL, 2mol/L) after fully dissolving.After the about 10min of gas mixture air-discharging of fully logical nitrogen and argon gas, two-mouth bottle is joined to 70 ℃ and carry out Suzuki coupling reaction 96h again.Subsequently, stop coupling reaction after cooling, in two-mouth bottle, add 40mL methyl alcohol precipitating, after filtering by apparatus,Soxhlet's, use successively methyl alcohol and normal hexane extracting 24h.Then the chloroform of take is extremely colourless as solvent extraction, collects chloroformic solution and be spin-dried for to obtain red powder, will be gathered { 9,9-dimethyl-2,7-bis-base fluorenes-co-2,7-bis-bases-4,9-diphenylanthrancene azoles } product after powder collection after 50 ℃ of dry 24h under vacuum.Productive rate is 65%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=22.7kDa, M
w/ M
n=2.2.
Embodiment 3:
The electron-transporting type multipolymer Blue-light emitting host material of the present embodiment, poly-{ 9,9-, bis-NSC 62789 bases-2,7-bis-base fluorenes-co-2,7-bis-bases-4,9-diphenylanthrancene azoles } (P3) (wherein, R is the NSC 62789 base, and n=10), its structural formula is as follows:
The preparation process of above-mentioned polymkeric substance is as follows:
Reaction formula is as follows:
Under nitrogen protection, by 9,9-bis-NSC 62789 bases-2,7-bis-pinacol ester fluorenes (239mg, 0.3mmol), 2,7-bis-bromo-4,9-diphenylanthrancene azoles (162mg, 0.33mmol), palladium (3.5mg, 0.015mmol) and three (o-methoxyphenyl) phosphine (21mg, 0.06mmol) joins the N that fills 12mL, in the flask of dinethylformamide, add solution of potassium carbonate (3mL, 2mol/L) after fully dissolving, subsequently toward after leading to the about 30min of nitrogen purge gas in flask; Flask is heated to 130 ℃ and carries out Suzuki coupling reaction 12h.Subsequently, stop coupling reaction after cooling, in flask, add 40mL methyl alcohol precipitating, after filtering by apparatus,Soxhlet's, use successively methyl alcohol and normal hexane extracting 24h; Then take chloroform as solvent extraction to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, by after powder collection under vacuum after 50 ℃ of dry 24h, be poly-{ 9,9-, bis-NSC 62789 bases-2,7-bis-base fluorenes-co-2,7-bis-bases-4,9-diphenylanthrancene azoles } product, productive rate 85%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=11.7kDa, M
w/ M
n=2.4.
Embodiment 4:
The electron-transporting type multipolymer Blue-light emitting host material of the present embodiment, poly-{ 9,9-di-n-butyl-2,7-bis-base fluorenes-co-2,7-bis-bases-4,9-diphenylanthrancene azoles } (P4) (wherein, R is the normal butane base, and n=78), 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 9,9-di-n-butyl-2; 7-bis-pinacol ester fluorenes (159mg, 0.3mmol), 2,7-bis-bromo-4; 9-diphenylanthrancene azoles (176mg; 0.36mmol), three or two argon benzyl acetone two palladiums (9mg, 0.009mmol) and 2-dicyclohexyl phosphines-2 ', 6 '-dimethoxy-biphenyl (29mg; 0.072mmol) join the N that fills 12mL; in the flask of dinethylformamide, after fully dissolving, add sodium hydrogen carbonate solution (3mL, 2mol/L).Subsequently after the logical about 30min of nitrogen purge gas in flask; Flask is heated to 120 ℃ and carries out Suzuki coupling reaction 36h.Subsequently, stop coupling reaction after cooling, in flask, add 40mL methyl alcohol precipitating, after filtering by apparatus,Soxhlet's, use successively methyl alcohol and normal hexane extracting 24h; Then take chloroform as solvent extraction to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, by after powder collection under vacuum after 50 ℃ of dry 24h, be poly-{ 9,9-di-n-butyl-2,7-bis-base fluorenes-co-2,7-bis-bases-4,9-diphenylanthrancene azoles } product, productive rate is 70%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=48.6kDa, M
w/ M
n=2.3.
Embodiment 5:
The electron-transporting type multipolymer Blue-light emitting host material of the present embodiment, poly-{ 9,9-, bis-dodecyls-2,7-bis-base fluorenes-co-2,7-bis-bases-4,9-diphenylanthrancene azoles } (P5) (wherein, R is dodecyl, and n=100), its structural formula is as follows:
The preparation process of above-mentioned polymkeric substance is as follows:
Reaction formula is as follows:
Under nitrogen and the protection of argon gas gas mixture; by 9; 9-bis-dodecyls-2; 7-bis-pinacol ester fluorenes (226mg; 0.3mmol), 2; 6-bis-iodo-3; 7-phenylbenzene benzo [1,2-b:4,5-b '] two furans (147mg; 0.3mmol) and 15mL toluene add in the two-mouth bottle of 50mL specification; after passing into the about 20min of gas mixture air-discharging of nitrogen and argon gas after fully dissolving, then tetra-triphenylphosphine palladium (8mg, 0.006mmol) is added wherein; add again solution of potassium carbonate (3mL, 2mol/L).After the about 10min of gas mixture air-discharging of fully logical nitrogen and argon gas, two-mouth bottle is joined to 90 ℃ and carry out Suzuki coupling reaction 60h again.Subsequently, stop coupling reaction after cooling, in two-mouth bottle, add 40mL methyl alcohol precipitating, after filtering by apparatus,Soxhlet's, use successively methyl alcohol and normal hexane extracting 24h.Then the chloroform of take is extremely colourless as solvent extraction, collects chloroformic solution and be spin-dried for to obtain red powder, will be gathered { 9,9-, bis-dodecyls-2,7-bis-base fluorenes-co-2,7-bis-bases-4,9-diphenylanthrancene azoles } product after powder collection after 50 ℃ of dry 24h under vacuum.Productive rate is 78%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=83.5kDa, M
w/ M
n=2.4.
The present embodiment is organic electroluminescence device, the multipolymer blue light emitting material that the material of main part of its luminescent layer adopts embodiment 1 to make, i.e. poly-{ 9,9-di-n-octyl-2,7-bis-base fluorenes-co-2,7-bis-bases-4,9-diphenylanthrancene azoles } (P1), guest materials adopts two (4,6-difluorophenyl pyridine-N, C2) the pyridine formyl closes iridium (FIrpic), and guest materials is doped in material of main part according to the ratio of 15% mass percent, and manifestation is P1:FIrpic.
As shown in Figure 2, organic electroluminescence device comprises the ITO conductive glass that stacks gradually (being called for short ITO) 1, hole injection layer 2(PEDOE:PSS), hole transmission layer 3(N, N '-bis-[(1-naphthyl)-N, N '-phenylbenzene]-1,1 '-xenyl-4,4 '-diamines, NPD), luminescent layer 4(is usingd the polymkeric substance of the embodiment of the present invention 1 preparation as material of main part doping two (4,6-difluorophenyl pyridine-N, C2) the pyridine formyl closes iridium, FIrpic), cathode layer (comprising lithium fluoride layer 5 and aluminium lamination 6).
The concrete grammar that electroluminescent device is made is:
Spin coating PEDOT:PSS successively on conductive glass (ITO) substrate through cleaning, evaporation NPD, spin coating P1:FIrpic), evaporation lithium fluoride and aluminium are as cathode layer again, obtain organic electroluminescence device, the structure of this device and thickness are: ITO(150nm)/PEDOT:PSS (30nm)/NPD (40nm)/P1:FIrpic (20nm)/LiF (1.5nm)/Al (150nm)
The electroluminescent spectrum figure that Fig. 3 is the organic electroluminescence device that makes of embodiment 6; Wherein, electric current-the brightness-voltage characteristic of device is to be completed by the Keithley source measuring system with the correction silicon photoelectric diode (Keithley 2400 Sourcemeter, Keithley 2000 Cuirrentmeter), electroluminescent spectrum is by the French JY SPEX CCD3000 of company spectrometer measurement, and all measurements all complete in atmosphere at room temperature.Result shows, the maximum lumen efficiency of device is 20.0cd/A, and high-high brightness is 48610cd/m
2, the emission maximum peak value of this material is positioned at 472nm.
Should be understood that, the above-mentioned statement for preferred embodiment of the present invention is comparatively detailed, can not therefore think the restriction to scope of patent protection of the present invention, and scope of patent protection of the present invention should be as the criterion with claims.
Claims (10)
1. a multipolymer blue light emitting material, is characterized in that, it has following general structure:
In formula, R is C
1～C
20alkyl, the integer that n is 10-100.
2. the preparation method of a multipolymer blue light emitting material, is characterized in that, comprises the steps:
In oxygen-free environment, by general structure, be
compd A and general structure be
the compd B ratio that is 1: 1～1.2 according to mol ratio add in the reactor containing the organic solvent of catalyzer and alkaline solution and carry out the Suzuki coupling reaction, this coupling reaction carries out under 70～130 ℃, and after coupling reaction 12～96h, be cooled to room temperature, stop coupling reaction, make the multipolymer blue light emitting material with following general structure:
Wherein, R is C
1～C
20alkyl, the integer that n is 10-100.
3. the preparation method of multipolymer blue light emitting material according to claim 2, is characterized in that, the Suzuki coupling reaction also comprises the purification step to the multipolymer blue light emitting material after finishing:
The Suzuki coupling reaction adds the methyl alcohol precipitating after finishing in reactor, after filtering by apparatus,Soxhlet's subsequently, then uses successively methyl alcohol and normal hexane extracting; Then take chloroform as solvent extraction to colourless, collect chloroformic solution and also be spin-dried for, obtain powder, and then will obtain powder and after 50 ℃ of dry 24h, obtain the multipolymer blue light emitting material of purifying under vacuum.
4. according to the preparation method of the described multipolymer blue light emitting material of claim 2 or 3, it is characterized in that, described catalyzer is bi triphenyl phosphine dichloride palladium or tetra-triphenylphosphine palladium; The mol ratio of described catalyzer and compd A is 1: 20 ~ 1: 100.
5. according to the preparation method of the described multipolymer blue light emitting material of claim 2 or 3, it is characterized in that, the mixture that described catalyzer is organic palladium and organophosphorus ligand, and the mol ratio of organic palladium and organophosphorus ligand is 1: 4～8; The mol ratio of described organic palladium and compd A is 1: 20 ~ 1: 100.
6. the preparation method of multipolymer blue light emitting material according to claim 5, is characterized in that, described organic palladium is palladium or three or two argon benzyl acetone two palladiums; Described organophosphorus ligand is tri-o-tolyl phosphine or 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl.
7. according to the preparation method of the described multipolymer blue light emitting material of claim 2 or 3, it 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 and compd A is 15: 1～40: 1.
8. according to the preparation method of the described multipolymer blue light emitting material of claim 2 or 3, it is characterized in that, described organic solvent is at least one in toluene, DMF and tetrahydrofuran (THF).
9. according to the preparation method of the described multipolymer blue light emitting material of claim 2 or 3, it is characterized in that, the temperature of reaction of described Suzuki coupling reaction is 90～120 ℃, and the reaction times is 24～72h.
10. the described multipolymer blue light emitting material of claim 1 is as the application of the luminescent layer material of main part of organic electroluminescence device.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103804658A (en) * | 2014-01-20 | 2014-05-21 | 浙江大学 | Polymerizable polyfluorene macromonomer and synthesis method thereof |
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2012
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103804658A (en) * | 2014-01-20 | 2014-05-21 | 浙江大学 | Polymerizable polyfluorene macromonomer and synthesis method thereof |
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Application publication date: 20131218 |