CN103382246A - Fluorene/carbazole-based copolymer, preparation method thereof and polymer light emitting diode - Google Patents
Fluorene/carbazole-based copolymer, preparation method thereof and polymer light emitting diode Download PDFInfo
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- CN103382246A CN103382246A CN2012101372356A CN201210137235A CN103382246A CN 103382246 A CN103382246 A CN 103382246A CN 2012101372356 A CN2012101372356 A CN 2012101372356A CN 201210137235 A CN201210137235 A CN 201210137235A CN 103382246 A CN103382246 A CN 103382246A
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- MJIHYHLALYULFZ-UHFFFAOYSA-N Brc(cc1)cc(C(c2c3)(c(cc4)ccc4-[n]4c(cccc5)c5c5c4cccc5)c(cc4)ccc4-[n]4c5ccccc5c5c4cccc5)c1-c2ccc3Br Chemical compound Brc(cc1)cc(C(c2c3)(c(cc4)ccc4-[n]4c(cccc5)c5c5c4cccc5)c(cc4)ccc4-[n]4c5ccccc5c5c4cccc5)c1-c2ccc3Br MJIHYHLALYULFZ-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses a fluorene/carbazole-based copolymer, a preparation method thereof and a polymer light emitting diode, which belongs to the field of organic semiconductor materials. The fluorene/carbazole-based copolymer has a structural formula as described in the specification; in the formula, R is a C1-C20 alkyl group, and n is an integer in a range of 10 to 100. The fluorene/carbazole-based copolymer provided by the invention has the advantages of a novel structure, good dissolvability, excellent film forming performance, good heat stability, capacity of emitting blue light and applicability to an organic electrogenerated blue light device.
Description
Technical field
The present invention relates to the organic semiconductor material field, relate in particular to a kind of fluorenes/carbazyl multipolymer and preparation method thereof; The invention still further relates to a kind of this fluorenes/carbazyl multipolymer that uses as the polymer LED of luminescent layer material.
Background technology
Since Burroughes and Friend reported first polymer LED (PLEDs), in recent two decades in the past, PLED has obtained huge progress simultaneously having caused the research and development interest that people are strong aspect ultra-thin, the full-color and large-area flat-plate demonstration of preparation.The solubility processibility of PLEDs makes people to come 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, shifted or the mode of carrier capture obtains long wavelength's light by energy.Most representative in existing polymkeric substance blue emitting material is poly-fluorenes, but make material easily form exciplex and the long wave emission when luminous because 9 easy oxidations of fluorenes form Fluorenone, 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.
Summary of the invention
Based on the problems referred to above, the invention provides a kind of fluorenes/carbazyl multipolymer.
Technical scheme of the present invention is as follows:
A kind of fluorenes/carbazyl multipolymer has following structural formula:
In formula, R is C
1～C
20Alkyl, n is the integer of 10-100.
The present invention also provides the preparation method of above-mentioned fluorenes/carbazyl multipolymer, comprises that step is as follows:
S1, the compd A and the compd B that provide following structural formula to represent respectively,
A：
B：
Wherein, in compd B, R is C
1～C
20Alkyl;
S2, under oxygen-free environment, compd A and the compd B mol ratio according to 1:1 is added in the organic solvent that contains catalyzer and alkaline solution, carry out Suzuki coupling reaction 12～96h under 70～130 ° of C, stop the Suzuki coupling reaction after cooling, obtain containing the reaction solution of described fluorenes/carbazyl multipolymer, this fluorenes/carbazyl multipolymer has following structural formula:
In formula, n is the integer of 10-100.
In the preparation method's of above-mentioned fluorenes/carbazyl multipolymer step S2, described catalyzer is bi triphenyl phosphine dichloride palladium, tetra-triphenylphosphine palladium or three dibenzalacetone two palladiums/tri-butyl phosphine mixture, and the mol ratio of described catalyzer and compd A is 1:20 ~ 1:100; Described alkaline solution is solution of potassium carbonate, sodium carbonate solution or sodium hydrogen carbonate solution, and the mol ratio of the alkaloid substance in described alkaline solution and compd A is 1:50～1:20; Described organic solvent is at least a in toluene, DMF and tetrahydrofuran (THF).
As a kind of preferred version, in step S2, the temperature of Suzuki coupling reaction is 80 ~ 110 ℃, and the reaction times is 24 ~ 72h.
As another kind of preferred version, step S2 also comprises the purification process process to described fluorenes/carbazyl multipolymer after finishing:
S3, add the methyl alcohol precipitating in reaction solution, use successively methyl alcohol and normal hexane extracting after filtering by apparatus,Soxhlet's; Then take chloroform as solvent extraction to colourless, collect chloroformic solution and be spin-dried for and obtain shallow green powder; At last, with the dry 24h of shallow green powder 50 ° of C under vacuum, namely get the described fluorenes of purifying/carbazyl multipolymer.
The present invention also provides a kind of polymer LED, and its luminescent layer material adopts above-mentioned fluorenes/carbazyl multipolymer.
In the preparation method of above-mentioned fluorenes/carbazyl multipolymer, adopt better simply synthetic route, thereby reduce technical process, material is cheap and easy to get, reduces manufacturing cost.This material structure is novel, and solubility property is good, and film forming properties is good, Heat stability is good, and the emission blue light, this multipolymer is applicable to the blue organic electroluminescence device.
Description of drawings
Fig. 1 is preparation technology's schema of fluorenes of the present invention/carbazyl multipolymer;
Fig. 2 is the utilizing emitted light spectrogram of the fluorenes that makes of embodiment 1/carbazyl multipolymer.
Fig. 3 is the structural representation of the polymer LED that makes of embodiment 6.
Embodiment
A kind of fluorenes provided by the invention/carbazyl multipolymer has following structural formula:
In formula, R is C
1～C
20Alkyl, n is the integer of 10-100.
The preparation method of above-mentioned fluorenes/carbazyl multipolymer as shown in Figure 1, comprises that step is as follows:
S1, the compd A and the compd B that provide following structural formula to represent respectively,
A：
That is, 2,7-, two bromo-9,9 '-two (4-(9-carbazyl) phenyl) fluorenes;
B：
That is, 2,7-hypoboric acid pinacol ester-9,9-dialkyl group fluorenes;
Wherein, in compd B, R is C
1～C
20Alkyl;
S2, under oxygen-free environment, compd A and the compd B mol ratio according to 1:1 is added in the organic solvent that contains catalyzer and alkaline solution, carry out Suzuki coupling reaction 12～96h under 70～130 ° of C, stop the Suzuki coupling reaction after cooling, obtain containing the reaction solution of fluorenes/carbazyl multipolymer, this fluorenes/carbazyl multipolymer has following structural formula:
In formula, n is the integer of 10-100;
S3, add the methyl alcohol precipitating in reaction solution, use successively methyl alcohol and normal hexane extracting after filtering by apparatus,Soxhlet's; Then take chloroform as solvent extraction to colourless, collect chloroformic solution and be spin-dried for and obtain shallow green powder; At last, with the dry 24h of shallow green powder 50 ° of C under vacuum, namely get the fluorenes of purifying/carbazyl multipolymer; Wherein, methyl alcohol precipitating process need not to be limited to the consumption of methyl alcohol, as required, and preferred 40ml or 50ml.
In the preparation method's of above-mentioned fluorenes/carbazyl multipolymer step S2, described catalyzer is bi triphenyl phosphine dichloride palladium, tetra-triphenylphosphine palladium or three dibenzalacetone two palladiums/tri-butyl phosphine mixture, and the mol ratio of described catalyzer and compd A is 1:20 ~ 1:100; Described alkaline solution is solution of potassium carbonate, sodium carbonate solution or sodium hydrogen carbonate solution, and the mol ratio of the alkaloid substance in described alkaline solution and compd A is 1:50 ~ 1:20; Described organic solvent is at least a in toluene, DMF and tetrahydrofuran (THF).
In the preparation method of above-mentioned fluorenes/carbazyl multipolymer, the oxygen-free environment of Suzuki coupling reaction is by at least a gas composition in argon gas and nitrogen.
As a kind of preferred version, in step S2, the temperature of Suzuki coupling reaction is 80 ~ 110 ℃, and the reaction times is 24 ~ 72h.
A kind of polymer LED comprises the substrate of glass that stacks gradually, ito anode layer, the hole transmission layer of PEDOT-PSS material, the above-mentioned luminescent layer that fluorenes/carbazyl multipolymer is material, the electron injecting layer of LiF material and the cathode layer of aluminium material of making; It is substrate of glass/ITO layer/PEDOT-PSS layer/(fluorenes/carbazyl multipolymer) layer/LiF layer/aluminium lamination.
In the preparation method of above-mentioned fluorenes/carbazyl multipolymer, adopt better simply synthetic route, thereby reduce technical process, material is cheap and easy to get, reduces manufacturing cost.This material structure is novel, and solubility property is good, and film forming properties is good, Heat stability is good, and the emission blue light, this multipolymer is applicable to the blue organic electroluminescence device.
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 but the disclosed method of the monomer reference literature of compd A (Tetrahedron 63 (2007) 10161 – 10168) is synthetic, buy on the monomer market of compd B and obtain, Lumtec company produces, analytical pure.
Embodiment 1:
The fluorenes of the present embodiment/carbazyl multipolymer, namely gather 9,9 '-two (4-(9-carbazyl) phenyl) fluorenes-co-9,9 '-di-n-octyl fluorenes }, wherein, R is n-octyl, and n is 65, and 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, 2, 7-two bromo-9, 9 '-two (4-(9-carbazyl) phenyl) fluorenes (241mg, 0.3mmol), 2, 7-hypoboric acid pinacol ester-9, 9-dioctyl fluorene (193mg, 0.3mmol), three dibenzalacetone two palladium (13.75mg, 0.015mmol), tri-butyl phosphine (2mg, 0.01mmol), be dissolved in 12mL toluene, and then with solution of potassium carbonate (3mL, 2mol/L) join in mentioned solution, fully logical nitrogen purge gas is approximately after 30min, stir under 95 ℃, carry out Suzuki coupling reaction 48h, stop the Suzuki coupling reaction after cooling, obtain reaction solution.
Add 40mL methyl alcohol precipitating in reaction solution, 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 shallow green powder, be after 50 ℃ of dry 24h under vacuum after collecting poly-9,9 '-two (4-(9-carbazyl) phenyl) fluorenes-co-9,9 '-di-n-octyl fluorenes } product, productive rate is 60%.Test result is: Molecular weight (GPC, THF, R.I): M
n=67.2kDa, M
w/ M
n=2.3.
Fig. 2 is the fluorenes that makes of embodiment 1/carbazyl multipolymer, i.e. the utilizing emitted light spectrogram of poly-{ 9,9 '-two (4-(9-carbazyl) phenyl) fluorenes-co-9,9 '-di-n-octyl fluorenes }; X-coordinate is emission wavelength, and ordinate zou is luminous intensity intensity.
As can be seen from Figure 2, the maximum emission peak that embodiment 1 makes is poly-{ 9,9 '-two (4-(9-carbazyl) phenyl) fluorenes-co-9,9 '-di-n-octyl fluorenes } is positioned at the 463nm left and right, is blue light wavelength.
Embodiment 2:
The fluorenes of the present embodiment/carbazyl multipolymer, namely gather 9,9 '-two (4-(9-carbazyl) phenyl) fluorenes-co-9,9 '-two NSC 62789 base fluorenes }, wherein, R is the NSC 62789 base, and n is 45, and its structural formula is as follows: 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, add in the flask 2, 7-two bromo-9, 9 '-two (4-(9-carbazyl) phenyl) fluorenes (160mg, 0.2mmol), 2, 7-hypoboric acid pinacol ester-9, 9-two (eicosyl) fluorenes (196mg, 0.2mmol) and N, dinethylformamide solvent 15ml, and then with sodium carbonate solution (5mL, 2mol/L) join in solution, vacuumize deoxygenation and be filled with nitrogen, then add 5mg bi triphenyl phosphine dichloride palladium, be heated under 110 ℃ and stir, carry out Suzuki coupling reaction 24h, stop the Suzuki coupling reaction after cooling, obtain reaction solution.
Add 50ml methyl alcohol to carry out precipitating in reaction solution, 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 shallow green powder, extracting under vacuum pump, spend the night, gathered 9,9 '-two (4-(9-carbazyl) phenyl) fluorenes-co-9,9 '-two NSC 62789 base fluorenes } product, productive rate 75%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=61.7kDa, M
w/ M
n=2.2.
Embodiment 3:
The fluorenes of the present embodiment/carbazyl multipolymer, namely gather 9,9 '-two (4-(9-carbazyl) phenyl) fluorenes-co-9,9 '-dimethyl fluorene }, wherein, R is methyl, and n is 82, and its structural formula is as follows: 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, 2, 7-two bromo-9, 9 '-two (4-(9-carbazyl) phenyl) fluorenes (241mg, 0.3mmol), 2, 7-hypoboric acid pinacol ester-9, 9-dimethyl fluorene (134mg, 0.3mmol) and the 15mL tetrahydrofuran (THF) join respectively in the two-mouth bottle of 50mL, fully logical argon gas air-discharging is approximately after 20min, then the 17mg tetra-triphenylphosphine palladium is added wherein, and then with sodium hydrogen carbonate solution (4.5mL, 2mol/L) join in mentioned solution, fully logical nitrogen purge gas is approximately after 10min again, at 80 ℃ of stirring reaction 72h, stop the Suzuki coupling reaction after cooling, obtain reaction solution.
Add 40mL methyl alcohol precipitating in reaction solution, 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 the light green solid, gathered { 9 after 50 ℃ of dry 24h after collecting under vacuum, 9 '-two (4-(9-carbazyl) phenyl) fluorenes-co-9,9 '-dimethyl fluorene } product.Productive rate is 78%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=73.2kDa, M
w/ M
n=2.2.
Embodiment 4
The fluorenes of the present embodiment/carbazyl multipolymer, namely gather 9,9 '-two (4-(9-carbazyl) phenyl) fluorenes-co-9,9 '-two positive dodecyl fluorenes }, wherein, R is dodecyl, and n is 10, and its structural formula is as follows: its structural formula is as follows:
The preparation process of above-mentioned polymkeric substance is as follows:
Reaction formula is as follows:
With 2,7-hypoboric acid pinacol ester-9,9-two dodecyl fluorenes (151mg, 0.2mmol), 2,7-two bromo-9,9 '-two (4-(9-carbazyl) phenyl) fluorenes (160mg, 0.2mmol), add in the flask of the DMF solvent that fills 15ml, be dissolved into solution; And then sodium carbonate solution (4mL, 2mol/L) is joined in solution, the evacuated flask deoxygenation also is filled with argon gas, then add bi triphenyl phosphine dichloride palladium (0.01mmol, 7.02mg), be heated to 130 ℃ of reaction 12h, stop the Suzuki coupling reaction after cooling, obtain reaction solution.
Add 50mL methyl alcohol in flask, reaction solution is carried out precipitating, then filter by apparatus,Soxhlet's, afterwards successively with methyl alcohol and normal hexane extracting precipitation 24h; Then continue take chloroform colourless as solvent extraction is precipitated to, collect chloroformic solution and be spin-dried for and obtain shallow green powder, shallow green powder after collecting at last is poly-{ 9 after 50 ℃ of dry 24h under vacuum, 9 '-two (4-(9-carbazyl) phenyl) fluorenes-co-9,9 '-two positive dodecyl fluorenes } product, productive rate 58%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=11.5kDa, M
w/ M
n=2.4.
Embodiment 5
The fluorenes of the present embodiment/carbazyl multipolymer, namely gather 9,9 '-two (4-(9-carbazyl) phenyl) fluorenes-co-9,9 '-di-n-butyl fluorenes }, wherein, R is normal-butyl, and n is 100, and its structural formula is as follows: its structural formula is as follows:
The preparation process of above-mentioned polymkeric substance is as follows:
Reaction formula is as follows:
with 2, 7-hypoboric acid pinacol ester-9, 9-di-n-butyl fluorenes (159mg, 0.3mmol), 2, 7-two bromo-9, 9 '-two (4-(9-carbazyl) phenyl) fluorenes (241mg, 0.3mmol) add in the two-mouth bottle of the 50mL specification that fills the 15mL tetrahydrofuran (THF), be dissolved into solution, and then with sodium hydrogen carbonate solution (4.5mL, 2mol/L) join in solution, logical nitrogen and argon gas gas mixture, air-discharging is approximately after 20min, then with tetra-triphenylphosphine palladium (0.003mmol, 3.7mg) add in two-mouth bottle, fully lead to again nitrogen and argon gas gas mixture, continue air-discharging approximately after 10min, at 70 ℃ of stirring reaction 96h, stop the Suzuki coupling reaction after cooling, obtain reaction solution.
Add 40mL methyl alcohol in reaction solution, reaction solution is carried out precipitating process, then filter by apparatus,Soxhlet's, afterwards successively with methyl alcohol and normal hexane extracting precipitation 24h; Then continue take chloroform colourless as solvent extraction is precipitated to, collect chloroformic solution and be spin-dried for and obtain shallow green powder, shallow green powder after collecting at last is poly-{ 9 after 50 ℃ of dry 24h under vacuum, 9 '-two (4-(9-carbazyl) phenyl) fluorenes-co-9,9 '-di-n-butyl fluorenes } product, productive rate is 68%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=92.3kDa, M
w/ M
n=2.0.
Embodiment 6
The present embodiment is polymer LED, the fluorenes that its luminescent layer material employing embodiment 1 makes/carbazyl multipolymer, namely gather 9,9 '-two (4-(9-carbazyl) phenyl) fluorenes-co-9,9 '-di-n-octyl fluorenes }.
Polymer LED, as shown in Figure 3, the hole transmission layer 3, poly-{ 9 that comprises the substrate of glass 1 that stacks gradually, ITO conductive anode layer 2, PEDOT-PSS material, 9 '-two (4-(9-carbazyl) phenyl) fluorenes-co-9,9 '-di-n-octyl fluorenes } be the luminescent layer 4 of material, the electron injecting layer 5 of LiF material and the cathode layer 6 of aluminium material; Be substrate of glass 1/ITO layer 2/PEDOT-PSS layer 3/ poly-{ 9,9 '-two (4-(9-carbazyl) phenyl) fluorenes-co-9,9 '-di-n-octyl fluorenes } layer 4/LiF layer 5/ aluminium lamination 6.
The preparation process of this organic electroluminescence device is:
Tin indium oxide (ITO) surface deposition one deck square resistance of glass substrate is 10-20 Ω/mouth forms the conductive layer as anode;
Spin coating one deck PEDOT-PSS is as hole transmission layer on the ITO substrate, and then the spin coating embodiment of the present invention one poly-{ 9,9 '-two (4-(9-carbazyl) phenyl) fluorenes-co-9,9 '-di-n-octyl fluorenes } that make is as luminescent layer;
Vacuum evaporation LiF on luminescent layer is as buffer layer;
Vacuum evaporation metallic aluminium on described luminescent layer forms the metal aluminium lamination as negative electrode, obtains described organic electroluminescence device.The structure of device is: ITO(150nm)/PEDOT:PSS (30nm)/luminescent layer (20nm) //LiF (1.5nm)/Al (150nm)
Should be understood that, 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. fluorenes/carbazyl multipolymer is characterized in that having following structural formula:
In formula, R is C
1～C
20Alkyl, n is the integer of 10-100.
2. the preparation method of fluorenes/carbazyl multipolymer, is characterized in that, comprises the steps:
S1, the compd A and the compd B that provide following structural formula to represent respectively,
A：
B：
Wherein, in compd B, R is C
1～C
20Alkyl;
S2, under oxygen-free environment, compd A and the compd B mol ratio according to 1:1 is added in the organic solvent that contains catalyzer and alkaline solution, carry out Suzuki coupling reaction 12～96h under 70～130 ° of C, stop the Suzuki coupling reaction after cooling, obtain containing the reaction solution of described fluorenes/carbazyl multipolymer, this fluorenes/carbazyl multipolymer has following structural formula:
In formula, n is the integer of 10-100.
3. the preparation method of fluorenes according to claim 2/carbazyl multipolymer, is characterized in that, in step S2, described catalyzer is bi triphenyl phosphine dichloride palladium, tetra-triphenylphosphine palladium or three dibenzalacetone two palladiums/tri-butyl phosphine mixture.
4. the preparation method of according to claim 2 or 3 described fluorenes/carbazyl multipolymers, is characterized in that, in step S2, the mol ratio of described catalyzer and compd A is 1:20 ~ 1:100.
5. the preparation method of fluorenes according to claim 2/carbazyl multipolymer, is characterized in that, in step S2, described alkaline solution is solution of potassium carbonate, sodium carbonate solution or sodium hydrogen carbonate solution.
6. the preparation method of according to claim 2 or 5 described fluorenes/carbazyl multipolymers, is characterized in that, in step S2, the alkaloid substance in described alkaline solution and the mol ratio of compd A are 1:50～1:20.
7. the preparation method of fluorenes according to claim 2/carbazyl multipolymer, is characterized in that, in step S2, described organic solvent is at least a in toluene, DMF and tetrahydrofuran (THF).
8. the preparation method of fluorenes according to claim 2/carbazyl multipolymer, is characterized in that, in step S2, the temperature of Suzuki coupling reaction is 80 ~ 110 ℃, and the reaction times is 24 ~ 72h.
9. the preparation method of fluorenes according to claim 2/carbazyl multipolymer, is characterized in that, after finishing in step S2, also comprises the purification process process to described fluorenes/carbazyl multipolymer:
S3, add the methyl alcohol precipitating in reaction solution, use successively methyl alcohol and normal hexane extracting after filtering by apparatus,Soxhlet's; Then take chloroform as solvent extraction to colourless, collect chloroformic solution and be spin-dried for and obtain shallow green powder; At last, with the dry 24h of shallow green powder 50 ° of C under vacuum, namely get the described fluorenes of purifying/carbazyl multipolymer.
10. a polymer LED, is characterized in that, its luminescent layer material adopts fluorenes/carbazyl multipolymer, and this fluorenes/carbazyl multipolymer has following structural formula:
In formula, R is C
1～C
20Alkyl, n is the integer of 10-100.
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| CN108517030A (en) * | 2018-04-23 | 2018-09-11 | 南京邮电大学 | Fluorenyl nano grids polymer and its preparation method and application |
| CN110305299A (en) * | 2019-07-04 | 2019-10-08 | 南京邮电大学 | Cross-linked polymer and its preparation method and application based on copolymerization fluorenol |
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| CN110305299A (en) * | 2019-07-04 | 2019-10-08 | 南京邮电大学 | Cross-linked polymer and its preparation method and application based on copolymerization fluorenol |
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