CN103382246B - Fluorenes/carbazyl copolymer, its preparation method and polymer LED - Google Patents
Fluorenes/carbazyl copolymer, its preparation method and polymer LED Download PDFInfo
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Abstract
The invention belongs to organic semiconductor material field, it discloses a kind of fluorenes/carbazyl copolymer, its preparation method and polymer LED；This fluorenes/carbazyl copolymer has a following structural formula:In formula, R is C1～C20Alkyl, n is the integer of 10 100.Fluorenes/carbazyl copolymer that the present invention provides, novel structure, solubility property is good, and filming performance is excellent, Heat stability is good, launches blue light, is applicable to blue organic light-emitting devices.
Description
Technical field
The present invention relates to organic semiconductor material field, particularly relate to a kind of fluorenes/carbazyl copolymer and preparation thereof
Method；The invention still further relates to a kind of use this fluorenes/carbazyl copolymer as the polymer light-emitting of emitting layer material
Diode.
Background technology
Since Burroughes and Friend reported first polymer LED (PLEDs),
In the recent two decades in past, PLED causes people in terms of preparing ultra-thin, full-color and large-area flat-plate display
Strong research and development interest, achieves huge progress simultaneously.The solubility processability of PLEDs, makes
Obtain people and can prepare device by reducing cost printing techniques, such as inkjet printing and silk screen printing, phase
Than in the little molecule Organic Light Emitting Diode of vacuum evaporation, it becomes original lower, the most feasible.
In order to realize flat pannel display based on PLEDs and solid-state illumination, it is necessary to high performance red, green, blue
Light emitting polymer.Wherein blue light frequency-doubling both can be as luminescent layer, it is also possible to as the main body of light-emitting guest
Material, is shifted by energy or obtains the light of long wavelength by the way of carrier capture.Existing polymer is blue
Most representative in color luminescent material is polyfluorene, but because 9 oxidizable formation Fluorenones of fluorenes make material
Easily form exciplex when luminescence and longwave transmissions, had a strong impact on device and launched the saturated colour purity of light
Degree and the stability of glow color.Meanwhile, polyfluorene is because relatively low minimum occupying molecular orbit (HOMO)
Energy level, and cause higher hole to inject obstacle.
Summary of the invention
Based on the problems referred to above, the present invention provides a kind of fluorenes/carbazyl copolymer.
Technical scheme is as follows:
A kind of fluorenes/carbazyl copolymer, has a following structural formula:
In formula, R is C1～C20Alkyl, n is the integer of 10-100.
The present invention also provides for the preparation method of above-mentioned fluorenes/carbazyl copolymer, comprises the following steps that
S1, provide compound A and the compound B that following structural formula represents respectively,
A:
B:
Wherein, compound B
In, R is C1～C20Alkyl；
S2, under oxygen-free environment, by compound A and compound B according to the mol ratio of 1:1 be added into containing
In the organic solvent of catalyst and aqueous slkali, under 70～130 ° of C, carry out Suzuki coupled reaction 12～96h,
Stop Suzuki coupled reaction after cooling, obtain the reactant liquor containing described fluorenes/carbazyl copolymer, this fluorenes/carbazole
Base co-polymer has a following structural formula:
In formula, n is the integer of 10-100.
In step S2 of the preparation method of above-mentioned fluorenes/carbazyl copolymer, described catalyst is bi triphenyl phosphine two
Palladous chloride., tetra-triphenylphosphine palladium or three dibenzalacetone two palladiums/tri-butyl phosphine mixture, and described in urge
Agent is 1:20 ~ 1:100 with the mol ratio of compound A；Described aqueous slkali is that solution of potassium carbonate, sodium carbonate are molten
The mol ratio of the alkaloid substance in liquid or sodium bicarbonate solution, and described aqueous slkali and compound A be 1:50～
1:20；Described organic solvent is at least one in toluene, N,N-dimethylformamide and oxolane.
As a kind of preferred version, in step S2, the temperature of Suzuki coupled reaction is 80 ~ 110 DEG C, reaction
Time is 24 ~ 72h.
As another kind of preferred version, after step S2 terminates, also include described fluorenes/carbazyl copolymer is pure
Change processing procedure:
S3, in reactant liquor, add methanol precipitating, successively with methanol and just after being filtered by apparatus,Soxhlet's
Hexane extraction；Then with chloroform for solvent extraction to colourless, collect chloroformic solution and be spin-dried for obtaining light green toner
End；Finally, shallow green powder 50 ° of C under vacuo being dried 24h, the described fluorenes/carbazyl obtaining purification is common
Polymers.
The present invention also provides for a kind of polymer LED, and its emitting layer material uses above-mentioned fluorenes/carbazyl common
Polymers.
In the preparation method of above-mentioned fluorenes/carbazyl copolymer, use better simply synthetic route, thus reduce
Technological process, material is cheap and easy to get, reduces manufacturing cost.This material structure is novel, and solubility property is good,
Filming performance is excellent, Heat stability is good, launches blue light, and this copolymer is applicable to blue organic light-emitting devices.
Accompanying drawing explanation
Fig. 1 is the preparation technology flow chart of fluorenes of the present invention/carbazyl copolymer；
Fig. 2 is the emission spectrum figure of fluorenes/carbazyl copolymer that embodiment 1 prepares.
Fig. 3 is the structural representation of the polymer LED that embodiment 6 prepares.
Detailed description of the invention
A kind of fluorenes/carbazyl copolymer that the present invention provides, has a following structural formula:
In formula, R is C1～C20Alkyl, n is the integer of 10-100.
The preparation method of above-mentioned fluorenes/carbazyl copolymer, as it is shown in figure 1, comprise the following steps that
S1, provide compound A and the compound B that following structural formula represents respectively,
A:
That is, 2,7-bis-bromo-9,9 '-two (4-(9-carbazyl) phenyl) fluorenes；
B:
That is, 2,7-hypoboric acid pinacol ester-9,9-dialkyl fluorene；
Wherein, in compound B, R is C1～C20Alkyl；
S2, under oxygen-free environment, by compound A and compound B according to the mol ratio of 1:1 be added into containing
In the organic solvent of catalyst and aqueous slkali, under 70～130 ° of C, carry out Suzuki coupled reaction 12～96h,
Stopping Suzuki coupled reaction after cooling, obtain the reactant liquor containing fluorenes/carbazyl copolymer, this fluorenes/carbazyl is common
Polymers has a following structural formula:
In formula, n is the integer of 10-100；
S3, in reactant liquor, add methanol precipitating, successively with methanol and just after being filtered by apparatus,Soxhlet's
Hexane extraction；Then with chloroform for solvent extraction to colourless, collect chloroformic solution and be spin-dried for obtaining light green toner
End；Finally, shallow green powder 50 ° of C under vacuo are dried 24h, obtain the fluorenes/carbazyl copolymer of purification；
Wherein, methanol precipitation process, to the consumption of methanol without being any limitation as, as required, preferably 40ml or 50ml.
In step S2 of the preparation method of above-mentioned fluorenes/carbazyl copolymer, described catalyst is bi triphenyl phosphine two
Palladous chloride., tetra-triphenylphosphine palladium or three dibenzalacetone two palladiums/tri-butyl phosphine mixture, and described in urge
Agent is 1:20 ~ 1:100 with the mol ratio of compound A；Described aqueous slkali is that solution of potassium carbonate, sodium carbonate are molten
Alkaloid substance in liquid or sodium bicarbonate solution, and described aqueous slkali is 1:50 ~ 1:20 with the mol ratio of compound A；
Described organic solvent is at least one in toluene, N,N-dimethylformamide and oxolane.
In the preparation method of above-mentioned fluorenes/carbazyl copolymer, the oxygen-free environment of Suzuki coupled reaction by argon and
At least one gas composition in nitrogen.
As a kind of preferred version, in step S2, the temperature of Suzuki coupled reaction is 80 ~ 110 DEG C, reaction
Time is 24 ~ 72h.
A kind of polymer LED, including the substrate of glass stacked gradually, ito anode layer,
The hole transmission layer of PEDOT-PSS material, above-mentioned prepared fluorenes/carbazyl copolymer are the luminescent layer of material, LiF
The electron injecting layer of material and the cathode layer of aluminium material；I.e. substrate of glass/ITO layer/PEDOT-PSS layer/
(fluorenes/carbazyl copolymer) layer/LiF layer/aluminium lamination.
In the preparation method of above-mentioned fluorenes/carbazyl copolymer, use better simply synthetic route, thus reduce
Technological process, material is cheap and easy to get, reduces manufacturing cost.This material structure is novel, and solubility property is good,
Filming performance is excellent, Heat stability is good, launches blue light, and this copolymer is applicable to blue organic light-emitting devices.
Further illustrate the technology case of the present invention below by concrete example and legend, specifically include material
Prepared by preparation and device, but these embodiments are not limiting as the present invention, and wherein the monomer of compound A can be joined
Synthesize according to method disclosed in document (Tetrahedron 63 (2007) 10,161 10168), the list of compound B
Body is commercially available on market, and Lumtec company produces, analytical pure.
Embodiment 1:
The fluorenes of the present embodiment/carbazyl copolymer, the most poly-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 polymer is as follows:
Reaction equation is as follows:
Under nitrogen protection, 2,7-bis-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 palladiums
(13.75mg, 0.015mmol), tri-butyl phosphine (2mg, 0.01mmol), it is dissolved in 12mL toluene,
The most again solution of potassium carbonate (3mL, 2mol/L) is joined in above-mentioned solution, the most logical nitrogen purge gas about 30
After min, stir at 95 DEG C, carry out Suzuki coupled reaction 48h, after cooling, stop Suzuki coupling
Reaction, it is thus achieved that reactant liquor.
In reactant liquor, add 40mL methanol precipitating, after being filtered by apparatus,Soxhlet's successively with methanol and
Normal hexane extracting 24h.Then with chloroform for solvent extraction to the most colourless, collect chloroformic solution being spin-dried for and obtain shallow
Green powder, is poly-{ 9,9 '-two (4-(9-carbazyl) benzene after 50 DEG C of dry 24h after collection under vacuo
Base) fluorenes-co-9,9 '-di-n-octyl fluorenes } product, productivity is 60%.Test result is: Molecular weight
(GPC,THF,R.I):Mn=67.2kDa,Mw/Mn=2.3。
Fig. 2 is fluorenes/carbazyl copolymer that embodiment 1 prepares, the most poly-{ 9,9 '-two (4-(9-carbazyl) benzene
Base) fluorenes-co-9,9 '-di-n-octyl fluorenes emission spectrum figure；Abscissa is for launching wavelength, and vertical coordinate is luminous
Strength.
From figure 2 it can be seen that embodiment 1 prepare poly-9,9 '-two (4-(9-carbazyl) phenyl) fluorenes
-co-9,9 '-di-n-octyl fluorenes } maximum emission peak be positioned at about 463nm, for blue light wavelength.
Embodiment 2:
The fluorenes of the present embodiment/carbazyl copolymer, the most poly-9,9 '-two (4-(9-carbazyl) phenyl) fluorenes-co-9,9 '-
Two AI3-28404 base fluorenes }, wherein, R is AI3-28404 base, and n is 45, and its structural formula is as follows: its structural formula
As follows:
The preparation process of above-mentioned polymer is as follows:
Reaction equation is as follows:
Under nitrogen protection, add in flask 2,7-bis-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)
With DMF solvent 15ml, the most again sodium carbonate liquor (5mL, 2mol/L) is joined solution
In, evacuation deoxygenation is also filled with nitrogen, is subsequently adding 5mg bis-triphenylphosphipalladium palladium dichloride, is heated to 110 DEG C
Lower stirring, carry out Suzuki coupled reaction 24h, stop Suzuki coupled reaction after cooling, it is thus achieved that reactant liquor.
In reactant liquor, add 50ml methanol carry out precipitating, after being filtered by apparatus,Soxhlet's, use methanol successively
24h is extracted with normal hexane.Then with chloroform for solvent extraction to colourless, collect chloroformic solution and be spin-dried for obtaining
Shallow green powder, under vacuum pump extract, overnight, obtain poly-9,9 '-two (4-(9-carbazyl) phenyl) fluorenes
-co-9,9 '-two AI3-28404 base fluorenes } product, productivity 75%.
Test result is: Molecular weight (GPC, THF, R.I): Mn=61.7kDa,Mw/Mn=2.2。
Embodiment 3:
The fluorenes of the present embodiment/carbazyl copolymer, the most poly-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 polymer is as follows:
Reaction equation is as follows:
Under argon shield, 2,7-bis-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 15mL oxolane are respectively
Join in the two-mouth bottle of 50mL, after the most logical argon air-discharging about 20min, then by 17mg tetra-or three
Phenylphosphine palladium is added thereto, and joins in above-mentioned solution by sodium bicarbonate solution (4.5mL, 2mol/L) the most again,
After the most fully leading to nitrogen purge gas about 10min, at 80 DEG C of stirring reaction 72h, after cooling, stop Suzuki
Coupled reaction, it is thus achieved that reactant liquor.
40mL methanol precipitating is added, successively with methanol and just after being filtered by apparatus,Soxhlet's in reactant liquor
Hexane extraction 24h, then with chloroform for solvent extraction to the most colourless, collects chloroformic solution being spin-dried for and obtains light green
Color solid, obtain after 50 DEG C of dry 24h under vacuo after collection poly-9,9 '-two (4-(9-carbazyl) phenyl)
Fluorenes-co-9,9 '-dimethyl fluorene } product.Productivity is 78%.
Test result is: Molecular weight (GPC, THF, R.I): Mn=73.2kDa,Mw/Mn=2.2。
Embodiment 4
The fluorenes of the present embodiment/carbazyl copolymer, the most poly-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 such as
Under:
The preparation process of above-mentioned polymer is as follows:
Reaction equation is as follows:
By 2,7-hypoboric acid pinacol ester-9,9-two dodecyl fluorenes (151mg, 0.2mmol), 2,7-dibromo
-9,9 '-two (4-(9-carbazyl) phenyl) fluorenes (160mg, 0.2mmol), add the N, N-filling 15ml
In the flask of solvent dimethylformamide, it is dissolved into solution；The most again by sodium carbonate liquor (4mL, 2mol/L)
Joining in solution, evacuated flask deoxygenation is also filled with argon, is subsequently adding bis-triphenylphosphipalladium palladium dichloride (0.01
Mmol, 7.02mg), it is heated to 130 DEG C of reaction 12h, stops Suzuki coupled reaction after cooling, it is thus achieved that anti-
Answer liquid.
In flask, add 50mL methanol, reactant liquor carried out precipitating, then pass through apparatus,Soxhlet's and filter,
The most successively with methanol and normal hexane extracting precipitation 24h；Then proceed to be precipitated to nothing with chloroform for solvent extraction
Color, collects chloroformic solution and is spin-dried for obtaining shallow green powder, and the shallow green powder after finally collecting is in vacuum
Be after lower 50 DEG C of dry 24h poly-9,9 '-two (4-(9-carbazyl) phenyl) fluorenes-co-9,9 '-two positive 12
Base fluorenes } product, productivity 58%.
Test result is: Molecular weight (GPC, THF, R.I): Mn=11.5kDa,Mw/Mn=2.4。
Embodiment 5
The fluorenes of the present embodiment/carbazyl copolymer, the most poly-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 polymer is as follows:
Reaction equation is as follows:
By 2,7-hypoboric acid pinacol ester-9,9-di-n-butyl fluorenes (159mg, 0.3mmol), 2,7-bis-bromo-9,9 '-
Two (4-(9-carbazyl) phenyl) fluorenes (241mg, 0.3mmol) adds and fills the 50mL of 15mL oxolane
In the two-mouth bottle of specification, it is dissolved into solution, the most again sodium bicarbonate solution (4.5mL, 2mol/L) is joined
In solution, logical nitrogen and argon gaseous mixture, after air-discharging about 20min, then by tetra-triphenylphosphine palladium (0.003
Mmol, 3.7mg) add in two-mouth bottle, more fully lead to nitrogen and argon gaseous mixture, continue air-discharging about 10min
After, at 70 DEG C of stirring reaction 96h, stop Suzuki coupled reaction after cooling, it is thus achieved that reactant liquor.
In reactant liquor, add 40mL methanol, reactant liquor is carried out precipitating process, then passes through apparatus,Soxhlet's
Filter, the most successively with methanol and normal hexane extracting precipitation 24h；Then proceed to precipitate with chloroform for solvent extraction
To colourless, collecting chloroformic solution and be spin-dried for obtaining shallow green powder, the shallow green powder after finally collecting exists
Be after the lower 50 DEG C of dry 24h of vacuum poly-9,9 '-two (4-(9-carbazyl) phenyl) the positive fourth of fluorenes-co-9,9 '-two
Base fluorenes } product, productivity is 68%.
Test result is: Molecular weight (GPC, THF, R.I): Mn=92.3kDa,Mw/Mn=2.0。
Embodiment 6
The present embodiment is polymer LED, and its emitting layer material uses fluorenes/carbazole that embodiment 1 prepares
Base co-polymer, the most poly-9,9 '-two (4-(9-carbazyl) phenyl) and fluorenes-co-9,9 '-di-n-octyl fluorenes }.
Polymer LED, as it is shown on figure 3, include that the substrate of glass 1 stacked gradually, ITO conduct electricity sun
Pole layer 2, the hole transmission layer 3 of PEDOT-PSS material, poly-9,9 '-two (4-(9-carbazyl) phenyl)
Fluorenes-co-9,9 '-di-n-octyl fluorenes } it is the luminescent layer 4 of material, the electron injecting layer 5 of LiF material and aluminium material
Cathode layer 6；Poly-{ 9,9 '-two (the 4-(9-carbazyls) of i.e. substrate of glass 1/ITO layer 2/PEDOT-PSS layer 3/
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:
At the tin indium oxide (ITO) that surface one layer of square resistance of deposition is 10-20 Ω/mouth of glass substrate,
Form the conductive layer as anode；
On ITO substrate, one layer of PEDOT-PSS of spin coating is as hole transmission layer, and the then spin coating present invention implements
Poly-{ 9,9 '-two (4-(9-carbazyl) phenyl) fluorenes-co-9,9 '-di-n-octyl fluorenes } that example one prepares is as luminous
Layer；
Vacuum evaporation LiF on luminescent layer, as cushion；
Vacuum evaporation metallic aluminium on the light-emitting layer, forms the metallic aluminum as negative electrode, obtains described organic
Electroluminescent device.The structure of device is: ITO(150nm)/PEDOT:PSS (30nm)/luminescent layer (20nm)/
/LiF(1.5nm)/Al(150nm)
It should be appreciated that the above-mentioned statement for present pre-ferred embodiments is more detailed, therefore can not be
And it being considered the restriction to scope of patent protection of the present invention, the scope of patent protection of the present invention should be with appended right
Requirement is as the criterion.
Claims (3)
1. fluorenes/carbazyl copolymer, it is characterised in that there is following structural formula:
In formula, R is C8Alkyl, n is 65.
2. the preparation method of fluorenes/carbazyl copolymer, it is characterised in that comprise the steps:
Under nitrogen protection, by the 2 of 0.3mmol, 7-bis-bromo-9,9 '-two (4-(9-carbazyl) phenyl) fluorenes,
The 2,7-hypoboric acid pinacol ester-9,9-dioctyl fluorene of 0.3mmol, three dibenzylidenes third of 0.015mmol
Ketone two palladium, the tri-butyl phosphine of 0.01mmol are dissolved in 12mL toluene, the most again by 3mL,
The solution of potassium carbonate of 2mol/L joins in above-mentioned solution, after the most logical nitrogen purge gas about 30min,
Stir at 95 DEG C, carry out Suzuki coupled reaction 48h, after cooling, stop Suzuki coupled reaction,
Obtain reactant liquor；
In reactant liquor, add 40mL methanol precipitating, after being filtered by apparatus,Soxhlet's, use first successively
Alcohol and normal hexane extracting 24h；Then with chloroform for solvent extraction to colourless, collect chloroformic solution and be spin-dried for
Obtain shallow green powder, after collection under vacuo after 50 DEG C of dry 24h, i.e. obtain following structural formula
Poly-{ 9,9 '-two (4-(9-carbazyl) phenyl) fluorenes-co-9,9 '-di-n-octyl fluorenes }:
3. a polymer LED, it is characterised in that its emitting layer material uses fluorenes/carbazyl
Copolymer, this fluorenes/carbazyl copolymer has a following structural formula:
In formula, R is C8Alkyl, n is 65.
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| CN107759777B (en) * | 2017-11-20 | 2020-08-25 | 华南协同创新研究院 | Electroluminescent polymer and preparation method and application thereof |
| CN108517030B (en) * | 2018-04-23 | 2021-05-25 | 南京邮电大学 | Fluorenyl nano-lattice polymer and preparation method and application thereof |
| 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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| CN1490312A (en) * | 2003-09-05 | 2004-04-21 | �廪��ѧ | Carbazole derivative and its application in electroluminescent device |
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