CN103382248A - Dioxodibenzothiophene-based copolymer, preparation method thereof and polymer light emitting diode - Google Patents
Dioxodibenzothiophene-based copolymer, preparation method thereof and polymer light emitting diode Download PDFInfo
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Abstract
The invention discloses a dioxodibenzothiophene-based copolymer, a preparation method thereof and a polymer light emitting diode, which belongs to the field of organic semiconductor materials. The dioxodibenzothiophene-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 dioxodibenzothiophene-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 sulphur dioxide fluorenyl multipolymer and preparation method thereof; The invention still further relates to a kind of this sulphur dioxide fluorenyl 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 sulphur dioxide fluorenyl multipolymer.
Technical scheme of the present invention is as follows:
A kind of sulphur dioxide fluorenyl 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 sulphur dioxide fluorenyl multipolymer, comprises that step is as follows:
S1, the compd A and the compd B that provide following structural formula to represent respectively,
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 ℃, stop the Suzuki coupling reaction after cooling, obtain containing the reaction solution of described sulphur dioxide fluorenyl multipolymer, this sulphur dioxide fluorenyl multipolymer has following structural formula:
In formula, n is the integer of 10-100.
In the preparation method's of above-mentioned sulphur dioxide fluorenyl 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 sulphur dioxide fluorenyl 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 shallow green powder 50 ℃ of dry 24h under vacuum, namely get the described sulphur dioxide fluorenyl multipolymer of purifying.
The present invention also provides a kind of polymer LED, and its luminescent layer material adopts above-mentioned sulphur dioxide fluorenyl multipolymer.
In the preparation method of above-mentioned sulphur dioxide fluorenyl 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 sulphur dioxide fluorenyl multipolymer of the present invention;
Fig. 2 is the utilizing emitted light spectrogram of the sulphur dioxide fluorenyl multipolymer that makes of embodiment 1.
Fig. 3 is the structural representation of the polymer LED that makes of embodiment 6.
Embodiment
A kind of sulphur dioxide fluorenyl multipolymer provided by the invention 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 sulphur dioxide fluorenyl 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,
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 ℃, stop the Suzuki coupling reaction after cooling, obtain containing the reaction solution of sulphur dioxide fluorenyl multipolymer, this sulphur dioxide fluorenyl 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 shallow green powder 50 ℃ of dry 24h under vacuum, namely get the sulphur dioxide fluorenyl multipolymer of purifying; 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 sulphur dioxide fluorenyl 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 sulphur dioxide fluorenyl 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 sulphur dioxide fluorenyl 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/sulphur dioxide fluorenyl copolymer layer/LiF layer/aluminium lamination.
In the preparation method of above-mentioned sulphur dioxide fluorenyl 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 (Polym.Bull.DOI 10.1007/s00289-010-0372-0) is synthetic, buy on the monomer market of compd B and obtain, Lumtec. company produces, analytical pure.
Embodiment 1:
The sulphur dioxide fluorenyl multipolymer of the present embodiment, i.e. poly-{ dioxy dibenzothiophen-co-9,9 '-di-n-octyl fluorenes }, wherein, R is n-octyl, and n is 58, 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; 3; 7-dibromo dioxy dibenzothiophen (112mg; 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); be dissolved in 12mL toluene, and then solution of potassium carbonate (3mL, 2mol/L) is joined 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, is poly-{ dioxy dibenzothiophen-co-9,9 '-di-n-octyl fluorenes } product after 50 ℃ of dry 24h after collecting under vacuum, productive rate is 71%.Test result is: Molecular weight (GPC, THF, R.I): M
n=34.9kDa, M
w/ M
n=2.4.
Fig. 2 is the sulphur dioxide fluorenyl multipolymer that embodiment 1 makes, i.e. the utilizing emitted light spectrogram of poly-{ dioxy dibenzothiophen-co-9,9 '-di-n-octyl fluorenes }; X-coordinate is emission wavelength, and ordinate zou is luminous intensity.
As can be seen from Figure 2, the maximum emission peak of poly-{ dioxy dibenzothiophen-co-9,9 '-di-n-octyl fluorenes } that embodiment 1 makes is positioned at 470nm left and right, blue light wavelength.
Embodiment 2:
The sulphur dioxide fluorenyl multipolymer of the present embodiment, i.e. poly-{ dioxy dibenzothiophen-co-9,9 '-two NSC 62789 base fluorenes }, wherein, R is the NSC 62789 base, and n is 40, and 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; add 3 in flask; 7-dibromo dioxy dibenzothiophen (75mg; 0.2mmol), 2; 7-hypoboric acid pinacol ester-9; 9-two (eicosyl) fluorenes (196mg; 0.2mmol) and DMF solvent 15ml, and then with sodium carbonate solution (5mL; 2mol/L) join in mentioned solution; vacuumize deoxygenation and be filled with argon gas, 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 { dioxy dibenzothiophen-co-9,9 '-two NSC 62789 base fluorenes } product, productive rate 65%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=37.5kDa, M
w/ M
n=2.3.
Embodiment 3:
The sulphur dioxide fluorenyl multipolymer of the present embodiment, i.e. poly-{ dioxy dibenzothiophen-co-9,9 '-dimethyl fluorene }, wherein, R is methyl, and n is 86, 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, 3, 7-dibromo dioxy dibenzothiophen (112mg, 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 nitrogen purge gas 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, stir under 80 ℃, carry out Suzuki coupling 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 { dioxy dibenzothiophen-co-9,9 '-dimethyl fluorene } product after collecting after 50 ℃ of dry 24h under vacuum.Productive rate is 73%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=35kDa, M
w/ M
n=2.4.
Embodiment 4
The sulphur dioxide fluorenyl multipolymer of the present embodiment, i.e. poly-{ dioxy dibenzothiophen-co-9,9 '-two dodecyl fluorenes }, wherein, R is dodecyl, and n is 10, and 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), 3,7-dibromo dioxy dibenzothiophen (75mg, 0.2mmol) adds in the flask of the DMF solvent that fills 15ml, is dissolved into solution; And then with sodium carbonate solution (4mL, 2mol/L) join in mentioned 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 stirring under 130 ℃, carry out Suzuki coupling reaction 12h, stop the Suzuki coupling reaction after cooling, obtain reaction solution.
Add 50mL methyl alcohol in reaction solution, 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-{ dioxy dibenzothiophen-co-9,9 '-two dodecyl fluorenes } product, productive rate 62% after 50 ℃ of dry 24h under vacuum.
Test result is: Molecular weight (GPC, THF, R.I): M
n=8.2kDa, M
w/ M
n=2.5.
Embodiment 5
The sulphur dioxide fluorenyl multipolymer of the present embodiment, i.e. poly-{ dioxy dibenzothiophen-co-9,9 '-di-n-butyl fluorenes }, wherein, R is normal-butyl, and n is 100, and 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), 3, 7-dibromo dioxy dibenzothiophen (112mg, 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 mentioned 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, stir under 70 ℃, carry out Suzuki coupling 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-{ dioxy dibenzothiophen-co-9,9 '-di-n-butyl fluorenes } product after 50 ℃ of dry 24h under vacuum, productive rate is 87%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=49kDa, M
w/ M
n=2.1.
Embodiment 6
The present embodiment is polymer LED, the sulphur dioxide fluorenyl multipolymer that its luminescent layer material adopts embodiment 1 to make, i.e. poly-{ dioxy dibenzothiophen-co-9,9 '-di-n-octyl fluorenes }.
Polymer LED, as shown in Figure 3, comprise that the hole transmission layer 3 of the substrate of glass 1 that stacks gradually, ITO conductive anode layer 2, PEDOT-PSS material, poly-{ dioxy dibenzothiophen-co-9,9 '-di-n-octyl fluorenes } are 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-{ dioxy dibenzothiophen-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 what then the spin coating embodiment of the present invention one made gathers { dioxy dibenzothiophen-co-9,9 '-di-n-octyl fluorenes } 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. sulphur dioxide fluorenyl 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 a sulphur dioxide fluorenyl multipolymer, is characterized in that, S1, the compd A and the compd B that provide following structural formula to represent respectively are provided,
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 ℃, stop the Suzuki coupling reaction after cooling, obtain containing the reaction solution of described sulphur dioxide fluorenyl multipolymer, this sulphur dioxide fluorenyl multipolymer has following structural formula:
In formula, n is the integer of 10-100.
3. the preparation method of sulphur dioxide fluorenyl multipolymer according to claim 2, 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 sulphur dioxide fluorenyl 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 sulphur dioxide fluorenyl multipolymer according to claim 2, 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 sulphur dioxide fluorenyl 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 sulphur dioxide fluorenyl multipolymer according to claim 2, 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 sulphur dioxide fluorenyl multipolymer according to claim 2, 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 sulphur dioxide fluorenyl multipolymer according to claim 2, is characterized in that, after finishing in step S2, also comprises the purification process process to described sulphur dioxide fluorenyl 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 shallow green powder 50 ℃ of dry 24h under vacuum, namely get the described sulphur dioxide fluorenyl multipolymer of purifying.
10. a polymer LED, is characterized in that, its luminescent layer material adopts sulphur dioxide fluorenyl multipolymer, and this sulphur dioxide fluorenyl multipolymer has following structural formula:
In formula, R is C
1～C
20Alkyl, n is the integer of 10-100.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104004165A (en) * | 2014-05-07 | 2014-08-27 | 华南理工大学 | S,S-dioxo-dibenzothiophene unit-containing electron donor polymer and use thereof |
| CN106243329A (en) * | 2016-07-29 | 2016-12-21 | 华南理工大学 | One is based on S, S dioxydibenze thiophthene derivative replaces conjugated polymer luminescent material and preparation method and application to receptor type |
| CN107739428A (en) * | 2017-09-04 | 2018-02-27 | 华南理工大学 | Side chain is poly- containing hole transporting unit（Fluorenes co S, S dioxydibenze bithiophenes）Derivative and its preparation method and application |
| CN110951049A (en) * | 2018-09-26 | 2020-04-03 | 华南协同创新研究院 | Light-emitting polymer, preparation method thereof and application thereof in preparing light-emitting diode |
| TWI703135B (en) * | 2015-09-28 | 2020-09-01 | 日商東麗股份有限公司 | Polymer compound, resin composition, film, solid-state imaging device, method of manufacturing polymer compound, method of manufacturing solid-state imaging device, and optical device |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1528804A (en) * | 2003-09-29 | 2004-09-15 | 上海交通大学 | Polymer containing dibenzo-dioxy thiophene group and preparing method thereof |
| CN101255336A (en) * | 2007-11-06 | 2008-09-03 | 华南理工大学 | Electroluminescent spectrum-stable blue fluorene-based polymers as well as preparation method and uses thereof |
| CN101712674A (en) * | 2009-11-13 | 2010-05-26 | 华南理工大学 | Alkyl substituted-S,S-dioxo-dibenzothiophene monomer, preparation method and polymer thereof |
| WO2011033078A1 (en) * | 2009-09-18 | 2011-03-24 | Thorn Lighting Limited | Electroluminescent materials and devices |
-
2012
- 2012-05-04 CN CN2012101374830A patent/CN103382248A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1528804A (en) * | 2003-09-29 | 2004-09-15 | 上海交通大学 | Polymer containing dibenzo-dioxy thiophene group and preparing method thereof |
| CN101255336A (en) * | 2007-11-06 | 2008-09-03 | 华南理工大学 | Electroluminescent spectrum-stable blue fluorene-based polymers as well as preparation method and uses thereof |
| WO2011033078A1 (en) * | 2009-09-18 | 2011-03-24 | Thorn Lighting Limited | Electroluminescent materials and devices |
| CN101712674A (en) * | 2009-11-13 | 2010-05-26 | 华南理工大学 | Alkyl substituted-S,S-dioxo-dibenzothiophene monomer, preparation method and polymer thereof |
Non-Patent Citations (2)
| Title |
|---|
| JIE LIU ET AL.: "Novel Spectrally Stable Saturated Blue-Light-Emitting Poly[(fluorene)-co-(dioctyldibenzothiophene-S,S-dioxide)]s", 《MACROMOLECULAR RAPID COMMUNICATION》, vol. 31, no. 5, 2 March 2010 (2010-03-02), pages 496 - 501 * |
| YUANYUAN LI ET AL.: "Enhancement of spectral stability and efficiency on blue light-emitters via introducing dibenzothiophene-S,S-dioxide isomers into polyfluorene backbone", 《ORGANIC ELECTRONICS》, vol. 10, 7 May 2009 (2009-05-07), pages 901 - 909, XP026235902, DOI: doi:10.1016/j.orgel.2009.04.021 * |
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| CN104004165A (en) * | 2014-05-07 | 2014-08-27 | 华南理工大学 | S,S-dioxo-dibenzothiophene unit-containing electron donor polymer and use thereof |
| CN104004165B (en) * | 2014-05-07 | 2016-08-24 | 华南理工大学 | Electron donor polymer and application thereof containing S, S-dioxo-dibenzothiophene unit |
| TWI703135B (en) * | 2015-09-28 | 2020-09-01 | 日商東麗股份有限公司 | Polymer compound, resin composition, film, solid-state imaging device, method of manufacturing polymer compound, method of manufacturing solid-state imaging device, and optical device |
| CN106243329A (en) * | 2016-07-29 | 2016-12-21 | 华南理工大学 | One is based on S, S dioxydibenze thiophthene derivative replaces conjugated polymer luminescent material and preparation method and application to receptor type |
| CN106243329B (en) * | 2016-07-29 | 2019-06-18 | 华南理工大学 | One kind being based on S, and S- dioxydibenze thiophthene derivative replaces conjugated polymer luminescent material and the preparation method and application thereof to receptor type |
| CN107739428A (en) * | 2017-09-04 | 2018-02-27 | 华南理工大学 | Side chain is poly- containing hole transporting unit（Fluorenes co S, S dioxydibenze bithiophenes）Derivative and its preparation method and application |
| CN110951049A (en) * | 2018-09-26 | 2020-04-03 | 华南协同创新研究院 | Light-emitting polymer, preparation method thereof and application thereof in preparing light-emitting diode |
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