CN104177597A - Polymer of fluorene/oxadiazole group, preparation method and organic electroluminescent device thereof - Google Patents

Polymer of fluorene/oxadiazole group, preparation method and organic electroluminescent device thereof Download PDF

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Publication number
CN104177597A
CN104177597A CN201310204213.1A CN201310204213A CN104177597A CN 104177597 A CN104177597 A CN 104177597A CN 201310204213 A CN201310204213 A CN 201310204213A CN 104177597 A CN104177597 A CN 104177597A
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polymkeric substance
oxadiazolyl
preparation
solution
palladium
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周明杰
张振华
王平
黄辉
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Oceans King Lighting Science and Technology Co Ltd
Shenzhen Oceans King Lighting Science and Technology Co Ltd
Shenzhen Oceans King Lighting Engineering Co Ltd
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Oceans King Lighting Science and Technology Co Ltd
Shenzhen Oceans King Lighting Engineering Co Ltd
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Abstract

Belonging to the field of organic semiconductor materials, the invention discloses a polymer of fluorene/oxadiazole group, a preparation method and an organic electroluminescent device thereof. The polymer has a structural formula shown as the specification, wherein R is alkyl of C1-C20, and n is an integer of 16-97. The polymer of fluorene/oxadiazole group provided by the invention has the fluorine and oxadiazole basic unit, and the material has good hole transporting ability, so that the luminescence efficiency is greatly improved.

Description

Polymkeric substance of Wu/oxadiazolyl and preparation method thereof and organic electroluminescence device
Technical field
The present invention relates to organic semiconductor material field, relate in particular to polymkeric substance of a kind of Wu/oxadiazolyl and preparation method thereof.The invention still further relates to the polymkeric substance that uses Wu/oxadiazolyl as the organic electroluminescence device of active coating electron donor material.
Background technology
Since Japanese scientist's Hideki Shirakawa in 1977 is found polyacetylene conduction, this being called as the conductive polymers of " the 4th generation polymer " material attracted numerous scientists to study with its outstanding photoelectric properties.Conducting polymer is compared with the inorganic materials with identical or close purposes, has density low, and easily processing, synthesizes the advantages such as range of choice is wide.Due to the conjugate property of this class material structure, make its can transmission charge, stimulated luminescence, thus can or potential may being applied on many electronics or opto-electronic device, for example comprise polymer LED, photovoltaic cell, field-effect etc.Potential application prospect and wide application field impel scientist competitively to study this class to have the conjugation material of photoelectric activity, comprise conjugated structure small molecules, and polyacetylene, polypyrrole, Polythiophene, polyaniline, poly-fluorenes, polycarbazole etc.
Researchist is making great efforts to seek to improve the method for polymer LED, photovoltaic cell, field effect behavior always, and material is one of most important factor.So being devoted to exploitation always, many research groups there is high-quantum efficiency, high color purity, the luminescence polymer that permanent stability are good, and the polymkeric substance that visible-range absorption bands is wide, carrier mobility is high.Realize these targets, need to develop more novel conjugated molecular material and polymer materials, wherein design synthesizing new conjugate unit and just seem very important.
Summary of the invention
Problem to be solved by this invention is to provide one to have high-quantum efficiency, high color purity, and permanent stability are good, and the polymkeric substance of the Wu/oxadiazolyl that visible-range absorption bands is wide, carrier mobility is high.
Technical scheme of the present invention is as follows:
A polymkeric substance for Wu/oxadiazolyl, its structural formula is as follows:
In formula, R is C 1～C 20alkyl, integer between n is 16-97; Wherein, in the polymkeric substance of fluorenes/oxadiazolyl, brace represents that this polymkeric substance contains fluorene group and oxadiazole group.
The present invention also provides the preparation method of the polymkeric substance of above-mentioned Wu/oxadiazolyl, comprises the steps:
The compd A and the B that provide respectively following structural formula to represent,
wherein, R is C 1～C 20alkyl;
Under oxygen-free environment, the compd A that is 1:1～1.2 by mol ratio and B are added in the organic solvent that contains catalyzer and alkaline solution and dissolve, at 70～130 DEG C, carry out Suzuki coupling reaction 12～96 hours subsequently, stop after coupling reaction, separating-purifying reaction solution, obtains the polymkeric substance of the Wu/oxadiazolyl of following structural formula:
in formula, the integer that n is 16-97.
The preparation method of the polymkeric substance of described Wu/oxadiazolyl, wherein, oxygen-free environment is made up of one or both in argon gas, nitrogen.
The preparation method of the polymkeric substance of described Wu/oxadiazolyl, wherein, described catalyzer is bi triphenyl phosphine dichloride palladium or tetra-triphenylphosphine palladium; Or
Described catalyzer is the mixture of organic palladium and organophosphorus ligand, and in mixture, the molar weight of organophosphorus ligand is 4～8 times of organic palladium molar weight; Described organic palladium is palladium or three or two argon benzyl acetone two palladiums; Organophosphorus ligand is tri-o-tolyl phosphine or 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl;
The mol ratio of described catalyzer and described compd A is 1:20～1:100.
The preparation method of the polymkeric substance of described Wu/oxadiazolyl, wherein, described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate and sodium hydrogen carbonate solution; In described alkaline solution, the molar weight of alkali solute is 20 times of compd A molar weight.
The preparation method of the polymkeric substance of described Wu/oxadiazolyl, wherein, described organic solvent is at least one in toluene, DMF, tetrahydrofuran (THF).
The preparation method of the polymkeric substance of described Wu/oxadiazolyl, wherein, Suzuki coupling reaction temperature is 90～120 DEG C, the reaction times is 24～72 hours.
The preparation method of the polymkeric substance of described Wu/oxadiazolyl, wherein, separating-purifying reaction solution comprises:
After coupling reaction, in reaction solution, add methyl alcohol precipitating, filter by apparatus,Soxhlet's subsequently, using successively again methyl alcohol and normal hexane extracting, obtain organic phase, then taking chloroform as solvent extraction organic phase to colourless, collect chloroformic solution and be spin-dried for, after the lower 50 DEG C of dry 24h of vacuum, obtain the polymkeric substance of described Wu/oxadiazolyl.
The invention still further relates to a kind of organic electroluminescence device, the material of its luminescent layer includes the polymkeric substance of the Wu/oxadiazolyl of following structural formula:
In formula, R is C 1～C 20alkyl, integer between n is 16-97; This polymkeric substance is mainly used for the material of main part of luminescent layer.
The polymkeric substance of Wu/oxadiazolyl of the present invention, for Wu/oxadiazolyl multipolymer Blue-light emitting host material, there is the basic unit of fluorenes and oxadiazole, this material has good cavity transmission ability, second-order transition temperature is high, can form that stability is high, the amorphous thin film of good uniformity, can be used as the luminescent layer of organic electroluminescence device, the organic electroluminescence device based on this polymkeric substance can improve efficiency.In addition, this polymer architecture is regular, and quantum yield is high, high color purity.
Above-mentioned preparation method, has adopted better simply synthetic route, thereby reduces technical process, and starting material are cheap and easy to get, and manufacturing cost is reduced; And worth polymeric material novel structure, solubility property is good, and film forming properties is good, and absorption region is wide, and effciency of energy transfer is improved.
Brief description of the drawings
Fig. 1 is the fluorescence spectrum figure of the polymkeric substance of the Wu/oxadiazolyl of embodiment 1;
Fig. 2 is the structural representation of the organic electroluminescence device of embodiment 6.
Embodiment
In order to understand better the content of patent of the present invention, 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 the monomer of compd A, compd B is all bought and is obtained from the market.
Embodiment 1:
The polymkeric substance of the Wu/oxadiazolyl of the present embodiment, i.e. poly-{ 9-(the positive hexyloxy phenyl of 4-)-2,7-bis-bases-9H-carbazole-co-5,5'-(4,4'-(2,7-, bis-bases-9H-fluorenes-9,9-bis-bases) dioxy two (4,1-penylene)) two (2-(4-tert-butyl-phenyl)-1,3,4-oxadiazole) } (wherein, R is normal hexane base, n=65), 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-(the positive hexyloxy phenyl of 4-)-2, 7-bis-tetramethyl ethylene ketone boric acid ester-9H-carbazole (119mg, 0.2mmol), 5, 5'-(4, 4'-(2, the bromo-9H-of 7-bis-fluorenes-9, 9-bis-bases) dioxy two (4, 1-penylene)) two (2-(4-tert-butyl-phenyl)-1, 3, 4-oxadiazole) (182mg, 0.2mmol) add in the flask that fills 10ml toluene solvant, after fully dissolving by salt of wormwood (2mL, 2mol/L) solution joins 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 DEG C and carries out Suzuki coupling reaction 48h.Subsequently, after cooling, stop polyreaction, in 50ml methyl alcohol, carry out sedimentation to dripping in flask; After filtering by apparatus,Soxhlet's, use successively methyl alcohol and normal hexane extracting 24h.Then taking chloroform as solvent extraction to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, after collection, under vacuum, after 50 DEG C of dry 24h, obtain product, productive rate 75%.
Test result is: Molecular weight (GPC, THF, R.I): M n=61.4kDa, M w/ M n=2.2.
Fig. 1 is the fluorescence spectrum figure of the polymkeric substance in embodiment 1; Fluorescence spectrum is measured in Jasco FP-6600 type fluorescence spectrophotometer.From Fig. 1, can know, the maximum emission peak of this polymer materials is positioned at 430nm left and right, transmitting blue light.
Embodiment 2:
The polymkeric substance of the Wu/oxadiazolyl of the present embodiment, i.e. poly-{ 9-(4-p-methoxy-phenyl)-2,7-bis-bases-9H-carbazole-co-5,5'-(4,4'-(2,7-, bis-bases-9H-fluorenes-9,9-bis-bases) dioxy two (4,1-penylene)) two (2-(4-tert-butyl-phenyl)-1,3,4-oxadiazole) } (wherein, R is methyl, n=81), 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-(4-p-methoxy-phenyl)-2, 7-bis-tetramethyl ethylene ketone boric acid ester-9H-carbazole (136mg, 0.3mmol), 5, 5'-(4, 4'-(2, the bromo-9H-of 7-bis-fluorenes-9, 9-bis-bases) dioxy two (4, 1-penylene)) two (2-(4-tert-butyl-phenyl)-1, 3, 4-oxadiazole) (271mg, 0.3mmol) add in the two-mouth bottle of 50mL specification with 15mL tetrahydrofuran (THF), after fully dissolving, pass into after the about 20min of gas mixture air-discharging of nitrogen and argon gas, then by tetra-triphenylphosphine palladium (4mg, 0.003mmol) add wherein, after fully dissolving, add again sodium bicarbonate (3mL, 2mol/L) solution.After the about 10min of gas mixture air-discharging of fully logical nitrogen and argon gas, two-mouth bottle is joined to 70 DEG C and carry out Suzuki coupling reaction 96h again.Subsequently, after cooling, stop polyreaction, 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 taking chloroform as solvent extraction to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, after collection, under vacuum, after 50 DEG C of dry 24h, obtain product.Productive rate is 73%.
Test result is: Molecular weight (GPC, THF, R.I): M n=73.7kDa, M w/ M n=2.1.
Embodiment 3:
The polymkeric substance of the Wu/oxadiazolyl of the present embodiment, i.e. poly-{ 9-(4-p-methoxy-phenyl)-2,7-bis-bases-9H-carbazole-co-5,5'-(4,4'-(2,7-, bis-bases-9H-fluorenes-9,9-bis-bases) dioxy two (4,1-penylene)) two (2-(4-tert-butyl-phenyl)-1,3,4-oxadiazole) } (wherein, R is NSC 62789 base, n=97), 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-(4-NSC 62789 oxygen base phenyl)-2, 7-bis-tetramethyl ethylene ketone boric acid ester-9H-carbazole (299mg, 0.3mmol), 5, 5'-(4, 4'-(2, the bromo-9H-of 7-bis-fluorenes-9, 9-bis-bases) dioxy two (4, 1-penylene)) two (2-(4-tert-butyl-phenyl)-1, 3, 4-oxadiazole) (300mg, 0.33mmol), palladium (3.5mg, 0.015mmol) He three (o-methoxyphenyl) phosphine (21mg, 0.06mmol) join the N that fills 12mL, in the flask of dinethylformamide, after fully dissolving, add salt of wormwood (3mL, 2mol/L) solution, in flask, lead to after the about 30min of nitrogen purge gas subsequently, flask is heated to 130 DEG C and carries out Suzuki coupling reaction 12h.Subsequently, after cooling, stop polyreaction, in flask, add 40mL methyl alcohol precipitating, after filtering by apparatus,Soxhlet's, use successively methyl alcohol and normal hexane extracting 24h; Then taking chloroform as solvent extraction to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, after collection, under vacuum, after 50 DEG C of dry 24h, be product, productive rate 71%.
Test result is: Molecular weight (GPC, THF, R.I): M n=129.6kDa, M w/ M n=2.0.
Embodiment 4:
The polymkeric substance of the Wu/oxadiazolyl of the present embodiment, i.e. poly-{ 9-(4-n-butoxy phenyl)-2,7-bis-bases-9H-carbazole-co-5,5'-(4,4'-(2,7-, bis-bases-9H-fluorenes-9,9-bis-bases) dioxy two (4,1-penylene)) two (2-(4-tert-butyl-phenyl)-1,3,4-oxadiazole) } (wherein, R is normal-butyl, n=16), 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-(4-n-butoxy phenyl)-2, 7-bis-tetramethyl ethylene ketone boric acid ester-9H-carbazole (162mg, 0.3mmol), 5, 5'-(4, 4'-(2, the bromo-9H-of 7-bis-fluorenes-9, 9-bis-bases) dioxy two (4, 1-penylene)) two (2-(4-tert-butyl-phenyl)-1, 3, 4-oxadiazole) (327mg, 0.36mmol), three or two argon benzyl acetone two palladium (9mg, 0.009mmol) with 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl (29mg, 0.072mmol) join the N that fills 12mL, in the flask of dinethylformamide, after fully dissolving, add sodium bicarbonate (3mL, 2mol/L) solution.In flask, lead to after the about 30min of nitrogen purge gas subsequently; Flask is heated to 120 DEG C and carries out Suzuki coupling reaction 36h.Subsequently, after cooling, stop polyreaction, in flask, add 40mL methyl alcohol precipitating, after filtering by apparatus,Soxhlet's, use successively methyl alcohol and normal hexane extracting 24h; Then taking chloroform as solvent extraction to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, after collection, under vacuum, after 50 DEG C of dry 24h, be product, productive rate is 68%.
Test result is: Molecular weight (GPC, THF, R.I): M n=18.3kDa, M w/ M n=2.4.
Embodiment 5:
The polymkeric substance of the Wu/oxadiazolyl of the present embodiment, i.e. poly-{ 9-(4-n-octyloxy phenyl)-2,7-bis-bases-9H-carbazole-co-5,5'-(4,4'-(2,7-, bis-bases-9H-fluorenes-9,9-bis-bases) dioxy two (4,1-penylene)) two (2-(4-tert-butyl-phenyl)-1,3,4-oxadiazole) } (wherein, R is n-octyl, n=43), 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-(4-n-octyloxy phenyl)-2, 7-bis-tetramethyl ethylene ketone boric acid ester-9H-carbazole (197mg, 0.3mmol), 5, 5'-(4, 4'-(2, the bromo-9H-of 7-bis-fluorenes-9, 9-bis-bases) dioxy two (4, 1-penylene)) two (2-(4-tert-butyl-phenyl)-1, 3, 4-oxadiazole) (327mg, 0.36mmol) add in the two-mouth bottle of 50mL specification with 15mL toluene, after fully dissolving, pass into after the about 20min of gas mixture air-discharging of nitrogen and argon gas, then by tetra-triphenylphosphine palladium (8mg, 0.006mmol) add wherein, add again salt of wormwood (3mL, 2mol/L) solution.After the about 10min of gas mixture air-discharging of fully logical nitrogen and argon gas, two-mouth bottle is joined to 90 DEG C and carry out Suzuki coupling reaction 60h again.Subsequently, after cooling, stop polyreaction, 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 taking chloroform as solvent extraction to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, after collection, under vacuum, after 50 DEG C of dry 24h, obtain product.Productive rate is 80%.
Test result is: Molecular weight (GPC, THF, R.I): M n=91.2kDa, M w/ M n=2.2.
Embodiment 6:
Originally be embodied as organic electroluminescence device, the polybutadiene homopolymer of the Wu/oxadiazolyl that the material employing embodiment 1 of its luminescent layer makes, i.e. poly-{ 9-(4-n-octyloxy phenyl)-2,7-bis-bases-9H-carbazole-co-5,5'-(4,4'-(2,7-bis-bases-9H-fluorenes-9,9-bis-bases) dioxy two (4,1-penylene)) two (2-(4-tert-butyl-phenyl)-1,3,4-oxadiazole) }; Certainly, also can adopt the polybutadiene homopolymer of arbitrary Wu/oxadiazolyl that embodiment 2～5 makes.
As shown in Figure 2, this organic electroluminescence device comprises substrate 1, stacks gradually anode layer 2, hole transmission layer 3, luminescent layer 4, electron injecting layer 5 and cathode layer 6 on substrate 1 one surfaces; Wherein, the material of each functional layer is as follows:
The material of substrate 1 is glass;
The material of anode layer 2 is tin indium oxide compound (ITO), and thickness is 150nm; ITO is produced on glass surface, is called for short ito glass; It is the ITO of 10-20 Ω/mouth that ITO selects square resistance.
The material of hole transmission layer 3 is the mixture of 3,4-ethylenedioxy thiazole (PEDOT) and polystyrene-sulfonic acid matrix material (PSS), is expressed as PEDOT:PSS, and thickness is 30nm;
The material of luminescent layer 4 is the poly-{ 9-(4-n-octyloxy phenyl)-2 that embodiment 1 makes, 7-bis-bases-9H-carbazole-co-5,5'-(4,4'-(2,7-, bis-bases-9H-fluorenes-9,9-bis-bases) dioxy two (4,1-penylene)) two (2-(4-tert-butyl-phenyl)-1,3,4-oxadiazole) } (representing with P1), thickness is 20nm;
The material of electron injecting layer 5 is LiF, and thickness is 1.5nm;
The material of cathode layer 6 is aluminium, and thickness is 150nm.
Therefore, the structure of this organic electroluminescence device can be expressed as: glass/ITO/PEDOT:PSS/P1//LiF/Al, wherein, brace represents laminate structure.
The above embodiment has only expressed several embodiment of the present invention, and it describes comparatively concrete and detailed, but can not therefore be interpreted as the restriction to the scope of the claims of the present invention.It should be pointed out that for the person of ordinary skill of the art, without departing from the inventive concept of the premise, can also make some distortion and improvement, these all belong to protection scope of the present invention.Therefore, the protection domain of patent of the present invention should be as the criterion with claims.

Claims (10)

1. a polymkeric substance for fluorenes/oxadiazolyl, is characterized in that, its structural formula is as follows:
In formula, R is C 1～C 20alkyl, integer between n is 16-97.
2. the polymkeric substance of Wu/oxadiazolyl according to claim 2, is characterized in that, comprises the one in following polymkeric substance:
3. a preparation method for the polymkeric substance of fluorenes/oxadiazolyl, is characterized in that, comprises the steps:
The compd A and the B that provide respectively following structural formula to represent,
wherein, R is C 1～C 20alkyl;
Under oxygen-free environment, the compd A that is 1:1～1.2 by mol ratio and B are added in the organic solvent that contains catalyzer and alkaline solution and dissolve, at 70～130 DEG C, carry out Suzuki coupling reaction 12～96 hours subsequently, stop after coupling reaction, separating-purifying reaction solution, obtains the polymkeric substance of the Wu/oxadiazolyl of following structural formula:
in formula, the integer that n is 16-97.
4. the preparation method of the polymkeric substance of Wu/oxadiazolyl according to claim 3, is characterized in that, described catalyzer is bi triphenyl phosphine dichloride palladium or tetra-triphenylphosphine palladium; Or described catalyzer is the mixture of organic palladium and organophosphorus ligand, and in mixture, the molar weight of organophosphorus ligand is 4～8 times of organic palladium molar weight; The mol ratio of described catalyzer and described compd A is 1:20～1:100.
5. the preparation method of the polymkeric substance of Wu/oxadiazolyl according to claim 4, is characterized in that, described organic palladium is palladium or three or two argon benzyl acetone two palladiums; Organophosphorus ligand is tri-o-tolyl phosphine or 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl.
6. the preparation method of the polymkeric substance of Wu/oxadiazolyl according to claim 3, is characterized in that, described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate and sodium hydrogen carbonate solution; In described alkaline solution, the molar weight of alkali solute is 20 times of compd A molar weight.
7. the preparation method of the polymkeric substance of Wu/oxadiazolyl according to claim 3, is characterized in that, described organic solvent is at least one in toluene, DMF, tetrahydrofuran (THF).
8. the preparation method of the polymkeric substance of Wu/oxadiazolyl according to claim 3, is characterized in that, Suzuki coupling reaction temperature is 90～120 DEG C, and the reaction times is 24～72 hours.
9. the preparation method of the polymkeric substance of Wu/oxadiazolyl according to claim 3, is characterized in that, separating-purifying reaction solution comprises:
After coupling reaction, in reaction solution, add methyl alcohol precipitating, filter by apparatus,Soxhlet's subsequently, using successively again methyl alcohol and normal hexane extracting, obtain organic phase, then taking chloroform as solvent extraction organic phase to colourless, collect chloroformic solution and be spin-dried for, after the lower 50 DEG C of dry 24h of vacuum, obtain the polymkeric substance of described Wu/oxadiazolyl.
10. an organic electroluminescence device, is characterized in that, the material of its luminescent layer includes the polymkeric substance of the fluorenes/oxadiazolyl of following structural formula:
In formula, R is C 1～C 20alkyl, integer between n is 16-97.
CN201310204213.1A 2013-05-28 2013-05-28 Polymer of fluorene/oxadiazole group, preparation method and organic electroluminescent device thereof Pending CN104177597A (en)

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US20060217527A1 (en) * 2003-06-17 2006-09-28 National Tsing Hua Univesity Electroluminescent conjugated polymers containing phosphorescent moieties and the application thereof in LED
US20120232237A1 (en) * 2009-11-18 2012-09-13 Zhao Li Fluorinated Monomers, Oligomers and Polymers for Use in Organic Electronic Devices
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Title
FANG-IY WU ET AL.: "Highly Efficient Light-Emitting Diodes Based on Fluorene Copolymer Consisting of Triarylamine Units in the Main Chain and Oxadiazole Pendent Groups", 《MACROMOLECULES》, vol. 38, 30 September 2005 (2005-09-30), pages 9028 - 9036 *
HSIAO-HSIEN SUNG ET AL.: "Synthesis and Characterization of Poly(fluorene)-Based Copolymers Containing Various 1,3,4-Oxadiazole Pendants", 《JOURNAL OF POLYMER SCIENCE: PART A: POLYMER CHEMISTRY》, vol. 43, 31 December 2005 (2005-12-31), pages 2700 - 2711, XP055134078, DOI: doi:10.1002/pola.20741 *

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Application publication date: 20141203