CN103606631A - Polymer light emitting diode having hole transport layer - Google Patents
Polymer light emitting diode having hole transport layer Download PDFInfo
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- CN103606631A CN103606631A CN201310510887.4A CN201310510887A CN103606631A CN 103606631 A CN103606631 A CN 103606631A CN 201310510887 A CN201310510887 A CN 201310510887A CN 103606631 A CN103606631 A CN 103606631A
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- thiophene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
Abstract
The invention discloses a polymer light emitting diode having a hole transport layer. The polymer light emitting diode comprises a substrate, an anode, a hole transport layer, a polymer light emitting layer and a cathode, wherein the material of the polymer light emitting layer is a conjugated polymer, with a general formula (I) structure, of benzothiadiazole. By adopting the polymer light emitting layer as an efficient light-emitting polymer, the polymer light emitting diode has high energy conversion efficiency and high carrier mobility.
Description
Technical field
The present invention relates to a kind of photoelectric device, relate in particular to a kind of light-emitting diode.
Background technology
Polymer LED has lower cost for material, driving voltage is low, active illuminating, visual angle is wide, the features such as energy consumption is low, are more easy to large area moulding, and emission wavelength can be by advantages such as Molecular Design regulate, the panchromatic flat-panel screens of high-resolution can be widely used in, also polymer solar battery can be applied to.
When adding forward bias at polymer LED two ends, hole is injected into the valence band of polymer light-emitting layer and is moved to negative pole by positive pole, and electronics is injected into the conduction band of polymer light-emitting layer and is moved to positive pole by negative pole.Hole and electronics are captured mutually in transition process, are combined into exciton, the electronics generation radiation transistion of exciton state, and energy discharges with photon form, realizes electroluminescence.But, in prior art still there are some defects in light-emitting diode, the complicated process of preparation of flexible light-emitting diode, cost is high, the luminescent properties of the light-emitting diode of preparation can not be satisfied the demand, therefore wish a kind of better performance of research and development organic/polymer LED, efficiency is high, preparation technology is simple and cost is low.
Summary of the invention
Polymer LED of the present invention comprises substrate, anode, hole transmission layer, polymer light-emitting layer and negative electrode, wherein,
The material of polymer light-emitting layer is the conjugated polymer with the diazosulfide of general formula (I) structure,
Wherein, R
1for hydrogen or C
1～C
36alkyl; R
2for hydrogen or C
1～C
36alkyl; Ar is that thiophene, alkylated substituted thiazoline fen, alkoxyl substituted thiophene, bithiophene, alkyl replace bithiophene, alkoxyl and replace a kind of in bithiophene; N=3～1000.
The preparation method of the conjugated polymer of above-mentioned diazosulfide carries out copolymerization by the monomer of diazosulfide and thiophene monomer or oligo-thiophenes monomer.
Further preferred, the preparation method of the conjugated polymer of above-mentioned diazosulfide is by 5, the fluoro-diazosulfide monomer of 6-bis-is with connection three thiophene monomers or join four thiophene monomers and carry out copolymerization, or by 4, two thiophene-5 of 7-, the fluoro-diazosulfide monomer of 6-bis-and thiophene monomer or bithiophene monomer carry out copolymerization.
Compared with prior art, tool of the present invention has the following advantages and effect: the conjugated polymer of this diazosulfide, for making the luminescent layer of polymer LED, makes this light-emitting diode have high energy conversion efficiency, has high carrier mobility.
Accompanying drawing explanation
Fig. 1 is the structural representation of light-emitting diode of the present invention.
Embodiment
In order to make the clearer understanding of those skilled in the art technical scheme of the present invention, below in conjunction with accompanying drawing, its embodiment is described.
As shown in Figure 1, light-emitting diode of the present invention comprises substrate 1, anode 2, hole transmission layer 5, polymer light-emitting layer 3 and negative electrode 4.Wherein,
Polymer light-emitting layer 3 adopts the method preparations such as spin coating, printing conventionally.
The material of polymer light-emitting layer 3 is the conjugated polymers with the diazosulfide of general formula (I) structure:
Wherein, R
1for hydrogen or C
1～C
36alkyl; R
2for hydrogen or C
1～C
36alkyl; Ar is that thiophene, alkylated substituted thiazoline fen, alkoxyl substituted thiophene, bithiophene, alkyl replace bithiophene, alkoxyl and replace a kind of in bithiophene; N=3～1000.
The preparation method of the conjugated polymer of above-mentioned diazosulfide carries out copolymerization by the monomer of diazosulfide and thiophene monomer or oligo-thiophenes monomer.
The preparation method of the conjugated polymer of above-mentioned diazosulfide is by 5, the fluoro-diazosulfide monomer of 6-bis-is with connection three thiophene monomers or join four thiophene monomers and carry out copolymerization, or by two thiophene-5 of 4,7-, the fluoro-diazosulfide monomer of 6-bis-and thiophene monomer or bithiophene monomer carry out copolymerization.
Embodiment 1:
1,2-diaminourea-4,5-bis-is fluoro-3, the preparation of 6-dibromobenzene, reaction equation is as follows:
In the twoport flask of 500 milliliters, add 2,3-bis-fluoro-5, (25.60 grams of 6-dinitro-Isosorbide-5-Nitrae-dibromobenzene (13.24 grams, 36.57 mMs) and reduced iron powders, 457.14 mMs), under inert atmosphere, add 200 milliliters of glacial acetic acid, be heated to 45 degrees Celsius of reactions 4 hours.
Reaction finishes to be cooled to after room temperature, in the NaOH aqueous solution that to be poured into 200 milliliters of temperature and to be 5 degrees Celsius, percentage by weight be 5%, and with dichloromethane extraction 3 times, the saturated NaHCO of organic phase
3the aqueous solution is washed 2 times and with anhydrous magnesium sulfate drying, is removed solvent after separation, with silica gel chromatographic column separating-purifying, obtains pale solid.Warp
1hNMR,
13cNMR, and elementary analysis test is indicated as target product 1,2-diaminourea-4,5-bis-is fluoro-3,6-dibromobenzene.
Embodiment 2:
5,6-bis-is fluoro-4, the preparation of 7-dibromo diazosulfide, and reaction equation is as follows:
At 500 milliliters of two mouthfuls of flasks that are placed in ice-water bath, add 1,2-diaminourea-4,5-bis-is fluoro-3,6-dibromobenzene (3.32 grams, 11.00 mMs), 4.7 milliliters of triethylamines and 150 milliliters of anhydrous chloroforms.Under inert atmosphere, in well-beaten solution, drip 1.9 milliliters of thionyl chlorides, be heated to subsequently 70 degrees Celsius of reactions and spend the night.After reaction finishes, reactant liquor is poured in 250 ml waters, with dichloromethane extraction, also used anhydrous magnesium sulfate drying organic phase, the separated rear solvent of removing, obtains white solid with silica gel chromatographic column separating-purifying.Warp
13cNMR, and elementary analysis test is indicated as target product 5,6-bis-is fluoro-4,7-dibromo diazosulfide.
Embodiment 3:
Two (the 4-alkylthrophene-2-yls)-5 of 4,7-, the preparation of 6-bis-fluoro-diazosulfides, reaction equation is as follows:
To prepare two (the 4-(2-decyl myristyl) thiophene-2-yls of 4,7-)-5, the fluoro-diazosulfide of 6-bis-is that example is explained.In two mouthfuls of flasks of 50 milliliters, add 5; 6-bis-fluoro-4; (330 milligrams of 7-dibromo diazosulfides; 1.00 mMs), tributyl-(4-(2-decyl myristyl) thiophene-2-yl) alkane tin (2.13 grams, 3.00 mMs); logical nitrogen 30 minutes; then add 268 milligrams of two (triphenylphosphine) palladium chlorides, under nitrogen protection, add 15 milliliters of dry toluenes, heating reflux reaction two days.Reaction is cooled to room temperature after finishing, and pours in 100 ml waters, with dichloromethane extraction and use anhydrous magnesium sulfate drying organic phase, removes solvent after separated, with silica gel chromatographic column separation and with ethyl alcohol recrystallization purification, obtains yellow solid.Warp
1hNMR,
13cNMR, and elementary analysis test is indicated as target product 4, two (the 4-(2-decyl myristyl) thiophene-2-yls of 7-)-5, the fluoro-diazosulfide of 6-bis-.
Again to prepare two (the 4-(2-hexyl decyl) thiophene-2-yls of 4,7-)-5, the fluoro-diazosulfide of 6-bis-is that example is explained.In two mouthfuls of flasks of 50 milliliters, add 5; 6-bis-fluoro-4; 1.00 mMs of 7-dibromo diazosulfides; tributyl-(4-(2-hexyl decyl) thiophene-2-yl) alkane tin is 3.00 mMs; logical nitrogen 30 minutes; then add 268 milligrams of two (triphenylphosphine) palladium chlorides, under nitrogen protection, add 15 milliliters of dry toluenes, heating reflux reaction two days.Reaction is cooled to room temperature after finishing, and pours in 100 ml waters, with dichloromethane extraction and use anhydrous magnesium sulfate drying organic phase, removes solvent after separated, with silica gel chromatographic column separation and with ethyl alcohol recrystallization purification, obtains yellow solid.Warp
1hNMR,
13cNMR, and elementary analysis test is indicated as target product 4, two (the 4-(2-hexyl decyl) thiophene-2-yls of 7-)-5, the fluoro-diazosulfide of 6-bis-.
To prepare two (the 4-dodecyl thiophene-2-yls)-5 of 4,7-, the fluoro-diazosulfide of 6-bis-is that example is explained again.In two mouthfuls of flasks of 50 milliliters, add 5; 6-bis-fluoro-4; 1.00 mMs of 7-dibromo diazosulfides; tributyl-3.00 mMs, (4-dodecyl thiophene-2-yl) alkane tin; logical nitrogen 30 minutes; then add 268 milligrams of two (triphenylphosphine) palladium chlorides, under nitrogen protection, add 15 milliliters of dry toluenes, heating reflux reaction two days.Reaction is cooled to room temperature after finishing, and pours in 100 ml waters, with dichloromethane extraction and use anhydrous magnesium sulfate drying organic phase, removes solvent after separated, with silica gel chromatographic column separation and with ethyl alcohol recrystallization purification, obtains yellow solid.Warp
1hNMR,
13cNMR, and elementary analysis test is indicated as target product 4, two (the 4-dodecyl thiophene-2-yls)-5 of 7-, the fluoro-diazosulfide of 6-bis-.
Two (the 4-alkylthrophene-2-yls)-5 of 4,7-, the alkyl in the fluoro-diazosulfide of 6-bis-also comprises: methyl, ethyl, positive n-hexyl, 2-ethylhexyl, 1-octyl group nonyl etc., but be not limited only to this.
Embodiment 4:
Two (the bromo-4-of 5-alkylthrophene-2 bases)-5 of 4,7-, the preparation of 6-bis-fluoro-diazosulfides, reaction equation is as follows:
To prepare two (the bromo-4-(2-decyl of the 5-myristyl) thiophene-2-yls of 4,7-)-5, the fluoro-diazosulfide of 6-bis-is that example is explained.In the single port bottle of 50 milliliters, add 4, two (the 4-(2-decyl myristyl) thiophene-2-yls of 7-)-5, (808 milligrams of the fluoro-diazosulfides of 6-bis-, 0.80 mM) and 15 milliliters of oxolanes, under fully stirring, add (315 milligrams of bromo-succinimides (NBS), 1.76 mMs), under room temperature, lucifuge reaction is 24 hours.After reaction finishes, reaction solution is added to the water, with dichloromethane extraction, organic phase is used saturated aqueous common salt and washing, anhydrous sodium sulfate drying continuously, is spin-dried for solvent and through obtain orange red solid with ethyl alcohol recrystallization.Warp
1hNMR,
13cNMR, and elementary analysis test is indicated as target product 4, two (the bromo-4-(2-decyl of the 5-myristyl) thiophene-2-yls of 7-)-5, the fluoro-diazosulfide of 6-bis-.
Two (the bromo-4-alkylthrophene-2-of the 5-yls)-5 of 4,7-, the alkyl in the fluoro-diazosulfide of 6-bis-also comprises: methyl, ethyl, n-hexyl, 2-ethylhexyl, dodecyl, 1-octyl group nonyl, 2-hexyl decyl etc., but be not limited only to this.
Embodiment 5:
The preparation of polymer 1, reaction equation is as follows:
Under argon gas atmosphere, to 50 milliliters of two mouthfuls of flasks, add 4, two (the bromo-4-(2-decyl of the 5-myristyl) thiophene-2-yls of 7-)-5, the fluoro-diazosulfide of 6-bis-and 2, each 0.20 mM, two (the tin trimethyl)-thiophene of 5-, 12 milligrams of 6 milligrams of three (dibenzalacetone) two palladiums and tri-o-tolyl phosphines, be dissolved in 8 milliliters of meta-xylenes, add under hot reflux stirring reaction 72 hours.After cooling, with methyl alcohol sedimentation, go out polymer, dried product is used methyl alcohol, ethyl acetate and chloroform extracting successively, the concentrated and sedimentation in methyl alcohol by chloroformic solution, and end product is the dry darkviolet polymer 1 that obtains under vacuum.The number-average molecular weight of resulting polymers is 24000, and weight average molecular weight is 33000.
Embodiment 6:
The preparation of polymer 2, reaction equation is as follows:
Method is with embodiment 5.With 5,5 '-bis-(tin trimethyl)-2,2 '-bithiophene replaces two (the tin trimethyl)-thiophene of 2,5-.The number-average molecular weight of gained black polymer is 25000, and weight average molecular weight is 36000.There is UV absworption peak at 692nm in thin polymer film, absorbs cut-off limit at 743nm.
The manufacture method of light-emitting diode of the present invention comprises the steps:
Preparing substrate 1, for the ease of the device performance parameter relatively making, substrate dimension is identical, it is 15 millimeters * 15 millimeters, square resistance is about 20 ohm/, use successively acetone, micron order semiconductor special purpose detergent, deionized water, the ultrasonic processing of isopropyl alcohol 10 minutes, clean anode substrate surface, puts into subsequently at 80 ℃ of constant temperature ovens and dries for standing 4 hours.
Prepare anode 2, the anode of light-emitting diode adopts tin indium oxide, utilizes vacuum sputtering to cover above substrate.Anode substrate after oven dry is removed the organic deposit film of anode substrate surface attachment for 10 minutes with plasma bombardment with oxygen plasma etch instrument, and improve the work function of anode surface.
Prepare hole transmission layer 5, anode substrate after drying is removed to the organic deposit film of anode substrate surface attachment for 10 minutes with plasma bombardment with oxygen plasma etch instrument, and improve the work function of anode surface, be placed on the hole transmission layer PEDOT:PSS aqueous solution (concentration approximately 1%, purchased from Bayer company) of upper high speed spin coating one deck approximately 40 nanometer thickness of sol evenning machine (KW-4A type).Thickness is controlled by concentration and the spin coating rotating speed of solution.After film forming, anode substrate is proceeded in constant-temperature vacuum baking oven and dry at 80 ℃, remove residual solvent, post bake.
In addition, also can select Polyvinyl carbazole PVK as the material of hole transmission layer.PVK solid is placed in to clean bottle, proceeds to nitrogen film forming special gloves case, add chlorobenzene to be made into 1% solution, be placed on mixing platform and stir, with 0.45 micron of membrane filtration, obtain clear filtrate.
Prepare polymer light-emitting layer 3, conventionally adopt the methods such as spin coating, printing to be formed on anode surface on the polymer light-emitting layer that adopts said method of the present invention to prepare.Polymer light-emitting layer adopts above-mentioned polymeric material of the present invention.Polymer light-emitting polymer is placed in clean bottle, proceeds to nitrogen film forming special gloves case, by dissolution with solvents, is mixed with solution, is placed on mixing platform and stirs, and with 0.45 micron of membrane filtration, obtains clear filtrate.Deposited polymer luminescent layer in the nitrogen protection film forming special gloves case of anhydrous and oxygen-free, is adsorbed on high-speed rotary painting on sol evenning machine by anode substrate and makes, and thickness is by regulating the rotating speed of sol evenning machine to control.The optimum thickness of polymer light-emitting layer is 70～90 nanometers, by surface profiler actual measurement monitoring.
Prepare negative electrode 4, negative electrode be generally utilize vacuum evaporation by metal evaporation on the surface of polymer light-emitting layer.Above-mentioned device is put into respective metal electrode on the method evaporation that vacuum coating equipment utilizes conventional vacuum evaporation, and plating chamber vacuum degree is 3 * 10
-4below pa, plated film speed and each layer of metal electrode film thickness are monitored in real time by quartz vibrator film thickness monitor.Adopt the method evaporation Ag metallic film of vacuum evaporation to make negative electrode.Also can make negative electrode by evaporation Ba/Al metallic film.
Another method of making negative electrode is on the film of polymer light-emitting layer, evenly to apply one deck conducting resinl, and 2 hours accelerated solidification of 60 ℃ of heating, preferably apply Ag conducting resinl as negative electrode.
Light-emitting diode of the present invention compared with prior art has following beneficial effect:
(1) adopt the above-mentioned polymer light-emitting layer of the present invention as efficient light emitting polymer, make this light-emitting diode there is high energy conversion efficiency, there is high carrier mobility.
(2) preparation technology is simple, and cost of manufacture is low.In prior art, the negative electrode of Organic Light Emitting Diode is made and must under high vacuum, be carried out, be through vacuumizing, the complex process of evaporation or sputter.And adopt polymer light-emitting layer of the present invention, only need to be on polymer light-emitting layer surface even coated with conductive glue, after solidifying, can make device, polymer light-emitting device and display screen manufacture craft are simplified greatly, cost.
(3) be suitable for preparing the negative electrode of flexible display screen.The negative electrode of conventional Organic Light Emitting Diode is owing to being metallic film, when significantly crooked, may cause component failure because of cathodic disbonding.And in one embodiment of the present of invention, use be conducting resinl as cathode material, matrix is polymer adhesive, has suitable adhesion strength and toughness after solidifying, also can strong bonded in bending significantly, thereby be applicable to make the negative electrode of flexible display screen.
Certainly; the present invention also can have other various embodiments; in the situation that not deviating from spirit of the present invention and essence thereof; those of ordinary skill in the art are when making according to the present invention various corresponding changes and distortion, but these corresponding changes and distortion all should belong to the protection range of the appended claim of the present invention.
Claims (6)
1. a polymer LED, comprises substrate, anode, hole transmission layer, polymer light-emitting layer and negative electrode, it is characterized in that,
The material of described polymer light-emitting layer is the conjugated polymer with the diazosulfide of general formula (I) structure,
Wherein, R
1for hydrogen or C
1～C
36alkyl; R
2for hydrogen or C
1～C
36alkyl; Ar is that thiophene, alkylated substituted thiazoline fen, alkoxyl substituted thiophene, bithiophene, alkyl replace bithiophene, alkoxyl and replace a kind of in bithiophene; N=3～1000.
2. polymer LED as claimed in claim 1, is characterized in that, described substrate can be hard substrate or flexible substrate.
3. polymer LED as claimed in claim 1, is characterized in that, hard substrate preferred glass, pottery, metal etc.; The preferred polyethylene terephthalate of flexible substrate, polymethyl methacrylate etc.
4. polymer LED as claimed in claim 1, is characterized in that, described anode is preferably tin indium oxide.
5. polymer LED as claimed in claim 1, is characterized in that, described negative electrode is preferably Ag conducting resinl, can be also Ag film or Ba/Al film.
6. polymer LED as claimed in claim 1, is characterized in that, described hole transmission layer is PEDOT or Polyvinyl carbazole.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107057044A (en) * | 2017-03-03 | 2017-08-18 | 南方科技大学 | A kind of diazosulfide base polymer donor material of exotic atom substitution and its preparation method and application |
| CN107840944A (en) * | 2017-11-22 | 2018-03-27 | 华南理工大学 | It is a kind of using difluoro-benzene and thiadiazoles and four thiophene of connection as random copolymer of main chain and preparation method and application |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1719637A (en) * | 2005-07-15 | 2006-01-11 | 华南理工大学 | Method for making cathode of organic/polymer LED |
| CN101516962A (en) * | 2006-07-31 | 2009-08-26 | 住友化学株式会社 | Polymer compound and polymer light-emitting device using the same |
| CN102076729A (en) * | 2008-08-29 | 2011-05-25 | 默克专利有限公司 | Electroluminescent polymers, method for the production thereof, and use thereof |
| US20120232237A1 (en) * | 2009-11-18 | 2012-09-13 | Zhao Li | Fluorinated Monomers, Oligomers and Polymers for Use in Organic Electronic Devices |
| CN102816297A (en) * | 2011-06-09 | 2012-12-12 | 中国科学院化学研究所 | Polymer based on biphenyl thiadiazole, and preparation method and application thereof |
| CN103030790A (en) * | 2012-12-14 | 2013-04-10 | 华南理工大学 | Conjugated polymer containing fluorobenzothiadiazole and preparation method and application thereof |
| CN103059271A (en) * | 2012-12-20 | 2013-04-24 | 华南理工大学 | Conjugated polymer containing 5,10-diketone-4,9-diazapyrene and preparation thereof |
-
2013
- 2013-10-26 CN CN201310510887.4A patent/CN103606631A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1719637A (en) * | 2005-07-15 | 2006-01-11 | 华南理工大学 | Method for making cathode of organic/polymer LED |
| CN101516962A (en) * | 2006-07-31 | 2009-08-26 | 住友化学株式会社 | Polymer compound and polymer light-emitting device using the same |
| CN102076729A (en) * | 2008-08-29 | 2011-05-25 | 默克专利有限公司 | Electroluminescent polymers, method for the production thereof, and use thereof |
| US20120232237A1 (en) * | 2009-11-18 | 2012-09-13 | Zhao Li | Fluorinated Monomers, Oligomers and Polymers for Use in Organic Electronic Devices |
| CN102816297A (en) * | 2011-06-09 | 2012-12-12 | 中国科学院化学研究所 | Polymer based on biphenyl thiadiazole, and preparation method and application thereof |
| CN103030790A (en) * | 2012-12-14 | 2013-04-10 | 华南理工大学 | Conjugated polymer containing fluorobenzothiadiazole and preparation method and application thereof |
| CN103059271A (en) * | 2012-12-20 | 2013-04-24 | 华南理工大学 | Conjugated polymer containing 5,10-diketone-4,9-diazapyrene and preparation thereof |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107057044A (en) * | 2017-03-03 | 2017-08-18 | 南方科技大学 | A kind of diazosulfide base polymer donor material of exotic atom substitution and its preparation method and application |
| CN107840944A (en) * | 2017-11-22 | 2018-03-27 | 华南理工大学 | It is a kind of using difluoro-benzene and thiadiazoles and four thiophene of connection as random copolymer of main chain and preparation method and application |
| CN107840944B (en) * | 2017-11-22 | 2020-05-22 | 华南理工大学 | Random copolymer with difluoro benzothiadiazole and bitetrathiophene as main chains and preparation method and application thereof |
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Application publication date: 20140226 |