CN104177593A - Quinoxalinyl-containing polymer and preparation method thereof and organic solar energy cell device - Google Patents
Quinoxalinyl-containing polymer and preparation method thereof and organic solar energy cell device Download PDFInfo
- Publication number
- CN104177593A CN104177593A CN201310204078.0A CN201310204078A CN104177593A CN 104177593 A CN104177593 A CN 104177593A CN 201310204078 A CN201310204078 A CN 201310204078A CN 104177593 A CN104177593 A CN 104177593A
- Authority
- CN
- China
- Prior art keywords
- quinoxalinyl
- polymkeric substance
- preparation
- solution
- organic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 0 CC(C)(*)C(C)(C)OBc(cc1)cc2c1c(ccc(B1OC(C)(C)C(C)(C)O1)c1)c1[n]2* Chemical compound CC(C)(*)C(C)(C)OBc(cc1)cc2c1c(ccc(B1OC(C)(C)C(C)(C)O1)c1)c1[n]2* 0.000 description 2
Abstract
The invention belongs to the field of organic semiconductor materials, and discloses a quinoxalinyl-containing polymer and a preparation method thereof and an organic solar energy cell device; the polymer has the following structural formula shown in the specification, R1 and R2 are C1-C20 alkyl, and n is an integer between 15-100. The quinoxalinyl-containing polymer belongs to a donor-receptor conjugated polymer, has high hole mobility, high open circuit voltage, excellent solubility and film-forming performance, has a wide absorption range in the 350nm-700nm range, and further solves the problem of low efficiency of solar cell devices.
Description
Technical field
The present invention relates to organic semiconductor material field, relate in particular to a kind of polymkeric substance containing quinoxalinyl and preparation method thereof.The invention still further relates to and use the polymkeric substance that contains quinoxalinyl as the organic solar batteries device of active coating electron donor material.
Background technology
Utilize cheap material to prepare low cost, dynamical solar cell is study hotspot and the difficult point in photovoltaic field always.Organic semiconductor material with its raw material be easy to get, cheap, technique is simple, stability is strong, photovoltaic effect is good etc., and advantage receives much concern.From N.S.Sariciftci in 1992 etc. at SCIENCE(N.S Sariciftci, L.Smilowitz, A.J.Heeger, et al.Science, 1992,258,1474) upper report conjugated polymers and C
60between Photoinduced Electron transfer phenomena after, organic polymer solar cell becomes the focus of research gradually.The research of this respect has in recent years obtained development at full speed, but organic polymer solar cell is still much lower than the efficiency of conversion of inorganic solar cell.For organic polymer solar cell is on the actual application, the type material that exploitation has a higher-energy efficiency of conversion is still the top priority in this field.
Summary of the invention
The polymkeric substance containing quinoxalinyl that provides a kind of effciency of energy transfer higher is provided problem to be solved by this invention.
Technical scheme of the present invention is as follows:
Containing a polymkeric substance for quinoxalinyl, its structural formula is as follows:
In formula, R
1, R
2be C
1～C
20alkyl, integer between n is 15-100.
The present invention also provides the preparation method of the above-mentioned polymkeric substance containing quinoxalinyl, comprises the steps:
The compd A and the B that provide respectively following structural formula to represent,
wherein, R
1, R
2be 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, obtain following structural formula containing quinoxalinyl polymkeric substance:
in formula, the integer that n is 15-100.
The preparation method of the described polymkeric substance containing quinoxalinyl, wherein, oxygen-free environment is made up of one or both in argon gas, nitrogen.
The preparation method of the described polymkeric substance containing quinoxalinyl, 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 described polymkeric substance containing quinoxalinyl, 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 described polymkeric substance containing quinoxalinyl, wherein, described organic solvent is at least one in toluene, DMF, tetrahydrofuran (THF).
The preparation method of the described polymkeric substance containing quinoxalinyl, wherein, Suzuki coupling reaction temperature is 90～120 DEG C, the reaction times is 24～72 hours.
The preparation method of the described polymkeric substance containing quinoxalinyl, 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 described containing quinoxalinyl polymkeric substance.
The invention still further relates to a kind of organic solar batteries device, the electron donor material of its active coating adopts the polymkeric substance containing quinoxalinyl of following structural formula:
In formula, R
1, R
2be C
1～C
20alkyl, integer between n is 15-100.
Polymkeric substance containing quinoxalinyl of the present invention, for solar cell material, belong to donor-receiver type conjugated polymers, it has higher hole mobility, high open circuit voltage, solubility property and film forming properties have wider absorption region within the scope of 350nm～700nm preferably, and then solve solar cell device low efficiency problem.
The preparation method of the polymkeric substance of above-mentioned quinoxalinyl, 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 polymkeric substance ultraviolet-visible absorption spectroscopy figure containing quinoxalinyl of embodiment 1;
Fig. 2 is the structural representation of the organic solar batteries 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 containing quinoxalinyl of the present embodiment, i.e. poly-{ 2,7-, bis-bases-N-octane base carbazole-co-5,8-bis-base-2,3-di-n-octyl quinoxaline }, (wherein, R
1for octane base, R
2for octane base, n=82), 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 2,7-hypoboric acid pinacol ester-9-octane base carbazole (106mg, 0.2mmol), 5,8-bis-bromo-2,3-di-n-octyl quinoxaline (102mg, 0.2mmol) adds 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 the lower 50 DEG C of dry 24h of vacuum, obtain product, i.e. poly-{ 2,7-, bis-bases-N-octane base carbazole-co-5,8-bis-base-2,3-di-n-octyl quinoxaline }, productive rate 87%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=42.4kDa, M
w/ M
n=2.1.
Fig. 1 is polymkeric substance (P1) the ultraviolet-visible absorption spectroscopy figure containing quinoxalinyl of embodiment 1.As shown in Figure 1, this polymkeric substance has large wider absorption between 350nm～700nm, and wherein maximum absorption band is positioned at 576nm left and right.
Embodiment 2:
The polymkeric substance containing quinoxalinyl of the present embodiment, i.e. poly-{ 2,7-, bis-bases-N-methyl carbazole-co-5,8-bis-base-2,3-bis-NSC 62789 base quinoxalines }, (wherein, R
1for methyl, R
2for NSC 62789 base, n=22), 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 2; 7-hypoboric acid pinacol ester-9-methyl carbazole (130mg; 0.3mmol), 5; 8-bis-bromo-2; 3-bis-NSC 62789 base quinoxaline (255mg; 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, i.e. poly-{ 2,7-, bis-bases-N-methyl carbazole-co-5,8-bis-base-2,3-bis-NSC 62789 base quinoxalines }.Productive rate is 80%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=19.5kDa, M
w/ M
n=2.3.
Embodiment 3:
The polymkeric substance containing quinoxalinyl of the present embodiment, i.e. poly-{ 2,7-, bis-bases-N-NSC 62789 base carbazole-co-5,8-bis-base-2,3-dimethyl quinoxaline }, (wherein, R
1for NSC 62789 base, R
2for methyl, n=47), 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 2,7-hypoboric acid pinacol ester-9-NSC 62789 base carbazole (210mg, 0.3mmol), 5,8-bis-bromo-2,3-dimethyl quinoxaline (104mg, 0.33mmol), palladium (3.5mg, 0.015mmol) He three (o-methoxyphenyl) phosphine (21mg, 0.06mmol) join in the flask of the DMF that fills 12mL, after fully dissolving, add salt of wormwood (3mL, 2mol/L) solution leads to after the about 30min of nitrogen purge gas subsequently in flask; 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, obtain product, i.e. poly-{ 2,7-, bis-bases-N-NSC 62789 base carbazole-co-5,8-bis-base-2,3-dimethyl quinoxaline }, productive rate is 89%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=31.8kDa, M
w/ M
n=2.2.
Embodiment 4:
The polymkeric substance containing quinoxalinyl of the present embodiment, i.e. poly-{ 2,7-, bis-bases-N-normal-butyl carbazole-co-5,8-bis-base-2, the positive decyl quinoxaline of 3-bis-}, (wherein, R
1for normal-butyl, R
2for positive decyl, n=100), 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 2; 7-hypoboric acid pinacol ester-9-normal-butyl carbazole (143mg; 0.3mmol), 5; 8-bis-bromo-2; the positive decyl quinoxaline (160mg of 3-bis-; 0.35mmol), three or two argon benzyl acetone two palladium (9mg; 0.009mmol) with 2-dicyclohexyl phosphine-2 '; 6 '-dimethoxy-biphenyl (29mg, 0.072mmol) joins in the flask of the DMF that fills 12mL; 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, obtain product, i.e. poly-{ 2,7-, bis-bases-N-normal-butyl carbazole-co-5,8-bis-base-2, the positive decyl quinoxaline of 3-bis-}, productive rate is 84%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=63.2kDa, M
w/ M
n=2.0.
Embodiment 5:
The polymkeric substance containing quinoxalinyl of the present embodiment, i.e. poly-{ 2,7-, bis-bases-N-dodecyl carbazole-co-5,8-bis-base-2,3-di-n-hexyl quinoxaline }, (wherein, R
1for dodecyl, R
2for n-hexyl, n=15), 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 2; 7-hypoboric acid pinacol ester-9-dodecyl carbazole (226mg; 0.3mmol), 5; 8-bis-bromo-2; 3-di-n-hexyl quinoxaline (205mg; 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, then add 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, i.e. poly-{ 2,7-, bis-bases-N-dodecyl carbazole-co-5,8-bis-base-2,3-di-n-hexyl quinoxaline }.Productive rate is 73%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=12.6kDa, M
w/ M
n=2.4.
Embodiment 6:
Refer to Fig. 2, a kind of organic solar batteries device 60 comprises substrate 61, anode 62, buffer layer 63, active coating 64 and negative electrode 65.Anode 62, buffer layer 63, active coating 64 and negative electrode 65 stack gradually a surface that is formed at substrate 61.
In the present embodiment, substrate 61 is glass.
Anode 62 is formed at a side surface of substrate 61.In the present embodiment, anode 62 is ITO(tin indium oxide), preferably, ITO is that square resistance is the tin indium oxide of 10-20 Ω/mouth.
Buffer layer 63 is formed at the side surface of anode 62 away from substrate 61.What the material of buffer layer 63 was poly-3,4-ethylenedioxy thiazole (PEDOT) and polystyrene-sulfonic acid matrix material (PSS) mixes, and is expressed as PEDOT:PSS.
Active coating 64 is formed at the side surface of buffer layer 63 away from anode 62.Active coating 64 comprises electron donor material and electron acceptor material, and the mol ratio of electron donor material and electron acceptor material is 1:2, and wherein electron acceptor material is (6,6) phenyl-C
61-methyl-butyrate (PCBM), electron donor material be the present invention prepare containing quinoxalinyl polymkeric substance; In present embodiment, in the embodiment 1 that electron donor material is preparation containing the polymkeric substance of quinoxalinyl, i.e. poly-{ 2,7-, bis-bases-N-octane base carbazole-co-5,8-bis-base-2,3-di-n-octyl quinoxaline } (representing with P1).
Negative electrode 65 is formed at the side surface of active coating 64 away from buffer layer 63.Negative electrode 65 can adopt aluminium electrode or double-metal layer electrode, such as Ca/Al or Ba/Al etc., and its thickness is preferably 170nm, 150nm, 130nm or 100nm.In present embodiment, the material of negative electrode 65 is aluminium, and thickness is 170nm.
In another embodiment, buffer layer 63 can omit, and now active coating 64 is directly formed at anode 62 surfaces.
In the present embodiment 6, the manufacturing processed of this organic solar batteries device 60 is as follows:
After anode 62 being formed to a side surface of substrate 61, carry out ultrasonic cleaning, and after processing with oxygen-Plasma, be coated with the PEDOT:PSS that last layers play modification on anode 62 surfaces and form buffer layer 63.
On buffer layer 64, apply one deck active coating 64.This active coating 64 comprises electron donor material and electron acceptor material, and wherein electron acceptor material is PCBM, the P1 of preparation in the embodiment 1 that electron donor material is.
Form negative electrode 65 on active coating 64 surfaces.In present embodiment, the aluminium lamination of negative electrode 65 for being formed by vacuum evaporation.The thickness of negative electrode 65 is 170nm.
In the present embodiment, this organic solar batteries device 60 was through lower 4 hours of 110 degrees Celsius of air tight conditions, drop to again room temperature, after organic solar batteries device is annealed, can effectively increase order and the regularity between the interior each group of molecule and molecule segment, arranged, improve transmission speed and the efficiency of carrier mobility, improve photoelectric transformation efficiency.
At AM1.5G100mW/cm
2under illumination, the effciency of energy transfer 3.1% of the body heterojunction organic solar batteries device 60 that the copolymer p 1 based in embodiment 1 is donor material.
When this organic solar batteries device 60 uses, under illumination, light transmission substrate 61 and anode 62, the conduction hole type electroluminescent material in active coating 64 absorbs luminous energy, and produces exciton, these excitons move to the interface of electron donor(ED)/acceptor material again, and by transfer transport to electron acceptor material, as PCBM, realize the separation of electric charge, thereby form current carrier freely, i.e. electronics and hole freely.These freely electronics transmit along electron acceptor material to negative electrode 65 and be collected by negative electrode, transmit and collected by anode 62 along electron donor material anode 62 in hole freely, thereby form photoelectric current and photovoltage, realizes opto-electronic conversion, when external load, can power to it.In this process, conduction hole type electroluminescent material, because it has very wide spectral response range, can utilize luminous energy more fully, to obtain higher photoelectric transformation efficiency, increases the electricity generation ability of solar cell device.And this organic materials can also alleviate the quality of solar cell device, and can make by technology such as spin coatings, be convenient to large batch of preparation.
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. containing a polymkeric substance for quinoxalinyl, it is characterized in that, its structural formula is as follows:
In formula, R
1, R
2be C
1～C
20alkyl, integer between n is 15-100.
2. the polymkeric substance containing quinoxalinyl according to claim 2, is characterized in that, comprises the one in following polymkeric substance:
3. a preparation method who contains the polymkeric substance of quinoxalinyl, is characterized in that, comprises the steps:
The compd A and the B that provide respectively following structural formula to represent,
wherein, R
1, R
2be 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, obtain following structural formula containing quinoxalinyl polymkeric substance:
in formula, the integer that n is 15-100.
4. the preparation method of the polymkeric substance containing quinoxalinyl 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 containing quinoxalinyl 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 containing quinoxalinyl 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 containing quinoxalinyl 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 containing quinoxalinyl 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 containing quinoxalinyl 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 described containing quinoxalinyl polymkeric substance.
10. an organic solar batteries device, is characterized in that, the electron donor material of its active coating adopts the polymkeric substance containing quinoxalinyl of following structural formula:
In formula, R
1, R
2be C
1～C
20alkyl, integer between n is 15-100.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310204078.0A CN104177593A (en) | 2013-05-28 | 2013-05-28 | Quinoxalinyl-containing polymer and preparation method thereof and organic solar energy cell device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310204078.0A CN104177593A (en) | 2013-05-28 | 2013-05-28 | Quinoxalinyl-containing polymer and preparation method thereof and organic solar energy cell device |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104177593A true CN104177593A (en) | 2014-12-03 |
Family
ID=51958956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310204078.0A Pending CN104177593A (en) | 2013-05-28 | 2013-05-28 | Quinoxalinyl-containing polymer and preparation method thereof and organic solar energy cell device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104177593A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011085004A2 (en) * | 2010-01-05 | 2011-07-14 | Konarka Technologies, Inc. | Photovoltaic cell with benzodithiophene-containing polymer |
| CN102164926A (en) * | 2008-09-29 | 2011-08-24 | 加利福尼亚大学董事会 | Active materials for photoelectric devices |
-
2013
- 2013-05-28 CN CN201310204078.0A patent/CN104177593A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102164926A (en) * | 2008-09-29 | 2011-08-24 | 加利福尼亚大学董事会 | Active materials for photoelectric devices |
| WO2011085004A2 (en) * | 2010-01-05 | 2011-07-14 | Konarka Technologies, Inc. | Photovoltaic cell with benzodithiophene-containing polymer |
Non-Patent Citations (3)
| Title |
|---|
| ADAM J. MOULE ET AL.: ""Two Novel Cyclopentadithiophene-Based Alternating Copolymers as Potential Donor Components for High-Efficiency Bulk-Heterojunction-Type Solar Cells"", 《CHEM. MATER.》, vol. 20, 21 May 2008 (2008-05-21), pages 4045 - 4050, XP002541043, DOI: doi:10.1021/cm8006638 * |
| MARIA JONFORSEN ET AL.: ""Synthesis and characterization of poly(quinoxaline vinylene)s and poly(pyridopyrazine vinylene)s with phenyl substituted side-groups"", 《SYNTHETIC METALS》, vol. 131, 31 December 2002 (2002-12-31), pages 53 - 59 * |
| NICOLAS BLOUIN ET AL.: ""A Low-Bandgap Poly(2,7-Carbazole) Derivative for Use in High-Performance Solar Cells"", 《ADVANCED MATERIALS》, vol. 19, 31 December 2007 (2007-12-31), pages 2295 - 2300, XP055079645, DOI: doi:10.1002/adma.200602496 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104592493A (en) | 1,2-dithienylethene copolymer solar cell materials, preparing method thereof and applications of the materials | |
| CN104513370A (en) | Diketopyrrolo pyrrole based copolymer, preparation method, and applications thereof | |
| CN104725609A (en) | Dithienylbenzotrithienyl polymer and preparation method and application thereof | |
| CN104177600A (en) | Polymer containing dithiazolebenzothiadiazole group, preparation method and organic solar cell device thereof | |
| CN104592497A (en) | Dithienylethylene-based copolymer solar battery material, and preparation method and application thereof | |
| CN104017187A (en) | Isoindigo group-containing polymer as well as preparation method and application thereof | |
| CN104558538A (en) | Triphenylamine side chain-containing polymer, preparation method thereof and organic solar cell device | |
| CN104592495A (en) | Quinoxaline-group-containing polymers, preparing method thereof and organic solar cell devices | |
| CN104292429A (en) | Anthraquinonyl-containing polymer, preparation method thereof and organic solar cell device | |
| CN104250371A (en) | Carbazolyl-containing polymer and preparation method thereof and organic solar energy cell device | |
| CN104725610A (en) | Dithienylbenzotrithienyl polymer and preparation method and application thereof | |
| CN104513369A (en) | Quinoxaline based copolymer, preparation method and applications thereof | |
| CN104292432A (en) | Polymer containing difluorobenzotriazole unit, and preparation method and application thereof | |
| CN104558536A (en) | Triphenylamine side chain-containing polymer, preparation method thereof and organic solar cell device | |
| CN104017182A (en) | Benzothiadiazolyl containing polymer and preparation method and application thereof | |
| CN104177593A (en) | Quinoxalinyl-containing polymer and preparation method thereof and organic solar energy cell device | |
| CN104558539A (en) | Dithienyl benzotriazole side chain-containing polymer, preparation method thereof and organic solar cell device | |
| CN104629003A (en) | Isoindigo group containing polymer, preparation method and organic solar cell device | |
| CN104250365A (en) | Anthraquinonyl group-containing polymer, preparation method thereof, and organic solar cell device | |
| CN104177595A (en) | Quinoxalinyl-containing polymer and preparation method thereof and organic solar energy cell device | |
| CN104177601A (en) | Quinoxalinyl polymer, preparation method and organic electroluminescent device thereof | |
| CN104177594A (en) | Benzo dithienyl-containing polymer and preparation method thereof and organic solar energy cell device | |
| CN104177592A (en) | Dithiazole benzo triazolyl-containing polymer and preparation method thereof and organic solar energy cell device | |
| CN104629001A (en) | Thiapyrazinyl-containing polymer and preparation method thereof, and organic solar cell device | |
| CN104629018A (en) | Dithiophene-containing vinyl copolymer as well as preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20141203 |