CN104177594A - Benzo dithienyl-containing polymer and preparation method thereof and organic solar energy cell device - Google Patents

Benzo dithienyl-containing polymer and preparation method thereof and organic solar energy cell device Download PDF

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CN104177594A
CN104177594A CN201310204080.8A CN201310204080A CN104177594A CN 104177594 A CN104177594 A CN 104177594A CN 201310204080 A CN201310204080 A CN 201310204080A CN 104177594 A CN104177594 A CN 104177594A
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polymkeric substance
preparation
benzo dithienyl
dithienyl
substance containing
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周明杰
张振华
王平
冯小明
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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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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

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  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

Abstract

The invention belongs to the field of organic semiconductor materials, discloses a benzo dithienyl-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 14 and 100. The benzo dithienyl-containing polymer has a narrow band gap, high sunlight absorption coefficient and a wide absorption range in the 300nm-700nm range, and further can improve the energy conversion efficiency of solar cell devices.

Description

Containing polymkeric substance of benzo dithienyl and preparation method thereof and organic solar batteries device
Technical field
The present invention relates to organic semiconductor material field, relate in particular to a kind of polymkeric substance containing benzo dithienyl and preparation method thereof.The invention still further relates to use and contain the polymkeric substance of benzo dithienyl as the organic solar batteries device of active coating electron donor material.
Background technology
Utilize cheap material preparation 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 benzo dithienyl 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 benzo dithienyl, its structural formula is as follows:
In formula, R is C 1～C 20alkyl, integer between n is 14-100.
The present invention also provides the preparation method of the above-mentioned polymkeric substance containing benzo dithienyl, 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 dissolve, at 70～130 ℃, carry out Stille coupling reaction 6～60 hours subsequently, stop after coupling reaction, separating-purifying reaction solution, obtain following structural formula containing the polymkeric substance of benzo dithienyl:
in formula, the integer that n is 14-100.
The preparation method of the described polymkeric substance containing benzo dithienyl, wherein, one or both in argon gas, nitrogen of oxygen-free environment form.
The preparation method of the described polymkeric substance containing benzo dithienyl, 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 benzo dithienyl, wherein, described organic solvent is at least one in toluene, DMF, tetrahydrofuran (THF).
The preparation method of the described polymkeric substance containing benzo dithienyl, wherein, Stille coupling reaction temperature is 90～120 ℃, the reaction times is 12～48 hours.
The preparation method of the described polymkeric substance containing benzo dithienyl, wherein, separating-purifying reaction solution comprises:
After coupling reaction, in reaction solution, add methyl alcohol precipitating, by apparatus,Soxhlet's, filter subsequently, using successively again methyl alcohol and normal hexane extracting, obtain organic phase, then take chloroform as solvent extraction organic phase is to colourless, collect chloroformic solution and be spin-dried for, after the lower 50 ℃ of dry 24h of vacuum, obtain the described polymkeric substance containing benzo dithienyl.
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 benzo dithienyl of following structural formula:
In formula, R is C 1～C 20alkyl, integer between n is 14-100.
Of the present invention containing in benzo dithienyl D-A type polymer solar battery material, there is band gap narrower and sunlight is had higher uptake factor and in the wider advantages such as absorption region of 300nm～700nm, can improve solar cell effciency of energy transfer.
The preparation method of the above-mentioned polymkeric substance containing benzo dithienyl, 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.
Accompanying drawing explanation
Fig. 1 is the polymkeric substance ultraviolet-visible absorption spectroscopy figure containing benzo dithienyl 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, below by concrete example and legend, further illustrate technology case of the present invention, 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 benzo dithienyl of the present embodiment, i.e. poly-{ 2,6-, bis-base-4,8-bis-octane oxygen base benzene 1,4-Dithiapentalene-co-6,11-bis-bases-dibenzo [f, h] quinoxaline-2,3-dicyano }, (wherein, R is octane base, and n=38), 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 2,6-bis-(tin trimethyl)-4,8-bis-octane oxygen base benzene 1,4-Dithiapentalene (154mg, 0.2mmol), 6,11-dibromo dibenzo [f, h] quinoxaline-2,3-dicyano (88mg, 0.2mmol) add in the flask that fills 10ml toluene solvant, vacuumize deoxygenation and be filled with argon gas, then add bi triphenyl phosphine dichloride palladium (5.6mg, 0.008mmol); Flask is heated to 100 ℃ and carries out Stille coupling reaction 36h.Subsequently, after cooling, stop polyreaction, to dripping in flask, in 50ml methyl alcohol, carry out sedimentation; After filtering by apparatus,Soxhlet's, use successively methyl alcohol and normal hexane extracting 24h.Then take chloroform as solvent extraction is to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, after the lower 50 ℃ of dry 24h of vacuum, obtain product, gather { 2,6-bis-base-4,8-bis-octane oxygen base benzene 1,4-Dithiapentalene-co-6,11-bis-bases-dibenzo [f, h] quinoxaline-2,3-dicyano }, productive rate 85%.
Test result is: Molecular weight (GPC, THF, R.I): M n=42.6kDa, M w/ M n=2.3.
Fig. 1 is the polymkeric substance ultraviolet-visible absorption spectroscopy figure containing benzo dithienyl of embodiment 1.As shown in Figure 1, this polymkeric substance has large wider absorption between 300nm～700nm, and wherein maximum absorption band is positioned at 614nm left and right.
Embodiment 2:
The polymkeric substance containing benzo dithienyl of the present embodiment, i.e. poly-{ 2,6-, bis-base-4,8-diformazan alkoxyl group benzene 1,4-Dithiapentalene-co-6,11-bis-bases-dibenzo [f, h] quinoxaline-2,3-dicyano }, (wherein, R is methyl, and n=63), 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, 6-bis-(tin trimethyl)-4, 8-diformazan alkoxyl group benzene 1,4-Dithiapentalene (173mg, 0.3mmol), 6, 11-dibromo dibenzo [f, h] quinoxaline-2, 3-dicyano (131mg, 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, again after the about 10min of gas mixture air-discharging of fully logical nitrogen and argon gas, two-mouth bottle is joined to 70 ℃ and carry out Stille coupling reaction 60h.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 the chloroform of take is extremely colourless as solvent extraction, collects chloroformic solution and be spin-dried for to obtain red powder, after collection, under vacuum, after 50 ℃ of dry 24h, obtains product, gather { 2,6-, bis-base-4,8-diformazan alkoxyl group benzene 1,4-Dithiapentalene-co-6,11-bis-bases-dibenzo [f, h] quinoxaline-2,3-dicyano }.Productive rate is 79%.
Test result is: Molecular weight (GPC, THF, R.I): M n=36.7kDa, M w/ M n=2.2.
Embodiment 3:
The polymkeric substance containing benzo dithienyl of the present embodiment, i.e. poly-{ 2,6-, bis-base-4,8-bis-NSC 62789 oxygen base benzene 1,4-Dithiapentalene-co-6,11-bis-bases-dibenzo [f, h] quinoxaline-2,3-dicyano }, (wherein, R is NSC 62789 base, and n=14), 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 2,6-bis-(tin trimethyl)-4,8-bis-NSC 62789 oxygen base benzene 1,4-Dithiapentalene (333mg, 0.3mmol), 6,11-dibromo dibenzo [f, h] quinoxaline-2,3-dicyano (145mg, 0.33mmol), palladium (3.5mg, 0.015mmol) and three (o-methoxyphenyl) phosphine (21mg, 0.06mmol) joins the N that fills 12mL, in the flask of dinethylformamide, in flask, lead to after the about 20min of nitrogen purge gas subsequently; Flask is heated to 130 ℃ and carries out Stille coupling reaction 6h.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 take chloroform as solvent extraction is to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, after collection, under vacuum, after 50 ℃ of dry 24h, obtain product, gather { 2,6-bis-base-4,8-bis-NSC 62789 oxygen base benzene 1,4-Dithiapentalene-co-6,11-bis-bases-dibenzo [f, h] quinoxaline-2,3-dicyano }, productive rate is 76%.
Test result is: Molecular weight (GPC, THF, R.I): M n=13.7kDa, M w/ M n=2.5.
Embodiment 4:
The polymkeric substance containing benzo dithienyl of the present embodiment, i.e. poly-{ 2,6-, bis-base-4,8-bis-normal butane oxygen base benzene 1,4-Dithiapentalene-co-6,11-bis-bases-dibenzo [f, h] quinoxaline-2,3-dicyano }, (wherein, R is normal-butyl, and 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 2,6-bis-(tin trimethyl)-4,8-bis-normal butane oxygen base benzene 1,4-Dithiapentalene (198mg, 0.3mmol), 6,11-dibromo dibenzo [f, h] quinoxaline-2,3-dicyano (158mg, 0.36mmol), three or two argon benzyl acetone two palladiums (9mg, 0.009mmol) and 2-dicyclohexyl phosphines-2 ', 6 '-dimethoxy-biphenyl (29mg, 0.072mmol) join in the flask of the DMF that fills 12mL, in flask, lead to after the about 20min of nitrogen purge gas subsequently; Flask is heated to 120 ℃ and carries out Stille coupling reaction 24h.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 take chloroform as solvent extraction is to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, after collection, under vacuum, after 50 ℃ of dry 24h, obtain product, gather { 2,6-bis-base-4,8-bis-normal butane oxygen base benzene 1,4-Dithiapentalene-co-6,11-bis-bases-dibenzo [f, h] quinoxaline-2,3-dicyano }, productive rate is 83%.
Test result is: Molecular weight (GPC, THF, R.I): M n=60.2kDa, M w/ M n=2.0.
Embodiment 5:
The polymkeric substance containing benzo dithienyl of the present embodiment, i.e. poly-{ 2,6-, bis-base-4,8-bis-n-dodecane oxygen base benzene 1,4-Dithiapentalene-co-6,11-bis-bases-dibenzo [f, h] quinoxaline-2,3-dicyano }, (wherein, R is dodecyl, and n=76), 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, 6-bis-(tin trimethyl)-4, 8-bis-n-dodecane oxygen base benzene 1,4-Dithiapentalene (265mg, 0.3mmol), 6, 11-dibromo dibenzo [f, h] quinoxaline-2, 3-dicyano (158mg, 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, again after the about 10min of gas mixture air-discharging of fully logical nitrogen and argon gas, two-mouth bottle is joined to 90 ℃ and carry out Stille coupling reaction 48h.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 take chloroform as solvent extraction is to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, after collection under vacuum after 50 ℃ of dry 24h, obtain product, i.e. poly-{ 2,6-, bis-base-4,8-bis-n-dodecane oxygen base benzene 1,4-Dithiapentalene-co-6,11-bis-bases-dibenzo [f, h] quinoxaline-2,3-dicyano }.Productive rate is 81%.
Test result is: Molecular weight (GPC, THF, R.I): M n=58.4kDa, M w/ M n=2.1.
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 anode 62 away from a side surface of 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 buffer layer 63 away from a side surface of 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 is the polymkeric substance containing benzo dithienyl prepared by the present invention; In present embodiment, in the embodiment 1 that electron donor material is, the polymkeric substance containing benzo dithienyl of preparation, gathers { 2,6-bis-base-4,8-bis-octane oxygen base benzene 1,4-Dithiapentalene-co-6,11-bis-bases-dibenzo [f, h] quinoxaline-2,3-dicyano } (with P1, representing).
Negative electrode 65 is formed at active coating 64 away from a side surface of 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 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, on anode 62 surfaces, be coated with the PEDOT:PSS that last layers play modification 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.
On active coating 64 surfaces, form negative electrode 65.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 solar cell device is annealed, can effectively increase order and the regularity between 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 3.0% 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 is used, 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 along electron acceptor material to negative electrode 65, transmit 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, during 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 benzo dithienyl, it is characterized in that, its structural formula is as follows:
In formula, R is C 1～C 20alkyl, integer between n is 14-100.
2. the polymkeric substance containing benzo dithienyl according to claim 2, is characterized in that, comprises a kind of in following polymkeric substance:
3. contain a preparation method for the polymkeric substance of benzo dithienyl, it is characterized in that, comprise 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 dissolve, at 70～130 ℃, carry out Stille coupling reaction 6～60 hours subsequently, stop after coupling reaction, separating-purifying reaction solution, obtain following structural formula containing the polymkeric substance of benzo dithienyl:
in formula, the integer that n is 14-100.
4. the preparation method of the polymkeric substance containing benzo dithienyl according to claim 3, is characterized in that, described catalyzer is bi triphenyl phosphine dichloride palladium or tetra-triphenylphosphine palladium; The mol ratio of described catalyzer and described compd A is 1:20～1:100.
5. the preparation method of the polymkeric substance containing benzo dithienyl according to claim 3, is characterized in that, 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.
6. the preparation method of the polymkeric substance containing benzo dithienyl according to claim 5, 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.
7. the preparation method of the polymkeric substance containing benzo dithienyl 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 benzo dithienyl according to claim 3, is characterized in that, Stille coupling reaction temperature is 90～120 ℃, and the reaction times is 12～48 hours.
9. the preparation method of the polymkeric substance containing benzo dithienyl according to claim 3, is characterized in that, separating-purifying reaction solution comprises:
After coupling reaction, in reaction solution, add methyl alcohol precipitating, by apparatus,Soxhlet's, filter subsequently, using successively again methyl alcohol and normal hexane extracting, obtain organic phase, then take chloroform as solvent extraction organic phase is to colourless, collect chloroformic solution and be spin-dried for, after the lower 50 ℃ of dry 24h of vacuum, obtain the described polymkeric substance containing benzo dithienyl.
10. an organic solar batteries device, is characterized in that, the electron donor material of its active coating adopts the polymkeric substance containing benzo dithienyl of following structural formula:
In formula, R is C 1～C 20alkyl, integer between n is 14-100.
CN201310204080.8A 2013-05-28 2013-05-28 Benzo dithienyl-containing polymer and preparation method thereof and organic solar energy cell device Pending CN104177594A (en)

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CN103025788A (en) * 2010-07-09 2013-04-03 默克专利股份有限公司 Semiconducting polymers

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Application publication date: 20141203