CN104558534A - Dithienyl benzotriazole side chain-containing polymer, preparation method thereof and organic solar cell device - Google Patents
Dithienyl benzotriazole side chain-containing polymer, preparation method thereof and organic solar cell device Download PDFInfo
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Abstract
The invention belongs to the field of organic semiconductors and discloses a dithienyl benzotriazole side chain-containing polymer, a preparation method thereof and an organic solar cell device. A main body material has a structural general formula shown in descriptions, wherein each of R1 and R2 is C1-C20 alkyl, and n is an integer between 10 and 100. According to the dithienyl benzotriazole side chain-containing polymer disclosed by the invention, a dithienyl benzotriazole (BTz) side chain is an important electron acceptor unit and is beneficial to the reduction of a band gap of the polymer; cyclopentano-dithiophene (PDT) has easily-modified photophysical properties, and copolymers of PDT show the advantages of relatively high absorption coefficient and relatively wide absorption range to sunlight, and the like; by applying the polymer, which is prepared through copolymerizing BTz and PDT by a Stille coupling method, to solar cells, the efficiency of organic electroluminescent devices can be increased.
Description
Technical field
The present invention relates to organic semiconductor material field, particularly relate to and a kind ofly contain polymkeric substance of two thiophene benzotriazole side chains and preparation method thereof.The invention still further relates to and a kind ofly use this organic solar batteries device of polymkeric substance as active layer electron donor material containing two thiophene benzotriazole side chains.
Background technology
Utilize cheap material prepares low cost, dynamical solar cell is photovoltaic art always study hotspot and difficult point.The advantages such as organic semiconductor material is easy to get with its raw material, cheap, technique is simple, stability is strong, photovoltaic effect is good receive much concern.From N.S.Sariciftci in 1992 etc. at SCIENCE(N.SSariciftci, L.Smilowitz, A.J.Heeger, et al.Science, 1992,258,1474) upper report conjugated polymers and C
60between Photo-induced electron transfer phenomenon after, organic polymer solar cell becomes the focus of research gradually.The research of this respect in recent years achieves development at full speed, but organic polymer solar cell is still much lower than the efficiency of conversion of inorganic solar cell.In order to make organic polymer solar cell be on the actual application, develop the top priority that the type material with higher-energy efficiency of conversion is still this field.
Summary of the invention
Based on the problems referred to above, problem to be solved by this invention is the polymkeric substance containing two thiophene benzotriazole side chains providing a kind of transformation efficiency high.
Technical scheme of the present invention is as follows:
A kind of polymkeric substance containing two thiophene benzotriazole side chains provided by the invention, its general structure is as follows:
In formula, R
1, R
2be C
1~ C
20alkyl, n is the integer of 10 ~ 100
Another object of the embodiment of the present invention is to provide a kind of preparation method containing the polymkeric substance of two thiophene benzotriazole side chains, comprises the steps:
The compd A providing following structural formula to represent respectively and B,
A:
i.e. 2,6-bis-tin trimethyl-4,4-bis-(alkoxyl group) pentamethylene 1,4-Dithiapentalenes;
B:
i.e. 4-(5-(2-(2,5-dibromo thiophene) vinyl) thiophene-2-base)-2-alkyl-7-(thiophene-2-base)-2H-benzo [d] [1,2,3] triazole;
Under oxygen-free environment (oxygen-free environment of at least one gas composition in preferred argon gas, nitrogen), be after dissolving during the compd A of 1:1 ~ 1.2 and B are added into containing catalyzer organic solvent by mol ratio, Stille coupling reaction is carried out 6 ~ 60 hours at 70 ~ 130 DEG C, polyreaction is stopped after cooling, through separating-purifying reaction solution, obtain the described polymkeric substance containing two thiophene benzotriazole side chains of following general structure:
In formula, R
1, R
2be C
1~ C
20alkyl, n is the integer of 10 ~ 100.
Wherein, described catalyzer is described catalyzer is bis-triphenylphosphipalladium palladium dichloride or tetra-triphenylphosphine palladium; Or
Palladium and three (o-methyl-phenyl-) the phosphine mixture of described catalyzer to be mol ratio be 1:4 ~ 8, or mol ratio is three or two argon benzyl acetone two palladiums and the 2-dicyclohexyl phosphine-2 of 1:4 ~ 8 ', 6 '-dimethoxy-biphenyl mixture;
The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
In a preferred embodiment, organic solvent is selected from solvent is at least one in toluene, DMF, tetrahydrofuran (THF).
In a preferred embodiment, Stille coupling reaction temperature is at 90 ~ 120 DEG C, the reaction times is 24 ~ 48 hours.
In a preferred embodiment, separating-purifying reaction solution comprises step:
After reaction stops, methyl alcohol precipitating is added in reaction solution, methyl alcohol and normal hexane extracting is used successively after being filtered by apparatus,Soxhlet's, then be that solvent extraction is to colourless with chloroform, collect chloroformic solution and be spin-dried for and obtain powder, powder after collection, more under vacuo after 50 DEG C of dry 24h, obtains the described polymkeric substance containing two thiophene benzotriazole side chains.
The present invention also provides a kind of organic solar batteries device, and the electron donor material of its active layer adopts the polymkeric substance containing two thiophene benzotriazole side chains of following structural formula:
In formula, R
1, R
2be C
1~ C
20alkyl, n is the integer of 10 ~ 100.
Of the present inventionly contain in the polymkeric substance of two thiophene benzotriazole side chains, two thiophene benzotriazole (BTz) side chains are important electron acceptor(EA) unit, are conducive to reducing polymkeric substance band gap; Pentamethylene 1,4-Dithiapentalene (PDT) has the photophysical property easily modified, and its co-polymer shows has the advantage such as higher uptake factor and wider absorption region to sunlight.The polymer application prepared by the copolymerization of Stille coupling method by BTz and PDT, in solar cell, can improve organic electroluminescence device poor efficiency.
The above-mentioned preparation method containing the polymkeric substance of two thiophene benzotriazole side chains, has used better simply synthetic route, thus reduces technical process, and starting material are cheap and easy to get, and manufacturing cost is reduced; And the polymeric material constructions be worth is novel, solubility property is good, and film forming properties is excellent, and absorption region is wide, and effciency of energy transfer is improved.
Accompanying drawing explanation
Fig. 1 is the ultraviolet-visible absorption spectroscopy figure of the polymkeric substance containing two thiophene benzotriazole side chains that embodiment 1 obtains;
Fig. 2 is the structural representation of the organic solar batteries device that embodiment 6 obtains.
Embodiment
In order to understand the content of patent of the present invention better, technology case of the present invention is further illustrated below by concrete example and legend, specifically comprise material preparation and device preparation, but these embodiments do not limit the present invention, wherein compd A, compd B are all purchased from Taiwan Jiguang Technology Corporation.
Embodiment 1:
The polymkeric substance containing two thiophene benzotriazole side chains of the present embodiment, i.e. poly-{ 2,6-bis-base-4,4-bis-(n-octyl) pentamethylene 1,4-Dithiapentalene-co-4-(5-(2-(2,5-bis-base thiophene) vinyl) thiophene-2-base)-2-n-octyl-7-(thiophene-2-base)-2H-benzo [d] [1,2,3] triazole } (P1), (wherein, R1 is octane base, R2 is octane base, n=57), 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-4,4-bis-(n-octyloxy) pentamethylene 1,4-Dithiapentalene (146mg, 0.2mmol), 4-(5-(2-(2,5-dibromo thiophene) vinyl) thiophene-2-base)-2-n-octyl-7-(thiophene-2-base)-2H-benzo [d] [1,2,3] triazole (132mg, 0.2mmol) add in the flask filling 10ml toluene solvant, vacuumize deoxygenation and be filled with argon gas, then adding bis-triphenylphosphipalladium palladium dichloride (5.6mg, 0.008mmol); Flask is heated to 100 DEG C and carries out Stille coupling reaction 36h.Subsequently, after cooling, stop polyreaction, drip in flask in 50ml methyl alcohol and carry out sedimentation; Methyl alcohol and normal hexane extracting 24h is used successively after being filtered by apparatus,Soxhlet's.Then be that solvent extraction is extremely colourless with chloroform, collect chloroformic solution and be spin-dried for obtain red powder, after collection, 50 DEG C of dry 24h obtain P1 product under vacuo, productive rate 83%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=50.6kDa, M
w/ M
n=2.2.
Fig. 1 is the ultraviolet-visible absorption spectroscopy figure of the polymkeric substance containing two thiophene benzotriazole side chains that embodiment 1 obtains; As shown in Figure 1, this polymkeric substance has comparatively large wider absorption between 300nm ~ 700nm, and wherein maximum absorption band is positioned at about 605nm.
Embodiment 2:
The polymkeric substance containing two thiophene benzotriazole side chains of the present embodiment, i.e. poly-{ 2,6-bis-base-4,4-bis-(methyl) pentamethylene 1,4-Dithiapentalene-co-4-(5-(2-(2,5-bis-base thiophene) vinyl) thiophene-2-base)-2-NSC 62789 base-7-(thiophene-2-base)-2H-benzo [d] [1,2,3] triazole } (P2), (wherein, R1 is methyl, R2 is NSC 62789 base, n=41), 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 argon gas gas mixture are protected, by 2, 6-bis-tin trimethyl-4, 4-dimethylcyclopentane 1,4-Dithiapentalene (218mg, 0.3mmol), 4-(5-(2-(2, 5-dibromo thiophene) vinyl) thiophene-2-base)-2-NSC 62789 base-7-(thiophene-2-base)-2H-benzo [d] [1, 2, 3] triazole (249mg, 0.3mmol) add in the two-mouth bottle of 50mL specification with 15mL tetrahydrofuran (THF), after the gas mixture air-discharging passing into nitrogen and argon gas after abundant dissolving is about 20min, then by tetra-triphenylphosphine palladium (4mg, 0.003mmol) add wherein, after the gas mixture air-discharging of fully logical nitrogen and argon gas is about 10min again, two-mouth bottle is joined 70 DEG C and carry out Stille coupling reaction 60h.Subsequently, after cooling, stop polyreaction, in two-mouth bottle, add 40mL methyl alcohol precipitating, after being filtered by apparatus,Soxhlet's, use methyl alcohol and normal hexane extracting 24h successively.Then be solvent extraction with chloroform to colourless, collect chloroformic solution and be spin-dried for and obtain red solid, after collection, obtain P2 product after 50 DEG C of dry 24h under vacuo.Productive rate is 77%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=34.9kDa, M
w/ M
n=2.3.
Embodiment 3:
The polymkeric substance containing two thiophene benzotriazole side chains of the present embodiment, i.e. poly-{ 2,6-bis-base-4,4-bis-(NSC 62789 base) pentamethylene 1,4-Dithiapentalene-co-4-(5-(2-(2,5-bis-base thiophene) vinyl) thiophene-2-base)-2-methyl-7-(thiophene-2-base)-2H-benzo [d] [1,2,3] triazole } (P3), (wherein, R1 is NSC 62789 base, R2 is methyl, n=10), 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, 4-bis-(NSC 62789 base) pentamethylene 1,4-Dithiapentalene (319mg, 0.3mmol), 4-(5-(2-(2, 5-dibromo thiophene) vinyl) thiophene-2-base)-2-methyl-7-(thiophene-2-base)-2H-benzo [d] [1, 2, 3] triazole (186mg, 0.33mmol), palladium (3.5mg, 0.015mmol) He three (o-methyl-phenyl-) phosphine (21mg, 0.06mmol) join the N filling 12mL, in the flask of dinethylformamide, after in flask, logical nitrogen purge gas is about 20min subsequently, flask is heated to 130 DEG C and carries out Stille coupling reaction 6h.Subsequently, after cooling, stop polyreaction, in flask, add 40mL methyl alcohol precipitating, after being filtered by apparatus,Soxhlet's, use methyl alcohol and normal hexane extracting 24h successively; Then be solvent extraction with chloroform to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, after collection under vacuo after 50 DEG C of dry 24h, be P3 product, productive rate is 80%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=16.2kDa, M
w/ M
n=2.4.
Embodiment 4:
The polymkeric substance containing two thiophene benzotriazole side chains of the present embodiment, i.e. poly-{ 2,6-bis-base-4,4-bis-(normal-butyl) pentamethylene 1,4-Dithiapentalene-co-4-(5-(2-(2,5-bis-base thiophene) vinyl) thiophene-2-base) the positive decyl of-2--7-(thiophene-2-base)-2H-benzo [d] [1,2,3] triazole } (P4), (wherein, R1 is normal-butyl, R2 is 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, 6-bis-tin trimethyl-4, 4-bis-(normal butane base) pentamethylene 1,4-Dithiapentalene (185mg, 0.3mmol), 4-(5-(2-(2, 5-dibromo thiophene) vinyl) thiophene-2-base) the positive decyl of-2--7-(thiophene-2-base)-2H-benzo [d] [1, 2, 3] triazole (248mg, 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 filling 12mL, in the flask of dinethylformamide, after in flask, logical nitrogen purge gas is about 20min subsequently, flask is heated to 120 DEG C and carries out Stille coupling reaction 24h.Subsequently, after cooling, stop polyreaction, in flask, add 40mL methyl alcohol precipitating, after being filtered by apparatus,Soxhlet's, use methyl alcohol and normal hexane extracting 24h successively; Then be solvent extraction with chloroform to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, after collection under vacuo after 50 DEG C of dry 24h, be P4 product, productive rate is 85%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=84.8kDa, M
w/ M
n=2.0.
Embodiment 5:
The polymkeric substance containing two thiophene benzotriazole side chains of the present embodiment, i.e. poly-{ 2,6-bis-base-4,4-bis-(dodecyl) pentamethylene 1,4-Dithiapentalene-co-4-(5-(2-(2,5-bis-base thiophene) vinyl) thiophene-2-base)-2-n-hexyl-7-(thiophene-2-base)-2H-benzo [d] [1,2,3] triazole } (P5), (wherein, R1 is dodecyl, R2 is n-hexyl, n=78), 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 argon gas gas mixture are protected, by 2, 6-bis-tin trimethyl-4, 4-bis-(dodecyl) pentamethylene 1,4-Dithiapentalene (252mg, 0.3mmol), 4-(5-(2-(2, 5-dibromo thiophene) vinyl) thiophene-2-base)-2-n-hexyl-7-(thiophene-2-base)-2H-benzo [d] [1, 2, 3] triazole (190mg, 0.3mmol) add in the two-mouth bottle of 50mL specification with 15mL toluene, after the gas mixture air-discharging passing into nitrogen and argon gas after abundant dissolving is about 20min, then by tetra-triphenylphosphine palladium (8mg, 0.006mmol) add wherein, after the gas mixture air-discharging of fully logical nitrogen and argon gas is about 10min again, two-mouth bottle is joined 90 DEG C and carry out Stille coupling reaction 48h.Subsequently, after cooling, stop polyreaction, in two-mouth bottle, add 40mL methyl alcohol precipitating, after being filtered by apparatus,Soxhlet's, use methyl alcohol and normal hexane extracting 24h successively.Then be solvent extraction with chloroform to colourless, collect chloroformic solution and be spin-dried for and obtain red solid, after collection, obtain P5 product after 50 DEG C of dry 24h under vacuo.Productive rate is 81%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=81.3kDa, M
w/ M
n=2.1.
Embodiment 6:
Refer to Fig. 2, a kind of organic solar batteries device 60, comprise 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 are formed on substrate 61 successively.
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 for being ITO(tin indium oxide), preferably, the tin indium oxide of ITO to be square resistance be 10-20 Ω/.
Buffer layer 63 is formed at the side surface of anode 62 away from substrate 61.The material of buffer layer 63 is poly-3,4-Ethylenedioxy Thiophenes (PEDOT) and the mixture of polystyrene-sulfonic acid matrix material (PSS), 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 is the polymkeric substance containing two thiophene benzotriazole side chains of the present invention, in the present embodiment, electron donor material is poly-{ 2 of preparation in embodiment 1,6-bis-base-4,4-bis-(n-octyl) pentamethylene 1,4-Dithiapentalene-co-4-(5-(2-(2,5-bis-base thiophene) vinyl) thiophene-2-base)-2-n-octyl-7-(thiophene-2-base)-2H-benzo [d] [1,2,3] triazole } (representing with P1), active coating 64 is expressed as P1:PCBM.
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.
Be appreciated that in another embodiment, buffer layer 63 can omit, and now active coating 64 is directly formed at anode 62 surface.
The manufacturing processed of this organic solar batteries 60 is as follows:
Anode 62 is formed at the laggard row ultrasonic cleaning of a side surface of substrate 61, and after processing with oxygen-Plasma, is coated with the PEDOT:PSS formation buffer layer 63 that last layer plays modification on anode 62 surface.
Buffer layer 64 applies 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.
Negative electrode 65 is formed on active coating 64 surface.In present embodiment, negative electrode 65 is the aluminium lamination formed by vacuum evaporation.The thickness of negative electrode 65 is 170nm.
In the present embodiment, this organic solar batteries 60 was through lower 4 hours of 110 degrees Celsius of air tight conditions, drop to room temperature again, the order and regularity that arrange between each group and molecule segment in molecule effectively can be increased after organic solar batteries device is annealed, improve transmission speed and the efficiency of carrier mobility, improve photoelectric transformation efficiency.
At AM1.5G100mW/cm
2under illumination, be the effciency of energy transfer 3.7% of the body heterojunction organic solar batteries 60 of donor material based on the copolymer p 1 in embodiment 1.
When this organic solar batteries device 60 uses, under light illumination, light transmission substrate 61 and anode 62, the conduction hole type solar cell 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, thus form current carrier freely, i.e. electronics and hole freely.These freely electronics to transmit along electron acceptor material to negative electrode 65 and collected by negative electrode, hole to be transmitted and collected by anode 62 along electron donor material anode 62 freely, thus forms photoelectric current and photovoltage, realizes opto-electronic conversion, during external load, can power to it.In the process, conduction hole type solar cell material has very wide spectral response range due to it, can utilize luminous energy more fully, to obtain higher photoelectric transformation efficiency, increases the electricity generation ability of organic solar batteries.And this organic materials can also alleviate the quality of organic solar batteries, and can be made by technology such as spin coatings, be convenient to large batch of preparation.
The above embodiment only have expressed several embodiment of the present invention, and it describes comparatively concrete and detailed, but therefore can not 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.
Should be understood that, the above-mentioned statement for present pre-ferred embodiments is comparatively detailed, and therefore can not think the restriction to scope of patent protection of the present invention, scope of patent protection of the present invention should be as the criterion with claims.
Claims (8)
1., containing a polymkeric substance for two thiophene benzotriazole side chains, it is characterized in that, its general structure is as follows:
In formula, R
1, R
2be C
1~ C
20alkyl, n is the integer of 10 ~ 100.
2., containing a preparation method for the polymkeric substance of two thiophene benzotriazole side chains, it is characterized in that, comprise the steps:
The compd A providing following structural formula to represent respectively and B,
Under oxygen-free environment, be dissolve mol ratio during the compd A of 1:1 ~ 1.2 and B are added into containing catalyzer organic solvent, Stille coupling reaction is carried out 6 ~ 60 hours at 70 ~ 130 DEG C, polyreaction is stopped after cooling, separating-purifying reaction solution, obtains the described polymkeric substance containing two thiophene benzotriazole side chains of following general structure:
In formula, R
1, R
2be C
1~ C
20alkyl, n is the integer of 10 ~ 100.
3. the preparation method containing the polymkeric substance of two thiophene benzotriazole side chains according to claim 2, it is characterized in that, described catalyzer is bis-triphenylphosphipalladium palladium dichloride or tetra-triphenylphosphine palladium; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
4. the preparation method containing the polymkeric substance of two thiophene benzotriazole side chains according to claim 2, it is characterized in that, palladium and three (o-methyl-phenyl-) the phosphine mixture of described catalyzer to be mol ratio be 1:4 ~ 8, or mol ratio is three or two argon benzyl acetone two palladiums and the 2-dicyclohexyl phosphine-2 of 1:4 ~ 8 ', 6 '-dimethoxy-biphenyl mixture; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
5. the preparation method containing the polymkeric substance of two thiophene benzotriazole side chains according to claim 2, it is characterized in that, described organic solvent is selected from least one in toluene, DMF, tetrahydrofuran (THF).
6. the preparation method containing the polymkeric substance of two thiophene benzotriazole side chains according to claim 2, is characterized in that, Stille coupling reaction temperature is at 90 ~ 120 DEG C, the reaction times is 24 ~ 48 hours.
7. the preparation method containing the polymkeric substance of two thiophene benzotriazole side chains according to claim 2, it is characterized in that, separating-purifying reaction solution comprises step:
After reaction stops, methyl alcohol precipitating is added in reaction solution, methyl alcohol and normal hexane extracting is used successively after being filtered by apparatus,Soxhlet's, then be that solvent extraction is to colourless with chloroform, collect chloroformic solution and be spin-dried for and obtain powder, powder after collection, more under vacuo after 50 DEG C of dry 24h, obtains the described polymkeric substance containing two thiophene benzotriazole side chains.
8. an organic solar batteries device, is characterized in that, the electron donor material of its active layer adopts the polymkeric substance containing two thiophene benzotriazole side chains of following structural formula:
In formula, R
1, R
2be C
1~ C
20alkyl, n is the integer of 10 ~ 100.
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Application publication date: 20150429 |