CN104725610A - Dithienylbenzotrithienyl polymer and preparation method and application thereof - Google Patents
Dithienylbenzotrithienyl polymer and preparation method and application thereof Download PDFInfo
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- CN104725610A CN104725610A CN201310728390.XA CN201310728390A CN104725610A CN 104725610 A CN104725610 A CN 104725610A CN 201310728390 A CN201310728390 A CN 201310728390A CN 104725610 A CN104725610 A CN 104725610A
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- 0 Cc1c(c2c(c3c4cc(-c([s]5)ccc5Br)[s]3)[s]c(-c([s]3)ccc3Br)c2)c4c(*)[s]1 Chemical compound Cc1c(c2c(c3c4cc(-c([s]5)ccc5Br)[s]3)[s]c(-c([s]3)ccc3Br)c2)c4c(*)[s]1 0.000 description 2
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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
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- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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Abstract
The invention discloses a dithienylbenzotrithienyl polymer and a preparation method and application thereof. The polymer has a structural formula shown in descriptions, wherein each of R1 and R2 is C1-C20 alkyl, and n is an integer between 10 and 100. The dithienylbenzotrithienyl polymer disclosed by the invention contains dithienyl benzotriazole units and dithienyl silole units, so that the polymer is a donor-receptor type conjugated polymer, has relatively high hole mobility, high open-circuit voltage and relatively good solubility and film-forming property and has a relatively wide absorption range in the range of 300-700nm, and then, the photoelectric conversion efficiency of the polymer in organic solar cells can be increased.
Description
Technical field
The present invention relates to solar cell material field, particularly relate to a kind of two thiophene benzo three thienyl (DTBTT) polymkeric substance and its preparation method and application.
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
Problem to be solved by this invention is the two thiophene benzo three thienyl polymkeric substance providing a kind of photoelectric transformation efficiency higher.
Technical scheme of the present invention is as follows:
A kind of two thiophene benzo three thienyl polymkeric substance provided by the invention, it is obtained by following step:
Under oxygen-free environment, by structural formula be
compd A and structural formula be
compd B be added into containing catalyzer organic solvent in dissolve, described compd A and B mol ratio are 1:1 ~ 1.2; The mixing solutions obtained after dissolving carries out Stille coupling reaction 6 ~ 60 hours at 70 ~ 130 DEG C, stops coupling reaction after cooling, separating-purifying reaction solution, obtains structural formula to be
described two thiophene benzo three thienyl polymkeric substance; Wherein, R
1, R
2be C
1~ C
20alkyl, n is the integer between 10-100.
In a preferred embodiment, described catalyzer is bis-triphenylphosphipalladium palladium dichloride or tetra-triphenylphosphine palladium; Or
Described catalyzer is the mixture of organic palladium and organophosphorus ligand; In described mixture, catalyzer is the mol ratio of organic palladium and organophosphorus ligand is 1:4 ~ 8; Described organic palladium is palladium or three or two argon benzyl acetone two palladiums; Described organophosphorus ligand is three (o-methyl-phenyl-) phosphines or 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl; Preferred described mixture is the mixture of palladium and three (o-methyl-phenyl-) phosphine or three or two argon benzyl acetone two palladiums and 2-dicyclohexyl phosphine-2 ', the mixture of 6 '-dimethoxy-biphenyl.
The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
In a preferred embodiment, described organic solvent is selected from least one in toluene, DMF, tetrahydrofuran (THF).
In a preferred embodiment, the temperature of reaction of coupling reaction is 90 ~ 120 DEG C, and the reaction times is 24 ~ 48 hours.
In a preferred embodiment, the process of separating-purifying reaction solution comprises:
Reaction stopping is cool adds methyl alcohol precipitating but to room temperature in reaction solution, uses methyl alcohol and normal hexane extracting by apparatus,Soxhlet's after being filtered successively; Then be solvent extraction with chloroform to colourless, collect chloroformic solution and be spin-dried for and obtain pressed powder, after the pressed powder collected under vacuo 50 DEG C of dry 24h, obtain as described in two thiophene benzo three thienyl polymkeric substance.
In a preferred embodiment, oxygen-free environment is made up of at least one gas in argon gas and nitrogen.
The present invention also provides a kind of preparation method of above-mentioned two thiophene benzo three thienyl polymkeric substance, comprises the steps:
Under oxygen-free environment, by structural formula be
compd A and structural formula be
compd B be added into containing catalyzer organic solvent in dissolve, described compd A and B mol ratio are 1:1 ~ 1.2; The mixing solutions obtained after dissolving carries out Stille coupling reaction 6 ~ 60 hours at 70 ~ 130 DEG C, stops coupling reaction after cooling, separating-purifying reaction solution, obtains structural formula to be
described two thiophene benzo three thienyl polymkeric substance; Wherein, R
1, R
2be C
1~ C
20alkyl, n is the integer between 10-100.
The present invention provides again a kind of above-mentioned two application of thiophene benzo three thienyl polymkeric substance in organic solar batteries active layer field.
In two thiophene benzo three thienyl polymkeric substance provided by the invention, containing dithiazole benzotriazole unit and two thiophene Silole unit; Therefore, this polymkeric substance is donor-receiver type conjugated polymers, it has higher hole mobility, high open circuit voltage, good solubility property and film forming properties, there is wider absorption region within the scope of 300nm ~ 700nm, this polymkeric substance electricity conversion in organic solar batteries can be improved.
Separately, the preparation method of above-mentioned two thiophene benzo three thienyl polymkeric substance, have employed better simply synthetic route, thus reduces technical process, and starting material are cheap and easy to get, and manufacturing cost is reduced.
Accompanying drawing explanation
Fig. 1 is the ultraviolet-visible absorption spectroscopy figure of the two thiophene benzo three thienyl polymkeric substance that embodiment 1 obtains;
Fig. 2 is the structural representation of the organic solar batteries 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, monomer A, monomers B are all purchased from Taiwan Jiguang Technology Corporation.
Embodiment 1:
The two thiophene benzo three thienyl polymkeric substance of the present embodiment, namely { 2 are gathered, 6-bis-base-4,8-bis-(n-octyloxy) benzene 1,4-Dithiapentalene-co-2,8-bis-(5-base-thiophene)-4,6-bis-octane base benzo three thiophene } (P1), (wherein, R1 is octane base, and R2 is octane base, n=71), 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-(n-octyloxy) benzene 1,4-Dithiapentalene (151mg, 0.2mmol), 2,8-bis-(the bromo-thiophene of 5-)-4,6-bis-octane base benzo three thiophene (159mg, 0.2mmol) adds in the flask filling 10ml toluene solvant, vacuumizes deoxygenation and is filled with argon gas, then bis-triphenylphosphipalladium palladium dichloride (5.6mg, 0.008mmol) is added; 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 solvent extraction with chloroform to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, after collection, obtain P1 product, productive rate 86%. after 50 DEG C of dry 24h under vacuo
Test result is: Molecular weight (GPC, THF, R.I): M
n=48.3kDa, M
w/ M
n=2.2.
Fig. 1 is the ultraviolet-visible absorption spectroscopy figure of two thiophene benzo three thienyl polymkeric substance of embodiment 1; Result shows, this polymkeric substance has comparatively large wider absorption between 300nm ~ 700nm, and wherein maximum absorption band is positioned at about 561nm.
Embodiment 2:
The two thiophene benzo three thienyl polymkeric substance of the present embodiment, namely { 2 are gathered, 6-bis-base-4,8-bis-(methoxyl group) benzene 1,4-Dithiapentalene-co-2,8-bis-(5-base-thiophene)-4,6-bis-NSC 62789 base benzo three thiophene } (P2), (wherein, R1 is methyl, and R2 is NSC 62789 base, 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 and argon gas gas mixture are protected, by 2, 6-bis-tin trimethyl-4, 8-bis-(methoxyl group) benzene 1,4-Dithiapentalene (173mg, 0.3mmol), 2, 8-bis-(the bromo-thiophene of 5-)-4, 6-bis-NSC 62789 base benzo three thiophene (339mg, 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 78%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=121.7kDa, M
w/ M
n=2.0.
Embodiment 3:
The two thiophene benzo three thienyl polymkeric substance of the present embodiment, namely { 2 are gathered, 6-bis-base-4,8-bis-(NSC 62789 oxygen base) benzene 1,4-Dithiapentalene-co-2,8-bis-(5-base-thiophene)-4,6-dimethylbiphenyl three thiophene } (P3), (wherein, R1 is NSC 62789 base, and 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-4,8-bis-(NSC 62789 oxygen base) benzene 1,4-Dithiapentalene (332mg, 0.3mmol), 2,8-bis-(the bromo-thiophene of 5-)-4,6-dimethylbiphenyl three thiophene (197mg, 0.33mmol), palladium (3.5mg, 0.015mmol) He three (o-methyl-phenyl-) phosphine (21mg, 0.06mmol) join in the flask of the DMF filling 12mL, 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 83%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=13.4kDa, M
w/ M
n=2.5.
Embodiment 4:
The two thiophene benzo three thienyl polymkeric substance of the present embodiment, namely { 2 are gathered, 6-bis-base-4,8-bis-(normal butane oxygen base) benzene 1,4-Dithiapentalene-co-2,8-bis-(5-base-thiophene)-4, positive decyl benzo three thiophene of 6-bis-} (P4), (wherein, R1 is normal-butyl, and R2 is positive decyl, n=83), 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-(n-butoxy) benzene 1,4-Dithiapentalene (198mg, 0.3mmol), 2,8-bis-(the bromo-thiophene of 5-)-4,6-didecyl benzo three thiophene (305mg, 0.36mmol), three or two argon benzyl acetone two palladium (9mg, 0.009mmol) with 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl (29mg, 0.072mmol) joins 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 81%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=74.8Da, M
w/ M
n=2.1.
Embodiment 5:
The two thiophene benzo three thienyl polymkeric substance of the present embodiment, namely { 2 are gathered, 6-bis-base-4,8-bis-(n-dodecane oxygen base) benzene 1,4-Dithiapentalene-co-2,8-bis-(5-base-thiophene)-4,6-di-n-hexyl benzo three thiophene } (P5), (wherein, R1 is dodecyl, and R2 is n-hexyl, n=40), 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, 8-bis-(n-dodecane oxygen base) benzene 1,4-Dithiapentalene (226mg, 0.3mmol), 2, 8-bis-(5-base-thiophene)-4, 6-di-n-hexyl benzo three thiophene (221mg, 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 75%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=33.7kDa, M
w/ M
n=2.3.
Embodiment 6:
Originally be embodied as organic photovoltaic cell, as shown in Figure 2, this organic solar batteries 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 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/mouth.
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 thiazoles and polystyrene-sulfonic acid matrix material (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 two thiophene benzo three thienyl polymkeric substance that the present invention obtains; In present embodiment, in the embodiment 1 that electron donor material is, preparation gathers { 2,6-bis-base-4,8-bis-(n-octyloxy) benzene 1,4-Dithiapentalene-co-2,8-bis-(5-base-thiophene)-4,6-bis-octane base benzo three thiophene }.
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 solar cell 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 3.5% of the organic solar batteries 60 of electron donor material based on the copolymer p 1 in embodiment 1.
When this organic solar batteries 60 uses, under light illumination, light transmission substrate 61 and anode 62, the Conduction cavity 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, 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 cavity type electroluminescent 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 solar cell device.And this organic materials can also alleviate the quality of solar cell device, 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.
Claims (10)
1. two thiophene benzo three thienyl polymkeric substance, is characterized in that, it is obtained by following step:
Under oxygen-free environment, by structural formula be
compd A and structural formula be
compd B be added into containing catalyzer organic solvent in dissolve, described compd A and B mol ratio are 1:1 ~ 1.2; The mixing solutions obtained after dissolving carries out Stille coupling reaction 6 ~ 60 hours at 70 ~ 130 DEG C, stops coupling reaction after cooling, separating-purifying reaction solution, obtains structural formula to be
described two thiophene benzo three thienyl polymkeric substance; Wherein, R
1, R
2be C
1~ C
20alkyl, n is the integer between 10-100.
2. two thiophene benzo three thienyl polymkeric substance according to claim 1, 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.
3. two thiophene benzo three thienyl polymkeric substance according to claim 1, it is characterized in that, described catalyzer is the mixture of organic palladium and organophosphorus ligand; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
4. two thiophene benzo three thienyl polymkeric substance according to claim 3, is characterized in that, in described mixture, catalyzer is the mol ratio of organic palladium and organophosphorus ligand is 1:4 ~ 8.
5. two thiophene benzo three thienyl polymkeric substance according to claim 3 or 4, is characterized in that, described organic palladium is palladium or three or two argon benzyl acetone two palladiums; Described organophosphorus ligand is three (o-methyl-phenyl-) phosphines or 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl.
6. two thiophene benzo three thienyl polymkeric substance according to claim 5, it is characterized in that, described mixture is the mixture of palladium and three (o-methyl-phenyl-) phosphine or three or two argon benzyl acetone two palladiums and 2-dicyclohexyl phosphine-2 ', the mixture of 6 '-dimethoxy-biphenyl.
7. two thiophene benzo three thienyl polymkeric substance according to claim 1, it is characterized in that, described organic solvent is selected from least one in toluene, DMF, tetrahydrofuran (THF).
8. two thiophene benzo three thienyl polymkeric substance according to claim 1, it is characterized in that, the process of separating-purifying reaction solution comprises:
Reaction stopping is cool adds methyl alcohol precipitating but to room temperature in reaction solution, uses methyl alcohol and normal hexane extracting by apparatus,Soxhlet's after being filtered successively; Then be solvent extraction with chloroform to colourless, collect chloroformic solution and be spin-dried for and obtain pressed powder, after the pressed powder collected under vacuo 50 DEG C of dry 24h, obtain as described in two thiophene benzo three thienyl polymkeric substance.
9. a preparation method for two thiophene benzo three thienyl polymkeric substance as claimed in claim 1, is characterized in that, comprise the steps:
Under oxygen-free environment, by structural formula be
compd A and structural formula be
compd B be added into containing catalyzer organic solvent in dissolve, described compd A and B mol ratio are 1:1 ~ 1.2; The mixing solutions obtained after dissolving carries out Stille coupling reaction 6 ~ 60 hours at 70 ~ 130 DEG C, stops coupling reaction after cooling, separating-purifying reaction solution, obtains structural formula to be
described two thiophene benzo three thienyl polymkeric substance; Wherein, R
1, R
2be C
1~ C
20alkyl, n is the integer between 10-100.
10. two application of thiophene benzo three thienyl polymkeric substance in organic solar batteries active layer field as claimed in claim 1.
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| CN111205307A (en) * | 2020-02-27 | 2020-05-29 | 中国科学院宁波材料技术与工程研究所 | Thienobenzothiadiazoledione organic compound, and preparation method and application thereof |
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| CN111205307A (en) * | 2020-02-27 | 2020-05-29 | 中国科学院宁波材料技术与工程研究所 | Thienobenzothiadiazoledione organic compound, and preparation method and application thereof |
| CN111205307B (en) * | 2020-02-27 | 2022-11-04 | 中国科学院宁波材料技术与工程研究所 | Thienobenzothiadiazoledione organic compound, and preparation method and application thereof |
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Application publication date: 20150624 |