CN104926830A - Two-dimensional conjugated dibenzothiophene compound as well as preparation method and application thereof - Google Patents
Two-dimensional conjugated dibenzothiophene compound as well as preparation method and application thereof Download PDFInfo
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- CN104926830A CN104926830A CN201510318555.5A CN201510318555A CN104926830A CN 104926830 A CN104926830 A CN 104926830A CN 201510318555 A CN201510318555 A CN 201510318555A CN 104926830 A CN104926830 A CN 104926830A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- 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
Abstract
The invention discloses a kind of two dimension conjugation benzene thiophene compounds and its preparation method and application. Specifically, the compound of the present invention has general structure shown in formula I, wherein R1 is the linear or branched alkyl group of C6 ~ C12; R2 is the linear chain or branched chain alkylthio group or straight or branched alkoxyl of C6 ~ C12; And R3 is hydrogen atom, the linear chain or branched chain alkylthio group of C6 ~ C12 or straight or branched alkoxyl. The compound of the present invention has the absorption of wider visual field and suitable energy level, and the energy conversion efficiency of the solar battery prepared by the compound is more than 8%, shows excellent photovoltaic performance; In addition, the compound of the present invention can prepare the film of high quality, and the more easy purification than polymer material, the available very high electron rich donor material of purity by the method that solution is processed.
Description
Technical field
The invention belongs to photovoltaic material field, relate to a kind of two-dimentional conjugation benzo two thiophene compound and its production and use, be specifically related to a kind of two-dimentional conjugation benzo two thiophene compound of electron donating group-substituted, its preparation method, and preparing the purposes in organic solar batteries donor material.
Background technology
Due to have preparation technology simple, lightweight, can be made into the features such as flexible broad area device, organic solar batteries is subject to extensive concern at present.Conventional body heterojunction (bulk heterojunction) device architecture (see G. Yu, J. Gao, J. C. Hummelen, F. Wudl, A. J. Heeger,
science,
1995270, pp1789-1791) be normally made up of the transparent positive pole of high work content (ITO), low work content negative pole (Ca, Mg, Al etc.) and the folder usual active coating formed by the blend film of electron rich donor material and fullerene derivative receptor material between a positive electrode and a negative electrode.
Wherein, donor material comprises conjugated polymers donor material and conjugation organic molecule donor material.Compared with conjugated polymers donor material, conjugation organic molecule donor material due to its structure determine, purity is high, the advantage such as batch reproducible and causing studies interest widely (see Y. Lin, Y. Li, X. Zhan,
chem. Soc. Rev.,
2012, 41, pp4245-4272).In conjugation organic molecule donor material, although one-dimensional linear material has good electric property, but up to the present still cannot meet the needs of practical application.Therefore, being expanded to two dimensional configurations from one dimension configuration by material is then a kind of important thinking, and the research and development for electron rich donor material provide wide development space.
Summary of the invention
For above-mentioned situation, the invention provides a kind of two-dimentional conjugation benzo two thiophene compound of electron donating group-substituted, its general structure is such as formula shown in I:
；
Wherein:
R
1for C
6~ C
12straight or branched alkyl;
R
2for C
6~ C
12straight or branched alkylthio or straight or branched alkoxyl group; And
R
3for hydrogen atom, C
6~ C
12straight or branched alkylthio or straight or branched alkoxyl group.
In a preferred embodiment, the R in two-dimentional conjugation benzo two thiophene compound of described electron donating group-substituted
1for C
6~ C
12straight chained alkyl, preferred n-octyl.
In a preferred embodiment, the R in two-dimentional conjugation benzo two thiophene compound of described electron donating group-substituted
2for C
6~ C
12branched alkylthio, preferred 2-ethylhexyl sulfenyl.
In a preferred embodiment, the R in two-dimentional conjugation benzo two thiophene compound of described electron donating group-substituted
3for hydrogen atom or C
6~ C
12straight-chain alkylthio, preferred hydrogen atom.
Again on the one hand, the invention provides a kind of method for the preparation of above-mentioned two-dimentional conjugation benzo two thiophene compound such as formula the electron donating group-substituted shown in I, it comprises the steps:
1) synthesis of intermediate M:
At ambient temperature, add A donor, B donor, catalyzer and toluene in reaction vessel, the mol ratio between wherein said A donor and B donor is 2 ~ 2.2:1, mixes and after stirring, back flow reaction 12 ~ 24 hours under protection of inert gas; After having reacted, by reaction system cool to room temperature, solvent evaporate off in vacuo, column chromatography purification, obtains intermediate M;
；
2) synthesis of end product:
At ambient temperature, intermediate M, 3-ethyl rhodanine, acid binding agent and the dry trichloromethane that obtain in step 1) is added in reaction vessel, mol ratio between wherein said intermediate M and 3-ethyl rhodanine is 1:5 ~ 10, to mix and after stirring, back flow reaction 12 ~ 24 hours under protection of inert gas; After reaction terminates, reaction system is cooled to room temperature, then pours into sedimentation in lower alcohol, suction filtration also collects the solid of sedimentation, and column chromatography purification, obtains two-dimentional conjugation benzo two thiophene compound such as formula the electron donating group-substituted shown in I;
；
Wherein: R
1, R
2and R
3as defined above.
Preferably, in above-mentioned preparation method, catalyzer described in step 1) is palladium phosphine catalyst, preferred tetrakis triphenylphosphine palladium or two (triphenylphosphine) palladium chloride, more preferably tetrakis triphenylphosphine palladium.
Preferably, in above-mentioned preparation method, the mol ratio between the donor of A described in step 1) and B donor is 2:1.
Preferably, in above-mentioned preparation method, column chromatography described in step 1) is silica gel column chromatography, and elutriant is methylene dichloride.
Preferably, in above-mentioned preparation method, step 2) described in acid binding agent be Lewis base, preferred pyridine or triethylamine, more preferably pyridine.
Preferably, in above-mentioned preparation method, step 2) described in mol ratio between intermediate M and 3-ethyl rhodanine be 1:10.
Preferably, in above-mentioned preparation method, step 2) described in lower alcohol be methyl alcohol, ethanol or Virahol, particular methanol.
Preferably, in above-mentioned preparation method, step 2) described in column chromatography be silica gel column chromatography, elutriant is trichloromethane.
Preferably, in above-mentioned preparation method, described rare gas element is nitrogen, helium, neon or argon gas, preferred nitrogen.
Preferably, in above-mentioned preparation method, the time of described back flow reaction is 12 hours.
On the other hand, the invention provides above-mentioned two-dimentional conjugation benzo two thiophene compound such as formula the electron donating group-substituted shown in I and prepare the purposes in organic solar batteries donor material.
Compared with prior art, the present invention of technique scheme is adopted to have following advantage:
1, two-dimentional conjugation benzo two thiophene compound of the present invention has wider visible region absorption and suitable LUMO and HOMO energy level, it can thus be appreciated that introducing electron-donating group in BDTT unit is the effective means improving donor material photovoltaic performance;
2, be to body, PC with two-dimentional conjugation benzo two thiophene compound of the present invention
70bM is that acceptor can prepare body heterojunction organic solar batteries, and its effciency of energy transfer, more than 8%, demonstrates excellent photovoltaic performance;
3, compared with the high-level efficiency small molecule material of bibliographical information, this donor material does not need to use the process such as any additive, solvent annealing more than obtaining of 8% efficiency, demonstrates the potentiality that it is applied for organic solar batteries as donor material;
4, two-dimentional conjugation benzo two thiophene compound of the present invention all has good solubility common are in machine solvent (as trichloromethane, chlorobenzene etc.), and the method can processed by solution prepares high-quality film;
5, compared with polymer materials, the easier purifying of two-dimentional conjugation benzo two thiophene compound of the present invention, can obtain the donor material that purity is very high.
Accompanying drawing explanation
Fig. 1 is the chloroform soln of SMBDTT-S and the uv-visible absorption spectra of solid film of preparation in embodiment one.
Fig. 2 is for body, PC with SMBDTT-S
70bM is the structural representation of blend film as the organic solar batteries device of active coating of acceptor.
Fig. 3 is based on SMBDTT-S/PC
70the current-voltage curve figure of the organic solar batteries of BM.
Embodiment
With specific embodiment, the present invention is made further instructions below with reference to the accompanying drawings, it should be pointed out that providing only for explaining and illustrating the present invention of these drawings and Examples, and should not be regarded as making concrete restriction to scope of the present invention.In addition, unless otherwise noted, the experimental technique recorded in the present invention is ordinary method, and the reaction reagent used all can be obtained by commercial sources.
The synthesis of embodiment one, two-dimentional conjugation benzo two thiophene compound SMBDTT-S.
1, the synthesis of intermediate M1:
At ambient temperature, A donor 2-[5-(5-bromo-3-n-octyl thiophene-2-base) thiophene-2-base]-3-n-octyl thiophene-5-formaldehyde (1.16g is added in 100mL single port flask, 2mmol), B donor 1, two (trimethyl-tin-radical)-4 of 6-, two [5-(the 2-ethylhexyl sulfenyl) thiophene-2-base] benzo [1 of 8-, 2-b:4, 5-b '] two thiophene (0.97g, 1mmol), catalyzer tetrakis triphenylphosphine palladium (47mg, 0.04mmol) with solvent toluene (50mL), to mix and after stirring, under nitrogen protection in 110 DEG C of backflows 24 hours.After completion of the reaction, reaction system is cooled to room temperature, solvent evaporate off in vacuo, is that silica column purification crossed by eluent with methylene dichloride, obtains red brown solid M1(1g, productive rate: 63%).
1H-NMR (400 MHz, CDCl
3): δ (ppm) 9.83 (s, 2H), 7.60-7.59 (d, 4H), 7.35-7.34 (d, 2H), 7.26-7.25 (d, 4H), 7.13 (s, 4H), 3.00-2.99 (d, 4H), 2.85-2.81 (t, 4H), 2.79-2.75 (t, 4H), 1.69-1.27 (m, 66H), 0.97-0.86 (m, 24H)。
2, the synthesis of end product SMBDTT-S: at ambient temperature; intermediate M1(1g is added in 100mL single port flask; 0.6mmol), 3-ethyl rhodanine (1g; 6mmol), dry trichloromethane (40mL) and piperidines (3); mix and after stirring, reflux 12 hours under nitrogen protection.After reaction terminates, reaction system is cooled to room temperature, then pours into sedimentation in 200mL methyl alcohol, suction filtration also collects the solid of sedimentation, is that silica column purification crossed by eluent, obtains black solid SMBDTT-S(0.82g, productive rate: 70%) with trichloromethane.
1H-NMR (400 MHz, CDCl
3): δ (ppm) 7.77 (s, 2H), 7.57 (s, 2H), 7.35-7.34 (d, 2H), 7.25 (s, 2H), 7.23 (s, 2H), 7.22 (s, 2H), 7.13 (s, 2H), 7.12 (s, 2H), 4.20-4.17 (m, 4H), 3.00-2.99 (m, 4H), 2.83-2.75 (m, 8H), 1.68-1.27 (m, 66H), 0.98-0.88 (m, 30H)。
The uv-visible absorption spectra of solution state and thin-film state SMBDTT-S as shown in Figure 1.Therefrom known, the film of this compound has wider absorption between 400 ~ 730nm, and maximum absorption limit is at about 730nm, and corresponding optical band gap is 1.70eV.
The Photovoltaic Properties research of embodiment two, SMBDTT-S.
Be to body with SMBDTT-S, PC
70bM is acceptor, has prepared organic solar batteries device by solution spin coating, and as shown in Figure 2, wherein the laminate structure of device is followed successively by ITO/PEDOT:PSS/ active coating (SMBDTT-S:PC to its structural representation from top to bottom
70bM)/Ca/Al.
With based on SMBDTT-S/PC
70bM(weight ratio 1:0.8) organic solar batteries device be research object, investigate its Photovoltaic Properties, its current-voltage curve figure is as shown in Figure 3.Therefrom known, the open circuit voltage of this device (
v oc) be 0.95V, short-circuit current (
j sc) be 14.08mA/cm
2, packing factor (FF) is 0.619, and energy conversion efficiency (PCE) is 8.28%.With the high-level efficiency small molecule material of bibliographical information unlike, obtaining of this photovoltaic performance, does not need to use the process such as any additive, solvent annealing, shows the potentiality of large-scale commercial applications application.
From above-described embodiment, the micromolecular compound of two-dimentional conjugation benzo two thiophene unit based on electron donating group-substituted in the present invention has widened optical absorption, reduce band gap, and improve the hole mobility of organic semiconductor material, these are all conducive to improving the device performance of organic solar batteries, and for designing wide absorption, the efficient solution processable organic molecule photovoltaic material of low HOMO energy level opens a new way.
Claims (10)
1. two-dimentional conjugation benzo two thiophene compound such as formula the electron donating group-substituted shown in I:
；
Wherein:
R
1for C
6~ C
12straight or branched alkyl;
R
2for C
6~ C
12straight or branched alkylthio or straight or branched alkoxyl group; And
R
3for hydrogen atom, C
6~ C
12straight or branched alkylthio or straight or branched alkoxyl group.
2. two-dimentional conjugation benzo two thiophene compound such as formula the electron donating group-substituted shown in I according to claim 1, is characterized in that:
R
1for C
6~ C
12straight chained alkyl;
R
2for C
6~ C
12branched alkylthio; And
R
3for hydrogen atom or C
6~ C
12straight-chain alkylthio.
3. two-dimentional conjugation benzo two thiophene compound such as formula the electron donating group-substituted shown in I according to claim 2, is characterized in that:
R
1for n-octyl;
R
2for 2-ethylhexyl sulfenyl; And
R
3for hydrogen atom.
4., for the preparation of a method for two-dimentional conjugation benzo two thiophene compound such as formula the electron donating group-substituted shown in I according to claim 1, it comprises the steps:
1) at ambient temperature, add A donor, B donor, catalyzer and toluene in reaction vessel, the mol ratio between wherein said A donor and B donor is 2 ~ 2.2:1, mixes and after stirring, back flow reaction 12 ~ 24 hours under protection of inert gas; After having reacted, by reaction system cool to room temperature, solvent evaporate off in vacuo, column chromatography purification, obtains intermediate M;
；
2) at ambient temperature, intermediate M, 3-ethyl rhodanine, acid binding agent and the dry trichloromethane that obtain in step 1) is added in reaction vessel, mol ratio between wherein said intermediate M and 3-ethyl rhodanine is 1:5 ~ 10, to mix and after stirring, back flow reaction 12 ~ 24 hours under protection of inert gas; After reaction terminates, reaction system is cooled to room temperature, then pours into sedimentation in lower alcohol, suction filtration also collects the solid of sedimentation, and column chromatography purification, obtains two-dimentional conjugation benzo two thiophene compound such as formula the electron donating group-substituted shown in I;
；
Wherein: R
1, R
2and R
3as defined in claim 1.
5. method according to claim 4, is characterized in that:
Catalyzer described in step 1) is tetrakis triphenylphosphine palladium or two (triphenylphosphine) palladium chloride;
Step 2) described in acid binding agent be pyridine or triethylamine;
Step 2) described in lower alcohol be methyl alcohol, ethanol or Virahol;
Step 1) and 2) described in rare gas element be nitrogen, helium, neon or argon gas.
6. method according to claim 5, is characterized in that:
Catalyzer described in step 1) is tetrakis triphenylphosphine palladium;
Step 2) described in acid binding agent be pyridine;
Step 2) described in lower alcohol be methyl alcohol;
Step 1) and 2) described in rare gas element be nitrogen.
7. method according to claim 4, is characterized in that:
Mol ratio between the donor of A described in step 1) and B donor is 2:1;
Step 2) described in mol ratio between intermediate M and 3-ethyl rhodanine be 1:10.
8. method according to claim 4, is characterized in that:
Column chromatography described in step 1) is silica gel column chromatography, and elutriant is methylene dichloride;
Step 2) described in column chromatography be silica gel column chromatography, elutriant is trichloromethane.
9. method according to claim 4, is characterized in that:
Step 1) and 2) described in time of back flow reaction be 12 hours.
10. two-dimentional conjugation benzo two thiophene compound such as formula the electron donating group-substituted shown in I according to claim 1 is preparing the purposes in organic solar batteries donor material.
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| CN112830939B (en) * | 2020-12-23 | 2021-12-10 | 中国科学院重庆绿色智能技术研究院 | Dimer small-molecule electron donor material and preparation method thereof |
| CN112830939A (en) * | 2020-12-23 | 2021-05-25 | 中国科学院重庆绿色智能技术研究院 | Dimer small-molecule electron donor material and preparation method thereof |
| CN114716460A (en) * | 2022-03-25 | 2022-07-08 | 中国科学院宁波材料技术与工程研究所 | Conjugated organic small molecule and preparation method and application thereof |
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