CN111718339A - Indene [2,1-b ] carbazoles compound and application thereof in dye-sensitized solar cell - Google Patents
Indene [2,1-b ] carbazoles compound and application thereof in dye-sensitized solar cell Download PDFInfo
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- CN111718339A CN111718339A CN202010409096.2A CN202010409096A CN111718339A CN 111718339 A CN111718339 A CN 111718339A CN 202010409096 A CN202010409096 A CN 202010409096A CN 111718339 A CN111718339 A CN 111718339A
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- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 title claims abstract description 50
- -1 carbazoles compound Chemical class 0.000 title claims abstract description 14
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims abstract description 62
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000011259 mixed solution Substances 0.000 claims abstract description 29
- 239000004408 titanium dioxide Substances 0.000 claims abstract description 28
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 19
- 206010070834 Sensitisation Diseases 0.000 claims abstract description 17
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims abstract description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000002156 mixing Methods 0.000 claims abstract description 11
- 239000000243 solution Substances 0.000 claims abstract description 11
- 238000001035 drying Methods 0.000 claims description 10
- 238000013329 compounding Methods 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 238000007664 blowing Methods 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 150000001716 carbazoles Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 18
- 238000006243 chemical reaction Methods 0.000 abstract description 15
- 230000008313 sensitization Effects 0.000 abstract description 2
- 239000000975 dye Substances 0.000 description 71
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 12
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 10
- 238000001179 sorption measurement Methods 0.000 description 10
- 239000003504 photosensitizing agent Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 230000031700 light absorption Effects 0.000 description 6
- 230000002165 photosensitisation Effects 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229910052755 nonmetal Inorganic materials 0.000 description 3
- 238000002791 soaking Methods 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000001354 calcination Methods 0.000 description 2
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000000861 blow drying Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000434 metal complex dye Substances 0.000 description 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0091—Methine or polymethine dyes, e.g. cyanine dyes having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
- H01G9/2027—Light-sensitive devices comprising an oxide semiconductor electrode
- H01G9/2031—Light-sensitive devices comprising an oxide semiconductor electrode comprising titanium oxide, e.g. TiO2
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
- H01G9/2059—Light-sensitive devices comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution
- H01G9/2063—Light-sensitive devices comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution comprising a mixture of two or more dyes
-
- 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
- Y02E10/542—Dye sensitized solar cells
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Power Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Materials Engineering (AREA)
- Hybrid Cells (AREA)
Abstract
The invention provides an indene [2,1-b ] carbazoles compound and application thereof in a dye-sensitized solar cell, belonging to the technical field of photosensitive dye sensitization. The indene [2,1-b ] carbazole compound and the application thereof in the dye-sensitized solar cell are characterized in that triphenylamine dye AFL8 is dissolved in any one or more solutions containing chloroform, DMF and methanol to obtain a mixed solution a, and a titanium dioxide film is immersed in the mixed solution a; dissolving a photosensitive dye BC in any one or more of chloroform, DMF and methanol to obtain a mixed solution b, taking out a titanium dioxide film, and immersing the titanium dioxide film in the mixed solution b; dissolving triphenylamine dye AFL8 and photosensitive dye BC1 in a solution containing chloroform to obtain a mixed solution c; taking out the titanium dioxide film, and immersing the titanium dioxide film into the mixed solution c; and preparing the titanium dioxide electrode. Compared with the traditional titanium dioxide electrode sensitized by a single mixing method or a step method, the photoelectric conversion efficiency of the dye-sensitized solar cell is improved by about 0.7 percent.
Description
Technical Field
The invention belongs to the technical field of photosensitive dye sensitization, and relates to an indene [2,1-b ] carbazole compound and application thereof in a dye-sensitized solar cell.
Background
Dye Sensitized Solar Cells (DSSC) are promising for replacing silicon semiconductor photoelectric conversion components by virtue of their low cost, low-light power generation, no temperature influence on photoelectric conversion rate, and the like, and become next-generation practical high-performance Solar cells. The photosensitive dye is a key structural material for determining visible light absorption and photoelectric conversion efficiency in the DSSC, and has the characteristics of easy structure modification, low processing cost, good stability and the like.
The research on dye sensitizers of photosensitive dyes at home and abroad mainly comprises two types, one is an organic metal complex, and the other is an organic nonmetal dye. Compared with a noble metal sensitizer, the organic nonmetal dye has the advantages of various molecular structures, low price, environmental friendliness, higher molar extinction coefficient and the like, and is a research hotspot in recent years. The structural general formula of the traditional organic nonmetal dye sensitizer is Donor-pi conjugate bridge-Acceptor (Donor-pi Bride-Acceptor, D-pi-A for short). Carbazole and its derivatives have good light absorption properties and good hole transport ability, and N on carbazole can be better designed and utilized, and is widely applied to materials such as Organic Light Emitting Diodes (OLEDs), organic dye sensitizers, and the like. On the other hand, the fluorene and the derivative have high thermal stability and strong electron transmission capability, and in the photosensitive dye, methylene of the fluorene can be designed into a disubstituted group, so that the fluorene has larger volume and can play a role in inhibiting the aggregation of the photosensitive dye.
Because the light absorption area of each photosensitive dye is limited, the dyes cannot absorb in the full light area, the dyes in different light absorption areas are used together, and the light absorption area can be well widened and the photoelectric conversion efficiency can be improved by utilizing the spectral complementarity of the co-sensitized compound dye. The co-sensitization of the early pure organic photosensitive dye generally adopts the co-sensitization compounding of a classical organic dye sensitizer and a cyanine dye sensitizer, or adopts the co-sensitization compounding of an organic photosensitive dye and a classical organic metal photosensitive dye. The co-sensitization compounding mode has two main modes, one is a direct mixing mode, the other is a step-by-step mode, and the other is a layered mode.
1、Directly mixing the dyes participating in co-sensitization in a certain proportion to prepare a solution, and simultaneously adsorbing the solution on TiO2The spectral response range is extended on the surface, which has the advantage of suppressing the photosensitizing dye in TiO2The light is collected on the surface, and the dark current is effectively reduced. Has the advantage of inhibiting the photosensitizing dye in TiO2Surface accumulation of TiO, with the disadvantage of2The adsorption sites provided by the surface to the dyes are limited and there is a problem of competitive adsorption between different dyes on the membrane surface.
2. The step-by-step method is characterized in that one dye is adsorbed for a period of time in advance and then the second dye is adsorbed, the adsorption sequence and the adsorption time of the dye-co-photosensitizing dye participating in co-sensitization are flexibly and variably completed step by step according to actual requirements, and the method has the advantages that the adsorption amount of each photosensitizer is controlled, and further the short-circuit current J of the co-sensitizing dye is increasedSC. The disadvantage is that the former dye may be dissolved while adsorbing the second dye, resulting in a decrease in the total amount of adsorbed dye and a decrease in the efficiency of the battery.
3. The method of assembling two or more cells sensitized with different dyes in a layered manner to form a new cell is limited due to the complexity of the operation.
Therefore, the photosensitive dye co-sensitization compounding method is proposed to the technical personnel in the field.
Disclosure of Invention
The first purpose of the invention is to solve the problems of the prior art, and to provide an indene [2,1-b ] carbazoles compound.
The first object of the present invention can be achieved by the following technical solutions:
an indene [2,1-b ] carbazoles compound, which is characterized in that the structural formula is as follows:
in the formula, R is C4-C8 alkyl, Ar is C5-C6 aryl, the C5-C6 aryl is unsubstituted or substituted by 1-2 substituent groups A, and the substituent group A is C1-C8 alkyl or C1-C4 alkoxy.
The second purpose of the invention is to solve the problems in the prior art, and to provide an application of the indene [2,1-b ] carbazoles compound in a dye-sensitized solar cell.
The second object of the present invention can be achieved by the following technical solutions:
the application of the indene [2,1-b ] carbazole compound in the dye-sensitized solar cell is characterized in that the indene [2,1-b ] carbazole compound is taken as a photosensitive dye BC to be subjected to co-sensitization compounding with an AFL8 photosensitive dye, and the method comprises the following steps:
(a) dissolving triphenylamine dye AFL8 in any one or more of chloroform, DMF and methanol to obtain a mixed solution a, and immersing a titanium dioxide film in the mixed solution a for several hours;
(b) dissolving indene [2,1-b ] carbazole photosensitive dye BC in any one or more of chloroform, DMF and methanol to obtain a mixed solution b, taking out a titanium dioxide film from the mixed solution a, drying the titanium dioxide film by blowing, and immersing the titanium dioxide film in the mixed solution b for several hours;
(c) mixing and dissolving a triphenylamine dye AFL8 and an indene [2,1-b ] carbazole photosensitive dye BC in a solution containing chloroform according to a certain proportion to obtain a mixed solution c;
(d) taking out the titanium dioxide film from the mixed solution b, drying the titanium dioxide film by blowing, and immersing the titanium dioxide film into the mixed solution c for several hours;
(e) and taking the titanium dioxide film out of the mixed solution c, and drying the film to obtain the photosensitive dye-loaded co-sensitized and compounded titanium dioxide electrode.
The structural formula of the triphenylamine dye AFL8 is shown as follows:
in the formula, triphenylamine dye AFL8 uses asymmetric triphenylamine containing fluorene as an electron donor, benzene, furan ring and the like as pi-bridge, and cyanoacetic acid as an electron donor.
Compared with the prior art, the indene [2,1-b ] carbazole compound and the application thereof in the dye-sensitized solar cell have the following advantages:
1. the invention designs and synthesizes an indene [2,1-b ] carbazole photosensitive dye BC, takes indene [2,1-b ] carbazole as a donor to combine the advantages of carbazole and fluorene, and is favorable for obtaining higher short-circuit current by sharing a benzene ring to form a condensed large-pi aromatic ring. In the specific implementation, the photosensitive dye BC1 is one compound in an indene [2,1-b ] carbazole photosensitive dye BC series, the photosensitive dye BC1 takes benzothiadiazole as a second receptor A, thiophene as a bridge and cyanoacetic acid as a receptor, and the obtained high photoelectric conversion efficiency is 8.01.
2. According to the invention, the triphenylamine dye AFL8 and the indene [2,1-b ] carbazole photosensitive dye BC are compounded, so that the triphenylamine dye AFL8 and the indene [2,1-b ] carbazole photosensitive dye BC are more easily complemented with each other for light absorption compared with a traditional scheme of compounding and co-sensitizing an organic dye and a metal complex dye, and the photoelectric conversion efficiency is obviously improved.
3. According to the invention, the titanium dioxide film is soaked in the mixed solution a, the obtained titanium dioxide film is soaked in the mixed solution b, and finally the mixed solution c is adsorbed on the titanium dioxide film obtained before, so that the situation that the total adsorption amount of the dye is reduced due to the fact that the former dye is possibly dissolved when the second dye is adsorbed in the fractional method can be avoided by combining a direct mixing method and the fractional method, the adsorption amount can be effectively controlled to prevent the dye from being aggregated, and the photoelectric conversion efficiency is improved by about 0.7% compared with the photoelectric conversion efficiency of the traditional single mixing method and the fractional method.
Detailed Description
The following are specific examples of the present invention and further describe the technical solutions of the present invention, but the present invention is not limited to these examples.
The photosensitizing dye BC1 is one compound of indene [2,1-b ] carbazole photosensitizing dye BC series, specifically, the photosensitizing dye BC1 takes benzothiadiazole as a second electron acceptor A, thiophene as a bridge and cyanoacetic acid as an acceptor, and can obtain the photoelectric conversion efficiency of 8.01, and the synthesis is as follows:
a mixture of compound II (0.38g,1mmol), III (0.34g,1.05mmol) and Pd (PPh)3)4(0.14g,0.12mmol)、K2CO3(1.4g,10mmol), water (5mL) in dioxane (10mL), N2And reacting for 24 hours at 100 ℃ under protection. Cooling to room temperature, CH2Cl2Extracting for 3 times, combining organic layers, anhydrous Na2SO4And (5) drying. Column chromatography (V)PE:VEtAcCompound I (0.36g, 62%) was isolated as a dark yellow solid.1HNMR(500MHz,CDCl3)，:9.87(s,1H),8.69(s,1H),8.18(d,J＝4.0Hz,1H),8.15(d,J＝ 7.7Hz,1H),8.10(dd,J＝1.7,8.5Hz,1H),8.07(d,J＝7.5Hz,1H),7.85(d,J＝2 .3Hz,1H),7.83(d,J＝0.78Hz,1H),7.78-7.72(m,4H),7.54(d,J＝8.5Hz,1H ),7.50(t,J＝7.1Hz,1H),7.47(d,J＝8.1Hz,1H),7.30(d,J＝7.5Hz,1H),4.43(t ,J＝7.1Hz,2H),1.981.93(m,2H),1.56(s,6H),1.52-1.46(m,2H),0.95(t,J＝7.3Hz,3H).HRMS:m/z calcd for C36H29N3OS2:584.1825[M-H]-； Found:584.1842。
Dissolving compound I (0.58g,1mmol) and cyanoacetic acid (0.2g,2.3mmol) in a mixed solvent of dry acetonitrile (5mL) and chloroform (15mL), adding piperidine (0.3mL, 3mmo1) dropwise, stirring at 60 deg.C overnight, evaporating to dryness, drying the crude product, and passing through a column (silicagel, CH)3Cl: CH3OH: HAc 300:10:1) gave the brown solid photosensitizing dye BC1(0.29g, 45%).
1HNMR(500MHz,DMSO-d6):8.78(s,1H),8.52(s,1H),8.24-8.18(m, 3H),8.05-8.00(m,2H),7.94(d,J＝7.5Hz,1H),7.83-7.77((m,4H),7.65(d, J＝8.6Hz,1H),7.58(d,J＝8.2Hz,1H),7.46(t,J＝7.4Hz,1H),7.21(t,J＝7.4Hz, 1H),4.37(t,J＝6.7Hz,2H),1.80-1.74(m,2H),1.48(s,6H),1.31-1.25(m,2H) ,0.89(t,J＝7.3Hz,3H).HRMS:m/zcalcd for C39H30N4O2S2:649.1772 [M-H]-；Found:649.1761。
The structural formula of the photosensitive dye BC1 is shown as the following formula:
in the formula, R is butyl, Ar is thiophene, and better battery conversion efficiency in the series is obtained.
The structure of the triphenylamine dye AFL8 participating in compound co-sensitization is shown as follows:
the triphenylamine dye AFL8 is characterized in that asymmetric triphenylamine containing fluorene is used as an electron donor, benzene, furan rings and the like are used as pi bridges, and cyanoacetic acid is used as the electron donor.
TiO2Preparing an electrode: double-layer TiO prepared by silk screen printing2The nano particle film is used as a photoelectrode. In the presence of fluorine-doped SnO2(FTO) conductive glass was printed with a layer of 20nm TiO 12 μm thick2Calcining the particles in a muffle furnace at 450 deg.C for 30min, and adding 40 mol. L-1Of TiCl (A) to (B)4Soaking in water solution at 70 deg.C for 30min, washing with water and ethanol, blow-drying, calcining again at the same temperature in muffle furnace for 30min, cooling to 80 deg.C, and soaking in 3 × 10 under dark condition-4mol·L-1Sensitizing the chloroform-methanol mixed solution of triphenylamine dye AFL8 at room temperature for 24h, taking out, drying, and soaking in 3 × 10-4mol·L-1The mixed solution of the photosensitive dye BC1 and chloroform-methanol is taken out for 18 hours, dried and then dipped into 3 × 10-4mol·L-11: 1 of photosensitive dye BC1 and triphenylamine dye AFL8 for 10 hours, taking out and drying to obtain the dye sensitizer sensitized TiO2The electrode is the working electrode.
Adopting a silk-screen printing method to mix H with a certain concentration2PtCl6The solution was printed on FTO conductive glass and then sintered in a 400 ℃ muffle furnace for 20 min. Dye-adsorbed TiO2The electrode and the platinum counter electrode are assembled into a sandwich structure, and the electrolyte is OPV-AN-I type. At 100mW/cm2Under the irradiation of light intensity, the photovoltage-current characteristic curve is measured. DSSC performance parameters obtained by assembling based on AFL8, BC1 and co-sensitized compound dyes thereof are shown in the following table:
remarking: AFL8/BC1 is the performance of the solar cell assembled after the co-sensitization adsorption of the stepwise mixing method, and AFL8+ BC1 is the performance of the solar cell assembled after the co-sensitization adsorption of the stepwise mixing method.
The photoelectric conversion efficiency of the solar cell assembled by the photosensitive dye BC1 is 8.01%, the photoelectric conversion efficiency of the solar cell assembled by the AFL8 and the BC1 obtained by co-sensitization and compounding by a step-by-step mixing method is 9.07%, and the photoelectric conversion efficiency of the solar cell assembled after co-sensitization and adsorption by a step-by-step method is 8.33%. After the photosensitive dye BC1 and the triphenylamine AFL8 are compounded and co-sensitized, the photoelectric conversion efficiency can be effectively improved, and the efficiency is improved by 0.73% by adopting a step-by-step mixing co-sensitization method.
The specific embodiments described herein are merely illustrative of the spirit of the invention. Various modifications or additions may be made to the described embodiments or alternatives may be employed by those skilled in the art without departing from the spirit or ambit of the invention as defined in the appended claims.
Although each term is used more often herein, the possibility of using other terms is not excluded. These terms are used merely to more conveniently describe and explain the nature of the present invention; they are to be construed as being without limitation to any additional limitations that may be imposed by the spirit of the present invention.
Claims (3)
1. An indene [2,1-b ] carbazoles compound, which is characterized in that the structural formula is as follows:
in the formula, R is C4-C8 alkyl, Ar is C5-C6 aryl, the C5-C6 aryl is unsubstituted or substituted by 1-2 substituent groups A, and the substituent group A is C1-C8 alkyl or C1-C4 alkoxy.
2. The application of the indene [2,1-b ] carbazole compound in the dye-sensitized solar cell according to claim 1, wherein the indene [2,1-b ] carbazole compound is taken as a photosensitive dye BC to be subjected to co-sensitization compounding with an AFL8 photosensitive dye.
3. The use of indene [2,1-b ] carbazoles compounds according to claim 2 in dye-sensitized solar cells, characterized in that it comprises the following steps:
(a) dissolving triphenylamine dye AFL8 in any one or more of chloroform, DMF and methanol to obtain a mixed solution a, and immersing a titanium dioxide film in the mixed solution a for several hours;
(b) dissolving indene [2,1-b ] carbazole photosensitive dye BC in any one or more of chloroform, DMF and methanol to obtain a mixed solution b, taking out a titanium dioxide film from the mixed solution a, drying the titanium dioxide film by blowing, and immersing the titanium dioxide film in the mixed solution b for several hours;
(c) mixing and dissolving a triphenylamine dye AFL8 and an indene [2,1-b ] carbazole photosensitive dye BC in a solution containing chloroform according to a certain proportion to obtain a mixed solution c;
(d) taking out the titanium dioxide film from the mixed solution b, drying the titanium dioxide film by blowing, and immersing the titanium dioxide film into the mixed solution c for several hours;
(e) and taking the titanium dioxide film out of the mixed solution c, and drying the film to obtain the photosensitive dye-loaded co-sensitized and compounded titanium dioxide electrode.
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