CN108658994A - A kind of porphyrin organic molecule acceptor material and the preparation method and application thereof - Google Patents
A kind of porphyrin organic molecule acceptor material and the preparation method and application thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of organic photoelectrical material, a kind of porphyrin organic molecule acceptor material and the preparation method and application thereof is disclosed.Porphyrin organic molecule acceptor material, structural formula are Formulas I, wherein A is the conjugate unit based on diimide derivative；M is metal ion or hydrogen；Ar is substituted or unsubstituted aromatic group.The derivative that the porphyrin organic molecule acceptor material of the present invention passes through the imidodicarbonic diamide of the big pi-conjugated system of introducing so that conjugate planes and conjugated chain widen, its absorption in visible-range is made to be enhanced；And the acceptor material electronic transmission performance of the present invention is good, maintains the solubility property of material.The acceptor material of the present invention is used for organic photovoltaic battery field.
Description
Technical field
The invention belongs to organic photoelectrical material fields, and in particular to a kind of porphyrin organic molecule acceptor material and its preparation
Method and application.Application of the porphyrin organic molecule acceptor material in organic photovoltaic battery.
Background technology
The energy crisis broken out since the 1970s, as the rapid development and the mankind of society are to traditional
The day of the increase of stone demand for energy, fossil energy exhaustion is already approaching.Therefore, the exploitation profit of the sustainable regenerative resource of green
It is the important subject of current researcher with extremely urgent.The sun it is per second irradiation the earth to the earth energy relative to
5000000 tons of fire coals, and solar energy is the energy of a kind of cleaning, high deposit, wide distribution.Therefore, people just adopt in various manners,
Wish Solar use.Convert the solar into electric energy using photovoltaic cell, be exactly at present it is most effective utilize solar energy
One of technology.
Since 21 century, using crystal silicon as the inorganic solar cell of representative, gradually input has been commercially produced, but still
So face high processing costs, it is difficult to the puzzlement of large area print production.In comparison, organic photovoltaic battery has synthesis cost
The advantages such as low, easy processing (can spin coating, inkjet printing etc.), light, fully compensate for the defect of inorganic solar cell.Therefore,
The research and development of organic photovoltaic battery develop rapidly in recent years.
Organic photovoltaic battery structure is in sandwich type, i.e., clips active layer and boundary layer between electrodes.Active layer is to give
Body material and acceptor material are blended.When illumination is mapped on active layer, active layer gives/acceptor material generation exciton, exciton
Be diffused into/by body section occur separation of charge；The hole of separation and electronics arrive separately at the two poles of the earth, to realize that photoelectricity turns
It changes.And traditional acceptor material uses fullerene derivate, such acceptor material, almost without absorption, and to be not easy in visual field
Regulate and control energy level and band gap；Therefore, which has limited the development of organic photovoltaic battery active layer.Rather than in fullerene acceptor material, gather
The synthesis of object acceptor material is closed for fullerene derivate, preparation process is relatively easy, but since every batch of synthesizes
Molecule there are the differences of molecular weight and the dispersion of distribution so that batch difference battery efficiency is also centainly influenced.In addition, polymer
Acceptor material molecular weight distribution is wide, and there is also considerable degree of difficulties for purification process.For polymeric acceptor material, have
The problem of machine small molecule is not only able to artificial controllable adjusting absorption, energy level, band gap, and there is no polymeric acceptor materials,
So that non-fullerene small molecule receptor material has unique advantage in organic photovoltaic battery.
The porphyrin of early stage is obtained by the methods of extracting and developing, purifying from the natural products containing porphyrin compound,
Such as ferroheme, chlorophyll.Porphyrin tool is conducive to electron-transport there are one big pi-conjugated system.Its big π system is conducive to electronics
Transmission, therefore gradually started applied to acceptor material by people.But due to porphyrin itself absorb it is wider, it is seen that the suction in optical range
It receives and bad, and its rigid structure can influence its solubility in common solvents.
The present invention ensure that the dissolubility of porphyrin, it made to play electronic transmission performance by modifying porphyrin
Meanwhile enhancing the absorption of visible-range.
Invention content
The shortcomings that overcome the prior art and deficiency, the purpose of the present invention is to provide a kind of porphyrin small molecule receptor materials
Material.The present invention has adjusted the dissolubility and visible absorption range of porphyrin, it is made to play electronics by modifying porphyrin
While transmission performance, enhance the absorption of visible-range.
Another object of the present invention is to provide the preparation methods of above-mentioned porphyrin organic molecule acceptor material.
It is still another object of the present invention to provide the applications of above-mentioned porphyrin organic molecule acceptor material.The porphyrin is organic
Small molecule receptor material is applied in organic photovoltaic battery.
The purpose of the present invention is achieved through the following technical solutions：
A kind of porphyrin organic molecule acceptor material, structural formula are Formulas I：
Wherein, A is the conjugate unit with polar group；M is metal ion or hydrogen；Ar is substituted or unsubstituted fragrance
Group；
A is the conjugate unit based on diimide derivative.
A is one kind in following structural unit：
Wherein, R is identical in same structure, and R is hydrogen or C1~20Alkyl.
When the M is metal ion, metal ion is zinc ion, copper ion, magnesium ion or nickel ion.
The Ar has the following structure one kind in unit：
Wherein, R1For hydrogen or C1~20Alkyl.
The porphyrin organic molecule acceptor material is obtained using conventional method.Such as：Organic small point of porphyrin containing alkynyl
Sub- acceptor material is prepared using Sonogashira coupling reactions, and specific preparation method includes the following steps：
In protective atmosphere, using organic solvent as medium, under conditions of alkalinity, by the bis- ethynyl porphyrins of 5,10- with
Halide reacts under the effect of the catalyst, subsequent processing, obtains porphyrin organic molecule acceptor material.
The organic solvent is toluene, chlorobenzene, tetrahydrofuran etc.；The alkaline condition is directed to that three are added in reaction system
Ethamine；The catalyst is that four (triphenylphosphines) close palladium and cuprous iodide；The temperature of the reaction be 70-90 DEG C, reaction when
Between be 72-75 hours；The subsequent processing refers to extracting reaction product, pure by silica gel column chromatography and gel filtration chromatography
Change, be spin-dried for solvent, is dried in vacuo.The extraction refers to being extracted using chloroform.
The mole of the bromide is 3~6 times of the mole of the bis- ethynyl porphyrins of 5,10-, the four (triphenyl
Phosphine) to close the mole of palladium be the 8~16% of the bis- ethynyl porphyrins moles of 5,10-, the mole of the cuprous iodide is 5,10-
The 8~12% of double ethynyl porphyrins moles.
The structure of the bis- ethynyl porphyrins of 5,10- is
Wherein M, Ar are corresponding with M, Ar in porphyrin organic molecule acceptor material formula I；
The structure of the halide is in A ' X, wherein A '-C ≡ C- and porphyrin organic molecule acceptor material formula I
A is corresponded to, and X is halogen, preferably bromine.
A is preferably structural unit (3) or (4) in the porphyrin organic molecule acceptor material formula I.
(such as chloroform, dichloromethane, tetrahydrofuran, n-hexane etc. are common in conventional organic solvent for the acceptor material of the present invention
Solvent) in have certain dissolubility.
The porphyrin organic molecule acceptor material of the present invention is applied in organic photovoltaic battery.
Compared with prior art, the present invention has the following advantages and beneficial effect：
(1) porphyrin organic molecule acceptor material of the invention, by connecting other conjugation groups, has using porphyrin as core
Increase to effect the pi-conjugated system and electron transport ability (A groups) of molecule；Simultaneously by connecting other side chains (Ar groups),
It ensure that the dissolubility of porphyrin；
(2) derivative that porphyrin organic molecule acceptor material of the invention passes through the imidodicarbonic diamide of the big pi-conjugated system of introducing
Object (A groups) so that conjugate planes and conjugated chain widen, while its absorption in visible-range being made to be enhanced；
(3) porphyrin organic molecule acceptor material of the invention in porphyrin cavity by introducing metal ion, due to gold
Belong to the outer shell electron distribution of ion so that the electronic configuration of porphyrin ring and periphery condensed ring more regularization has adjusted synthetic material
HOMO, lumo energy.
Description of the drawings
Fig. 1 is the porphyrin organic molecule acceptor material of embodiment 1 (i.e. example 1) and embodiment 2 (i.e. example 2) in dichloro
The UV-visible absorption spectrum of dichloromethane；
Fig. 2 is the porphyrin organic molecule acceptor material of embodiment 1 (i.e. example 1) and embodiment 2 (i.e. example 2) in film
UV-visible absorption spectrum under state；
Fig. 3 is the photovoltaic cell active layer prepared using the porphyrin organic molecule acceptor material of embodiment 1 (i.e. example 1)
In AM 1.5,100mW/cm2Current -voltage curve figure under illumination；
Fig. 4 is the photovoltaic cell active layer prepared using the porphyrin organic molecule acceptor material of embodiment 2 (i.e. example 2)
In AM 1.5,100mW/cm2Current -voltage curve figure under illumination.
Specific implementation mode
The present invention is described in further detail with reference to specific embodiments and the drawings, but embodiments of the present invention
It is without being limited thereto.
Embodiment 1
A kind of porphyrin organic molecule acceptor material is prepared by the following method to obtain：
(1) synthesis of bis- (5- (the 2- ethylhexyls)-thiophene) zinc protoporphyrins of bis- (the acetenyl) -10,20- of 5,15-
Synthetic route is：
By bis- (5- (the 2- ethylhexyls)-thiophene) zinc protoporphyrins of 5,15- bis- (trimethylsilyl acetylene) -10,20- (165mg,
It 0.17mmol) is dissolved in the tetrahydrofuran solution of 20mL, tetrabutyl ammonium fluoride (0.35mL, 1M in THF) is added, in room temperature
Under be stirred to react 5 minutes, add water quenching to go out reaction, extracted with chloroform, anhydrous sodium sulfate drying is spin-dried for, miscellaneous by gel post separation
Matter is spin-dried for obtaining blackish green solid.1H NMR(400MHz,CDCl3),δ(ppm):9.69(d,4H),9.21(d,4H),7.69
(d,2H),7.17(d,2H),4.16(s,2H),3.09(d,4H),1.82-1.91(m,2H),1.38-1.68(m,16H),
0.97-1.10(m,12H).
(2) synthesis of N, N '-bis- (2- butyl octyls) -1- (5- bromines)-thiophene -3,4,9,10- tetracarboxylic acid diimides：
Into reaction vessel, N, bis- (2- the butyl octyls) -1- thiophene -3,4 of N ' -, 9,10- tetracarboxylic acid diimides are put into
(500mg, 0.618mmol), 50ml chloroforms and 50ml glacial acetic acids after air agitation 1 hour, put into bromo amber under the conditions of being protected from light
Acid imide (NBS, 198mg, 1.12mmol) is warming up to 60 DEG C, and reaction reflux 18 hours, after reaction, it is extra to be washed away with methanol
Acetic acid, washing, chloroform extraction, anhydrous sodium sulfate drying, after being spin-dried for, using silica gel column chromatography, eluant, eluent is petroleum ether：Dichloro
Methane=1:1, obtain purple product.1H NMR(500MHz,CHCl3)δ9.02(s,1H),8.56(s,1H),8.41(s,1H),
8.33 (s, 1H), 8.16 (s, 3H), 7.43 (s, 1H), 7.03 (s, 1H), 4.08 (dd, J=304.4,69.3Hz, 4H), 2.05
(d, J=183.9Hz, 2H), 1.51-1.10 (m, 32H), 0.89 (s, 12H)
(3) bis- (N, N '-bis- (2- butyl octyls) -1- (5- alkynes)-two acyls of thiophene -3,4,9,10- tetrabasic carboxylic acids are sub- by 5,15-
Amine) bis- (5- (the 2- ethylhexyls)-thiophene) zinc protoporphyrins of -10,20- synthesis
Under the protection of argon gas, bis- (5- (the 2- ethyl hexyls of bis- (acetenyl) -10, the 20- of 5,15- are added into reaction vessel
Base)-thiophene) zinc protoporphyrin (150mg, 0.19mmol), N, N '-bis- (2- butyl octyls) -1- (5- bromines)-thiophene -3,4,9,10-
Tetracarboxylic acid diimide (506mg, 0.57mmol), dry toluene (20mL), triethylamine (10mL), cuprous iodide (5.6mg,
0.02mmol) with tetrakis triphenylphosphine palladium (32.4mg, 0.02mmol), reaction system is protected from light, and is stirred to react at 80 DEG C three days,
Reaction finishes, and is cooled to room temperature, and water quenching is added to go out, and is extracted with chloroform, washing, and anhydrous sodium sulfate drying is spin-dried for, crosses silica gel post separation
Crude product (eluant, eluent：Chloroform), then with gel permeation chromatography (Gel Permeation Chromatography, GPC) column chromatography
(tetrahydrofuran is eluant, eluent) obtains blackish green solid i.e. porphyrin organic molecule acceptor material.Quality (MALDI-TOF):
Obs.2424.1；Calculated value (Calcd.for) C152H164N8O8S4Zn,2424.7。
Porphyrin organic molecule acceptor material manufactured in the present embodiment is dissolved in dichloromethane, obtained dichloromethane is molten
Liquid, uv-visible absorption spectra are shown in Fig. 1.
Porphyrin organic molecule acceptor material manufactured in the present embodiment is prepared into film, uv-visible absorption spectra
See Fig. 2.
The photovoltaic cell prepared using the porphyrin organic molecule acceptor material of the present embodiment is in AM 1.5,100mW/cm2
Current -voltage curve under illumination is shown in Fig. 3, device architecture：ITO/PEDOT:PSS/PBDB-T:Acceptor material/Al.
Embodiment 2
A kind of porphyrin organic molecule acceptor material is prepared by the following method to obtain：
(1) synthesis of bis- (5- (the 2- ethylhexyls)-thiophene) zinc protoporphyrins of bis- (the acetenyl) -10,20- of 5,15-
Synthetic route is：
To equipped with bis- (5- (the 2- ethylhexyls)-thiophene) zinc protoporphyrins of 5,15- bis- (trimethylsilyl acetylene) -10,20-
In (165mg, 0.17mmol) container, the tetrahydrofuran dissolving of 20mL is injected, homogeneous solution is obtained；Under inert gas shielding, soon
Speed injection tetrabutyl ammonium fluoride (0.35mL, 1M solu in THF), room temperature condition react 4-5 minutes, and reaction is quenched with water and lives
Property, chloroform (A.R) Rapid Extraction removes solvent after dry, by gel post separation impurity, is spin-dried for obtaining blackish green solid.1H NMR(400MHz,CDCl3),δ(ppm):9.69(d,4H),9.21(d,4H),7.69(d,2H),7.17(d,2H),4.16
(s,2H),3.09(d,4H),1.82-1.91(m,2H),1.38-1.68(m,16H),0.97-1.10(m,12H).
(2) 5,15- bis- (bis- (2- butyl octyls) -1,12- bithiophene -3,4,9,10- tetracarboxylic acid diimides) -10,
The synthesis of bis- (5- (the 2- ethylhexyls)-thiophene) zinc protoporphyrins (SMPDPS) of 20-
Into reaction vessel, under the protection of argon gas, bis- (5- (the 2- ethyl hexyls of bis- (acetenyl) -10, the 20- of 5,15- are added
Base)-thiophene) zinc protoporphyrin (150mg, 0.18mmol), bis- (2- butyl octyls) -1,12- bithiophenes -6- bromo- 3,4,9,10- tetra-
Imide (464.55mg, 0.56mmol) is dissolved with anhydrous tetrahydro furan (20mL) and triethylamine (10mL), is protected from light
Under, merging cuprous iodide (3.54mg, 0.018mmol) and tetrakis triphenylphosphine palladium (21.4mg, 0.018mmol), reaction system
It is protected from light, back flow reaction three days at 80 DEG C, after reaction stops, cooling reaction solution adds water and chloroform, extracted with separatory funnel to room temperature
It takes, anhydrous magnesium sulfate drying is spin-dried for, crosses silica gel post separation crude product (eluant, eluent：Chloroform), gel permeation chromatography (Gel
Permeation Chromatography, GPC) column chromatography (tetrahydrofuran is eluant, eluent), product is blackish green solid i.e. porphin
Quinoline organic molecule acceptor material.Quality (MALDI-TOF):Obs.2324.1；Calculated value (Calcd.for)
C144H156N8O8S4Zn,2320.5.
Porphyrin organic molecule acceptor material manufactured in the present embodiment is dissolved in dichloromethane, obtained dichloromethane is molten
Liquid, uv-visible absorption spectra are shown in Fig. 1.
Porphyrin organic molecule acceptor material manufactured in the present embodiment is prepared into film, uv-visible absorption spectra
See Fig. 2.
The photovoltaic cell prepared using the porphyrin organic molecule acceptor material of the present embodiment is in AM 1.5,100mW/cm2
Current -voltage curve under illumination is shown in Fig. 3, device architecture：ITO/PEDOT:PSS/PTB7:Acceptor material/Al.
Claims (7)
1. a kind of porphyrin organic molecule acceptor material, it is characterised in that：Its structural formula is Formulas I：
Wherein, A is the conjugate unit based on diimide derivative；M is metal ion or hydrogen；Ar is substituted or unsubstituted
Aromatic group.
2. porphyrin organic molecule acceptor material according to claim 1, it is characterised in that：A is in following structural unit
It is a kind of：
Wherein, R is identical in same structure, and R is hydrogen or C1~20Alkyl.
3. porphyrin organic molecule acceptor material according to claim 1, it is characterised in that：
When the M is metal ion, metal ion is zinc ion, copper ion, magnesium ion or nickel ion；
The Ar has the following structure one kind in unit：
Wherein, R1For hydrogen or C1~20Alkyl.
4. a kind of preparation method of porphyrin organic molecule acceptor material, it is characterised in that：Porphyrin organic molecule acceptor material
To contain alkynyl in any one of claims 1 to 3 porphyrin organic molecule acceptor material and structure, using Sonogashira
Prepared by coupling reaction, include the following steps：
In protective atmosphere, using organic solvent as medium, under conditions of alkalinity, by the bis- ethynyl porphyrins of 5,10- and halogenation
Object reacts under the effect of the catalyst, subsequent processing, obtains porphyrin organic molecule acceptor material；
The structure of the bis- ethynyl porphyrins of 5,10- is
Wherein M, Ar are corresponding with M, Ar in porphyrin organic molecule acceptor material formula I；
The structure of the halide is A pairs in A ' X, wherein A '-C ≡ C- and porphyrin organic molecule acceptor material formula I
It answers, X is halogen.
5. the preparation method of porphyrin organic molecule acceptor material according to claim 4, it is characterised in that：It is described organic molten
Agent is toluene, chlorobenzene or tetrahydrofuran；The alkaline condition is directed to that triethylamine is added in reaction system；The catalyst is four
(triphenylphosphine) closes palladium and cuprous iodide.
6. the preparation method of porphyrin organic molecule acceptor material according to claim 4, it is characterised in that：The reaction
Temperature is 70~90 DEG C, and the time of reaction is 72~75 hours；The subsequent processing refers to extracting reaction product, is passed through
Silica gel column chromatography and gel filtration chromatography purifying, are spin-dried for solvent, are dried in vacuo.
7. being applied in organic photovoltaic battery according to any one of claims 1 to 3 porphyrin organic molecule acceptor material.
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| CN111187271A (en) * | 2020-01-08 | 2020-05-22 | 华南理工大学 | Porphyrin organic small molecule receptor material, preparation method thereof and application thereof in organic solar cell |
| CN112331787A (en) * | 2019-12-27 | 2021-02-05 | 广东聚华印刷显示技术有限公司 | Application of metal tetraphenylporphyrin complex in electron transport material, quantum dot light-emitting device and preparation method thereof, and light-emitting device |
| CN112542555A (en) * | 2019-09-20 | 2021-03-23 | Tcl集团股份有限公司 | Compound and preparation method thereof and quantum dot light-emitting diode |
| CN113461715A (en) * | 2021-07-30 | 2021-10-01 | 南京林业大学 | Tetraperylene diimide based phenyl tetraphenanthrene ring conjugated porphyrin derivative and preparation method thereof |
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| CN110143976A (en) * | 2019-06-14 | 2019-08-20 | 湘潭大学 | Based on branching porphyrin-imidodicarbonic diamide small molecule receptor synthetic method and application |
| CN110143976B (en) * | 2019-06-14 | 2021-11-02 | 湘潭大学 | Synthesis method and application of branched porphyrin-perylene diimide-based small molecule receptor |
| CN112542555A (en) * | 2019-09-20 | 2021-03-23 | Tcl集团股份有限公司 | Compound and preparation method thereof and quantum dot light-emitting diode |
| CN112331787A (en) * | 2019-12-27 | 2021-02-05 | 广东聚华印刷显示技术有限公司 | Application of metal tetraphenylporphyrin complex in electron transport material, quantum dot light-emitting device and preparation method thereof, and light-emitting device |
| CN111187271A (en) * | 2020-01-08 | 2020-05-22 | 华南理工大学 | Porphyrin organic small molecule receptor material, preparation method thereof and application thereof in organic solar cell |
| CN113461715A (en) * | 2021-07-30 | 2021-10-01 | 南京林业大学 | Tetraperylene diimide based phenyl tetraphenanthrene ring conjugated porphyrin derivative and preparation method thereof |
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