CN108101834B - Carbazolyl tetraamine pyrene hole transport material and application thereof in perovskite solar cell - Google Patents

Carbazolyl tetraamine pyrene hole transport material and application thereof in perovskite solar cell Download PDF

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CN108101834B
CN108101834B CN201711372263.5A CN201711372263A CN108101834B CN 108101834 B CN108101834 B CN 108101834B CN 201711372263 A CN201711372263 A CN 201711372263A CN 108101834 B CN108101834 B CN 108101834B
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钟羽武
邵将洋
李冬梅
孟庆波
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    • C07D209/80—[b, c]- or [b, d]-condensed
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    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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Abstract

The invention discloses a carbazolyl tetraamine pyrene hole transport material, and preparation and application thereof. The structural general formula of the carbazolyl tetraamine pyrene hole transport material is shown as formula I and formula II. The hole transport material provided by the invention has good conjugation effect and thermal stability, the energy level of the hole transport material is matched with the energy level of the perovskite, and the hole transport material has potential application value in the fields of perovskite solar cells and the like.

Description

Carbazolyl tetraamine pyrene hole transport material and application thereof in perovskite solar cell
Technical Field
The invention belongs to the field of photoelectricity, and relates to a carbazolyl tetraamine pyrene hole transport material and application thereof in a perovskite solar cell.
Background
The perovskite material has the advantages of high extinction coefficient, proper band gap, long charge diffusion range, excellent bipolar carrier transport property, wider spectral absorption range, simple preparation process, mild preparation conditions, high photoelectric conversion efficiency of the prepared battery and the like. At present, the Photoelectric Conversion Efficiency (PCE) of a solar cell based on a perovskite material exceeds 22%, and the PCE becomes a prospective star in the field of photovoltaic power generation and is one of the research hotspots in the field of renewable energy. The use of the organic solid hole transport material improves the photoelectric efficiency and stability of the cell, and becomes an important component of the perovskite cell. At present, hole transport materials applied to perovskite solar cells are mainly divided into two categories, namely organic hole transport materials and inorganic hole transport materials. The selection range of the inorganic hole transport material is narrow, and the photoelectric conversion efficiency of the corresponding device is relatively low. The development of an organic hole transport material with energy level matching and high hole mobility is an effective means for improving the efficiency and stability of a device, and becomes a research hotspot in related fields.
Disclosure of Invention
The invention aims to provide a carbazolyl tetraamine pyrene hole transport material and application thereof in a perovskite solar cell.
The structural general formula of the carbazolyl tetraamine pyrene hole transport material provided by the invention is shown as formula I or formula II,
Figure BDA0001513967550000011
in the formula I and the formula II,
Figure BDA0001513967550000021
R2is C1～C12Alkoxy group of (2).
Specifically, the R is2Can be C1～C6Alkoxy group of (2).
The invention provides a method for preparing a compound shown as a formula I or a formula II, which comprises the following steps:
carrying out coupling reaction on 1, 6-dibromopyrene, alkali and tetra (4-methoxyphenyl) -9H-carbazole-3, 6-diamine, and obtaining a compound shown in the formula I after the reaction is finished;
carrying out coupling reaction on 1,3,6, 8-tetrabromopyrene, alkali and tetra (4-methoxyphenyl) -9H-carbazole-3, 6-diamine, and obtaining the compound shown in the formula II after the reaction is finished.
In the above method, the structural formula of the tetrakis (4-methoxyphenyl) -9H-carbazole-3, 6-diamine is shown in formula III:
Figure BDA0001513967550000022
the structural formula of the 1, 6-dibromopyrene is shown in a formula IV:
Figure BDA0001513967550000023
the structural formula of the 1,3,6, 8-tetrabromopyrene is shown as a formula V:
Figure BDA0001513967550000031
the alkali is at least one of potassium carbonate, sodium carbonate, cesium carbonate, potassium phosphate and sodium hydroxide;
the molar ratio of the 1, 6-dibromopyrene or 1,3,6, 8-tetrabromopyrene, tetra (4-methoxyphenyl) -9H-carbazole-3, 6-diamine and alkali is 1 (2-8) to (2-20), and specifically can be 1: 2.4: 6.3 or 1: 2.9: 7.7.
the coupling reaction is carried out in the presence of a palladium catalyst;
the palladium catalyst is specifically selected from at least one of palladium acetate, bis (triphenylphosphine) palladium dichloride, tetrakis (triphenylphosphine) palladium and tris (dibenzylideneacetone) dipalladium.
The molar ratio of the 1, 6-dibromopyrene or 1,3,6, 8-tetrabromopyrene to the palladium catalyst is 1 (0.01-0.2), and specifically can be 1:0.1 or 1: 0.2;
in the step of coupling reaction, the temperature is 90-150 ℃; the time is 6h-48 h;
the coupling reaction is carried out in an organic solvent and an inert atmosphere;
the organic solvent is at least one selected from toluene, xylene, tetrahydrofuran, dioxane, ethanol and dimethyl sulfoxide;
the inert gas atmosphere is specifically a nitrogen gas atmosphere or an inert gas atmosphere.
The method may further comprise the steps of:
after the coupling reaction is finished, extracting the reaction system for three times by using dichloromethane, drying an organic phase by using anhydrous magnesium sulfate, removing a solvent by rotary evaporation, and then carrying out column chromatography separation and purification; in the step of column chromatography, the eluent used can be composed of petroleum ether and ethyl acetate; specifically, the volume ratio of the petroleum ether to the ethyl acetate may be 4/1.
In addition, the application of the compound shown in the formula I or the formula II provided by the invention in preparing a solar cell and the solar cell containing the compound shown in the formula I or the formula II also belong to the protection scope of the invention.
The compound shown in the formula I or the formula II can be used as a hole transport layer in the solar cell.
The solar cell is specifically a perovskite solar cell; more specifically, the perovskite solar cell may be composed of a transparent substrate, an electron transport layer, a perovskite layer, a hole transport layer and a counter electrode layer in sequence from bottom to top.
The transparent substrate layer can be specifically conductive glass FTO;
the electron transport layer can be composed of a compact titanium dioxide layer and a mesoporous titanium dioxide layer;
the material constituting the perovskite layer is CH3NH3PbI3(ii) a The thickness of the perovskite layer may be specifically 300 nm;
the material constituting the counter electrode layer is Au.
The thickness of the compact titanium dioxide layer can be 40-60nm, and more specifically can be 50 nm; the thickness of the mesoporous titanium dioxide layer can be specifically 140-160nm, and more specifically 150 nm; the thickness of the hole transport layer may be 50 to 100nm, and may be 70 nm. The counter electrode may specifically have a thickness of 70-90nm, more specifically 80 nm.
The invention has the following beneficial effects:
(1) the carbazolyl tetraamine pyrene hole transport material prepared by the invention has better solubility in strong polar solvents such as dimethyl sulfoxide and alcohols and weak polar solvents such as toluene, chlorobenzene, dichloromethane and chloroform.
(2) Compared with the traditional classical Spiro-OMeTAD, the carbazolyl tetraamine pyrene hole transport material prepared by the invention has the advantages of simple preparation and convenient purification.
(3) The carbazole group is introduced into the carbazolyl tetraamine pyrene hole transport material prepared by the invention on the basis of tetraamine pyrene, and the molecule has good conjugation effect, good hole transport performance and electron blocking performance, and is beneficial to effective selective transport of holes. Compared with a tetraamine pyrene hole transport material, the carbazolyl tetraamine pyrene serving as a hole transport layer is applied to the perovskite solar cell, has good energy conversion efficiency, and can be widely applied to the fields of perovskite solar cells and the like.
Drawings
FIG. 1 is an ultraviolet absorption spectrum of example 1 of the present invention;
FIG. 2 is a spectrum of cyclic voltammetry test according to example 1 of the present invention;
FIG. 3 is a graph of current versus voltage for a perovskite solar cell prepared in example 1 of the present invention.
FIG. 4 is an ultraviolet absorption spectrum of example 2 of the present invention;
FIG. 5 is a spectrum of cyclic voltammetry test in example 2 of the present invention;
FIG. 6 is a graph of current versus voltage for a perovskite solar cell prepared in example 2 of the present invention.
Detailed Description
The present invention will be further illustrated with reference to the following specific examples, but the present invention is not limited to the following examples. The method is a conventional method unless otherwise specified. The starting materials are commercially available from the open literature unless otherwise specified.
Example 1 synthesis of a carbazolyl tetraamine pyrene hole transport material having a structural unit of formula I.
A carbazolyl tetramine pyrene hole transport material with a chemical structural formula I is prepared by the following synthetic route:
Figure BDA0001513967550000051
synthesis of Compound a:
110mg of 3, 6-dibromocarbazole and 116mg of di-tert-butyl dicarbonate were dissolved in 10mL of tetrahydrofuran, and 8mg of 4-dimethylaminopyridine was added thereto and then refluxed for 3 hours. After the reaction, the reaction mixture was cooled to room temperature, and the solvent was spin-dried under reduced pressure. Column chromatography purification (eluent: dichloromethane) gave compound a in 90% yield.
Step b:
280mg of 4,4 '-dimethoxydiphenylamine, 250mg of compound a and 170mg of potassium tert-butoxide are dissolved in toluene, 1' -bisdiphenylphosphinoferrocene and tris (dibenzylideneacetone) dipalladium are added under nitrogen protection and heated under reflux for 5 hours. After cooling, the solvent is dried by spinning, toluene is extracted, the organic phase is dried by anhydrous sodium sulfate, the solvent is removed by rotary evaporation, and the compound b is obtained by column chromatography separation and purification, wherein the yield is 73%.
Step c:
310mg of Compound b and potassium hydroxide were dissolved in toluene and heated under reflux for 1 hour. After cooling, the solvent was spin-dried, dichloromethane was extracted, the organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation to give compound c (tetrakis (4-methoxyphenyl) -9H-carbazole-3, 6-diamine) in 92% yield.
Synthesis of a hole transport material having the structure of formula I:
250mg (0.40mmol) of the compound c tetrakis (4-methoxyphenyl) -9H-carbazole-3, 6-diamine, 64mg (0.17mmol) of 1, 6-dibromopyrene, 4mg (0.017mmol) of palladium acetate and 148mg (1.07mmol) of potassium carbonate are dissolved in 15mL of toluene and heated under reflux for 24 hours under nitrogen protection. Extraction with dichloromethane three times, drying of the organic phase over anhydrous magnesium sulphate, removal of the solvent by rotary evaporation, and purification by column chromatography (eluent: petroleum ether/ethyl acetate 4/1, v/v) gives the desired product I in 38% yield. MALDI-TOF 1441.1for [ M]+.1H NMR(300MHz,CDCl3):δ＝8.35(d,J＝5.1Hz,2H),8.13(t,J＝6.2Hz,4H),7.85(t,J＝9.3Hz,2H),7.69(s,4H),7.09-7.02(m,20H),6.89(d,J＝8.7Hz,4H),6.79(d,J＝9.0Hz,16H),3.78(s,24H).
FIGS. 1 and 2 are an ultraviolet absorption spectrum and a cyclic voltammetry test spectrum of the compound of formula I obtained in example 1 of the present invention, respectively; as can be seen, the energy level of the compound shown in the formula I is matched with that of the perovskite.
Example 2 synthesis of carbazolyl tetraamine pyrene hole transport material with structural unit of formula II.
A carbazolyl tetramine pyrene hole transport material with a chemical structural formula II comprises the following synthetic route:
Figure BDA0001513967550000061
synthesis of a hole transport material having the structure of formula II:
250mg (0.40mmol) of tetrakis (4-methoxyphenyl) -9H-carbazole-3, 6-diamine, 70mg (0.14mmol) of 1,3,6, 8-tetrabromopyrene, 6mg (0.026mmol) of palladium acetate and 150mg (1.08mmol) of potassium carbonate were dissolved in 15mL of toluene and heated under reflux for 24 hours under nitrogen. Extraction with dichloromethane three times, drying of the organic phase over anhydrous magnesium sulphate, removal of the solvent by rotary evaporation, and purification by column chromatography (eluent: petroleum ether/ethyl acetate 2/1, v/v) gives the desired product II in 27% yield. MALDI-TOF 2680.7for [ M]+.1H NMR(400MHz,CDCl3):δ＝8.30(s,2H),7.95(s,3H),7.69(s,8H),7.06-6.93(m,49H)，6.76(d,J＝9.2Hz,32H),3.76(s,48H).
FIGS. 4 and 5 are an ultraviolet absorption spectrum and a cyclic voltammetry test spectrum of the compound of formula II obtained in example 2 of the present invention; as can be seen, the energy level of the compound shown in formula II is matched with that of the perovskite.
Example 3 preparation of perovskite solar cell Using Compounds of formula I and formula II obtained in examples 1 and 2
The method comprises the following specific steps: and (3) performing ultrasonic treatment on the FTO conductive glass for 15 minutes by using deionized water, detergent, acetone and ethanol respectively, then drying the FTO conductive glass by using nitrogen, and performing UVO treatment for 30 minutes before spin-coating a compact layer. Respectively spin-coating a dense layer with the thickness of 50nm and a mesoporous layer with the thickness of 150nm on FTO conductive glass by a spin-coating method, and carrying out heat treatment at 500 ℃ for 30 minutes. After natural cooling, the perovskite solution is spin-coated on the mesoporous layer, and annealing treatment is carried out for 5 minutes at 100 ℃ to obtain a perovskite layer with the thickness of 300 nm. And (3) dripping the carbazolyl tetraamine pyrene hole transport material solution shown in the formula I or the formula II onto the perovskite layer, standing for about 10s, and then carrying out spin coating to obtain a hole transport layer with the thickness of 70 nm. Preparing a gold electrode with the thickness of 80nm by adopting a vapor deposition method to obtain the gold electrode.
FIG. 3 is a graph of current versus voltage for the perovskite solar cell obtained in example 1 of the present invention. FIG. 6 is a graph of current versus voltage for the perovskite solar cell obtained in example 2 of the present invention. As can be seen from the figure, the compounds shown in the formula I and the formula II are used as hole transport materials for perovskite solar cells, and have good photoelectric conversion efficiency.
In conclusion, the invention provides a carbazolyl tetraamine pyrene hole transport material, and preparation and application thereof. The carbazole diamine derivative is introduced to the periphery of the hole transport material, so that the carbazole diamine derivative has good solubility in most organic solvents and has high hole mobility and light stability. The hole transport layer is applied to the perovskite solar cell as the hole transport layer, and has good photoelectric conversion efficiency and repeatability, so that the hole transport layer has wide application prospect in the fields of perovskite cells and the like.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any changes or substitutions that can be easily conceived by those skilled in the art within the technical scope of the present invention are included in the scope of the present invention.

Claims (12)

1. A compound of formula I or formula II,
Figure FDA0002891590070000011
in the formula I and the formula II,
Figure FDA0002891590070000012
R2is C1～C12Alkoxy group of (2).
2. The compound of claim 1, wherein: the R is2Is C1～C6Alkoxy group of (2).
3. A process for preparing a compound of formula I or formula II as defined in claim 1, comprising the steps of:
carrying out coupling reaction on 1, 6-dibromopyrene, alkali and tetra (4-alkoxy phenyl) -9H-carbazole-3, 6-diamine, and obtaining a compound shown in the formula I after the reaction is finished;
carrying out coupling reaction on 1,3,6, 8-tetrabromopyrene, alkali and tetra (4-alkoxy phenyl) -9H-carbazole-3, 6-diamine, and obtaining a compound shown in a formula II after the reaction is finished;
the alkoxy is C1～C12Alkoxy group of (2).
4. The method of claim 3, wherein: the alkali is at least one of potassium carbonate, sodium carbonate, cesium carbonate, potassium phosphate and sodium hydroxide;
the molar ratio of the 1, 6-dibromopyrene or 1,3,6, 8-tetrabromopyrene, tetra (4-methoxyphenyl) -9H-carbazole-3, 6-diamine and alkali is 1 (2-8) to (2-20).
5. The method of claim 3, wherein: the coupling reactions are all carried out in the presence of a palladium catalyst.
6. The method of claim 5, wherein: the coupling reaction is carried out in the presence of at least one of palladium acetate, bis (triphenylphosphine) palladium dichloride, tetrakis (triphenylphosphine) palladium and tris (dibenzylideneacetone) dipalladium.
7. The method of claim 5, wherein: the molar ratio of the 1, 6-dibromopyrene or 1,3,6, 8-tetrabromopyrene to the palladium catalyst is 1 (0.01-0.2).
8. The method according to any one of claims 3-7, wherein: in the step of coupling reaction, the temperature is 90-150 ℃; the time is 6h-48 h;
the coupling reaction is carried out in an organic solvent and an inert atmosphere.
9. Use of a compound of formula I or formula II according to any one of claims 1 or 2 for the preparation of a solar cell.
10. Use according to claim 9, characterized in that: the compound shown in the formula I or the formula II is used as a hole transport layer in the solar cell;
the solar cell is a perovskite solar cell.
11. A solar cell comprising a compound of formula I or formula II according to any one of claims 1 or 2.
12. The solar cell of claim 11, wherein: the compound shown in the formula I or the formula II is used as a hole transport layer in the solar cell;
the solar cell is a perovskite solar cell.
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