CN105348274A - Benzotriazole small-organic-molecule photovoltaic material and preparation method and application thereof - Google Patents

Benzotriazole small-organic-molecule photovoltaic material and preparation method and application thereof Download PDF

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CN105348274A
CN105348274A CN201510857159.XA CN201510857159A CN105348274A CN 105348274 A CN105348274 A CN 105348274A CN 201510857159 A CN201510857159 A CN 201510857159A CN 105348274 A CN105348274 A CN 105348274A
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benzotriazole
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汲长艳
殷伦祥
李艳芹
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Dalian University of Technology
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    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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Abstract

The invention discloses a benzotriazole small-organic-molecule photovoltaic material and a preparation method and application thereof and belongs to the field of photoelectric materials. The compound uses benzotriazole as a nucleus, uses triphenylamine as an end group and uses thiophene, a single bond, C = C or C=C as connecting keys respectively. After fluorine atoms having higher electronegativity are introduced to the benzotriazole, the initial oxidation potential of the material is improved. The triphenylamine is used as the end group, so that the electron donating capability of molecules is enhanced, the hole-transporting performance is improved, and the solubility of the compound is improved in coordination with an alkyl group on the benzotriazole. The C = C is introduced in the molecules, so that the absorption range of the compound is widened. The single bond or the C = C is introduced so that the HOMO energy level can be effectively reduced. The VOC of a device is improved through coordination of the single bond or the C = C introduced in the molecules and the monofluoro benzotriazole. The PCE of the synthetic material is above 1.70%, the highest PCE is up to 4.77%, and the benzotriazole small-organic-molecule photovoltaic material has the potential of serving as an efficient small-organic-molecule photovoltaic donor material.

Description

A kind of benzotriazole organic micromolecule photovoltaic material and its preparation method and application
Technical field
The present invention relates to a kind of benzotriazole organic molecule photovoltaic material and preparation method thereof and use the solar cell device that this benzotriazole organic micromolecule is donor material, belonging to organic photoelectrical material field.
Background technology
In recent years, solution processes organic molecule solar cell material is easy to modify, be easy to separating-purifying, element manufacturing low cost and other advantages because having molecular structure, becomes study hotspot gradually.At present, the electricity conversion (PCE) of the solution processes organic molecule area of solar cell of bibliographical information, up to 10.10%, makes to have important theory and actual application value to the research of small molecule photovoltaic material.But relative to polymer class solar cell device, be still on the low side to the whole efficiency of the solar cell device of body based on micromolecular compound.In order to enrich the research range of organic molecule photovoltaic material, need the novel organic micromolecule compound of design and synthesis badly.
Research shows, for the organic molecule photovoltaic material of donor-receiver conjugated structure, the electrophilic unit in molecular structure is most important for designing and developing high performance solar batteries material.Because highest occupied molecular orbital (HOMO) energy level of the electrophilic cell influence material in molecular skeleton, and then determine the open circuit voltage (V of material oC).In recent years, benzotriazole unit is because having good planarity and being easy to carry out the research and development that the features such as structural modification are widely used in multifunctional material, as electrochromism and photovoltaic material field.Containing two strong electron-withdrawing imine structures (C=N) in benzotriazole unit, therefore its derivative all shows lower HOMO energy level, so be easy to show higher V to the solar cell device of body with this compounds oC.Meanwhile, be easy to alkylating N-H key containing one in benzotriazole structure, the solvability of compound after alkylation, can not only be improved, and be beneficial to the charge recombination reduced in charge transfer process.At present, the research for benzotriazole class body heterojunction photovoltaic material mainly concentrates on polymer materials, and the PCE of solution processes polymer solar cell device is more than 7.0%.Therefore, benzotriazole unit can be used as a kind of good electrophilic unit, is applied to the efficient organic molecule donor material of research and development.But compared with polymer materials, the research relating to benzotriazole organic micromolecule compound is comparatively deficient, and the PCE of corresponding solar cell device is generally on the low side.
Summary of the invention
In order to solve the problem, the invention is intended to the research range enriching benzotriazole organic micromolecule photovoltaic material, establish certain theory and experiment basis for advancing the research of efficient benzotriazole micromolecular donor material.
The invention provides a kind of benzotriazole organic micromolecule compound, its structure is as follows:
Wherein, Q, as connecting key, is selected from singly-bound, C=C or C ≡ C, R is the alkyl of C1 ~ C20.
Another object of the present invention is to the synthetic method providing a kind of above-mentioned benzotriazole organic micromolecule photovoltaic material, its preparation process comprises the steps:
Under nitrogen protection, drop in the reaction system of palladium chtalyst by compd A and Compound D according to mol ratio 1:2.2 ~ 2.5, at 70 ~ 110 DEG C, cross-coupling reaction occurs, the reaction times is 24 ~ 36 hours, and crude product obtains organic molecule F after separating-purifying.
Following representation Compound D and compd A are provided:
Compound D is: compd A is:
(1) when Q represents singly-bound, the Suzuki linked reaction system that Compound D and compd A to be added according to mol ratio 2.2:1 with sodium carbonate be alkali, four (triphenyl phosphorus) palladium is catalyzer.The mol ratio of sodium carbonate and compd A is 1:40, and the mol ratio of catalyzer and compd A is 1:10.Reaction mixture was in 110 DEG C of backflows 24 hours.Crude by column chromatography method is purified, and obtain orange compound F 17-hydroxy-corticosterone 1, its structural formula is as follows:
(2) when Q represents C=C, the Heck linked reaction system that Compound D and compd A to be dropped into according to mol ratio 2.5:1 with palladium be catalyzer, Tetrabutyl amonium bromide (TBAB) is part, sodium acetate is alkali.The mol ratio of palladium and compd A is the mol ratio of 1:10, TBAB and compd A is 1:2.5, and the mol ratio of sodium acetate and compd A is 2.5:1.Reaction mixture was in 100 DEG C of backflows 36 hours.Obtain orange red compound F 17-hydroxy-corticosterone 2 after crude by column chromatography separating-purifying, its structural formula is as follows:
(3) when Q represents C ≡ C, Compound D and compd A are dropped into according to mol ratio 2.2:1 with the Sonogashira linked reaction system that two (triphenyl phosphorus) palladium chloride is catalyzer, cuprous iodide is promotor, triethylamine is alkali.The mol ratio of catalyzer and compd A is 1:40, and the mol ratio of promotor and compd A is 1:20, and the mol ratio of alkali and compd A is 1:1.React on 70 DEG C of backflows 24 hours.Crude by column chromatography method separating-purifying, obtain orange compound F 17-hydroxy-corticosterone 3, its structural formula is as follows:
Described benzotriazole compounds can be used as the donor material of organic molecule solar cell device, it and acceptor material [6,6]-phenyl-C61-methyl-butyrate (PC 61bM) mixing is as active coating, is applied to solution processes body heterojunction area of solar cell.
Compared with existing invention technology, the present invention has the following advantages and beneficial effect:
(1) the present invention has synthesized a kind of benzotriazole organic micromolecule first, and it can be used as donor material and is applied to solution processes organic molecule area of solar cell.
(2) the benzotriazole unit of organic molecule of the present invention introduces the larger fluorine atom of electronegativity, electron-withdrawing to strengthen it, and then promote the initial oxidation current potential of molecule; Introduce multiple thiophene unit and singly-bound, C=C or C ≡ C in molecular skeleton as connecting key, to extend the conjugate length of molecule, improve intramolecular charge transmission (ICT) process.The introducing of thiphene ring is beneficial to the energy gap (E reducing material g), increase the light abstraction width of material.Comparatively speaking, after introducing C=C in molecule, the absorption region of compound obviously broadens; After introducing singly-bound or C ≡ C, the HOMO energy level of material effectively reduces.The singly-bound introduced in molecule or C ≡ C and single fluorine benzotriazole work in coordination with the V improving device oC.
(4) organic molecule of the present invention is using triphenylamine units as end group, not only contribute to strengthening to the electron supplying capacity of electronic section, the hole transport performance promoting whole molecule in molecule, and work in coordination with the alkyl introduced on benzotriazole the solvability increasing compound.
(5) under the condition without any aftertreatment, be to the photovoltaic device of body with benzotriazole compounds in the present invention, its optimal result is as follows: J sCfor 13.50mAcm -2, V oCfor 0.98V, packing factor (FF) is 0.36, PCE is 4.77%.This illustrates that described compound possesses the potential as efficient organic molecule photovoltaic material, for design and synthesis is novel, Research Thinking widened by high-efficiency photovoltaic material.
Accompanying drawing explanation
Fig. 1 is F1 normalized ultraviolet visible absorption spectra when chloroformic solution and film-forming state in embodiment 1;
Fig. 2 be in embodiment 1 F1 at the Tetrafluoroboric acid tetrabutyl ammonia/methylene dichloride (Bu of 0.1mol/L 4nBF 4/ CH 2cl 2) cyclic voltammetry curve in solution;
Fig. 3 is F1 and PC in embodiment 1 61the current-voltage curve of BM device when blending ratio is 1:2 (w/w, 12mg/mL);
Fig. 4 is F2 normalized ultraviolet visible absorption spectra when chloroformic solution and film-forming state in embodiment 2;
Fig. 5 be in embodiment 2 F2 at the Bu of 0.1mol/L 4nBF 4/ CH 2cl 2cyclic voltammetry curve in solution;
Fig. 6 is F2 and PC in embodiment 2 61the current-voltage curve of BM device when blending ratio is 1:2 (w/w, 12mg/mL);
Fig. 7 is F3 normalized ultraviolet visible absorption spectra when chloroformic solution and film-forming state in embodiment 3;
Fig. 8 be in embodiment 3 F3 at the Bu of 0.1mol/L 4nBF 4/ CH 2cl 2cyclic voltammetry curve in solution;
Fig. 9 is F3 and PC in embodiment 3 61the current-voltage curve of BM device when blending ratio is 1:2 (w/w, 12mg/mL).
Embodiment
Below in conjunction with specific embodiment, the invention will be further described.
The synthesis of compd A carries out (DyesPigm., 2015,118,37-44 according to the document reported; Synth.Met., 2012,162,630-635; J.Am.Chem.Soc., 2012,134,2599-2612), its step is as follows: fluoro-2 N-methyl-p-nitroanilines of compound 5-and hydrated stannous chloride reduction reaction occur in ethanol and hydrochloride aqueous solution and generate fluoro-1, the 2-phenylenediamine of 4-; Fluoro-1, the 2-phenylenediamine of 4-and Sodium Nitrite react in glacial acetic acid, generate fluoro-1,2, the 3-benzotriazole of 5-; There is nucleophilic substitution reaction in fluoro-1,2, the 3-benzotriazole of 5-and R-Br, obtain 2-alkyl-5-fluorine benzotriazole in methanol solution; 2-alkyl-5-fluorine benzotriazole and bromine through two bromo-reaction, generate the bromo-5-fluorine benzotriazole of 2-alkyl-4,7-bis-in aqueous solution of hydrogen bromide; In the Suzuki reaction system of palladium chtalyst, the bromo-5-fluorine benzotriazole of 2-alkyl-4,7-bis-and 2-thienyl boric acid generate 2-alkyl-4,7-bis-(2-thienyl)-5-fluorine benzotriazole in tetrahydrofuran solution; Under room temperature lucifuge condition, 2-alkyl-4,7-bis-(2-thienyl)-5-fluorine benzotriazole and N-bromo-succinimide (NBS) reacting generating compound A1 in chloroformic solution.Compd A 1 and 2-thienyl boric acid be there is in the toluene solution being alkali with the sodium carbonate of 2mol/L the Suzuki linked reaction of palladium catalyst, generate compd A 2.Finally, there is bromo-reaction and obtain orange compd A in compd A 2 and NBS in ice-water bath.The synthetic route of above-mentioned reaction is as follows:
Wherein, R is the alkyl of C1 ~ C20;
The synthesis of Compound D carries out (Chem.Commun., 2012,48,10627-10629 according to the document reported; J.Mater.Chem.C, 2014,2,4019-4026), its step is as follows: triphenylamine and NBS bromo-reaction occur in ice-water bath and generate 4-bromine triphenylamine.When Q represents singly-bound, Compound D is by 4-bromine triphenylamine and the Miyaura boration Reactive Synthesis of connection pinacol borate by palladium chtalyst.When Q represents C ≡ C, Compound D is synthesized in two steps: the first Sonogashira linked reaction of 4-bromine triphenylamine and trimethyl silicane ethyl-acetylene generation palladium chtalyst, midbody compound N-(4-(trimethyl silicon based) ethynyl) phenyl-N-phenylaniline, then there is eliminative reaction and obtain Compound D in this intermediate in methyl alcohol and tetrahydrofuran (THF) mixing solutions.Formylation reaction is there is and obtains compound 4-(N, N-diphenyl amino) phenyl aldehyde in triphenylamine and phosphorus oxychloride in DMF solution.When Q represents C=C, Compound D is reacted by 4-(N, N-diphenyl amino) phenyl aldehyde and iodide triphenylphosphine salt generation phosphonium ylide and obtained.
The synthetic route of above-mentioned reaction is as follows:
Embodiment 1
Present embodiment discloses the concrete building-up process of organic molecule donor material F1, comprise the steps:
Under nitrogen protection; by compd A (147mg; 0.2mmol); N; N-phenylbenzene-4-(4; 4,5,5-tetramethyl--[2; 1; 3] C oxa-ring pentaborane base) aniline, the D (186mg, 0.5mmol) when namely Q represents singly-bound; sodium carbonate (848mg; 8.0mmol) He four (triphenyl phosphorus) palladium (22mg, 0.02mmol) are dissolved in the mixing solutions of toluene (8mL), deionized water (4mL) and ethanol (2mL), and in 110 DEG C of backflows 24 hours.Question response liquid is cooled to room temperature, to be poured in 20mL deionized water and separatory, to use dichloromethane extraction.Use anhydrous sodium sulfate drying organic phase.Revolve and steam removing organic solvent, crude product, is purified by column chromatography for developping agent with sherwood oil/methylene dichloride (v:v, 5:1), and obtaining target product is orange solids, productive rate 85%.
The above-mentioned reaction formula preparing compound F 17-hydroxy-corticosterone 1 is as follows:
See Fig. 1, be compound F 17-hydroxy-corticosterone 1 normalized ultraviolet-visible absorption spectra figure under chloroformic solution and film-forming state in embodiment 1.As seen from the figure, under chloroformic solution and film-forming state, in embodiment 1, compound F 17-hydroxy-corticosterone 1 all presents 3 obvious absorption peaks within the scope of 300 ~ 600nm, shorter two absorption peaks of wavelength are caused by intramolecular π-π transition, and the longer absorption peak of wavelength is produced by the ICT process between electron-donating group and electron-withdrawing group.In chloroformic solution, the maximum absorption band (λ of compound F 17-hydroxy-corticosterone 1 max sol) be positioned at 484nm place.Due to solid-state lower packing of molecules, the absorption region of compound F 17-hydroxy-corticosterone 1 under film-forming state obviously broadens, and occurs obvious acromion at about 550nm, but the maximum absorption band (λ under film-forming state max film) slightly blue shift.Its optical bandwidth (E can be calculated at the absorption edge of film-forming state from compound F 17-hydroxy-corticosterone 1 g opt) be 2.09eV.
See Fig. 2, be in embodiment 1 compound F 17-hydroxy-corticosterone 1 at the Bu4NBF of 0.1mol/L 4/ CH 2cl 2the cyclic voltammetry curve recorded in solution.As seen from the figure, the initial oxidation current potential of compound F 17-hydroxy-corticosterone 1 is 0.34V, and initial reduction current potential is-1.78V, corresponding HOMO cVfor-5.05eV, LUMO cVfor-2.93eV, by HOMO cV-LUMO cVenergy level difference calculates energy gap (E g cV) be 2.12eV.
See Fig. 3, be with compound F 17-hydroxy-corticosterone 1 and PC in embodiment 1 61bM mixes the current-voltage curve as the photovoltaic device of active coating according to mass ratio 1:2.Test result shows, under the condition without any aftertreatment, and the J of device sCfor 8.80mAcm -2, V oCfor 0.82V, packing factor (FF) is 0.34, PCE is 2.47%.
Embodiment 2
Present embodiment discloses the concrete building-up process of organic molecule donor material F2, comprise the steps:
By compd A (147mg, 0.2mmol), D (136mg when 4-(N, N-diphenyl amino) vinylbenzene and Q represent C=C, 0.5mmol), sodium acetate (410mg, 5mmol), palladium (4mg, 0.02mmol) with TBAB (26mg, 0.08mmol) be dissolved in the DMF solution of 12mL, and in 100 DEG C of backflows 36 hours.Question response liquid is poured into after being cooled to room temperature in 50mL deionized water, with a large amount of deionized water wash of gained organic phase after dichloromethane extraction, and uses anhydrous sodium sulfate drying organic phase.Revolve and steam removing organic solvent, crude product, is purified by column chromatography for developping agent with sherwood oil/methylene dichloride (v:v, 3:1), and obtaining target product is Orange red solid, productive rate 42%.
The above-mentioned reaction formula preparing compound F 17-hydroxy-corticosterone 2 is as follows:
See Fig. 4, be compound F 17-hydroxy-corticosterone 2 normalized ultraviolet-visible absorption spectra figure under chloroformic solution and film-forming state in embodiment 2.As seen from the figure, within the scope of 300 ~ 600nm, due to intramolecular π-π transition with to the ICT between electronics and electron-withdrawing group, in embodiment 2, compound F 17-hydroxy-corticosterone 2 all presents two obvious absorption peaks under solution and film-forming state.With two Compound Phase ratios in embodiment 1 and embodiment 3, because C=C introduces the increase of conjugation degree, the planarity enhancing of rear molecule, so the ultraviolet-ray visible absorbing scope of compound F 17-hydroxy-corticosterone 2 is the widest, λ max soland λ max filmmaximum.E is calculated by compound F 17-hydroxy-corticosterone under film-forming state 2 absorption edge g optfor 2.00eV.
See Fig. 5, be in embodiment 2 compound F 17-hydroxy-corticosterone 2 at the Bu of 0.1mol/L 4nBF 4/ CH 2cl 2the cyclic voltammetry curve recorded in solution.As seen from the figure, the initial oxidation current potential of compound F 17-hydroxy-corticosterone 2 is 0.29V, and initial reduction current potential is-1.76V, corresponding HOMO cVfor-5.00eV, LUMO cVfor-2.95eV, E g cVfor 2.05eV.Compare with the Electrochemical results of two kinds of compounds in embodiment 3 with embodiment 1, in molecule, the introducing of C=C is conducive to the E reducing material g cV.
See Fig. 6, be with compound F 17-hydroxy-corticosterone 2 and PC in embodiment 2 61bM mixes the current-voltage curve as the photovoltaic device of active coating according to mass ratio 1:2.Test result shows, under the condition without any aftertreatment, and the J of device sCfor 7.50mAcm -2, V oCbe 1.79% for 0.72V, FF are 0.33, PCE.Compare with the device detection result of two compounds in embodiment 3 with embodiment 1, the V that in embodiment 2, compound F 17-hydroxy-corticosterone 2 is lower oCbe worth HOMO higher corresponding thereto cVenergy level value is relevant.
Embodiment 3
Present embodiment discloses the concrete building-up process of organic molecule donor material F3, comprise the steps:
By compd A (147mg, 0.2mmol), 4-(N, N-diphenyl amino) phenylacetylene and Q D (134mg when representing C ≡ C, 0.5mmol), two (triphenyl phosphorus) palladium chloride (4mg, 0.005mmol) and cuprous iodide (2mg, 0.01mmol) be dissolved in the mixing solutions of 20mL tetrahydrofuran (THF) and 15mL triethylamine, in 70 DEG C of backflows 24 hours.The reaction solution being cooled to room temperature is poured in 50mL deionized water, with dichloromethane extraction, the organic phase anhydrous sodium sulfate drying after merging.Revolve and steam removing organic solvent, crude product, is purified by column chromatography for developping agent with sherwood oil/methylene dichloride (v:v, 5:1), and obtaining target product is orange solids, productive rate 45%.
The above-mentioned reaction formula preparing compound F 17-hydroxy-corticosterone 3 is as follows:
See Fig. 7, it is compound F 17-hydroxy-corticosterone 3 normalized ultraviolet-visible absorption spectra under chloroformic solution and film-forming state in embodiment 3.As seen from the figure, with two Compound Phase ratios in embodiment 1 and embodiment 2, absorption region relative narrower, the λ of compound F 17-hydroxy-corticosterone 3 when chloroformic solution and film-forming state max filmred shift amount is maximum.This illustrates under film-forming state, and compound F 17-hydroxy-corticosterone 3 shows the strongest ICT.E is calculated by compound F 17-hydroxy-corticosterone under film-forming state 3 absorption edge g optfor 2.10eV.
See Fig. 8, be in embodiment 3 compound F 17-hydroxy-corticosterone 3 at the Bu of 0.1mol/L 4nBF 4/ CH 2cl 2the cyclic voltammetry curve recorded in solution.As seen from the figure, the initial oxidation current potential of compound F 17-hydroxy-corticosterone 3 is 0.46V, and initial reduction current potential is-1.72V, corresponding HOMO cVfor-5.17eV, LUMO cVfor-2.99eV, E g cVfor 2.18eV.With two Compound Phase ratios in embodiment 1 and embodiment 2, the HOMO of compound F 17-hydroxy-corticosterone 3 in embodiment 3 cVand LUMO cVenergy level value is minimum, this is because the C ≡ C introduced in molecular structure has electron-withdrawing, is conducive to the initial oxidation current potential and the initial reduction current potential that promote compound; Meanwhile, the HOMO of compound F 17-hydroxy-corticosterone 3 in the present embodiment cVthe degree reduced obviously is greater than LUMO cV, the therefore E of compound g cVincrease.
See Fig. 9, be with compound F 17-hydroxy-corticosterone 3 and PC in embodiment 3 61bM mixes the current-voltage curve as the photovoltaic device of active coating according to mass ratio 1:2.Test result shows, under the condition without any aftertreatment, and the J of device sCfor 13.50mAcm -2, V oCbe 4.77% for 0.98V, FF are 0.36, PCE.This is the highest numerical value of current benzotriazole class solution processes organic molecule body heterojunction solar cell device.The J that this device is higher sCrelevant with the good ICT shown in its ultraviolet-ray visible absorbing, higher V oCthen lower with it HOMO cVenergy level value is consistent.
In embodiment 1 ~ 3, the optical physics of synthesized compound, electrochemistry and photovoltaic data are listed in table 1.
From table 1, the E of compound F 17-hydroxy-corticosterone in the embodiment of the present invention g optwith E g cVbasically identical; Comparatively speaking, after introducing C=C in molecule, the absorption region of compound obviously broadens; After introducing singly-bound or C ≡ C, the HOMO energy level of compound effectively reduces, and then improves the V of battery oC; With existing document (Synth.Met., 2012,162,630-635) compare, be all show comparatively outstanding Photovoltaic Properties to the photovoltaic device of body with the compound of the present invention's synthesis, be particularly to the small molecule devices of body with compound F 17-hydroxy-corticosterone 3, its PCE is up to 4.77%.The top efficiency that based on the small molecules monocell of benzotriazole class solution processes reach of this result for reporting at present.

Claims (6)

1. a benzotriazole organic micromolecule photovoltaic material, has following structural formula:
Wherein, Q is connecting key, is selected from singly-bound, C=C or C ≡ C, R are the alkyl of C1 ~ C20.
2. the preparation method of benzotriazole organic micromolecule photovoltaic material as claimed in claim 1, is characterized in that, comprise the following steps:
Reaction scheme is as follows:
Wherein: Q is connecting key, be selected from singly-bound, C=C or C ≡ C, R are the alkyl of C1 ~ C20;
Under nitrogen protection, drop in the reaction system of palladium chtalyst by compd A and Compound D according to mol ratio 1:2.2 ~ 2.5, at 70 ~ 110 DEG C, cross-coupling reaction occurs, the reaction times is 24 ~ 36 hours, and crude product obtains organic molecule F after separating-purifying.
3. the preparation method of benzotriazole organic micromolecule photovoltaic material according to claim 2, it is characterized in that, in step (3), when in Compound D, Q represents singly-bound, the Suzuki linked reaction system that Compound D and compd A to be added with sodium carbonate be alkali, four (triphenyl phosphorus) palladium is catalyzer; The mol ratio of compd A and sodium carbonate is 1:40; The mol ratio of catalyzer and compd A is 1:10.
4. the preparation method of benzotriazole organic micromolecule photovoltaic material according to claim 2, it is characterized in that, in step (3), when in Compound D, Q represents C=C, the Heck linked reaction system that to drop into Compound D and compd A with palladium be catalyzer, Tetrabutyl amonium bromide (TBAB) is part, sodium acetate is alkali; The mol ratio of palladium and compd A is the mol ratio of 1:10, TBAB and compd A is 1:2.5, and the mol ratio of sodium acetate and compd A is 2.5:1.
5. the preparation method of benzotriazole organic micromolecule photovoltaic material according to claim 2, it is characterized in that, in step (3), when Q in Compound D represents C ≡ C, Compound D and compd A are dropped into the Sonogashira linked reaction system that two (triphenyl phosphorus) palladium chloride is catalyzer, cuprous iodide is promotor, triethylamine is alkali; The mol ratio of catalyzer and compd A is 1:40, and the mol ratio of promotor and compd A is 1:20, and the mol ratio of alkali and compd A is 1:1.
6. benzotriazole organic micromolecule photovoltaic material as claimed in claim 1 is preparing the application in solar cell device as donor material.
CN201510857159.XA 2015-11-27 2015-11-27 A kind of benzotriazole organic micromolecule photovoltaic material and its preparation method and application Expired - Fee Related CN105348274B (en)

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