CN107501232A - It is a kind of using naphtho- indenes fluorenes unit as organic solar batteries small molecule receptor material of core and preparation method and application - Google Patents

It is a kind of using naphtho- indenes fluorenes unit as organic solar batteries small molecule receptor material of core and preparation method and application Download PDF

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CN107501232A
CN107501232A CN201710763636.5A CN201710763636A CN107501232A CN 107501232 A CN107501232 A CN 107501232A CN 201710763636 A CN201710763636 A CN 201710763636A CN 107501232 A CN107501232 A CN 107501232A
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CN107501232B (en
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应磊
傅登豪
郭婷
杨伟
彭俊彪
曹镛
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South China University of Technology SCUT
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • H10K85/624Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
    • HELECTRICITY
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    • H10K85/626Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
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    • H10K85/655Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
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Abstract

The invention discloses a kind of using naphtho- indenes fluorenes unit as organic solar batteries small molecule receptor material of core and preparation method and application.Electrophilic unit, by coupling reaction, is connected to naphtho- indenes fluorenes unit both sides by the preparation method successively using the naphtho- indenes fluorenes unit rolled into a ball containing polar substituent as core, obtains the organic solar batteries small molecule receptor material using naphtho- indenes fluorenes unit as core.The organic solar batteries small molecule receptor material using naphtho- indenes fluorenes unit as core is dissolved in organic solvent with donor material, in ITO/PEDOT:PSS surface spin-coating film, is evaporated removing residual organic solvent, obtains the active layer of organic solar batteries.The organic solar batteries small molecule receptor material using naphtho- indenes fluorenes unit as core of the present invention has the characteristics of simple in construction and easy to process.

Description

A kind of organic solar batteries small molecule receptor material using naphtho- indenes fluorenes unit as core And preparation method and application
Technical field
The present invention relates to organic photoelectrical material technical field, and in particular to it is a kind of using naphtho- indenes fluorenes unit as core it is organic too Positive energy battery small molecule receptor material and preparation method and application.
Background technology
Organic solar batteries (organic photovoltaic cells, OPVs) are easily carried out because its quality of materials is light Chemical constitution designs and synthesis, device preparation technology are simple, it is easy to accomplish the advantage such as large area/flexible device so that You Jitai Positive energy battery turns into the important development direction of solar cell of new generation.
The typical device architecture of organic solar batteries be by indium tin oxide (ITO) transparent anode, metallic cathode and The photoactive layer composition of folder between them.Its operation principle is that sunshine is irradiated on active layer through transparent ITO electrode When, D the and A materials in active layer absorb photon and produce exciton, and exciton diffusion to D/A interface debondings is electronics and hole, electronics Negative electrode is transported by acceptor material and is collected, hole is then transmitted by donor material, is collected at anode, so as to produce Electric current.
In the more than ten years in past, the energy conversion efficiency of solution processing body heterojunction organic solar batteries has obtained prominent fly The development pushed ahead vigorously, from the earliest efficiency less than 1% to the efficiency more than 10% reported recently.Organic photovoltaic efficiency is carried The mainly many new donor materials of height are developed.However, the development of electron acceptor material lags far behind electron donor The development of material.
At present, in the body heterojunction OPVs of solution processing, fullerene and its derivative especially PC61BM and PC71BM is most successful as electron acceptor material.However, fullerene and its derivative also have the weak suction of visible spectral range Receive, limited spectral width, by chemical modification it is difficult to the shortcomings of adjusting the band gap of fullerene.Therefore, study non-fullerene by Body material has been increasingly becoming one of direction for improving organic solar batteries performance.
The content of the invention
It is an object of the invention to provide a kind of organic solar batteries small molecule receptor using naphtho- indenes fluorenes unit as core Material, the material have the characteristics of simple in construction and easy processing.
Another object of the present invention is to provide a kind of described organic solar batteries using naphtho- indenes fluorenes unit as core The preparation method of small molecule receptor material.
It is described a kind of small as the organic solar batteries of core using naphtho- indenes fluorenes unit the present invention also aims to provide The application of numerator acceptor material.
The purpose of the present invention is achieved through the following technical solutions.
A kind of organic solar batteries small molecule receptor material using naphtho- indenes fluorenes unit as core, there is following chemical constitution Formula:
In formula, R is H atom, aryl, carbon number are 1-20 straight chain or branched alkyl, or be that carbon number is 1- 20 alkoxy;B1、B2It is polar substituent group, B1、B2It is independently chosen from aromatic derivatives that are identical or differing, carbon containing The conjugate unit of carbon double bond or the conjugate unit containing triple carbon-carbon bonds;A1、 A2For electrophilic unit that is identical or differing.
Further, B1、B2Structure be independently chosen from any one or two kinds in following structural formula:
Wherein, X is oxygen atom, sulphur atom or selenium atom, and Y is carbon atom or silicon atom;R2、R3Be selected from H atom, aryl, Carbon number 1-20 straight chain or branched alkyl, or carbon number 1-20 alkoxy.
Further, A1、A2Structure be independently chosen from any one or two kinds in following structural formula:
Wherein, R4、R5It is independently chosen from C1~C8 alkyl, R6、R7Be independently chosen from including H atom, F atom, nitro, Cyano group, methyl, ester group or trifluoromethyl.
Further, A1、A2Structure be independently chosen from any one or two kinds in following structural formula:
In formula,It is selected from one or both of following structure:
Wherein, R6、R7、R6’、R7' be independently chosen from including H atom, F atom, nitro, cyano group, methyl, ester group or trifluoro Methyl;R4’、R5' it is independently chosen from C1~C8 alkyl.
Still more preferably, A1、A2Structure be independently chosen from any one or two kinds in following structural formula:
In formula,Selected from one or both of following structure:
Wherein, R6、R7、R6’、R7' be independently chosen from including H atom, F atom, nitro, cyano group, methyl, ester group or trifluoro Methyl;R4’、R5' it is independently chosen from C1~C8 alkyl.
A kind of described method using naphtho- indenes fluorenes unit as the organic solar batteries small molecule receptor material of core is prepared, Comprise the following steps:
Using the naphtho- indenes fluorenes unit rolled into a ball containing polar substituent as core, by coupling reaction, electrophilic unit is connected successively In naphtho- indenes fluorenes unit both sides, the organic solar batteries small molecule receptor material using naphtho- indenes fluorenes unit as core is obtained.
Further, the temperature of the reaction of the coupling reaction is 60 DEG C~70 DEG C.
Further, the time of the coupling reaction is 4~6 hours.
It is described it is a kind of using naphtho- indenes fluorenes unit be the organic solar batteries small molecule receptor materials application of core in preparation The active layer of solar cell, by it is described using naphtho- indenes fluorenes unit be the organic solar batteries small molecule receptor material of core with giving Body material is dissolved in organic solvent, in ITO/PEDOT:PSS surface spin-coating film, is evaporated removing residual organic solvent, obtains To the active layer of organic solar batteries.
Further, the organic solar batteries small molecule receptor material and donor material using naphtho- indenes fluorenes unit as core The mass ratio of material is 1.5:1~1:1.
Further, the organic solvent includes chlorobenzene or o-dichlorohenzene.
Compared with prior art, the invention has the advantages that and beneficial effect:
(1) centered on the present invention uses naphtho- indenes fluorenes unit first, small molecule receptor material, and synthetic method letter have been synthesized It is single, it is easily purified, is advantageous to industrial applications;
(2) the organic solar batteries small molecule receptor material using naphtho- indenes fluorenes unit as core of the invention has preferable Dissolubility and film forming so that based on the active layer of material, when preparing solar cell device, technique is simpler;
(3) the organic solar batteries small molecule receptor material using naphtho- indenes fluorenes unit as core of the invention has bigger Conjugated structure, be advantageous to improve organic solar batteries device efficiency.
Brief description of the drawings
Fig. 1 is compound N FIC and NFIC-M UV-Visible absorption curve map;
Fig. 2 is compound N FIC and NFIC-M thermogravimetric curve figure;
Fig. 3 is compound N FIC electrochemical profiles figure;
Fig. 4 is compound N FIC-M electrochemical profiles figure;
Fig. 5 is current-voltage (J-V) characteristic curve diagram of the photovoltaic device based on compound N FIC and NFIC-M.
Embodiment
The present invention is described in further detail below in conjunction with specific embodiment, but embodiments of the present invention are not limited to This.
Embodiment 1
The preparation of 2- borate -9,9- dioctyl fluorenes
Chemical equation is as follows:
Under an argon atmosphere, bromo- 9, the 9- dioctyl fluorenes (15g, 31.95mmol) of 2- are dissolved in the refined tetrahydrochysenes of 200mL In furans (THF), 1.6mol.L is gradually added dropwise at -78 DEG C-1N-BuLi 39.9mL, react 2 hours, then add 2- it is different Propoxyl group -4,4,5,5- tetramethyls -1,3,2- dioxaborinate 7.73g, continue reaction 1 hour at -78 DEG C, then heat to Room temperature reaction 24 hours;Reactant mixture is poured into water, is extracted with ethyl acetate, after organic layer is washed completely with saline solution, Anhydrous magnesium sulfate is added to dry;After solution concentration, thick pale yellow shape crude product is obtained, (eluant, eluent selection is purified with silica gel column chromatography Petrol ether/ethyl acetate=15/1, v/v), product is placed in refrigerator obtain white solid, yield 70% for a long time.1H NMR、13Compound obtained by C NMR, MS and elementary analysis result show is target product.
Embodiment 2
The preparation of the 2-methyl naphthoate of 1- bromines two
Chemical equation is as follows:
Under an argon atmosphere, the bromo- 2- naphthoic acids (10g, 39.83mmol) of 1- are added in two-mouth bottle, adds 100mL first Alcohol, the concentrated sulfuric acid (39.06mg, 398.29umol) is then added dropwise, is heated to 110 DEG C, react 18h;Reactant mixture is fallen Enter in water, be extracted with ethyl acetate, after organic layer is washed completely with saline solution, add anhydrous magnesium sulfate to dry;After solution concentration, obtain To crude white solid, (eluant, eluent selects petroleum ether/dichloromethane=3/1, v/v) is purified with silica gel column chromatography, when product is long Between place refrigerator in obtain white solid, yield 85%.1H NMR、13C NMR, MS and elementary analysis result show resulting Compound is target product.
Embodiment 3
Compound M1 preparation
Chemical equation is as follows:
Under argon atmosphere, by 2- borates -9,9- dioctyl fluorene (8.5g, 16.45mmol) and the naphthoic acid first of 1- bromines two Ester (6.11g, 23.03mmol) is added in two-mouth bottle, add 150ml toluene dissolved, add sodium carbonate (8.72g, 82.27mmol) with 50mg TBABs, tetra-triphenylphosphine palladium (950.65g, 0.823mmol) is added, at 110 DEG C React 18h;Reactant mixture is poured into water, is extracted with ethyl acetate, after organic layer is washed completely with saline solution, adds anhydrous sulphur Sour magnesium is dried;After solution concentration, (eluant, eluent selects petroleum ether/dichloromethane=5/1, v/v) is purified with silica gel column chromatography, finally Obtain white solid, yield 70%.1H NMR、13Compound obtained by C NMR, MS and elementary analysis result show is target Product M1.
Embodiment 4
Compound M2 preparation
Chemical equation is as follows:
Under argon atmosphere, compound M1 (5.5g, 9.57mmol) is added in single port bottle, adds the anhydrous THF of 50ml Until being completely dissolved;Reaction solution is reacted into 1h at 0 DEG C, then 1.6mol.L is added dropwise-1N-octyl magnesium bromide (C8H17MgBr, 17.9ml), mixed liquor reacts 18h at room temperature;Add water in reaction solution reaction is quenched, with acetic acid second Ester extracts, and after organic layer is washed completely with saline solution, adds anhydrous magnesium sulfate to dry;After solution concentration, purified with silica gel column chromatography (eluant, eluent selects petroleum ether/dichloromethane=3/1, v/v);Product is placed in refrigerator obtain white solid, yield for a long time 80%.1H NMR、13Compound obtained by C NMR, MS and elementary analysis result show is target product M2.
Embodiment 5
Compound M3 preparation
Chemical equation is as follows:
Under argon atmosphere, compound M2 (3.0g, 3.89mmol) is dissolved in 50ml dichloromethane, at room temperature dropwise The diethyl ether solution 1ml of 46.5% boron trifluoride is added, reacts 18h;It is extracted with ethyl acetate, organic layer is washed completely with saline solution Afterwards, anhydrous magnesium sulfate is added to dry;After solution concentration, purified (eluant, eluent selection petroleum ether) with silica gel column chromatography, product is for a long time Place in refrigerator and obtain white solid, yield 90%.1H NMR、13C NMR, MS and elementary analysis result show resulting change Compound is target product M3.
Embodiment 6
Compound M4 preparation
Chemical equation is as follows:
Under argon atmosphere, compound M3 (2g, 2.66mmol) is dissolved in 50mL dichloromethane, adds iron powder (148.28mg, 2.66mmol), then bromine (1.06g, 6.64mmol) is added dropwise, 18h is reacted at room temperature;Use ethyl acetate Extraction, after organic layer is washed completely with saline solution, adds anhydrous magnesium sulfate to dry;After solution concentration, purified and (washed with silica gel column chromatography De- agent selection petroleum ether), yield 75%.1H NMR、13Compound obtained by C NMR, MS and elementary analysis result show is mesh Mark product M4.
Embodiment 7
Compound M5 preparation
Chemical equation is as follows:
Under argon atmosphere, compound M4 (1.8g, 1.98mmol) is incorporated in 100ml two-mouth bottles, is dissolved in 30ml first In benzene, add and compound M5 (4.4g, 9.88mmol) be added dropwise, add tetra-triphenylphosphine palladium (456.63mg, 0.395mmol), after reacting 18h at 110 DEG C, tetrahydrofuran THF and diluted hydrochloric acid aqueous solution (2molL are added-1) each 5ml Mixed liquor is acidified 6h;Reactant mixture is poured into water, is extracted with ethyl acetate, after organic layer is washed completely with saline solution, is added Anhydrous magnesium sulfate is dried;After solution concentration, (eluant, eluent selection petroleum ether/dichloromethane=2/1, v/ is purified with silica gel column chromatography V), greenish yellow solid, yield 70% are finally given.1H NMR、13C NMR, MS and elementary analysis result show resulting chemical combination Thing is target product M6.
Embodiment 8
Compound N FIC preparation
Chemical equation is as follows:
Under argon atmosphere, by compound M6 (200mg, 0.205mmol) and compound M7 (319.16mg, 1.64mmol) it is incorporated in 100ml two-mouth bottles, is dissolved in 12ml chloroforms, add 1ml pyridines, reacts 4h at 65 DEG C;Will Reactant mixture is poured into water, and is extracted with ethyl acetate, and after organic layer is washed completely with saline solution, adds anhydrous magnesium sulfate to dry; After solution concentration, (eluant, eluent selects petroleum ether/dichloromethane=2/1, v/v) is purified with silica gel column chromatography, finally gives royal purple Color solid, yield 80%.1H NMR、13Compound obtained by C NMR, MS and elementary analysis result show is target product NFIC。
Embodiment 9
Compound N FIC-M preparation
Chemical equation is as follows:
Under argon atmosphere, by compound M6 (200mg, 0.205mmol) and compound M8 (342.22mg, 1.64mmol) it is incorporated in 100ml two-mouth bottles, is dissolved in 12ml chloroforms, add 1ml pyridines, reacts 4h at 65 DEG C;Will Reactant mixture is poured into water, and is extracted with ethyl acetate, and after organic layer is washed completely with saline solution, adds anhydrous magnesium sulfate to dry; After solution concentration, (eluant, eluent selects petroleum ether/dichloromethane=2/1, v/v) is purified with silica gel column chromatography, finally gives royal purple Color solid, yield 85%.1H NMR、13Compound obtained by C NMR, MS and elementary analysis result show is target product NFIC-M。
Acceptor material compound N FIC and NFIC-M UV-Visible absorption curve map are as shown in figure 1, two acceptor materials Absorption curve difference under chlorobenzene solution state is smaller, and NFIC and NFIC-M has 300~400nm and 500~700nm Double-absorption.
In N2Atmosphere under, tested by 20 DEG C/min of heating rate, using weightlessness loss up to temperature when 5% as Decomposition temperature Td, compound N FIC and NFIC-M thermogravimetric curve figure as shown in Fig. 2 as shown in Figure 2, compound N FIC with NFIC-M decomposition temperature Td shows that NFIC and NFIC-M acceptor materials have preferable heat endurance in 353 DEG C and 347 DEG C, Sufficiently stable it is used for element manufacturing with using in sign, and related heat treatment can be carried out.
Compound N FIC and compound N FIC-M electrochemical profiles figure difference as shown in Figure 3 and Figure 4, can by Fig. 3 and Fig. 4 Know, compound N FIC and NFIC-M initial reduction current potential are respectively -1.50V and -1.55V, therefore obtain lumo energy value difference For -2.92eV and -2.87eV;NFIC-M lumo energy is slightly above NFIC ,-the CH on this indone unit with NFIC-M3Have Close, introduce the electron-withdrawing power that methyl structural can control receptor unit, and then control the lumo energy of material.
Embodiment 10
The preparation of organic solar batteries based on naphtho- indenes fluorenes small molecule receptor material and sign
BHJ-OPV devices use traditional " sandwich " structure, i.e. ITO/PEDOT:PSS/active layer/ PFNDI-Br/Al, specifically, ITO is positive pole, and Al is negative pole, PEDOT:PSS is hole transmission layer, and PFNDI-Br passes for electronics Defeated layer.
BHJ-OPV devices are prepared, are specifically comprised the following steps:
(1) ito glass is cleaned by ultrasonic with acetone, detergent, deionized water and isopropanol successively first, when cleaning every time Between be 10min;By PEDOT:PSS(1:1, w/w) aqueous solution is spun on the ito glass cleaned under 2000rpm rotating speed, Thickness is 30nm, then in 150 DEG C of air drying 15min, removes PEDOT:The aqueous solvent remained in PSS, obtains ITO/ PEDOT:PSS films;
(2) by ITO/PEDOT:PSS films are transferred in nitrogen glove box, and active layer donor is matched somebody with somebody with acceptor blend solution System and spin-coating film are carried out in glove box;Donor material selects PTB7-Th (PCE10), and PCE10 chemical constitution is as follows Shown (n is the degree of polymerization):
Respectively by the NFIC and NFIC-M dichlorobenzene solution (quality of donor material and acceptor material NFIC and NFIC-M Than selecting 1 respectively:1 and 1:1.5, concentration is set as 8.5mgml-1) with sol evenning machine it is spun to ITO/PEDOT:PSS films Surface prepares film forming, thickness 30nm, and 110 DEG C of annealing 15min under nitrogen atmosphere, removes the aqueous solvent of residual, is lived Property layer;
In testing NFIC and NFIC-M Thin Films UV-vis light absorbs, absorbed compared to solution, film absorption has Wider array of absorption region, and NFIC compared with NFIC-M film maximum absorption band solution absorb have obvious red shift, point 27nm and 33nm are not reached, this is due to caused by thin-film state issues raw intermolecular aggregation;In film absorption, NFIC and NFIC-M absorption band edge is each about 700nm, therefore by Eg opt=1240/ λ can obtain NFIC and NFIC-M optical band gap is each about 1.78eV。
(3) by 1mgml-1PFNDI-Br methanol solution is attached on active layer and continues 30s at 3,000 rpm, makes Thickness reaches 10nm, is electron transfer layer;Last Al negative electrodes are in constant pressure 5 × 10-4Under conditions of Pa, evaporation arrives electron transfer layer On, Al cathode electrode layer thickness is 100nm, obtains the BHJ-OPV devices.
It must be 5.7mm that the area of the active layer of the BHJ-OPV devices of preparation, which is calculated,2;The electric current of the BHJ-OPV devices of preparation- Voltage (J-V) indicatrix is 100mWcm in intensity of illumination by Keithley 2602-2When measure, the BHJ-OPV devices measured Current-voltage (J-V) characteristic curve diagram of part is as shown in figure 5, from Fig. 5:For PTB7-Th/NFIC devices, in donor With being 1 by body mass ratio:When 1, measured open-loop voltage VOC=0.91V, current density, JSC=8.28mAcm-2, filling system Number FF=32.07%, PCE=2.42%;For PTB7-Th/NFIC-M devices, in donor with being 1 by body mass ratio:1.5 when Measured open-loop voltage VOC=1.01V, current density, JSC=4.92mAcm-2, fill factor FF=28.51%, PCE =1.42%.
In addition, it is 1 in the mass ratio from donor material and acceptor material NFIC:Obtain device when 1.5 to be tested, institute The open-loop voltage V measuredOC=0.92V, current density, JSC=9.01mAcm-2, fill factor FF=33.34%, PCE= 2.76%.
Above example is only the preferred embodiment of the invention, is not intended to limit the invention protection domain.This area skill Art personnel in the case where the present invention guides, any replacement for not changing spirit of the invention made to the embodiment of the present invention, modification, Combination or simplification etc., will be within the scope of the present invention.

Claims (10)

1. a kind of organic solar batteries small molecule receptor material using naphtho- indenes fluorenes unit as core, it is characterised in that have such as Lower chemical structural formula:
In formula, R is H atom, aryl, carbon number are 1-20 straight chain or branched alkyl, or be that carbon number is 1-20's Alkoxy;B1、B2It is polar substituent group, B1、B2It is independently chosen from aromatic derivatives that are identical or differing, carbon-carbon double The conjugate unit of key or the conjugate unit containing triple carbon-carbon bonds;A1、A2For electrophilic unit that is identical or differing.
A kind of 2. organic solar batteries small molecule receptor material using naphtho- indenes fluorenes unit as core according to claim 1 Material, it is characterised in that B1、B2Structure be independently chosen from any one or two kinds in following structural formula:
Wherein, X is oxygen atom, sulphur atom or selenium atom, and Y is carbon atom or silicon atom;R2、R3It is former to be selected from H atom, aryl, carbon Subnumber 1-20 straight chain or branched alkyl, or carbon number 1-20 alkoxy.
A kind of 3. organic solar batteries small molecule receptor material using naphtho- indenes fluorenes unit as core according to claim 1 Material, it is characterised in that A1、A2Structure be independently chosen from any one or two kinds in following structural formula:
Wherein, R4、R5It is independently chosen from C1~C8 alkyl, R6、R7Be independently chosen from including H atom, F atom, nitro, cyano group, Methyl, ester group or trifluoromethyl.
A kind of 4. organic solar batteries small molecule receptor material using naphtho- indenes fluorenes unit as core according to claim 1 Material, it is characterised in that A1、A2Structure be independently chosen from any one or two kinds in following structural formula:
In formula,It is independently chosen from one or both of following structure:
Wherein, R6、R7、R6’、R7' be independently chosen from including H atom, F atom, nitro, cyano group, methyl, ester group or trifluoromethyl; R4’、R5' it is independently chosen from C1~C8 alkyl.
A kind of 5. organic solar batteries small molecule receptor material using naphtho- indenes fluorenes unit as core according to claim 1 Material, it is characterised in that A1、A2Structure be independently chosen from any one or two kinds in following structural formula:
In formula,Selected from one or both of following structure:
Wherein, R6、R7、R6’、R7' be selected from including H atom, F atom, nitro, cyano group, methyl, ester group or trifluoromethyl;R4’、 R5' it is selected from C1~C8 alkyl.
6. prepare a kind of using naphtho- indenes fluorenes unit as small point of the organic solar batteries of core described in any one of Claims 1 to 5 The method of sub- acceptor material, it is characterised in that comprise the following steps:
Using the naphtho- indenes fluorenes unit rolled into a ball containing polar substituent as core, by coupling reaction, electrophilic unit is connected to naphthalene successively And indenes fluorenes unit both sides, obtain the organic solar batteries small molecule receptor material using naphtho- indenes fluorenes unit as core.
A kind of 7. organic solar batteries small molecule receptor material using naphtho- indenes fluorenes unit as core according to claim 6 Preparation method, it is characterised in that the temperature of the coupling reaction be 60 DEG C~70 DEG C;The time of the coupling reaction is 4~6 Hour.
8. described in any one of Claims 1 to 5 it is a kind of using naphtho- indenes fluorenes unit as core organic solar batteries small molecule by Body materials application is in the active layer for preparing solar cell, it is characterised in that by described using naphtho- indenes fluorenes unit as the organic of core Solar cell small molecule receptor material is dissolved in organic solvent with donor material, in ITO/PEDOT:PSS surface spin coating Film forming, removing residual organic solvent is evaporated, obtains the active layer of organic solar batteries.
9. application according to claim 8, it is characterised in that the organic solar electricity using naphtho- indenes fluorenes unit as core The mass ratio of pond small molecule receptor material and donor material is 1.5:1~1:1.
10. application according to claim 8, it is characterised in that the organic solvent includes chlorobenzene or o-dichlorohenzene.
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