CN109293890A - A kind of fluoro D-A polymer and the preparation method and application thereof - Google Patents

A kind of fluoro D-A polymer and the preparation method and application thereof Download PDF

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CN109293890A
CN109293890A CN201811109581.7A CN201811109581A CN109293890A CN 109293890 A CN109293890 A CN 109293890A CN 201811109581 A CN201811109581 A CN 201811109581A CN 109293890 A CN109293890 A CN 109293890A
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翟奕雲
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    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
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    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/50—Physical properties
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    • C08G2261/90—Applications
    • C08G2261/91—Photovoltaic applications
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y02E10/00—Energy generation through renewable energy sources
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    • Y02E10/549—Organic PV cells

Abstract

The invention discloses a kind of fluoro D-A copolymers applied to solar battery photoactive layer, using diazosulfide derivative containing F as receptor unit, D1 [5,5'- bis- (tin trimethyl) -2,2'- bithiophene] and D2 [3,4'- bis- fluoro- 5,5'- bis- (tin trimethyl) -2,2'- bithiophene] it is used as donor element, by the method for ternary polymerization, and the ratio for adjusting D1 and D2 synthesizes the fluoro D-A copolymer of multiple and different D monomer fluorine contents.Under optimal D monomer F content situation, fluoro D-A polymer short circuit current of the invention is up to 14.5mA/cm2, highest shows 9.86% transfer efficiency.

Description

A kind of fluoro D-A polymer and the preparation method and application thereof
Technical field
The invention belongs to organic solar batteries technical fields, and in particular to a kind of fluoro D-A polymer and its preparation side Method and application.
Background technique
The Energies control of organic polymer, the photon including low strap gap material designed for collecting wide solar spectrum, And then promote the promotion of short circuit current.Regulation donor material HOMO energy level can promote open-circuit voltage.Polymeric donor and fowler LUMO is effectively deviated between alkene receptor, is the Key Strategy for realizing high-performance polymer solar cell.
In a large amount of D-A polymer, there is the polymer of fluorination structural unit to cause great interest recently, because The high energy conversion efficiency more than 7% is realized by the fluorination of unit.The research of a certain unit fluorination reaction in polymer It is concentrated mainly on A unit, it is less that the fluorination on D unit influences research to photovoltaic performance.
Random 1D-2A and 2D-1A terpolymer includes D and two A unit (or two D and A units), it Be a kind of very promising method for overcoming alternate D-A copolymer energy conversion efficiency bottleneck.In addition to effectively covering the sun Outside spectrum, random ter-polymers also have the advantages that other, as can effectively adjusting, molecular orbit is horizontal, and synthesis is simple, solubility/ Processability is good.It and is wherein even more rare to study the F content on D unit to polymer photovoltaic using ternary polymerization (2D, 1A) The influence of energy.
Summary of the invention
It is an object of the invention to overcome the deficiencies in the prior art, improve a kind of fluoro D-A copolymer of high conversion efficiency.
The fluoro D-A copolymer of high conversion efficiency provided by the invention obtains in the following way:
Using diazosulfide derivative containing F as receptor unit, D1 [5,5'- bis- (tin trimethyl) -2,2'- bithiophene] and D2 [3,4'- bis- fluoro- 5,5'-, bis- (tin trimethyl) -2,2'- bithiophene] is used as donor element, by the method for ternary polymerization, and The ratio for adjusting D1 and D2 synthesizes multiple random. copolymers.
Based on this, the present invention provides following D-A polymer:
Wherein, R=C1-C30Linear chain or branched chain alkyl；
M:n=1:0~0:1.
Preferably, R=C6-C20Alkyl, such as C can be selected from6H13、C9H19、C22H45。
Preferably, m:n=0.8:0.2,0.7:0.3,0.5:0.5,0.3:0.7.
Above-mentioned fluoro D-A polymer, preparation route are as follows according to the present invention:
Wherein, R=C1-C30Linear chain or branched chain alkyl；
D2:D1 molar ratio is 1:0~0:1.
Preferably, R=C6-C20Alkyl, such as C can be selected from6H13、C9H19、C22H45。
Preferably, D2:D1 molar ratio is 0.8:0.2,0.7:0.3,0.5:0.5,0.3:0.7.
The donor element (D1 and D2) of different mol ratio example is added into reactor, receptor unit precursor compound A is (wherein Donor element (D1+D2): the molar ratio of receptor unit A is 1:1), toluene (25mL) dissolution of degassing is added；Then it is added Pd2dba3, CuO, P (o-tolyl)3, then replace two with nitrogen and arrive three times, it is heated the mixture at 110 DEG C under nitrogen protection Reaction 72 hours；End of reaction is cooled to room temperature, and polymer is precipitated in being slowly dropped to methanol；Thick copolymerization is collected by filtration Object, and methanol is used in Soxhlet device, hexane and acetone are purified, and finally extract polymer with chloroform；Chloroformic solution is dense Contracting is slowly added into methanol is precipitated co-polymer again, crosses filter solid and is dried in vacuo, and the target for obtaining red solid produces Object.
Beneficial effects of the present invention are as follows: fluoro D-A polymer prepared by the present invention has excellent thermal stability, photovoltaic The performance test results show in D and A while to introduce F be the method for effectively improving device efficiency；And suitable F on D monomer Content can promote the transfer efficiency of device compared with not fluorine-containing and/or perfluor D monomer to a greater extent, in optimal D monomer F content (D2:D1=0.7:0.3) under situation, fluoro D-A polymer short circuit current of the invention is up to 14.5mA/cm2, highest shows 9.86% transfer efficiency.
Specific embodiment
Below in conjunction with specific embodiment, further detailed description is carried out to the present invention.
The preparation (D2:D1=0:1) of 1 fluoro D-A polymer P -1 of embodiment
Preparation route is as follows:
Donor element D1 and 0.3mmol the receptor unit precursor compound A1 of 0.3mmol is added into reactor, is added The toluene dissolution of 15mL degassing.Then the Pd of 8mg is added2dba3, the P (o-tolyl) of the CuO and 10mg of 50mg3, then use nitrogen Displacement two is heated the mixture at 110 DEG C under nitrogen protection and is reacted 72 hours to three times.End of reaction is cooled to room temperature, Polymer is precipitated in being slowly dropped to methanol.Thick copolymer is collected by filtration, and uses methanol, hexane and third in Soxhlet device Ketone is purified, and finally extracts polymer with chloroform.Chloroformic solution concentration is slowly added into methanol, combined polymerization is precipitated again Object is crossed filter solid and is dried in vacuo, obtains the target product of red solid, yield 83%, Mn=9.08kg.mol-1、MW= 11.35kg.mol-1, PDI=1.25,5% mass loss temperature (Td) it is 315 DEG C.
The preparation (D2:D1=0.3:0.7) of 2 fluoro D-A polymer P -2 of embodiment
Donor element D2 and the 0.3mmol receptor of donor element D1,0.09mmol of 0.21mmol are added into reactor Unit precursor compound A1, remaining operation such as embodiment 1, obtains the target product of red solid, yield 83.6%.Mn= 9.68kg.mol-1、MW=12.45kg.mol-1, PDI=1.29,5% mass loss temperature (Td) it is 352 DEG C.
The preparation (D2:D1=0.5:0.5) of 3 fluoro D-A polymer P -3 of embodiment
Donor element D2 and the 0.3mmol receptor of donor element D1,0.15mmol of 0.15mmol are added into reactor Unit precursor compound A1, remaining operation such as embodiment 1, obtains the target product of red solid, yield 82%.Mn= 10.53kg.mol-1、MW=12.86kg.mol-1, PDI=1.22,5% mass loss temperature (Td) it is 332 DEG C.
The preparation (D2:D1=0.7:0.3) of 4 fluoro D-A polymer P -4 of embodiment
Donor element D2 and the 0.3mmol receptor of donor element D1,0.21mmol of 0.09mmol are added into reactor Unit precursor compound A1, remaining operation such as embodiment 1, obtains the target product of red solid, yield 86.3%.Mn= 12.67kg.mol-1、MW=16.31kg.mol-1, PDI=1.29,5% mass loss temperature (Td) it is 393 DEG C.
The preparation (D2:D1=0.8:0.2) of 5 fluoro D-A polymer P -5 of embodiment
Donor element D2 and the 0.3mmol receptor of donor element D1,0.24mmol of 0.06mmol are added into reactor Unit precursor compound A1, remaining operation such as embodiment 1, obtains the target product of red solid, yield 85.5%.Mn= 12.27kg.mol-1、MW=15.33kg.mol-1, PDI=1.25,5% mass loss temperature (Td) it is 381 DEG C.
The preparation (D2:D1=1:0) of 6 fluoro D-A polymer P -6 of embodiment
Donor element D2 and 0.3mmol the receptor unit precursor compound A1 of 0.3mmol into reactor, remaining operation is such as Embodiment 1 obtains the target product of red solid, yield 84%.Mn=9.52kg.mol-1、MW=11.93kg.mol-1, PDI=1.25,5% mass loss temperature (Td) it is 347 DEG C.
The test of 7 photovoltaic performance of embodiment
Respectively using P-1~P-6 prepared by embodiment 1-6 as electron donor, fullerene PC61BM is done as electron acceptor, The mass ratio of donor and receptor is 1:1.2, applied to preparing photoelectric device, battery structure ITO/PEDOT:PSS/P-n: PC61BM/Ca/Al and efficiency test is carried out under the same conditions.As a result as follows:
P-1:PC61BM: short circuit current 7.21 ± 0.22 (7.42) JSC/mA/cm2；Transfer efficiency PCE*100=3.16 ± 0.18(3.34)。
P-2:PC61BM: short circuit current 9.93 ± 0.26 (10.19) JSC/mA/cm2；Transfer efficiency PCE*100=5.96 ± 0.25(6.21)。
P-3:PC61BM: short circuit current 12.33 ± 0.21 (12.54) JSC/mA/cm2；Transfer efficiency PCE*100=7.56 ± 0.30(7.86)。
P-4:PC61BM: short circuit current 14.1 ± 0.3 (14.50) JSC/mA/cm2；Transfer efficiency PCE*100=9.53 ± 0.33(9.86)。
P-5:PC61BM: short circuit current 13.21 ± 0.22 (13.43) JSC/mA/cm2；Transfer efficiency PCE*100=7.85 ± 0.18(8.03)。
P-6:PC61BM: short circuit current 9.22 ± 0.24 (9.46) JSC/mA/cm2；Transfer efficiency PCE*100=5.15 ± 0.30(5.45)。

Claims (7)

1. a kind of fluoro D-A copolymer, which is characterized in that structural formula is as follows:
Wherein, R C1-C30Linear chain or branched chain alkyl；M:n=0.8:0.2,0.7:0.3,0.5:0.5,0.3:0.7.
2. fluoro D-A copolymer according to claim 1, it is characterised in that: R is preferably C6-C30Linear chain or branched chain Alkyl.
3. fluoro D-A copolymer according to claim 2, which is characterized in that R is preferably C6H13、C9H19、C22H45。
4. fluoro D-A copolymer according to claim 1 to 3, which is characterized in that have the following structure:
5. the preparation method of fluoro D-A copolymer according to claim 1, which is characterized in that preparation route is as follows:
The preparation method operating procedure is as follows: the donor element (D1 and D2) of different mol ratio example is added into reactor, by Body unit precursor compound A (wherein donor element (D1+D2): the molar ratio of receptor unit A is 1:1), is added the toluene of degassing (25mL) dissolution；Then Pd is added2dba3, CuO, P (o-tolyl)3, then replace two with nitrogen and arrive three times, under nitrogen protection will Mixture is heated to react 72 hours at 110 DEG C；End of reaction is cooled to room temperature, by polymer in being slowly dropped to methanol It is precipitated；Thick copolymer is collected by filtration, and uses methanol in Soxhlet device, hexane and acetone are purified, finally extracted with chloroform Polymer；Chloroformic solution concentration is slowly added into methanol, co-polymer is precipitated again, cross filter solid and be dried in vacuo, obtained The target product of red solid.
Wherein, R, m, n are as defined in claim 1；The molar ratio of donor element D2 and D1 be respectively 0.8:0.2, 0.7:0.3、0.5:0.5、0.3:0.7。
6. the fluoro D-A copolymer of -4 any one is applied to solar-electricity as donor material according to claim 1 The purposes in pond.
7. a kind of solar battery, which is characterized in that it is any one that the photoactive layer in battery device structure contains claim 1-4 Fluoro D-A copolymer described in.
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CN105885016A (en) * 2014-12-26 2016-08-24 宁波大学 Synthetic method of narrow band gap terpolymer solar cell donor material

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WO2015100441A1 (en) * 2013-12-26 2015-07-02 Raynergy Tek Incorporation Conjugated polymers and devices incorporating the same
CN105885016A (en) * 2014-12-26 2016-08-24 宁波大学 Synthetic method of narrow band gap terpolymer solar cell donor material

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