CN107778457A - Based on even the n-type conjugated polymer of furans and its application in organic electro-optic device - Google Patents

Based on even the n-type conjugated polymer of furans and its application in organic electro-optic device Download PDF

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CN107778457A
CN107778457A CN201710836019.3A CN201710836019A CN107778457A CN 107778457 A CN107778457 A CN 107778457A CN 201710836019 A CN201710836019 A CN 201710836019A CN 107778457 A CN107778457 A CN 107778457A
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conjugated polymer
furans
polymer
chain
type conjugated
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黄飞
胡志诚
应磊
曹镛
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South China University of Technology SCUT
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Abstract

The present invention relates to based on even the n-type conjugated polymer of furans and its application in organic electro-optic device.Described conjugated polymer is made up of two parts, and benzene-naphthalene diimide and substitution connect furans conjugated structure.The conjugated polymer has wider absorption spectrum and absorption coefficient and higher electron mobility, efficient electron acceptor can be used as to be used in efficiency organic photovoltaic device.The present invention devises the n-type semiconductor conjugated polymer of D A copolymerization, can be greatly enhanced the absorption coefficient of polymer, widen absorption spectrum, can be greatly enhanced the photoelectric current and battery device efficiency of battery device；Described new n-type conjugated polymer can reach the balance of short circuit current, open-circuit voltage and fill factor, curve factor as electron acceptor, prepare all-polymer photovoltaic device of the energy conversion efficiency more than 10%, exceed well over the battery performance based on existing acceptor.

Description

Based on even the n-type conjugated polymer of furans and its application in organic electro-optic device
Technical field
The present invention relates to macromolecule photoelectric Material Field, and in particular to sub- for even furans and naphthoyl based on a kind of backbone structure The n-type conjugated polymer of amine copolymer and its application in organic electro-optic device.
Background technology
As the whole world is for the increasingly depleted of the traditional energy such as increase year by year, oil, coal of energy demand, and to protecting The needs of ball ecological environment are protected, it is inexhaustible that research is concentrated on hydrogen, solar energy etc. by the increasing scientist in the whole world Nexhaustible renewable and clean energy resource.
The photovoltaic device based on inorganic material such as ripe inorganic silicon, GaAs, indium phosphide commercially accounts for There is leading position, it is high yet with its requirement for material purity, the problems such as high energy consumption can be produced in process and is polluted, And its price is very expensive, therefore inexpensive and green today is being pursued, its large-scale application is restricted.
Organic photovoltaic devices have that all solid state, photovoltaic material property is adjustable as a kind of novel thin film photovoltaic cell technology Scope is wide, translucent, flexible battery can be achieved, has outstanding advantages of large area low cost prepares potentiality.The light of organic material It is wide to lie prostrate performance adjustable extent, has using chemical means to performances such as the energy level of material, carrier mobility and absorptions The regulation and control of effect.Organic/polymer photovoltaics can use the methods of printing, printing to be processed, and can use for reference adding for conventional plastic Work technique, work flow is rolled by volume to volume and manufactures large area, flexible film photovoltaic device, the production technology can be effective Reduce the manufacturing cost of photovoltaic cell.Organic photovoltaic devices are hardly limited by environment and place, can be by luminous energy in many occasions Electric energy is converted to, while has very strong complementarity with inorganic semiconductor photovoltaic device, undoubtedly with huge business development valency Value and the market competitiveness.Therefore the research of organic photovoltaic devices attracts wide attention, the section using organic photovoltaic devices as core Learn research and have become the fierce material science research frontier of a worldwide competition.
The Advance in Receptor of organic photovoltaic devices is slow, and the research of early stage is based on fullerene.Most over the past two years, it is non-lipid Strangle alkene to make fast progress, then relatively fewer as the report of acceptor using conjugated polymer, efficiency is not also high.Its main cause is existing Acceptor absorption coefficient it is not high, caused by absorption spectrum is not wide enough.By the regulation for conjugated polymer molecular structure, These problems can effectively be improved, and improve the performance using conjugated polymer as the organic photovoltaic devices of acceptor.
The content of the invention
It is an object of the invention to design and synthesize a kind of backbone structure as even furans and the n-type conjugation of naphthalimide copolymerization Polymer is used for organic photovoltaic devices as electron acceptor material.
Technical solution of the present invention is as follows.
It is as follows based on the n-type conjugated polymer of even furans, the polymer architecture：
Wherein, n is positive integer less than 1,000,000, R1, R2For alkyl chain.
Further, described R1、R2It is described for the straight chain with 1~40 carbon atom, side chain or cyclic alkyl chain One or more carbon atoms are by oxygen atom, alkenyl, alkynyl, aryl, hydroxyl, amino, carbonyl in straight chain, side chain or cyclic alkyl chain Base, carboxyl, ester group, cyano group, methyl, ethyl, methoxyl group, nitro substitution；Hydrogen is former in the straight chain, side chain or cyclic alkyl chain Son is substituted by fluorine atom or above-mentioned functional group；The R1、R2For identical group or differ group.
Further, R3, R4, R5, R6For hydrogen, fluorine, chlorine, bromine, iodine atom or be the straight chain with 1~40 carbon atom, Side chain or cyclic alkyl chain；
Further, in the straight chain, side chain or cyclic alkyl chain one or more carbon atoms by oxygen atom, alkenyl, Alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyano group, methyl, ethyl, methoxyl group, nitro substitution；The straight chain, branch Hydrogen atom is substituted by fluorine atom or above-mentioned functional group in chain or cyclic alkyl chain.
Backbone structure is used for organic photovoltaic for even furans and the n-type conjugated polymer of naphthalimide copolymerization as electron acceptor In device.
Conjugated polymer of the present invention is made up of two parts, and benzene-naphthalene diimide and substitution connect furans conjugated structure.It is described common Conjugated polymer has wider absorption spectrum and absorption coefficient and higher electron mobility, can be used as efficient electron acceptor For in efficiency organic photovoltaic device.The present invention devises the n-type semiconductor conjugated polymer of D-A copolymerization, can greatly carry The absorption coefficient of high polymer, widens absorption spectrum, can be greatly enhanced the photoelectric current and battery device effect of battery device Rate；Described new n-type conjugated polymer can reach short circuit current as electron acceptor, open-circuit voltage and fill factor, curve factor it is flat Weighing apparatus, prepares all-polymer photovoltaic device of the energy conversion efficiency more than 10%, exceeds well over the battery performance based on existing acceptor.
The n-type conjugated polymer of new D-A structure of the present invention is obtained by Suzuki or Stille polymerisations.
The organic photovoltaic devices structure used in the present invention is as shown in figure 1, by substrate 1, negative electrode 2, cathode interface layer 3, light Absorbed layer 4, anode interface layer 5, anode 6 or by substrate 1, anode 2, anode interface layer 3, light absorbing layer 4, cathode interface layer 5, cloudy Pole 6 stacks gradually composition.The conjugated polymer that light absorbing layer acceptor is synthesized by the present invention forms.
In photovoltaic device of the present invention, anode material is preferably aluminium, silver, gold, calcium/aluminium alloy or calcium/silver alloy.
Anode interface layer of the present invention is preferably conjugatd polymerses (such as poly- 3,4- ethylenedioxy thiophenes/polyphenyl second Alkene sulfonate) or inorganic semiconductor.
Negative electrode of the present invention is preferably metal, metal oxide (such as indium tin oxide conductive film (ITO), doping titanium dioxide Tin (FTO), zinc oxide (ZnO), indium gallium zinc oxide (IGZO)) and at least one of graphene and its derivative.
Substrate of the present invention is preferably glass, flexible material (such as polyimides, polyethylene terephthalate, second Alkene terephthalate, PEN or other polyester materials), metal, in alloy and stainless steel film extremely Few one kind.
Compared with prior art, the present invention has advantages below：
(1) present invention devises the alternate n-type semiconductor conjugated polymers of D-A, can be greatly enhanced the suction of polymer Coefficient is received, absorption spectrum is widened, the photoelectric current and battery device efficiency of battery device can be greatly enhanced；
(2) the n-type conjugated polymer of the new D-A structure described in can reach short circuit current as electron acceptor, open circuit The balance of voltage and fill factor, curve factor, all-polymer photovoltaic device of the energy conversion efficiency more than 10% is prepared, exceeded well over based on existing There is the battery performance of acceptor.
Brief description of the drawings
Fig. 1 organic photovoltaic devices structural representations；
The ultraviolet-visible light of the n-type conjugated polymer (P1, P2, P3) of new D-A structure described in Fig. 2 representativenesses-near red Outer absorption spectrogram；
Ultraviolet-visible light-near-infrared of the n-type conjugated polymer (P4, P5) of new D-A structure described in Fig. 3 representativenesses Absorb spectrogram；
When Fig. 4 battery structures are ITO negative electrodes/cathode interface layer/active layer/positive machine boundary layer/anode (inverted structure), generation The current -voltage curve of battery device when the conjugated polymer (P1, P2, P3) that table is invented containing this is as electron acceptor material Figure；
When Fig. 5 battery structures are ITO cathode/anodes boundary layer/active layer/cloudy machine boundary layer/anode (positive assembling structure), generation The current -voltage curve of battery device when the conjugated polymer (P1, P2, P3) that table is invented containing this is as electron acceptor material Figure.
When Fig. 6 battery structures are ITO negative electrodes/cathode interface layer/active layer/positive machine boundary layer/anode (inverted structure), generation The current -voltage curve figure of battery device when the conjugated polymer (P4, P5) that table is invented containing this is as electron acceptor material.
Embodiment
Below by specific embodiment, the present invention is further illustrated, and its object is to help to be better understood from this hair Bright content, specifically include synthesis, sign and device and prepare, but these specific embodiments are not limit the invention in any way Protection domain.
Embodiment 1
Representative synthetic route is as follows：
(1) monomer M1, M5 are according to document [Journal of Materials Chemistry C, 2015,3 (34): 8904-8915.] disclosed in method synthesis.
(2) monomer M2, M3, M4, M6, M7 are according to document [Journal of the American Chemical Society,2011,133(5):1405-1418.] disclosed in method synthesis.
(3) polymer P 1, P2, P3 synthesis：
Monomer M1 (0.5mmol) and monomer M2 (0.5mmol) are added in two mouthfuls of flasks of 25mL, are passed through nitrogen protection, Add 8mL toluene.Substitute gas and add 5mg Pd (PPh afterwards twice3)4, 95 DEG C reaction 12h after polymer is settled out with methanol Come, washing is three times.Obtain dark polymer P 1, yield 90.7%.
Monomer M1 (0.5mmol) and monomer M3 (0.5mmol) are added in two mouthfuls of flasks of 25mL, are passed through nitrogen protection, Add 12mL toluene.Substitute gas and add 7mg Pd (PPh afterwards twice3)4, 95 DEG C reaction 12h after polymer is settled out with methanol Come, washing is three times.Obtain dark polymer P 2, yield 87.9%.
Monomer M1 (0.5mmol) and monomer M4 (0.5mmol) 5 are added in two mouthfuls of flasks of 25mL, are passed through nitrogen protection, Add 11mL toluene.Substitute gas and add 4mg Pd (PPh afterwards twice3)4, 95 DEG C reaction 12h after polymer is settled out with methanol Come, washing is three times.Obtain dark polymer P 3, yield 92.2%.
(5) polymer P 4, P5 synthesis
Monomer M5 (0.5mmol) and monomer M6 (0.5mmol) are added in two mouthfuls of flasks of 25mL, are passed through nitrogen protection, Add 11mL toluene.Substitute gas and add 3mg Pd (PPh afterwards twice3)4, 95 DEG C reaction 12h after polymer is settled out with methanol Come, washing is three times.Obtain dark polymer P 4, yield 91.1%.
Monomer M5 (0.5mmol) and monomer M7 (0.5mmol) 5 are added in two mouthfuls of flasks of 25mL, are passed through nitrogen protection, Add 11mL toluene.Substitute gas and add 4mg Pd (PPh afterwards twice3)4, 95 DEG C reaction 12h after polymer is settled out with methanol Come, washing is three times.Obtain dark polymer P 5, yield 89.3%.
The polymer of gained is carried out to the measure of the absorption spectrum of solution, as shown in Figures 2 and 3.From the concentration of solution and Measured absorption value can calculate polymer P 1, P2, P3 absorption coefficient.The absorption of P1, P2, P3, P4, P5 at top Coefficient is respectively 1.37*105cm-1, 1.21*105cm-1,1.23*105cm-1,1.45*105cm-1And 1.19*105cm-1
Embodiment 2
Having with the conjugated polymer P1, P2, P3 (AB components are identical in structure) synthesized by embodiment 1 as electron acceptor Applied in machine photovoltaic device (ITO negative electrodes/cathode interface layer/active layer/positive machine boundary layer/anode)
By ITO electro-conductive glass, square resistance~20 Europe/square centimeter, 15 millimeters × 15 millimeters square pieces of pre-cut.Use successively Acetone, micron level semiconductor special purpose detergent, deionized water, isopropanol are cleaned by ultrasonic, and it is standby that nitrogen is placed in constant temperature oven after blowing a whistle With.The thick PFN-Br of one layer of 5nm of Tu are revolved on ITO, are then spin coated onto active layer material PTB7-Th/P1, PTB7-Th/P2, PTB7-Th/P3, thickness are 110 nanometers, and MoO is finally deposited3With Al electrodes.All preparation process are providing nitrogen atmosphere Carried out in glove box.The current -voltage curve of prepared upside-down mounting battery device as shown in figure 4, related data in Table 1 List.As can be seen that the n-type conjugated polymer of Novel connection furan structure of the present invention can be greatly enhanced battery device Electric current, improve battery efficiency.Mainly good balance is reached in fill factor, curve factor, short circuit current and open-circuit voltage.Device Part performance exceedes best values (the Energy Environ.Sci., 2017,10,1243-1251 reported at present；Adv.Mater. 2016,28,1884–1890)。
Embodiment 3
Having with the conjugated polymer P1, P2, P3 (AB components are identical in structure) synthesized by embodiment 1 as electron acceptor Applied in machine photovoltaic device (ito anode/anode interface layer/active layer/cloudy machine boundary layer/negative electrode)
By ITO electro-conductive glass, square resistance~20 Europe/square centimeter, 15 millimeters × 15 millimeters square pieces of pre-cut.Use successively Acetone, micron level semiconductor special purpose detergent, deionized water, isopropanol are cleaned by ultrasonic, and it is standby that nitrogen is placed in constant temperature oven after blowing a whistle With.The thick PEDOT of one layer of 20nm of Tu are revolved on ITO:PSS, active layer material PTB7-Th/P1, PTB7-Th/P2 are then spin coated onto, PTB7-Th/P3, thickness are 100 nanometers.It is then spin coated onto the thick PFN-Br of one layer of 5nm, last evaporating Al electrode.All preparations Process is carried out in the glove box for providing nitrogen atmosphere.Current -voltage curve such as Fig. 5 of prepared formal dress battery device Shown, related data are listed in Table 1.As can be seen that the n-type conjugated polymer energy of even furan structure of the present invention The electric current of battery device is enough greatly enhanced, and fill factor, curve factor is also higher, and device efficiency reaches as high as 10.92%.
Embodiment 4
With the conjugated polymer P4, P5 (AB components are different in structure) synthesized by embodiment 1 as electron acceptor organic Photovoltaic device
Applied in (ito anode/anode interface layer/active layer/cloudy machine boundary layer/negative electrode)
By ITO electro-conductive glass, square resistance~20 Europe/square centimeter, 15 millimeters × 15 millimeters square pieces of pre-cut.Use successively Acetone, micron level semiconductor special purpose detergent, deionized water, isopropanol are cleaned by ultrasonic, and it is standby that nitrogen is placed in constant temperature oven after blowing a whistle With.The thick PEDOT of one layer of 20nm of Tu are revolved on ITO:PSS, active layer material PTB7-Th/P4, PTB7-Th/P5 are then spin coated onto, PTB7-Th/P3, thickness are 100 nanometers.It is then spin coated onto the thick PFN-Br of one layer of 5nm, last evaporating Al electrode.All preparations Process is carried out in the glove box for providing nitrogen atmosphere.Current -voltage curve such as Fig. 5 of prepared formal dress battery device It is shown, list shown in related datagram 6 and in Table 1.As can be seen that the new n containing quinoid structure of the present invention Type conjugated polymer can be greatly enhanced the electric current of battery device, and fill factor, curve factor is also higher, and device efficiency reaches as high as 10.64%.
When 1 representative conjugated polymer of table is as electron acceptor material, the performance parameter of organic photovoltaic devices
The above embodiment of the present invention is only intended to clearly illustrate example of the present invention, and is not to the present invention Embodiment restriction.For those of ordinary skill in the field, can also make on the basis of the above description Other various forms of changes or variation.There is no necessity and possibility to exhaust all the enbodiments.It is all the present invention All any modification, equivalent and improvement made within spirit and principle etc., should be included in the protection of the claims in the present invention Within the scope of.

Claims (5)

1. the n-type conjugated polymer based on even furans, it is characterised in that the polymer architecture is as follows：
Wherein, n is positive integer less than 1,000,000, R1, R2For alkyl chain.
2. the n-type conjugated polymer according to claim 1 based on even furans, it is characterised in that described R1、R2For with 1 Straight chain, side chain or the cyclic alkyl chain of~40 carbon atoms, it is one or more in the straight chain, side chain or cyclic alkyl chain Carbon atom is by oxygen atom, alkenyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyano group, methyl, ethyl, methoxyl group, Nitro substitutes；Hydrogen atom is substituted by fluorine atom or above-mentioned functional group in the straight chain, side chain or cyclic alkyl chain；The R1、R2 For identical group or differ group.
3. the n-type conjugated polymer according to claim 1 based on even furans, it is characterised in that R3, R4, R5, R6For hydrogen, fluorine, Chlorine, bromine, iodine atom are either the straight chain with 1~40 carbon atom, side chain or cyclic alkyl chain.
4. according to claim 3 based on even furans n-type conjugated polymer, it is characterised in that the straight chain, side chain or In cyclic alkyl chain one or more carbon atoms by oxygen atom, alkenyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, Cyano group, methyl, ethyl, methoxyl group, nitro substitution；In the straight chain, side chain or cyclic alkyl chain hydrogen atom by fluorine atom or Above-mentioned functional group's substitution.
5. the n-type conjugated polymer based on even furans according to claim any one of 1-4 is used for organic as electron acceptor In photovoltaic device.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108727568A (en) * 2018-06-08 2018-11-02 福建师范大学 Crosslinkable full polymers solar cell acceptor material based on benzene-naphthalene diimide, preparation method and applications
CN113087875A (en) * 2021-03-25 2021-07-09 河南大学 Water/alcohol soluble full furan polymer material, preparation method and application thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105542131A (en) * 2016-01-29 2016-05-04 中国科学院长春应用化学研究所 Conjugated polymer containing boron and preparation method and application thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105542131A (en) * 2016-01-29 2016-05-04 中国科学院长春应用化学研究所 Conjugated polymer containing boron and preparation method and application thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
JIANGUO MEI ET AL.: "Effect of Spacer Length of Siloxane-Terminated Side Chains on Charge Transport in Isoindigo-Based Polymer Semiconductor Thin Films", 《ADVANCED FUNCTIONAL MATERIALS》 *
RUKIYA MATSIDIK ET AL.: "Highly Planarized Naphthalene Diimide–Bifuran Copolymers with Unexpected Charge Transport Performance", 《CHEMISTRY OF MATERIALS》 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108727568A (en) * 2018-06-08 2018-11-02 福建师范大学 Crosslinkable full polymers solar cell acceptor material based on benzene-naphthalene diimide, preparation method and applications
CN113087875A (en) * 2021-03-25 2021-07-09 河南大学 Water/alcohol soluble full furan polymer material, preparation method and application thereof

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