CN109749059A - A kind of condensed ring N-shaped polymer of main chain cyano-containing indone and its application - Google Patents
A kind of condensed ring N-shaped polymer of main chain cyano-containing indone and its application Download PDFInfo
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Abstract
The invention belongs to macromolecule photoelectric Material Field, condensed ring N-shaped polymer and its application of a kind of main chain cyano-containing indone are disclosed.Its structural formula are as follows:Wherein, n is the positive integer greater than 3 less than 1,000,000, R1, R2, R3, R4For alkyl chain, A, C are conjugate unit structure, and B is aromatic rings.The condensed ring N-shaped polymer of main chain cyano-containing indone of the invention has very high absorption coefficient, the photoelectric current and battery device efficiency of battery device can be greatlyd improve as electron acceptor；And the condensed ring N-shaped polymer of the main chain cyano-containing indone can reach preferably short circuit current as electron acceptor, open-circuit voltage and fill factor, the all-polymer photovoltaic device that energy conversion efficiency is more than 10% is prepared, far more than the battery performance based on existing receptor.
Description
Technical field
The invention belongs to macromolecule photoelectric Material Field, in particular to the condensed ring N-shaped of a kind of main chain cyano-containing indone polymerize
Object and its application.
Background technique
As the whole world is for the increase year by year of energy demand, the traditional energies such as petroleum, coal it is increasingly depleted, and to guarantor
The needs of ball ecological environment are protected, it is inexhaustible that research is concentrated on hydrogen, solar energy etc. by the more and more scientists in the whole world
Nexhaustible renewable and clean energy resource.
The photovoltaic device based on inorganic material such as mature inorganic silicon, GaAs, indium phosphide accounts on the market
There is leading position, however since its requirement for material purity is high, the problems such as high energy consumption can be generated in process and is polluted,
And its price is very expensive, therefore is pursuing low cost and environmentally protective today, large-scale application is restricted.
Organic photovoltaic devices are as a kind of novel thin film photovoltaic cell technology, with all solid state, photovoltaic material property is adjustable
Range 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 of effect.Organic/polymer photovoltaics can be used the methods of printing, printing and be processed, and can use for reference adding for conventional plastic
Work technique manufactures large area, film photovoltaic device flexible by roll-to-roll rolling processing flow, which can be effective
Reduce the manufacturing cost of photovoltaic cell.Organic photovoltaic devices are hardly limited by environment and place, many occasions can be by luminous energy
Electric energy is converted to, while having very strong complementarity with inorganic semiconductor photovoltaic device, undoubtedly there is huge business development valence
Value and the market competitiveness.Therefore the research of organic photovoltaic devices attracts wide attention, using organic photovoltaic devices as the section of core
Learn the material science research frontier that research has become a worldwide competition fierceness.
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, non-lipid
It strangles alkene to make fast progress, then relatively fewer using conjugated polymer as the report of receptor, efficiency is not also high.The main reason is that existing
Receptor absorption coefficient it is not high, caused by absorption spectrum is not wide enough.By the adjusting for conjugated polymer molecular structure,
It can effectively improve these problems, and improve using conjugated polymer as the performance of the organic photovoltaic devices of receptor.
Summary of the invention
In order to overcome the shortcomings and deficiencies of the prior art described above, the primary purpose of the present invention is that providing a kind of main chain containing cyanogen
The condensed ring N-shaped polymer of base indone.It is made of four parts, the symmetrical conjugate unit of intermediate indeno Dithiophene and both sides and virtue
Fragrant ring and cyano indone and the conjugate unit of connection.
Another object of the present invention is the condensed ring N-shaped polymer for providing above-mentioned main chain cyano-containing indone as electron acceptor material
Expect the application in organic photovoltaic devices.
The purpose of the present invention is realized by following proposal:
A kind of condensed ring N-shaped polymer of main chain cyano-containing indone, has a structure that
Wherein, n is the positive integer greater than 3 less than 1,000,000, R1, R2, R3, R4For alkyl chain, A is conjugate unit, and structure can
For thiophene, furans, benzene, fluorenes, carbazole, silicon fluorene, bithiophene, connection furans, benzene thiophene, two selenophen of benzo, two furans of benzo, pheno
Thiazine, phenoxazine, bithiophene and furans, thiophene pentalene, Thienopyrroles, thieno thiophene cough up, indoles fluorenes, indoles click
Azoles, pyrroles, diazosulfide, selenole, benzoxadiazole, benzotriazole and the above structure derivative one kind；B
It can be benzene for aromatic rings, thiophene, furans, selenophen, pyrroles, thiazole, imidazoles, pyridine, pyrazine, pyrimidine, pyridazine and above structure
Any one in derivative；C is conjugate unit, and structure can be double bond, three keys, thiophene, furans, benzene, fluorenes, carbazole, silicon fluorene, connection
Thiophene, connection furans, benzene thiophene, two selenophen of benzo, two furans of benzo, phenthazine, phenoxazine, bithiophene and furans, thiophene
Pentalene, Thienopyrroles, thieno thiophene cough up, indoles fluorenes, indole carbazole, pyrroles, diazosulfide, selenole,
One kind of the derivative of benzoxadiazole, benzotriazole and the above structure.
Preferably, the R1, R2, R3, R4For straight chain, branch or cyclic alkyl chain with 1~40 carbon atom,
It is either carbon atoms one or more in the straight chain with 1~40 carbon atom, branch or cyclic alkyl chain by oxygen original
Son, alkenyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyano, methyl, ethyl, methoxyl group, nitro replace institute's shape
At group, either be the hydrogen atom in the straight chain with 1~40 carbon atom, branch or cyclic alkyl chain by fluorine original
Son, oxygen atom, alkenyl, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyano, methyl, ethyl, methoxyl group, nitro
Substitution is formed by group.
Preferably, the A can be for flowering structure and with any one in the derivative of flowering structure:
Preferably, the B is with flowering structure and with any one in the derivative of flowering structure:
Preferably, the C is with flowering structure and with any one in the derivative of flowering structure:
The condensed ring N-shaped polymer of above-mentioned main chain cyano-containing indone mainly passes through Stille polymerization reaction and obtains.
The condensed ring N-shaped polymer of above-mentioned main chain cyano-containing indone can be used as electron acceptor in organic photovoltaic devices.
The organic photovoltaic devices structure as shown in Figure 1, by substrate 1, cathode 2, cathode interface layer 3, light absorbing 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, cathode 6 successively
Stacking is constituted.Wherein the receptor of light absorbing layer is made of the condensed ring N-shaped polymer of main chain cyano-containing indone of the invention.
The material of the anode is preferably aluminium, silver, gold, calcium/aluminium alloy, calcium/silver alloy or indium tin oxide target.
The anode interface layer is preferably conjugatd polymers (such as poly- 3,4- ethylenedioxy thiophene/polystyrene sulphur
Hydrochlorate) or inorganic semiconductor (such as MoO3At least one of).
The material of the cathode is preferably metal (such as aluminium), (such as indium tin oxide conductive film (ITO), mixes metal oxide
Miscellaneous stannic oxide (FTO), zinc oxide (ZnO), indium gallium zinc oxide (IGZO)) and graphene and its derivative at least one
Kind.
The cathode interface layer is preferably at least one of PFN-Br, PFN, PNDIT-F3N, PNDIT-F3N-Br.
The substrate is preferably glass, flexible material (such as polyimides, polyethylene terephthalate, ethylene pair
Phthalic acid ester, polyethylene naphthalate or other polyester materials), metal, at least one in alloy and stainless steel film
Kind.
Mechanism of the invention are as follows: can effectively improve the absorption system of polymer by introducing cyano indone on main chain
Number, with small molecular phase ratio, polymer has better stability.
The present invention compared with the existing technology, have the following advantages and the utility model has the advantages that
(1) present invention devises the condensed ring N-shaped polymer of main chain cyano-containing indone, can greatly improve the suction of polymer
Coefficient is received, the photoelectric current and battery device efficiency of battery device can be greatlyd improve；
(2) the condensed ring N-shaped polymer of the main chain cyano-containing indone described in can reach preferably short-circuit as electron acceptor
Electric current, open-circuit voltage and fill factor prepare the all-polymer photovoltaic device that energy conversion efficiency is more than 10%, far more than being based on
The battery performance of existing receptor.
Detailed description of the invention
Fig. 1 is the structural schematic diagram of organic photovoltaic devices.
Fig. 2 is that the ultraviolet-visible light-of the condensed ring N-shaped polymer (P1, P2, P3) of the main chain cyano-containing indone is close red
Outer absorption spectrogram.
Fig. 3 is that ultraviolet-visible light-near-infrared of the condensed ring N-shaped polymer (P4, P5) of the main chain cyano-containing indone is inhaled
Receive spectrogram.
Fig. 4 is battery structure when being ITO cathode/cathode interface layer/active layer/sun machine boundary layer/anode (inverted structure),
The electricity of battery device when the condensed ring N-shaped polymer (P1, P2, P3) of the main chain cyano-containing indone is as electron acceptor material
Stream-voltage curve；
Fig. 5 is battery structure when being ITO cathode/anode boundary layer/active layer/yin machine boundary layer/anode (positive assembling structure),
The electricity of battery device when the condensed ring N-shaped polymer (P1, P2, P3) of the main chain cyano-containing indone is as electron acceptor material
Stream-voltage curve.
Fig. 6 is battery structure when being ITO cathode/cathode interface layer/active layer/sun machine boundary layer/anode (inverted structure),
Electric current-electricity of battery device when the condensed ring N-shaped polymer (P4, P5) of the main chain cyano-containing indone is as electron acceptor material
It buckles line chart.
Specific embodiment
Below with reference to embodiment and attached drawing, the present invention is described in further detail, but embodiments of the present invention are unlimited
In this.
Monomer M1 used in embodiment, M2, M3, M5, M6 according to document [Angewandte Chemie, 2017,56,
13503-13507.] synthesis of method disclosed in；Monomer M4 is according to document [Journal of the American Chemical
Society, 2011,13,1405-1418.] disclosed in method synthesis.Agents useful for same unless otherwise specified can be from embodiment
Market is routinely bought.
Embodiment 1: the preparation of 1~P5 of polymer P
Monomer M1 (0.5mmol) and monomer M4 (0.5mmol) are added in 25mL two mouth flask, nitrogen protection is passed through,
8mL toluene is added.It substitutes gas and 5mg Pd (PPh is added afterwards twice3)4, polymer is precipitated out with methanol after 95 DEG C of reaction 12h,
Washing is three times.Dark polymer P 1, yield 85.7%,1HNMR(CDCl3 500MHz):δ:7.00-7.48(m,18H),
4.13-3.50 (m, 8H), 1.05-1.30 (br, 112H), 0.87 (t, 12H) .GPC:Mn=27.8kDa, Mw=70.3kDa,
PDI=2.53.Elem.Anal.:C, 77.05；H,8.45；N,2.90；O,1.66；S,9.95.Reaction equation is as follows:
Monomer M2 (0.5mmol) and monomer M4 (0.5mmol) are added in 25mL two mouth flask, nitrogen protection is passed through,
12mL toluene is added.It substitutes after 7mg Pd (PPh3) 4,95 DEG C of reaction 12h are added afterwards twice in gas and is settled out polymer with methanol
Come, washing is three times.Dark polymer P 2, yield 84.9%,1HNMR(CDCl3 500MHz):δ:7.02-7.48(m,16H),
4.12-3.60 (m, 14H), 1.06-1.30 (br, 112H), 0.87 (t, 12H) .GPC:Mn=26.8kDa, Mw=59.8kDa,
PDI=2.23. elemental analysis: C, 75.93；H,8.40；N,2.81；O,3.21；S, 9.65. reaction equation are as follows:
Monomer M3 (0.5mmol) and monomer M4 (0.5mmol) 5 are added in 25mL two mouth flask, nitrogen protection is passed through,
11mL toluene is added.It substitutes gas and 4mg Pd (PPh is added afterwards twice3)4, polymer is settled out with methanol after 95 DEG C of reaction 12h
Come, washing is three times.Obtain dark polymer P 3, yield 85.2%1HNMR(CDCl3 500MHz):δ:7.24-7.46(m,16H),
4.12-3.62 (m, 8H), 1.07-1.31 (br, 112H), 0.88 (t, 12H) .GPC:Mn=28.8kDa, Mw=81.5kDa,
PDI=2.83. elemental analysis: C, 75.64；H,8.19；F,1.93；N,2.85；O,1.63；S, 9.77. reaction equation are as follows:
Monomer M5 (0.5mmol) and monomer M4 (0.5mmol) are added in 25mL two mouth flask, nitrogen protection is passed through,
11mL toluene is added.It substitutes gas and 3mg Pd (PPh is added afterwards twice3)4, polymer is settled out with methanol after 95 DEG C of reaction 12h
Come, washing is three times.Dark polymer P 4, yield 83.1%,1HNMR(CDCl3 500MHz):δ:7.02-7.46(m,14H),
4.12-3.62 (m, 8H), 1.07-1.31 (br, 112H), 0.88 (t, 12H) .GPC:Mn=27.8kDa, Mw=73.1kDa,
PDI=2.63. elemental analysis: C, 74.10；H,8.19；N,2.88；O,1.65；S, 13.19. reaction equation are as follows:
Monomer M6 (0.5mmol) and monomer M4 (0.5mmol) 5 are added in 25mL two mouth flask, nitrogen protection is passed through,
11mL toluene is added.It substitutes gas and 4mg Pd (PPh is added afterwards twice3)4, polymer is settled out with methanol after 95 DEG C of reaction 12h
Come, washing is three times.Obtain dark polymer P 5, yield 84.5%.1HNMR(CDCl3 500MHz):δ:7.00-7.48(m,12H),
4.14-3.60 (m, 8H), 1.05-1.31 (br, 112H), 0.87 (t, 12H) .GPC:Mn=29.8kDa, Mw=65.3kDa,
PDI=2.23. elemental analysis: C, 72.75；H,7.94；F,1.92；N,2.83；O,1.62；S, 12.95. reaction equation are as follows:
Obtained polymer is carried out to the measurement of the absorption spectrum of solution, as a result as shown in Figures 2 and 3.From the dense of solution
Degree (0.02mg/ml) and measured absorption value can calculate polymer P 1, P2, P3, P4, the absorption coefficient of P5.P1,P2,
The absorption coefficient of P3, P4, P5 at top is respectively 4.37*106cm-1, 4.21*106cm-1,4.23*106cm-1,4.45*
106cm-1And 4.19*106cm-1, illustrate that the polymer of this invention has very high absorption coefficient, be conducive to the absorption to light.
Embodiment 2: polymer P 1, P2, P3 (AB component is identical in structure) are as electron acceptor in organic photovoltaic devices
Application in (ITO cathode/cathode interface layer/active layer/sun machine boundary layer/anode)
By ITO electro-conductive glass, square resistance~20 Europe/square centimeter, 15 millimeters × 15 millimeters square pieces of pre-cut.Successively use
Acetone, micron level semiconductor special purpose detergent, deionized water, isopropanol ultrasonic cleaning, nitrogen is blown a whistle, and to be placed on constant temperature oven standby
With.The PFN-Br that one layer of 5nm thickness of Tu is revolved on ITO, is then spin coated onto active layer material PTB7-Th/P1, PTB7-Th/P2, PTB7-
Th/P3 (wherein the mass ratio of donor PTB7-Th and receptor is 1:2), with a thickness of 110 nanometers, is finally deposited MoO3With Al electricity
Pole.All preparation process carry out in the glove box for providing nitrogen atmosphere.The current-voltage of prepared upside-down mounting battery device
Curve is as shown in figure 4, relevant data are shown in Table 1.As can be seen that the condensed ring N-shaped of main chain cyano-containing indone of the present invention is poly-
The electric current of battery device can be greatlyd improve by closing object, improve battery efficiency.Mainly in fill factor, short circuit current and open
Road voltage has reached good balance.
Embodiment 3: polymer P 1, P2, P3 (AB component is identical in structure) are as electron acceptor in organic photovoltaic devices
Application in (ito anode/anode interface layer/active layer/yin machine boundary layer/cathode)
By ITO electro-conductive glass, square resistance~20 Europe/square centimeter, 15 millimeters × 15 millimeters square pieces of pre-cut.Successively use
Acetone, micron level semiconductor special purpose detergent, deionized water, isopropanol ultrasonic cleaning, nitrogen is blown a whistle, and to be placed on constant temperature oven standby
With.The PEDOT:PSS (poly- 3,4-ethylene dioxythiophene/poly styrene sulfonate) that one layer of 20nm thickness of Tu is revolved on ITO, then revolves
Active layer material PTB7-Th/P1 is applied, (wherein the mass ratio of donor PTB7-Th and receptor is equal by PTB7-Th/P2, PTB7-Th/P3
For 1:2), thickness is 100 nanometers.It is then spin coated onto the PFN-Br of one layer of 5nm thickness, last evaporating Al electrode.All preparation process
Carried out in the glove box that nitrogen atmosphere is provided.The current -voltage curve of prepared formal dress battery device as shown in figure 5,
Relevant data are shown in Table 1.As can be seen that the condensed ring N-shaped polymer of main chain cyano-containing indone of the present invention can be greatly
The electric current of battery device is improved, and fill factor is also higher, device efficiency reaches as high as 10.33%.
Embodiment 4: polymer P 4, P5 (AB component is different in structure) are as electron acceptor in organic photovoltaic devices (ITO sun
Pole/anode interface layer/active layer/yin machine boundary layer/cathode) in application
By ITO electro-conductive glass, square resistance~20 Europe/square centimeter, 15 millimeters × 15 millimeters square pieces of pre-cut.Successively use
Acetone, micron level semiconductor special purpose detergent, deionized water, isopropanol ultrasonic cleaning, nitrogen is blown a whistle, and to be placed on constant temperature oven standby
With.The PEDOT:PSS that one layer of 20nm thickness of Tu is revolved on ITO, is then spin coated onto active layer material PTB7-Th/P4, PTB7-Th/P5
(mass ratio of donor and receptor is 1:2), thickness is 100 nanometers.It is then spin coated onto the PFN-Br of one layer of 5nm thickness, is finally steamed
Plate Al electrode.All preparation process carry out in the glove box for providing nitrogen atmosphere.The electricity of prepared formal dress battery device
Stream-voltage curve is as shown in fig. 6, relevant data are shown in Table 1.As can be seen that main chain cyano-containing indone of the present invention is thick
Ring N-shaped polymer can greatly improve the electric current of battery device, and fill factor is also higher, and device efficiency reaches as high as
10.34%.
The performance parameter of organic photovoltaic devices when table 1 P1, P2, P3, P4, P5 are as electron acceptor material
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, other any changes, modifications, substitutions, combinations, simplifications made without departing from the spirit and principles of the present invention,
It should be equivalent substitute mode, be included within the scope of the present invention.
Claims (9)
1. a kind of condensed ring N-shaped polymer of main chain cyano-containing indone, it is characterised in that have a structure that
Wherein, n is the positive integer greater than 3 less than 1,000,000, R1, R2, R3, R4For alkyl chain, A, C are conjugate unit structure, and B is virtue
Fragrant ring.
2. the condensed ring N-shaped polymer of main chain cyano-containing indone according to claim 1, it is characterised in that:
The R1, R2, R3, R4For the straight chain with 1~40 carbon atom, branch perhaps cyclic alkyl chain or be the tool
Have in the straight chain, branch or cyclic alkyl chain of 1~40 carbon atom one or more carbon atoms by oxygen atom, alkenyl, alkynyl,
Aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyano, methyl, ethyl, methoxyl group, nitro substitution are formed by group, or
It is the hydrogen atom in the straight chain with 1~40 carbon atom, branch or cyclic alkyl chain by fluorine atom, oxygen atom, alkene
Base, alkynyl, aryl, hydroxyl, amino, carbonyl, carboxyl, ester group, cyano, methyl, ethyl, methoxyl group, nitro substitution are formed by
Group.
3. the condensed ring N-shaped polymer of main chain cyano-containing indone according to claim 1, it is characterised in that:
The conjugate unit A is thiophene, furans, benzene, fluorenes, carbazole, silicon fluorene, bithiophene, connection furans, benzene thiophene, benzo
Two selenophens, two furans of benzo, phenthazine, phenoxazine, bithiophene and furans, thiophene pentalene, Thienopyrroles, thiophene
And thiophene is coughed up, indoles fluorenes, indole carbazole, pyrroles, diazosulfide, selenole, benzoxadiazole, benzotriazole and
Thiophene, furans, benzene, fluorenes, carbazole, silicon fluorene, bithiophene, connection furans, benzene thiophene, two selenophen of benzo, two furans of benzo, pheno thiophene
Piperazine, phenoxazine, bithiophene and furans, thiophene pentalene, Thienopyrroles, thieno thiophene cough up, indoles fluorenes, indole carbazole,
Pyrroles, diazosulfide, selenole, benzoxadiazole, benzotriazole derivative one kind；
The aromatic rings B be benzene, thiophene, furans, selenophen, pyrroles, thiazole, imidazoles, pyridine, pyrazine, pyrimidine, pyridazine and
Benzene, thiophene, furans, selenophen, pyrroles, thiazole, imidazoles, pyridine, pyrazine, pyrimidine, pyridazine derivative in any one；
The conjugate unit C is double bond, three keys, thiophene, furans, benzene, fluorenes, carbazole, silicon fluorene, bithiophene, connection furans, benzo two
Thiophene, two selenophen of benzo, two furans of benzo, phenthazine, phenoxazine, bithiophene and furans, thiophene pentalene, thieno
Pyrroles, thieno thiophene cough up, indoles fluorenes, indole carbazole, pyrroles, diazosulfide, selenole, benzoxadiazole, benzo three
Nitrogen azoles and double bond, three keys, thiophene, furans, benzene, fluorenes, carbazole, silicon fluorene, bithiophene, connection furans, benzene thiophene, benzo two
Selenophen, two furans of benzo, phenthazine, phenoxazine, bithiophene and furans, thiophene pentalene, Thienopyrroles, thieno
Thiophene coughs up, indoles fluorenes, indole carbazole, pyrroles, diazosulfide, selenole, benzoxadiazole, benzotriazole derivative
One kind.
4. the condensed ring N-shaped polymer of main chain cyano-containing indone according to claim 1, it is characterised in that:
The conjugate unit structure A is in flowering structure and with any one in the derivative of flowering structure:
5. the condensed ring N-shaped polymer of main chain cyano-containing indone according to claim 1, it is characterised in that:
The aromatic ring structure B is with flowering structure and with any one in the derivative of flowering structure:
6. the condensed ring N-shaped polymer of main chain cyano-containing indone according to claim 1, it is characterised in that:
The conjugate unit structure C is with flowering structure and with any one in the derivative of flowering structure:
7. the condensed ring N-shaped polymer of described in any item main chain cyano-containing indones is in organic photovoltaic devices according to claim 1~6
In application.
8. application of the condensed ring N-shaped polymer of main chain cyano-containing indone according to claim 7 in organic photovoltaic devices,
It is characterized by:
The organic photovoltaic devices structure is by substrate 1, cathode 2, cathode interface layer 3, light absorbing layer 4, anode interface layer 5, sun
Pole 6 is stacked gradually and is constituted by substrate 1, anode 2, anode interface layer 3, light absorbing layer 4, cathode interface layer 5, cathode 6, wherein light
Absorbed layer is made of the condensed ring N-shaped polymer of the described in any item main chain cyano-containing indone of claim 1~6.
9. application of the condensed ring N-shaped polymer of main chain cyano-containing indone according to claim 8 in organic photovoltaic devices,
It is characterized by:
The material of the anode is aluminium, silver, gold, calcium/aluminium alloy, calcium/silver alloy or indium tin oxide target；
The anode interface layer is at least one of conjugatd polymers or inorganic semiconductor；
The material of the cathode is metal, metal oxide and at least one of graphene and its derivative；
The cathode interface layer is at least one of PFN-Br, PFN, PNDIT-F3N, PNDIT-F3N-Br；
The substrate is at least one of glass, flexible material, metal, alloy and stainless steel film.
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| CN112778335A (en) * | 2019-11-04 | 2021-05-11 | 华南协同创新研究院 | Oxadiazole indolopyrrole-containing fused ring compounds and preparation method and application thereof |
| JP2021163811A (en) * | 2020-03-31 | 2021-10-11 | 三菱ケミカル株式会社 | Organic semiconductor device |
| JP2021163810A (en) * | 2020-03-31 | 2021-10-11 | 三菱ケミカル株式会社 | Organic semiconductor device |
| CN113817142A (en) * | 2021-10-13 | 2021-12-21 | 福州大学 | Fluorenyl cyano indanone conjugated polymer and preparation method thereof |
| WO2023105209A1 (en) * | 2021-12-06 | 2023-06-15 | Oxford University Innovation Limited | Novel compounds |
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| JP2021163811A (en) * | 2020-03-31 | 2021-10-11 | 三菱ケミカル株式会社 | Organic semiconductor device |
| JP2021163810A (en) * | 2020-03-31 | 2021-10-11 | 三菱ケミカル株式会社 | Organic semiconductor device |
| CN111883660A (en) * | 2020-08-26 | 2020-11-03 | 中国科学院重庆绿色智能技术研究院 | Fluorinated fused ring electron acceptor-based oligomer small-molecule solar cell and preparation method thereof |
| CN113817142A (en) * | 2021-10-13 | 2021-12-21 | 福州大学 | Fluorenyl cyano indanone conjugated polymer and preparation method thereof |
| CN113817142B (en) * | 2021-10-13 | 2022-06-14 | 福州大学 | Fluorenyl cyano indanone conjugated polymer and preparation method thereof |
| WO2023105209A1 (en) * | 2021-12-06 | 2023-06-15 | Oxford University Innovation Limited | Novel compounds |
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