CN106565939A - Semi-conducting polymers capable of electronic printing and applications thereof - Google Patents
Semi-conducting polymers capable of electronic printing and applications thereof Download PDFInfo
- Publication number
- CN106565939A CN106565939A CN201510651847.0A CN201510651847A CN106565939A CN 106565939 A CN106565939 A CN 106565939A CN 201510651847 A CN201510651847 A CN 201510651847A CN 106565939 A CN106565939 A CN 106565939A
- Authority
- CN
- China
- Prior art keywords
- semi
- hexyl
- polymers
- octyl
- decyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
Semi-conducting polymers used for electronic printing are disclosed. The general structure of the polymers is shown as SCP-1M-00, wherein R1 is C1-C40 alkyl, R2 is C1-C30 alkyl, and n is a positive integer greater than 10. Film formed by a solution of the polymers and applications of the polymers in organic photovoltaic devices are also disclosed. Solubility of the polymers in common organic solvents is high, thus laying a foundation for electronic printing, and allowing the film formed by the solution of the polymers to have better morphology and to acquire a higher charge migration rate. In addition, the polymers have a polymer skeleton in which benzo[1,2-b:4,5-b']dithiophene and 4,7-bis(4-alkyl-2-thienyl)-(5,6-difluoro-2,1,3- benzothiadiazole) are alternatively connected, and therefore LUMO and HOMO energy levels are optimized, and the organic photovoltaic devices manufactured from the polymers have higher phototransformation efficiencies.
Description
Technical field
The present invention relates to a kind of semi-conducting polymer and its application for electronic printable.
Background technology
Semi-conducting polymer is the conjugated polymer that a class at least replaces main chain containing a single double bond, due to Dan Shuan
Key is alternatively formed the i.e. single double bond of Pz tracks generation centreization of π track carbon atoms becomes similar, double bond overlapping portion
Divide and be equally also covered on singly-bound, pi-electron is easier to be moved to another key from a key so that conjugation is poly-
Compound becomes a class organic semiconductor.
Semi-conducting polymer dissolves in organic solvent, therefore the method for printing can be used to prepare organic based device.
Electronic printable equipment is also referred to as using the equipment that organic semiconducting materials are printed, electronic printable increasingly causes
Art research and the interest of industrial business.Especially as the rise of nearest low band gaps polymer, partly led using these
Body polymer prepares organic photovoltaic devices (OPV or polymer solar battery PSC) and causes extensive pass
Note, such as United States Patent (USP) US 8304512, US8367798 and US8372945.
In typical polymer solar battery, as donor material semi-conducting polymer with as receptor material
The fullerene derivate of material is mixed, and the mixture is clipped in the anelectrode of a transparent high work function (also becomes sun
Pole, such as ITO or modified ITO) and low workfunction metal negative electrode (also become negative electrode, such as aluminum or change
Property aluminum).The efficiency of polymer solar battery is referred to as energy conversion efficiency (PCE), it with short circuit current (Jsc),
Open-circuit voltage (Voc) and fill factor, curve factor (FF) are directly proportional.
Although in the past huge progress is achieved in 10 years, polymer solar battery is as efficiency is low and is made
With semi-conducting polymer prepare the reason such as poor repeatability still lag behind field of solar energy yield unusually brilliant results it is inorganic
Thin film technique, it is therefore necessary to further develop the solar energy polymer of high-dissolvability, it is desirable to which they are in printing side
Face should have original performance.In addition also need to a kind of repeating of exploitation and prepare high efficiency semiconductor polymer process.
The content of the invention
Invention provide it is a kind of can electronic printable semi-conducting polymer, which has higher in conventional organic solvent
Dissolubility, while being that electronic printable lays the foundation so as to the film for being formed, with pattern preferably, can
To obtain higher charge mobility；There is the benzene of alternately connection in addition plus the semi-conducting polymer because of the present invention
And [1,2-b；4,5-b'] double (4- alkyl -2- thiophene)-(the bis- fluoro- 2,1,3- diazosulfides of 5,6-) of double thiophene and 4,7- it is poly-
Polymer backbone, optimizes LUMO and HOMO energy levels, thus, by manufactured by above-mentioned semiconductive polymer
Organic photovoltaic devices, with higher phototranstormation efficiency.
In order to solve the above problems, the technical solution used in the present invention is such；It is a kind of can electronic printable half
Conductive polymers, its structural formula as shown in SCP-1M-00,
Wherein, R1 is the alkyl that carbon atom is 1-40；
R2 is the alkyl that carbon atom is 1-30；
N is the positive integer arbitrarily more than 10.
Wherein, R1 is preferably but not limited to following group：2- ethylhexyls, 2- butyl hexyls, 2- butyl octyls,
2- hexyl octyl groups, 2- hexyl decyls, 2- hexyl dodecyls, 2- octyl-decyls, 2- octyldodecyls, 2-
Octyl group myristyl, 2- octyl group palmityls, 2- decyl dodecyls, 2- decyl myristyls, 2- decyls 16
Base, 2- dodecyl myristyls, 2- dodecyls cetyl or 2- dodecyl octadecyls.
R2 is preferably but not limited to following group：Propyl group, isopropyl, butyl, isobutyl group, n-hexyl are just pungent
Base, 2- ethylhexyls, decyl, dodecyl, 2- butyl hexyls, 2- butyl octyls, 2- hexyl octyl groups, 2-
Hexyl decyl, 2- hexyl dodecyls, 2- octyl-decyls, 2- octyldodecyls, 2- octyldodecyls,
2- octyl group cetyls, 2- decyls dodecyl or 2- decyl myristyls.
It is further preferred that R1=2- octyldodecyls, R2=ethylhexyls, the preferably semi-conductive polymeric
The structural formula of thing is as shown in SCP-1M-20：
Wherein, n is the positive integer arbitrarily more than 10.
The semi-conducting polymer is [4,7- bis- [4- (2- octyldodecyl -2- thiophene]-(5,6- fluoro -2,1,3- benzos
Thiadiazoles)] and [4,8- bis- [5- (2- ethylhexyls) -2- thiophene)] benzo [1,2-b；4,5-b'] double thiophene] copolymer.
It is further preferred that R1=2- decyl myristyls, R2=2- ethylhexyls, this another preferably partly lead
The structural formula of body polymer is as shown in SCP-1M-24：
Wherein n is the positive integer arbitrarily more than 10.
The semi-conducting polymer is [4,7- bis- [4- (2- decyl myristyls) -2- thienyls]-(bis- fluoro -2,1,3- of 5,6-
Diazosulfide)] and [4,8- bis- [5- (2- ethylhexyls) -2- thienyls] benzo [1,2-b；4,5-b'] double thiophene] be total to
Polymers.
It is above-mentioned can the semi-conducting polymer of electronic printable can be as usual by the relatively simple easy method synthesis in the field
Stille coupling reactions are prepared, and the method is repeatable and can amplify.
Present invention also offers the film formed by the solution of above-mentioned semiconductive polymer.
Present invention also offers application of the above-mentioned semiconductive polymer in organic photovoltaic devices.
Beneficial effect：
1. semiconducting copolymer of the present invention has higher solubility in conventional organic solvent, so as to beat for electronics
Print lays the foundation, and then original performance is had in terms of printing.
2. semi-conducting polymer of the present invention has the benzo [1,2-b of alternately connection；4,5-b'] double thiophene and 4,7- be double
The polymer backbone of (4- alkyl -2- thiophene)-(5,6- bis- fluoro- 2,1,3- diazosulfide), and then optimize LUMO
With HOMO energy levels, can extreme difference, it is seen that light and near infrared light bandwidth and strong absorption band more with solar spectrum
Match somebody with somebody.
3. benzo [1,2-b in the polymer that the present invention is developed；4,5-b'] double (4- alkyl -2- thiophenes of double thiophene and 4,7-
Fen)-(bis- fluoro- 2,1,3- diazosulfides of 5,6-) in the design of alkyl group also make polymer present novel substance
Composition, this alkyl group are provided for the required dissolubility in conventional organic solvent, so as to molten by which
Liquid makes thin film.Pattern with optimization, it is possible to obtain higher charge mobility.
4th, the present invention can present more preferable phototranstormation efficiency for the organic photovoltaic devices of manufacture.
Description of the drawings
Fig. 1 is the curve chart of the I-E characteristic of semi-conducting polymer CP-1M-20.
Specific embodiment
In order to deepen the understanding of the present invention, below in conjunction with embodiment and accompanying drawing, the invention will be further described,
The embodiment is only used for the explanation present invention, does not constitute limiting the scope of the present invention.
Embodiment 1 it is a kind of can electronic printable semi-conducting polymer, its structural formula as shown in SCP-1M-20,
The concrete preparation process of semi-conducting polymer SCP-1M-20 is as follows：
To in the flask of 500ml, add 3.00g (2.84mmmol) IT1055 (to be purchased from Canada 1-Material
Inc companies), 2.57g (2.84mmol) IT0904 (is purchased from 1-Material Inc companies of Canada), in argon
50ml chlorobenzenes are added under gas shielded to form homogeneous phase solution, obtained solution using after bubbling argon 30min,
72.8mg (0.2392mmol) P (o-tol) is added in solution3With the Pd of 55mg (0.0598mmol)2(dba),
Flow back 48h under agitation, then adds 1ml phenyl-bromides in reactant liquor, after continuing stirring 5h, by flask
Room temperature is cooled to, reactant liquor is poured in 1000ml methanol, the polymer precipitation of generation is collected by filtration,
The polymer of collection carries out soxhlet extractions using acetone, ethyl acetate and dichloromethane successively, by dichloromethane
The extraction product of alkane is concentrated, and enriched product is poured into make in acetone polymer and precipitate, and is then collected by filtration
Polymer is precipitated, and is vacuum dried, and such that it is able to obtain the polymer of 3.9g purification, the polymer is brilliant violet
Black solid.Its synthetic line is as follows：
The Jing analysis results of products therefrom are as follows：1HNMR(CDCl3):δ0.85-1.88(br),2.91-3.04(br),
6.95-8.37(br)；(polystyrene is dissolved in CHCl to GPC3As reference material), Mw=40000, PDI=2.2.
The dissolubility of 2 semi-conducting polymer SCP-1M-20 of embodiment
The polymer SCP-1M-20 that embodiment 1 is obtained is fully soluble in conventional organic solvent, and that what is tested is molten
Agent includes dichloromethane, normal hexane, chloroform, tetrahydrofuran, toluene, chlorobenzene, o-dichlorohenzene, dimethyl-penten
Diacid and dimethyl succinate.For example, concentration is the chloroform of the SCP-1M-20 of 5%wt/vol (or following)
Solution can be obtained by the polymer in embodiment 1 is dissolved in chloroform at room temperature easily.Especially,
Polymer SCP-1M-20 in the present invention is soluble in non-halogen solvent, such as normal hexane, tetrahydrofuran, dimethyl
1,3-propanedicarboxylic acid and dimethyl succinate, so as to provide possibility for solution process is carried out to this polymer using green solvent.
SCP-1M-20 solution is in deep blue purple color, and the thin film of SCP-1M-20 by drippage coating or rotating can be coated on
Matrix material can generate one and have metallic luster and for hepatic homogeneous thin film as being obtained on glass after coating,
The thin film can also be formed on other base materials, such as quartz, silicon chip, PET and ITO (indiums-stannum oxidation
Thing coated glass).
3 semi-conducting polymer SCP-1M-20 of embodiment must be applied on OPV
In this embodiment, electron acceptor material PC71BM and cathode interface material it is poly- [(9,9- bis- (3 '-(N, N-
Dimethyl amine) propyl group) -2,7- fluorenes)-alt-2,7- (9,9- dioctyl fluorenes)] (PFN) purchased from 1-Material companies.Poly- (3,4-
Ethylene dioxythiophene)：Poly- (styrene sulfonate) (PEDOT：PSS, Clevios P AI4083) purchase
In H.C.Starck Cleyios GmbH
OPV devices are inverted by ITO/PFN/SCP-1M-20:PC71BM/MoO3/ Al structure compositions, its making
Process list of references：Zhicai He, et al., Nature Photonic, 9,174 (2015).
Photosensitive layer deposit before, be PFN thin layers first, its be by by PFN solution with 2000r.p.m
Rotating speed it is rotating be coated on precleaning ITO substrate (ITO substrate can using oxygen plasma cleaning carry out within 4 minutes
Precleaning) the superiors formed initial thickness for 10nm boundary layer, the interfacial layer thickness is by surface profile
Instrument (Alfa Step-500, Tencor) determines, will infer from absorption-thickness curve and assume that this film thickness exists
Adsorb at 380nm it is linear combines, wherein, PFN solution is by by its solid (anhydrous, content
99.8%) dissolving is obtained in methyl alcohol, needs to add a small amount of acetic acid (2-20 μ l/ml, final acetic acid during dissolving
Addition depending on PFN molecular weight)；During spin coating, PFN solution concentrations are generally 2mg/ml.
And then PFN boundary layers, which is SCP-1M-20:PC71BM activity mixed layers, theoretic throat exist
300nm or so, this active layer is by by dichloromethane and 1,8- diiodo-octane mixed solution (volume ratio 97:3
) under the rotating speed of 1000r.p.m spin coating complete within 2 minutes, corresponding photoactive layer needs vacuum before electrode deposition
Under be dried 3h.Wherein, dichloromethane and 1,8- diiodo-octane mixed solution are by obtained polymer in embodiment 1
SCP-1M-20 and PC71BM is 1 in mass ratio:1.5 are blended in solvent (by the dichloromethane and 3v% of 97v%
1,8- diiodo-octanes composition) in formed, polymer SCP-1M-20 and PC in the mixed solution71BM's
Concentration is respectively 10mg/ml and 15mg/ml.
The MoO of 10nm3The Al layers of layer and 100nm pass in succession through shadow mask evaporation formation of deposits surface anode,
So as to the active area for determining the device is about 2 × 8mm2。
The device of preparation is sealed in nitrogen glove box by UV epoxy resin and glass cover.Electric current density-electricity
The 2400 source measuring unit measurements of Keithley of pressure (J-V) curve.Photoelectric current is 100 using solar simulator
mW/cm2Intensity, tests when illumination is AM 1.5G；Light intensity is by National Renewable Energy laboratory
(NREL) the single silicon detector calibrated is determining.
As shown in figure 1, being calculated Voc (V)=0.70, Jsc (mA/cm by the curve2)=14.40, FF
(%)=0.33, Whole PC E (%)=3.3 for accordingly obtaining.
It is to be noted that the thick film of 300nm can draw so good OPV performances, also just indicate that it has and answer
Potential in reel-to-reel printing, and as the optimization of OPV apparatus structures should have higher light conversion effect
Rate.
Presently preferred embodiments of the present invention is the foregoing is only, it is not to limit the present invention, all in the present invention
Spirit and principle within, any modification, equivalent substitution and improvements made etc., should be included in the present invention
Within protection domain.
Claims (7)
1. it is a kind of can electronic printable semi-conducting polymer, it is characterised in that its structural formula such as SCP-1M-00
It is shown,
Wherein, R1 is the alkyl that carbon atom is 1-40；
R2 is the alkyl that carbon atom is 1-30；
N is the positive integer arbitrarily more than 10.
2. semi-conducting polymer according to claim 1, it is characterised in that R1 is selected from 2- ethyl hexyls
Base, 2- butyl hexyls, 2- butyl octyls, 2- hexyl octyl groups, 2- hexyl decyls, 2- hexyl dodecyls, 2-
Octyl-decyl, 2- octyldodecyls, 2- octyl group myristyls, 2- octyl group palmityls, 2- decyl dodecyls,
2- decyl myristyls, 2- decyl palmityls, 2- dodecyl myristyls, 2- dodecyls cetyl or
2- dodecyl octadecyls.
3. semi-conducting polymer according to claim 1 and 2, it is characterised in that R2 is selected from propyl group,
Isopropyl, butyl, isobutyl group, n-hexyl, n-octyl, 2- ethylhexyls, decyl, dodecyl, 2- fourths
Base hexyl, 2- butyl octyls, 2- hexyl octyl groups, 2- hexyl decyls, 2- hexyl dodecyls, 2- octyl-decyls,
2- octyldodecyls, 2- octyldodecyls, 2- octyl group cetyls, 2- decyls dodecyl or 2- decyls
Myristyl.
4. semi-conducting polymer according to claim 3, it is characterised in that R1=2- octyldodecyls
Base, R2=2- ethylhexyls.
5. semi-conducting polymer according to claim 3, it is characterised in that R1=2- decyl myristyls,
R2=2- ethylhexyls.
6. the film formed by the semiconductive polymer solution described in any claim of claim 1-5.
7. the semiconductive polymer described in any claim of claim 1-5 is in organic photovoltaic devices
Using.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510651847.0A CN106565939A (en) | 2015-10-10 | 2015-10-10 | Semi-conducting polymers capable of electronic printing and applications thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510651847.0A CN106565939A (en) | 2015-10-10 | 2015-10-10 | Semi-conducting polymers capable of electronic printing and applications thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106565939A true CN106565939A (en) | 2017-04-19 |
Family
ID=58507791
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510651847.0A Pending CN106565939A (en) | 2015-10-10 | 2015-10-10 | Semi-conducting polymers capable of electronic printing and applications thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106565939A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200043092A (en) * | 2018-10-17 | 2020-04-27 | 주식회사 엘지화학 | Copolymer and electronic device comprising the same |
| CN111518115A (en) * | 2020-04-15 | 2020-08-11 | 南京欧纳壹有机光电有限公司 | Thioether-substituted 2-thiazolin-4-one-terminated organic semiconductor compound |
| KR20200102166A (en) * | 2019-02-21 | 2020-08-31 | 한국과학기술연구원 | conjucated polymer for Low temperature process and organic solar cell using the same |
| KR102663400B1 (en) | 2019-01-07 | 2024-05-03 | 주식회사 엘지화학 | Copolymer and electronic device comprising the same |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103804650A (en) * | 2012-11-12 | 2014-05-21 | 海洋王照明科技股份有限公司 | Difluorobenzothiadiazole-based copolymer and preparation method and application thereof |
| CN104119512A (en) * | 2013-04-25 | 2014-10-29 | 海洋王照明科技股份有限公司 | Polymer containing difluoro diazosulfide unit and preparation method thereof and solar cell device |
| CN104211912A (en) * | 2013-05-29 | 2014-12-17 | 海洋王照明科技股份有限公司 | Conjugated polymer, preparation method and applications thereof |
| CN104961884A (en) * | 2015-05-28 | 2015-10-07 | 合肥工业大学 | A-[pi]-A type conjugated semiconductor polymer based on pyridazino pyrroledione, and preparation method thereof |
-
2015
- 2015-10-10 CN CN201510651847.0A patent/CN106565939A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103804650A (en) * | 2012-11-12 | 2014-05-21 | 海洋王照明科技股份有限公司 | Difluorobenzothiadiazole-based copolymer and preparation method and application thereof |
| CN104119512A (en) * | 2013-04-25 | 2014-10-29 | 海洋王照明科技股份有限公司 | Polymer containing difluoro diazosulfide unit and preparation method thereof and solar cell device |
| CN104211912A (en) * | 2013-05-29 | 2014-12-17 | 海洋王照明科技股份有限公司 | Conjugated polymer, preparation method and applications thereof |
| CN104961884A (en) * | 2015-05-28 | 2015-10-07 | 合肥工业大学 | A-[pi]-A type conjugated semiconductor polymer based on pyridazino pyrroledione, and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| NING WANG,ET AL.: "Fluorinated Benzothiadiazole-Based Conjugated Polymers for High-Performance Polymer Solar Cells without Any Processing Additives or Post-treatments", 《J. AM. CHEM. SOC.》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200043092A (en) * | 2018-10-17 | 2020-04-27 | 주식회사 엘지화학 | Copolymer and electronic device comprising the same |
| KR102594843B1 (en) | 2018-10-17 | 2023-10-26 | 주식회사 엘지화학 | Copolymer and electronic device comprising the same |
| KR102663400B1 (en) | 2019-01-07 | 2024-05-03 | 주식회사 엘지화학 | Copolymer and electronic device comprising the same |
| KR20200102166A (en) * | 2019-02-21 | 2020-08-31 | 한국과학기술연구원 | conjucated polymer for Low temperature process and organic solar cell using the same |
| KR102228274B1 (en) * | 2019-02-21 | 2021-03-17 | 한국과학기술연구원 | conjucated polymer for Low temperature process and organic solar cell using the same |
| CN111518115A (en) * | 2020-04-15 | 2020-08-11 | 南京欧纳壹有机光电有限公司 | Thioether-substituted 2-thiazolin-4-one-terminated organic semiconductor compound |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101597373B1 (en) | Organic photovoltaic devices comprising fullerenes and derivatives thereof and improved methodes of making fullerene derivatives | |
| US9166171B2 (en) | Methanofullerene derivatives and photoelectric conversion devices using same | |
| Zhang et al. | Copolymers from benzodithiophene and benzotriazole: synthesis and photovoltaic applications | |
| JP5573066B2 (en) | Organic photoelectric conversion element, solar cell and optical sensor array using the same | |
| Hou et al. | Synthesis and photovoltaic properties of the copolymers of 2-methoxy-5-(2′-ethylhexyloxy)-1, 4-phenylene vinylene and 2, 5-thienylene-vinylene | |
| CN107108860A (en) | Conjugated polymer and its application based on terthienyl | |
| JP2013179181A (en) | Organic photoelectric conversion element | |
| US20170002125A1 (en) | Asymmetric Regio-regular Conjugated Polymers for Electronic Applications | |
| KR20120130706A (en) | Electron donating polymer and solar cell including the same | |
| CN106565939A (en) | Semi-conducting polymers capable of electronic printing and applications thereof | |
| Kim et al. | Synthesis and characterization of indeno [1, 2-b] fluorene-based low bandgap copolymers for photovoltaic cells | |
| WO2010110590A2 (en) | Solar cell, and method for producing same | |
| Feng et al. | Triphenylamine modified bis-diketopyrrolopyrrole molecular donor materials with extended conjugation for bulk heterojunction solar cells | |
| CN107674183B (en) | Containing naphthalene [1,2-c；5,6-c] two [1,2,5] thiadiazoles conjugated polymer and preparation method and application | |
| EP2343751A1 (en) | Organic photoelectric conversion element | |
| WO2009142330A1 (en) | Organic photoelectric conversion element and manufacturing method therefor | |
| WO2009119871A1 (en) | Organic photoelectric conversion element | |
| Ullah et al. | Donor-acceptor (DA) terpolymers based on alkyl-DPP and t-BocDPP moieties for polymer solar cells | |
| CN103923106B (en) | Conjugated polymer that a kind of mental retardation gap length absorbs and preparation method thereof | |
| PanFeng et al. | Synthesis, characterizations and photovoltaic applications of a thickness-insensitive benzodifuran based copolymer | |
| JP2011238762A (en) | Photoelectric conversion element | |
| US20140060650A1 (en) | Polyhedral oligomeric silsesquioxane organic/polymeric dyads and its application for organic photovoltaic cells | |
| CN105131258B (en) | A kind of regioregular polymerization thing and its application for substituting 2,1,3 diazosulfide groups containing asymmetry list fluorine | |
| WO2016015533A1 (en) | Organic small molecular semiconductor material, and synthetic method and use thereof | |
| CN104448247B (en) | A kind of containing benzo double thiophene and the semi-conducting polymer of thiophene, prepare and apply |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20170419 |