CN109021214A - The n-type conjugated polymer and its application in organic electro-optic device that base side chain containing oligomeric ethylene glycol modifies benzene-naphthalene diimide unit - Google Patents
The n-type conjugated polymer and its application in organic electro-optic device that base side chain containing oligomeric ethylene glycol modifies benzene-naphthalene diimide unit Download PDFInfo
- Publication number
- CN109021214A CN109021214A CN201810548275.7A CN201810548275A CN109021214A CN 109021214 A CN109021214 A CN 109021214A CN 201810548275 A CN201810548275 A CN 201810548275A CN 109021214 A CN109021214 A CN 109021214A
- Authority
- CN
- China
- Prior art keywords
- benzene
- ethylene glycol
- side chain
- base side
- chain containing
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/10—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising heterojunctions between organic semiconductors and inorganic semiconductors
- H10K30/15—Sensitised wide-bandgap semiconductor devices, e.g. dye-sensitised TiO2
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/12—Copolymers
- C08G2261/124—Copolymers alternating
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/142—Side-chains containing oxygen
- C08G2261/1424—Side-chains containing oxygen containing ether groups, including alkoxy
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/18—Definition of the polymer structure conjugated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- 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
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- 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
- C08G2261/3241—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
The present invention relates to the n-type conjugated polymer of the modification benzene-naphthalene diimide unit of base side chain containing oligomeric ethylene glycol and its applications in organic electro-optic device.Its structural formula of the n-type conjugated polymer of the described oligomeric ethylene glycol base side chain modification benzene-naphthalene diimide unit is as follows, and wherein Ar1 and Ar2 is aromatic group；The R1 and R2 is H, C1~50Alkyl straight-chain or branched chain；The integer that the m is 1 ~ 10；0 < the x < 1,0 < y < 1, x+y=1；The natural number that the n is 1 ~ 10000.The polymer has suitable electronic transmission performance, is applied to have suitable blend film pattern in organic electro-optic device, the device prepared has high performance and/or good long-time stability.
Description
Technical field
The present invention relates to organic photoelectrical material fields, and in particular to base side chain containing oligomeric ethylene glycol modifies benzene-naphthalene diimide list
The n-type conjugated polymer of member and its application in organic electro-optic device.
Background technique
Since 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
Protect ball ecological environment needs, the more and more scientists in the whole world by research concentrate on develop and utilize wind energy, geothermal energy,
The inexhaustible renewable and clean energy resource such as solar energy.
Based on organic/polymer solar cells of organic/polymer material as a kind of novel thin film photovoltaic cell technology,
Have many advantages, such as it is all solid state, can be achieved it is translucent, can be made into flexible device.In addition, organic/polymer solar cells can be used it is low
The roll-to-roll processing method processing preparation broad area device of cost.The use of organic/polymer solar cells is hardly by environment
It is limited with place, has very strong complementarity with inorganic semiconductor solar cell, there is huge business development value and market
Competitiveness.The photovoltaic performance adjustable extent of organic/polymer material is wide, using chemical means to material, electron energy level, load
The performances such as stream transport factor and solution processing are effectively regulated and controled.Therefore the research of organic/polymer solar cells causes
Extensive concern has become worldwide competition as the scientific research of core using organic/polymer solar cells and swashs
Strong material science research frontier.
Study extensive organic/polymer solar cells at present is to be based on Heeger, A J et al. (Science1995,
270,1789.) device of the bulk-heterojunction model proposed in nineteen ninety-five, core is the light of organic/polymer solar cells
The heterojunction structure that active layer is made of two kinds of materials of donor and receptor.The structure of this kind of hetero-junctions was due to development in more than 20 years
10% -13% (Nat.Commun.2013,4,1446 is obtained in efficiency；J.Am.Chem.Soc.,2017,139,
7148.) breakthrough.But pattern is blended to its battery device performance and stability in its active layer of the structure of this bulk-heterojunction
Influence extremely serious, so that it is in batches of materials, large area preparation, industrial applications etc., many-sided there is very high technologies
Threshold.
Summary of the invention
In order to overcome above-mentioned bulk-heterojunction in the prior art it is organic/polymer solar cells device architecture in photoactive layer
Blend film pattern be difficult to control and the disadvantage of stability difference, the purpose of the present invention is to provide a kind of with excellent blending work
Property layer pattern n-type conjugated polymer acceptor material and polymeric donor mixing after prepare ideal pattern, steady in a long-term
Polymer/polymer solar cell device.Its core technology is that base side chain containing oligomeric ethylene glycol modifies benzene-naphthalene diimide unit
N-type conjugated polymer, unlike existing polymeric acceptor material, such base side chain containing oligomeric ethylene glycol modifies two acyl of naphthalene
The n-type conjugated polymer of imines unit can be formed under the action of the oligomeric ethylene glycol base side chain of part with polymer donor material
The polymer/polymer solar cell device of efficient stable can be finally prepared, therefore in the photoactive layer pattern of ideal stability
It is poly- that the n-type conjugated polymer of the base side chain containing oligomeric ethylene glycol modification benzene-naphthalene diimide unit is expected to substitute existing commercialization
Close object receptor.
The purpose of the present invention is realized by following proposal:
Base side chain containing oligomeric ethylene glycol modifies the n-type conjugated polymer of benzene-naphthalene diimide unit, has the following structure:
Wherein, the integer that m is 1~10；0 < the x < 1,0 < y < 1, x+y=1；The natural number that n is 1~10000；It is described
Ar1 and Ar2 is the conjugate unit for forming conjugated polymer；The conjugate unit is thiophene, furans, benzene, fluorenes, carbazole, silicon fluorene, benzene
1,4-Dithiapentalene, two selenophen of benzo, two furans of benzo, phenthazine, phenoxazine, bithiophene, bithiophene, thiophene pentalene, thiophene
Pheno and pyrroles, thieno thiophene cough up, indoles fluorenes, indole carbazole, pyrroles, naphthalimide, one of acid imide and its derivative
More than；The R1 and R2 is H, C1~50Alkyl straight-chain or C1~50Branched alkyl chain.
Further, one or more coupled structures that wherein conjugate unit Ar1 and Ar2 has the following structure:
A kind of preparation method of the n-type conjugated polymer of the modification of base side chain containing oligomeric ethylene glycol benzene-naphthalene diimide unit, tool
Body is following steps: adding base side chain containing oligomeric ethylene glycol to modify naphthalene by x times of molar ratio Ar1, y times of molar ratio Ar2 all monomers
Imide monomer is mixed, and wherein Ar2 and the modification benzene-naphthalene diimide monomer of base side chain containing oligomeric ethylene glycol are equimolar ratio,
0 < x < 1,0 < y < 1, x+y=1 are polymerize under palladium catalyst catalysis, obtain corresponding polymer material by purifying.
Base side chain containing oligomeric ethylene glycol modifies the n-type conjugated polymer of benzene-naphthalene diimide unit in organic electro-optic device
It is applied as electron acceptor.
Compared with the prior art, the present invention has the following advantages:
(1) present invention devises a kind of n-type conjugated polymer acceptor material of novel side chain modification.
(2) present invention, which realizes, is bordering on ideal polymer/polymer solar cell photoactive layer pattern, so that poly-
It closes object/polymer solar cells device fill factor and is higher than 75%.
(3) present invention realizes the polymer/polymer solar cell device with excellent stability.
(4) invention demonstrates a method the n-type conjugated polymers of the modification benzene-naphthalene diimide unit of base side chain containing oligomeric ethylene glycol to exist
Realize efficient stable it is organic/polymer photovoltaics in excellent potentiality.
Detailed description of the invention
Fig. 1 is the n-type conjugated polymer of the modification benzene-naphthalene diimide unit of base side chain containing oligomeric ethylene glycol of specific implementation
Synthetic route chart.
Fig. 2 is polymer/polymer (PBDT-TAZ/NOE10) solar cell active layer polymer structural formula and battery
Device architecture schematic diagram.
Fig. 3 is the current density-voltage curve of polymer/polymer (PBDT-TAZ/NOE10) solar cell device.
Fig. 4 is organic/polymer solar cells device stability comparison of several different activities layer structures.
Specific embodiment
Below by specific embodiment, the present invention is further illustrated, and its object is to help to better understand this hair
Bright content specifically includes the synthesis and device preparation method of polymer, but these specific embodiments do not limit in any way
Protection scope of the present invention processed.
The routine techniques of the polymer chemistry in art technology can be used in practice of the invention.In the examples below,
The accuracy for endeavouring to ensure digital (including amount, temperature, reaction time etc.) used, it is contemplated that some experimental errors and deviation.
Temperature used to be in the examples below DEG C to indicate, and pressure is for atmospheric pressure or close to atmospheric pressure.Solvent for use be analyze it is pure or
Chromatographically pure purchase, and all reactions carry out in nitrogen atmosphere.Unless otherwise noted, otherwise all reagents are all that business obtains
?.
Specific implementation method
Embodiment 1
Base side chain containing oligomeric ethylene glycol modifies the preparation of benzene-naphthalene diimide monomer (structure 3).
Chemical reaction process is as follows, and specific reaction step and reaction condition are as follows:
(1) raw material or intermediate reaction object, tetraethylene glycol monomethyl ether, diisopropyl azodiformate, phthalimide, three
Phenylphosphine, hydrazine hydrate, 2,6- dibromine naphthalene -1,4,5,8- tetracarboxylic acid dianhydride are that commercially produced product directly uses.
(2) preparation of intermediate 1
Under nitrogen protection, by tetraethylene glycol monomethyl ether (6g), phthalimide (4.5g) and triphenylphosphine (8.5g)
It is dissolved in 150 milliliters of methylene chloride, 6.5g diisopropyl azodiformate is slowly added dropwise into reaction solution at 0 DEG C,
Stirring at normal temperature 12 hours.Solvent is removed after reaction, and silica gel column purification obtains 7g intermediate 1, yield 75%.
(3) preparation of intermediate 2
Under nitrogen protection, monomer 1 (6g) and hydrazine hydrate (2g) are dissolved in 150 milliliters of ethyl alcohol, return stirring 6 is small
When.Solvent is removed after reaction, and silica gel column purification obtains 2g intermediate 2, yield 70%.
(4) preparation of monomer 3
Under nitrogen protection, by monomer 2 (1.5g) and 2,6- dibromine naphthalene-Isosorbide-5-Nitrae, 5,8- tetracarboxylic acid dianhydrides (0.5g) are dissolved in
In 50 milliliters of acetic acid, return stirring 6 hours.Solvent is removed after reaction, and silica gel column purification obtains 0.3g monomer 3, yield
35%.
Embodiment 2
Base side chain containing oligomeric ethylene glycol modifies the preparation of the n-type conjugated polymer (abbreviation NOE10) of benzene-naphthalene diimide unit
Chemical reaction process is as follows, and specific reaction step and reaction condition are as follows:
(1) raw material or intermediate reaction object, monomer 4, monomer 5, tetra-triphenylphosphine palladium are that commercially produced product directly uses.
(2) under nitrogen protection, by monomer 3 (0.02 mM), monomer 4 (0.18 mM), (0.2 mmoles of monomer 5
You) and 3 milligrams of tetra-triphenylphosphine palladiums be dissolved in 2 milliliters of chlorobenzene, 120 DEG C stirring 12 hours.After reaction in methyl alcohol
It is settled out polymer, then extracts last chloroform through methanol, acetone, n-hexane and goes out final polymer, again after methanol extraction
It dries and obtains final polymer NOE10,180 milligrams, yield 90%.
Embodiment 3
Illustrate by taking 2 resulting polymers material of embodiment as an example such polymer material as polymeric acceptor polymer/
Application in polymer solar cells device.
Following instance will modify base side chain containing oligomeric ethylene glycol proposed by the invention the n-type of benzene-naphthalene diimide unit
Conjugated polymer and its applied technical procedure in organic electro-optic device are illustrated, but the present invention is not limited to the cited case.
The specific preparation process of device is as follows:
One layer 40 nanometers of spin coating of the PEDOT:PSS hole transmission layer on ITO, the then polymerization of 100 ran of spin coating
Photoactive layer is blended with NOE10 by object donor PBDT-TAZ, then the Quaternary ammonium bromide of the amido polyfluorene of 5 ran of spin coating
(PFN-Br) it is used as cathode interface layer, then 100 nanometer Ag layers are deposited, that is, completes the preparation of device.J-V curve test is carried out, is obtained
Relevant parameter to device is as shown in Table 1.As can be seen from Table I, the PBDT-TAZ/ in NOE10 as polymeric acceptor
The polymer/polymer solar cell device of NOE10 can obtain 0.75 fill factor, this is current polymer/polymer
One of the best result of solar cell device, while 8% device efficiency can also be achieved over.Therefore, it can be seen that this kind of contain
The n-type conjugated polymer that oligomeric ethylene glycol base side chain modifies benzene-naphthalene diimide unit is good polymeric acceptor material, is one
The polymer/polymer solar cell material that class is had excellent performance.
The performance parameter of table one one-component device ITO/PEDOT:PSS/X-0 or X-1/Ca/Al
Embodiment 4
Illustrate such polymer/polymer too for obtaining polymer/polymer solar cell device prepared by embodiment 3
The stability of positive battery device.
The specific preparation process of device is as follows:
One layer 40 nanometers of spin coating of the PEDOT:PSS hole transmission layer on ITO, the then polymerization of 100 ran of spin coating
Photoactive layer is blended with NOE10 by object donor PBDT-TAZ, then the Quaternary ammonium bromide of the amido polyfluorene of 5 ran of spin coating
(PFN-Br) it is used as cathode interface layer, then 100 nanometer Ag layers are deposited, that is, completes the preparation of device.While in order to carry out stability
Comparative experiments, while be prepared for photoactive layer be PBDT-TAZ be donor material and several commercialization acceptor materials (N2200,
PCBM, ITIC) device that is blended, while also providing a comparison of two class Efficient devices systems (PBDB-T:ITIC and PCE11:PCBM).Its
Corresponding shelf stability and hot ageing stability result are as shown in Figure 4.From Fig. 4 it will be seen that for same donor
Polymer, NOE10 show optimal shelf stability i.e. storage be still able to maintain more than 400 hours the 95% of starting efficiency with
On.And the corresponding device of other several class commercialization acceptor material preparations, obviously efficiency was shown at 100-200 hours
Decline.In addition the thermal ageing test carried out under the conditions of 65 DEG C also indicates that NOE10 has as the battery device of acceptor polymer
Good thermal stability is also still able to maintain the 95% of initial device efficiency 65 DEG C of heat ageings 300 are small at present.Totally show this
The n-type conjugated polymer that class base side chain containing oligomeric ethylene glycol modifies benzene-naphthalene diimide unit is good polymeric acceptor material,
It is that the battery device that a kind of polymer/polymer solar cell material haveing excellent performance is prepared is stablized with good device
Property, it is a kind of very with the polymeric acceptor material of Commercial Prospect.
The above embodiment of the present invention be only to clearly illustrate example of the present invention, and not be to the present invention
Embodiment restriction.For those of ordinary skill in the art, it can also make on the basis of the above description
Other various forms of variations or variation.There is no necessity and possibility to exhaust all the enbodiments.It is all of the invention
Made any modifications, equivalent replacements, and improvements etc., should be included in the protection of the claims in the present invention within spirit and principle
Within the scope of.
Claims (4)
1. the n-type conjugated polymer of the modification benzene-naphthalene diimide unit of base side chain containing oligomeric ethylene glycol, which is characterized in that have such as
Flowering structure:
Wherein, the integer that m is 1~10；0 < the x < 1,0 < y < 1, x+y=1；The natural number that n is 1~10000；The Ar1 and
Ar2 is the conjugate unit for forming conjugated polymer；The conjugate unit is thiophene, furans, benzene, fluorenes, carbazole, silicon fluorene, benzo two
Thiophene, two selenophen of benzo, two furans of benzo, phenthazine, phenoxazine, bithiophene, bithiophene, thiophene pentalene, thieno
Pyrroles, thieno thiophene cough up, indoles fluorenes, indole carbazole, pyrroles, naphthalimide, one or more of acid imide and its derivative；
The R1 and R2 is H, C1~50Alkyl straight-chain or C1~50Branched alkyl chain.
2. the n-type conjugated polymer of the modification of base side chain containing oligomeric ethylene glycol benzene-naphthalene diimide unit according to claim 1,
It is characterized in that, one or more coupled structures that wherein conjugate unit Ar1 and Ar2 has the following structure:
3. the n-type conjugated polymers of the modification benzene-naphthalene diimide unit of base side chain containing oligomeric ethylene glycol described in claim any one of 1-2
The preparation method of object, which is characterized in that be specially following steps: all monomers are pressed into x times of molar ratio Ar1, y times of molar ratio Ar2
The modification benzene-naphthalene diimide monomer of base side chain containing oligomeric ethylene glycol is added to be mixed, wherein Ar2 is repaired with base side chain containing oligomeric ethylene glycol
Decorations benzene-naphthalene diimide monomer is equimolar ratio, and 0 < x < 1,0 < y < 1, x+y=1 are polymerize, by pure under palladium catalyst catalysis
Change obtains corresponding polymer material.
4. the n-type conjugation of the described in any item modification of base side chain containing the oligomeric ethylene glycol benzene-naphthalene diimide units of claim 1-2 is poly-
Object is closed to be applied in organic electro-optic device as electron acceptor.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810548275.7A CN109021214A (en) | 2018-05-31 | 2018-05-31 | The n-type conjugated polymer and its application in organic electro-optic device that base side chain containing oligomeric ethylene glycol modifies benzene-naphthalene diimide unit |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810548275.7A CN109021214A (en) | 2018-05-31 | 2018-05-31 | The n-type conjugated polymer and its application in organic electro-optic device that base side chain containing oligomeric ethylene glycol modifies benzene-naphthalene diimide unit |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109021214A true CN109021214A (en) | 2018-12-18 |
Family
ID=64611988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810548275.7A Pending CN109021214A (en) | 2018-05-31 | 2018-05-31 | The n-type conjugated polymer and its application in organic electro-optic device that base side chain containing oligomeric ethylene glycol modifies benzene-naphthalene diimide unit |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109021214A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110105548A (en) * | 2019-04-18 | 2019-08-09 | 南京工业大学 | A kind of ternary atactic polymer acceptor material and the preparation method and application thereof adulterating two-dimentional benzene thiophene group |
| CN110204695A (en) * | 2019-06-20 | 2019-09-06 | 吉林大学 | A kind of narrowband system receptor type conjugated polymer containing oligoethylene glycol side-chain structure and preparation method thereof, application |
| CN110229314A (en) * | 2019-06-12 | 2019-09-13 | 南京邮电大学 | A kind of amphipathic conjugated polymer and the preparation method and application thereof |
| CN110272531A (en) * | 2019-06-12 | 2019-09-24 | 南京邮电大学 | A kind of amphipathic naphthoyl Asia diamines conjugated polymer and the preparation method and application thereof |
| KR20200130618A (en) * | 2019-05-10 | 2020-11-19 | 한국과학기술원 | New naphthalene diimide (ndi)-based conjugated polymers for eco-friendly organic electronic device, and eco-friendly organic electronic device |
| CN113690373A (en) * | 2021-07-07 | 2021-11-23 | 华南理工大学 | Based on HfS2Organic solar cell as hole transport layer and method for manufacturing the same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107674180A (en) * | 2017-09-16 | 2018-02-09 | 华南理工大学 | N-type conjugated polymer based on the connected furans of conjugated pi bridge and its application in organic electro-optic device |
-
2018
- 2018-05-31 CN CN201810548275.7A patent/CN109021214A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107674180A (en) * | 2017-09-16 | 2018-02-09 | 华南理工大学 | N-type conjugated polymer based on the connected furans of conjugated pi bridge and its application in organic electro-optic device |
Non-Patent Citations (2)
| Title |
|---|
| GIOVANNITTI, ALEXANDER ET AL.: "The Role of the Side Chain on the Performance of N-type Conjugated Polymers in Aqueous Electrolytes", 《CHEMISTRY OF MATERIALS》 * |
| LIU, JIAN ET AL.: "Enhancing Molecular n-Type Doping of Donor-Acceptor Copolymers by Tailoring Side Chains", 《ADVANCED MATERIALS》 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110105548A (en) * | 2019-04-18 | 2019-08-09 | 南京工业大学 | A kind of ternary atactic polymer acceptor material and the preparation method and application thereof adulterating two-dimentional benzene thiophene group |
| KR20200130618A (en) * | 2019-05-10 | 2020-11-19 | 한국과학기술원 | New naphthalene diimide (ndi)-based conjugated polymers for eco-friendly organic electronic device, and eco-friendly organic electronic device |
| KR102197796B1 (en) | 2019-05-10 | 2021-01-04 | 한국과학기술원 | New naphthalene diimide (ndi)-based conjugated polymers for eco-friendly organic electronic device, and eco-friendly organic electronic device |
| CN110229314A (en) * | 2019-06-12 | 2019-09-13 | 南京邮电大学 | A kind of amphipathic conjugated polymer and the preparation method and application thereof |
| CN110272531A (en) * | 2019-06-12 | 2019-09-24 | 南京邮电大学 | A kind of amphipathic naphthoyl Asia diamines conjugated polymer and the preparation method and application thereof |
| CN110204695A (en) * | 2019-06-20 | 2019-09-06 | 吉林大学 | A kind of narrowband system receptor type conjugated polymer containing oligoethylene glycol side-chain structure and preparation method thereof, application |
| CN113690373A (en) * | 2021-07-07 | 2021-11-23 | 华南理工大学 | Based on HfS2Organic solar cell as hole transport layer and method for manufacturing the same |
| CN113690373B (en) * | 2021-07-07 | 2023-02-14 | 华南理工大学 | Based on HfS 2 Organic solar cell as hole transport layer and method for manufacturing the same |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109021214A (en) | The n-type conjugated polymer and its application in organic electro-optic device that base side chain containing oligomeric ethylene glycol modifies benzene-naphthalene diimide unit | |
| Sun et al. | Non-fullerene-acceptor-based bulk-heterojunction organic solar cells with efficiency over 7% | |
| Zhou et al. | Hierarchical morphology stability under multiple stresses in organic solar cells | |
| Wang et al. | Extending π-conjugation system with benzene: an effective method to improve the properties of benzodithiophene-based polymer for highly efficient organic solar cells | |
| Kim et al. | Effects of solubilizing group modification in fullerene bis-adducts on normal and inverted type polymer solar cells | |
| Burkhart et al. | “Semi-Random” multichromophoric rr-P3HT analogues for solar photon harvesting | |
| He et al. | Industrial viability of single-component organic solar cells | |
| CN103467711B (en) | Connect the semi-conducting polymer of two thiophene oxindole bases and preparation thereof, purposes | |
| Wang et al. | Spirobifluorene-based conjugated polymers for polymer solar cells with high open-circuit voltage | |
| CN106986982A (en) | The molten conjugated polymer of water alcohol of three keys connection and its application in organic electro-optic device | |
| Hu et al. | Influence of substituent groups on chemical reactivity kinetics of nonfullerene acceptors | |
| EP2530084B1 (en) | Copolymer containing fluorenylporphyrin-anthracene, preparation method and use thereof | |
| CN104140521A (en) | Broad-absorption-spectrum ternary conjugated polymer donor material as well as preparation method and application of wide-absorption-spectrum ternary conjugated polymer donor material | |
| Zhao et al. | Highly efficient all-polymer solar cells from a dithieno [3, 2-f: 2′, 3′-h] quinoxaline-based wide band gap donor | |
| CN105367561A (en) | Preparation and use of indole derivative and conjugated polymer thereof | |
| CN105237745A (en) | Quaternary phosphonium salt group-containing conjugated polyelectrolyte and its use in organic photoelectric device | |
| Wang et al. | Ester-substituted pentathiophene copolymer-based sky-blue semitransparent solar cells for building windows | |
| CN109161003A (en) | The n-type conjugated polymer of the benzene-naphthalene diimide of bridging containing thiazole and its preparation and the application in Organic Thin Film Transistors and photovoltaic device | |
| CN112646129B (en) | N-type water/alcohol-soluble conjugated polyelectrolyte containing benzobisthiadiazole and preparation and application thereof | |
| CN107674183B (en) | Containing naphthalene [1,2-c；5,6-c] two [1,2,5] thiadiazoles conjugated polymer and preparation method and application | |
| P Singh et al. | Progress towards efficiency of polymer solar cells | |
| CN102702234B (en) | Dibromo-monomer containing difuranzothiazole, conjugated polymer and use thereof | |
| CN103664950A (en) | Novel trimerization carbazole based narrow band gap conjugated micromolecule material and preparation method thereof | |
| CN103214658B (en) | Narrow-band gap organic solar cell material and preparation method of solar cell material | |
| CN105218791A (en) | Containing 2-(4-thiophene-2-phenyl) polymkeric substance of thiophene and its preparation method and application |
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: 20181218 |