CN108822076A - It is the n-type organic small molecular semiconductor and the preparation method and application thereof of core based on indeno thiophene - Google Patents
It is the n-type organic small molecular semiconductor and the preparation method and application thereof of core based on indeno thiophene Download PDFInfo
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- CN108822076A CN108822076A CN201810619710.0A CN201810619710A CN108822076A CN 108822076 A CN108822076 A CN 108822076A CN 201810619710 A CN201810619710 A CN 201810619710A CN 108822076 A CN108822076 A CN 108822076A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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- H—ELECTRICITY
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
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- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
It is the n-type organic small molecular semiconductor and the preparation method and application thereof of core that the invention discloses a kind of based on indeno thiophene, it is specially core based on indeno thiophene, thiophene is bridging, 1,3- indandione or malononitrile or 5, bis- fluoro- 3- (dicyano methylene) indigo ketone of 6- is the application of n-type Organic micromolecular semiconductor material of end group and preparation method thereof and such molecule as acceptor material in organic non-fullerene solar battery.It is disclosed by the invention to have many advantages, such as that solution processable, absorption spectrum are wide, absorptivity is high, excellent heat stability, energy level are appropriate using indeno thiophene as the n-type organic small molecular semiconductor of core, it is the non-fullerene acceptor material of ideal organic solar batteries.
Description
Technical field
The invention belongs to technical fields, and in particular to a kind of partly to be led based on the n-type small organic molecule that indeno thiophene is core
Body and the preparation method and application thereof.
Background technique
Solar energy is inexhaustible cleaning, green energy resource, recently as countries in the world to energy problem
Attention, solar battery become the field research hotspot.Compared with traditional inorganic semiconductor solar battery, organic sun
Can battery have that at low cost, materials are few, light-weight, manufacture craft is simple, can be prepared into outstanding advantages of flexible device, have extensively
Wealthy development and application prospect.
Typical organic solar batteries use bulk heteroj unction structure, and active layer is by the p-type as donor material half
Conductive polymers and as acceptor material n-type semiconductor form[1-3].Fullerene and its derivative species acceptor material it is organic too
Positive energy field of batteries is chronically at leading position[4-6], however unstable under there are the costs of raw material higher, illumination of this kind of material,
Under high temperature easily crystallization, visible region absorbs weak and is difficult to widen, lowest unoccupied molecular orbital (LUMO) energy level is lower leads to electricity
The disadvantages such as pond open-circuit voltage is low[7], these disadvantages limit its further develop.Recent years, non-fullerene acceptor material is gradually
As the research hotspot in organic solar batteries field, the organic solar batteries based on non-fullerene acceptor have been realized in super
Cross 12% incident photon-to-electron conversion efficiency[8-10].According to the difference of molecular structure, non-fullerene acceptor material can be mainly divided into polymerization
Two class of object and small molecule.Polymer receptoroid material determines the material of different batches preparation due to its design feature and synthesis technology
Expect the disadvantages of there are molecular weight distribution unevenness, later period separating-purifying difficulty, poor repeatability, restricts its application.With polymer phase
Than small molecule material has specific molecular structure, and preparation and purifying technique are simple, therefore too based on small organic molecule receptor
Positive energy battery recently becomes one of the research hotspot in the field.
Indeno thiophene has stronger conjugated system, and excellent charge-transporting is cheap and easy to get, and indeno thiophene is answered extensively
Construction unit for small molecule photovoltaic material.In order to develop the maximum potential of this material, researcher uses many methods
It is modified, such as：Wang etc. is developed using indeno thiophene as the donor material of the p-type polymer of construction unit, preparation
Organic battery efficiency be more than 9.0%, open-circuit voltage (V oc) is up to 1.0V.Show that indeno thiophene is to construct organic semiconductor material
The effective electron donor unit of material[11-12].Zheng etc. develops n type small molecule receptor ITDI using indeno thiophene as core,
Device efficiency is up to 8%, opens pressure and reaches 0.94V[13].Indeno thiophene of the present invention be core, 1,3- indandione, malononitrile and
For 5,6- bis- fluoro- 3- (dicyano methylene) indigo ketone as end-capping group, and using thiophene as bridging, design has synthesized one kind with indeno
Thiophene is the n-type Organic micromolecular semiconductor material of core, to make efficient organic solar batteries device.At present
Device efficiency reaches as high as 6.03%.
Bibliography
[1]Chen,J.-D.；Cui,C.；Li,Y.-Q.；Zhou,L.；Ou,Q.-D.；Li,C.；Li,Y.；Tang,J.-
X.Single-Junction Polymer Solar Cells Exceeding 10%Power Conversion
Efficiency Adv.Mater.2015,27,1035–1041DOI:10.1002/adma.201404535
[2]He,Z.；Xiao,B.；Liu,F.；Wu,H.；Yang,Y.；Xiao,S.；Wang,C.；Russell,T.P.；
Cao,Y.Single-junction Polymer Solar Cells with High Efficiency and
Photovoltage Nat.Photonics 2015,9,174–179DOI:10.1038/nphoton.2015.6
[3]Liu,Y.；Zhao,J.；Li,Z.；Mu,C.；Ma,W.；Hu,H.；Jiang,K.；Lin,H.；Ade,H.；Yan,
H.Aggregation and Morphology Control Enables Multiple Cases of High-
Efficiency Polymer Solar Cells Nat.Commun.2014,55293DOI: 10.1038/ncomms6293
[4]Heeger,A.J.25th Anniversary Article:Bulk Heterojunction Solar
Cells:Understanding the Mechanism of Operation Adv. Mater.2014,26,10–28DOI:
10.1002/adma.201304373
[5]Lu,L.；Zheng,T.；Wu,Q.；Schneider,A.M.；Zhao,D.；Yu,L.Recent Advances
in Bulk Heterojunction Polymer Solar Cells Chem.Rev.2015,115,12666–12731DOI:
10.1021/acs.chemrev.5b00098
[6]You,J.；Dou,L.；Yoshimura,K.；Kato,T.；Ohya,K.；Moriarty,T.；Emery,K.；
Chen,C.-C.；Gao,J.；Li, G.A Polymer Tandem Solar Cell with 10.6%Power
Conversion Efficiency Nat.Commun.2013,41446DOI:10.1038/ncomms2411
[7]Zhan,X.；Facchetti,A.；Barlow,S.；Marks,T.J.；Ratner,M.A.；Wasielewski,
M.R.；Marder,S.R.Rylene and Related Diimides for Organic Electronics
Adv.Mater.2011,23,268–284DOI:10.1002/adma.201001402
[8]Kang,H.；Uddin,M.A.；Lee,C.；Kim,K.-H.；Thanh Luan,N.；Lee,W.；Li,Y.；
Wang,C.；Woo,H.Y.；Kim,B.J.
Determining the Role of Polymer Molecular Weight for High-Performance
All-Polymer Solar Cells:Its Effect on Polymer Aggregation and Phase
Separation J.Am.Chem.Soc.2015,137,2359–2365DOI:10.1021/ja5123182
[9]Nielsen,C.B.；Holliday,S.；Chen,H.-Y.；Cryer,S.J.；McCulloch,I.Non-
Fullerene Electron Acceptors for Use in Organic Solar Cells
Acc.Chem.Res.2015,48,28032812DOI:10.1021/acs.accounts.5b00199
[10]Lin,Y.；Zhan,X.Oligomer Molecules for Efficient Organic
Photovoltaics Acc.Chem.Res.2016,49,175–183 DOI: 10.1021/acs.accounts.5b00363
[11]Wang,M.；Cai,D.；Yin,Z.；Chen,S.-C.；Du,C.-F.；Zheng,Q.Asymmetric-
Indenothiophene-Based Copolymers for Bulk Heterojunction Solar Cells with
9.14%Efficiency Adv.Mater.2016,28,3359-3365DOI:10.1002/adma.201505957
[12]Wang,M.；Wang,Z.；Ma,W.；Chen,S.C.；Zheng,Q.Indenothiophene-Based
Wide Bandgap Copolymer for Polymer Fullerene Solar Cells with 9.01%
Efficiency and 1.0V Open Circuit Voltage Adv.Electron.Mater.2016,21600340
DOI:10.1002/aelm.201600340
[13]Kang,Z.J.；Chen,S.C.；Zheng,Q.D.；Push-Pull Type Non-Fullerene
Acceptors for Polymer Solar Cells:
Effect of the Donor Core DOI:10.1021/acsami.7b05417。
Summary of the invention
Goal of the invention：In order to overcome the deficiencies in the prior art, it is core that the present invention, which provides one kind based on indeno thiophene,
N-type organic small molecular semiconductor of the heart and the preparation method and application thereof, to make efficient organic solar batteries device
Part.Device efficiency reaches as high as 6.03% at present.
Technical solution：To achieve the above object, the technical solution adopted by the present invention is：
It is core based on indeno thiophene, thiophene is bridging, 1,3- indandione, malononitrile and 5, the fluoro- 3- (dicyano of 6- bis-
Methylene) indigo ketone be end group n-type Organic micromolecular semiconductor material preparation method：
(1) by intermediate D (300mg) and 1,3- indandione or other end groups (malononitrile or 5, the fluoro- 3- (dicyan of 6- bis-
Methylene) indigo ketone) with molar ratio 1：5 ratio is added in reaction vessel；
(2) using chloroform as solvent (30 milliliters), and 1 milliliter of pyridine is added as catalyst；
(3) lead to inert gas to exclude in reaction vessel after air, reflux at a temperature of react 24 to 72 hours；
(4) organic phase is extracted with dichloromethane, organic phase obtained by dry, filtering is spin-dried for filtrate and obtains solid, then passes through column
Chromatography purity obtains product compound；
Reaction equation is as follows：
Beneficial effect：N-type organic small molecular semiconductor and its preparation provided by the invention based on indeno thiophene for core
Method and application, compared with prior art, have the advantage that：
The present invention is core, 1,3- indandione, malononitrile and 5, bis- fluoro- 3- (dicyano methylene of 6- using indeno thiophene
Base) as end-capping group, and using thiophene as bridging, design has synthesized a kind of organic as the n- type of core using indeno thiophene indigo ketone
Small molecular semiconductor material.And with nuclear-magnetism, the mass spectral characteristi structure of these molecules, by thermogravimetric analysis its thermal stability,
Its electrochemical properties is characterized with cyclic voltammetry, its photophysical property is characterized by UV-vis absorption spectrum, uses XRD
Its crystallinity and accumulation mode are characterized, characterization result shows this kind of material solution processable, has good light absorptive, excellent
Thermal stability.Organic solar batteries device is prepared for using these materials as acceptor material.Device efficiency highest can at present
Up to 6.03%.
Detailed description of the invention
Fig. 1 is product structure general formula of the invention；
Fig. 2 is the J-V curve for the solar cell device that embodiment is prepared as acceptor material in light-absorption layer；
Fig. 3 is that ultraviolet-visible light area of the compound of embodiment preparation in dichloromethane solution absorbs light map；
Fig. 4 is that the ultraviolet-visible light area of the compound solid film of embodiment preparation absorbs light map；
Fig. 5 is the hydrogen nuclear magnetic resonance spectrogram spectrum of compound A, B, C of embodiment preparation；
Fig. 6 is the mass-spectrogram of compound A, B, C of embodiment preparation；
Fig. 7 is the cyclic voltammetry curve of compound A, B, C of embodiment preparation.
Specific embodiment
The present invention will be further explained with reference to the accompanying drawings and examples.
Embodiment
According to following embodiments, the present invention can be better understood.However, as it will be easily appreciated by one skilled in the art that real
It applies specific material proportion, process conditions and its result described in example and is merely to illustrate the present invention, without that should will not limit
The present invention described in detail in claims processed.
1. the preparation of intermediate D:
Reference literature：Kang,Z.J.；Chen,S.C.；Zheng,Q.D.；Push-Pull Type Non-Fullerene
Acceptors for Polymer Solar Cells:Effect of the Donor Core DOI:10.1021/
acsami.7b05417。
It elaborates below to the embodiment of the present invention, the present embodiment carries out under the premise of the technical scheme of the present invention
Implement, the detailed implementation method and specific operation process are given, but protection scope of the present invention is not limited to following examples
The preparation of compound A, B, C：
The general structure of compound is as shown in Figure 1.
The preparation of compound A：
(1) by intermediate D (300mg) and 1,3- indandione with molar ratio 1：5 ratio is added in reaction vessel；
(2) using chloroform as solvent (30 milliliters), and 1 milliliter of pyridine is added as catalyst；
(3) lead to inert gas to exclude in reaction vessel after air, reflux at a temperature of react 24 to 72 hours；
(4) organic phase is extracted with dichloromethane, organic phase obtained by dry, filtering is spin-dried for filtrate and obtains solid, then passes through column
Chromatography purity obtains product compound A；
Reaction equation is as follows：
The preparation of compound B：
(1) by intermediate D (300mg) and malononitrile with molar ratio 1：5 ratio is added in reaction vessel；
(2) using chloroform as solvent (30 milliliters), and 1 milliliter of pyridine is added as catalyst；
(3) lead to inert gas to exclude in reaction vessel after air, reflux at a temperature of react 24 to 72 hours；
(4) organic phase is extracted with dichloromethane, organic phase obtained by dry, filtering is spin-dried for filtrate and obtains solid, then passes through column
Chromatography purity obtains product compound B；
Reaction equation is as follows：
The preparation of compound C：
(1) by intermediate D (300mg) and 5,6-, bis- fluoro- 3- (dicyano methylene) indigo ketone with molar ratio 1：5 ratio adds
Enter into reaction vessel；
(2) using chloroform as solvent (30 milliliters), and 1 milliliter of pyridine is added as catalyst；
(3) lead to inert gas to exclude in reaction vessel after air, reflux at a temperature of react 24 to 72 hours；
(4) organic phase is extracted with dichloromethane, organic phase obtained by dry, filtering is spin-dried for filtrate and obtains solid, then passes through column
Chromatography purity obtains product compound C；
Reaction equation is as follows：
3. the production of device
(1) commercially available tin indium oxide (ITO) glass is first cleaned with dish washing liquid, then successively with tap water, go from
Sub- water, ethyl alcohol, acetone, isopropanol ultrasonic cleaning.
(2) ZnO of ITO one layer of 30nm thickness of spin coating after dry is spare.
(3) by compound A, B, C acceptor material in embodiment respectively with polymer donor material PTB7-Th, polymer
Acceptor material PCBM (weight ratio 0.15:0.85:1.5) blend solution (20~30mg/mL) is spun on ZnO cathodic modification layer
On, the active layer of photovoltaic device is prepared, the effective area of active layer of photovoltaic device is 4mm2。
(4) MnO of 10nm is deposited under vacuum (2*10-4Pa) environment3Metal Ag of the anode as decorative layer and 100nm
Electrode is as electrode.
(5) use the xenon lamp of the Newport 500W of the optical filter equipped with AM1.5 as simulated solar light source, in 100mW/
cm2Photovoltaic performance test is carried out under light intensity, light intensity is calibrated by standard monocrystalline silicon solar cell；J-V curve uses
Keithley260 measurement.
Test result is as shown in attached drawing 2-7, respectively：
Fig. 2 is the J-V curve for the solar cell device that embodiment is prepared as acceptor material in light-absorption layer；Explanation
It is feasible that object B and C, which is closed, as organic solar batteries acceptor material application.
Fig. 3 is that ultraviolet-visible light area of the compound of embodiment preparation in dichloromethane solution absorbs light map；It says
The solution absorption peak of bright compound A and B under same concentrations are in 550nm or so, but the absorption intensity of compound A is higher, change
Absorption peak red shift about 100nm of the absorption peak with respect to A, B of object C is closed, and the absorption intensity of C is highest in three.
Fig. 4 is that the ultraviolet-visible light area of the compound solid film of embodiment preparation absorbs light map；Illustrate compound
A, the film absorption peak position of B 550nm or so and and similar intensity, the film absorption peak of compound C is about with respect to A, B
Red shift 200nm, three's absorption intensity are close.Know that the optical band gap of compound A, B are about 1.77eV, chemical combination by calculating
The optical band gap of object C is about 1.38eV.
Fig. 5 is the hydrogen nuclear magnetic resonance spectrogram spectrum of compound A, B, C of embodiment preparation；Illustrate that synthesized compound is determined as
Target compound, and purity is higher.
Fig. 6 is the mass-spectrogram of compound A, B, C of embodiment preparation；Illustrate that synthesized compound is determined as target chemical combination
Object, and purity is higher.
Fig. 7 is the cyclic voltammetry curve of compound A, B, C of embodiment preparation.Illustrate by calculating：Compound A's
HOMO energy level is -5.42eV, and lumo energy is -3.65eV.The HOMO energy level of compound B be -5.47eV, lumo energy be -
3.70eV.The HOMO energy level of compound C is -5.63eV, and lumo energy is -4.25 eV.
The above is only a preferred embodiment of the present invention, it should be pointed out that：For the ordinary skill people of the art
For member, various improvements and modifications may be made without departing from the principle of the present invention, these improvements and modifications are also answered
It is considered as protection scope of the present invention.
Claims (8)
1. it is a kind of based on indeno thiophene be core n-type organic small molecular semiconductor, it is characterised in that：It is based on indeno thiophene
Core, using thiophene as bridging, with 1,3- indandione or malononitrile or 5, bis- fluoro- 3- (dicyano methylene) indigo ketone of 6- is end
Base.
2. it is according to claim 1 based on indeno thiophene be core n-type organic small molecular semiconductor, it is characterised in that：
General structure is as follows：
Wherein,Concrete structure formula includes：
3. the preparation side according to claim 1 or 2 based on the n-type organic small molecular semiconductor that indeno thiophene is core
Method, it is characterised in that：Include the following steps：
(1) by intermediate D and 1,3- indandione or malononitrile or 5,6- bis- fluoro- 3- (dicyano methylene) indigo ketone is with molar ratio
1：5 ratio is added in reaction vessel；Wherein, the intermediate D structural formula is：
(2) using chloroform as solvent, and pyridine is added as catalyst；
(3) lead to inert gas to exclude in reaction vessel after air, reflux at a temperature of react 24 to 72 hours；
(4) organic phase is extracted with dichloromethane, organic phase obtained by dry, filtering is spin-dried for filtrate and obtains solid, then passes through column chromatography
Purification obtains product.
4. the preparation method according to claim 3 based on the n-type organic small molecular semiconductor that indeno thiophene is core,
It is characterized in that：Reaction equation is：
5. the preparation method according to claim 3 based on the n-type organic small molecular semiconductor that indeno thiophene is core,
It is characterized in that：The usage ratio of the intermediate D and solvent is：D300 milligrams of intermediate corresponding 30 milliliters of chloroform of additions.
6. the preparation method according to claim 5 based on the n-type organic small molecular semiconductor that indeno thiophene is core,
It is characterized in that：The catalyst amount is 1 milliliter.
7. it is according to claim 1 or 2 based on indeno thiophene be core n-type organic small molecular semiconductor organic non-
Application in fullerene solar battery, it is characterised in that：As acceptor material in light-absorption layer in organic non-fullerene solar energy
Application in battery.
8. it is according to claim 7 based on indeno thiophene be core n-type organic small molecular semiconductor in organic non-fowler
Application in alkene solar battery, it is characterised in that：The preparation method of photovoltaic device includes the following steps：
(1) ZnO of one layer of 30nm thickness of spin coating is spare after ITO is cleaned and dried；
(2) by this based on indeno thiophene be core n-type small organic molecule acceptor material respectively with polymer donor material
PTB7-Th, polymeric acceptor material PCBM is according to weight ratio 0.15:0.85:1.5 mixed blend solutions (20~30mg/mL)
It is spun in ZnO cathodic modification layer, prepares the active layer of photovoltaic device；
(3) MnO of 10nm is deposited under vacuum conditions3Anode is as the metal Ag electrode of decorative layer and 100nm as electrode, light
The effective area of active layer for lying prostrate device is 4mm2。
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109980090A (en) * | 2019-03-20 | 2019-07-05 | 华南理工大学 | A kind of efficient ternary organic photovoltaic cell and preparation method thereof |
| CN113345919A (en) * | 2021-05-25 | 2021-09-03 | 深圳市华星光电半导体显示技术有限公司 | Display panel and manufacturing method thereof |
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| ZHENJING KANG等: "Push−Pull Type Non-Fullerene Acceptors for Polymer Solar Cells:Effect of the Donor Core", 《ACS APPLIED MATERIALS & INTERFACES》 * |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109980090A (en) * | 2019-03-20 | 2019-07-05 | 华南理工大学 | A kind of efficient ternary organic photovoltaic cell and preparation method thereof |
| CN113345919A (en) * | 2021-05-25 | 2021-09-03 | 深圳市华星光电半导体显示技术有限公司 | Display panel and manufacturing method thereof |
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