WO2016175573A2 - Composé et cellule solaire organique le comprenant - Google Patents

Composé et cellule solaire organique le comprenant Download PDF

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WO2016175573A2
WO2016175573A2 PCT/KR2016/004447 KR2016004447W WO2016175573A2 WO 2016175573 A2 WO2016175573 A2 WO 2016175573A2 KR 2016004447 W KR2016004447 W KR 2016004447W WO 2016175573 A2 WO2016175573 A2 WO 2016175573A2
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group
substituted
unsubstituted
same
formula
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PCT/KR2016/004447
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WO2016175573A3 (fr
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임보규
이재철
이지영
김연신
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주식회사 엘지화학
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Priority claimed from KR1020160049483A external-priority patent/KR101863435B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to EP16786759.7A priority Critical patent/EP3290422B1/fr
Priority to US15/559,377 priority patent/US10439153B2/en
Priority to CN201680021330.6A priority patent/CN107466295B/zh
Publication of WO2016175573A2 publication Critical patent/WO2016175573A2/fr
Publication of WO2016175573A3 publication Critical patent/WO2016175573A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • 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
    • H10K85/611—Charge transfer complexes
    • 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
    • H10K30/20—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising organic-organic junctions, e.g. donor-acceptor junctions
    • 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
    • H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
    • 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
    • H10K30/50—Photovoltaic [PV] devices
    • 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

Definitions

  • the present specification relates to a compound and an organic solar cell including the same.
  • Solar cells are devices that can directly convert solar energy into electrical energy by applying the photovoltaic effect.
  • Solar cells can be divided into inorganic solar cells and organic solar cells according to the material constituting the thin film.
  • Typical solar cells are made of p-n junctions by doping crystalline silicon (Si), an inorganic semiconductor. Electrons and holes generated by absorbing light diffuse to the p-n junction and are accelerated by the electric field to move to the electrode.
  • the power conversion efficiency of this process is defined as the ratio of the power given to the external circuit and the solar power entered into the solar cell, and is currently achieved by 24% when measured under standardized virtual solar irradiation conditions.
  • organic semiconductor solar cell which is easy to process, cheap and has various functions, has been spotlighted as a long-term alternative energy source.
  • An object of the present specification is to provide a compound and an organic solar cell including the same.
  • n1 is an integer of 1 to 3
  • n1, m2, p1 and p2 are each an integer of 0 to 3
  • n1, m1, m2, p1 and p2 are 2 or more, the structures in the two or more brackets are the same or different from each other,
  • Push is one of the following structures
  • X1 to X4 are the same as or different from each other, and are each independently CRR ', NR, O, SiRR', PR, S, GeRR ', Se or Te,
  • R, R ', R1 to R8, A3 and A4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsub
  • A1 and A2 are the same as or different from each other, and are each independently represented by the following formula (2),
  • r1 is an integer of 0 to 3
  • Z1 to Z5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substi
  • Linker1 and Linker2 are the same as or different from each other, are divalent linking groups
  • Pull1 and Pull2 are the same as or different from each other, and have an electronic acceptor structure.
  • the present specification is one electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode and including a photoactive layer, wherein at least one of the organic material layers includes the compound described above.
  • Compounds according to an exemplary embodiment of the present specification includes a push structure having an electron donor property and a pull structure having a deployment acceptor property.
  • it comprises a linker connecting the Push and Pull excellent in planarity, the formed excitons (exciton) can be quickly moved in the molecule, can maximize the polarization of the excitons, can have a low bandgap characteristics.
  • the compound according to an exemplary embodiment of the present invention includes a structure of the formula (2) which is a side chain (Bulky) side chain (Bulky) in the push of Formula 1, solubility and viscosity may be improved, the compound It is possible to reduce the interaction of the liver, thereby suppressing the aggregation, and thus, using the formula (1) including the formula (2) as a donor (acceptor) material and bulk-heterojunction (Bulk-heterojunction) film When forming, it can suppress that donor size becomes large.
  • the formula (2) which is a side chain (Bulky) side chain (Bulky) in the push of Formula 1
  • Push may impart elasticity of the compound.
  • the compound may be used as an organic material layer of the organic solar cell, and the organic solar cell including the same may exhibit excellent characteristics such as increase in open voltage and short circuit current and / or increase in efficiency.
  • the compound according to the exemplary embodiment of the present specification may be used alone or in a mixture with other materials in an organic solar cell, and the life of the device may be expected to be improved due to an improvement in efficiency, thermal stability of the compound, and the like.
  • FIG. 1 illustrates an organic solar cell according to an exemplary embodiment of the present specification.
  • FIG. 10 is a diagram showing an NMR spectrum of Compound A-2.
  • FIG. 11 is a diagram showing an MS spectrum of Compound A-3.
  • FIG. 13 is a diagram showing an MS spectrum of Compound 1.
  • FIG. 14 is a diagram showing an MS spectrum of Compound 2.
  • FIG. 16 is a diagram showing a UV-vis absorption spectrum of Compound 2.
  • FIG. 17 is a diagram showing current density by voltage of an organic solar cell according to Experimental Example 1.
  • FIG. 18 is a diagram showing current according to potential of compound 2.
  • adjacent means a substituent substituted on an atom directly connected to an atom to which the substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on an atom to which the substituent is substituted.
  • two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups.
  • substituted means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
  • the term "substituted or unsubstituted” is deuterium; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; Hydroxyl group; An alkyl group; Cycloalkyl group; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Alkenyl groups; Silyl groups; Boron group; Amine group; Aryl phosphine group; Phosphine oxide groups; Aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group or substituted with a substituent to which two or more substituents in the above-described substituents are connected, or does not have any substituents.
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
  • the halogen group may be fluorine, chlorine, bromine or iodine.
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C30. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the amide group may be substituted with nitrogen of the amide group is hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C30. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the ester group may be substituted with oxygen of the ester group having a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms.
  • it may be a compound of the following structural formula, but is not limited thereto.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 30.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-o
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. It is not.
  • the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like It may be, but is not limited thereto.
  • the amine group is -NH 2 ; Alkylamine group; N-arylalkylamine group; Arylamine group; N-aryl heteroaryl amine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, carbon number is not particularly limited, but is preferably 1 to 30.
  • Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group. , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group and the like, but is not limited thereto.
  • the N-alkylarylamineamine group means an amine group in which an alkyl group and an aryl group are substituted for N of the amine group.
  • the N-arylheteroarylamine group means an amine group in which an aryl group and a heteroaryl group are substituted for N in the amine group.
  • the N-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroarylamine group are substituted for N of the amine group.
  • the alkyl group in the alkylamine group, the N-arylalkylamine group, the alkylthioxy group, the alkyl sulfoxy group, and the N-alkylheteroarylamine group is the same as the example of the alkyl group described above.
  • the alkyl thioxy group includes a methyl thioxy group, an ethyl thioxy group, a tert-butyl thioxy group, a hexyl thioxy group, an octyl thioxy group
  • the alkyl sulfoxy group includes mesyl, ethyl sulfoxy, propyl sulfoxy, and butyl sulfoxy groups. Etc., but is not limited thereto.
  • the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 30.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
  • the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
  • the present invention is not limited thereto.
  • the boron group may be -BR 100 R 101 , wherein R 100 and R 101 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • phosphine oxide groups include, but are not limited to, diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like.
  • the aryl group may be monocyclic or polycyclic.
  • the aryl group is a monocyclic aryl group
  • carbon number is not particularly limited, but is preferably 6 to 30 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-30.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
  • the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group, N-arylalkylamine group, N-arylheteroarylamine group, and arylphosphine group is the same as the examples of the aryl group described above.
  • the aryloxy group may be a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group, and the like.
  • arylthioxy group examples include a phenylthioxy group and 2- The methylphenyl thioxy group, 4-tert- butylphenyl thioxy group, etc. are mentioned,
  • An aryl sulfoxy group includes a benzene sulfoxy group, p-toluene sulfoxy group, etc., but is not limited to this.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group.
  • the arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
  • the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
  • the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. Although carbon number is not particularly limited, it is preferably 2 to 30 carbon atoms, the heteroaryl group may be monocyclic or polycyclic.
  • heterocyclic group examples include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Zolyl group, acridil group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group.
  • the heteroarylamine group including two or more heteroaryl groups may simultaneously include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group.
  • the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.
  • heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the heteroaryl group described above.
  • the heterocyclic group may be monocyclic or polycyclic, may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the heteroaryl group.
  • Push has an oxidation characteristic in the heterocyclic compound.
  • Pull1 and Pull2 has a reduction (reduction) property in the heterocyclic compound.
  • the push, pull1, and pull2 are measured by cyclic voltammetry (CV)
  • the push has a relatively oxidative property compared to the pull1 and pull2
  • Pull1 and Pull2 are relatively reducing compared to Push.
  • the oxidation characteristics and the reduction characteristics are relative to the push, but the oxidation characteristics, but may also have a reduction characteristic, Pull1 and Pull2 may have a reduction characteristic, but may also have an oxidation characteristic.
  • Push acts as an electron donor relatively
  • Pull1 and Pull2 act as electron acceptors.
  • the present specification introduces Linker1 and Linker2 having relatively high planarity and having a conjugated structure (conjugation) between the Push and Pull1 and Pull2, so that electrons move quickly in the compound in the Pull1 and Pull2 directions, thereby concentrating electrons. It can be maximized.
  • the formed excitons can move quickly in the molecule, and can maximize the polarization of the excitons, which can have a low bandgap characteristic.
  • the energy level means the magnitude of energy. Therefore, even when the energy level is displayed in the negative (-) direction from the vacuum level, the energy level is interpreted to mean the absolute value of the corresponding energy value.
  • the HOMO energy level means the distance from the vacuum level to the highest occupied molecular orbital.
  • the LUMO energy level means the distance from the vacuum level to the lowest unoccupied molecular orbital.
  • the compound according to an exemplary embodiment of the present specification includes a structure represented by the following Formula 2 which is a side chain of a bulky Push, solubility and viscosity may be improved.
  • the compound according to the exemplary embodiment of the present specification includes a structure represented by the following Chemical Formula 2, which is a side chain of a bulky Push, and thus, a backbone of an electron donor in a device. It is possible to suppress the aggregation between the backbone, thereby suppressing aggregation, and thus, using the above Chemical Formula 1 including the following Chemical Formula 2 as a donor, the acceptor material and the bulk-heterojunction -heterojunction) When the film is formed, the size of the donor can be suppressed to be huge.
  • Push may impart elasticity of the compound. In this case, it can be used as a material of the flexible element.
  • the Push is a substituted or unsubstituted arylene group; And a divalent heterocyclic group including one or more of substituted or unsubstituted N, O, S, Si, and Ge.
  • the Push is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; And a substituted or unsubstituted N, O, S, Si, Ge includes one or two or more in the group consisting of divalent heterocyclic group having 2 to 30 carbon atoms containing at least one.
  • the push is any one of the following structures.
  • X1 to X4 are the same as or different from each other, and are each independently CRR ', NR, O, SiRR', PR, S, GeRR ', Se or Te,
  • R, R ', R1 to R8, A3 and A4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsub
  • A1 and A2 are the same as or different from each other, and are each independently represented by the following formula (2),
  • r1 is an integer of 0 to 3
  • Z1 to Z5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substi
  • Z1 to Z5 are the same as or different from each other, each independently represent a substituted or unsubstituted alkyl group.
  • Z1 to Z5 are the same as or different from each other, each independently represent a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms.
  • Z1 to Z5 are the same as or different from each other, each independently represent a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms.
  • Z1 to Z5 are the same as or different from each other, and each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms.
  • Z1 to Z5 are the same as or different from each other, each independently represent a substituted or unsubstituted n-hexyl group.
  • Z1 is an n-hexyl group.
  • Z2 is an n-hexyl group.
  • Z3 is an n-hexyl group.
  • Linker1 and Linker2 are the same as or different from each other, each independently represent a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; And a substituted or unsubstituted N, O, S, Si, Ge includes one or two or more in the group consisting of divalent heterocyclic group having 2 to 30 carbon atoms containing at least one.
  • the Linker1 and Linker2 are the same as or different from each other, and each independently one of the following structures.
  • t1, t2 and s1 are each an integer of 1 to 3
  • X10 to X22 are the same as or different from each other, and each independently CR a R b , NR a , O, SiR a R b , PR a , S, GeR a R b , Se, or Te,
  • Y1 and Y2 are the same as or different from each other, and each independently CR ′′, N, SiR ′′, P, or GeR ′′,
  • R a , R b , R ′′, and R 100 to R 114 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; nitrile; nitro, imide, amide, hydroxy, substituted or unsubstituted alkyl; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxide Substituted or unsubstituted aryl sulfoxy group; substituted or unsubstituted alkenyl group; substituted or unsubstituted silyl group; substituted or unsubstituted boron group; substituted
  • Pull1 and Pull2 are the same as or different from each other, each independently represent a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms.
  • Pull1 and Pull2 are the same as or different from each other, and are each independently one of the following structures.
  • b is an integer from 1 to 7
  • c is an integer from 1 to 4,
  • R200 to R205 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substi
  • n2 to n4 m3 to m6 and p3 to p6 are each an integer of 1 to 3,
  • n2 to n4 when n2 to n4, m3 to m6 and p3 to p6 are each 2 or more, the structures in the two or more square brackets are the same or different from each other,
  • Push, Linker1, Linker2, Pull1 and Pull2 are the same as defined in Formula 1,
  • Hydrogen is bonded to the ends of the Linker 1 and Linker 2.
  • Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-4 to 1-6.
  • X1 to X4 are the same as or different from each other, and are each independently CRR ', NR, O, SiRR', PR, S, GeRR ', Se or Te,
  • R, R ', R1 to R8, A3 and A4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsub
  • r11, r21, r31 and r41 are each an integer of 0 to 3
  • Z11 to Z15, Z21 to Z25, Z31 to Z35, and Z41 to Z45 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group;
  • the Linker1 is ego
  • s1 is an integer of 1 to 3
  • X21 and X22 are the same as or different from each other, and each independently CR a R b , NR a , O, SiR a R b , PR a , S, GeR a R b , Se, or Te,
  • Y1 and Y2 are the same as or different from each other, and each independently CR ′′, N, SiR ′′, P, or GeR ′′,
  • R a , R b , R ′′ and R 111 to R 114 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; nitrile; nitro, imide, amide, hydroxy, substituted or unsubstituted alkyl; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxide Substituted or unsubstituted aryl sulfoxy group; substituted or unsubstituted alkenyl group; substituted or unsubstituted silyl group; substituted or unsubstituted boron group; substituted
  • the Linker2 is ego
  • s1 is an integer of 1 to 3
  • X21 and X22 are the same as or different from each other, and each independently CR a R b , NR a , O, SiR a R b , PR a , S, GeR a R b , Se, or Te,
  • Y1 and Y2 are the same as or different from each other, and each independently CR ′′, N, SiR ′′, P, or GeR ′′,
  • R a , R b , R ′′ and R 111 to R 114 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; nitrile; nitro, imide, amide, hydroxy, substituted or unsubstituted alkyl; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxide Substituted or unsubstituted aryl sulfoxy group; substituted or unsubstituted alkenyl group; substituted or unsubstituted silyl group; substituted or unsubstituted boron group; substituted
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-7 to 1-9.
  • X1 to X4 are the same as or different from each other, and are each independently CRR ', NR, O, SiRR', PR, S, GeRR ', Se or Te,
  • R, R ', R1 to R8, A3 and A4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsub
  • r11, r21, r31 and r41 are each an integer of 0 to 3
  • Z11 to Z15, Z21 to Z25, Z31 to Z35, and Z41 to Z45 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group;
  • s11 and s21 are each an integer of 1 to 3,
  • X31, X32, X41 and X42 are the same as or different from each other, and each independently CR a R b , NR a , O, SiR a R b , PR a , S, GeR a R b , Se or Te,
  • Y11, Y12, Y21 and Y22 are the same as or different from each other, and are each independently CR “, N, SiR", P or GeR ",
  • R a , R b , R ′′ R211 to R214 and R311 to R314 are the same as or different from each other, and each independently hydrogen; deuterium; halogen group; nitrile group; nitro group; imide group; amide group; hydroxy group; substituted or unsubstituted Substituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted aryloxy group; substituted or unsubstituted alkylthioxy group; substituted or unsubstituted arylthioxy group; substituted or unsubstituted Substituted or unsubstituted aryl sulfoxy group; substituted or unsubstituted alkenyl group; substituted or unsubstituted silyl group; substituted or unsubstituted boron group; substituted or unsubstituted amine
  • Linker1 is ego
  • t1 and t2 are each an integer of 1 to 3,
  • X10 to X13 are the same as or different from each other, and each independently CR a R b , NR a , O, SiR a R b , PR a , S, GeR a R b , Se, or Te,
  • R a , R b and R 100 to R 104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubsti
  • Linker2 is ego
  • t1 and t2 are each an integer of 1 to 3,
  • X10 to X13 are the same as or different from each other, and each independently CR a R b , NR a , O, SiR a R b , PR a , S, GeR a R b , Se, or Te,
  • R a , R b and R 100 to R 104 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubsti
  • Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-10 to 1-12.
  • X1 to X4 are the same as or different from each other, and are each independently CRR ', NR, O, SiRR', PR, S, GeRR ', Se or Te,
  • R, R ', R1 to R8, A3 and A4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsub
  • r11, r21, r31 and r41 are each an integer of 0 to 3
  • Z11 to Z15, Z21 to Z25, Z31 to Z35, and Z41 to Z45 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group;
  • t11, t12, t21 and t22 are each an integer of 1 to 3
  • X20 to X23 and X30 to X33 are the same as or different from each other, and are each independently CR a R b , NR a , O, SiR a R b , PR a , S, GeR a R b , Se, or Te,
  • R a , R b , R 200 to R 204 and R 300 to R 304 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Sub
  • X1 to X4 is S.
  • R1 and R2 are hydrogen.
  • R3 to R8 are hydrogen.
  • R3, R4, R7, R8, A3 and A4 are hydrogen.
  • Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-13 to 1-15.
  • r11, r21, r31, r41, Z11 to Z15, Z21 to Z25, Z31 to Z35, and Z41 to Z45 are the same as in Chemical Formulas 1-4 to 1-6.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-16 to 1-18.
  • r11, r21, r31, r41, Z11 to Z15, Z21 to Z25, Z31 to Z35 and Z41 to Z45 are the same as those of Chemical Formulas 1-4 to 1-6,
  • s1, s21, X31, X32, X41, X42, Y11, Y12, Y21, Y22 and R211 to R214 and R311 to R314 are the same as defined in Chemical Formulas 1-7 to 1-9.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-19 to 1-21.
  • r11, r21, r31, r41, Z11 to Z15, Z21 to Z25, Z31 to Z35 and Z41 to Z45 are the same as those of Chemical Formulas 1-4 to 1-6,
  • Z11 to Z13, Z21 to Z23, Z31 to Z33 and Z41 to Z43 are the same as or different from each other, each independently represent a substituted or unsubstituted alkyl group.
  • Z11 to Z13, Z21 to Z23, Z31 to Z33 and Z41 to Z43 are the same as or different from each other, and each independently a substituted or unsubstituted straight or branched chain having 1 to 30 carbon atoms It is an alkyl group.
  • Z11 to Z13, Z21 to Z23, Z31 to Z33 and Z41 to Z43 are the same as or different from each other, and each independently a substituted or unsubstituted straight or branched chain having 1 to 20 carbon atoms It is an alkyl group.
  • the Z11 to Z13, Z21 to Z23, Z31 to Z33 and Z41 to Z43 are the same as or different from each other, each independently represent a substituted or unsubstituted straight or branched chain of 1 to 10 carbon atoms It is an alkyl group.
  • Z11 to Z13, Z21 to Z23, Z31 to Z33 and Z41 to Z43 are the same as or different from each other, each independently represent a substituted or unsubstituted n-hexyl group.
  • Z11 to Z13, Z21 to Z23, Z31 to Z33 and Z41 to Z43 are n-hexyl group.
  • r11, r21, r31 and r41 is 0.
  • Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-22 to 1-24.
  • the compound may be prepared based on the preparation examples described below.
  • Compound according to an exemplary embodiment of the present specification is a compound in which an aldehyde group and a halogen group are introduced at the terminal of Linker 1, and an aldehyde group and a halogen group are introduced at the terminal of Linker 2; And Push to form a compound in which an aldehyde group is introduced at each terminal. Thereafter, Pull1 and Pull2 may be introduced to prepare a compound represented by Chemical Formula 1.
  • Compounds according to the present specification can be prepared by multistage chemical reactions. After preparing monomers through alkylation reaction, Grignard reaction, Suzuki coupling reaction, and Still coupling reaction, the final compound is obtained through carbon-carbon coupling reaction such as steel coupling reaction. Can be prepared.
  • the substituent to be introduced is a boronic acid or boronic ester compound, it may be prepared through Suzuki coupling, and the substituent to be introduced is tributyltin or trimethyltin.
  • Compound may be prepared through a steel coupling reaction, but is not limited thereto.
  • the first electrode A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode and including a photoactive layer, wherein at least one of the organic material layers includes the compound.
  • the organic solar cell according to the exemplary embodiment of the present specification includes a first electrode, a photoactive layer, and a second electrode.
  • the organic solar cell may further include a substrate, a hole transport layer, and / or an electron transport layer.
  • the organic solar cell when the organic solar cell receives photons from an external light source, electrons and holes are generated between the electron donor and the electron acceptor. The generated holes are transported to the anode through the electron donor layer.
  • the organic material layer includes a hole transporting layer, a hole injection layer, or a layer for simultaneously transporting holes and hole injection, and the hole transporting layer, the hole injection layer, or a layer for both hole transporting and hole injection simultaneously. It includes the compound.
  • the organic material layer includes an electron injection layer, an electron transporting layer, or a layer for simultaneously injecting and transporting electrons
  • the electron injection layer, an electron transporting layer, or a layer for simultaneously injecting and transporting electrons is It includes the compound.
  • FIG. 1 is a view showing an organic solar cell according to an exemplary embodiment of the present specification.
  • the organic solar cell when the organic solar cell receives photons from an external light source, electrons and holes are generated between the electron donor and the electron acceptor. The generated holes are transported to the anode through the electron donor layer.
  • the organic solar cell may further include an additional organic material layer.
  • the organic solar cell may reduce the number of organic material layers by using an organic material having several functions at the same time.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode and the second electrode is an anode.
  • the organic solar cell may be arranged in the order of cathode, photoactive layer and anode, and may be arranged in the order of anode, photoactive layer and cathode, but is not limited thereto.
  • the organic solar cell may be arranged in order of an anode, a hole transport layer, a photoactive layer, an electron transport layer, and a cathode, or may be arranged in the order of a cathode, an electron transport layer, a photoactive layer, a hole transport layer, and an anode. It is not limited to this.
  • the organic solar cell has a normal structure.
  • a substrate, an anode, and an organic material layer including a photoactive layer and a cathode may be stacked in this order.
  • the organic solar cell has an inverted structure.
  • a substrate, a cathode, an organic material layer including a photoactive layer, and an anode may be stacked in this order.
  • the organic solar cell has a tandem structure.
  • the photoactive layer may be one layer or two or more layers.
  • the tandem structure may include two or more photoactive layers.
  • a buffer layer may be provided between the photoactive layer and the hole transport layer or between the photoactive layer and the electron transport layer.
  • a hole injection layer may be further provided between the anode and the hole transport layer.
  • an electron injection layer may be further provided between the cathode and the electron transport layer.
  • the photoactive layer includes one or two or more selected from the group consisting of an electron donor and an acceptor, and the electron donor material includes the compound.
  • the electron acceptor material may be selected from the group consisting of fullerenes, fullerene derivatives, vasocuprones, semiconducting elements, semiconducting compounds, and combinations thereof.
  • fullerene, fullerene derivative PCBM ((6,6) -phenyl-C61-butyric acid-methylester) or PCBCR ((6,6) -phenyl-C61-butyric acid-cholesteryl ester
  • perylene perylene
  • PBI polybenzimidazole
  • PTCBI 3,4,9,10-perylene-tetracarboxylic bis-benzimidazole
  • the electron donor and the electron acceptor constitute a bulk hetero junction (BHJ).
  • BHJ bulk hetero junction
  • Bulk heterojunction means that the electron donor material and the electron acceptor material are mixed with each other in the photoactive layer.
  • the photoactive layer has a bilayer structure including a n-type organic compound layer and a p-type organic compound layer, and the p-type organic compound layer includes the compound.
  • the substrate may be a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness, but is not limited thereto, and the substrate may be any substrate that is commonly used in organic solar cells. Specifically, there are glass or polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polypropylene (PP), polyimide (PI), and triacetyl cellulose (TAC). It is not limited to this.
  • PET polyethylene terephthalate
  • PEN polyethylene naphthalate
  • PP polypropylene
  • PI polyimide
  • TAC triacetyl cellulose
  • the anode electrode may be a transparent and excellent conductive material, but is not limited thereto.
  • Metals such as vanadium, chromium, copper, zinc and gold or alloys thereof;
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO: Al or SNO 2 : Combination of metals and oxides such as Sb;
  • conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto. .
  • the method of forming the anode electrode is not particularly limited, but is applied to one surface of the substrate or coated in a film form using, for example, sputtering, E-beam, thermal deposition, spin coating, screen printing, inkjet printing, doctor blade or gravure printing. It can be formed by.
  • the anode electrode When the anode electrode is formed on the substrate, it may be subjected to cleaning, water removal, and hydrophilic modification.
  • the patterned ITO substrate is sequentially cleaned with a detergent, acetone, isopropyl alcohol (IPA), and then dried in a heating plate for 1 to 30 minutes at 100 to 150 ° C., preferably at 120 ° C. for 10 minutes to remove moisture.
  • IPA isopropyl alcohol
  • the surface of the substrate is modified to be hydrophilic.
  • the bonding surface potential can be maintained at a level suitable for the surface potential of the photoactive layer.
  • Pretreatment techniques for the anode electrode include a) surface oxidation using parallel plate discharge, b) oxidation of the surface through ozone generated using UV ultraviolet light in a vacuum state, and c) oxygen radicals generated by plasma. And oxidation using the same method.
  • One of the above methods can be selected depending on the state of the anode electrode or the substrate. In any case, however, it is desirable to prevent oxygen escape from the surface of the anode electrode or the substrate and to minimize the residual of moisture and organic matter in common. At this time, the substantial effect of the pretreatment can be maximized.
  • a method of oxidizing a surface through ozone generated using UV may be used.
  • the patterned ITO substrate is baked on a hot plate and dried well, then put into a chamber, and a UV lamp is activated to cause oxygen gas to react with UV light.
  • the patterned ITO substrate can be cleaned.
  • the surface modification method of the patterned ITO substrate in this specification does not need to be specifically limited, Any method may be used as long as it is a method of oxidizing a substrate.
  • the cathode electrode may be a metal having a small work function, but is not limited thereto.
  • metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Or a material having a multilayer structure such as LiF / Al, LiO 2 / Al, LiF / Fe, Al: Li, Al: BaF 2 , Al: BaF 2 : Ba, but is not limited thereto.
  • the cathode electrode is 5x10 - may be formed is deposited on the internal heat evaporator showing a degree of vacuum of less than 7 torr, not limited to this method.
  • the hole transport layer and / or electron transport layer material plays a role of efficiently transferring electrons and holes separated in the photoactive layer to the electrode, and the material is not particularly limited.
  • the hole transport layer material may be PEDOT: PSS (Poly (3,4-ethylenediocythiophene) doped with poly (styrenesulfonic acid)), molybdenum oxide (MoO x ); Vanadium oxide (V 2 O 5 ); Nickel oxide (NiO); Tungsten oxide (WO x ), and the like, but is not limited thereto.
  • PSS Poly (3,4-ethylenediocythiophene) doped with poly (styrenesulfonic acid)
  • MoO x molybdenum oxide
  • V 2 O 5 Vanadium oxide
  • NiO Nickel oxide
  • WO x Tungsten oxide
  • the electron transport layer material may be electron-extracting metal oxides, specifically, a metal complex of 8-hydroxyquinoline; Complexes including Alq 3 ; Metal complexes including Liq; LiF; Ca; Titanium oxide (TiO x ); Zinc oxide (ZnO); And cesium carbonate (Cs 2 CO 3 ), and the like, but is not limited thereto.
  • metal oxides specifically, a metal complex of 8-hydroxyquinoline; Complexes including Alq 3 ; Metal complexes including Liq; LiF; Ca; Titanium oxide (TiO x ); Zinc oxide (ZnO); And cesium carbonate (Cs 2 CO 3 ), and the like, but is not limited thereto.
  • the photoactive layer may be formed by dissolving a photoactive material, such as an electron donor and / or an electron acceptor, in an organic solvent and then spin coating, dip coating, screen printing, spray coating, doctor blade, brush painting, or the like. It is not limited to the method.
  • a photoactive material such as an electron donor and / or an electron acceptor
  • FIG. 11 is a diagram showing an MS spectrum of Compound A-3.
  • FIG. 13 is a diagram showing an MS spectrum of Compound 1.
  • FIG. 14 is a diagram showing an MS spectrum of Compound 2.
  • FIG. 16 is a diagram showing a UV-vis absorption spectrum of Compound 2.
  • the UV absorption spectrum of FIG. 16 is an absorption spectrum of Compound 2 in a film state and a solution state, and was analyzed by using a UV-Vis absorption spectrometer, and the results are shown in Table 1 below.
  • FIG. 18 is a diagram illustrating current according to potential of compound 2.
  • Compound 2 and PC 70 BM were dissolved in chlorobenzene (CB) at 1: 1.25 to prepare a composite solution. At this time, the concentration was adjusted to 4 wt%, the organic solar cell was an inverted structure of ITO / ZnO / photoactive layer / MoO 3 / Ag.
  • ITO is a bar type, 1.5 ⁇ 1.5 cm 2 coated glass substrate is distilled water,
  • FIG. 17 is a diagram showing current density by voltage of an organic solar cell according to Experimental Example 1.
  • Voc is an open voltage
  • Jsc is a short-circuit current
  • FF is a fill factor
  • PCE ( ⁇ ) is an energy conversion efficiency.
  • Open voltage and short current are respectively voltage-current
  • the X-axis and Y-axis intercepts in the four quadrants of the density curve.
  • the fill factor is the area of the rectangle drawn inside the curve divided by the product of the short circuit current and the open voltage.

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Abstract

La présente invention porte sur un composé hétérocyclique et sur une cellule solaire organique le comprenant.
PCT/KR2016/004447 2015-04-28 2016-04-28 Composé et cellule solaire organique le comprenant WO2016175573A2 (fr)

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US15/559,377 US10439153B2 (en) 2015-04-28 2016-04-28 Compound and organic solar cell comprising same
CN201680021330.6A CN107466295B (zh) 2015-04-28 2016-04-28 化合物和包含其的有机太阳能电池

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WO2019107790A1 (fr) * 2017-11-28 2019-06-06 주식회사 엘지화학 Couche photoactive et cellule photovoltaïque organique la comprenant
JP2020506252A (ja) * 2017-05-24 2020-02-27 エルジー・ケム・リミテッド 化合物およびこれを含む有機太陽電池
US11502255B2 (en) 2017-11-28 2022-11-15 Lg Chem, Ltd. Photoactive layer and organic solar cell comprising same

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KR101139055B1 (ko) * 2005-11-25 2012-04-30 삼성전자주식회사 신규한 방향족 엔다이인 유도체, 이를 이용한 유기 반도체및 전자소자
DE102013101713B4 (de) * 2013-02-21 2020-10-01 Heliatek Gmbh Photoaktives, organisches Material für optoelektronische Bauelemente
JP2015065266A (ja) * 2013-09-25 2015-04-09 東洋インキＳｃホールディングス株式会社 有機薄膜太陽電池素子用材料およびその用途

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JP2020506252A (ja) * 2017-05-24 2020-02-27 エルジー・ケム・リミテッド 化合物およびこれを含む有機太陽電池
WO2019107790A1 (fr) * 2017-11-28 2019-06-06 주식회사 엘지화학 Couche photoactive et cellule photovoltaïque organique la comprenant
US11502255B2 (en) 2017-11-28 2022-11-15 Lg Chem, Ltd. Photoactive layer and organic solar cell comprising same

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