WO2015190762A2 - Dérivé à cycles fusionnés et cellule solaire organique le comprenant - Google Patents

Dérivé à cycles fusionnés et cellule solaire organique le comprenant Download PDF

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WO2015190762A2
WO2015190762A2 PCT/KR2015/005678 KR2015005678W WO2015190762A2 WO 2015190762 A2 WO2015190762 A2 WO 2015190762A2 KR 2015005678 W KR2015005678 W KR 2015005678W WO 2015190762 A2 WO2015190762 A2 WO 2015190762A2
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WO2015190762A3 (fr
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임보규
방지원
이재철
이지영
김진석
조근
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주식회사 엘지화학
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    • 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
    • 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
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero 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
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • 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
    • 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
    • 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 condensed ring derivative and an organic solar cell including the same.
  • Organic 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 disclosure is to provide a condensed ring derivative and an organic solar cell including the same.
  • n1 and n2 are each an integer of 0 to 3
  • n1 and n2 are each 2 or more, the structures in the two or more parentheses are the same or different from each other,
  • X1 to X4 are the same as or different from each other, and each independently CRR ', NR, O, SiRR', PR, S, GeRR ', Se or Te,
  • Y1 to Y4 are the same as or different from each other, and each independently CR ′′, N, SiR ′′, P, or GeR ′′,
  • R, R ', R "and R1 to R8 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; nitrile; nitro, imide, amide, hydroxy, substituted or unsubstituted alkyl; Or an unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group Substituted or unsubstituted aryl sulfoxy group; substituted or unsubstituted alkenyl group; substituted or unsubstituted silyl group; substituted or unsubstituted boron group; substituted or unsubstituted alkylamine group; substituted or
  • Ar1 and Ar2 are the same as or different from each other, and each independently one of the following structures,
  • a is an integer from 1 to 7
  • b and c are each an integer of 1 to 4,
  • R13 to R23 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
  • 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 condensed ring derivative described above. do.
  • Condensed ring derivatives according to one embodiment of the present specification can introduce a [Push] having an electron donor property and Ar1 and Ar2 having an electron acceptor property to lower the HOMO level. In this case, high driving voltage can be expected.
  • the compound according to the exemplary embodiment of the present specification has a red shift in the absorption spectrum, resulting in a low LUMO energy level value, and the band gap is reduced to absorb a wide area of light, Efficiency can have a positive impact.
  • a condensed ring including [Push] and X3 and a condensed ring including X4 may be directly connected to induce more effective electron transfer.
  • the condensed ring derivative according to an exemplary embodiment of the present specification is excellent in crystallinity, it can be expected to increase the fill factor (FF).
  • the condensed ring derivative 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.
  • Condensed ring derivative according to one embodiment of the present specification can be used alone or mixed with other materials in an organic solar cell, and is expected to improve the life of the device due to the improvement of efficiency, thermal stability of the condensed ring derivative, etc. Can be.
  • FIG. 1 illustrates an organic solar cell according to an exemplary embodiment of the present specification.
  • FIG. 13 is a view comparing UV spectra of Chemical Formulas 1-1-1 and Chemical Formula 2 in a film state.
  • FIG. 15 is a diagram illustrating an electrochemical measurement result (cyclic voltametry) of Chemical Formula 2.
  • FIG. 15 is a diagram illustrating an electrochemical measurement result (cyclic voltametry) of Chemical Formula 2.
  • 16 is a diagram illustrating current densities according to voltages of organic solar cells using Chemical Formulas 1-1-1 and Chemical Formula 2;
  • it acts as an electron donor in the [Push] condensed ring derivative.
  • the highest occupied molecular orbital (HOMO) energy level of [Push] is 5.0 eV to 6.0 eV.
  • the band gap of the [Push] is 2 eV to 4.5 eV.
  • Ar1 and Ar2 act as electron acceptors in the condensed ring derivative. Due to Ar1 and Ar2 as electron acceptors, the band gap of the condensed ring derivative can be reduced, and since dipoles are formed at the ends of the condensed ring derivative, electrons can be efficiently concentrated. Therefore, since electrons are concentrated at the terminal of the condensed ring derivative according to the exemplary embodiment of the present specification, when introduced into the organic material layer of the device, the terminal of the condensed ring derivative may be in contact with the electron acceptor material in the device. There is an effect that the electron transfer to the material is easy.
  • Condensed ring derivatives relatively [Push] acts as a relatively electron donor, Ar1 and Ar2 acts as an electron acceptor. In this case, electrons in the lower unoccupied molecular orbital (LUMO) state are relatively localized to Ar1 and Ar2. For this reason, polarization exists between [Push] and Ar1 or Ar2.
  • LUMO unoccupied molecular orbital
  • the present specification introduces a linker having excellent planarity and having a conjugated structure (conjugation) between the [Push] and Ar1 or Ar2, so that the electrons move quickly in the condensed ring derivative in the Ar1 or Ar2 direction, Maximize your concentration.
  • the formed excitons can be quickly moved in the molecule, and the polarization of the excitons can be maximized, thereby having low bandgap characteristics.
  • the condensed ring derivative according to the exemplary embodiment of the present specification has a [Push] structure, a ring including X3, and a ring including X4 is directly connected.
  • a [Push] structure As described above, when the ring containing [Push] and X3 or the ring containing X4 is directly bonded, another spacer or linker is included between the [Push] structure and the ring containing X3 or the ring containing X4. Red shift can be observed than when.
  • 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 [Push] structure which acts as an electron donor in the present specification may mean a structure having oxidation in an electrochemical measurement result (Cyclic voltammetry).
  • Ar1 and Ar2 serving as electron acceptors may refer to a structure having reduction in electrochemical measurement results (Cyclic voltammetry).
  • the structures acting as electron acceptors and electron donors are not limited to those observed only for oxidation or reduction, respectively.
  • the [Push] is a substituted or unsubstituted arylene group; And one or two or more from the group consisting of a substituted or unsubstituted divalent heterocyclic group.
  • the [Push] is any one of the following structures.
  • d and d ' are each an integer of 1 to 3
  • X10 to X13 are the same as or different from each other, and each independently CRaRb, NRa, O, SiRaRb, PRa, S, GeRaRb, Se, or Te,
  • Y10 and Y11 are the same as or different from each other, and each independently CRc, N, SiRc, P, or GeRc,
  • Ra, Rb, Rc and R100 to R103 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 unsubstitute
  • the [Push] is to be.
  • the [Push] is to be.
  • the condensed ring derivative represented by Formula 1 is represented by the following Formula 1-1 or Formula 1-2.
  • n1 and n2 X1 to X4, Y1 to Y4, R1 to R8, Ar1 and Ar2 are the same as defined in Formula 1,
  • X10 to X13 are the same as or different from each other, and each independently CRaRb, NRa, O, SiRaRb, PRa, S, GeRaRb, Se, or Te,
  • Y10 and Y11 are the same as or different from each other, and each independently CRc, N, SiRc, P, or GeRc,
  • Ra, Rb, Rc and R100 to R103 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 unsubstitute
  • 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.
  • substituted or unsubstituted is deuterium; Halogen group; An alkyl group; Alkenyl groups; An alkoxy group; Ester group; Carbonyl group; Carboxyl groups; Hydroxyl group; Cycloalkyl group; Silyl groups; Aryl alkenyl group; Aryloxy group; Alkyl thioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Boron group; Alkylamine group; Aralkyl amine groups; Arylamine group; Heterocyclic group; Arylamine group; Aryl group; Nitrile group; Nitro group; Hydroxyl group; And one or more substituents selected from the group consisting of a heterocyclic group, or two or more substituents among the substituents exemplified above are substituted with a substituent or have no substituent.
  • 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 and can be interpreted as a substituent to which two phenyl groups are linked.
  • the substituents may be substituted or unsubstituted with additional substituents.
  • 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-C25. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the amide group may be substituted with one or two of the nitrogen of the amide group is hydrogen, a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, 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 50.
  • 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 3 to 60 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. Do 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-C20. 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 alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40.
  • 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 aryl group may be a monocyclic aryl group or a polycyclic aryl group, and includes a case where a substituent such as an alkyl group having 1 to 25 carbon atoms or an alkoxy group having 1 to 25 carbon atoms is substituted.
  • the aryl group in the present specification may mean an aromatic ring.
  • the aryl group is a monocyclic aryl group
  • carbon number is not particularly limited, but preferably 6 to 25 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 C10-24.
  • 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 heterocyclic group is a structure containing at least one hetero element instead of a carbon atom, for example, a ring structure including O, N, Se, Ge, Si, and S, etc., although the carbon number is not particularly limited, but carbon number It is preferable that it is 2-60.
  • heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenan
  • the heterocyclic group may be monocyclic or polycyclic, and may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic.
  • 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.
  • aryl amine group examples include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl-biphenylamine, 9-methyl-anthra Cenylamine, diphenyl amine group, phenyl naphthyl amine group, ditolyl amine group, phenyl tolyl amine group, carbazole and triphenyl amine group and the like, but are not limited thereto.
  • heteroaryl group in the heteroarylamine group may be selected from the examples of the heterocyclic group described above.
  • the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group and aralkylamine group is the same as the aryl group described above.
  • the aryloxy group phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyl Oxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy, 2-anthryl Oxy, 9-anthryloxy, 1-phenanthryloxy, 3-phenanthryloxy, 9-phenanthryloxy, and the like.
  • arylthioxy group examples include a phenylthioxy group, 2-methylphenylthioxy group, and 4-tert-butylphenyl.
  • Thioxy groups and the like, and aryl sulfoxy groups include, but are not limited to, benzene sulfoxy groups and p-toluene sulfoxy groups.
  • the alkyl group in the alkyl thioxy group and the alkyl sulfoxy group is the same as the example of the alkyl group mentioned 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.
  • X1 to X4 are S,
  • Y1 to Y4 are N
  • Ar1 and Ar2 are the same as or different from each other, and each independently Ar1 and Ar2 are the same or different from each other, and each independently ; ; or ego,
  • R5 to R8 are the same as or different from each other, and each independently hydrogen; Halogen group; Or a substituted or unsubstituted alkoxy group,
  • R13, R14, R22 and R23 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms,
  • [Push] is a heterocyclic group containing one or more S atoms, the heterocyclic group is a substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • R5 to R8 are the same as or different from each other, and each independently hydrogen; Halogen group; Or a substituted or unsubstituted alkoxy group.
  • At least one of R5 to R8 is a halogen group; Or a substituted or unsubstituted alkoxy group.
  • At least one of R5 to R8 is a halogen group; Or a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms.
  • planarity is improved due to the non-bonding interaction between the [Push] structure of the condensed ring derivative and the ring including X3 or the ring including X4, thereby improving crystallinity. .
  • an improvement in the characteristics of the current can be expected.
  • excitons formed by the improvement of the planarity between Ar1 and Ar2 acting as electron acceptors and electron acceptors in the compound can be stably localized quickly in the molecule. have. Therefore, the polarization of the exciton can be maximized, and can have a low bandgap characteristic.
  • R5 is hydrogen
  • R5 is a substituted or unsubstituted alkoxy group.
  • R5 is a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
  • R5 is a substituted or unsubstituted octoxy group.
  • R5 is an octoxy group.
  • R6 is a halogen group.
  • R6 is fluorine
  • R6 is a substituted or unsubstituted alkoxy group.
  • R6 is a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
  • R6 is a substituted or unsubstituted octoxy group.
  • R6 is an octoxy group.
  • R7 is a halogen group.
  • R7 is fluorine
  • R7 is a substituted or unsubstituted alkoxy group.
  • R7 is a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
  • R7 is a substituted or unsubstituted octoxy group.
  • R7 is an octoxy group.
  • R8 is hydrogen
  • R8 is a substituted or unsubstituted alkoxy group.
  • R8 is a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
  • R8 is a substituted or unsubstituted octoxy group.
  • R8 is an octoxy group.
  • X1 is S.
  • X2 is S.
  • X3 is S.
  • X4 is S.
  • n1 is 2.
  • n1 is 1.
  • n2 is two.
  • n2 is one.
  • R1 is hydrogen
  • R2 is hydrogen
  • R3 is hydrogen
  • R4 is hydrogen
  • Y1 is N.
  • Y2 is N.
  • Y3 is N.
  • Y4 is N.
  • Ar1 is to be.
  • Ar1 is to be.
  • Ar1 is to be.
  • Ar2 is to be.
  • Ar2 is to be.
  • Ar2 is to be.
  • [Push] is a heterocyclic group containing one or more S atoms.
  • R100 is hydrogen
  • R101 is hydrogen
  • R102 is hydrogen
  • R103 is hydrogen
  • X10 is S.
  • X11 is SiRaRb.
  • X11 is S.
  • X12 is SiRaRb.
  • X13 is S.
  • Y10 is CRc.
  • Y11 is CRc.
  • Ra, Rb and Rc are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • Ra, Rb and Rc are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted heteroring group.
  • Ra and Rb are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group.
  • Ra and Rb are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
  • Ra is a substituted or unsubstituted alkyl group.
  • Ra is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
  • Ra is a substituted or unsubstituted octyl group.
  • Ra is an octyl group.
  • Rb is a substituted or unsubstituted alkyl group.
  • Rb is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
  • Rb is a substituted or unsubstituted octyl group.
  • Rb is an octyl group.
  • Rc is a substituted or unsubstituted heteroring group.
  • Rc is a heterocyclic group including a substituted or unsubstituted S atom.
  • Rc is a heterocyclic group including an S atom unsubstituted or substituted with an alkyl group.
  • Rc is a thiophene group substituted with an alkyl group.
  • Rc is a thiophene group substituted with a 2-ethylhexyl group.
  • R13, R14, R22, and R23 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms.
  • R13 is hydrogen
  • R14 is a substituted or unsubstituted alkyl group.
  • R14 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
  • R14 is a substituted or unsubstituted octyl group.
  • R14 is a substituted or unsubstituted ethyl group.
  • R14 is an ethyl group.
  • R14 is an octyl group.
  • R22 is a substituted or unsubstituted alkyl group.
  • R22 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
  • R22 is a substituted or unsubstituted octyl group.
  • R22 is a substituted or unsubstituted ethyl group.
  • R22 is an ethyl group.
  • R23 is a substituted or unsubstituted alkyl group.
  • R23 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
  • R23 is a substituted or unsubstituted octyl group.
  • R23 is a substituted or unsubstituted ethyl group.
  • R23 is an ethyl group.
  • the condensed ring derivative represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1-1 to 1-1-5.
  • the condensed ring derivative may be prepared based on the preparation examples described below.
  • Condensed ring derivative according to one embodiment of the present specification is to combine a compound containing a dioxolane group introduced at one end of the structure in parentheses of n1 and a compound containing a X3 introduced at both ends with a dioxolane group, The structure which introduce
  • a structure including the structure in parentheses of n2 and X4 is prepared.
  • the two compounds prepared above and [Push] are combined to prepare a compound in which an aldehyde group is introduced at each terminal.
  • Ar1 and Ar2 may be introduced to prepare not only the condensed ring derivative represented by one of Formulas 1-1-1 to 1-1-5, but also the condensed ring derivative represented by Formula 1.
  • Condensed ring derivatives according to the present specification can be prepared by a multi-step chemical reaction. Monomers are prepared through alkylation, Grignard reaction, Suzuki coupling reaction, and Still coupling reaction, and then condensation through carbon-carbon coupling reaction such as steel coupling reaction. Ring derivatives 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 condensed ring derivative.
  • 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 simultaneously transporting holes and hole injection, It includes the condensed ring derivative.
  • 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 condensed ring derivative.
  • 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.
  • the organic solar cell has an inverted structure.
  • the organic solar cell has a tandem structure.
  • the photoactive layer may be one layer or two or more 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 condensed ring derivative.
  • 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 an n-type organic compound layer and a p-type organic compound layer, and the p-type organic compound layer includes the condensed ring derivative.
  • 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 generated by plasma. And oxidation using radicals.
  • 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; LiF / Al, LiO 2 / Al, LiF / Fe, Al: Li, Al: BaF 2 , Al: BaF 2
  • It may be a material of a multi-layer structure such as, 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)), 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.
  • 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
  • the compound of Formula 1-1-1 has a lower bandgap than the compound of Formula 2, and the extinction coefficient value is about two times higher.
  • FIG. 13 is a view comparing UV spectra of Chemical Formulas 1-1-1 and Chemical Formula 2 in a film state.
  • the compound of Formula 1-1-1 has a low bandgap.
  • the vibration peak (vibronic peak) is seen to increase, it can be seen that the crystallinity of the general formula (1-1-1) is high.
  • the organic solar cell including the compound of Formula 1-1-1 can be expected to improve the current characteristics.
  • FIG. 15 is a diagram illustrating an electrochemical measurement result (cyclic voltametry) of Chemical Formula 2.
  • FIG. 15 is a diagram illustrating an electrochemical measurement result (cyclic voltametry) of Chemical Formula 2.
  • the organic solar cell including the compound of Formula 1-1-1 can be expected to improve the voltage characteristics.
  • Condensed ring derivative 1 and PCBM prepared in the above Example 1 dissolved in chlorobenzene (Chlorobenzene, CB) 1: 2 to prepare a composite solution.
  • the concentration was adjusted to 2.0 wt%, and the organic solar cell had a structure of ITO / PEDOT: PSS / photoactive layer / Al.
  • ITO-coated glass substrates were ultrasonically cleaned with distilled water, acetone and 2-propanol, ozonated the ITO surface for 10 minutes, and spin-coated PEDOT: PSS (baytrom P) to 45 nm to 10 at 120 ° C. Heat treated for minutes.
  • the compound-PCBM composite solution was filtered through a 0.45 ⁇ m PP syringe filter, followed by spin coating to form Al in a thickness of 200 nm using a thermal evaporator under 3 ⁇ 10 ⁇ 8 torr vacuum.
  • the deposition produced an organic solar cell.
  • An organic solar cell was manufactured by the same method as Example 1 except that Chemical Formula 2 was used instead of Chemical Formula 1-1-1.
  • Voc is the open voltage
  • Jsc is the short-circuit current
  • FF is the fill factor
  • PCE is the energy conversion efficiency.
  • the open-circuit and short-circuit currents are the X- and Y-axis intercepts in the four quadrants of the voltage-current density curve, respectively. The higher these two values, the higher the efficiency of the solar cell.
  • 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. By dividing these three values by the intensity of the emitted light, the energy conversion efficiency can be obtained, and higher values are preferable.
  • 16 is a diagram illustrating current densities according to voltages of organic solar cells using Chemical Formulas 1-1-1 and Chemical Formula 2;
  • the compound containing a condensed ring derivative according to an exemplary embodiment of the present specification has the characteristics of high voltage and current. This can be interpreted as having a low band gap and high HOMO energy level by efficiently concentrating electrons due to the [Push] of the condensed ring derivative and the structural characteristics of Ar1 and Ar2.
  • Table 3 shows the results of calculating the compound of Chemical Formula 1-1-5 and the compound of Chemical Formula 3 by the calculation chemistry program.
  • TD-DFT calculation was performed using Gaussian 09 program, and B3PW91 functional and 6-31G * basis set were used.
  • the condensed ring derivative when a red shift occurs in the absorption spectrum, the long wavelength may be absorbed.
  • the molecular extinction coefficient (Molar extinction coefficient) is large, the band gap is reduced to absorb a large amount of light, it can have a positive effect on the efficiency of the device.

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Abstract

La présente invention concerne un dérivé à cycles fusionnés et une cellule solaire organique le comprenant.
PCT/KR2015/005678 2014-06-11 2015-06-05 Dérivé à cycles fusionnés et cellule solaire organique le comprenant WO2015190762A2 (fr)

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WO2017191466A1 (fr) * 2016-05-06 2017-11-09 Imperial Innovations Limited Mélanges ternaires organiques
WO2021230035A1 (fr) * 2020-05-11 2021-11-18 国立大学法人大阪大学 Composé naphtobisthiadiazole, son procédé de production, matériau semi-conducteur organique et dispositif semi-conducteur organique utilisant ledit composé

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WO2018236101A1 (fr) 2017-06-23 2018-12-27 주식회사 엘지화학 Cellule solaire organique
KR102250385B1 (ko) * 2017-10-18 2021-05-11 주식회사 엘지화학 유기 광 다이오드 및 이를 포함하는 유기 이미지 센서
CN109836437A (zh) * 2019-03-29 2019-06-04 南昌航空大学 一种a-d-a型苯并噻二唑小分子及其制备方法和应用
CN112159418B (zh) * 2020-09-11 2024-04-05 中国科学院宁波材料技术与工程研究所 共轭有机分子及有机太阳能电池

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US5331183A (en) 1992-08-17 1994-07-19 The Regents Of The University Of California Conjugated polymer - acceptor heterojunctions; diodes, photodiodes, and photovoltaic cells
US9184315B2 (en) * 2011-03-08 2015-11-10 Nankai University Photoelectric materials and preparation thereof
WO2014026244A1 (fr) * 2012-08-17 2014-02-20 Commonwealth Scientific And Industrial Research Organisation Dispositifs optoélectroniques photoactifs et à transistors
CN103788111B (zh) * 2012-10-26 2015-08-19 中国科学院化学研究所 一种可溶液加工两维共轭有机分子光伏材料及其制备方法与应用
CN103087083A (zh) * 2013-01-17 2013-05-08 中国科学院宁波材料技术与工程研究所 一种吡咯并吡咯二酮衍生物及其制备方法和应用

Cited By (3)

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WO2017191466A1 (fr) * 2016-05-06 2017-11-09 Imperial Innovations Limited Mélanges ternaires organiques
WO2017191468A1 (fr) * 2016-05-06 2017-11-09 Imperial Innovations Limited Accepteurs d'électrons sans fullerène
WO2021230035A1 (fr) * 2020-05-11 2021-11-18 国立大学法人大阪大学 Composé naphtobisthiadiazole, son procédé de production, matériau semi-conducteur organique et dispositif semi-conducteur organique utilisant ledit composé

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