WO2015190762A2 - Fused ring derivative and organic solar cell including same - Google Patents
Fused ring derivative and organic solar cell including same Download PDFInfo
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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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- 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
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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
- C07F7/0803—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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- 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
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- 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
The present description relates to a fused ring derivative and an organic solar cell including same.
Description
본 명세서는 2014년 6월 11일에 한국특허청에 제출된 한국 특허 출원 제 10-2014-0070698 호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This specification claims the benefit of the filing date of Korean Patent Application No. 10-2014-0070698 filed with the Korea Intellectual Property Office on June 11, 2014, the entire contents of which are incorporated herein.
본 명세서는 축합고리 유도체 및 이를 포함하는 유기 태양 전지에 관한 것이다.The present specification relates to a condensed ring derivative and an organic solar cell including the same.
유기 태양전지는 광기전력효과(photovoltaic effect)를 응용함으로써 태양에너지를 직접 전기에너지로 변환할 수 있는 소자이다. 태양전지는 박막을 구성하는 물질에 따라 무기 태양전지와 유기 태양전지로 나뉠 수 있다. 전형적인 태양전지는 무기 반도체인 결정성 실리콘(Si)을 도핑(doping)하여 p-n 접합으로 만든 것이다. 빛을 흡수하여 생기는 전자와 정공은 p-n 접합점까지 확산되고 그 전계에 의하여 가속되어 전극으로 이동한다. 이 과정의 전력변환 효율은 외부 회로에 주어지는 전력과 태양전지에 들어간 태양전력의 비로 정의되며, 현재 표준화된 가상 태양 조사 조건으로 측정 시 24%정도까지 달성되었다. 그러나 종래 무기 태양전지는 이미 경제성과 재료상의 수급에서 한계를 보이고 있기 때문에, 가공이 쉬우며 저렴하고 다양한 기능성을 가지는 유기물 반도체 태양전지가 장기적인 대체 에너지원으로 각광받고 있다.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. However, since the conventional inorganic solar cell has already shown a limit in the economic and material supply and demand, organic semiconductor solar cell, which is easy to process, cheap and has various functions, has been spotlighted as a long-term alternative energy source.
태양전지는 태양 에너지로부터 가능한 많은 전기 에너지를 출력할 수 있도록 효율을 높이는 것이 중요하다. 이러한 태양전지의 효율을 높이기 위해서는 반도체 내부에서 가능한 많은 엑시톤을 생성하는 것도 중요하지만 생성된 전하를 손실됨 없이 외부로 끌어내는 것 또한 중요하다. 전하가 손실되는 원인 중의 하나가 생성된 전자 및 정공이 재결합(recombination)에 의해 소멸하는 것이다. 생성된 전자나 정공이 손실되지 않고 전극에 전달되기 위한 방법으로 다양한 방법이 제시되고 있으나, 대부분 추가 공정이 요구되고 이에 따라 제조 비용이 상승할 수 있다.It is important to increase efficiency so that solar cells can output as much electrical energy as possible from solar energy. It is important to generate as much excitons inside the semiconductor as possible to increase the efficiency of such solar cells, but it is also important to draw the generated charges to the outside without loss. One of the causes of the loss of charge is that the generated electrons and holes disappear by recombination. Various methods have been proposed as methods for transferring the generated electrons or holes to the electrodes without losing the electrons or holes, but most of the additional processes are required and manufacturing costs may increase accordingly.
[선행기술문헌][Preceding technical literature]
[특허문헌][Patent Documents]
US 5331183US 5331183
US 5454880US 5454880
본 명세서는 축합고리 유도체 및 이를 포함하는 유기 태양 전지를 제공하는 것을 목적으로 한다.An object of the present disclosure is to provide a condensed ring derivative and an organic solar cell including the same.
본 명세서는 하기 화학식 1로 표시되는 축합고리 유도체를 제공한다. The present specification provides a condensed ring derivative represented by Formula 1 below.
[화학식 1] [Formula 1]
화학식 1에 있어서, In Chemical Formula 1,
n1 및 n2는 각각 0 내지 3의 정수이고, n1 and n2 are each an integer of 0 to 3,
n1 및 n2가 각각 2 이상인 경우, 2 이상의 괄호 내의 구조는 서로 동일하거나 상이하며, when n1 and n2 are each 2 or more, the structures in the two or more parentheses are the same or different from each other,
[Push]는 전자 주개로서 작용하는 구조이고, [Push] is a structure that acts as an electron donor,
X1 내지 X4는 서로 동일하거나 상이하고, 각각 독립적으로 CRR', NR, O, SiRR', PR, S, GeRR', Se 또는 Te이며, 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 내지 Y4는 서로 동일하거나 상이하고, 각각 독립적으로 CR", N, SiR", P 또는 GeR"이고, Y1 to Y4 are the same as or different from each other, and each independently CR ″, N, SiR ″, P, or GeR ″,
R, R', R" 및 R1 내지 R8은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 이미드기; 아미드기; 히드록시기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이며, 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 unsubstituted aralkyl Amine groups; substituted or unsubstituted arylamine groups; substituted or unsubstituted heteroarylamine groups; substituted or unsubstituted aryl groups; or substituted or unsubstituted heterocyclic groups,
Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 하기 구조 중 어느 하나이고, Ar1 and Ar2 are the same as or different from each other, and each independently one of the following structures,
상기 구조에 있어서, In the above structure,
a는 1 내지 7의 정수이고, a is an integer from 1 to 7,
b 및 c는 각각 1 내지 4의 정수이며, b and c are each an integer of 1 to 4,
a가 2 이상인 경우, 2 이상의 R15는 서로 동일하거나 상이하고, when a is 2 or more, two or more R15 are the same as or different from each other,
b가 2 이상인 경우, 2 이상의 R16은 서로 동일하거나 상이하며, when b is 2 or more, two or more R16 are the same as or different from each other,
c가 2 이상인 경우, 2 이상의 R17은 서로 동일하거나 상이하며, when c is 2 or more, two or more R17 are the same or different from each other,
R13 내지 R23은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 이미드기; 아미드기; 히드록시기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다. 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; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
또한, 본 명세서는 1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비되고, 광활성층을 포함하는 1층 이상의 유기물층을 포함하고, 상기 유기물층 중 1층 이상은 전술한 축합고리 유도체를 포함하는 것인 유기 태양 전지를 제공한다.In addition, 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.
본 명세서의 일 실시상태에 따른 축합고리 유도체는 전자 주개 성질을 갖는 [Push]와 상대적으로 전자 받개 성질을 갖는 Ar1 및 Ar2를 도입하여, HOMO 준위 값을 낮출 수 있다. 이를 도입하는 경우에 높은 구동 전압을 기대할 수 있다. 또한, 본 명세서의 일 실시상태에 따른 화합물은 흡수 스펙트럼에서 적색 편이(red shift)가 일어나, 낮은 LUMO 에너지 준위 값을 갖게 되고, 밴드갭이 감소하여 넓은 영역의 빛을 흡수할 수 있어, 소자의 효율이 긍정적인 영향을 줄 수 있다. 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. In addition, 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.
또한, [Push]와 X3를 포함하는 축합고리 및 X4를 포함하는 축합고리를 직접적으로 연결하여, 더욱 효과적인 전자 전달을 유도할 수 있다. In addition, a condensed ring including [Push] and X3 and a condensed ring including X4 may be directly connected to induce more effective electron transfer.
또한, 본 명세서의 일 실시상태에 따른 축합고리 유도체는 결정성이 우수하여, 필팩터(FF)의 상승을 기대할 수 있다. In addition, 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).
따라서, 상기 축합고리 유도체는 유기 태양 전지의 유기물층 재료로 사용될 수 있으며, 이를 포함하는 유기 태양 전지는 개방 전압과 단락 전류의 상승 및/또는 효율 증가 등에서 우수한 특성을 나타낼 수 있다. Therefore, 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.
본 명세서의 일 실시상태에 따른 축합고리 유도체는 유기 태양 전지에서 단독 또는 다른 물질과 혼합하여 사용이 가능하고, 효율의 향상, 축합고리 유도체의 열적 안정성 등의 특성에 의한 소자의 수명 향상 등이 기대될 수 있다.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.
도 1은 본 명세서의 일 실시상태에 따른 유기 태양 전지를 나타낸 도이다.1 illustrates an organic solar cell according to an exemplary embodiment of the present specification.
도 2는 화합물 A-1의 MS 스펙트럼을 나타낸 도이다. 2 is a diagram showing an MS spectrum of Compound A-1.
도 3은 화합물 A-1의 NMR 스펙트럼을 나타낸 도이다. 3 is a diagram showing an NMR spectrum of Compound A-1.
도 4는 화합물 A-2의 MS 스펙트럼을 나타낸 도이다. 4 is a diagram showing an MS spectrum of Compound A-2.
도 5는 화합물 A-2의 NMR 스펙트럼을 나타낸 도이다. 5 is a diagram showing an NMR spectrum of Compound A-2.
도 6은 화합물 A-3의 MS 스펙트럼을 나타낸 도이다. 6 is a diagram showing an MS spectrum of Compound A-3.
도 7은 화합물 A-3의 NMR 스펙트럼을 나타낸 도이다. 7 is a diagram showing an NMR spectrum of Compound A-3.
도 8은 화학식 1-1-1의 MS 스펙트럼을 나타낸 도이다. 8 is a diagram showing an MS spectrum of Chemical Formula 1-1-1.
도 9는 화학식 1-1-1의 NMR 스펙트럼을 나타낸 도이다. 9 is a diagram showing an NMR spectrum of Chemical Formula 1-1-1.
도 10은 화학식 2의 MS 스펙트럼을 나타낸 도이다. 10 is a diagram showing an MS spectrum of Chemical Formula 2.
도 11은 화학식 2의 NMR 스펙트럼을 나타낸 도이다. 11 is a diagram showing an NMR spectrum of Chemical Formula 2.
도 12는 화학식 1-1-1과 화학식 2를 클로로벤젠 용액 내에서 UV스펙트럼을 비교한 도이다. 12 is a diagram comparing UV spectra of Chemical Formulas 1-1-1 and Chemical Formula 2 in a chlorobenzene solution.
도 13은 화학식 1-1-1과 화학식 2를 필름상태에서 UV 스펙트럼을 비교한 도이다. FIG. 13 is a view comparing UV spectra of Chemical Formulas 1-1-1 and Chemical Formula 2 in a film state. FIG.
도 14는 화학식 1-1-1의 전기화학 측정 결과(cyclic voltametry)를 나타낸 도이다.14 is a view illustrating an electrochemical measurement result (cyclic voltametry) of Chemical Formula 1-1-1.
도 15는 화학식 2의 전기화학 측정 결과(cyclic voltametry)를 나타낸 도이다.FIG. 15 is a diagram illustrating an electrochemical measurement result (cyclic voltametry) of Chemical Formula 2. FIG.
도 16은 화학식 1-1-1과 화학식 2를 이용한 유기 태양 전지의 전압에 따른 전류 밀도를 나타낸 도이다. 16 is a diagram illustrating current densities according to voltages of organic solar cells using Chemical Formulas 1-1-1 and Chemical Formula 2;
도 17은 실험예 2와 비교예 2의 UV 스펙트럼의 경향을 분석한 도이다.17 is a diagram analyzing the trend of the UV spectrum of Experimental Example 2 and Comparative Example 2.
[부호의 설명][Description of the code]
101: 기판101: substrate
102: 제1 전극102: first electrode
103: 정공수송층103: hole transport layer
104: 광활성층104: photoactive layer
105: 제2 전극105: second electrode
이하 본 명세서에 대하여 상세히 설명한다. Hereinafter, the present specification will be described in detail.
본 명세서는 상기 화학식 1로 표시되는 축합고리 유도체를 제공한다. The present specification provides a condensed ring derivative represented by Chemical Formula 1.
본 명세서에 있어서, 
는 다른 치환기에 연결되는 부위를 의미한다.In the present specification, Means a site linked to another substituent.
본 명세서의 일 실시상태에 있어서, 상기 [Push] 축합고리 유도체 내에서 전자 주개로서 작용한다. In one embodiment of the present specification, it acts as an electron donor in the [Push] condensed ring derivative.
하나의 실시상태에 있어서, 상기 [Push]의 HOMO(highest occupied molecular orbital) 에너지 준위는 5.0 eV 내지 6.0 eV이다. In one embodiment, the highest occupied molecular orbital (HOMO) energy level of [Push] is 5.0 eV to 6.0 eV.
하나의 실시상태에 있어서, 상기 [Push]의 밴드갭은 2 eV 내지 4.5 eV이다. In one embodiment, the band gap of the [Push] is 2 eV to 4.5 eV.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2는 축합고리 유도체 내에서 전자 받개로서 작용한다. 전자 받개로서의 Ar1 및 Ar2로 인하여, 축합고리 유도체의 밴드갭을 감소시킬 수 있으며, 축합고리 유도체의 말단에 다이폴(dipole)이 형성되므로 전자를 효율적으로 집중시킬 수 있다. 따라서, 본 명세서의 일 실시상태에 따른 축합고리 유도체의 말단에 전자가 집중되므로, 소자의 유기물층에 도입하는 경우에 축합고리 유도체의 말단과 소자 내의 전자 받개 물질과의 접촉을 유발할 수 있으며, 전자 받개 물질로의 전자 전달이 용이한 효과가 있다. In one embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따른 축합고리 유도체는 상대적으로 [Push]는 상대적으로 전자 주개로서 작용하고, Ar1 및 Ar2는 전자 받개로서 작용한다. 이 경우에 LUMO (lowest unoccupied molecular orbital) 상태의 전자는 상대적으로 Ar1 및 Ar2에 집중(localization) 된다. 이로 인하여, [Push] 와 Ar1 또는 Ar2 사이에 분극이 존재한다. Condensed ring derivatives according to one embodiment of the present specification 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.
본 명세서는 상기 [Push]와 Ar1 또는 Ar2 사이에 상대적으로 평면성이 우수하고, 공액 구조(conjugation)를 갖는 링커를 도입하여, 전자들이 축합고리 유도체 내에서 빠르게 Ar1 또는 Ar2 방향으로 이동시켜, 전자의 집중을 극대화시킬 수 있다. 이 경우, 형성된 엑시톤이 분자내에서 빠르게 이동할 수 있으며, 엑시톤의 분극을 극대화 할 수 있어, 낮은 밴드갭의 특성을 가질 수 있다. 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. In this case, the formed excitons can be quickly moved in the molecule, and the polarization of the excitons can be maximized, thereby having low bandgap characteristics.
또한, 본 명세서의 일 실시상태에 따른 축합고리 유도체는 [Push] 구조와 X3를 포함하는 고리 및 X4를 포함하는 고리가 직접 연결된다. 상기와 같이, [Push]구조와 X3을 포함하는 고리 또는 X4를 포함하는 고리가 직접 결합하는 경우는 [Push]구조와 X3를 포함하는 고리 또는 X4를 포함하는 고리 사이에 다른 스페이서나 링커를 포함하는 경우보다 적색 편이한 것을 관찰할 수 있다. In addition, 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. 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.
또한, [Push]구조와 X3를 포함하는 고리 또는 X4를 포함하는 고리 사이에 다른 스페이서나 링커를 포함하는 경우엔 낮은 용해도로 소자의 제조 면에서 비효율 적이다. In addition, when other spacers or linkers are included between the [Push] structure and the ring containing X3 or the ring containing X4, low solubility is inefficient in terms of device fabrication.
본 명세서에 있어서, 에너지 준위는 에너지의 크기를 의미하는 것이다. 따라서, 진공준위로부터 마이너스(-) 방향으로 에너지 준위가 표시되는 경우에도, 에너지 준위는 해당 에너지 값의 절대값을 의미하는 것으로 해석된다. 예컨대, HOMO 에너지 준위란 진공준위로부터 최고 점유 분자 오비탈(highest occupied molecular orbital)까지의 거리를 의미한다. 또한, LUMO 에너지 준위란 진공준위로부터 최저 비점유 분자 오비탈(lowest unoccupied molecular orbital)까지의 거리를 의미한다. In the present specification, 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. For example, the HOMO energy level means the distance from the vacuum level to the highest occupied molecular orbital. In addition, the LUMO energy level means the distance from the vacuum level to the lowest unoccupied molecular orbital.
또한, 본 명세서에서 전자 주개로서 작용하는 상기 [Push] 구조의 경우에는 전기 화학 측정 결과(Cyclic voltammetry)에서 산화 (oxidation)를 갖는 구조를 의미할 수 있다. 본 명세서에서 전자 받개로서 작용하는 Ar1 및 Ar2는 전기 화학 측정 결과(Cyclic voltammetry)에서 환원(reduction)를 갖는 구조를 의미할 수 있다. 다만, 전자 받개 및 전자 주개로서 작용하는 구조는 산화 또는 환원 각각에 대해서만 관찰되는 것으로 한정하는 것은 아니다. In addition, in the case of the [Push] structure which acts as an electron donor in the present specification, it may mean a structure having oxidation in an electrochemical measurement result (Cyclic voltammetry). In the present specification, Ar1 and Ar2 serving as electron acceptors may refer to a structure having reduction in electrochemical measurement results (Cyclic voltammetry). However, the structures acting as electron acceptors and electron donors are not limited to those observed only for oxidation or reduction, respectively.
이 경우, 본 명세서의 일 실시상태에 따른 축합고리 유도체를 포함하는 유기 태양 전지를 비롯한 소자 내에서 높은 전류 및 높은 효율을 기대할 수 있다. In this case, high current and high efficiency can be expected in a device including an organic solar cell including a condensed ring derivative according to one embodiment of the present specification.
하나의 실시상태에 있어서, 상기 [Push]는 치환 또는 비치환된 아릴렌기; 및 치환 또는 비치환된 2가의 헤테로고리기로 이루어진 군에서 1 또는 2 이상을 포함한다. In one embodiment, 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.
본 명세서의 일 실시상태에 있어서, 상기 [Push]는 하기 구조 중 어느 하나이다. In one embodiment of the present specification, the [Push] is any one of the following structures.
상기 구조에 있어서, In the above structure,
d 및 d'는 각각 1 내지 3의 정수이고, d and d 'are each an integer of 1 to 3,
d가 2 이상인 경우, 2 이상의 R100은 서로 동일하거나 상이하며, when d is 2 or more, two or more R100 are the same as or different from each other,
d'가 2 이상인 경우, 2 이상의 R101은 서로 동일하거나 상이하고, when d 'is 2 or more, two or more R101 are the same as or different from each other,
X10 내지 X13은 서로 동일하거나 상이하고, 각각 독립적으로 CRaRb, NRa, O, SiRaRb, PRa, S, GeRaRb, Se 또는 Te이며, 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 및 Y11은 서로 동일하거나 상이하고, 각각 독립적으로 CRc, N, SiRc, P 또는 GeRc이고,Y10 and Y11 are the same as or different from each other, and each independently CRc, N, SiRc, P, or GeRc,
Ra, Rb, Rc 및 R100 내지 R103은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 이미드기; 아미드기; 히드록시기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다. 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 unsubstituted boron group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
또 하나의 실시상태에 있어서, 상기 [Push]는 
이다. In another embodiment, the [Push] is to be.
또 다른 실시상태에 있어서, 상기 [Push]는 
이다.In another embodiment, the [Push] is to be.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 축합고리 유도체는 하기 화학식 1-1 또는 화학식 1-2로 표시된다. In one embodiment of the present specification, the condensed ring derivative represented by Formula 1 is represented by the following Formula 1-1 or Formula 1-2.
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
화학식 1-1 및 1-2에 있어서, In Chemical Formulas 1-1 and 1-2,
n1 및 n2, X1 내지 X4, Y1 내지 Y4, R1 내지 R8, Ar1 및 Ar2는 화학식 1에서 정의한 바와 동일하고, n1 and n2, X1 to X4, Y1 to Y4, R1 to R8, Ar1 and Ar2 are the same as defined in Formula 1,
X10 내지 X13은 서로 동일하거나 상이하고, 각각 독립적으로 CRaRb, NRa, O, SiRaRb, PRa, S, GeRaRb, Se 또는 Te이며, 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 및 Y11은 서로 동일하거나 상이하고, 각각 독립적으로 CRc, N, SiRc, P 또는 GeRc이고,Y10 and Y11 are the same as or different from each other, and each independently CRc, N, SiRc, P, or GeRc,
Ra, Rb, Rc 및 R100 내지 R103은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 이미드기; 아미드기; 히드록시기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다. 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 unsubstituted boron group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
상기 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다.Examples of the substituents are described below, but are not limited thereto.
상기 "치환"이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치 즉, 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 동일하거나 상이할 수 있다.The term "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.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 알킬기; 알케닐기; 알콕시기; 에스터기; 카보닐기; 카복실기; 히드록시기; 시클로알킬기; 실릴기; 아릴알케닐기; 아릴옥시기; 알킬티옥시기; 알킬술폭시기; 아릴술폭시기; 붕소기; 알킬아민기; 아랄킬아민기; 아릴아민기; 헤테로고리기; 아릴아민기; 아릴기; 니트릴기; 니트로기; 히드록시기; 및 헤테로 고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되었거나 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 비페닐기일 수 있다. 즉, 비페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다.As used herein, the term "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. For example, "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.
상기 치환기들은 추가의 치환기로 치환 또는 비치환될 수 있다.The substituents may be substituted or unsubstituted with additional substituents.
본 명세서에 있어서, 할로겐기는 불소, 염소, 브롬 또는 요오드가 될 수 있다.In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In this specification, although 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.
본 명세서에 있어서, 아미드기는 아미드기의 질소가 수소, 탄소수 1 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로 1 또는 2 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, 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.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 50인 것이 바람직하다. 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 시클로펜틸메틸, 시클로헥실메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이들에 한정되지 않는다.In the present specification, 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-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 구체적으로 시클로프로필, 시클로부틸, 시클로펜틸, 3-메틸시클로펜틸, 2,3-디메틸시클로펜틸, 시클로헥실, 3-메틸시클로헥실, 4-메틸시클로헥실, 2,3-디메틸시클로헥실, 3,4,5-트리메틸시클로헥실, 4-tert-부틸시클로헥실, 시클로헵틸, 시클로옥틸 등이 있으나, 이에 한정되지 않는다. In the present specification, 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.
본 명세서에 있어서, 상기 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 20인 것이 바람직하다. 구체적으로, 메톡시, 에톡시, n-프로폭시, 이소프로폭시, i-프로필옥시, n-부톡시, 이소부톡시, tert-부톡시, sec-부톡시, n-펜틸옥시, 네오펜틸옥시, 이소펜틸옥시, n-헥실옥시, 3,3-디메틸부틸옥시, 2-에틸부틸옥시, n-옥틸옥시, n-노닐옥시, n-데실옥시, 벤질옥시, p-메틸벤질옥시 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, 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.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다.In the present specification, 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.
본 명세서에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, specifically, the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. However, the present invention is not limited thereto.
본 명세서에 있어서, 아릴기는 단환식 아릴기 또는 다환식 아릴기일 수 있으며, 탄소수 1 내지 25의 알킬기 또는 탄소수 1 내지 25의 알콕시기 등의 치환기가 치환되는 경우를 포함한다. 또한, 본 명세서 내에서의 아릴기는 방향족고리를 의미할 수 있다.In the present specification, 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. In addition, the aryl group in the present specification may mean an aromatic ring.
상기 아릴기가 단환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나, 탄소수 6 내지 25인 것이 바람직하다. 구체적으로 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. When the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but preferably 6 to 25 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
상기 아릴기가 다환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나. 탄소수 10 내지 24인 것이 바람직하다. 구체적으로 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-24. Specifically, 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.
본 명세서에 있어서, 상기 플루오레닐기는 치환될 수 있으며, 인접한 치환기들이 서로 결합하여 고리를 형성할 수 있다. In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
상기 플루오레닐기가 치환되는 경우, 
등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted, And so on. However, the present invention is not limited thereto.
본 명세서에 있어서, 헤테로 고리기는 탄소 원자 대신 1 이상의 이종 원소를 포함하는 구조로서, 예컨대, O, N, Se, Ge, Si 및 S 등을 포함하는 고리 구조로서, 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로 고리기의 예로는 싸이오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 트리아졸기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조싸이오펜기, 디벤조싸이오펜기, 벤조퓨라닐기, 페난쓰롤린기(phenanthroline), 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 벤조티아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, 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. Examples of 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, phenanthroline group (phenanthroline), thiazolyl group, Isooxazolyl group, oxdiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, dibenzofuranyl group and the like, but is not limited thereto.
상기 헤테로 고리기는 단환 또는 다환일 수 있으며, 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있다.The heterocyclic group may be monocyclic or polycyclic, and may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic.
본 명세서에 있어서, 아릴아민기의 예로는 치환 또는 비치환된 모노아릴아민기, 치환 또는 비치환된 디아릴아민기, 또는 치환 또는 비치환된 트리아릴아민기가 있다. 상기 아릴아민기 중의 아릴기는 단환식 아릴기일 수 있고, 다환식 아릴기일 수 있다. 상기 아릴기가 2 이상을 포함하는 아릴아민기는 단환식 아릴기, 다환식 아릴기, 또는 단환식아릴기와 다환식 아릴기를 동시에 포함할 수 있다. In the present specification, 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.
아릴 아민기의 구체적인 예로는 페닐아민, 나프틸아민, 비페닐아민, 안트라세닐아민, 3-메틸-페닐아민, 4-메틸-나프틸아민, 2-메틸-비페닐아민, 9-메틸-안트라세닐아민, 디페닐 아민기, 페닐 나프틸 아민기, 디톨릴 아민기, 페닐 톨릴 아민기, 카바졸 및 트리페닐 아민기 등이 있으나, 이에 한정되는 것은 아니다. Specific examples of the aryl amine group 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.
본 명세서에 있어서, 헤테로아릴아민기 중의 헤테로 아릴기는 전술한 헤테로고리기의 예시 중에서 선택될 수 있다.In the present specification, the heteroaryl group in the heteroarylamine group may be selected from the examples of the heterocyclic group described above.
본 명세서에 있어서, 아릴옥시기, 아릴티옥시기, 아릴술폭시기 및 아랄킬아민기 중의 아릴기는 전술한 아릴기의 예시와 같다. 구체적으로 아릴옥시기로는 페녹시, p-토릴옥시, m-토릴옥시, 3,5-디메틸-페녹시, 2,4,6-트리메틸페녹시, p-tert-부틸페녹시, 3-비페닐옥시, 4-비페닐옥시, 1-나프틸옥시, 2-나프틸옥시, 4-메틸-1-나프틸옥시, 5-메틸-2-나프틸옥시, 1-안트릴옥시, 2-안트릴옥시, 9-안트릴옥시, 1-페난트릴옥시, 3-페난트릴옥시, 9-페난트릴옥시 등이 있고, 아릴티옥시기로는 페닐티옥시기, 2－메틸페닐티옥시기, 4－tert－부틸페닐티옥시기 등이 있으며, 아릴술폭시기로는 벤젠술폭시기, p－톨루엔술폭시기 등이 있으나, 이에 한정되지 않는다.In the present specification, the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group and aralkylamine group is the same as the aryl group described above. Specifically, as 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. Examples of the arylthioxy group 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.
본 명세서에 있어서, 알킬티옥시기, 알킬술폭시기 중의 알킬기는 전술한 알킬기의 예시와 같다. 구체적으로 알킬티옥시기로는 메틸티옥시기, 에틸티옥시기, tert－부틸티옥시기, 헥실티옥시기, 옥틸티옥시기 등이 있고, 알킬술폭시기로는 메실, 에틸술폭시기, 프로필술폭시기, 부틸술폭시기 등이 있으나, 이에 한정되지 않는다.In this specification, 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. Specifically, 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, and the alkyl sulfoxy group includes mesyl, ethyl sulfoxy, propyl sulfoxy and butyl sulfoxy groups. Etc., but is not limited thereto.
본 명세서의 일 실시상태에 있어서, 상기 X1 내지 X4는 S이고, In one embodiment of the present specification, X1 to X4 are S,
Y1 내지 Y4는 N이며, Y1 to Y4 are N,
Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 
; 
; 또는 
이고, 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 내지 R8은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 할로겐기; 또는 치환 또는 비치환된 알콕시기이며, 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 및 R23은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 또는 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이고,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]는 S 원자를 1 이상 포함하는 헤테로고리기이며, 상기 헤테로고리기는 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기로 치환 또는 비치환된다. [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.
본 명세서의 일 실시상태에 있어서, R5 내지 R8은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 할로겐기; 또는 치환 또는 비치환된 알콕시기이다. In one embodiment of the present specification, 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.
본 명세서의 또 하나의 실시상태에 있어서, 상기 R5 내지 R8 중 적어도 하나는 할로겐기; 또는 치환 또는 비치환된 알콕시기이다.In another exemplary embodiment of the present specification, at least one of R5 to R8 is a halogen group; Or a substituted or unsubstituted alkoxy group.
본 명세서의 또 하나의 실시상태에 있어서, 상기 R5 내지 R8 중 적어도 하나는 할로겐기; 또는 탄소수 1 내지 30의 치환 또는 비치환된 알콕시기이다.In another exemplary embodiment of the present specification, at least one of R5 to R8 is a halogen group; Or a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms.
이 경우, 상기 축합고리 유도체 중 [Push] 구조와 X3를 포함하는 고리 또는 X4를 포함하는 고리 사이의 비결합 상호반응(non-bonding interaction)으로 인하여 평면성(planarity)가 향상되어 결정성이 우수하다. 이 경우, 전류의 특성의 향상을 기대할 수 있다. In this case, the 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. . In this case, an improvement in the characteristics of the current can be expected.
또한, 상기 화합물 내에서 전자 주개로서 작용하는 [Push]의 구조와 전자 받개로서 작용하는 Ar1 및 Ar2 사이의 평면성의 향상으로 형성된 엑시톤(exciton)이 분자 내에서 안정적으로 빠르게 집중(localization)이 될 수 있다. 따라서, 엑시톤의 분극을 극대화 할 수 있으며, 낮은 밴드갭의 특성을 가질 수 있다. In addition, 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.
따라서, 본 명세서의 일 실시상태에 따라, [Push]구조와 X3을 포함하는 고리 또는 X4를 포함하는 고리가 직접 결합하는 경우에는 소자의 효율 및 공정상에 유리하다. Therefore, according to an exemplary embodiment of the present specification, when the [Push] structure and the ring including X3 or the ring including X4 are directly bonded, it is advantageous in terms of efficiency and process of the device.
본 명세서의 일 실시상태에 있어서, 상기 R5는 수소이다. In one embodiment of the present specification, R5 is hydrogen.
본 명세서의 일 실시상태에 있어서, R5 는 치환 또는 비치환된 알콕시기이다.In one embodiment of the present specification, R5 is a substituted or unsubstituted alkoxy group.
또 하나의 실시상태에 있어서, 상기 R5 는 치환 또는 비치환된 탄소수 1 내지 20의 알콕시기이다. In another exemplary embodiment, R5 is a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
또 하나의 실시상태에 있어서, 상기 R5 는 치환 또는 비치환된 옥톡시기이다. In another exemplary embodiment, R5 is a substituted or unsubstituted octoxy group.
또 다른 실시상태에 있어서, R5는 옥톡시기이다. In another embodiment, R5 is an octoxy group.
하나의 실시상태에 있어서, 상기 R6은 할로겐기이다. In one embodiment, R6 is a halogen group.
또 하나의 실시상태에 있어서, 상기 R6은 불소이다. In another exemplary embodiment, R6 is fluorine.
본 명세서의 일 실시상태에 있어서, R6은 치환 또는 비치환된 알콕시기이다.In one embodiment of the present specification, R6 is a substituted or unsubstituted alkoxy group.
또 하나의 실시상태에 있어서, 상기 R6은 치환 또는 비치환된 탄소수 1 내지 20의 알콕시기이다. In another exemplary embodiment, R6 is a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
또 하나의 실시상태에 있어서, 상기 R6은 치환 또는 비치환된 옥톡시기이다. In another exemplary embodiment, R6 is a substituted or unsubstituted octoxy group.
또 다른 실시상태에 있어서, R6은 옥톡시기이다. In another embodiment, R6 is an octoxy group.
본 명세서의 일 실시상태에 있어서, 상기 R7은 할로겐기이다. In one embodiment of the present specification, R7 is a halogen group.
또 하나의 실시상태에 있어서, 상기 R7은 불소이다. In another exemplary embodiment, R7 is fluorine.
본 명세서의 일 실시상태에 있어서, R7은 치환 또는 비치환된 알콕시기이다.In one embodiment of the present specification, R7 is a substituted or unsubstituted alkoxy group.
또 하나의 실시상태에 있어서, 상기 R7은 치환 또는 비치환된 탄소수 1 내지 20의 알콕시기이다. In another exemplary embodiment, R7 is a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
또 하나의 실시상태에 있어서, 상기 R7은 치환 또는 비치환된 옥톡시기이다. In another exemplary embodiment, R7 is a substituted or unsubstituted octoxy group.
또 다른 실시상태에 있어서, R7은 옥톡시기이다. In another embodiment, R7 is an octoxy group.
본 명세서의 일 실시상태에 있어서, 상기 R8는 수소이다.In one embodiment of the present specification, R8 is hydrogen.
본 명세서의 일 실시상태에 있어서, R8은 치환 또는 비치환된 알콕시기이다.In one embodiment of the present specification, R8 is a substituted or unsubstituted alkoxy group.
또 하나의 실시상태에 있어서, 상기 R8은 치환 또는 비치환된 탄소수 1 내지 20의 알콕시기이다. In another exemplary embodiment, R8 is a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
또 하나의 실시상태에 있어서, 상기 R8은 치환 또는 비치환된 옥톡시기이다. In another exemplary embodiment, R8 is a substituted or unsubstituted octoxy group.
또 다른 실시상태에 있어서, R8은 옥톡시기이다. In another embodiment, R8 is an octoxy group.
본 명세서의 일 실시상태에 있어서, 상기 X1은 S이다. In one embodiment of the present specification, X1 is S.
또 하나의 실시상태에 있어서, X2는 S이다. In another embodiment, X2 is S.
본 명세서의 일 실시상태에 있어서, 상기 X3는 S이다. In one embodiment of the present specification, X3 is S.
또 하나의 실시상태에 있어서, 상기 X4는 S이다.In another exemplary embodiment, X4 is S.
본 명세서의 일 실시상태에 있어서, n1은 2이다. In one embodiment of the present specification, n1 is 2.
본 명세서의 일 실시상태에 있어서, 상기 n1은 1이다. In one embodiment of the present specification, n1 is 1.
또 다른 실시상태에 있어서, n2는 2이다. In another embodiment, n2 is two.
또 하나의 실시상태에 있어서, 상기 n2는 1이다. In another exemplary embodiment, n2 is one.
또 하나의 일 실시상태에 있어서, 상기 R1은 수소이다. In another exemplary embodiment, R1 is hydrogen.
또 하나의 실시상태에 있어서, 상기 R2는 수소이다. In another exemplary embodiment, R2 is hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 R3는 수소이다. In one embodiment of the present specification, R3 is hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 R4는 수소이다. In one embodiment of the present specification, R4 is hydrogen.
본 명세서의 일 실시상태에 있어서, Y1은 N이다. In one embodiment of the present specification, Y1 is N.
본 명세서의 다른 실시상태에 있어서, Y2는 N이다. In another embodiment of the present specification, Y2 is N.
또 하나의 실시상태에 있어서, Y3는 N이다. In another embodiment, Y3 is N.
본 명세서의 일 실시상태에 있어서, Y4는 N이다.In one embodiment of the present specification, Y4 is N.
본 명세서의 일 실시상태에 있어서, Ar1은 
이다.In one embodiment of the present specification, Ar1 is to be.
또 다른 실시상태에 있어서, Ar1은 
이다. In another embodiment, Ar1 is to be.
또 하나의 실시상태에 있어서, 상기 Ar1은 
이다.In another embodiment, Ar1 is to be.
본 명세서의 일 실시상태에 있어서, Ar2는 
이다. In one embodiment of the present specification, Ar2 is to be.
또 다른 실시상태에 있어서, Ar2는 
이다. In another embodiment, Ar2 is to be.
또 하나의 실시상태에 있어서, 상기 Ar2는 
이다.In another embodiment, Ar2 is to be.
본 명세서의 일 실시상태에 있어서, [Push]는 S 원자를 1 이상 포함하는 헤테로고리기이다. In one embodiment of the present specification, [Push] is a heterocyclic group containing one or more S atoms.
본 명세서의 일 실시상태에 있어서, R100은 수소이다. In one embodiment of the present specification, R100 is hydrogen.
하나의 실시상태에 있어서, R101은 수소이다. In one embodiment, R101 is hydrogen.
또 하나의 실시상태에 있어서, R102는 수소이다. In another embodiment, R102 is hydrogen.
다른 실시상태에 있어서, R103은 수소이다. In other embodiments, R103 is hydrogen.
본 명세서의 일 실시상태에 있어서, X10은 S이다. In one embodiment of the present specification, X10 is S.
또 하나의 실시상태에 있어서, X11은 SiRaRb이다. In another embodiment, X11 is SiRaRb.
또 다른 실시상태에 있어서, X11은 S이다. In another embodiment, X11 is S.
하나의 실시상태에 있어서, X12는 SiRaRb이다. In one embodiment, X12 is SiRaRb.
또 하나의 실시상태에 있어서, X13은 S이다. In another embodiment, X13 is S.
본 명세서의 일 실시상태에 있어서, Y10은 CRc이다. In one embodiment of the present specification, Y10 is CRc.
또 다른 실시상태에 있어서, 상기 Y11은 CRc이다.In another embodiment, Y11 is CRc.
본 명세서의 일 실시상태에 있어서, 상기 Ra, Rb 및 Rc는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다. In one embodiment of the present specification, 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.
또 하나의 실시상태에 있어서, 상기 Ra, Rb 및 Rc는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 헤테로고리기이다. In another embodiment, 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.
하나의 실시상태에 있어서, Ra 및 Rb는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기이다. In one embodiment, Ra and Rb are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group.
하나의 실시상태에 있어서, Ra 및 Rb는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 30의 알킬기이다. In one embodiment, 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.
본 명세서의 일 실시상태에 있어서, Ra는 치환 또는 비치환된 알킬기이다. In one embodiment of the present specification, Ra is a substituted or unsubstituted alkyl group.
본 명세서의 일 실시상태에 있어서, Ra는 치환 또는 비치환된 탄소수 1 내지 30의 알킬기이다.In one embodiment of the present specification, Ra is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
하나의 실시상태에 있어서, Ra는 치환 또는 비치환된 옥틸기이다. In one embodiment, Ra is a substituted or unsubstituted octyl group.
또 하나의 실시상태에 있어서, Ra는 옥틸기이다.In another exemplary embodiment, Ra is an octyl group.
본 명세서의 일 실시상태에 있어서, Rb는 치환 또는 비치환된 알킬기이다. In one embodiment of the present specification, Rb is a substituted or unsubstituted alkyl group.
본 명세서의 일 실시상태에 있어서, Rb는 치환 또는 비치환된 탄소수 1 내지 30의 알킬기이다.In one embodiment of the present specification, Rb is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
하나의 실시상태에 있어서, Rb는 치환 또는 비치환된 옥틸기이다. In one embodiment, Rb is a substituted or unsubstituted octyl group.
또 하나의 실시상태에 있어서, Rb는 옥틸기이다. In another exemplary embodiment, Rb is an octyl group.
본 명세서의 일 실시상태에 있어서, 상기 Rc는 치환 또는 비치환된 헤테로고리기이다. In one embodiment of the present specification, Rc is a substituted or unsubstituted heteroring group.
본 명세서의 일 실시상태에 있어서, 상기 Rc는 치환 또는 비치환된 S 원자를 포함하는 헤테로고리기이다.In one embodiment of the present specification, Rc is a heterocyclic group including a substituted or unsubstituted S atom.
또 하나의 실시상태에 있어서, 상기 Rc는 알킬기로 치환 또는 비치환된 S 원자를 포함하는 헤테로고리기이다. In another exemplary embodiment, Rc is a heterocyclic group including an S atom unsubstituted or substituted with an alkyl group.
또 다른 실시상태에 있어서, 상기 Rc는 알킬기로 치환된 싸이오펜기이다.In another embodiment, Rc is a thiophene group substituted with an alkyl group.
본 명세서의 일 실시상태에 있어서, 상기 Rc는 2-에틸헥실기로 치환된 싸이오펜기이다.In one embodiment of the present specification, Rc is a thiophene group substituted with a 2-ethylhexyl group.
본 명세서의 하나의 실시상태에 있어서, R13, R14, R22 및 R23은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 또는 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이다.In one embodiment of the present specification, 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.
본 명세서의 일 실시상태에 있어서, R13은 수소이다. In one embodiment of the present specification, R13 is hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 R14는 치환 또는 비치환된 알킬기이다. In one embodiment of the present specification, R14 is a substituted or unsubstituted alkyl group.
본 명세서의 일 실시상태에 있어서, 상기 R14는 치환 또는 비치환된 탄소수 1 내지 30의 알킬기이다. In one embodiment of the present specification, R14 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
하나의 실시상태에 있어서, 상기 R14는 치환 또는 비치환된 옥틸기이다. In one embodiment, R14 is a substituted or unsubstituted octyl group.
하나의 실시상태에 있어서, 상기 R14는 치환 또는 비치환된 에틸기이다. In one embodiment, R14 is a substituted or unsubstituted ethyl group.
또 하나의 실시상태에 있어서, 상기 R14는 에틸기이다. In another exemplary embodiment, R14 is an ethyl group.
다른 실시상태에 있어서, 상기 R14는 옥틸기이다. In another embodiment, R14 is an octyl group.
본 명세서의 일 실시상태에 있어서, 상기 R22는 치환 또는 비치환된 알킬기이다. In one embodiment of the present specification, R22 is a substituted or unsubstituted alkyl group.
본 명세서의 일 실시상태에 있어서, 상기 R22는 치환 또는 비치환된 탄소수 1 내지 30의 알킬기이다. In one embodiment of the present specification, R22 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
하나의 실시상태에 있어서, 상기 R22는 치환 또는 비치환된 옥틸기이다. In one embodiment, R22 is a substituted or unsubstituted octyl group.
하나의 실시상태에 있어서, 상기 R22는 치환 또는 비치환된 에틸기이다. In one embodiment, R22 is a substituted or unsubstituted ethyl group.
또 하나의 실시상태에 있어서, 상기 R22는 에틸기이다. In another exemplary embodiment, R22 is an ethyl group.
본 명세서의 일 실시상태에 있어서, 상기 R23은 치환 또는 비치환된 알킬기이다. In one embodiment of the present specification, R23 is a substituted or unsubstituted alkyl group.
본 명세서의 일 실시상태에 있어서, 상기 R23은 치환 또는 비치환된 탄소수 1 내지 30의 알킬기이다. In one embodiment of the present specification, R23 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
하나의 실시상태에 있어서, 상기 R23은 치환 또는 비치환된 옥틸기이다. In one embodiment, R23 is a substituted or unsubstituted octyl group.
하나의 실시상태에 있어서, 상기 R23은 치환 또는 비치환된 에틸기이다. In one embodiment, R23 is a substituted or unsubstituted ethyl group.
또 하나의 실시상태에 있어서, 상기 R23은 에틸기이다. In another exemplary embodiment, R23 is an ethyl group.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 축합고리 유도체는 하기 화학식 1-1-1 내지 1-1-5 중 어느 하나로 표시된다. In one embodiment of the present specification, 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.
[화학식 1-1-1][Formula 1-1-1]
[화학식 1-1-2][Formula 1-1-2]
[화학식 1-1-3][Formula 1-1-3]
[화학식 1-1-4][Formula 1-1-4]
[화학식 1-1-5][Formula 1-1-5]
상기 축합고리 유도체는 후술하는 제조예를 기초로 제조될 수 있다. The condensed ring derivative may be prepared based on the preparation examples described below.
본 명세서의 일 실시상태에 따른 축합고리 유도체는 n1의 괄호 안의 구조의 일 말단에 할로겐기 다른 말단에는 디옥솔란기를 도입한 화합물과 양 말단에 할로겐기가 도입된 X3을 포함하는 화합물을 결합시켜, 일 말단에는 할로겐기 다른 말단에는 알데하이드기가 도입된 구조를 제조한다. 같은 방법으로 n2의 괄호 안의 구조 및 X4을 포함하는 구조를 제조한다. 상기 제조된 두 화합물과 [Push]를 결합시켜, 각각의 말단에 알데하이드기가 도입된 화합물을 제조한다. 그 후, Ar1 및 Ar2를 도입하여 화학식 1-1-1 내지 1-1-5 중 어느 하나로 표시되는 축합고리 유도체뿐만 아니라, 화학식 1로 표시되는 축합고리 유도체를 제조할 수 있다. 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 | transduced the halogen group in the terminal and the aldehyde group in the other terminal is produced. In the same manner, 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. Thereafter, 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.
본 명세서에 따른 축합고리 유도체는 다단계 화학반응으로 제조할 수 있다. 알킬화 반응, 그리냐르(Grignard) 반응, 스즈끼(Suzuki) 커플링 반응 및 스틸(Stille) 커플링 반응 등을 통하여 모노머들을 제조한 후, 스틸 커플링 반응 등의 탄소-탄소 커플링 반응을 통하여 최종 축합고리 유도체들을 제조할 수 있다. 도입하고자 하는 치환기가 보론산(boronic acid) 또는 보론산 에스터(boronic ester) 화합물인 경우에는 스즈키 커플링 반응을 통해 제조할 수 있고, 도입하고자 하는 치환기가 트리부틸틴(tributyltin) 또는 트리메틸틴(trimethyltin) 화합물인 경우에는 스틸 커플링 반응을 통해 제조할 수 있으나, 이에 한정되는 것은 아니다.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. When 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.
본 명세서의 일 실시상태에 있어서, 제1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 제2 전극 사이에 구비되고, 광활성층을 포함하는 1층 이상의 유기물층을 포함하고, 상기 유기물층 중 1층 이상은 상기 축합고리 유도체를 포함하는 것인 유기 태양 전지를 제공한다. In one embodiment of the present specification, 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.
본 명세서의 일 실시예에 따른 유기 태양 전지는 제1 전극, 광활성층 및 제2 전극을 포함한다. 상기 유기 태양 전지는 기판, 정공수송층 및/또는 전자수송층이 더 포함될 수 있다. 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.
본 명세서의 일 실시상태에 있어서, 상기 유기 태양 전지가 외부 광원으로부터 광자를 받으면 전자 주개와 전자 받개 사이에서 전자와 정공이 발생한다. 발생된 정공은 전자 도너층을 통하여 양극으로 수송된다. In one embodiment of the present specification, 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.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 정공 수송층, 정공 주입층 또는 정공 수송과 정공 주입을 동시에 하는 층을 포함하고, 상기 정공 수송층, 정공 주입층 또는 정공 수송과 정공 주입을 동시에 하는 층은 상기 축합고리 유도체를 포함한다. In one embodiment of the present specification, 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.
또 하나의 일 실시상태에 있어서, 상기 유기물층은 전자주입층, 전자 수송층 또는 전자 주입과 전자 수송을 동시에 하는 층을 포함하고, 상기 전자주입층, 전자 수송층 또는 전자 주입과 전자 수송을 동시에 하는 층은 상기 축합고리 유도체를 포함한다. In another exemplary embodiment, the organic material layer includes an electron injection layer, an electron transporting layer, or a layer for simultaneously injecting and transporting electrons, and the electron injection layer, an electron transporting layer, or a layer for simultaneously injecting and transporting electrons is It includes the condensed ring derivative.
도 1 본 명세서의 일 실시상태에 따른 유기 태양 전지를 나타낸 도이다.1 is a view showing an organic solar cell according to an exemplary embodiment of the present specification.
본 명세서의 일 실시상태에 있어서, 상기 유기 태양 전지가 외부 광원으로부터 광자를 받으면 전자 주개와 전자 받개 사이에서 전자와 정공이 발생한다. 발생된 정공은 전자 도너층을 통하여 양극으로 수송된다. In one embodiment of the present specification, 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.
본 명세서의 일 실시상태에 있어서, 상기 유기 태양 전지는 부가적인 유기물층을 더 포함할 수 있다. 상기 유기 태양 전지는 여러 기능을 동시에 갖는 유기물을 사용하여 유기물층의 수를 감소시킬 수 있다.In one embodiment of the present specification, 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.
본 명세서의 일 실시상태에 있어서, 상기 제1 전극은 애노드이고, 상기 제2 전극은 캐소드이다. 또 하나의 실시상태에 있어서, 상기 제1 전극은 캐소드이고, 상기 제2 전극은 애노드이다. In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode. In another exemplary embodiment, the first electrode is a cathode and the second electrode is an anode.
본 명세서의 일 실시상태에 있어서, 유기 태양 전지는 캐소드, 광활성층 및 애노드 순으로 배열될 수도 있고, 애노드, 광활성층 및 캐소드 순으로 배열될 수도 있으나, 이에 한정되지 않는다. In one embodiment of the present specification, 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.
또 하나의 실시상태에 있어서, 상기 유기 태양 전지는 애노드, 정공수송층, 광활성층, 전자수송층 및 캐소드 순으로 배열될 수도 있고, 캐소드, 전자수송층, 광활성층, 정공수송층 및 애노드 순으로 배열될 수도 있으나, 이에 한정되지 않는다.In another exemplary embodiment, 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.
본 명세서의 일 실시상태에 있어서, 상기 유기 태양 전지는 노멀(Normal)구조이다. In one embodiment of the present specification, the organic solar cell has a normal structure.
본 명세서의 일 실시상태에 있어서, 상기 유기 태양 전지는 인버티드(Inverted) 구조이다. In one embodiment of the present specification, the organic solar cell has an inverted structure.
본 명세서의 일 실시상태에 있어서, 상기 유기 태양 전지는 탠덤 (tandem) 구조이다. In one embodiment of the present specification, the organic solar cell has a tandem structure.
본 명세서의 일 실시상태에 따른 유기태양 전지는 광활성층이 1층 또는 2층 이상일 수 있다. In the organic solar cell according to the exemplary embodiment of the present specification, the photoactive layer may be one layer or two or more layers.
또 하나의 실시상태에 있어서, 버퍼층이 광활성층과 정공수송층 사이 또는 광활성층과 전자수송층 사이에 구비될 수 있다. 이때, 정공 주입층이 애노드와 정공수송층사이에 더 구비될 수 있다. 또한, 전자주입층이 캐소드와 전자수송층 사이에 더 구비될 수 있다. In another exemplary embodiment, 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. In this case, a hole injection layer may be further provided between the anode and the hole transport layer. In addition, an electron injection layer may be further provided between the cathode and the electron transport layer.
본 명세서의 일 실시상태에 있어서, 상기 광활성층은 전자 주개 및 받개로 이루어진 군에서 선택되는 1 또는 2 이상을 포함하고, 상기 전자 주개물질은 상기 축합고리 유도체를 포함한다. In one embodiment of the present specification, 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.
본 명세서의 일 실시상태에 있어서, 상기 전자 받개 물질은 플러렌, 플러렌 유도체, 바소쿠프로인, 반도체성 원소, 반도체성 화합물 및 이들의 조합으로 이루어진 군에서 선택될 수 있다. 구체적으로 플러렌(fullerene), 플러렌 유도체(PCBM((6,6)-phenyl-C61-butyric acid-methylester) 또는 PCBCR((6,6)-phenyl-C61-butyric acid-cholesteryl ester), 페릴렌(perylene) PBI(polybenzimidazole), 및 PTCBI(3,4,9,10-perylene-tetracarboxylic bis-benzimidazole)로 이루어진 군에서 선택되는 1 또는 2 이상의 화합물이다. In one embodiment of the present specification, the electron acceptor material may be selected from the group consisting of fullerenes, fullerene derivatives, vasocuprones, semiconducting elements, semiconducting compounds, and combinations thereof. Specifically, 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), and PTCBI (3,4,9,10-perylene-tetracarboxylic bis-benzimidazole) is one or more compounds selected from the group consisting of.
본 명세서의 일 실시상태에 있어서, 상기 전자 주개 및 전자 받개는 벌크 헤테로 정션(BHJ)을 구성한다. In one embodiment of the present specification, the electron donor and the electron acceptor constitute a bulk hetero junction (BHJ).
벌크 헤테로 정션이란 광활성층에서 전자 주개 물질과 전자 받개 물질이 서로 섞여 있는 것을 의미한다.Bulk heterojunction means that the electron donor material and the electron acceptor material are mixed with each other in the photoactive layer.
본 명세서의 일 실시상태에 있어서, 상기 광활성층은 n 형 유기물층 및 p 형 유기물층을 포함하는 이층 박막(bilayer) 구조이며, 상기 p형 유기물층은 상기 축합고리 유도체를 포함한다. In an exemplary embodiment of the present specification, 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.
본 명세서에서 상기 기판은 투명성, 표면평활성, 취급용이성 및 방수성이 우수한 유리기판 또는 투명 플라스틱 기판이 될 수 있으나, 이에 한정되지 않으며, 유기 태양 전지에 통상적으로 사용되는 기판이면 제한되지 않는다. 구체적으로 유리 또는 PET(polyethylene terephthalate), PEN(polyethylene naphthalate), PP(polypropylene), PI(polyimide), TAC(triacetyl cellulose) 등이 있으나. 이에 한정되는 것은 아니다. In the present specification, 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.
상기 애노드 전극은 투명하고 전도성이 우수한 물질이 될 수 있으나, 이에 한정되지 않는다. 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SNO2 : Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸싸이오펜), 폴리[3,4-(에틸렌-1,2-디옥시)싸이오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.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.
상기 애노드 전극의 형성 방법은 특별히 한정되지 않으나, 예컨대 스퍼터링, E-빔, 열증착, 스핀코팅, 스크린 프린팅, 잉크젯 프린팅, 닥터 블레이드 또는 그라비아 프린팅법을 사용하여 기판의 일면에 도포되거나 필름형태로 코팅됨으로써 형성될 수 있다.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.
상기 애노드 전극을 기판 상에 형성하는 경우, 이는 세정, 수분제거 및 친수성 개질 과정을 거칠 수 있다. When the anode electrode is formed on the substrate, it may be subjected to cleaning, water removal, and hydrophilic modification.
예컨대, 패터닝된 ITO 기판을 세정제, 아세톤, 이소프로필 알코올(IPA)로 순차적으로 세정한 다음, 수분 제거를 위해 가열판에서 100~150℃에서 1~30분간, 바람직하게는 120℃에서 10분간 건조하고, 기판이 완전히 세정되면 기판 표면을 친수성으로 개질한다.For example, 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. When the substrate is thoroughly cleaned, the surface of the substrate is modified to be hydrophilic.
상기와 같은 표면 개질을 통해 접합 표면 전위를 광활성층의 표면 전위에 적합한 수준으로 유지할 수 있다. 또한, 개질 시 애노드 전극 위에 고분자 박막의 형성이 용이해지고, 박막의 품질이 향상될 수도 있다. Through such surface modification, the bonding surface potential can be maintained at a level suitable for the surface potential of the photoactive layer. In addition, it is easy to form a polymer thin film on the anode electrode when the modification, the quality of the thin film may be improved.
애노드 전극의 위한 전 처리 기술로는 a) 평행 평판형 방전을 이용한 표면 산화법, b) 진공상태에서 UV 자외선을 이용하여 생성된 오존을 통해 표면을 산화하는 방법, 및 c) 플라즈마에 의해 생성된 산소 라디칼을 이용하여 산화하는 방법 등이 있다.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.
애노드 전극 또는 기판의 상태에 따라 상기 방법 중 한가지를 선택할 수 있다. 다만, 어느 방법을 이용하든지 공통적으로 애노드 전극 또는 기판 표면의 산소이탈을 방지하고 수분 및 유기물의 잔류를 최대한 억제하는 것이 바람직하다. 이 때, 전 처리의 실질적인 효과를 극대화할 수 있다. 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.
구체적인 예로서, UV를 이용하여 생성된 오존을 통해 표면을 산화하는 방법을 사용할 수 있다. 이 때, 초음파 세정 후 패터닝된 ITO 기판을 가열판(hot plate)에서 베이킹(baking)하여 잘 건조시킨 다음, 챔버에 투입하고, UV 램프를 작용시켜 산소 가스가 UV 광과 반응하여 발생하는 오존에 의하여 패터닝된 ITO 기판을 세정할 수 있다. As a specific example, a method of oxidizing a surface through ozone generated using UV may be used. At this time, after ultrasonic cleaning, 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.
그러나, 본 명세서에 있어서의 패터닝된 ITO 기판의 표면 개질 방법은 특별히 한정시킬 필요는 없으며, 기판을 산화시키는 방법이라면 어떠한 방법도 무방하다.However, 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.
상기 캐소드 전극은 일함수가 작은 금속이 될 수 있으나, 이에 한정되지 않는다. 구체적으로 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al, LiO2/Al, LiF/Fe, Al:Li, Al:BaF2, Al:BaF2:Ba와 같은 다층 구조의 물질이 될 수 있으나, 이에 한정되는 것은 아니다. The cathode electrode may be a metal having a small work function, but is not limited thereto. Specifically, 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.
상기 캐소드 전극은 5x10-
7torr 이하의 진공도를 보이는 열증착기 내부에서 증착되어 형성될 수 있으나, 이 방법에만 한정되는 것은 아니다.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.
상기 정공수송층 및/또는 전자수송층 물질은 광활성층에서 분리된 전자와 정공을 전극으로 효율적으로 전달시키는 역할을 담당하며, 물질을 특별히 제한하지는 않는다. 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.
상기 정공수송층 물질은 PEDOT:PSS(Poly(3,4-ethylenediocythiophene) doped with poly(styrenesulfonic acid)), 몰리브데늄 산화물(MoOx); 바나듐 산화물(V2O5); 니켈 산화물(NiO); 및 텅스텐 산화물(WOx) 등이 될 수 있으나, 이들에만 한정되는 것은 아니다. 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.
상기 전자수송층 물질은 전자추출금속 산화물(electron-extracting metal oxides)이 될 수 있으며, 구체적으로 8-히드록시퀴놀린의 금속착물; Alq3를 포함한 착물; Liq를 포함한 금속착물; LiF; Ca; 티타늄 산화물(TiOx); 아연 산화물(ZnO); 및 세슘 카보네이트(Cs2CO3) 등이 될 수 있으나, 이들에만 한정되는 것은 아니다.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.
광활성층은 전자공여체 및/또는 전자수용체와 같은 광활성 물질을 유기용매에 용해시킨 후 용액을 스핀 코팅, 딥코팅, 스크린 프린팅, 스프레이 코팅, 닥터 블레이드, 브러쉬 페인팅 등의 방법으로 형성할 수 있으나, 이들 방법에만 한정되는 것은 아니다.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.
상기 축합고리 유도체의 제조 방법 및 이를 포함하는 유기 태양 전지의 제조는 이하 제조예 및 실시예에서 구체적으로 설명한다. 그러나, 하기 실시예는 본 명세서를 예시하기 위한 것이며, 본 명세서의 범위가 이들에 의하여 한정되는 것은 아니다. The manufacturing method of the condensed ring derivative and the preparation of the organic solar cell including the same will be described in detail in the following Preparation Examples and Examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.
실시예Example
1. 화학식 1-1-1의 제조 1. Preparation of Chemical Formula 1-1-1
(1) 플라스크에 2-(5'-브로모-[2,2'-바이싸이오펜]-5일)-1,3-디옥솔란(2-(5'-bromo-[2,2'-bithiophen]-5-yl)-1,3-dioxolane) (3.04g, 9.6 mmol)을 120 mL 테트라하이드로퓨란(THF) 질소 하에서 녹인 후 -78 ℃로 온도를 낮추었다. 이 용액에 2.5 M n-부틸리튬(n-BuLi)을 (5mL, 12.5 mmol) 서서히 주입하고, 주입 후 0 ℃로 온도를 올린 후, 0 ℃에서 2시간 동안 교반하였다. 교반 후, 온도를 -78 ℃로 낮춘 뒤 트리메틸틴 클로라이드(trimethyltin chloride) (1M, 13 mmol)을 서서히 주입한 뒤, 상온으로 서서히 올려주었다. 반응물을 디클로로메탄(dichloromethane)으로 2번 추출(extraction)하고 용매를 제거한 뒤, CHCl3/MeOH 하에서 재결정하여 흰색의 화합물 A-1(3.844g, 수율=99.9%)을 얻었다.(1) 2- (5'-bromo- [2,2'-bithiophene] -5yl) -1,3-dioxolane (2- (5'-bromo- [2,2'-) bithiophen] -5-yl) -1,3-dioxolane) (3.04 g, 9.6 mmol) was dissolved in 120 mL tetrahydrofuran (THF) nitrogen and then cooled to -78 ° C. 2.5 M n-butyllithium (n-BuLi) (5 mL, 12.5 mmol) was slowly injected into the solution, the temperature was raised to 0 ° C. after the injection, and the mixture was stirred at 0 ° C. for 2 hours. After stirring, the temperature was lowered to -78 ° C, trimethyltin chloride (1M, 13 mmol) was slowly injected, and then slowly raised to room temperature. The reaction was extracted twice with dichloromethane, the solvent was removed, and recrystallized under CHCl 3 / MeOH to give white Compound A-1 (3.844g, yield = 99.9%).
도 2는 화합물 A-1의 MS 스펙트럼을 나타낸 도이다. 2 is a diagram showing an MS spectrum of Compound A-1.
도 3은 화합물 A-1의 NMR 스펙트럼을 나타낸 도이다. 3 is a diagram showing an NMR spectrum of Compound A-1.
(2) B-1의 화합물 (4,7-디브로모-5-플루오로벤조[c][1,2,5]티아디아졸; 4,7-dibromo-5-fluorobenzo[c][1,2,5]thiadiazole) (3.00 g, 9. 6 mmol), A-1의 화합물 (3.84 g, 9.58 mmol), Pd2(dba)3 (0.174 g, 0.19 mmol), 트리페닐포스핀(triphenylphosphine) (0.202 g, 0.77 mmol)을 100 mL의 톨루엔에 녹인 후 80 ℃에서 48시간 교반하였다. 반응 후, 상온으로 낮춘 뒤 2M 염산(HCl)를 넣고 1시간동안 교반하였다. 반응 후, 디클로로메탄(dichloromethane)으로 세척하고 용매를 감압 하에 제거 하였다. 얻어진 고체를 클로로포름(chloroform)을 이용하여 실리카 컬럼 정제를 하여 오렌지 색의 화합물 A-2 (1.67 g, 수율: 41 %)를 얻었다.(2) a compound of B-1 (4,7-dibromo-5-fluorobenzo [c] [1,2,5] thiadiazole; 4,7-dibromo-5-fluorobenzo [c] [1 , 2,5] thiadiazole) (3.00 g, 9. 6 mmol), a compound of A-1 (3.84 g, 9.58 mmol), Pd 2 (dba) 3 (0.174 g, 0.19 mmol), triphenylphosphine ) (0.202 g, 0.77 mmol) was dissolved in 100 mL of toluene and stirred at 80 ° C. for 48 hours. After the reaction, the mixture was cooled to room temperature, 2M hydrochloric acid (HCl) was added thereto, and the mixture was stirred for 1 hour. After the reaction, the mixture was washed with dichloromethane and the solvent was removed under reduced pressure. The obtained solid was purified by silica column using chloroform to give an orange compound A-2 (1.67 g, yield: 41%).
도 4는 화합물 A-2의 MS 스펙트럼을 나타낸 도이다. 4 is a diagram showing an MS spectrum of Compound A-2.
도 5는 화합물 A-2의 NMR 스펙트럼을 나타낸 도이다. 5 is a diagram showing an NMR spectrum of Compound A-2.
(3) B-2의 화합물 (0.858g, 0.8 mmol), A-2의 화합물 (0.850g, 2 mmol), Pd2(dba)3, 트리페닐포스핀(PPh3)을 톨루엔 37 mL와 디메틸포름아미드(DMF) 3Ml와 톨루엔에 넣고 녹인 후, 110 ℃에서 48시간 교반하였다. 반응 후, 상온으로 낮춘 뒤 디클로로메탄(dichloromethane)으로 세척하고 용매를 감압 하에 제거하였다. 얻어진 고체를 디클로로메탄(DCM)을 이용하여 실리카 컬럼 정제를 하여 보라색의 화합물 A-3(0.5g, 수율: 43%)을 얻었다.(3) Compound B-2 (0.858 g, 0.8 mmol), Compound A-2 (0.850 g, 2 mmol), Pd 2 (dba) 3 , Triphenylphosphine (PPh 3 ) in 37 mL of toluene and dimethyl 3Ml of formamide (DMF) and toluene were dissolved in the mixture, and the mixture was stirred at 110 ° C for 48 hours. After the reaction, the mixture was cooled to room temperature, washed with dichloromethane, and the solvent was removed under reduced pressure. The obtained solid was purified by silica column using dichloromethane (DCM) to give a purple compound A-3 (0.5 g, yield: 43%).
도 6은 화합물 A-3의 MS 스펙트럼을 나타낸 도이다. 6 is a diagram showing an MS spectrum of Compound A-3.
도 7은 화합물 A-3의 NMR 스펙트럼을 나타낸 도이다. 7 is a diagram showing an NMR spectrum of Compound A-3.
(4) 클로로포름(CHCl3) 25 mL에 화합물 A-3 (0.359 g, 0.25 mmol)과 3-옥틸로다닌 (3-octylrhodanine) (1.166 g, 4.75 mmol)을 녹이고 상온에서 피페리딘 (piperidine) 세 방울을 넣어주고 24 시간 동안 환류하였다. 반응 후, 디클로로메탄 (DCM)으로 추출한 후, 황산마그네슘(MgSO4; Magnesium sulfate)로 잔여 물을 제거 후, 감압 하에 용매를 제거하였다. 잔류 생성물을 실리카 컬럼(silica column, eluent: CH2Cl2 to CHCl3)을 통해서 어두운 갈색의 고체를 얻었다. 얻어진 고체를 클로로포름(CHCl3)과 헥산(Hexane)으로 두 세번 재결정을 통해 화학식 1-1-1의 화합물을 얻었다. (수율: 67%)(4) Dissolve compound A-3 (0.359 g, 0.25 mmol) and 3-octylrhodanine (1.166 g, 4.75 mmol) in 25 mL of chloroform (CHCl 3 ) at room temperature. Three drops were added and refluxed for 24 hours. After the reaction, the mixture was extracted with dichloromethane (DCM), and then residual water was removed with magnesium sulfate (MgSO 4 ; Magnesium sulfate), and then the solvent was removed under reduced pressure. The residual product was obtained through a silica column (eluent: CH 2 Cl 2 to CHCl 3 ) to give a dark brown solid. The obtained solid was recrystallized two or three times with chloroform (CHCl 3 ) and hexane (Hexane) to obtain a compound of Chemical Formula 1-1-1. (Yield 67%)
도 8은 화학식 1-1-1의 MS 스펙트럼을 나타낸 도이다. 8 is a diagram showing an MS spectrum of Chemical Formula 1-1-1.
도 9는 화학식 1-1-1의 NMR 스펙트럼을 나타낸 도이다. 9 is a diagram showing an NMR spectrum of Chemical Formula 1-1-1.
비교예Comparative example
1. 화학식 2의 제조 1. Preparation of Chemical Formula 2
15 mL 톨루엔에 B-2의 화합물 (0.8584 g, 0.8 mmol)과 [C]의 화합물 (0.963 g, 2.0 mmol)을 녹이고, Pd(PPh3)4 촉매 (0.0185 g, 0.016 mmol)을 넣고, 120 ℃에서 48시간 교반하였다. 반응 후, 반응 용액을 메탄올에 부어 침전한 후, 침전된 고체를 필터하였다. 필터된 고체를 메탄올로 씻어 주고, 실리카 컬럼(silica column, eluent: Hexane)을 통해서 보랏빛 갈색의 고체를 얻었다. 얻어진 고체를 헥산과 에탄올로 재결정하여 최종 화합물을 얻었다. (수율: 35%)In 15 mL toluene was dissolved B-2 compound (0.8584 g, 0.8 mmol) and [C] compound (0.963 g, 2.0 mmol), and Pd (PPh 3 ) 4 catalyst (0.0185 g, 0.016 mmol) was added thereto. It stirred at 48 degreeC. After the reaction, the reaction solution was poured into methanol to precipitate, and the precipitated solid was filtered out. The filtered solid was washed with methanol, and a violet brown solid was obtained through a silica column (eluent: Hexane). The obtained solid was recrystallized from hexane and ethanol to obtain the final compound. (Yield 35%)
도 10은 화학식 2의 MS 스펙트럼을 나타낸 도이다. 10 is a diagram showing an MS spectrum of Chemical Formula 2.
도 11은 화학식 2의 NMR 스펙트럼을 나타낸 도이다. 11 is a diagram showing an NMR spectrum of Chemical Formula 2.
도 12는 화학식 1-1-1과 화학식 2를 클로로벤젠 용액 내에서 UV스펙트럼을 비교한 도이다. 12 is a diagram comparing UV spectra of Chemical Formulas 1-1-1 and Chemical Formula 2 in a chlorobenzene solution.
상기 도 12의 결과로 보아, 화학식 1-1-1의 화합물이 화학식 2의 화합물보다 낮은 밴드갭을 가지며, 흡광계수(extinction coefficient)값이 약 두배 이상 높은 것을 확인할 수 있다. As a result of FIG. 12, it can be seen that 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.
도 13은 화학식 1-1-1과 화학식 2를 필름상태에서 UV 스펙트럼을 비교한 도이다. FIG. 13 is a view comparing UV spectra of Chemical Formulas 1-1-1 and Chemical Formula 2 in a film state. FIG.
상기 도 13의 결과로 보아, 화학식 1-1-1의 화합물이 낮은 밴드갭을 갖는 것을 확인할 수 있다. 또한, 열처리를 하였을 때, 진동 피크(vibronic peak)가 증가하는 것을 보아, 화학식 1-1-1의 결정성이 높다는 것을 확인할 수 있다. As a result of FIG. 13, it can be seen that the compound of Formula 1-1-1 has a low bandgap. In addition, when the heat treatment, 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.
따라서, 상기의 결과로 화학식 1-1-1의 화합물을 포함하는 유기 태양 전지는 전류 특성의 향상을 기대할 수 있다. Therefore, as a result, the organic solar cell including the compound of Formula 1-1-1 can be expected to improve the current characteristics.
도 14는 화학식 1-1-1의 전기화학 측정 결과(cyclic voltametry)를 나타낸 도이다.14 is a view illustrating an electrochemical measurement result (cyclic voltametry) of Chemical Formula 1-1-1.
도 15는 화학식 2의 전기화학 측정 결과(cyclic voltametry)를 나타낸 도이다.FIG. 15 is a diagram illustrating an electrochemical measurement result (cyclic voltametry) of Chemical Formula 2. FIG.
화학식 1-1-1과 화학식 2의 물성을 비교하면 하기 표 1과 같다. Comparing the physical properties of Formula 1-1-1 and Formula 2 is shown in Table 1 below.
| λmax (nm)λ max (nm) | λonset (nm)λ onset (nm) | λEc.band-gap (eV)λ Ec.band-gap (eV) | HOMO (eV)HOMO (eV) | |
| 화학식 1-1-1Formula 1-1-1 | 665665 | 740740 | 1.511.51 | 5.485.48 |
|
화학식 2 |
610610 | 685685 | 1.351.35 | 5.355.35 |
상기 도 14 및 15를 통한 HOMO 에너지 준위의 비교를 통하여, 화학식 1-1-1의 화합물의 HOMO 에너지 준위가 높은 것을 확인할 수 있다. 상기와 같은 결과는 말단에 Ar1 및 Ar2의 전자 받개 성질의 구조가 도입됨으로써 유도되는 것이다. Through comparison of the HOMO energy levels through FIGS. 14 and 15, it can be seen that the HOMO energy level of the compound of Formula 1-1-1 is high. The above results are derived by introducing the electron acceptor structures of Ar1 and Ar2 into the terminals.
상기의 결과로 화학식 1-1-1의 화합물을 포함하는 유기 태양 전지는 전압 특성의 향상을 기대할 수 있다. As a result, the organic solar cell including the compound of Formula 1-1-1 can be expected to improve the voltage characteristics.
실험예 1. Experimental Example 1.
상기 실시예에서 제조한 축합고리 유도체 1과 PCBM을 1:2로 클로로벤젠(Chlorobenzene, CB)에 녹여 복합 용액(composit solution)을 제조하였다. 이때, 농도는 2.0 wt%로 조절하였으며, 유기 태양전지는 ITO/PEDOT:PSS/광활성층/Al의 구조로 하였다. ITO가 코팅된 유리 기판은 증류수, 아세톤, 2-프로판올을 이용하여 초음파 세척하고, ITO 표면을 10분 동안 오존 처리한 후 45 nm 두께로 PEDOT:PSS(baytrom P)를 스핀코팅하여 120 ℃에서 10분 동안 열처리하였다. 광활성층의 코팅을 위해서는 화합물-PCBM 복합용액을 0.45 μm PP 주사기 필터(syringe filter)로 여과한 다음 스핀코팅하여, 3x10-8 torr 진공 하에서 열 증발기(thermal evaporator)를 이용하여 200 nm 두께로 Al을 증착하여 유기 태양 전지를 제조하였다. Condensed ring derivative 1 and PCBM prepared in the above Example 1: dissolved in chlorobenzene (Chlorobenzene, CB) 1: 2 to prepare a composite solution. At this time, 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. For the coating of the photoactive layer, the compound-PCBM composite solution was filtered through a 0.45 μm 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.
비교예 1. Comparative Example 1.
상기 실험예 1에서 화학식 1-1-1 대신 화학식 2를 사용한 것을 제외하고 동일한 방법으로 유기 태양 전지를 제조하였다. 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.
상기 실험예에서 제조된 유기 태양 전지의 광전 변환 특성을 100 mW/cm2(AM 1.5) 조건에서 측정하고, 하기 표 2에 그 결과를 나타내었다.The photoelectric conversion characteristics of the organic solar cell manufactured in the Experimental Example were measured under 100 mW / cm 2 (AM 1.5), and the results are shown in Table 2 below.
| Voc (V)V oc (V) | Jsc (mA/cm2)J sc (mA / cm 2 ) | FF (%)FF (%) | PCE (%)PCE (%) | |
| 실험예 1Experimental Example 1 | 0.910.91 | 11.4811.48 | 0.450.45 | 4.74.7 |
| 비교예 1Comparative Example 1 | 0.820.82 | 6.566.56 | 0.410.41 | 2.22.2 |
표 2에서 Voc는 개방전압을, Jsc는 단락전류를, FF는 충전율(Fill factor)를, PCE는 에너지 변환 효율을 의미한다. 개방전압과 단락전류는 각각 전압-전류 밀도 곡선의 4사분면에서 X축과 Y축 절편이며, 이 두 값이 높을수록 태양전지의 효율은 바람직하게 높아진다. 또한 충전율(Fill factor)은 곡선 내부에 그릴 수 있는 직사각형의 넓이를 단락전류와 개방전압의 곱으로 나눈 값이다. 이 세 가지 값을 조사된 빛의 세기로 나누면 에너지 변환 효율을 구할 수 있으며, 높은 값일수록 바람직하다.In Table 2, Voc is the open voltage, Jsc is the short-circuit current, FF is the fill factor, and 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. Also, 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.
도 16은 화학식 1-1-1과 화학식 2를 이용한 유기 태양 전지의 전압에 따른 전류 밀도를 나타낸 도이다. 16 is a diagram illustrating current densities according to voltages of organic solar cells using Chemical Formulas 1-1-1 and Chemical Formula 2;
상기의 결과로 보아, 본 명세서의 일 실시상태에 따른 축합고리 유도체를 포함하는 화합물은 높은 전압과 전류의 특성을 갖는 것을 확인할 수 있다. 이는 축합고리 유도체의 [Push]와 Ar1 및 Ar2의 구조적인 특성으로 인하여, 전자를 효율적으로 집중시켜 낮은 밴드갭과 높은 HOMO 에너지 준위를 갖기 때문으로 해석될 수 있다. As a result of the above, it can be seen that 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.
실험예Experimental Example
2 및 2 and
비교예Comparative example
2. 2.
상기 화학식 1-1-5의 화합물 및 하기 화학식 3의 화합물을 계산 화학 프로그램을 통하여 계산한 결과를 표 3에 나타내었다. 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.
구체적으로 가우시안 09(Gaussian 09) 프로그램을 사용하여, TD-DFT 계산을 수행하였으며, B3PW91 functional과 6-31G* basis set을 사용하였다. 계산에 사용한 키워드(keyword)는 #p B3PW91/6-31G* 5d td(singlets,nstate=10)이었다. Specifically, TD-DFT calculation was performed using Gaussian 09 program, and B3PW91 functional and 6-31G * basis set were used. The keyword used for the calculation was #p B3PW91 / 6-31G * 5d td (singlets, nstate = 10).
[화학식 3][Formula 3]
| 화학식Chemical formula | 밴드갭 (eV)Bandgap (eV) | HOMO (eV)HOMO (eV) | LUMO (eV)LUMO (eV) | |
| 실험예 2Experimental Example 2 | 1-1-51-1-5 | 1.441.44 | 5.435.43 | 3.993.99 |
| 비교예 2Comparative Example 2 | 22 | 1.461.46 | 5.385.38 | 3.913.91 |
도 17은 실험예 2와 비교예 2의 UV 스펙트럼의 경향을 분석한 도이다. 17 is a diagram analyzing the trend of the UV spectrum of Experimental Example 2 and Comparative Example 2.
표 3의 결과 및 도 17에서 알 수 있듯이, 본 명세서의 일 실시상태에 따른 축합고리 유도체와 같이, [Push] 구조와 X3를 포함하는 고리 및 X4를 포함하는 고리가 직접 연결되는 경우, [Push] 구조와 X3를 포함하는 고리 및 X4를 포함하는 고리 사이에 스페이서나 링커를 포함하는 경우보다 적색 편이한 것을 확인할 수 있다. As can be seen from the results of Table 3 and FIG. 17, like the condensed ring derivative according to the exemplary embodiment of the present specification, when the [Push] structure and the ring including X3 and the ring including X4 are directly connected, [Push] ] Red shifted between the structure and the ring containing X3 and the ring containing X4 than the case containing a spacer or a linker.
본 명세서의 일 실시상태에 따른 축합고리 유도체와 같이, 흡수 스펙트럼에서 적색편이 (red shift)가 일어는 경우, 장파장을 흡수할 수 있다. 또한, 분자 흡광 계수(Molar extinction coefficient)가 크고, 밴드갭이 줄어들어 많은 양의 빛을 흡수할 수 있어, 소자의 효율 증대에 긍정적인 영향을 줄 수 있다.Like the condensed ring derivative according to one embodiment of the present specification, when a red shift occurs in the absorption spectrum, the long wavelength may be absorbed. In addition, 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.
Claims (14)
- 하기 화학식 1로 표시되는 축합고리 유도체: Condensed ring derivative represented by the following formula (1):[화학식 1] [Formula 1]
화학식 1에 있어서, In Chemical Formula 1,n1 및 n2는 각각 0 내지 3의 정수이고, n1 and n2 are each an integer of 0 to 3,n1 및 n2가 각각 2 이상인 경우, 2 이상의 괄호 내의 구조는 서로 동일하거나 상이하며, when n1 and n2 are each 2 or more, the structures in the two or more parentheses are the same or different from each other,[Push]는 전자 주개로서 작용하는 구조이고, [Push] is a structure that acts as an electron donor,X1 내지 X4는 서로 동일하거나 상이하고, 각각 독립적으로 CRR', NR, O, SiRR', PR, S, GeRR', Se 또는 Te이며, 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 내지 Y4는 서로 동일하거나 상이하고, 각각 독립적으로 CR", N, SiR", P 또는 GeR"이고, Y1 to Y4 are the same as or different from each other, and each independently CR ″, N, SiR ″, P, or GeR ″,R, R', R" 및 R1 내지 R8은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 이미드기; 아미드기; 히드록시기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이며, 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 unsubstituted aralkyl Amine groups; substituted or unsubstituted arylamine groups; substituted or unsubstituted heteroarylamine groups; substituted or unsubstituted aryl groups; or substituted or unsubstituted heterocyclic groups,Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 하기 구조 중 어느 하나이고, Ar1 and Ar2 are the same as or different from each other, and each independently one of the following structures,
상기 구조에 있어서, In the above structure,a는 1 내지 7의 정수이고, a is an integer from 1 to 7,b 및 c는 각각 1 내지 4의 정수이며, b and c are each an integer of 1 to 4,a가 2 이상인 경우, 2 이상의 R15는 서로 동일하거나 상이하고, when a is 2 or more, two or more R15 are the same as or different from each other,b가 2 이상인 경우, 2 이상의 R16은 서로 동일하거나 상이하며, when b is 2 or more, two or more R16 are the same as or different from each other,c가 2 이상인 경우, 2 이상의 R17은 서로 동일하거나 상이하며, when c is 2 or more, two or more R17 are the same or different from each other,R13 내지 R23은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 이미드기; 아미드기; 히드록시기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다. 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; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group. - 청구항 1에 있어서, The method according to claim 1,[Push]의 HOMO(highest occupied molecular orbital) 에너지 준위는 5.0 eV 내지 6.0 eV 인 것인 축합고리 유도체.Condensed ring derivative of the highest occupied molecular orbital (HOMO) energy level of [Push] is 5.0 eV to 6.0 eV.
- 청구항 1에 있어서, The method according to claim 1,[Push]는 치환 또는 비치환된 아릴렌기; 및 치환 또는 비치환된 2가의 헤테로고리기로 이루어진 군에서 1 또는 2 이상을 포함하는 것인 축합고리 유도체.[Push] is a substituted or unsubstituted arylene group; And Condensed ring derivative comprising one or two or more in the group consisting of a substituted or unsubstituted divalent heterocyclic group.
- 청구항 1에 있어서, The method according to claim 1,[Push]는 하기 구조 중 어느 하나인 것인 축합고리 유도체: [Push] is a condensed ring derivative of any one of the following structures:
상기 구조에 있어서, In the above structure,d 및 d'는 각각 1 내지 3의 정수이고, d and d 'are each an integer of 1 to 3,d가 2 이상인 경우, 2 이상의 R100은 서로 동일하거나 상이하며, when d is 2 or more, two or more R100 are the same as or different from each other,d'가 2 이상인 경우, 2 이상의 R101은 서로 동일하거나 상이하고, when d 'is 2 or more, two or more R101 are the same as or different from each other,X10 내지 X13은 서로 동일하거나 상이하고, 각각 독립적으로 CRaRb, NRa, O, SiRaRb, PRa, S, GeRaRb, Se 또는 Te이며, 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 및 Y11은 서로 동일하거나 상이하고, 각각 독립적으로 CRc, N, SiRc, P 또는 GeRc이고,Y10 and Y11 are the same as or different from each other, and each independently CRc, N, SiRc, P, or GeRc,Ra, Rb, Rc 및 R100 내지 R103은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 이미드기; 아미드기; 히드록시기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.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 unsubstituted boron group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group. - 청구항 1에 있어서, The method according to claim 1,상기 화학식 1로 표시되는 축합고리 유도체는 하기 화학식 1-1 또는 1-2로 표시되는 것인 축합고리 유도체: Condensed ring derivative represented by Formula 1 is a condensed ring derivative represented by the following formula 1-1 or 1-2:[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
화학식 1-1 및 1-2에 있어서, In Chemical Formulas 1-1 and 1-2,n1 및 n2, X1 내지 X4, Y1 내지 Y4, R1 내지 R8, Ar1 및 Ar2는 화학식 1에서 정의한 바와 동일하고, n1 and n2, X1 to X4, Y1 to Y4, R1 to R8, Ar1 and Ar2 are the same as defined in Formula 1,X10 내지 X13은 서로 동일하거나 상이하고, 각각 독립적으로 CRaRb, NRa, O, SiRaRb, PRa, S, GeRaRb, Se 또는 Te이며, 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 및 Y11은 서로 동일하거나 상이하고, 각각 독립적으로 CRc, N, SiRc, P 또는 GeRc이고,Y10 and Y11 are the same as or different from each other, and each independently CRc, N, SiRc, P, or GeRc,Ra, Rb, Rc 및 R100 내지 R103은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 이미드기; 아미드기; 히드록시기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 헤테로아릴아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.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 unsubstituted boron group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group. - 청구항 1에 있어서, The method according to claim 1,R5 내지 R8은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 할로겐기; 또는 치환 또는 비치환된 알콕시기인 것인 축합고리 유도체.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.
- 청구항 1에 있어서, The method according to claim 1,X1 내지 X4는 S이고, X1 to X4 are S,Y1 내지 Y4는 N이며, Y1 to Y4 are N,Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로;
; 또는
이고, Ar1 and Ar2 are the same as or different from each other, and each independently
;; orego,R5 내지 R8은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 할로겐기; 또는 치환 또는 비치환된 알콕시기이며, 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 및 R23은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 또는 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기이고,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]는 S 원자를 1 이상 포함하는 헤테로고리기이며, 상기 헤테로고리기는 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기로 치환 또는 비치환된다. [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. - 청구항 1에 있어서, The method according to claim 1,상기 화학식 1로 표시되는 축합고리 유도체는 하기 화학식 1-1-1 내지 1-1-5 중 어느 하나로 표시되는 것인 축합고리 유도체:Condensed ring derivative represented by Formula 1 is a condensed ring derivative represented by any one of the following formula 1-1-1 to 1-1-5:[화학식 1-1-1][Formula 1-1-1]
[화학식 1-1-2][Formula 1-1-2]
[화학식 1-1-3][Formula 1-1-3]
[화학식 1-1-4][Formula 1-1-4]
[화학식 1-1-5][Formula 1-1-5].
. - 제1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비되고, 광활성층을 포함하는 1층 이상의 유기물층을 포함하고, 상기 유기물층 중 1층 이상은 청구항 1 내지 8 중 어느 하나의 항에 따른 축합고리 유도체를 포함하는 것인 유기 태양 전지.A 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 comprises a condensed ring derivative according to any one of claims 1 to 8. An organic solar cell comprising.
- 청구항 9에 있어서, The method according to claim 9,상기 유기물층은 정공 수송층, 정공 주입층 또는 정공 수송과 정공 주입을 동시에 하는 층을 포함하고, The organic material layer includes a hole transport layer, a hole injection layer or a layer for simultaneously performing hole transport and hole injection,상기 정공 수송층, 정공 주입층 또는 정공 수송과 정공 주입을 동시에 하는 층은 상기 축합고리 유도체를 포함하는 유기 태양 전지.The hole transport layer, the hole injection layer or a layer for simultaneously hole transport and hole injection comprises the condensed ring derivative.
- 청구항 9에 있어서, The method according to claim 9,상기 유기물층은 전자주입층, 전자 수송층 또는 전자 주입과 전자 수송을 동시에 하는 층을 포함하고, The organic material layer includes an electron injection layer, an electron transport layer or a layer for simultaneously injecting and transporting electrons,상기 전자주입층, 전자 수송층 또는 전자 주입과 전자 수송을 동시에 하는 층은 상기 축합고리 유도체를 포함하는 유기 태양 전지. And the electron injection layer, the electron transport layer, or the layer for simultaneously injecting and transporting electrons includes the condensed ring derivative.
- 청구항 9에 있어서, The method according to claim 9,상기 광활성층은 전자 주개 및 전자 받개로 이루어진 군에서 선택되는 1 또는 2 이상을 포함하고, The photoactive layer comprises one or two or more selected from the group consisting of an electron donor and an electron acceptor,상기 전자 주개는 상기 축합고리 유도체를 포함하는 것인 유기 태양 전지.The electron donor is an organic solar cell comprising the condensed ring derivative.
- 청구항 12에 있어서, The method according to claim 12,상기 전자 주개 및 전자 받개는 벌크 헤테로 정션(BHJ)을 구성하는 것인 유기 태양 전지.The electron donor and the electron acceptor constitute a bulk hetero junction (BHJ).
- 청구항 9에 있어서, The method according to claim 9,상기 광활성층은 n형 유기물층 및 p형 유기물층을 포함하는 이층 박막(bilayer)구조이며, The photoactive layer has a bilayer bilayer structure including an n-type organic compound layer and a p-type organic compound layer.상기 p형 유기물층은 상기 축합고리 유도체를 포함하는 것인 유기 태양 전지.The p-type organic compound layer is an organic solar cell comprising the condensed ring derivative.
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| CN109836437A (en) * | 2019-03-29 | 2019-06-04 | 南昌航空大学 | A kind of A-D-A type diazosulfide small molecule and its preparation method and application |
| CN112159418B (en) * | 2020-09-11 | 2024-04-05 | 中国科学院宁波材料技术与工程研究所 | Conjugated organic molecule and organic solar cell |
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| US9184315B2 (en) * | 2011-03-08 | 2015-11-10 | Nankai University | Photoelectric materials and preparation thereof |
| WO2014026244A1 (en) * | 2012-08-17 | 2014-02-20 | Commonwealth Scientific And Industrial Research Organisation | Photoactive optoelectronic and transistor devices |
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