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WO2015105354A1 - Dérivés de fullerène et dispositif électronique organique les comprenant - Google Patents

Dérivés de fullerène et dispositif électronique organique les comprenant Download PDF

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WO2015105354A1
WO2015105354A1 PCT/KR2015/000202 KR2015000202W WO2015105354A1 WO 2015105354 A1 WO2015105354 A1 WO 2015105354A1 KR 2015000202 W KR2015000202 W KR 2015000202W WO 2015105354 A1 WO2015105354 A1 WO 2015105354A1
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substituted
group
unsubstituted
electrode
organic
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English (en)
Korean (ko)
Inventor
배재순
이재철
이지영
최두환
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LG Chem Ltd
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LG Chem Ltd
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Priority claimed from KR1020140106083A external-priority patent/KR20150083006A/ko
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to JP2016545353A priority Critical patent/JP6306720B2/ja
Priority to CN201580003966.3A priority patent/CN105899456B/zh
Priority to US15/110,308 priority patent/US10693073B2/en
Priority to EP15735309.5A priority patent/EP3093270B1/fr
Publication of WO2015105354A1 publication Critical patent/WO2015105354A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/65—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing carbon
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B32/00—Carbon; Compounds thereof
    • C01B32/15—Nano-sized carbon materials
    • C01B32/152—Fullerenes
    • C01B32/156—After-treatment
    • 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
    • H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
    • H10K85/211—Fullerenes, e.g. C60
    • H10K85/215—Fullerenes, e.g. C60 comprising substituents, e.g. PCBM
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/20—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising organic-organic junctions, e.g. donor-acceptor junctions
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/50—Photovoltaic [PV] devices

Definitions

  • the present specification relates to a fullerene derivative and an organic electronic device including the same.
  • the organic electronic device refers to a device that requires charge exchange between an electrode and an organic material using holes and / or electrons.
  • the organic electronic device can be divided into two types according to the operating principle. First, an exciton is formed in the organic layer by photons introduced into the device from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is a form of electric element.
  • the second type is an electronic device in which holes and / or electrons are injected into an organic semiconductor forming an interface with the electrodes by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.
  • Examples of the organic electronic device include an organic light emitting device, an organic solar cell, an organic transistor, and the like, all of which require a hole injection or transport material, an electron injection or transport material, or a light emitting material for driving the device.
  • the organic solar cell will be described in detail.
  • a hole injection or transport material, an electron injection or transport material, or a light emitting material functions on a similar principle.
  • An object of the present specification is to provide an organic electronic device comprising a fullerene derivative.
  • An exemplary embodiment of the present specification provides a fullerene derivative represented by the following Chemical Formula 1.
  • n is an integer from 1 to 5
  • Cn is C 60 to C 120 fullerene
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; Halogen group; Nitro group; Cyano group; Carboxylic acid groups; Hydroxyl group; Substituted or unsubstituted carbonyl group; Sulfo group (-SO 3 H); Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted ester group; Substituted or unsubstituted thioester group; Substituted or unsubstituted amide group; Substituted or unsubstituted ether group; Substituted or unsubstituted sulfone group (-SO 2- ); Substituted or unsubstituted alkylthioxy group; Substi
  • o is an integer from 1 to 3, when o is an integer of 2 or more, two or more L are the same as or different from each other,
  • L is substituted or unsubstituted alkylene
  • R is hydrogen; Carboxylic acid groups; Substituted or unsubstituted carbonyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted ester group; Substituted or unsubstituted thioester group; Substituted or unsubstituted amide group; Substituted or unsubstituted sulfone group (-SO 2- ); Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • An exemplary embodiment of the present specification includes a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode.
  • At least one layer of the organic material layer provides an organic electronic device comprising the fullerene derivative.
  • An organic electronic device including a fullerene derivative according to one embodiment of the present specification shows an increase in efficiency and / or a rise in safety.
  • the fullerene derivative according to one embodiment of the present specification may be used purely or mixed with impurities in an organic electronic device including an organic solar cell, and may be applied by vacuum deposition or solution coating.
  • the organic electronic device including the fullerene derivative according to the exemplary embodiment of the present specification has excellent light efficiency, excellent thermal stability, and improved lifespan characteristics.
  • FIG. 1 illustrates an organic solar cell according to an exemplary embodiment of the present specification.
  • Fullerene derivative according to one embodiment of the present specification It includes at least one.
  • the morphology characteristic with the electron donor can be changed depending on the type of L and the type of R, so that the efficiency can be increased.
  • the fullerene derivative according to one embodiment of the present specification may improve the solubility, that is, solubility, in an organic solvent through the control of L and R.
  • a new crystalline film structure can be formed with a hydrophobic property with an alkyl group introduced to increase the solubility of the electron donor.
  • the fullerene derivative represented by Chemical Formula 1 is represented by the following Chemical Formula 2 or 3.
  • R, Cn, n, o, L and R1 to R6 are the same as defined in Chemical Formula 1.
  • R is a substituted or unsubstituted carbonyl group.
  • the fullerene derivative represented by Chemical Formula 1 provides an organic electronic device including a fullerene derivative represented by Chemical Formula 2-1 or Chemical Formula 3-1.
  • R7 and R8 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted ether group; Substituted or unsubstituted sulfonyl group; Substituted or unsubstituted arylalkyl group; Substituted or unsubstituted cyclic ketones; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • substituted or unsubstituted refers to a halogen group; Nitro group; Cyano group; Carboxyl groups; Hydroxyl group; Carbonyl group; Sulfo groups; An alkyl group; Allyl group; An alkoxy group; Cycloalkyl group; Alkenyl groups; Ester group; Ether group; Sulfone groups; Drinking time; Arylalkyl group; Aryl group; It means substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group, or substituted or unsubstituted with a substituent to which two or more substituents among the above-described substituents are linked.
  • 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.
  • substituted means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
  • the halogen group may be fluorine, chlorine, bromine or iodine.
  • Z is hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 40. Specific examples include, but are not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonanyl, decanyl, undecanyl, dodecanyl, and isosanyl, These may be branched chains or substituted forms.
  • the cycloalkyl group is not particularly limited, but preferably 3 to 60 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, norbornyl group, adamantyl group, and the like. There is, but is not limited to these, substituted forms thereof are also possible.
  • 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-C40. 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, 2-ethylhexyloxy, 2-methylheptyloxy, 2-propylbutyloxy, n- Nonyloxy, n-decyloxy, and the like, but is not limited thereto.
  • the arylalkyl group is not particularly limited in carbon number, but in one embodiment of the present specification, the arylalkyl group has 7 to 50 carbon atoms. Specifically, the aryl moiety has 6 to 49 carbon atoms, and the alkyl moiety has 1 to 44 carbon atoms.
  • phenylmethyl group phenylethyl group, phenylpropyl group, phenylisopropyl group, phenylbutyl group, phenylisobutyl group, phenylpentyl group, phenylisopentyl group, phenylhexyl group, phenylisohexyl group, phenylheptyl group and pefe.
  • Tyloctyl group phenylnonanyl group, phenyldecanyl group, naphthylmethyl group, naphthylethyl group, naphthylpropyl group, naphthylisopropyl group, pyrenylmethyl group, pyrenylethyl group, pyrenylpropyl group, pyrenylisopropyl group, pi Rollylmethyl group, pyrrolylethyl group, aminophenylmethyl group, nitrophenylmethyl group, cyanophenylmethyl group, 1-hydroxy-2-phenylisopropyl group, 1-chloro-2-phenylisopropyl group, thiophenylmethyl group, thiophenylethyl group , Thiophenylpropyl group, thiophenylisopropyl group, thiophenylbutyl group and the like, but is not limited thereto, and substituted forms thereof are also possible.
  • 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 general formula of the thioester group is It may be represented as.
  • Z 1 is hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms containing at least one of N, O and S atoms.
  • Z 2 is hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms containing at least one of N, O and S atoms.
  • the aryl group may be monocyclic, and the carbon number is not particularly limited, but is preferably 6 to 60 carbon atoms.
  • Specific examples of the aryl group include monocyclic aromatic and naphthyl groups such as phenyl group, biphenyl group, and terphenyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, tetrasenyl group, chrysenyl group, fluorenyl group, Polycyclic aromatics, such as an acenaphthacenyl group, a triphenylene group, and a fluoranthene group, etc., are not limited to these, It can be substituted by further substituents.
  • the heterocyclic group includes one or more atoms other than carbon and hetero atoms, and specifically, the hetero atoms may include one or more atoms selected from the group consisting of O, N, and S, and the like.
  • carbon number of a heterocyclic group is not specifically limited, It is preferable that it is C2-C60.
  • heterocyclic group examples include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, triazine group, acridil group, pyridazine group , Quinolinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthrroline group (phenanthroline) and dibenzofuranyl groups, and the like, but are not limited thereto, and may be substituted with additional substituents.
  • the general formula of the ester group is or It may be represented as.
  • Z ' is hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms; Heteroarylalkyl group having 2 to 60 carbon atoms; Substituted or unsubstituted carbonyl group having 1 to 40 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms containing at least one of N, O and S atoms.
  • Adjacent groups herein are R1 or R2 and R3; R3 and R4; R4 and R5 or R6; It means a substituent substituted on a neighboring carbon, such as R1 or R2 and R5 or R6.
  • the adjacent groups are bonded to each other to form a hydrocarbon ring or a hetero ring, in which the adjacent substituents form a bond, a 5- to 7-membered monocyclic or polycyclic hydrocarbon ring or a 5- to 7-membered monocyclic or multi It means forming the heterocyclic group of the ring.
  • the hydrocarbon ring is a cycloalkyl group; Cycloalkenyl group; Aromatic ring groups; Or include all aliphatic ring groups, which may be monocyclic or polycyclic, and include all rings condensed by combining one or two or more.
  • Heterocycle formed herein means that at least one carbon atom of the hydrocarbon ring is substituted with N, O, or S atoms, may be an aliphatic ring or an aromatic ring, it may be monocyclic or polycyclic.
  • o is 1.
  • L is a substituted or unsubstituted alkylene group.
  • L is an alkylene group.
  • L is a methylene group.
  • R1 is hydrogen
  • R2 is hydrogen
  • R3 is hydrogen
  • R4 is hydrogen
  • R5 is hydrogen
  • R5 is a substituted or unsubstituted alkyl group.
  • R5 is a methyl group.
  • R6 is hydrogen
  • R6 is a substituted or unsubstituted alkyl group.
  • R6 is a methyl group.
  • R is hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted carbonyl group.
  • R is hydrogen
  • R is a substituted or unsubstituted alkyl group.
  • R is a substituted or unsubstituted octyl group.
  • R is an octyl group.
  • R is a substituted or unsubstituted carbonyl group.
  • R is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cyclic ketone and a substitution comprising at least one of N, O and S atoms. Or a carbonyl group unsubstituted or substituted with a substituent selected from the group consisting of an unsubstituted heteroring group.
  • R is a carbonyl group unsubstituted or substituted with a substituted or unsubstituted alkyl group.
  • R is a carbonyl group unsubstituted or substituted with an alkyl group.
  • R is a carbonyl group unsubstituted or substituted with a branched alkyl group.
  • R is a carbonyl group substituted with a 2-methylpentyl group.
  • R is a carbonyl group unsubstituted or substituted with a linear alkyl group.
  • R is a carbonyl group substituted with a methyl group.
  • R is a carbonyl group substituted with an octyl group.
  • R is a carbonyl group substituted with a 1-octyl group.
  • R is a carbonyl group substituted with a 3-octyl group.
  • R is a carbonyl group substituted with an alkyl group unsubstituted or substituted with a substituted or unsubstituted aryl group.
  • R is a carbonyl group substituted with an alkyl group unsubstituted or substituted with a phenyl group.
  • R is a carbonyl group substituted with a propyl group unsubstituted or substituted with a phenyl group.
  • R is a carbonyl group substituted with an alkyl group substituted with a phenyl group unsubstituted or substituted with an amine group.
  • R is a carbonyl group substituted with a pentyl group substituted with a phenyl group.
  • R is a carbonyl group substituted with an ethyl group substituted with a phenyl group substituted with an amine group substituted with an alkyl group and / or an aryl group.
  • R is a carbonyl group substituted with an ethyl group substituted with a phenyl group substituted with a hexyl phenyl amine group.
  • R is a carbonyl group substituted with an alkyl group substituted with an aryl group unsubstituted or substituted with a substituted or unsubstituted heteroring group including one or more of N, O and S atoms.
  • R is a carbonyl group substituted with an alkyl group substituted with a phenyl group substituted with a substituted or unsubstituted heteroring group including one or more N atoms.
  • R is a carbonyl group substituted with an ethyl group substituted with a phenyl group substituted with a carbazole group.
  • R is a carbonyl group substituted with an ethyl group substituted with a phenyl group substituted with a benzoimidazole group substituted with a phenyl group.
  • R is a carbonyl group substituted with an alkyl group substituted with an alkoxy group.
  • R is a carbonyl group substituted with tetraoxatridecanyl.
  • R is a carbonyl group substituted with an alkyl group unsubstituted or substituted with a substituted or unsubstituted carbonyl group.
  • R is a carbonyl group substituted with an alkyl group substituted with a carbonyl group unsubstituted or substituted with an aryl group.
  • R is a carbonyl group substituted with an alkyl group substituted with a carbonyl group substituted with a phenyl group.
  • R is a carbonyl group substituted with an ethyl group substituted with a carbonyl group substituted with a phenyl group.
  • R is a carbonyl group substituted with a butyl group substituted with a carbonyl group substituted with a phenyl group.
  • R is a carbonyl group substituted with an alkyl group substituted with a carbonyl group unsubstituted or substituted with an alkyl group.
  • R is a carbonyl group substituted with a butyl group substituted with a carbonyl group substituted with an alkyl group.
  • R is a carbonyl group substituted with a butyl group substituted with a carbonyl group substituted with a methyl group.
  • R is a carbonyl group substituted with an alkyl group substituted with a substituted or unsubstituted ester group.
  • R is a carbonyl group substituted with an alkyl group substituted with an ester group substituted with an alkyl group.
  • R is a carbonyl group substituted with a propyl group substituted with an ester group substituted with a methyl group.
  • R is a carbonyl group substituted with an alkyl group substituted with a substituted or unsubstituted cyclic ketone group.
  • R is a carbonyl group substituted with an alkyl group substituted with a substituted or unsubstituted chromenone group.
  • R is a carbonyl group substituted with an alkyl group substituted with a chromenone group substituted with a halogen group.
  • R is a carbonyl group substituted with an ethyl group substituted with a chromenone group substituted with fluorine.
  • R is a carbonyl group substituted with an alkyl group unsubstituted or substituted with a substituted or unsubstituted heteroring group including one or more of N, O, and S atoms.
  • R is a carbonyl group substituted with an alkyl group substituted with a substituted or unsubstituted heterocyclic group including one or more S atoms.
  • R is a carbonyl group substituted with an alkyl group substituted with an thiophene group unsubstituted or substituted with an alkyl group.
  • R is a carbonyl group substituted with a propyl group substituted with a thiophene group substituted with a hexyl group.
  • R is a carbonyl group unsubstituted or substituted with a substituted or unsubstituted aryl group.
  • R is a carbonyl group substituted with a substituted or unsubstituted phenyl group.
  • R is a carbonyl group substituted with a phenyl group.
  • R is a carbonyl group substituted with a substituted or unsubstituted naphthyl group.
  • R is a carbonyl group substituted with a naphthyl group.
  • R is a carbonyl group substituted with a substituted or unsubstituted anthracenyl group.
  • R is a carbonyl group substituted with an anthracenyl group.
  • R is a carbonyl group substituted with a substituted or unsubstituted pyrene group.
  • R is a carbonyl group substituted with a pyrene group.
  • R is a carbonyl group unsubstituted or substituted with a substituted or unsubstituted heteroring group including one or more of N, O, and S atoms.
  • R is a carbonyl group unsubstituted or substituted with a substituted or unsubstituted heteroring group including one or more S atoms.
  • R is a carbonyl group unsubstituted or substituted with a substituted or unsubstituted thiophene group.
  • R is a carbonyl group substituted with a thiophene group substituted with a heterocyclic group containing one or more S atoms substituted with an alkyl group.
  • R is a carbonyl group substituted with a thiophene group substituted with a thiophene group substituted with an alkyl group.
  • R is a carbonyl group substituted with a thiophene group substituted with a thiophene group unsubstituted or substituted with a hexyl group.
  • R is a carbonyl group substituted with a substituted or unsubstituted cyclic ketone group.
  • R is a carbonyl group substituted with cyclic butanone.
  • R is a carbonyl group substituted with a cyclic pentanone.
  • R is a carbonyl group substituted with naphthalenone.
  • R is a carbonyl group substituted with dihydronaphthalenone.
  • R is a carbonyl group substituted with a chromenone group.
  • R is a carbonyl group substituted with an alkenyl group.
  • R is a carbonyl group substituted with a substituted or unsubstituted ethenyl group.
  • R is a carbonyl group substituted with an ethenyl group.
  • R is a carbonyl group substituted with an ethenyl group substituted with a phenyl group.
  • R is a carbonyl group substituted with an ethenyl group substituted with an alkyl group.
  • R is a carbonyl group substituted with an ethenyl group substituted with a methyl group.
  • R7 and R8 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted cyclic ketones; Or a substituted or unsubstituted heteroring group.
  • R8 is a substituted or unsubstituted alkyl group.
  • R8 is a branched alkyl group.
  • R8 is a 2-methylpentyl group.
  • R8 is a linear alkyl group.
  • R8 is a substituted or unsubstituted methyl group.
  • R8 is a methyl group.
  • R8 is an octyl group.
  • R8 is a 1-octyl group.
  • R8 is a 3-octyl group.
  • R8 is an alkyl group unsubstituted or substituted with a substituted or unsubstituted aryl group.
  • R8 is an alkyl group unsubstituted or substituted with a phenyl group.
  • R8 is a propyl group unsubstituted or substituted with a phenyl group.
  • R8 is a pentyl group unsubstituted or substituted with a phenyl group.
  • R8 is an alkyl group substituted with a phenyl group unsubstituted or substituted with an amine group.
  • R8 is an ethyl group substituted with a phenyl group substituted with an amine group substituted with an alkyl group and / or an aryl group.
  • R8 is an ethyl group substituted with a phenyl group substituted with a hexyl phenyl amine group.
  • R8 is an alkyl group substituted with an aryl group unsubstituted or substituted with a substituted or unsubstituted heteroring group including one or more of N, O and S atoms.
  • R8 is an alkyl group substituted with a phenyl group substituted with a substituted or unsubstituted heteroring group including one or more N atoms.
  • R8 is an ethyl group substituted with a phenyl group substituted with a carbazole group.
  • R8 is an ethyl group substituted with a phenyl group substituted with a benzoimidazole group substituted with a phenyl group.
  • R8 is an alkyl group substituted with an alkoxy group.
  • R8 is a tetraoxatridecanyl group.
  • R8 is an alkyl group unsubstituted or substituted with a substituted or unsubstituted substituted or unsubstituted carbonyl group.
  • R8 is an alkyl group substituted with a carbonyl group unsubstituted or substituted with an aryl group.
  • R8 is an alkyl group substituted with a carbonyl group substituted with a phenyl group.
  • R8 is an ethyl group substituted with a carbonyl group substituted with a phenyl group.
  • R8 is a butyl group substituted with a carbonyl group substituted with a phenyl group.
  • R8 is an alkyl group substituted with a carbonyl group unsubstituted or substituted with an alkyl group.
  • R8 is a butyl group substituted with a carbonyl group substituted with an alkyl group.
  • R8 is a butyl group substituted with a carbonyl group substituted with a methyl group.
  • R8 is an alkyl group substituted with a substituted or unsubstituted ester group.
  • R8 is an alkyl group substituted with an ester group substituted with an alkyl group.
  • R8 is a propyl group substituted with an ester group substituted with a methyl group.
  • R8 is an alkyl group substituted with a substituted or unsubstituted cyclic ketone group.
  • R8 is an alkyl group substituted with a substituted or unsubstituted chromenone group.
  • R8 is an alkyl group substituted with a chromenone group substituted with a halogen group.
  • R8 is an ethyl group substituted with a chromenone group substituted with fluorine.
  • R8 is an alkyl group unsubstituted or substituted with a substituted or unsubstituted heteroring group including one or more of N, O, and S atoms.
  • R8 is an alkyl group substituted with a substituted or unsubstituted heterocyclic group including one or more S atoms.
  • R8 is an alkyl group substituted with a thiophene group unsubstituted or substituted with an alkyl group.
  • R8 is a propyl group substituted with a thiophene group substituted with a hexyl group.
  • R8 is a substituted or unsubstituted aryl group.
  • R8 is a substituted or unsubstituted phenyl group.
  • R8 is a phenyl group.
  • R8 is a substituted or unsubstituted naphthyl group.
  • R8 is a naphthyl group.
  • R8 is a substituted or unsubstituted pyrene group.
  • R8 is a pyrene group.
  • R8 is a substituted or unsubstituted anthracene group.
  • R8 is an anthracene group.
  • R8 is a substituted or unsubstituted heteroring group including one or more of N, O and S atoms.
  • R8 is a substituted or unsubstituted heteroring group including one or more S atoms.
  • R8 is a substituted or unsubstituted thiophene group.
  • R8 is a thiophene group substituted with a thiophene group substituted with a heterocyclic group containing one or more S atoms substituted with an alkyl group.
  • R8 is a thiophene group substituted with a thiophene group substituted with an alkyl group.
  • R8 is a carbonyl group substituted with a thiophene group substituted with a thiophene group unsubstituted or substituted with a hexyl group.
  • R8 is a substituted or unsubstituted cyclic ketone group.
  • R8 is a cyclic butanone group.
  • R8 is a cyclic pentanone group.
  • R8 is a naphthalenone group.
  • R8 is a dihydronaphthale group.
  • R8 is a chromenone group.
  • R8 is a substituted or unsubstituted alkenyl group.
  • R8 is a substituted or unsubstituted ethenyl group.
  • R8 is an ethenyl group.
  • R8 is an ethenyl group substituted with a phenyl group.
  • R8 is an ethenyl group substituted with an alkyl group.
  • R8 is an ethenyl group substituted with a methyl group.
  • the fullerene derivative represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1-1 to 1-1-31.
  • n is the same as defined in the formula (1).
  • the fullerene derivative according to the exemplary embodiment of the present specification may further include another structure in addition to the structure in parentheses in Formula 1.
  • only one type may be used for the fullerene skeleton of the fullerene derivative, or may be used in combination of any two or more types.
  • the fullerene derivative represented by Chemical Formula 1 may be prepared based on the preparation examples described below.
  • a conjugated diene and a fullerene may be combined through a Diels-Alder reaction to prepare a fullerene derivative including a structure including a cyclohexane.
  • the fullerene derivatives represented by the general formula (1) as well as the fullerene derivatives of the general formulas (1-1-1 to 1-1-27) can be prepared.
  • 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, wherein at least one of the organic material layers includes the above-described fullerene derivative.
  • the organic electronic device is an organic light emitting device; Organic solar cells; And organic transistors.
  • the organic electronic device may be an organic light emitting device.
  • an organic light emitting device including a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein at least one layer of the organic layer is It provides an organic electronic device comprising a fullerene derivative.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the fullerene derivative.
  • the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the fullerene derivative.
  • the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer includes the fullerene derivative.
  • the organic electronic device may be an organic transistor.
  • an organic transistor including a source, a drain, a gate, and one or more organic material layers, and at least one of the organic material layers provides an organic electronic device including the fullerene derivative.
  • the organic electronic device may be an organic solar cell.
  • the organic electronic device includes 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, wherein at least one of the organic material layers includes the fullerene derivative.
  • the principle of an organic solar cell is that the p-type semiconductor forms an exciton where electrons and holes are paired by photo excitation, and the exciton is separated into electrons and holes at the p-n junction.
  • the separated electrons and holes move to the n-type semiconductor thin film and the p-type semiconductor thin film, respectively, and they are collected by the first electrode and the second electrode, respectively, so that they can be used as electrical energy from the outside.
  • FIG. 1 is a diagram illustrating an organic solar cell according to an exemplary embodiment of the present specification.
  • a substrate 101, a first electrode 102, a hole transport layer 103, a photoactive layer 104, and a second electrode 105 are included.
  • the organic material layer includes a photoactive layer and an organic material layer provided between the photoactive layer and the first electrode or the second electrode, and the photoactive layer and the first electrode or the second electrode.
  • the organic material layer provided between includes the fullerene derivative.
  • the organic material layer includes a photoactive layer
  • the photoactive layer has a bilayer structure including a n-type organic material layer and a p-type organic material layer
  • the n-type organic material layer includes the fullerene derivative. do.
  • the organic material layer includes a photoactive layer
  • the photoactive layer includes an electron donor material and an electron acceptor material
  • the electron acceptor material includes the fullerene derivative
  • the electron donor material and the electron acceptor material constitute a bulk heterojunction (BHJ).
  • Bulk heterojunction means that the electron donor material and the electron acceptor material are mixed with each other in the photoactive layer.
  • the electron acceptor material includes the fullerene derivative which is not heat cured or UV cured.
  • the fullerene derivative according to one embodiment of the present specification may be used as it is without thermal curing or UV curing.
  • the electron acceptor material including the fullerene derivative represented by Chemical Formula 1 may be applied to the photoactive layer as it is without heat curing or UV curing. Thus, there is a time and / or cost advantage of the process.
  • the electron acceptor material includes the fullerene derivative subjected to thermosetting or UV curing as necessary.
  • a new matrix may be formed with the electron donor material through UV or thermosetting treatment.
  • a new matrix may be formed between the electron acceptor materials through UV or heat curing.
  • the n-type organic compound layer and / or the electron donor material is well matched to the light absorption wavelength range or the solar spectrum, has a strong light absorption, excellent electrical properties such as charge mobility. It is preferable.
  • the electron donor material includes an organic compound, and the organic compound is an organic compound capable of a solution process.
  • the n-type organic compound layer and / or electron donor material includes an organic compound, and the organic compound includes a polymer or a single molecule.
  • electron donor materials include the following structures, including PPV (poly (phenylene vinylene))-based polymer or P3HT (poly (3-hexylthiophene))-based polymer.
  • n is an integer from 1 to 1,000
  • Rm is hydrogen, a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aromatic or aliphatic heterocyclic group containing one or more of N, O, S atoms, or substituted or unsubstituted aryl group.
  • the electron donor materials are preferably materials having a small band gap so as to absorb the entire visible light region of sunlight, and high molecular compounds are not limited thereto, but monomolecular compounds are also possible.
  • the electron donor material and the electron acceptor material are mixed in a ratio (w / w) of 1: 100 to 100: 1. After the electron donor material and the electron acceptor material are mixed, they may be annealed at 30 ° C. to 300 ° C. for 1 second to 24 hours to maximize properties.
  • the thickness of the photoactive layer is 10 nm to 10,000 nm.
  • the organic material layer is a photoactive layer; And an organic material layer provided between the photoactive layer and the first electrode or the second electrode, and the organic material layer provided between the photoactive layer and the first electrode or the second electrode includes the fullerene derivative.
  • the organic material layer includes an organic material layer provided between the photoactive layer and the first electrode or the second electrode, and the fullerene derivative is an electron acceptor and an electron transport material.
  • the organic material layer includes an organic material layer provided between the photoactive layer and the first electrode or the second electrode, and includes a metal oxide, between the metal oxide layer and the photoactive layer.
  • An organic material layer is provided, and the organic material layer includes the fullerene derivative.
  • the organic material layer including the fullerene derivative contacts the metal oxide.
  • the organic material layer provided between the photoactive layer and the first electrode or the second electrode includes the fullerene derivative, and the fullerene derivative is an electron injection material.
  • the organic electronic device has a normal structure.
  • the organic electronic device has an inverted structure.
  • the organic electronic device has a normal structure, and the organic material layer includes a photoactive layer; And an organic material layer provided between the photoactive layer and the second electrode, wherein the organic material layer provided between the photoactive layer and the second electrode includes the fullerene derivative, and the first electrode is an anode electrode and the second The electrode is a cathode electrode.
  • the organic electronic device has an inverted structure
  • the organic material layer includes an organic material layer provided between the photoactive layer and the second electrode, and between the photoactive layer and the second electrode.
  • the organic layer provided in the includes the fullerene derivative, wherein the first electrode is an anode electrode, the second electrode is a cathode electrode.
  • the first electrode may be an anode electrode or a cathode electrode.
  • the second electrode may be a cathode electrode and may be an anode electrode.
  • the organic solar cell may be arranged in order of an anode electrode, a photoactive layer, and a cathode electrode.
  • the cathode electrode, the photoactive layer, and the anode electrode may be arranged in this order, but are not limited thereto.
  • the organic solar cell may be arranged in order of an anode electrode, a hole transport layer, a photoactive layer, an electron transport layer, and a cathode electrode, and in order of a cathode electrode, an electron transport layer, a photoactive layer, a hole transport layer, and an anode electrode. It may be arranged, but is not limited thereto.
  • the organic solar cell may be arranged in order of an anode electrode, a buffer layer, a photoactive layer, and a cathode electrode.
  • the organic solar cell of the present specification may be manufactured by materials and methods known in the art, except that the fullerene derivative represented by Chemical Formula 1 is included in at least one layer of the organic material layer of the organic solar cell.
  • preparing a substrate Forming a first electrode on the substrate; Forming at least one organic layer including a photoactive layer on the first electrode; And forming a second electrode on the organic material layer, wherein the one or more organic material layers provide a method of manufacturing an organic solar cell including the fullerene derivative.
  • the fullerene derivative may include the hole transport layer; Photoactive layer; And / or in the electron transport layer.
  • the organic solar cell according to the present invention uses a metal vapor deposition (PVD) solution coating method such as sputtering or e-beam evaporation, or the like to form a metal oxide or a conductive metal oxide on a substrate.
  • PVD metal vapor deposition
  • These alloys may be prepared by depositing or solution coating to form an anode, and forming the organic material layer thereon by vacuum deposition or solution coating, and then depositing a material that can be used as a cathode thereon.
  • the organic layer of each layer is a solution process, such as roll to roll, spin coating, dip coating, casting, roll court, and flow, using various monomolecular or polymer materials, rather than deposition. It can be prepared by a method such as coating, doctor blading, screen printing, inkjet printing, gravure printing, offset printing, spray coating or thermal transfer.
  • the organic material layer of each layer, vacuum deposition, sputtering, plasma, ion plating can be produced by a method such as dry film forming method.
  • an anode deposition step, a photoactive layer stacking step, a photoactive layer alignment step, a photoactive layer heat treatment step may include a cathode deposition step.
  • the photoactive layer stacking step may be disposed in a complex thin film structure, that is, bulk hetero junction, in which a solution containing an electron donor material and an electron acceptor material is sprayed and deposited on an upper side of the anode.
  • the electron acceptor material may be a mixed solution of a composite polymer material dissolved in an organic solvent, and the electron acceptor material may include the aforementioned fullerene derivative.
  • P3HT is dissolved in an organic solvent and used in the fullerene 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), molybdenum oxide, 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, and isopropyl alcohol (IPA), and then 1 to 30 minutes at 100 ° C. to 150 ° C., preferably at 120 ° C. for 10 minutes, on a heating plate 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 may be formed by being deposited in a thermal evaporator showing a vacuum degree of 5 ⁇ 10 ⁇ 7 torr or less, but is not limited thereto.
  • the hole transport layer and / or electron transport layer material plays a role of efficiently transferring electrons and holes separated in the photoactive layer to the electrode, and the material is not particularly limited.
  • the hole transport layer material may be PEDOT: PSS (Poly (3,4-ethylenediocythiophene) doped with poly (styrenesulfonic acid)), molybdenum oxide (MoO x ); Vanadium oxide (V 2 O 5 ); Nickel oxide (NiO); Tungsten oxide (WO x ), and the like, but is not limited thereto.
  • PSS Poly (3,4-ethylenediocythiophene) doped with poly (styrenesulfonic acid)
  • MoO x molybdenum oxide
  • V 2 O 5 Vanadium oxide
  • NiO Nickel oxide
  • WO x Tungsten oxide
  • the electron transport layer material may be electron-extracting metal oxides, specifically, a metal complex of 8-hydroxyquinoline; Complexes including Alq 3 ; Metal complexes including Liq; LiF; Ca; Titanium oxide (TiO x ); Zinc oxide (ZnO); And cesium carbonate (Cs 2 CO 3 ), and the like, but is not limited thereto.
  • metal oxides specifically, a metal complex of 8-hydroxyquinoline; Complexes including Alq 3 ; Metal complexes including Liq; LiF; Ca; Titanium oxide (TiO x ); Zinc oxide (ZnO); And cesium carbonate (Cs 2 CO 3 ), and the like, but is not limited thereto.
  • the photoactive layer may be formed by dissolving a photoactive material, such as an electron donor and / or an electron acceptor, in an organic solvent and then spin coating, dip coating, screen printing, spray coating, doctor blade, brush painting, or the like. It is not limited to the method.
  • a photoactive material such as an electron donor and / or an electron acceptor
  • 2,4-hexadien-1-ol (2,4-Hexadien-1-ol (1.96 g, 20.0 mmol)) was dissolved in 80 mL of anhydrous tetrahydrofuran (anhydrous THF), and then 10 mL of benzoyl chloride, Triethylamine (5mL) was added thereto and stirred at room temperature for 5 hours. Distilled water and ethyl ether were added to separate the layers, and the organic layer was extracted.
  • anhydrous tetrahydrofuran anhydrous tetrahydrofuran
  • n-1 of Formula 1-1-2 was used in the same manner, except that Formula 1-B-2 (1.4 g, 6.92 mmol) was used instead of Formula 1-A-1. 0.56 g (8.8% yield) of a fullerene derivative was obtained.
  • the compound prepared in Preparation Example 1-1-1 and P3HT were dissolved in chlorobenzene (CB) at 1: 0.7 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.
  • the compound-P3HT 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 a vacuum of 3 ⁇ 10 ⁇ 8 torr.
  • the deposition produced an organic solar cell.
  • Example 1 using Formula 1-1-2 prepared in Preparation Example 1-1-2 instead of Formula 1-1-1 the ratio of P3HT and the fullerene derivative is 1: 1.
  • An organic solar cell was manufactured in the same manner as in Example 1-1.
  • Example 1 using Formula 1-1-3 prepared in Preparation Example 1-1-3 instead of Formula 1-1-1 the ratio of P3HT and the fullerene derivative is 1: 1.
  • An organic solar cell was manufactured in the same manner as in Example 1-1.
  • Example 1 using Formula 1-1-6 prepared in Preparation Example 1-1-6 instead of Formula 1-1-1 the ratio of P3HT and the fullerene derivative is 1: 1.
  • An organic solar cell was manufactured in the same manner as in Example 1-1.
  • Example 1 using Formula 1-1-7 prepared in Preparation Example 1-1-7 instead of Formula 1-1-1 the ratio of P3HT and the fullerene derivative is 1: 1.
  • An organic solar cell was manufactured in the same manner as in Example 1-1.
  • Example 1 using Formula 1-1-9 prepared in Preparation Example 1-1-9 instead of Formula 1-1-1 the ratio of P3HT and the fullerene derivative is 1: 1.
  • An organic solar cell was manufactured in the same manner as in Example 1-1.
  • Example 1-1 An organic solar cell was manufactured in the same manner as in Example 1-1, except that the polymer represented by Formula 1-2-1 and Formula 1-1-1 were 1: 0.7 in Example 1.
  • P3HT and PC 61 BM were dissolved in 1,2-dichlorobenzene (DCB) at 1: 0.7 to prepare a composite solution.
  • DCB 1,2-dichlorobenzene
  • the concentration was adjusted to 1.0 ⁇ 2.0 wt%
  • the organic solar cell was ITO / PEDOT: PSS / photoactive layer / LiF / Al structure.
  • 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, spin-coated, and then heat-treated at 120 ° C. for 5 minutes, using a thermal evaporator under 3 ⁇ 10 ⁇ 8 torr vacuum. LiF was deposited by 7 ⁇ and then Al was deposited to a thickness of 200 nm to prepare an organic solar cell.
  • 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.
  • P3HT and compound 1-2-1 are used as electron donor materials, the present invention is not limited thereto, and the compound is not limited to a polymer or a single molecule compound as long as the compound is capable of solution processing.
  • An embodiment according to an exemplary embodiment of the present specification provides an embodiment only with a device having a normal structure, but may be possible even with an inverted device.

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Abstract

La présente invention concerne un dispositif électronique organique comprenant des dérivés de fullerène.
PCT/KR2015/000202 2014-01-08 2015-01-08 Dérivés de fullerène et dispositif électronique organique les comprenant Ceased WO2015105354A1 (fr)

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CN201580003966.3A CN105899456B (zh) 2014-01-08 2015-01-08 富勒烯衍生物和包含富勒烯衍生物的有机电子器件
US15/110,308 US10693073B2 (en) 2014-01-08 2015-01-08 Fullerene derivatives and organic electronic device comprising fullerene derivatives
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US20030113940A1 (en) * 2001-07-16 2003-06-19 Erlanger Bernard F. Antibodies specific for nanotubes and related methods and compositions
KR101059783B1 (ko) * 2009-01-29 2011-08-26 한국화학연구원 플러렌 유도체를 함유한 유기박막트랜지스터
EP2445026A1 (fr) * 2009-06-18 2012-04-25 Sumitomo Chemical Company, Limited Elément de conversion photoélectrique organique
US8273599B2 (en) * 2006-12-01 2012-09-25 The Regents Of The University Of California Enhancing performance characteristics of organic semiconducting films by improved solution processing
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US20030113940A1 (en) * 2001-07-16 2003-06-19 Erlanger Bernard F. Antibodies specific for nanotubes and related methods and compositions
US20130306944A1 (en) * 2006-07-06 2013-11-21 Solenne Bv Blends of Fullerene Derivatives, and Uses Thereof in Electronic Devices
US8273599B2 (en) * 2006-12-01 2012-09-25 The Regents Of The University Of California Enhancing performance characteristics of organic semiconducting films by improved solution processing
KR101059783B1 (ko) * 2009-01-29 2011-08-26 한국화학연구원 플러렌 유도체를 함유한 유기박막트랜지스터
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