KR20150051577A - Copolymer and organic solar cell comprising the same - Google Patents
Copolymer and organic solar cell comprising the same Download PDFInfo
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- KR20150051577A KR20150051577A KR1020130133195A KR20130133195A KR20150051577A KR 20150051577 A KR20150051577 A KR 20150051577A KR 1020130133195 A KR1020130133195 A KR 1020130133195A KR 20130133195 A KR20130133195 A KR 20130133195A KR 20150051577 A KR20150051577 A KR 20150051577A
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- South Korea
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- copolymer
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- 238000005804 alkylation reaction Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005018 aryl alkenyl group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 1
- 125000006616 biphenylamine group Chemical group 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910021419 crystalline silicon Inorganic materials 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
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- 239000005416 organic matter Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
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- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
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- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000007781 pre-processing Methods 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
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- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
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- 238000012546 transfer Methods 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/124—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/04—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/04—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
- H01L31/042—PV modules or arrays of single PV cells
-
- 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
Abstract
The present invention provides a copolymer and an organic solar cell comprising the same.
Description
The present invention relates to copolymers and organic solar cells comprising the same.
Organic solar cells are devices that can convert solar energy directly into electric energy by applying photovoltaic effect. Solar cells can be divided into inorganic solar cells and organic solar cells depending on the material constituting the thin film. A typical solar cell is made of p-n junction by doping crystalline silicon (Si), which is an inorganic semiconductor. Electrons and holes generated by absorption of light are diffused to the p-n junction, accelerated by the electric field, and moved to the electrode. The power conversion efficiency of this process is defined as the ratio of the power given to the external circuit to the solar power entering the solar cell, and is achieved up to 24% when measured under the current standardized virtual solar irradiation conditions. However, since conventional inorganic solar cells have already been limited in economic efficiency and supply / demand of materials, organic semiconductor solar cells, which are easy to process, have various functions and are inexpensive, are seen as long-term alternative energy sources.
Solar cells are important to increase efficiency so that they can output as much electrical energy as possible from solar energy. In order to increase the efficiency of such a solar cell, it is also important to generate as much excitons as possible in the semiconductor, but it is also important to draw out generated charges without loss. One of the causes of loss of charge is that the generated electrons and holes are destroyed by recombination. Various methods have been proposed as methods for transferring generated electrons and holes to electrodes without loss, but most of them require additional processing, which may increase the manufacturing cost.
It is an object of the present invention to provide a copolymer and an organic solar cell including the same.
The present invention relates to a composition comprising a first unit represented by the following formula (1): A second unit represented by the following formula (2); And a third unit represented by the following formula (3).
[Chemical Formula 1]
(2)
(3)
In formulas (1) to (3)
X1 to X7 are the same or different and each independently selected from the group consisting of CRR ', NR, O, SiRR', PR, S, GeRR '
Y1 to Y4 are the same or different and each independently selected from the group consisting of CR, N, SiR, P and GeR,
R3, R4, R and R 'are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; Imide; Amide group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; And a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms.
The present disclosure relates to a plasma display panel comprising a first electrode; A second electrode facing the first electrode; And at least one organic material layer including a photoactive layer and disposed between the first electrode and the second electrode, wherein at least one of the organic material layers includes the copolymer.
The copolymer of the present invention can be used as a material for an organic solar cell organic material layer, and an organic solar cell including the same can exhibit excellent characteristics in terms of increase in open circuit voltage and short circuit current and / or increase in efficiency.
Copolymers according to one embodiment of the present disclosure may exhibit superior properties with deep HOMO levels, small bandgaps, and high charge mobilities. The polymer according to one embodiment of the present invention can be used alone or in combination with other materials in an organic solar cell, and can improve the efficiency and improve the lifetime characteristics of the device by the thermal stability of the compound.
1 is a view illustrating an organic solar cell according to an embodiment of the present invention.
Fig. 2 is a diagram showing the UV-Vis absorption spectrum of the
FIG. 3 is a graph showing a cyclic voltammetry of the
FIG. 4 shows the current density according to the voltage of the organic solar cell manufactured in Production Example 1. FIG.
5 shows the UV-Vis absorption spectrum of the
FIG. 6 is a graph showing a cyclic voltammetry result of the
FIG. 7 shows the current density according to the voltage of the organic solar cell manufactured in Production Example 2. FIG.
Hereinafter, the present invention will be described in detail.
As used herein, the term 'unit' means a repeating structure contained in a monomer of a copolymer, wherein the monomer is bonded to the copolymer by polymerization.
In this specification, the meaning of 'including unit' means that it is included in the main chain in the polymer.
In the present specification,
The copolymer according to one embodiment of the present invention includes a first unit represented by the formula (1), a second unit represented by the formula (2), and a third unit represented by the formula (3).
A first unit according to one embodiment of the present disclosure is a non-
In addition, there is no significant change in the electrochemical characteristics, that is, HOMO (highest occupied molecular orbital) or LUMO (lowest unoccupied molecular orbital) value, but the band gap is decreased and a larger amount of light can be absorbed, can do. therefore,
but,
in this case,
X is X1 or X3 in the formula (1).
Copolymers according to one embodiment of the present disclosure are random copolymers. In the case of the random copolymer, the crystallinity is reduced, the degree of amorphous is increased, the long-term stability to heat can be ensured, and the manufacturing process of the device and module including the copolymer becomes easy.
In addition, in the case of the random copolymer, the crystallinity is lower than that of the alternative copolymer, and the crystallinity is lowered depending on the use of the device, so that the lifetime of the device is not affected. Therefore, the organic solar cell including the random copolymer has an advantageous effect in stability and / or lifetime of the device.
In one embodiment of the present specification,
In one embodiment of the present invention,
As used herein, the term " substituted or unsubstituted " A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; Silyl group; An arylalkenyl group; An aryl group; An aryloxy group; An alkyloxy group; An alkylsulfoxy group; Arylsulfoxy group; Boron group; An alkylamine group; An aralkylamine group; An arylamine group; A heteroaryl group; Carbazole group; An arylamine group; An aryl group; A fluorenyl group; A nitrile group; A nitro group; Means a substituted or unsubstituted group selected from the group consisting of a hydroxyl group and a heterocyclic group containing at least one of N, O and S atoms.
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
In the present specification, the amide group may be mono- or di-substituted by nitrogen of the amide group with hydrogen, a straight-chain, branched-chain 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.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms 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- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, N-octyl, 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.
In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and specifically includes cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl, Do not.
In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.
In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms 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, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.
In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group, and includes a case where an alkyl group having 1 to 25 carbon atoms or an alkoxy group having 1 to 25 carbon atoms is substituted. In addition, an aryl group in the present specification may mean an aromatic ring.
When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25 carbon atoms. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, and a stilbenyl group.
When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 24 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.
In the present specification, a fluorenyl group is a structure in which two cyclic organic compounds are connected through one atom.
The fluorenyl group includes a structure of an open fluorenyl group, wherein the open fluorenyl group is a structure in which one ring compound is disconnected in a structure in which two ring organic compounds are connected through one atom.
When the fluorenyl group is substituted,
In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, But are not limited thereto.
In the present specification, the number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9- , A diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, and the like, but are not limited thereto.
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 or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.
Specific examples of the arylamine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methylphenylamine, 4-methyl-naphthylamine, 2-methyl- But are not limited to, cenylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, carbazole and triphenylamine groups.
In the present specification, the heterocyclic group is a heterocyclic group containing at least one of O, N and S as a heteroatom. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolyl group, A benzothiazole group, a benzothiazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline group, a thiazolyl group, a thiazolyl group, An isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.
In the present specification, the aryl group in the aryloxy group, arylthioxy group, arylsulfoxy group and aralkylamine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, Naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy, 2-anthryl Phenanthryloxy, 9-phenanthryloxy and the like. Examples of the arylthioxy group include phenylthio group, 2-methylphenylthio group, 4-tert-butylphenyl And the like. Examples of the aryl sulfoxy group include a benzene sulfoxy group and a p-toluenesulfoxy group, but the present invention is not limited thereto.
In the present specification, the heteroaryl group in the heteroarylamine group can be selected from the examples of the above-mentioned heterocyclic group.
In the present specification, the alkyl group in the alkylthio group and the alkylsulfoxy group is the same as the alkyl group described above. Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group. Examples of the alkylsulfoxy group include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, But are not limited thereto.
In one embodiment of the present disclosure, X1 is S.
In one embodiment of the present disclosure, X2 is S.
In one embodiment of the present disclosure, Y1 is N.
In one embodiment of the present disclosure, Y2 is N.
In one embodiment of the present disclosure, X3 is S.
In one embodiment of the present invention, the first unit represented by
[Formula 1-1]
In Formula 1-1,
R1 and R2 are the same as defined above.
In one embodiment of the present disclosure, X4 is S.
In one embodiment of the present disclosure, X5 is S.
In one embodiment of the present disclosure, Y3 is CR.
In one embodiment of the present disclosure, Y4 is CR.
In one embodiment of the present specification, R is a substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms.
In one embodiment of the present invention, the second unit represented by the general formula (2) is represented by the following general formula (2-1).
[Formula 2-1]
In formula (2-1)
R3 and R4 are the same as defined above,
R8 and R9 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; Imide; Amide group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; And a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms.
In one embodiment of the present invention, R8 and R9 are the same or different and each independently represents a substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms.
In one embodiment of the present invention, R8 and R9 are the same or different and each independently represents a substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted thiophene group.
In one embodiment of the present invention, the second unit represented by the formula (2) is represented by the following formula (2-2) or (2-3).
[Formula 2-2]
[Formula 2-3]
In formulas (2-2) and (2-3)
R11, R12, R15 and R16 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; Imide; Amide group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; And a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms.
In one embodiment of the present disclosure, X6 is NR.
In one embodiment of the present disclosure, R is a substituted or unsubstituted alkyl group.
In one embodiment of the present disclosure, R is a dodecanyl group.
In one embodiment of the present disclosure, X7 is S.
In one embodiment of the present invention, the third unit represented by the general formula (3) is represented by the following general formula (3-1).
[Formula 3-1]
In the formula (3-1)
R10 is hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; Imide; Amide group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; And a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms.
In one embodiment of the present invention, the copolymer includes a unit represented by the following formula (4).
[Chemical Formula 4]
In Formula 4,
A is a first unit represented by the formula (1)
B and B 'are the same or different and are each independently a second unit represented by the general formula (2)
C is a third unit represented by the formula (3)
x is a molar fraction, 0 < x < 1,
y is a mole fraction, 0 < y < 1,
x + y = 1,
and n is an integer of 1 to 10,000.
In one embodiment of the present specification, the copolymer comprises the following structural formula (5) or (6):
[Chemical Formula 5]
[Chemical Formula 6]
In formulas (5) and (6)
x is a molar fraction, 0 < x < 1,
y is a mole fraction, 0 < y < 1,
x + y = 1,
n is an integer from 1 to 10,000,
X1 to X7, X4 'and X5' are the same or different from each other and are independently selected from the group consisting of CRR ', NR, O, SiRR', PR, S, GeRR '
Y1 and Y2 are the same or different and independently selected from the group consisting of CR, N, SiR, P and GeR,
R11 to R18, R and R 'are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; Imide; Amide group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; And a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms.
In one embodiment of the present invention, R11 to R18 are the same or different and each independently a substituted or unsubstituted alkyl group.
In one embodiment of the present invention, R11 to R18 are the same or different and each independently represents a substituted or unsubstituted straight or branched alkyl group.
In one embodiment of the present specification, R11 is a substituted or unsubstituted alkyl group.
In one embodiment of the present specification, R11 is a hexyl group.
In one embodiment of the present specification, R12 is a substituted or unsubstituted alkyl group.
In one embodiment of the present disclosure, R12 is a hexyl group.
In one embodiment of the present specification, R13 is a substituted or unsubstituted alkyl group.
In one embodiment of the present disclosure, R13 is a hexyl group.
In one embodiment of the present specification, R14 is a substituted or unsubstituted alkyl group.
In one embodiment of the present disclosure, R14 is a hexyl group.
In one embodiment of the present specification, R15 is a substituted or unsubstituted alkyl group.
In one embodiment of the present specification, R15 is a substituted or unsubstituted branched alkyl group.
In one embodiment of the present disclosure, R15 is an ethylhexyl group.
In one embodiment of the present specification, R16 is a substituted or unsubstituted branched alkyl group.
In one embodiment of the present disclosure, R16 is an ethylhexyl group.
In one embodiment of the present specification, R17 is a substituted or unsubstituted branched alkyl group.
In one embodiment of the present disclosure, R17 is an ethylhexyl group.
In one embodiment of the present specification, R18 is a substituted or unsubstituted branched alkyl group.
In one embodiment of the present specification, R18 is an ethylhexyl group.
In one embodiment of the present disclosure, the copolymer comprises the following
[Copolymer 1]
[Copolymer 2]
x is a molar fraction, 0 < x < 1,
y is a mole fraction, 0 < y < 1,
x + y = 1,
and n is an integer of 1 to 10,000.
In one embodiment of the present disclosure, x is 0.5.
In one embodiment of the present disclosure, y is 0.5.
In one embodiment of the present invention, the terminal group of the copolymer is a heterocyclic group or an aryl group.
In one embodiment of the present invention, the terminal group of the copolymer is a 4- (trifluoromethyl) phenyl group.
According to one embodiment of the present disclosure, the number average molecular weight of the copolymer is preferably from 500 g / mol to 1,000,000 g / mol. Preferably, the number average molecular weight of the copolymer is 10,000 to 100,000. In one embodiment of the present disclosure, the number average molecular weight of the copolymer is from 30,000 to 100,000.
According to one embodiment of the present disclosure, the copolymer may have a molecular weight distribution of from 1 to 100. Preferably, the copolymer has a molecular weight distribution of from 1 to 3.
The lower the molecular weight distribution and the higher the number average molecular weight, the better the electrical and mechanical properties.
In addition, the number-average molecular weight is preferably 100,000 or less in order to have a solubility of more than a certain level and to be advantageous in application of a solution coating method.
The copolymers according to the present disclosure can be prepared by a multistage chemical reaction. The monomers may be prepared through alkylation, Grignard reaction, Suzuki coupling reaction, and Stille coupling reaction, followed by carbon-carbon coupling reaction such as a steel coupling reaction, Lt; / RTI > When the substituent to be introduced is a boronic acid or a boronic ester compound, it can be prepared through a Suzuki coupling reaction. When the substituent to be introduced is a tributyltin compound, But it is not limited thereto.
In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And at least one organic material layer including a photoactive layer and disposed between the first electrode and the second electrode, wherein at least one of the organic material layers includes the copolymer.
An organic solar cell according to an embodiment of the present invention includes a first electrode, a photoactive layer, and a second electrode. The organic solar cell may further include a substrate, a hole transporting layer, and / or an electron transporting layer.
In one embodiment of the present invention, when the organic solar cell receives photons from an external light source, electrons and holes are generated between the electron beams and the electron acceptors. The generated holes are transported to the anode through the electron donor layer.
In one embodiment of the present invention, the organic material layer includes a hole transport layer, a hole injection layer, or a layer that simultaneously transports holes and holes, and the hole transport layer, the hole injection layer, The layer comprising said copolymer.
In another embodiment, the organic material layer may include an electron injection layer, an electron transport layer, or a layer that simultaneously performs electron injection and electron transport, and the electron injection layer, the electron transport layer, And the copolymer.
20 is a view illustrating an organic solar cell according to an embodiment of the present invention.
In one embodiment of the present invention, when the organic solar cell receives photons from an external light source, electrons and holes are generated between the electron beams and the electron acceptors. The generated holes are transported to the anode through the electron donor layer.
In one embodiment of the present disclosure, the organic solar cell may further include an additional organic layer. The organic solar cell can reduce the number of organic layers by using organic materials having various functions at the same time.
In one embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode. In another embodiment, the first electrode is a cathode and the second electrode is an anode.
In one embodiment of the present disclosure, the organic solar cell may be arranged in the order of the cathode, the photoactive layer, and the anode, and may be arranged in the order of the anode, the photoactive layer, and the cathode, but is not limited thereto.
In another embodiment, the organic solar cell may be arranged in the order of an anode, a hole transporting layer, a photoactive layer, an electron transporting layer and a cathode, and may be arranged in the order of a cathode, an electron transporting layer, a photoactive layer, a hole transporting layer, , But is not limited thereto.
In one embodiment of the present invention, the organic solar cell is a normal structure.
In one embodiment of the present invention, the organic solar cell is an inverted structure.
In one embodiment of the present invention, the organic solar cell is a tandem structure.
The organic solar cell according to one embodiment of the present disclosure may have one photoactive layer or two or more layers.
In another embodiment, a buffer layer may be provided between the photoactive layer and the hole transporting layer or between the photoactive layer and the electron transporting layer. At this time, a hole injection layer may be further provided between the anode and the hole transport layer. Further, an electron injecting layer may be further provided between the cathode and the electron transporting layer.
In one embodiment of the present invention, the photoactive layer includes one or more selected from the group consisting of an electron donor and a donor, and the electron donor material includes the copolymer.
In one embodiment of the present disclosure, the electron acceptor material may be selected from the group consisting of fullerene, fullerene derivatives, vicoprofoins, semiconducting elements, semiconducting compounds, and combinations thereof. (6,6) -phenyl-C61-butyric acid-methylester) or PCBCR ((6,6) -phenyl-C61-butyric acid-cholesteryl ester), perylene perylene, polybenzimidazole (PBI), and 3,4,9,10-perylene-tetracarboxylic bis-benzimidazole (PTCBI).
In one embodiment of the present disclosure, the electron donor and the electron acceptor constitute a bulk heterojunction (BHJ). The electron donor material and the electron acceptor material are mixed in a ratio (w / w) of 1:10 to 10: 1.
Bulk heterojunction means that the electron donor material and the electron acceptor material are mixed in the photoactive layer.
In one embodiment of the present invention, the photoactive layer is a bilayer structure including an n-type organic layer and a p-type organic layer, and the p-type organic layer includes the copolymer.
In this 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 is not limited as long as it is a substrate commonly used in organic solar cells. Specific examples include glass or polyethylene terephthalate, polyethylene naphthalate (PEN), polypropylene (PP), polyimide (PI), and triacetyl cellulose (TAC) But is not limited thereto.
The anode electrode may be a transparent material having excellent conductivity, 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), and indium zinc oxide (IZO); ZnO: Al or SNO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.
The method of forming the anode electrode is not particularly limited and may be applied to one surface of the substrate or may be coated in a film form using, for example, sputtering, E-beam, thermal evaporation, spin coating, screen printing, inkjet printing, doctor blade or gravure printing . ≪ / RTI >
When the anode electrode is formed on a substrate, it may undergo cleaning, moisture removal and hydrophilic reforming processes.
For example, the patterned ITO substrate is sequentially washed with a detergent, acetone, and isopropyl alcohol (IPA), and then dried on a heating plate at 100 to 150 ° C for 1 to 30 minutes, preferably 120 ° C for 10 minutes , And the substrate surface is hydrophilically reformed when the substrate is completely cleaned.
Through such surface modification, the junction surface potential can be maintained at a level suitable for the surface potential of the photoactive layer. Further, in the modification, the formation of the polymer thin film on the anode electrode is facilitated, and the quality of the thin film may be improved.
The pretreatment techniques for the anode electrode include a) surface oxidation using a parallel plate discharge, b) a method of oxidizing the surface through ozone generated using UV ultraviolet radiation in vacuum, and c) oxygen generated by the plasma And a method of oxidizing using a radical.
One of the above methods can be selected depending on the state of the anode electrode or the substrate. However, whichever method is used, it is preferable to prevent oxygen from escaping from the surface of the anode electrode or the substrate and to suppress the residual of moisture and organic matter as much as possible. At this time, the substantial effect of the preprocessing can be maximized.
As a specific example, a method of oxidizing the surface through ozone generated using UV can be used. At this time, the ITO substrate patterned after the ultrasonic cleaning is baked on a hot plate, dried well, then put into a chamber, and is irradiated with ozone generated by reaction of oxygen gas with UV light by operating a UV lamp The patterned ITO substrate can be cleaned.
However, the method of modifying the surface of the patterned ITO substrate in the present specification is not particularly limited, and any method may be used as long as it is a method of oxidizing the substrate.
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; Layer structure such as LiF / Al, LiO 2 / Al, LiF / Fe, Al: Li, Al: BaF 2 and Al: BaF 2 : Ba.
The cathode electrode may be formed by depositing in a thermal evaporator having a degree of vacuum of 5 x 10 < -7 > torr or less, but the method is not limited thereto.
The hole transporting layer and / or the electron transporting layer material efficiently transfer electrons and holes separated from the photoactive layer to the electrode, and the material is not particularly limited.
The hole transport layer material may include poly (3,4-ethylenediocythiophene) doped with poly (styrenesulfonic acid) (PEDOT: PSS), molybdenum oxide (MoO x ); Vanadium oxide (V 2 O 5 ); Nickel oxide (NiO); And tungsten oxide (WO x ), but the present invention is not limited thereto.
The electron transport layer material may be electron-extracting metal oxides, specifically a metal complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Metal complexes including Liq; LiF; Ca; Titanium oxide (TiO x ); Zinc oxide (ZnO); And cesium carbonate (Cs 2 CO 3 ), but the present invention is not limited thereto.
The photoactive layer can be formed by dissolving a photoactive material such as an electron donor and / or an electron acceptor in an organic solvent, and then applying the solution by spin coating, dip coating, screen printing, spray coating, doctor blade, brush painting, But is not limited to the method.
The process for producing the copolymer and the production of the organic solar cell including the same will be described in detail in the following Production 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.
Example
1. Preparation of
In this specification, 4,7-bis (5-bromothiophen-2-yl) -5,6-bis (dodecyloxy) -benzo [c] [1,2,5] -thiadiazole , 7-bis (5-bromothiophene-2-yl) -5,6-bis (dodoecyloxy) -benzo [c] [1,2,5] -thiadiazole) was prepared by referring to the prior literature.
(Li, Yaowen; Chen, Yujin; Liu, Xing; Wang, Zhong; Yang, Xiaoming; Tu, Yingfeng; Zhu, Xiulin, Macromolecules, 2011, 44, 6370-6381)
Dibromo-5-dodecylthieno [3,4-c] pyrrole, such as 1,3-dibromo-5-dodecylthieno [3,4-c] -4,6-dione) was prepared by referring to the previous literature.
(Xugang Guo, Rocio Ponce Oitiz, Yan Zheng, Myung-Gil Kim, Shiming Zhang, Yan Hu, Gang Lu, Antonio Facchetti, and Tobin J. Marks, J. Am. Chem. Soc. 133, 2011, 13685-13697)
A microwave reactor vial was charged with 12 ml of chlorobenzene, 2,6-bis (trimethyltin) -4,8-di (2-ethylhexyloxybenzo [1,2-b: 4,5 4-di (2-ethylhexyloxybenzo [1,2-b: 4,5-b '] dithiphene, 0.600 g, 0.7769 mmol), 4 , 7-bis (5-bromothiophen-2-yl) -5,6-bis (dodecyloxy) -benzo [c] [1,2,5] -thiadiazole (0.3213 g, 0.3885 mmol), 1,3-dibromo-5-dodecyl 3-dibromo-5-dodecylthieno [3,4-c] pyrrole-4,6-dione 0.1861 g, 0.3885 mmol) Pd 2 (dba) 3 (Tris (dibenzylideneacetone) dipalladium (0), 10 mg) and tri- (o-tolyl) phosphine (80 mg) The mixture was cooled to room temperature, poured into methanol, and the solid was filtered to remove acetone, hexane and chloroform, and extracted with Soxhlet extractio n), and the chloroform portion was again precipitated in methanol to remove the solid.
Yield: 54%
Number average molecular weight: 27,500 g / mol
Weight average molecular weight: 49,826 g / mol
Fig. 2 shows a UV-Vis absorption spectrum on a film obtained by heat-treating a chlorobenzene solution of
The UV absorption spectrum of the film in FIG. 2 was obtained by dissolving the compound at a concentration of 1 wt% in chlorobenzene, dropping the solution on a glass substrate, and spin-coating the sample at 1000 rpm for 60 seconds at 125 °, 150 °, After heat treatment, it was analyzed by UV-Vis absorption spectrometer.
Fig. 3 shows the cyclic voltammetry of the
The measurement of the cyclic voltametry in FIG. 3 was performed by using a glassy carbon working electrode, an Ag / Agcl reference electrode, and a platinum (Pt) electrode in an electrolyte solution obtained by dissolving Bu 4 NBF 4 in acetonitrile at 0.1 M, Electrode was loaded and analyzed by three electrode method. The compound was coated on a working electrode by a drop casting method.
Example
2. Preparation of
A microwave reactor vial was charged with 15 ml of chlorobenzene, 20 ml of 2,6-bis (trimethyltin) -4,8-bis (5- (2-hexyl) thiophen- 1,2-b: 4,5-b '] 2,6-bis (trimethyltin) -4,8-bis (5- (2-hexyl) thiophene- -bis (4,5-b '] dithiphene, 0.500 g, 0.5893 mmol), 4,7-bis (5-bromothiophen- c] [1,2,5] -thiadiazole (4,7-bis (5-bromothiophene-2-yl) -5,6-bis (dodoecyloxy) -thiadiazole 0.2436 g, 0.2947 mmol), 1,3-dibromo-5-dodecylthieno [3,4-c] pyrrole-4,6-dione (1,3-dibromo-5-dodecylthieno [ , 4-c] pyrrole-4,6-dione 0.1412 g, 0.2947 mmol) Pd 2 (dba) 3 (Tris (dibenzylideneacetone) dipalladium (0), 10 mg) (o-tolyl) phosphine, 80 mg) was added thereto and reacted at 170 ° C for 1 hour. The mixture was cooled to room temperature, poured into methanol, and the solids were filtered. Soxhlet extraction was performed on acetone, hexane and chloroform, and the chloroform portion was again precipitated in methanol to remove solids.
Yield: 54%
Number average molecular weight: 21,055 g / mol
Weight average molecular weight: 40,826 g / mol
Fig. 5 shows a UV-Vis absorption spectrum of a film obtained by heat-treating a chlorobenzene solution of the
The UV absorption spectrum of the film in FIG. 5 was obtained by dissolving the compound in chlorobenzene at a concentration of 1 wt%, dropping the solution on a glass substrate, spin-coating the sample at 1000 rpm for 60 seconds, And analyzed using a UV-Vis absorption spectrometer.
6 shows a cyclic voltammetry result of the
The measurement of the cyclic voltametry in FIG. 6 was performed using a glassy carbon working electrode, an Ag / Agcl reference electrode, and a Pt (n-butyllithium) reference electrode in an electrolyte solution prepared by dissolving Bu 4 NBF 4 in acetonitrile Electrode was loaded and analyzed by three electrode method. The compound was coated on a working electrode by a drop casting method.
Preparation and characterization of organic solar cell
Manufacturing example 1. Manufacture of organic solar cell -1
Manufacturing example 2. Manufacture of organic solar cell -2
Comparative Example 1. Manufacture of organic solar cell
P3HT and PCBM were dissolved in 1,2-dichlorobenzene (DCB) at a ratio of 1: 1 to prepare a composite solution. At this time, the concentration was adjusted to 1.0 to 2.0 wt%, and the organic solar cell was made of ITO / PEDOT: PSS / photoactive layer / LiF / Al. The ITO-coated glass substrate was ultrasonically cleaned using distilled water, acetone, and 2-propanol, and the ITO surface was ozone-treated for 10 minutes and spin coated with PEDOT: PSS (baytrom P) Min. For the coating of the photoactive layer, the compound-PCBM composite solution was filtered with a 0.45 μm PP syringe filter, then spin-coated, and heat-treated at 120 ° C. for 5 minutes. Using a thermal evaporator under a vacuum of 3 × 10 -8 torr LiF was deposited to a thickness of 7 Å, and Al was deposited to a thickness of 200 nm to prepare an organic solar cell.
< Test Example 1>
The photoelectric conversion characteristics of the produced organic solar cells prepared in Production Example 1, Production Example 2 and Comparative Example 1 were measured under the conditions of 100 mW / cm 2 (AM 1.5), and the results are shown in Table 1 below.
In Table 1, the total thickness means the thickness of the active layer in the organic solar cell, Voc means open voltage, Jsc means short-circuit current, FF means fill factor, and PCE means energy conversion efficiency. The open-circuit voltage and the short-circuit current are the X-axis and Y-axis intercepts in the fourth quadrant of the voltage-current density curve, respectively. The higher the two values, the higher the efficiency of the solar cell. The fill factor is the width of the rectangle that can be drawn inside the curve divided by the product of the short-circuit current and the open-circuit voltage. The energy conversion efficiency can be obtained by dividing these three values by the intensity of the irradiated light, and a higher value is preferable.
FIG. 4 shows the current density according to the voltage of the organic solar cell manufactured in Production Example 1. FIG.
7 shows the current density according to the voltage of the organic solar cell manufactured in 2 in the production.
101: substrate
102: first electrode
103: Hole transport layer
104: photoactive layer
105: second electrode
Claims (17)
A second unit represented by the following formula (2); And
And a third unit represented by the following formula (3): < EMI ID =
[Chemical Formula 1]
(2)
(3)
In formulas (1) to (3)
X1 to X7 are the same or different and each independently selected from the group consisting of CRR ', NR, O, SiRR', PR, S, GeRR '
Y1 to Y4 are the same or different and each independently selected from the group consisting of CR, N, SiR, P and GeR,
R 1 and R 2 are the same or different and are each independently a substituent which increases the solubility,
R3, R4, R and R 'are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; Imide; Amide group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; And a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms.
R 1 and R 2 are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 40 carbon atoms, a substituted or unsubstituted thiol group, A substituted thio group, or a hydroxy group.
Wherein the first unit represented by the formula (1) is represented by the following formula (1-1):
[Formula 1-1]
In Formula 1-1,
R1 and R2 are the same as defined in claim 1.
Wherein the second unit represented by the formula (2) is represented by the following formula (2-1):
[Formula 2-1]
In formula (2-1)
R3 and R4 are the same as defined in claim 1,
R8 and R9 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; Imide; Amide group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; And a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms.
Wherein the third unit represented by the formula (3) is represented by the following formula (3-1):
[Formula 3-1]
In the formula (3-1)
R10 is hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; Imide; Amide group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; And a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms.
Wherein the copolymer comprises a unit represented by the following formula (4): < EMI ID =
[Chemical Formula 4]
In Formula 4,
A is a first unit represented by the formula (1)
B and B 'are the same or different and are each independently a second unit represented by the general formula (2)
C is a third unit represented by the formula (3)
x is a molar fraction, 0 < x < 1,
y is a mole fraction, 0 < y < 1,
x + y = 1,
and n is an integer of 1 to 10,000.
Wherein the copolymer comprises the following formula (5) or (6):
[Chemical Formula 5]
[Chemical Formula 6]
In formulas (5) and (6)
x is a molar fraction, 0 < x < 1,
y is a mole fraction, 0 < y < 1,
x + y = 1,
n is an integer from 1 to 10,000,
X1 to X7, X4 'and X5' are the same or different from each other and are independently selected from the group consisting of CRR ', NR, O, SiRR', PR, S, GeRR '
Y1 and Y2 are the same or different and independently selected from the group consisting of CR, N, SiR, P and GeR,
R 1 and R 2 are the same or different and are each independently a substituent which increases the solubility,
R11 to R18, R and R 'are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; Imide; Amide group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; And a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms.
Wherein the copolymer is a random copolymer.
Wherein the number average molecular weight of the copolymer is from 500 g / mol to 1,000,000 g / mol.
Wherein the copolymer has a molecular weight distribution of 1 to 100.
Wherein the organic material layer includes a hole transporting layer, a hole injecting layer, or a layer simultaneously transporting holes and injecting holes,
Wherein the hole transport layer, the hole injection layer, or the layer simultaneously transporting the holes and the hole injection comprises the copolymer.
Wherein the organic material layer includes an electron injection layer, an electron transport layer, or a layer that simultaneously performs electron injection and electron transport,
Wherein the electron injecting layer, the electron transporting layer, or the layer simultaneously injecting electrons and transporting electrons comprises the copolymer.
Wherein the photoactive layer comprises one or more selected from the group consisting of an electron donor and an electron donor,
Wherein the electron donor comprises the copolymer.
Wherein the electron acceptor is selected from the group consisting of fullerene, a fullerene derivative, a carbon nanotube, a carbon nanotube derivative, a subcomplex, a semiconductor element, a semiconducting compound, and a combination thereof.
Wherein the electron donor and the electron acceptor constitute bulk heterojunction (BHJ).
The photoactive layer is a bilayer structure including an n-type organic layer and a p-type organic layer,
Wherein the p-type organic layer comprises the copolymer.
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| KR1020130133195A KR101676904B1 (en) | 2013-11-04 | 2013-11-04 | Copolymer and organic solar cell comprising the same |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3018160A4 (en) * | 2014-02-14 | 2017-01-04 | LG Chem, Ltd. | Copolymer and organic solar cell comprising same |
| KR20200087366A (en) * | 2019-01-10 | 2020-07-21 | 주식회사 엘지화학 | Polymer and organic electronic device comprising the same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20130040830A (en) | 2010-03-31 | 2013-04-24 | 막스-플랑크-게젤샤프트 츄어 푀르더룽 데어 비쎈샤프텐 에.파우. | Annealed dithiophene copolymers |
| JP5779231B2 (en) * | 2011-03-11 | 2015-09-16 | 株式会社クラレ | π-electron conjugated block copolymer and photoelectric conversion device |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3018160A4 (en) * | 2014-02-14 | 2017-01-04 | LG Chem, Ltd. | Copolymer and organic solar cell comprising same |
| US9660194B2 (en) | 2014-02-14 | 2017-05-23 | Lg Chem, Ltd. | Copolymer and organic solar cell comprising same |
| KR20200087366A (en) * | 2019-01-10 | 2020-07-21 | 주식회사 엘지화학 | Polymer and organic electronic device comprising the same |
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| KR101676904B1 (en) | 2016-11-29 |
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