KR20160050223A - Benzothiadiazole derivatives and Solar cell device using this material - Google Patents
Benzothiadiazole derivatives and Solar cell device using this material Download PDFInfo
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- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical class C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 239000000463 material Substances 0.000 title abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 239000000126 substance Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052711 selenium Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 5
- UELITFHSCLAHKR-UHFFFAOYSA-N acibenzolar-S-methyl Chemical compound CSC(=O)C1=CC=CC2=C1SN=N2 UELITFHSCLAHKR-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- VLWABAVCKJCYBJ-UHFFFAOYSA-N 1,3-benzothiazole;1h-pyrazole Chemical class C=1C=NNC=1.C1=CC=C2SC=NC2=C1 VLWABAVCKJCYBJ-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000004065 semiconductor Substances 0.000 abstract description 11
- 230000003647 oxidation Effects 0.000 abstract description 6
- 238000007254 oxidation reaction Methods 0.000 abstract description 6
- 239000005964 Acibenzolar-S-methyl Substances 0.000 abstract description 2
- 229910052782 aluminium Inorganic materials 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 7
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 5
- 229910052788 barium Inorganic materials 0.000 description 4
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000007646 gravure printing Methods 0.000 description 3
- 238000007641 inkjet printing Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- -1 poly (para-phenylene vinylene) Polymers 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 229920003169 water-soluble polymer Polymers 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- OYLGJCQECKOTOL-UHFFFAOYSA-L barium fluoride Chemical compound [F-].[F-].[Ba+2] OYLGJCQECKOTOL-UHFFFAOYSA-L 0.000 description 2
- 229910001632 barium fluoride Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- SKRWFPLZQAAQSU-UHFFFAOYSA-N stibanylidynetin;hydrate Chemical compound O.[Sn].[Sb] SKRWFPLZQAAQSU-UHFFFAOYSA-N 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- LXOFYPKXCSULTL-UHFFFAOYSA-N 2,4,7,9-tetramethyldec-5-yne-4,7-diol Chemical group CC(C)CC(C)(O)C#CC(C)(O)CC(C)C LXOFYPKXCSULTL-UHFFFAOYSA-N 0.000 description 1
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 229910005191 Ga 2 O 3 Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene 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
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/14—Thiadiazoles; Hydrogenated thiadiazoles condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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Abstract
Description
본 발명은 벤조싸이아다이아졸 유도체 및 이를 이용한 유기태양전지에 관한 것이다. 보다 상세하게는 분자내 전자 당김체인 벤조싸이아다이아졸을 포함하는 유기 반도체 화합물 및 이를 이용한 유기태양전지에 관한 것이다.The present invention relates to benzothiadiazole derivatives and organic solar cells using the same. And more particularly, to an organic semiconductor compound containing a benzothiazole as an electron withdrawing group in a molecule and an organic solar cell using the same.
태양전지는 빛에너지를 전기에너지로 직접 변환시켜 주는 소자이다. 이들은 다양한 종류의 재료로 만들어지고 있으나 현재 가장 많이 사용되고 있는 재료는 단결정 Si이다. 그러나 단결정 Si 태양광전지는 제조단가를 더 이상 낮출 수 없는 문제와 생산 및 응용등에 제한이 있어, 최근 들어서는 박막 형태의 태양전지의 개발이 활발히 이루어지고 있다. 이중 유기태양전지는 유연하고 대면적화 할 수 있으며, 가볍고, 값싸게 제작 할 수 있는 장점을 가지고 있어, 이 분야에 많은 연구가 진행되고 있다. 유기태양전지는 크게 양 전극과 광활성층으로 이루어져 있다. 광활성층은 다시 전자 주게 소재와 전자 받게 소재로 구분 할 수 있으며, 전자 주게 소재는 단분자와 고분자로 나뉜다. 단분자 소재의 경우 phthalocyanine계 CuPc, ZnPc 등을 열증착을 통해 차례대로 쌓는 방법으로 제작 되고 있다. 반면 고분자는 PPV (poly(para-phenylene vinylene)), PF (polyfluorene) 계열 물질들이 대표적으로 쓰이고 최근에는 전자주게/받게를 교대로 중합하여 PFDTBT, PCPDTBT 같은 낮은 밴드갭 에너지를 갖는 공중합체 소재들이 연구되고 있으며, 고분자는 단분자 소재와 달리 스핀 코팅, 잉크젯 방식, gravure 인쇄방식 등을 이용하고 있어 상온 공정이 가능하며 간편하게 소자를 제작 할 수 있다.Solar cells are devices that directly convert light energy into electrical energy. They are made of various kinds of materials, but the most widely used material is monocrystalline Si. However, monocrystalline Si solar photovoltaic cells are limited in their production cost and manufacturing cost because they can no longer lower the production cost, and thin film solar cells have been actively developed recently. The dual organic solar cell has advantages such as being flexible, large-sized, light, and inexpensive, and so much research is being conducted in this field. Organic solar cells consist largely of both electrodes and photoactive layer. The photoactive layer can be divided into an electron-emitting material and an electron-receiving material. The electron-emitting material is divided into a single molecule and a polymer. In the case of monomolecular materials, phthalocyanine based CuPc and ZnPc are stacked one after another by thermal deposition. On the other hand, polymers are typically used for PPV (poly (para-phenylene vinylene)) and PF (polyfluorene) materials. In recent years, copolymer materials having low band gap energy such as PFDTBT and PCPDTBT have been studied by alternately polymerizing electron acceptors / Unlike single-molecule materials, polymers use spin coating, ink-jet printing, and gravure printing. They can be easily processed at room temperature.
상기 고분자를 이용한 유기태양전지의 원리는 전자 주게 소재인 고분자가 빛을 흡수하여 엑시톤 (exciton)을 형성하고 엑시톤이 전자 주게/받게 계면에서 분리가 일어나며, 이는 전자와 정공으로 나뉜다. 분리된 전자와 정공은 각각의 전극으로 이동하여 전기를 생산한다. The principle of an organic solar cell using the polymer is that a polymer as an electron-donating material absorbs light to form an exciton, and excitons are separated at an electron-accepting / receiving interface, which is divided into an electron and a hole. The separated electrons and holes move to the respective electrodes to produce electricity.
즉 낮은 밴드갭 에너지를 갖는 소재 개발을 위해 고분자의 방향성을 유지하고, 컨쥬게이션 길이를 늘리는 등의 연구가 진행되고 있으며, 이러한 일례로 한국공개특허공보 제 2011-0098303를 들 수 있다. 그러나 여전히 산화 안정성이 높고 고효율화를 위한 소재의 연구가 요구되고 있는 실정이다.In other words, in order to develop a material having a low band gap energy, studies are underway to maintain the orientation of the polymer and to increase the conjugation length, for example, Korean Patent Publication No. 2011-0098303. However, it is still required to study the material for high oxidation stability and high efficiency.
이에 본 발명자들은 전자 당김체인 벤조싸이아다이아졸을 포함하여, 산화안정성이 우수하고, 전자 이동 특성이 우수한 유기 반도체 화합물과 이를 이용한 고효율의 유기태양전지를 개발하고 본 발명을 완성하였다.Accordingly, the present inventors have developed an organic semiconductor compound having excellent oxidation stability and electron transfer characteristics, including a benzothiazole as an electron withdrawing group, and a highly efficient organic solar cell using the organic semiconductor compound and completed the present invention.
본 발명의 목적은 분자 내 전자 주게인 벤조싸이아다이아졸을 가짐으로써, 산화 안정성이 우수하고, 전기적 특성이 우수한 유기 반도체 화합물 및 이를 광활성층 재료로 도입한 유기태양전지를 제공하는 것이다.An object of the present invention is to provide an organic semiconductor compound excellent in oxidation stability and excellent in electrical characteristics by having a benzothiazole as an electron donor in a molecule and an organic solar cell into which the organic semiconductor compound is introduced as a photoactive layer material.
본 발명은 하기 화학식 1로 표시되는 벤조싸이아다이아졸 유도체를 포함한다.The present invention includes benzothiadiazole derivatives represented by the following formula (1).
[화학식 1][Chemical Formula 1]
[상기 화학식 1에서,[In the above formula (1)
상기 V1 및 V2는 각각 독립적으로 수소, 
상기 L1은 단일결합, 
상기 R1, R2, R3 및 R4는 각각 독립적으로 수소, 불소, (C1-C30)알킬, (C1-C30)알콕시 또는 (C1-C30)알킬티오이다.]Each of R 1, R 2, R 3 and R 4 is independently hydrogen, fluorine, (C 1 -C 30) alkyl, (C 1 -C 30) alkoxy or (C 1 -C 30)
본 발명의 일 실시예에 따른 벤조싸이아다이아졸 유도체는 하기 화합물에서 선택될 수 있다.The benzothiadiazole derivatives according to one embodiment of the present invention can be selected from the following compounds.
본 발명은 상기 벤조싸이아다이아졸 유도체를 포함하는 유기전자소자를 제공한다.The present invention provides an organic electronic device comprising the benzothiadiazole derivative.
본 발명의 일 실시예에 따른 상기 유기전자소자는 유기발광소자, 유기태양전지, 유기트랜지스터, 유기 메모리 또는 유기감광체(OPC)일 수 있다.The organic electronic device according to an exemplary embodiment of the present invention may be an organic light emitting device, an organic solar cell, an organic transistor, an organic memory, or an organic photoconductor (OPC).
본 발명에 따른 화합물은 전자 주게인 벤조싸이아다이아졸을 가짐으로써, 낮은 에너지 밴드갭과 낮은 구동 전압을 가질 뿐 아니라 열에 대한 안정성을 가지며, 이를 채용한 유기전자소자는 높은 전자 밀도로 인해 높은 단락 전류(Jsc)를 가져, 우수한 효율과 장수명 특성을 가질 수 있다. The compound according to the present invention has a low energy band gap and low driving voltage as well as heat stability by having electron-donating benzothiadiazole, and the organic electronic device employing it has high short circuit due to high electron density Current (Jsc), and can have excellent efficiency and long-life characteristics.
본 발명은 높은 전하 이동도, 높은 전자 밀도 및 높은 용해도를 가지는 하기 화학식 1로 표시되는 신규한 유기 반도체 화합물 및 이를 이용한 유기태양전지에 관한 것으로, 본 발명에 따른 유기 반도체 화합물은 용해도가 높아 간편한 용액 공정이 가능하며, 이를 채용한 유기태양전지는 높은 전자 이동도에 의한 높은 단락 전류(Jsc)를 가져 고효율 특성을 가질 수 있으며, 산화안정성이 우수하고, 개방전압(Voc)을 향상시킬 수 있는 특징이 있다. The present invention relates to a novel organic semiconductor compound represented by the following general formula (1) having high charge mobility, high electron density and high solubility, and an organic solar cell using the same. The organic semiconductor compound according to the present invention has high solubility, The organic solar cell employing the organic solar cell can have a high short-circuit current (Jsc) due to high electron mobility and can have a high efficiency characteristic, and is excellent in oxidation stability and can improve the open-circuit voltage (Voc) .
[화학식 1][Chemical Formula 1]
[상기 화학식 1에서,[In the above formula (1)
상기 V1 및 V2는 각각 독립적으로 수소, 
상기 L1은 단일결합, 
상기 R1, R2, R3 및 R4는 각각 독립적으로 수소, 불소, (C1-C30)알킬, (C1-C30)알콕시 또는 (C1-C30)알킬티오이다.]Each of R 1, R 2, R 3 and R 4 is independently hydrogen, fluorine, (C 1 -C 30) alkyl, (C 1 -C 30) alkoxy or (C 1 -C 30)
본 발명의 일 실시예에 따른 벤조싸이아다이아졸 유도체는 하기 구조에서 선택될 수 있으나 이에 한정되는 것은 아니다.The benzothiadiazole derivatives according to an embodiment of the present invention may be selected from the following structures, but are not limited thereto.
또한 본 발명은 상기 벤조싸이아다이아졸 유도체를 포함하는 유기태양전지를 포함한다. 보다 바람직하게는 본 발명에 따른 상기 벤조싸이아다이아졸 유도체를 유기태양전지의 활성층에 포함할 수 있다. The present invention also includes an organic solar cell comprising the benzothiadiazole derivative. More preferably, the benzothiadiazole derivative according to the present invention can be incorporated into an active layer of an organic solar cell.
일반적으로 본 발명에 따른 유기태양전지는 이하 상술하는 방법으로 제조될 수 있으나 이는 일례를 들어 설명하는 것으로 이에 한정이 있는 것은 아니다.In general, the organic solar cell according to the present invention can be manufactured by the method described below, but the present invention is not limited thereto.
본 발명의 바람직한 실시예에 따라 제조된 유기태양전지는 기판, 제1전극, 정공수송층, 활성층, 전자수송층 및 제2전극으로 이루어진다. An organic solar cell manufactured according to a preferred embodiment of the present invention comprises a substrate, a first electrode, a hole transporting layer, an active layer, an electron transporting layer, and a second electrode.
상기 기판은 유리 및 석영판 이외에도 PET(polyethylene terephthalate), PEN(polyethylene naphthelate), PP(polyperopylene), PI(polyimide), PC(polycarbornate), PS(polystylene), POM(polyoxyethlene), AS 수지(acrylonitrile styrene copolymer), ABS 수지(acrylonitrile butadiene styrene copolymer) 및 TAC(Triacetyl cellulose) 등을 포함하는 플라스틱과 같은 유연하고 투명한 물질로 제조될 수 있다. In addition to glass and quartz, the substrate may be made of a material selected from the group consisting of polyethylene terephthalate (PEN), polyperopylene (PEN), polyimide, polyimide, polycarbonate, polystyrene, polyoxyethylenes, such as plastics, including acrylonitrile butadiene styrene copolymer, ABS resin, and TAC (triacetyl cellulose).
또한 상기 제1 전극은 스퍼터링, E-Beam, 열증착, 스핀코팅, 스크린 프린팅, 잉크젯 프린팅, 닥터 블레이드 또는 그라비아 프린팅법을 사용하여 투명전극 물질을 상기 기판의 일면에 도포되거나 필름형태로 코팅됨으로써 형성된다. 제1 전극(120)은 애노드의 기능을 하는 부분으로써, 후술하는 제2 전극(160)에 비해 일함수가 큰 물질로 투명성 및 도전성을 갖는 임의의 물질이 사용될 수 있다. 예를 들면, ITO(indium tin oxide), 금, 은, 플로린이 도핑된 틴 옥사이드(fluorine doped tin oxide; FTO), 알루미늄이 도핑된 징크 옥사이드(aluminium doped zink oxide, AZO), IZO(indium zink oxide), ZnO-Ga2O3, ZnO-Al2O3 및 ATO(antimony tin oxide) 등이 있으며, 바람직하게는 ITO를 사용하는 것이 좋다.The first electrode may be formed by coating a transparent electrode material on one side of the substrate or by coating it with a film using sputtering, E-beam, thermal evaporation, spin coating, screen printing, inkjet printing, doctor blade or gravure printing do. The first electrode 120 functions as an anode and may be made of any material having a higher work function than the second electrode 160 and having transparency and conductivity. For example, there are known indium tin oxide (ITO), gold, silver, fluorine doped tin oxide (FTO), aluminum doped zink oxide (AZO), indium zinc oxide ), ZnO-Ga 2 O 3 , ZnO-Al 2 O 3 and ATO (antimony tin oxide), and it is preferable to use ITO.
상기 제1 전극의 상부에는 정공 수송층이 스핀코팅 또는 딥코팅 등의 방법을 통해 도입되는데, 본 발명에서는 전도성 고분자 용액으로서 폴리리(3,4-에틸렌디옥시티오펜):폴리(4-스티렌설포네이트)[PEDOT:PSS]를 사용하는 것이 바람직하다.A hole transport layer is introduced onto the first electrode through spin coating or dip coating. In the present invention, a poly (3,4-ethylenedioxythiophene): poly (4-styrenesulfonate ) [PEDOT: PSS] is preferably used.
또한 상기 활성층에는 본 발명에 따른 유기 반도체 화합물을 포함할 수 있으며, 이의 배합량은 용도에 따라 적절하게 조절될 수 있다. 또한 상기 유기 반도체 화합물은 유기 용매에 용해시켜, 60 내지 120nm 두께로 활성층에 도입될 수 있다. 이때, 상기 유기용매는 아세톤, 메탄올, THF, 톨루엔, 자일렌, 테트랄린, 클로로포름, 클로로벤젠, 디클로로벤젠 또는 이들의 혼합용매 일 수 있으나, 이에 한정되는 것은 아니다. 또한 본 발명에 따른 유기 반도체 화합물을 포함하는 상기 활성층은 높은 전자 밀도로 인하여, 단락전류밀도(short circuit current density) 및 개방전압(open circuit voltage)이 증가하여 에너지변환효율에 좋다. The active layer may contain the organic semiconductor compound according to the present invention, and the compounding amount thereof may be suitably adjusted according to the use. The organic semiconductor compound may be dissolved in an organic solvent and introduced into the active layer to a thickness of 60 to 120 nm. At this time, the organic solvent may be acetone, methanol, THF, toluene, xylene, tetralin, chloroform, chlorobenzene, dichlorobenzene or a mixture thereof, but is not limited thereto. In addition, the active layer including the organic semiconductor compound according to the present invention has good short-circuit current density and open circuit voltage due to its high electron density, which is good for energy conversion efficiency.
상기 전자수송층은 전자수송층의 모폴로지를 향상시키기 위해 계면활성제(surfactant)를 첨가하여 제조 할 수 있다. 이때, 상기 전자수송층은 친전자성 기능을 가지는 수용성 고분자를 물, 에탄올 또는 이들의 혼합용매에 용해하고, 상기 고분자 용액에 계면활성제를 첨가한 후 여과하여 박막을 형성하는 단계를 포함하여 제조할 수 있다. 이때, 상기 친전자성 기능기를 가지는 수용성 고분자로는 폴리[9,9-비스(6'-디에탄올아미노)헥실)-플루오렌]이 바람직하며, 상기 계면활성제는 2,4,7,9-테트라메틸-5-데킨-4,7-디올인 것이 바람직하지만, 이에 한정되는 것은 아니다. 또한 상기 수용성 고분자 및 계면활성제가 혼합된 용액을 스핀 코팅 등의 방법으로 2 내지 20nm 코팅하여 열처리하는 것이 좋다. 이때, 상기 전자수송층은 스핀코팅의 방법 외에도 딥코팅, 스크린 프린팅, 잉크젯 프린팅, 그라비아 프린팅, 스프레이 코팅, 닥터블레이드 또는 브러쉬 페인팅 등의 방법을 응용할 수 있으며, 본 발명이 이에 제한되는 것은 아니다.The electron transport layer may be prepared by adding a surfactant to improve the morphology of the electron transport layer. At this time, the electron transport layer may be prepared by dissolving a water-soluble polymer having an electrophilic function in water, ethanol or a mixed solvent thereof, adding a surfactant to the polymer solution, and then filtering to form a thin film have. As the water-soluble polymer having the electrophilic functional group, poly [9,9-bis (6'-diethanolamino) hexyl) -fluorene] is preferable, and the surfactant is 2,4,7,9- Tetramethyl-5-decyne-4,7-diol, but is not limited thereto. The solution mixed with the water-soluble polymer and the surfactant may be coated by 2 to 20 nm by a spin coating method and then heat-treated. At this time, the electron transport layer may be applied by dip coating, screen printing, inkjet printing, gravure printing, spray coating, doctor blade, brush painting or the like in addition to the spin coating method, but the present invention is not limited thereto.
또한 상기 제2 전극은 전자수송층이 도입된 상태에서 열증착기를 이용하여 증착될 수 있다. 이때 사용가능한 전극재료로는 불화리튬/알루미늄, 불화리튬/칼슘/알루미늄, 칼슘/알루미늄, 불화바륨/알루미늄, 불화바륨/바륨/알루미늄, 바륨/알루미늄, 알루미늄, 금, 은, 마스네슘:은 및 리튬:알루미늄 중에서 선택될 수 있으며, 바람직하게는 불화바륨/바륨/알루미늄 구조로 제작된 전극을 사용하는 것이 좋다.Also, the second electrode may be deposited using a thermal evaporator in a state in which an electron transport layer is introduced. The electrode material that can be used at this time includes lithium fluoride / aluminum, lithium fluoride / calcium / aluminum, calcium / aluminum, barium fluoride / aluminum, barium fluoride / barium / aluminum, barium / aluminum, aluminum, gold, silver, Lithium, and aluminum. Preferably, an electrode made of a barium / barium / aluminum structure is used.
Claims (4)
[화학식 1]
[상기 화학식 1에서,
상기 V1 및 V2는 각각 독립적으로 수소,
상기 L1은 단일결합,
상기 R1, R2, R3 및 R4는 각각 독립적으로 수소, 불소, (C1-C30)알킬, (C1-C30)알콕시 또는 (C1-C30)알킬티오이다.]A benzothiadiazole derivative represented by the following formula (1): < EMI ID =
[Chemical Formula 1]
[In the above formula (1)
V 1 and V 2 are each independently hydrogen,
L < 1 > is a single bond,
Each of R 1, R 2, R 3 and R 4 is independently hydrogen, fluorine, (C 1 -C 30) alkyl, (C 1 -C 30) alkoxy or (C 1 -C 30)
하기 화합물에서 선택되는 것인 벤조싸이아다이아졸 유도체;
Benzothiadiazole derivatives wherein the benzothiadiazole derivative is selected from the following compounds;
상기 유기전자소자는 유기발광소자, 유기태양전지, 유기트랜지스터, 유기 메모리 또는 유기감광체(OPC)인 유기전자소자.The method of claim 3,
Wherein the organic electronic device is an organic light emitting device, an organic solar cell, an organic transistor, an organic memory or an organic photoconductor (OPC).
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| CN115028602A (en) * | 2022-08-09 | 2022-09-09 | 中国华能集团清洁能源技术研究院有限公司 | Star-shaped molecule for hole transport layer and preparation method and application thereof |
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| CN115028602A (en) * | 2022-08-09 | 2022-09-09 | 中国华能集团清洁能源技术研究院有限公司 | Star-shaped molecule for hole transport layer and preparation method and application thereof |
| CN115028602B (en) * | 2022-08-09 | 2022-11-15 | 中国华能集团清洁能源技术研究院有限公司 | Star-shaped molecule capable of being used for hole transport layer and preparation method and application thereof |
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