WO2014181986A1 - 플러렌 유도체를 포함하는 유기 전자 소자 - Google Patents
플러렌 유도체를 포함하는 유기 전자 소자 Download PDFInfo
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- WO2014181986A1 WO2014181986A1 PCT/KR2014/003706 KR2014003706W WO2014181986A1 WO 2014181986 A1 WO2014181986 A1 WO 2014181986A1 KR 2014003706 W KR2014003706 W KR 2014003706W WO 2014181986 A1 WO2014181986 A1 WO 2014181986A1
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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Definitions
- the present specification relates to a fullerene derivative and an organic electronic device including the same.
- An object of the present specification is to provide an organic electronic device comprising a fullerene derivative.
- the first electrode In one embodiment of the present specification, the first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode.
- At least one layer of the organic material layer provides an organic electronic device comprising a fullerene derivative represented by the following formula (1).
- n is an integer from 1 to 5
- Cn is C 60 to C 120 fullerene
- R1 to R6 are the same as or different from each other, and each independently hydrogen; Halogen group; Nitro group; Cyano group; Carboxylic acid groups; Hydroxyl group; Substituted or unsubstituted carbonyl group; Sulfo group (-SO 3 H); Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted ester group; Substituted or unsubstituted thioester group; Substituted or unsubstituted amide group; Substituted or unsubstituted ether group; Substituted or unsubstituted sulfone group; Substituted or unsubstituted alkylthioxy group; Substituted or un
- An organic electronic device including a fullerene derivative according to one embodiment of the present specification shows an increase in efficiency and / or a rise in safety.
- the organic electronic device including the fullerene derivative according to the exemplary embodiment of the present specification has excellent light efficiency, excellent thermal stability, and improved lifespan characteristics.
- FIG. 1 illustrates an organic solar cell according to an exemplary embodiment of the present specification.
- FIG. 7 is a diagram showing liquid chromatography (HPLC) in the structure of Chemical Formula 1-1-11 according to one embodiment of the present specification.
- R1 to R6 When at least one of R1 to R6 is an ester group, there is an effect of increasing solubility and / or storage stability. Therefore, there is an economical effect in time and / or cost in the manufacture of the organic electronic device.
- the arylalkyl group is not particularly limited in carbon number, but in one embodiment of the present specification, the arylalkyl group has 7 to 50 carbon atoms. Specifically, the aryl portion has 6 to 49 carbon atoms, and the alkyl portion has 1 to 44 carbon atoms.
- Z2 and Z3 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms containing at least one of N, O and S atoms.
- R1 to R6 are the same as or different from each other, and each independently hydrogen; Nitro group; Cyano group; Carboxylic acid groups; Substituted or unsubstituted carbonyl group; Sulfo groups; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted ester group; Substituted or unsubstituted sulfone group; Substituted or unsubstituted arylalkyl group, or adjacent substituents are bonded to each other, substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heteroring comprising at least one of N, O and S atoms.
- R7 is hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms; Heteroarylalkyl group having 2 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
- the hydrocarbon ring is a cycloalkyl group; Cycloalkenyl group; Aromatic ring groups; Or include all aliphatic ring groups, which may be monocyclic or polycyclic, and include all rings condensed by combining one or two or more.
- R7 is a methyl group.
- R7 is an alkyl group substituted with a hydroxy group.
- R7 is a pentafluoropropyl group.
- R7 is a heptadecafluorononyl group.
- R7 is an alkyl group substituted with fluorine.
- R7 is an alkyl group substituted with an alkenyl group.
- R7 is a substituted or unsubstituted aryl group.
- R7 is a phenyl group substituted with an alkyl group.
- R7 is a phenyl group substituted with a cyano group.
- R7 is a phenyl group substituted with an aldehyde group.
- R1 is a substituted or unsubstituted alkyl group.
- R1 is a pentyl group.
- R1 is an ester group substituted with an ethyl group.
- R1 is an ester group substituted with a butyl group.
- R1 is an ester group substituted with 1-methylheptyl group.
- R1 is an ester group substituted with a crown ether group.
- R1 is an ester group substituted with an alkyl group substituted with a substituted or unsubstituted heteroring group.
- R1 is an ester group substituted with an ethyl group substituted with a phenyl-thiophene group.
- R1 is an ester group substituted with a substituted or unsubstituted aryl group.
- R1 is an ester group substituted with a phenyl group substituted with a cyano group.
- R1 is an ester group substituted with a substituted or unsubstituted carbonyl group.
- R1 is a substituted or unsubstituted alkoxy group.
- R1 is a substituted or unsubstituted carbonyl group.
- R1 is a nitro group.
- R6 is an ester group substituted with a butyl group.
- R6 is an ester group substituted with an alkyl group substituted with a heterocyclic group.
- R6 is an ester group substituted with an alkyl group substituted with a hydroxy group.
- R6 is an ester group substituted with a substituted or unsubstituted arylalkyl group.
- R6 is an ester group substituted with a phenyl group substituted with a carbonyl group.
- R6 is a carbonyl group substituted with an alkyl group.
- R6 is an ester group substituted with an alkyl group substituted with an alkoxy group substituted with an alkoxy group.
- the structure in parentheses in the formula (1) is represented by any one of the following formula.
- R3 is a carboxylic acid group.
- R3 is an alkoxy group substituted with an ethyl group.
- R3 is an ester group substituted with an alkyl group.
- R3 is a substituted or unsubstituted alkoxy group.
- R3 is a substituted or unsubstituted arylalkyl group.
- R3 is a methyl group substituted with a phenyl group.
- R4 is a sulfo group.
- R4 is a carbonyl group substituted with a phenyl group.
- R4 is an alkoxy group substituted with a methyl group.
- R4 is a substituted or unsubstituted ester group.
- R4 is an ester group substituted with an alkyl group.
- R4 is an alkyl group substituted with a phenyl group.
- the structure in parentheses in the formula (1) is represented by any one of the following formula.
- n and Cn are the same as defined above.
- the fullerene derivative according to the exemplary embodiment of the present specification may further include another structure in addition to the structure in parentheses in Formula 1.
- the fullerene derivative represented by Chemical Formula 1 may be prepared by the reaction of a 1,3-diene compound derivative.
- the solvent is aliphatic hydrocarbons such as hexane and heptane; Aromatic hydrocarbons such as toluene, xylene, trimethylbenzene and methylnaphthalene; Ethers such as dibutyl ether, diethylene glycol diethyl ether, diethylene glycol dimethyl ether and tetrahydrofuran; Ketones such as acetone and 2-butanone; Alcohols such as methanol, ethanol, 2-propanol, t-butyl alcohol, methoxyethanol and diethylene glycol monomethyl ether; Esters such as ethyl acetate; Nitriles such as acetonitrile; Amides such as N, N-dimethylacetamide; halogenated hydrocarbons such as o-dichlorobenzene, methylene chloride and 1,2-dichloroethane; Amines such as pyridine and quinoline; It can select from water and can mix and use 1 or 2 or more.
- the organic electronic device may be an organic light emitting device.
- the organic material layer includes a light emitting layer, and the light emitting layer includes the fullerene derivative.
- the organic material layer includes a photoactive layer
- the photoactive layer includes an electron donor material and an electron acceptor material
- the electron acceptor material includes the fullerene derivative
- Bulk heterojunction means that the electron donor material and the electron acceptor material are mixed with each other in the photoactive layer.
- the organic compound included in the electron acceptor material is fullerene, fullerene derivative (PCBM ((6,6) -phenyl-C61-butyric acid-methylester) or PCBCR ((6, 6) -phenyl-C61-butyric acid-cholesteryl ester), perylene (perylene) PBI (polybenzimidazole), and PTCBI (3,4,9,10-perylene-tetracarboxylic bis-benzimidazole) 1 or Two or more compounds.
- PCBM ((6,6) -phenyl-C61-butyric acid-methylester) or PCBCR ((6, 6) -phenyl-C61-butyric acid-cholesteryl ester)
- perylene (perylene) PBI polybenzimidazole
- PTCBI 3,4,9,10-perylene-tetracarboxylic bis-benzimidazole
- an ester compound having a substituent such as an alkyl group containing a fluorine (F) group, an ethoxyalkyl group, a polyethyleneglycoloxyalkyl group, or a crown ether alkyl group.
- the substituent of the fullerene derivative is arranged toward the anode according to the surface energy of the fullerene derivative, and thus may serve as a buffer layer between the photoactive layer and the anode electrode. That is, according to one embodiment of the present specification, the fullerene derivative may simultaneously or independently serve as an electron acceptor role and / or a buffer layer.
- the organic solar cell may be arranged in order of an anode electrode, a buffer layer, a photoactive layer, and a cathode electrode.
- the anode electrode may be a transparent and excellent conductive material, but is not limited thereto.
- Metals such as vanadium, chromium, copper, zinc and gold or alloys thereof;
- Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO: Al or SNO 2 : Combination of metals and oxides such as Sb;
- Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
- the bonding surface potential can be maintained at a level suitable for the surface potential of the photoactive layer.
- the cathode electrode may be a metal having a small work function, but is not limited thereto.
- metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; LiF / Al, LiO 2 / Al, LiF / Fe, Al: Li, Al: BaF 2 , Al: BaF 2
- It may be a material of a multi-layer structure such as, but is not limited thereto.
- the hole transport layer material may be PEDOT: PSS (Poly (3,4-ethylenediocythiophene) doped with poly (styrenesulfonic acid)), molybdenum oxide (MoO x ); Vanadium oxide (V 2 O 5 ); Nickel oxide (NiO); Tungsten oxide (WO x ), and the like, but is not limited thereto.
- PSS Poly (3,4-ethylenediocythiophene) doped with poly (styrenesulfonic acid)
- MoO x molybdenum oxide
- V 2 O 5 Vanadium oxide
- NiO Nickel oxide
- WO x Tungsten oxide
- FIG. 6 is a diagram showing an NMR graph in the structure of Chemical Formula 1-1-11 according to an exemplary embodiment of the present specification.
- the compound prepared in Preparation Example 1-1-1 and P3HT were dissolved in chlorobenzene (CB) at 1: 0.7 to prepare a composite solution.
- CB chlorobenzene
- the concentration was adjusted to 2.0 wt%, and the organic solar cell had a structure of ITO / PEDOT: PSS / photoactive layer / Al.
- ITO-coated glass substrates were ultrasonically cleaned with distilled water, acetone and 2-propanol, ozonated the ITO surface for 10 minutes, and spin-coated PEDOT: PSS (baytrom P) to 45 nm to 10 at 120 Heat treated for minutes.
- thermal evaporator thermal evaporator
- compound under -P3HT combined solution was filtered through a 0.45 PP ⁇ m syringe filter (syringe filter), and then spin-coated, 3x10 -8 torr vacuum for Al to 200 nm thickness
- the deposition produced an organic solar cell.
- Example 1-1 using Formula 1-1-6 prepared in Preparation Example 1-1-6 instead of Formula 1-1-1 the ratio of P3HT and the fullerene derivative is 1: 1. Was manufactured in the same manner as in Example 1-1.
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Abstract
Description
활성층(P3HT : 화합물) | VOC(V) | JSC(mA/cm2) | FF | PCE(%) | |
비교예 1-1 | P3HT : PC61BM = 1:0.7 | 0.65 | 7.71 | 0.59 | 2.91 |
실시예 1-1 | P3HT : 화학식1-1-1 = 1:0.7 | 0.63 | 8.90 | 0.54 | 3.03 |
실시예 1-2 | P3HT] : 화학식1-1-2 = 1:1 | 0.60 | 7.41 | 0.62 | 2.76 |
실시예 1-3 | P3HT : 화학식1-1-3 = 1:1 | 0.63 | 4.46 | 0.37 | 1.04 |
실시예 1-4 | P3HT : 화학식1-1-4= 1:1 | 0.69 | 8.20 | 0.30 | 1.70 |
실시예 1-5 | P3HT : 화학식1-1-5 = 1:0.7 | 0.63 | 7.72 | 0.66 | 3.21 |
실시예 1-6 | P3HT : 화학식1-1-6 = 1:1 | 0.65 | 7.69 | 0.63 | 3.15 |
실시예 1-7 | P3HT : 화학식1-1-7 = 1:2 | 0.53 | 10.78 | 0.50 | 2.86 |
실시예 1-8 | P3HT : PC61BM: 화학식1-1-5 = 1: 0.7: 0.05 | 0.65 | 8.96 | 0.65 | 3.79 |
실시예 1-9 | P3HT : 화학식1-2-1 = 1:1 | 0.62 | 6.26 | 0.54 | 2.10 |
실시예 1-10 | P3HT : 화학식1-1-8 = 1:1 | 0.63 | 8.19 | 0.63 | 3.25 |
실시예 1-11 | P3HT : 화학식1-1-9 = 1:1 | 0.59 | 8.19 | 0.63 | 3.04 |
실시예 1-12 | P3HT : 화학식1-1-10 = 1:1 | 0.60 | 7.89 | 0.52 | 2.49 |
실시예 1-13 | P3HT : 화학식1-1-11 = 1:1 | 0.58 | 8.21 | 0.38 | 1.8 |
실시예 1-14 | P3HT : 화학식1-1-12 = 1:1 | 0.65 | 8.89 | 0.56 | 3.23 |
실시예 1-15 | P3HT : 화학식1-1-13 = 1:1 | 0.61 | 8.08 | 0.67 | 3.30 |
Claims (29)
- 제1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비되는 1층 이상의 유기물층을 포함하는 유기 전자 소자로서,상기 유기물층 중 1층 이상은 하기 화학식 1로 표시되는 플러렌 유도체를 포함하는 것인 유기 전자 소자:[화학식 1]상기 화학식 1에 있어서,n은 1 내지 5의 정수이고,n이 2 이상인 경우, 괄호 내의 구조는 동일하거나 상이하며,Cn은 C60 내지 C120의 플러렌이고,R1 내지 R6은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 할로겐기; 니트로기; 시아노기; 카르복실산기; 히드록시기; 치환 또는 비치환된 카보닐기; 술포기(-SO3H); 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 에스터기; 치환 또는 비치환된 티오에스터기; 치환 또는 비치환된 아미드기; 치환 또는 비치환된 에테르기; 치환 또는 비치환된 술폰기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 헤테로아릴알킬기; 치환 또는 비치환된 아릴기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 치환기는 서로 결합하여, 치환 또는 비치환된 탄화수소고리; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 헤테로고리를 형성한다.
- 청구항 1에 있어서,R1 내지 R6 중 적어도 하나는 니트로기; 시아노기; 카르복실산기; 치환 또는 비치환된 카보닐기; 술포기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 에스터기; 치환 또는 비치환된 술폰기; 치환 또는 비치환된 아릴알킬기이거나, 인접하는 치환기는 서로 결합하여, 치환 또는 비치환된 탄화수소고리; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 헤테로고리를 형성하는 것인 유기 전자 소자.
- 청구항 1에 있어서,R7은 수소; 탄소수 1 내지 60의 치환 또는 비치환된 알킬기; 탄소수 3 내지 60의 치환 또는 비치환된 시클로알킬기; 탄소수 7 내지 50의 치환 또는 비치환된 아릴알킬기; 탄소수 2 내지 60의 치환 또는 비치환된 헤테로아릴알킬기; 탄소수 1 내지 40의 치환 또는 비치환된 카보닐기; 탄소수 6 내지 60의 치환 또는 비치환된 아릴기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 탄소수 2 내지 60의 치환 또는 비치환된 헤테로고리기인 것인 유기 전자 소자.
- 청구항 1에 있어서,상기 화학식 1로 표시되는 플러렌 유도체는 하기 화학식 2로 표시되는 플러렌 유도체를 포함하는 것인 유기 전자 소자:[화학식 2]상기 화학식 2에 있어서,Cn, n 및 R2 내지 R6의 정의는 상기 화학식 1에서 정의한 바와 동일하고,R7은 수소; 치환 또는 비치환된 카보닐기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 헤테로아릴알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아릴기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 헤테로고리기이다.
- 청구항 1에 있어서,상기 화학식 1로 표시되는 플러렌 유도체는 하기 화학식 3으로 표시되는 플러렌 유도체를 포함하는 것인 유기 전자 소자:[화학식 3]상기 화학식 3에 있어서,Cn, n, R1, R2 및 R4 내지 R6의 정의는 상기 화학식 1에서 정의한 바와 동일하고,R7은 수소; 치환 또는 비치환된 카보닐기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 헤테로아릴알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아릴기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 헤테로고리기이다.
- 청구항 1에 있어서,상기 유기 전자 소자는 유기 발광 소자; 유기 태양 전지; 및 유기 트랜지스터로 이루어진 군에서 선택되는 것인 유기 전자 소자.
- 청구항 1 내지 13 중 어느 한 항에 있어서,상기 유기 전자 소자는 제1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비되는 1층 이상의 유기물층을 포함하는 유기 태양 전지로서, 상기 유기물층 중 1층 이상이 상기 플러렌 유도체를 포함하는 유기 전자 소자.
- 청구항 14에 있어서,상기 유기물층은 광활성층을 포함하고,상기 광활성층은 n형 유기물층 및 p형 유기물층을 포함하는 이층 박막(bilayer)구조이며,상기 n형 유기물층은 상기 플러렌 유도체를 포함하는 것인 유기 전자 소자.
- 청구항 14에 있어서,상기 유기물층은 광활성층을 포함하고,상기 광활성층은 전자 주개 물질 및 전자 받개 물질을 포함하며,상기 전자 받개 물질은 상기 플러렌 유도체를 포함하는 것인 유기 전자 소자.
- 청구항 16에 있어서,상기 유기 전자 소자는 상기 전자 주개 물질과 상기 전자 받개 물질이 벌크 헤테로 정션(BHJ)을 구성하는 것인 유기 전자 소자.
- 청구항 16에 있어서,상기 전자 주개 물질은 유기화합물을 포함하고,상기 유기 화합물은 용액 공정이 가능한 유기 화합물인 것인 유기 전자 소자.
- 청구항 16에 있어서,상기 전자 주개 물질은 유기 화합물을 포함하고,상기 유기 화합물은 고분자 또는 단분자를 포함하는 것인 유기 전자 소자.
- 청구항 16에 있어서,상기 전자 받개 물질은 열경화 또는 UV 경화 처리를 하지 않는 상기 플러렌 유도체를 포함하는 것인 유기 전자 소자.
- 청구항 16에 있어서,상기 전자 받개 물질은 열경화 또는 UV 경화 처리를 한 상기 플러렌 유도체를 포함하는 것인 유기 전자 소자.
- 청구항 14에 있어서,상기 유기물층은 광활성층; 및 상기 광활성층과 상기 제1 전극 또는 상기 제2 전극 사이에 구비된 유기물층을 포함하고,상기 광활성층과 상기 제1 전극 또는 상기 제2 전극 사이에 구비된 유기물층은 상기 플러렌 유도체를 포함하는 것인 유기 전자 소자.
- 청구항 22에 있어서,상기 광활성층과 상기 제1 전극 또는 상기 제2 전극 사이에 구비된 유기물층은 상기 플러렌 유도체를 포함하고,상기 플러렌 유도체는 전자 전달 물질인 것인 유기 전자 소자.
- 청구항 22에 있어서,상기 광활성층과 상기 제1 전극 또는 상기 제2 전극 사이에 구비된 유기물층은 금속 산화물 (metal oxide)를 포함하고,상기 금속 산화물층과 광활성층 사이에 유기물층을 구비하며,상기 유기물층은 상기 플러렌 유도체를 포함하는 것인 유기 전자 소자.
- 청구항 22에 있어서,상기 광활성층과 상기 제1 전극 또는 상기 제2 전극 사이에 구비된 유기물층은 상기 플러렌 유도체를 포함하고,상기 플러렌 유도체는 전자 주입 물질인 것인 유기 전자 소자.
- 청구항 14에 있어서,상기 유기 전자 소자는 노멀(normal) 구조인 것인 유기 전자 소자.
- 청구항 14에 있어서,상기 유기 전자 소자는 노멀(normal)구조이고,상기 유기물층은 광활성층; 및 상기 광활성층과 상기 제1 전극 사이에 구비된 유기물층을 포함하고,상기 광활성층과 제1 전극 사이에 구비된 유기물층은 상기 플러렌 유도체를 포함하며,상기 제 1 전극은 애노드 전극이고, 상기 제2 전극은 캐소드 전극인 것인 유기 전자 소자.
- 청구항 14에 있어서,상기 유기 전자 소자는 인버티드(inverted) 구조인 것인 유기 전자 소자.
- 청구항 14에 있어서,상기 유기 전자 소자는 인버티드(inverted) 구조이고,상기 유기물층은 광활성층; 및 상기 광활성층과 상기 제1 전극 사이에 구비된 유기물층을 포함하고,상기 광활성층과 제1 전극 사이에 구비된 유기물층은 상기 플러렌 유도체를 포함하며,상기 제 1 전극은 애노드 전극이고, 상기 제2 전극은 캐소드 전극인 것인 유기 전자 소자.
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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EP3139420A4 (en) * | 2014-04-30 | 2017-12-13 | LG Chem, Ltd. | Organic solar cell and manufacturing method therefor |
CN104779351A (zh) * | 2015-03-31 | 2015-07-15 | 浙江大学 | 富勒烯冠醚衍生物及其在太阳能电池中的应用 |
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Publication number | Publication date |
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CN105190925A (zh) | 2015-12-23 |
KR101596132B1 (ko) | 2016-02-22 |
TWI602777B (zh) | 2017-10-21 |
CN105190925B (zh) | 2018-01-16 |
TW201512087A (zh) | 2015-04-01 |
US20160087213A1 (en) | 2016-03-24 |
JP2016521009A (ja) | 2016-07-14 |
US9711729B2 (en) | 2017-07-18 |
EP2975663B1 (en) | 2020-08-12 |
KR20140132273A (ko) | 2014-11-17 |
JP6208852B2 (ja) | 2017-10-04 |
EP2975663A4 (en) | 2016-11-23 |
EP2975663A1 (en) | 2016-01-20 |
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