WO2019078491A1 - Photodiode organique et capteur d'image organique la comprenant - Google Patents

Photodiode organique et capteur d'image organique la comprenant Download PDF

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WO2019078491A1
WO2019078491A1 PCT/KR2018/010895 KR2018010895W WO2019078491A1 WO 2019078491 A1 WO2019078491 A1 WO 2019078491A1 KR 2018010895 W KR2018010895 W KR 2018010895W WO 2019078491 A1 WO2019078491 A1 WO 2019078491A1
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formula
group
organic
compound
same
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PCT/KR2018/010895
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Korean (ko)
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임보규
김상아
김지훈
유승준
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주식회사 엘지화학
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Priority claimed from KR1020180110129A external-priority patent/KR102250385B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201880005198.9A priority Critical patent/CN110114896B/zh
Priority to US16/472,508 priority patent/US10756276B2/en
Priority to JP2019537215A priority patent/JP7200941B2/ja
Publication of WO2019078491A1 publication Critical patent/WO2019078491A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
    • H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components 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
    • H01L27/144—Devices controlled by radiation
    • H01L27/146—Imager structures
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the present disclosure relates to organic photodiodes and organic image sensors comprising them.
  • an organic photodiode having a high absorbance and a wide absorption wavelength has attracted attention as a substitute for a silicon diode, but the conventional organic photodiode has a problem in that efficiency in a visible light region is lower than that of a silicon diode. To solve this problem, it is necessary to study organic materials of organic photodiodes.
  • the present invention provides an organic photodiode and an organic image sensor including the organic photodiode.
  • One embodiment of the present disclosure includes a first electrode
  • At least one of the organic layers includes a compound represented by the following general formula (1).
  • Ra and Rb are the same or different and are each independently a group acting as an electron acceptor
  • Y1 to Y5 are the same or different from each other and each independently CRR ', NR, O, SiRR', PR, S, GeRR '
  • Y6 and Y7 are each independently of one another a direct bond, CRR ', NR, O, SiRR', PR, S, GeRR '
  • a 0 or 1
  • Y is a direct bond and Y7 is CRR ', NR, O, SiRR', PR, S, GeRR ', Se or Te when a is 0,
  • Y is a direct bond and Y6 is CRR ', NR, O, SiRR', PR, S, GeRR ', Se or Te,
  • n and m are each an integer of 0 to 5
  • n and m are 2 or more, the structures in parentheses are the same or different from each other,
  • R11 to R14 are the same or different and each independently represents an alkyl group having 1 to 4 carbon atoms
  • R1, R2, R and R ' are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • one embodiment of the present disclosure provides an organic image sensor comprising the organic photodiode.
  • the organic photodiode according to one embodiment of the present disclosure is capable of absorbing light in at least two of the green, red, and blue regions.
  • the organic layer of the organic photodiode according to one embodiment of the present disclosure can be formed through a deposition process.
  • the organic photodiode according to one embodiment of the present specification is excellent in efficiency.
  • FIG. 1 is a cross-sectional view illustrating an organic photodiode according to an embodiment of the present invention.
  • FIG. 3 is a graph showing the results of MALDI-TOF measurement of Compound 1.
  • FIG. 4 is a graph showing the current density according to the voltage of the organic photoelectric device manufactured in Example 1.
  • 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 provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of the formula (1).
  • This compound introduces sulfur (S) into the alkyl chain and improves the crystallinity by intramolecular chalcogen-chalcogen interaction.
  • the compound has an excellent charge mobility because it has a rigid structure by introducing a lower alkyl group into R11 to R14. Therefore, when applied to an organic photodiode, excellent efficiency can be exhibited.
  • a member when a member is located on another member, it includes not only the case where the member is in contact with the other member but also the case where another member exists between the two members.
  • Quot means a moiety bonded to another substituent, monomer, or binding site.
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted A halogen group; A nitrile group; A nitro group; Imide; Amide group; Carbonyl group; An ester group; A hydroxy group; An alkyl group; A cycloalkyl group; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; An alkenyl group; Silyl group; Siloxyl group; Boron group; An amine group; Arylphosphine groups; Phosphine oxide groups; An aryl group; And a heterocyclic group, or that at least two of the substituents exemplified in the above exemplified substituents are substituted with a connected substituent, or have no substituent.
  • a substituent to which at least two substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
  • the halogen group may be fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- Methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylpentyl, 2-methylpentyl, 2-methylpentyl, Butyl, heptyl, n-heptyl, 1-methylhexyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-propylpentyl, But are not limited to, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, 2,6-dimethyloctane and
  • the cycloalkyl group is not particularly limited, but is preferably a group having 3 to 30 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, sec-butyl, It is not.
  • the aryl group may be monocyclic or polycyclic.
  • the aryl group is a monocyclic aryl group
  • the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms.
  • Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.
  • the aryl group is a polycyclic aryl group
  • the number of carbon atoms is not particularly limited. And preferably 10 to 30 carbon atoms.
  • Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.
  • the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
  • the heterocyclic group includes at least one non-carbon atom or hetero atom, and specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, Se, and S, and the like.
  • the number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heterocyclic group may be monocyclic or polycyclic.
  • heterocyclic group examples include a thiophene group, an imidazolyl group, a thiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, a triazolyl group, an acridyl group, a pyridazinyl group, , A quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, , A dibenzothiophene group, a benzofuranyl group, a phenanthroline group, a thiazolyl group, an isoxazolyl group, an oxadiazol
  • the formula (1) may be represented by the following formula (2) or (3).
  • Y6 and Y7 are the same or different from each other and each independently CRR ', NR, O, SiRR', PR, S, GeRR '
  • Formula 3 may be represented by Formula 1-1 or Formula 1-2.
  • Y6 is CRR ', NR, O, SiRR', PR, S, GeRR ', Se or Te,
  • R1 and R2 are hydrogen.
  • Ra and Rb are the same or different from each other and each represent any one of the following structures.
  • c, d and e are each an integer of 1 to 4,
  • R20 to R25 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • Ra and Rb are the same or different from each other and each represent any one of the following structures.
  • R20 to R25 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • R20 to R25 are the same or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group.
  • R20 is a substituted or unsubstituted alkyl group.
  • R20 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
  • R20 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • R20 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
  • R20 is an ethyl group.
  • R21 to R23 are the same or different from each other, and are each independently a hydrogen or a halogen group.
  • R21 is hydrogen
  • R22 is hydrogen
  • R23 is hydrogen
  • R < 233 &gt is fluorine.
  • R24 is hydrogen
  • R25 is hydrogen
  • Ra and Rb are the same or different from each other and each represent any one of the following structures.
  • the formula 1 may be represented by any one of the following formulas 1-11 to 1-24.
  • Y6 and Y7 are the same or different from each other and each independently CRR ', NR, O, SiRR', PR, S, GeRR '
  • Y1, Y6, and Y7 are each S, respectively.
  • R11 to R14 are the same or different and are each independently an alkyl group having 1 to 4 carbon atoms.
  • R11 to R14 have 1 to 4 carbon atoms, the charge mobility is excellent because of having a rigid structure as compared with the case where the number of carbon atoms is 5 or more, which is advantageous for the deposition process.
  • each of R11 to R14 is a methyl group.
  • Formula 1 is represented by any one of the following structures.
  • the compound has a maximum absorption wavelength at 400 nm to 850 nm. And preferably has a maximum absorption wavelength at 450 to 700 nm. Accordingly, when applied to a diode, light can be absorbed in two or more regions of green, red, and blue regions, thereby improving the efficiency of the device.
  • the green region has a maximum emission wavelength of 500 nm to 570 nm
  • the red region has a maximum emission wavelength of 630 nm to 850 nm
  • the blue region has a maximum emission wavelength of 400 nm to 480 nm Quot; between "
  • the compound is capable of absorbing light in the visible light propagation region and absorbing light in the infrared region.
  • the wavelength range of about 380 nm to 780 nm can be absorbed. Accordingly, when applied to a diode, the absorption wavelength range of the device can be broadened.
  • the compound may be formed into a film through a deposition process.
  • the organic photodiode includes a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound.
  • the organic layer includes a photoactive layer
  • the photoactive layer includes an electron donor material and an electron donor material
  • the electron donor material includes the compound
  • the organic layer includes a photoactive layer
  • the photoactive layer includes a p-type organic layer and an n-type organic layer
  • the p-type organic layer includes the compound
  • the electron-accepting material and the n-type organic compound layer may be selected from the group consisting of fullerene, fullerene derivative, vicoproin, semiconducting element, semiconducting compound, and combinations thereof.
  • fullerene fullerene
  • fullerene derivative PCBM ((6,6) -phenyl- C 61 -butyric acid-methylester) or PCBCR ((6,6) -phenyl-C 61 -butyric acid-cholesteryl ester)
  • Perylene PBI polybenzimidazole
  • PTCBI 3,4,9,10-perylene-tetracarboxylic bis-benzimidazole
  • the electron donor material and the electron acceptor material constitute bulk heterojunction (BHJ).
  • Bulk heterojunction means that the electron donor material and the electron acceptor material are mixed with each other in the photoactive layer.
  • the photoactive layer is formed through a deposition process.
  • the photoactive layer may be formed by co-depositing an electron donor material and an electron acceptor material.
  • the photoactive layer may be formed by depositing an electron donor material and an electron acceptor material in different boats, and simultaneously depositing the electron donor material and the electron acceptor material on the electrode or the charge assist layer.
  • the electrode means the first electrode and / or the second electrode
  • the charge-assist layer means the electron-transporting layer and / or the hole-transporting layer.
  • the photoactive layer may be formed in a bilayer structure by sequentially depositing an electron donor material and an electron acceptor material.
  • the photoactive layer may be formed by sequentially depositing an electron donor and an electron donor to form a double layer comprising a p-type organic layer and an n-type organic layer.
  • the p-type organic layer and the n-type organic layer may be formed in a thickness ratio of 1: 9 to 9: 1. More specifically, it can be formed in a thickness ratio of 3: 7 to 7: 3.
  • An organic photodiode includes a first electrode, a photoactive layer, and a second electrode.
  • the organic photodiode may further include a substrate, a hole transporting layer, and / or an electron transporting layer.
  • the organic photodiode may further include a substrate, a hole transporting layer, and / or an electron transporting layer.
  • the organic photodiode may further include an additional organic layer.
  • the organic photodiode can reduce the number of organic layers by using organic materials having various functions at the same time.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode and the second electrode is an anode.
  • the organic photodiodes 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.
  • the organic photodiode is a normal structure.
  • the substrate, the anode, the organic material layer including the photoactive layer, and the cathode may be stacked in this order.
  • a passivation layer may be further included on the cathode.
  • the organic photodiode is an inverted structure.
  • the substrate, the cathode, the organic material layer including the photoactive layer, and the anode may be stacked in this order.
  • a passivation layer may be further included on the anode.
  • the passivation layer may be formed on the exposed surface of the organic photodiode and may absorb not only the protection of the organic photodiode but also the impact and stress generated when the substrate is removed.
  • 1 is a diagram illustrating an organic photodiode 100 according to an embodiment of the present invention.
  • 1, light is incident on the organic light emitting diode 100 from the side of the first electrode 10 and / or the second electrode 20, and when the active layer 30 absorbs light of a full wavelength range, Lt; / RTI >
  • the excitons are separated into holes and electrons in the active layer 30, and the separated holes move to the anode side, which is one of the first electrode 10 and the second electrode 20,
  • the current flows to the cathode side which is the other one of the two electrodes 20, and current can flow through the organic photodiode.
  • the organic photodiode is a tandem structure.
  • the organic photodiode can be used without limiting the materials and / or methods of the art, except that the compound is used as the photoactive layer.
  • 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. It does not. 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, but are not limited thereto .
  • 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 >
  • the anode electrode When the anode electrode is formed on a substrate, it may undergo cleaning, moisture removal and hydrophilic reforming processes.
  • the patterned ITO substrate is sequentially cleaned with a detergent, acetone, and isopropyl alcohol (IPA), and then heated on a heating plate at 100 ° C to 150 ° C for 1 minute to 30 minutes, preferably at 120 ° C for 10 minutes Dried, and the substrate surface is hydrophilically reformed when the substrate is completely cleaned.
  • IPA isopropyl alcohol
  • 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.
  • 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 radicals generated by the plasma And the like.
  • 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 pretreatment can be maximized.
  • a method of oxidizing the surface through ozone generated using UV can be used.
  • the ITO substrate patterned after the ultrasonic cleaning is dried by baking on a hot plate, and then put into a chamber. Then, by the action of a UV lamp, ozone generated by reaction of oxygen gas with UV light The patterned ITO substrate can be cleaned.
  • 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; Or a multilayer structure material such as LiF / Al, LiO 2 / Al, LiF / Fe, Al: Li, Al: BaF 2 and Al: BaF 2 : Ba.
  • the cathode may be deposited 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 passivation layer may be formed of an inorganic material such as a silicon oxide film (SiOx) and a silicon nitride film (SiNx), or an organic material such as benzocyclobutene (BCB) and photo acryl, but is not limited thereto.
  • an inorganic material such as a silicon oxide film (SiOx) and a silicon nitride film (SiNx)
  • an organic material such as benzocyclobutene (BCB) and photo acryl, but is not limited thereto.
  • the passivation layer may be formed on the exposed surface of the organic photodiode using Plasma Enhanced Chemical Vapor Deposition (PECVD).
  • PECVD Plasma Enhanced Chemical Vapor Deposition
  • the hole transporting layer and / or the electron transporting layer material efficiently transport 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.
  • PEDOT poly(styrenesulfonic acid)
  • MoO x molybdenum oxide
  • V 2 O 5 Vanadium oxide
  • NiO Nickel oxide
  • WO x tungsten oxide
  • the electron transport layer material may be BCP (bathocuproine) or electron-extracting metal oxides, specifically BCP (bathocuproine), 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.
  • Each of the hole transporting layer and the electron transporting layer may be formed by a method used in the art.
  • the solution may be formed by a method such as spin coating, dip coating, screen printing, spray coating, doctor blade, brush painting, etc., followeded by fixing, but it is not limited to these methods
  • One embodiment of the present disclosure provides an organic image sensor comprising the organic photodiode.
  • the organic image sensor according to one embodiment of the present invention can be applied to an electronic device, for example, a mobile phone, a digital camera, and the like, but is not limited thereto.
  • FIG. 3 is a graph showing the results of MALDI-TOF measurement of Compound 1.
  • Compound 2 was prepared in the same manner as in Production Example 2, except that Compound B-2 was used instead of Compound B-1. At this time, by measuring the molecular weight using MALDI-TOF, it was confirmed that Compound 2 was prepared. (MALDI-TOF molecular weight: 882.3 m / z)
  • Compound 3 was prepared in the same manner as in Production Example 2, except that Compound B-3 was used instead of Compound B-1. At this time, by measuring the molecular weight using MALDI-TOF, it was confirmed that Compound 3 was produced. (MALDI-TOF molecular weight: 786.5 m / z)
  • Compound 4 was prepared in the same manner as in Production Example 2, except that Compound B-4 was used instead of Compound B-1. At this time, by measuring the molecular weight using MALDI-TOF, it was confirmed that Compound 4 was prepared. (MALDI-TOF molecular weight: 978.3 m / z)
  • Compound 5 was prepared in the same manner as in Production Example 2, except that Compound B-5 was used instead of Compound B-1. At this time, molecular weight was measured using MALDI-TOF to confirm that Compound 5 was prepared. (MALDI-TOF molecular weight: 954.1 m / z)
  • Compound 6 was prepared in the same manner as in Production Example 2, except that Compound B-6 was used instead of Compound B-1. At this time, molecular weight was measured using MALDI-TOF to confirm that Compound 6 was prepared. (MALDI-TOF molecular weight: 838.1 m / z)
  • Compound 7 was prepared in the same manner as in Production Example 2, except that Compound B-7 was used instead of Compound B-1. At this time, by measuring the molecular weight using MALDI-TOF, it was confirmed that Compound 7 was produced. (MALDI-TOF molecular weight: 625.8 m / z)
  • ITO was sputtered on the glass substrate to form a first electrode (anode) having a thickness of about 100 nm, and a thin film of molybdenum oxide (MoOx, 0 ⁇ x? 3) was laminated thereon as a hole transport layer to a thickness of 30 nm. Subsequently, a compound (p-type organic compound layer) and C 60 (n-type organic compound layer) were deposited on a molybdenum oxide (MoO x, 0 ⁇ x? 3) thin film at a thickness ratio of 3: 4 to form a photoactive layer having a thickness of 80 nm.
  • a compound (p-type organic compound layer) and C 60 (n-type organic compound layer) were deposited on a molybdenum oxide (MoO x, 0 ⁇ x? 3) thin film at a thickness ratio of 3: 4 to form a photoactive layer having a thickness of 80 nm.
  • BCP bathoproine
  • Al aluminum
  • Table 1 shows the performance of the organic photoelectric devices prepared in Examples 1 to 5.
  • the results of Table 1 indicate that the organic photovoltaic device manufactured in the embodiment exhibits a value of the current (J) close to zero at the condition of no light (0 mW / cm 2 ) 2 ), the current value is increased. That is, it can be confirmed that when the compound according to one embodiment of the present invention is applied to an organic photoelectric device, it exhibits excellent performance.
  • FIG. 4 is a graph showing the current density according to the voltage of the organic photoelectric device manufactured in Example 1.
  • the current value in the case of no light shows a value adjacent to 0, which shows that the device has excellent performance.

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Abstract

La présente invention concerne une photodiode organique qui comprend une première électrode ; une seconde électrode qui fait face à la première électrode ; et au moins une couche de matériau organique qui est disposée entre la première électrode et la seconde électrode, au moins l'une des couches de matériau organique comprenant un composé de formule chimique 1, et un capteur d'image organique la comprenant.
PCT/KR2018/010895 2017-10-18 2018-09-17 Photodiode organique et capteur d'image organique la comprenant WO2019078491A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN201880005198.9A CN110114896B (zh) 2017-10-18 2018-09-17 有机光电二极管和包括其的有机图像传感器
US16/472,508 US10756276B2 (en) 2017-10-18 2018-09-17 Organic photodiode and organic image sensor including the same
JP2019537215A JP7200941B2 (ja) 2017-10-18 2018-09-17 有機光ダイオードおよびこれを含む有機イメージセンサ

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KR10-2017-0135199 2017-10-18
KR20170135199 2017-10-18
KR1020180110129A KR102250385B1 (ko) 2017-10-18 2018-09-14 유기 광 다이오드 및 이를 포함하는 유기 이미지 센서
KR10-2018-0110129 2018-09-14

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Citations (5)

* Cited by examiner, † Cited by third party
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