WO2016204275A1 - 有機電荷輸送層、有機elデバイス、有機半導体デバイス及び有機光電子デバイス - Google Patents
有機電荷輸送層、有機elデバイス、有機半導体デバイス及び有機光電子デバイス Download PDFInfo
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- WO2016204275A1 WO2016204275A1 PCT/JP2016/068114 JP2016068114W WO2016204275A1 WO 2016204275 A1 WO2016204275 A1 WO 2016204275A1 JP 2016068114 W JP2016068114 W JP 2016068114W WO 2016204275 A1 WO2016204275 A1 WO 2016204275A1
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- organic
- transport layer
- charge transport
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Images
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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
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
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- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
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- H10K50/00—Organic light-emitting devices
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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]
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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
- H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
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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
- H10K85/151—Copolymers
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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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/155—Hole transporting layers comprising dopants
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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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/156—Hole transporting layers comprising a multilayered structure
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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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- 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
- Y02E10/549—Organic PV cells
Definitions
- the present invention relates to an organic charge transport layer having a low refractive index, an organic EL device, an organic semiconductor device, and an organic optoelectronic device having the same.
- Non-Patent Document 1 a conventional method using a microlens or a high refractive index substrate is widely known. Has a problem of high.
- Non-Patent Document 2 a method of limiting the light emission from the transition dipole to the vertical direction of the substrate by the horizontal alignment of the light emitting molecules is being widely used (for example, Non-Patent Document 2), but there is still room for improving the light extraction efficiency. Are still left behind, and further improvements are desired.
- Amorphous organic semiconductor thin films used in organic EL devices and the like are composed of ⁇ -conjugated organic materials having a high molar refraction, and their refractive index is generally about 1.7 to 1.8 in the transparent region. It is known that there is. However, since these ⁇ -conjugated organic materials have a small controllable range of the refractive index, the light extraction efficiency cannot be significantly improved with a simple organic semiconductor material configuration.
- the inorganic material layer metal, conductive
- Oxides, insulating dielectrics, etc. must be used.
- the optical design freedom is low only by the control by the members outside the device, and the light propagation inside the device cannot be sufficiently controlled. Accordingly, there has been a demand for the development of an organic semiconductor material whose refractive index can be controlled.
- An object of the present invention is to provide an organic semiconductor thin film in which the refractive index of a film is greatly reduced without impairing conductivity by mixing an electret material in a predetermined amount with an organic semiconductor material.
- the present invention solves the above-described problems in the prior art, and includes the following items.
- the organic charge transport layer of the present invention contains an organic semiconductor material and an electret material.
- the organic semiconductor material is preferably a hole transport material.
- the electret material preferably has a refractive index of 1.5 or less.
- the electret material is polypropylene; Polytetrafluoroethylene (PTFE); Tetrafluoroethylene-hexafluoropropylene copolymer (FEP); Fluorine containing a 2,2-bistrifluoromethyl-4,5-difluoro-1,3-dioxole structural unit represented by the following formula (1) and a tetrafluoroethylene structural unit represented by the following formula (2) A copolymer; and
- X represents a hydrogen atom, a fluorine atom, a chlorine atom, a trifluoromethyl group or a trifluoromethoxy group
- Y represents an oxygen atom, a difluoromethylene group (CF 2 ) or a tetrafluoroethylene group.
- C 2 F 4 R 1 and R 2 each independently represents a fluorine atom, a trifluoromethyl group or a pentafluoroethyl group, and R 1 and R 2 are connected to each other to form 4 or more fluorine atoms.
- a 5-membered ring or a 6-membered ring containing atoms may be formed, and n represents an integer of 1 or more. From the viewpoint of film formability, n is preferably 10 or more.
- the organic EL device, organic semiconductor device or organic optoelectronic device of the present invention is characterized by using the organic charge transport layer.
- an electret material having a low refractive index is mixed with an organic semiconductor material in a predetermined amount, thereby greatly reducing the refractive index of the organic charge transport layer or the organic charge transport film without impairing conductivity.
- an organic semiconductor thin film in which the light extraction efficiency of the organic EL element is theoretically improved by 10 to 30%.
- FIG. 1 shows the ratio of ⁇ -NPD and AF1600 at a ratio of 100: 0 (only ⁇ -NPD), 78:22, 60:40, 45:55, 27:73, and 0: 100 (only AF1600). It is a figure showing the relationship of the wavelength-refractive index at the time of co-evaporating by volume ratio.
- FIG. 2 shows a case where ⁇ -NPD and AF1600 are co-deposited at a ratio of 100: 0 (only ⁇ -NPD), 78:22, 60:40, 45:55, and 27:73 (all are volume ratios). It is a figure showing the current density-voltage characteristic of.
- FIG. 1 shows the ratio of ⁇ -NPD and AF1600 at a ratio of 100: 0 (only ⁇ -NPD), 78:22, 60:40, 45:55, and 27:73 (all are volume ratios). It is a figure showing the current density-voltage characteristic of.
- FIG. 1 shows the
- FIG. 3 shows the ratio of TAPC and AF1600 at 100: 0 (only TAPC), 78:22, 70:30, 61:39, 45:55, 28:72, 0: 100 (AF1600 only) (both volumes).
- FIG. 6 is a graph showing the relationship between wavelength and refractive index when co-evaporation is performed at a ratio).
- FIG. 4 shows a case where TAPC and AF1600 are co-deposited at a ratio of 100: 0 (only TAPC), 78:22, 70:30, 61:39, 45:55, and 28:72 (all are volume ratios). It is a figure showing the current density-voltage characteristic of.
- FIG. 5 shows the light extraction efficiency of each layer for the organic EL device ITO / ⁇ -NPD: AF1600 mixed film (30 nm) / ⁇ -NPD (20 nm) / Alq 3 (50 nm) / LiF (1 nm) / Al (100 nm). It is a figure showing the result of having changed the refractive index of the alpha-NPD: AF1600 mixed film (30 nm) based on theoretical optical calculation, and using the experimental value of a refractive index and an emission spectrum. As indicated by the arrow ( ⁇ ), the light extraction efficiency is improved by reducing the refractive index to 1.5 by the organic charge transport layer of the present invention compared to the light extraction efficiency when the refractive index is 1.8. To do.
- FIG. 6 is a diagram showing the result of calculating the light extraction efficiency by changing the refractive index of an ⁇ -NPD: AF1600 mixed film (30 nm) based on theoretical optical calculation using the experimental values of the refractive index and emission spectrum of each layer. is there. As indicated by the arrow ( ⁇ ), the light extraction efficiency is improved by reducing the refractive index to 1.5 by the organic charge transport layer of the present invention compared to the light extraction efficiency when the refractive index is 1.8. To do.
- the organic charge transport layer of the present invention contains an organic semiconductor material and an electret material.
- An organic semiconductor material is an organic compound that exhibits semiconducting electrical properties.
- the refractive index of the organic semiconductor material with respect to visible light is usually about 1.7 to 1.8 in a wavelength region where the material does not absorb light.
- substrate in an organic optoelectronic device is about 1.5.
- materials responsible for charge transport are mainly classified into hole transport materials that are transported by receiving hole injection from the anode and electron transport materials that are transported by receiving electron injection from the cathode.
- the hole transport material include the following compounds ( ⁇ -NPD, TAPC). Refractive indexes of ⁇ -NPD and TAPC for vertically incident light having a wavelength of 532 nm are 1.82 and 1.68, respectively.
- Typical examples of the electron transporting material include the following compounds (Alq 3 , PBD, OXD7).
- the refractive indexes of Alq 3 , PBD, and OXD 7 for vertically incident light with a wavelength of 532 nm are 1.74, 1.67, and 1.67, respectively.
- the organic semiconductor material in the present invention either an electron transport material or a hole transport material can be used.
- the electron transport material since there are many materials that accumulate negative charges in the electret material, the electron transport material has a different charge.
- a hole transport material that flows is preferable, and ⁇ -NPD and TAPC are more preferable.
- the organic semiconductor material may be manufactured by a known method, or a commercially available product may be obtained.
- Examples of commercially available products include ⁇ -NPD (Lumtec, LT-E101) and TAPC (Lumtec, LT-N137).
- ⁇ -NPD is an abbreviation for 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl
- TAPC is 4,4-cyclohexylidenebis [N , N-bis (4-methylphenyl) benzeneamine].
- the electret material refers to a material that is solidified between electrodes to which a direct current voltage is applied and is charged to retain a charge when the electrode is removed, and the charge can be stored for a long period of time.
- the electret material in the present invention is not particularly limited as long as it has the above-described characteristics and can hold a charge semipermanently, but the refractive index is 1.5 from the viewpoint of refractive index control. The following are preferable, those having 1.4 or less are more preferable, and those having 1.2 to 1.4 are particularly preferable. Although a lower refractive index may be used, it is practically difficult to obtain such a material.
- the refractive index of the organic semiconductor material is approximately 1.7 to 1.8 in the wavelength region without light absorption.
- an electret material having a refractive index of 1.5 or less with an organic semiconductor material having such a refractive index in a predetermined amount, the refractive index of the obtained organic charge transport layer is lowered, and the organic charge Organic charge transport layer generated at the interface between the organic charge transport layer and the glass substrate by having a refractive index close to that of the quartz glass substrate adjacent to the transport layer or the glass substrate with ITO film (refractive index: about 1.5). Total reflection due to the difference in refractive index between the glass substrate and the glass substrate can be avoided, and the light extraction rate can be improved.
- the electret material is: polypropylene; Polytetrafluoroethylene (PTFE); Tetrafluoroethylene-hexafluoropropylene copolymer (FEP); Fluorine containing a 2,2-bistrifluoromethyl-4,5-difluoro-1,3-dioxole structural unit represented by the following formula (1) and a tetrafluoroethylene structural unit represented by the following formula (2) A copolymer; and
- Examples of the system copolymer include 65 mol% of 2,2-bistrifluoromethyl-4,5-difluoro-1,3-dioxole structural unit represented by the formula (1), and are represented by the formula (2).
- Teflon (registered trademark) AF1600 manufactured by DuPont; refractive index 1.31
- Teflon (registered trademark) AF2400 manufactured by DuPont; refractive index 1.29
- the total of the 2,2-bistrifluoromethyl-4,5-difluoro-1,3-dioxole structural unit represented by the formula (1) and the tetrafluoroethylene structural unit represented by the formula (2) is: 100 mol%.
- X represents a hydrogen atom, a fluorine atom, a chlorine atom, a trifluoromethyl group or a trifluoromethoxy group
- Y represents an oxygen atom, a difluoromethylene group (CF 2 ) or a tetrafluoroethylene group.
- C 2 F 4 R 1 and R 2 each independently represents a fluorine atom, a trifluoromethyl group or a pentafluoroethyl group, and R 1 and R 2 are connected to each other to form 4 or more fluorine atoms.
- a 5-membered ring or a 6-membered ring containing atoms may be formed, and n represents an integer of 1 or more.
- n is preferably 10 or more.
- Examples of the 5-membered ring or 6-membered ring containing a fluorine atom include a heterocyclic ring containing a —CF (CF 3 ) O (CF 2 ) 3 — structure.
- Specific examples of the compound containing the structural unit represented by the general formula (3) include that R 1 and R 2 are both fluorine atoms, X is a fluorine atom, and Y is a difluoromethylene group (CF 2 ).
- Examples of the compound include Cytop (trade name; manufactured by AGC Asahi Glass).
- n is preferably an integer of 5 or more, more preferably an integer of 10 or more. That is, the compound containing the structural unit represented by the general formula (3) may be a so-called oligomer having several repeating units or a polymer having more repeating units.
- amorphous materials are more preferable, and from the viewpoints of low refractive index and amorphous properties, AF1600, AF2400 and Cytop are more preferable, and from the viewpoint of lowering the refractive index Therefore, AF1600 and AF2400 are particularly preferable.
- an organic semiconductor material and an electret material are respectively put in separate cells in a vapor deposition apparatus and are usually heated on a quartz glass substrate or ITO glass at a degree of vacuum of 10 ⁇ 4 Pa or less by resistance heating. It may be co-evaporated, or after mixing the organic semiconductor material and electret material, it may be formed into a film by a process such as sputtering, or dissolved or dispersed in an organic solvent, and the inkjet method, casting method, The film may be formed by a wet process such as a dip coating method, a bar coating method, a blade coating method, a roll coating method, a gravure coating method, a flexographic printing method, or a spray coating method.
- the electret material is usually more than 0 vol% and 65 vol%, preferably 20 vol% to 65 vol%, more preferably 40 vol% to 60 vol%, particularly preferably relative to the organic semiconductor material (100 vol%). Is mixed at a ratio of 50 vol% or more and 55 vol% or less. When the mixing ratio of the electret material to the organic semiconductor material is within the above range, the refractive index at a wavelength of 550 nm is closest to 1.5, and is close to the refractive index of quartz glass or a glass substrate with an ITO film.
- the content of the electret material is 0 to 55 vol% with respect to the organic semiconductor material (100 vol%), the current density at the time of voltage application does not decrease compared to the case of 0 vol% (see FIGS. 2 and 4).
- the content of the electret material with respect to the organic semiconductor material is most preferably 50 to 55 vol%.
- Organic EL devices organic semiconductor devices, organic optoelectronic devices
- the organic EL device, organic semiconductor device, or organic optoelectronic device of the present invention uses the organic charge transport layer.
- the organic optoelectronic device is not particularly limited as long as it is an organic semiconductor device having a layer that plays a role of transporting holes or electrons, and examples thereof include an organic EL device and an organic thin film solar cell.
- Examples of the organic optoelectronic device according to the present invention include a device having a pair of electrodes, and at least one organic charge transport layer of the present invention sandwiched between the pair of electrodes.
- the organic optoelectronic device when the organic optoelectronic device requires a light-transmitting layer such as a light emitting layer and a power generation layer, the organic optoelectronic device includes a pair of electrodes each having a transparent conductive electrode and a counter electrode facing the transparent electrode. In addition to the organic charge transport layer, the translucent layer may be sandwiched between the electrodes.
- the method for sandwiching the organic charge transport layer of the present invention between an organic EL device, an organic semiconductor device, or an organic optoelectronic device is not particularly limited. For example, co-evaporation is performed by co-evaporation on a glass substrate with an ITO film by the method of Example. The film may be mounted on the device by a known method.
- the organic optoelectronic device of the present invention includes the organic charge transport layer, by controlling the refractive index, for example, it can achieve high luminous efficiency as an organic EL element and high conversion efficiency as an organic thin film solar cell. Can be obtained as a high-performance organic semiconductor device.
- Example 1 Evaluation of refractive index 1-1. Preparation of Sample A silicon substrate cut to approximately 2 cm square was ultrasonically cleaned using a neutral detergent, acetone, and isopropanol, and further boiled and washed in isopropanol. Then, deposits on the substrate surface were removed by ozone treatment.
- This substrate is placed in a vacuum vapor deposition machine and evacuated to a pressure of 10 ⁇ 4 Pa or less, and ⁇ -NPD as an organic semiconductor material and Teflon (registered trademark) AF1600 (manufactured by DuPont) as an electret material are used as ⁇ -Use resistance ratio heating in a vacuum evaporation machine using NPD and AF1600 ratios of 100: 0, 78:22, 60:40, 45:55, 27:73, 0: 100 (both volume ratios).
- the layers having a thickness of about 100 nm were prepared by co-evaporation. The total deposition rate of the two materials was 2.0 ⁇ / s.
- This substrate is placed in a vacuum vapor deposition machine and evacuated to a pressure of 10 -4 Pa or less, and then molybdenum trioxide is resistance-heated in the vacuum vapor deposition machine to form a hole injection layer on the substrate at a deposition rate of 0.1 nm / s. A 5 nm film was formed. Thereafter, the organic semiconductor material ⁇ -NPD and electret material AF1600 are set so that the ratio of ⁇ -NPD and AF1600 is 100: 0, 78:22, 60:40, 45:55, and 27:73 (all are volume ratios).
- resistance heating was performed in a vacuum deposition machine, and co-evaporation was performed, thereby laminating layers having a thickness of about 100 nm.
- aluminum was vapor-deposited in a strip shape having a width of 2 mm by resistance heating to obtain an evaluation element.
- the element area is 2 mm ⁇ 2 mm where 2 mm wide ITO and 2 mm wide aluminum intersect.
- the value when the refractive index is 1.8 is the light extraction efficiency of device ITO / ⁇ -NPD (50 nm) / Alq 3 (50 nm) / LiF (1 nm) / Al (100 nm) using a normal layer. Compared with the light extraction efficiency of 23.3% when the refractive index is 1.8, the light extraction efficiency is 27.0% by reducing the refractive index to 1.5 by the low refractive index charge transport layer of the present invention. A 16-fold improvement was seen.
- the device ITO / CsCo 3 (1 nm) / Alq 3 (50 nm) / ⁇ -NPD (50 nm) / MoO 3 (5 nm) / Al (100 nm) using a normal layer is used.
- Light extraction efficiency Compared with the light extraction efficiency of 21.8% when the refractive index is 1.8, the light extraction efficiency is 25.7% by reducing the refractive index of the organic charge transport layer to 1.5 with the mixed film of the present invention. .18-fold improvement was observed.
- Example 2 Evaluation of refractive index 1-1. Preparation of Sample In Example 1, TAPC was used as the organic semiconductor material, and the ratio of TAPC and AF1600 was 100: 0, 78:22, 70:30, 61:39, 45:55, 28:72, A layer having a thickness of about 100 nm was produced by co-evaporation in the same manner as in Example 1 except that the layer was used at 0: 100.
- Example 2 Device Preparation
- TAPC was used as the organic semiconductor material, and the ratio of TAPC to AF1600 was 100: 0, 78:22, 70:30, 61:39, 45:55, 28:72 ( An evaluation element was produced in the same manner as in Example 1 except that each was used so as to have a volume ratio).
- the organic charge transport layer of the present invention is suitably used as an organic EL device for operation panels and information display panels of various electronic devices, and also for various organic optoelectronic devices whose refractive index affects device characteristics. .
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Abstract
Description
本発明の有機電荷輸送層は、有機半導体材料及びエレクトレット材料を含有することを特徴とする。
前記有機半導体材料は正孔輸送材料であることが好ましい。
前記エレクトレット材料の屈折率は1.5以下であることが好ましい。
前記エレクトレット材料は、
ポリプロピレン;
ポリテトラフルオロエチレン(PTFE);
テトラフルオロエチレン-ヘキサフルオロプロピレン共重合体(FEP);
下記式(1)で表される2,2-ビストリフルオロメチル-4,5-ジフルオロ-1,3-ジオキソール構造単位と、下記式(2)で表されるテトラフルオロエチレン構造単位とを含むフッ素系共重合体;及び
[有機電荷輸送層]
本発明の有機電荷輸送層は、有機半導体材料及びエレクトレット材料を含有する。
有機半導体材料は、半導体的な電気的性質を示す有機化合物である。
有機半導体材料の可視光線に対する屈折率は、材料に光吸収のない波長領域で通常1.7~1.8程度である。なお、有機光電子デバイスにおける基板として、一般的に用いられるガラスの可視光線に対する屈折率は、約1.5である。
有機半導体材料の中でも、電荷の輸送を担う材料は、主に陽極から正孔注入を受けて輸送する正孔輸送材料と、陰極から電子注入を受けて輸送する電子輸送材料とに区分される。
本発明におけるエレクトレット材料としては、上記した特性を有し、電荷を半永久的に保持することができる材料であれば特に制限されるものではないが、屈折率制御の点から屈折率が1.5以下であるものが好ましく、1.4以下であるものがより好ましく、1.2~1.4であるものが特に好ましい。なお、さらに低い屈折率であってもよいが、このような材料の入手は現実的に困難である。
ポリプロピレン;
ポリテトラフルオロエチレン(PTFE);
テトラフルオロエチレン-ヘキサフルオロプロピレン共重合体(FEP);
下記式(1)で表される2,2-ビストリフルオロメチル‐4,5-ジフルオロ‐1,3-ジオキソール構造単位と、下記式(2)で表されるテトラフルオロエチレン構造単位とを含むフッ素系共重合体;及び
本発明の有機ELデバイス、有機半導体デバイス又は有機光電子デバイスはいずれも、上記有機電荷輸送層を用いたものである。有機光電子デバイスとしては、正孔あるいは電子を運搬する役割を果たす層を有する有機半導体デバイスであれば特に限定されず、例えば、有機ELデバイスや有機薄膜太陽電池等が挙げられる。
本発明の有機電荷輸送層を有機ELデバイス、有機半導体デバイス又は有機光電子デバイスに挟持させる方法は、特に限定されず、例えば、実施例の方法によりITO膜付きガラス基板に共蒸着させてなる共蒸着膜を公知の方法で上記デバイスに実装させればよい。
1.屈折率の評価
1-1.試料の作製
約2cm角にカットしたシリコン基板を、中性洗剤、アセトン、イソプロパノールを用いて超音波洗浄し、さらにイソプロパノール中で煮沸洗浄した上で、オゾン処理により基板表面の付着物を除去した。この基板を真空蒸着機内に置き、圧力10-4Pa以下に真空引きした上で、有機半導体材料としてα-NPDと、エレクトレット材料として、テフロン(登録商標)AF1600(デュポン社製)とを、α-NPDとAF1600の比率が100:0、78:22、60:40、45:55、27:73、0:100(いずれも体積比)となるように用いて、真空蒸着機内で抵抗加熱し、共蒸着を行うことでそれぞれ厚み約100nmの層を作製した。2つの材料の合計の蒸着速度は2.0Å/sとした。
多入射角分光エリプソメトリー(M-2000U;ジェー・エー・ウーラム社製)を用い、光の入射角を45~75度の範囲で5度ずつ変えて測定を行った。それぞれの角度において、波長245~1000nmの範囲で約1.6nmおきにエリプソメトリーパラメータであるΨとΔを測定した。上記の測定データを用い、有機半導体の誘電関数の虚部をガウス関数の重ね合わせで表現し、Kramers-Kronigの関係式を満たす条件下でフィッティング解析を行い、各波長の光に対する層の屈折率と消衰係数を得た。
α-NPDに対するAF1600の混合割合による、波長550nmにおける屈折率の変化を表1及び図1に示す。
2-1.素子の作製
評価用素子を作製するための基板として、2mm幅の帯状にITO(酸化インジウムスズ)が成膜されたガラス基板を用いた。その基板を中性洗剤、アセトン、イソプロパノールを用いて超音波洗浄し、さらにイソプロパノール中で煮沸洗浄した上で、オゾン処理によりITO膜表面の付着物を除去した。この基板を真空蒸着機内に置き、圧力10-4Pa以下に真空引きした上で、三酸化モリブデンを真空蒸着機内で抵抗加熱し、正孔注入層として基板上に蒸着速度0.1nm/sで5nm成膜した。その後、有機半導体材料α-NPDとエレクトレット材料AF1600を、α-NPDとAF1600の比率が100:0、78:22、60:40、45:55、27:73(いずれも体積比)となるように、真空蒸着機内で抵抗加熱し、共蒸着を行うことでそれぞれ厚み約100nmの層を積層した。さらに、アルミニウムを抵抗加熱で2mm幅の帯状に蒸着し、評価用素子とした。2mm幅のITOと2mm幅のアルミニウムが交差した2mm×2mmが素子面積となる。
ソースメータ(Keithley2401;Keithley社)により、ITO側を陽極、アルミニウム側を陰極として電圧を印加しながら、電圧毎に素子に流れる電流を測定した。結果を図2に示す。
AF1600混合比55vol%までは電気特性の低下は見られず、電気特性を損なうことなく、低屈折率化を実現できたことが示された。よって、α-NPDのようなトリフェニルアミン系正孔輸送材料の屈折率の大幅な低減に有効であることが示唆された。
1.屈折率の評価
1-1.試料の作製
実施例1において、有機半導体材料としてTAPCを使用したことと、TAPCとAF1600をその比率が100:0、78:22、70:30、61:39、45:55、28:72、0:100となるように使用したこと以外は、実施例1と同様にして、共蒸着を行い、厚み約100nmの層を作製した。
1-1.で得られた蒸着膜を用いて、実施例1と同様にして、屈折率を測定した。
TAPCに対するAF1600の混合割合による、波長550nmにおける屈折率の変化を表2及び図3に示す。
2-1.素子の作製
実施例1において、有機半導体材料としてTAPCを使用したことと、TAPCとAF1600をその比率が100:0、78:22、70:30、61:39、45:55、28:72(いずれも体積比)となるように使用したこと以外は、実施例1と同様にして、評価用素子を作製した。
2-1.で得られた評価用素子を用いて、実施例1と同様にして、電圧毎に素子に流れる電流を測定した。
結果を図4に示す。
実施例1及び2の結果から、α-NPDやTAPCのようなトリフェニルアミン系正孔輸送材料に、AF1600を約55vol%混合することで、波長550nmにおける屈折率が約1.5である超低屈折率正孔輸送層が実現できることがわかる。
よって、トリフェニルアミン系正孔輸送材料に、例えば、AF1600等のエレクトレット材料を所定量で混合するという手法は、正孔輸送層の屈折率の大幅な低減に有効であることが示唆される。
なお、実施例1及び2の結果から、AF1600がエレクトレット材料の特性として負電荷を保持し、絶縁物でありながら正孔の電流を阻害しない可能性が示唆される。
Claims (8)
- 有機半導体材料及びエレクトレット材料を含有することを特徴とする有機電荷輸送層。
- 前記有機半導体材料が正孔輸送材料であることを特徴とする、請求項1に記載の有機電荷輸送層。
- 前記エレクトレット材料の屈折率が1.5以下であることを特徴とする、請求項1に記載の有機電荷輸送層。
- 前記エレクトレット材料の屈折率が1.5以下であることを特徴とする、請求項2に記載の有機電荷輸送層。
- 前記エレクトレット材料が、
ポリプロピレン、
ポリテトラフルオロエチレン(PTFE)、
テトラフルオロエチレン-ヘキサフルオロプロピレン共重合体(FEP)、
下記式(1)で表される2,2-ビストリフルオロメチル‐4,5-ジフルオロ‐1,3-ジオキソール構造単位と、下記式(2)で表されるテトラフルオロエチレン構造単位とを含むフッ素系共重合体、及び
下記一般式(3)で表される構造単位を含むフッ素系重合体
からなる群より選ばれる少なくとも一種であることを特徴とする、請求項1~4のいずれか一項に記載の有機電荷輸送層。 - 請求項1~5のいずれか一項に記載の有機電荷輸送層を用いた有機ELデバイス。
- 請求項1~5のいずれか一項に記載の有機電荷輸送層を用いた有機半導体デバイス。
- 請求項1~5のいずれか一項に記載の有機電荷輸送層を用いた有機光電子デバイス。
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CN201680034484.9A CN107710439B (zh) | 2015-06-17 | 2016-06-17 | 有机电荷输送层、有机el设备、有机半导体设备及有机光电子设备 |
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- 2016-06-17 WO PCT/JP2016/068114 patent/WO2016204275A1/ja active Application Filing
- 2016-06-17 US US15/736,956 patent/US10381566B2/en not_active Expired - Fee Related
- 2016-06-17 KR KR1020187000725A patent/KR20180018671A/ko not_active Application Discontinuation
- 2016-06-17 EP EP16811749.7A patent/EP3312898B1/en active Active
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US10608183B2 (en) | 2016-12-14 | 2020-03-31 | AGC Inc. | Charge transport layer and organic photoelectronic element |
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Also Published As
Publication number | Publication date |
---|---|
CN107710439A (zh) | 2018-02-16 |
US20180366650A1 (en) | 2018-12-20 |
JPWO2016204275A1 (ja) | 2018-04-05 |
EP3312898A4 (en) | 2018-12-26 |
JP6709411B2 (ja) | 2020-06-17 |
EP3312898B1 (en) | 2021-04-28 |
KR20180018671A (ko) | 2018-02-21 |
EP3312898A1 (en) | 2018-04-25 |
US10381566B2 (en) | 2019-08-13 |
CN107710439B (zh) | 2019-09-24 |
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