WO2016088513A1 - 有機エレクトロルミネッセンス素子 - Google Patents
有機エレクトロルミネッセンス素子 Download PDFInfo
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- WO2016088513A1 WO2016088513A1 PCT/JP2015/081441 JP2015081441W WO2016088513A1 WO 2016088513 A1 WO2016088513 A1 WO 2016088513A1 JP 2015081441 W JP2015081441 W JP 2015081441W WO 2016088513 A1 WO2016088513 A1 WO 2016088513A1
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- light emitting
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- organic
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- 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
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
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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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- 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
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/22—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers
- H05B33/24—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers of metallic reflective layers
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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
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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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Definitions
- the present invention relates to an organic electroluminescence device, and more particularly to a high-efficiency and long-life organic electroluminescence device.
- a multi-unit organic EL element is an effective method for realizing a long-life organic electroluminescence (EL) element (for example, see Non-Patent Document 1).
- organic EL elements such as electric bulletin board use, traffic lights, various lighting, passenger car / motorcycle / bicycle lamps, lighting light sources, etc. used as monochromatic light outdoors.
- LEDs, incandescent lamps, and fluorescent lamps have been used from the viewpoints of efficiency, life, and reliability.
- the reason for the decrease in the light emission lifetime at the same luminance and the efficiency of the organic EL element is that the light emitted from the light emitting layer on the reflective electrode side is present on the transmissive electrode side of the light emitting layer (particularly, the organic layer) There is an absorption loss absorbed by the light-emitting layer, and light absorption by the light-emitting dopant in the light-emitting layer existing on the side of the transmissive electrode with respect to the light-emitting layer.
- the present invention has been made in view of the above problems and situations, and a problem to be solved is to provide a highly efficient and long-life organic electroluminescence element.
- the present inventor in the process of examining the cause of the above problems, the light emitting layer of the Nth light emitting unit and the light emitting layer of the (N + 1) th light emitting unit from the translucent electrode side. Includes a light-emitting dopant whose emission color is the same color system, the maximum emission maximum wavelength ⁇ N (max) of the EL spectrum of the light-emitting dopant in the light-emitting layer of the N-th light-emitting unit, and the light emission of the (N + 1) -th light-emitting unit It has been found that a high-efficiency and long-life organic electroluminescence device can be provided by making the difference between the maximum emission maximum wavelength ⁇ N + 1 (max) of the EL spectrum of the light-emitting dopant in the layer within a specific numerical range, and It came.
- the light emitting layer of the Nth light emitting unit and the light emitting layer of the (N + 1) th light emitting unit from the translucent electrode side contain a light emitting dopant whose emission color is the same color system,
- An organic electroluminescence device characterized in that the wavelength ⁇ N + 1 (max) satisfies the following conditional expression (1).
- optical distance from the translucent electrode to the light emitting layer of the Nth light emitting unit and the optical distance from the translucent electrode to the light emitting layer of the (N + 1) th light emitting unit are expressed by the following conditional expression (2
- the organic electroluminescence device according to item 1 characterized in that:
- All the light emitting layers of the plurality of light emitting units contain a light emitting dopant whose emission color is the same color system,
- the above-described means of the present invention can provide a highly efficient and long-life organic electroluminescence element.
- FIG. 1 shows the EL spectrum E N + 1 of the light-emitting dopant used in the light-emitting layer of the (N + 1) -th light-emitting unit, and the EL spectrum E N and absorption spectrum A N of the light-emitting dopant used in the light-emitting layer of the N-th light-emitting unit. It shows.
- An overlapping region S is formed at the bottom of the EL spectrum E N + 1 on the short wavelength side and the bottom of the absorption spectrum A N on the long wavelength side.
- the overlapping region S shown in FIG. 1 is large, and as a result, the light emitting layer on the reflective electrode side.
- the light emission from the light-emitting layer is absorbed by the light-emitting dopant in the light-emitting layer closer to the transmissive electrode than the light-emitting layer, and the light emission efficiency in the light-emitting dopant in the light-emitting layer on the transmissive electrode side is further reduced.
- the light emission efficiency in the light-emitting dopant in the light-emitting layer on the transmissive electrode side is further reduced.
- the maximum emission maximum wavelength ⁇ N (max) of the EL spectrum of the light emitting dopant in the light emitting layer of the Nth light emitting unit and the EL spectrum of the light emitting dopant in the light emitting layer of the (N + 1) th light emitting unit By adjusting the optical distance from the light emitting layer of each light emitting unit to the semi-transmissive electrode so that the difference from the maximum light emission maximum wavelength ⁇ N + 1 (max) is within a specific numerical range, As a result, the light emission from the light emitting layer in the (N + 1) th light emitting unit reduces the absorption loss absorbed by the light emitting layer material (including the host compound) in the Nth light emitting unit. It is considered that the photo-degradation of the dopant material is suppressed, and the efficiency and long life of the element itself can be increased.
- the light emitting layer of the Nth light emitting unit and the light emitting layer of the (N + 1) th light emitting unit from the translucent electrode side contain a light emitting dopant whose emission color is the same color system
- the maximum emission maximum wavelength ⁇ N (max) of the EL spectrum of the emission dopant in the emission layer of the Nth light emitting unit and the maximum emission maximum wavelength ⁇ N + 1 of the EL spectrum of the emission dopant in the emission layer of the (N + 1) th emission unit. max) satisfies the conditional expression (1).
- the optical distance from the semi-transmissive electrode to the light emitting layer of the Nth light emitting unit, and the light emission of the (N + 1) th light emitting unit from the semitransmissive electrode It is preferable that the optical distance to the layer satisfies the conditional expression (2).
- the maximum emission maximum wavelength ⁇ N (max) of the EL spectrum of the emission dopant in the light emitting layer of the Nth light emitting unit and the light emitting layer of the (N + 1) th light emitting unit It is preferable that the maximum emission maximum wavelength ⁇ N + 1 (max) of the EL spectrum of the luminescent dopant in the above satisfies the conditional expression (3), more preferably the conditional expression (4).
- the light emitting layers of the plurality of light emitting units contain a light emitting dopant whose emission color is the same color.
- ⁇ representing a numerical range is used in the sense that numerical values described before and after the numerical value range are included as a lower limit value and an upper limit value.
- the organic EL element of the present invention has a plurality of light emitting units between a pair of semi-transmissive electrodes (also referred to as anodes) and a reflective electrode (also referred to as cathode), and charge generation is generated between the light emitting units.
- the light emitting layer of the Nth light emitting unit and the light emitting layer of the (N + 1) th light emitting unit from the translucent electrode side contain a light emitting dopant whose emission color is the same color system.
- the maximum emission maximum wavelength ⁇ N (max) of the EL spectrum of the luminescent dopant in the light emitting layer of the light emitting unit, and the maximum emission maximum wavelength ⁇ N + 1 (max) of the EL spectrum of the luminescent dopant in the light emitting layer of the (N + 1) th light emitting unit Satisfies the following conditional expression (1).
- the light emitting dopant contained in the light emitting layer of the Nth light emitting unit and the light emitting layer of the (N + 1) th light emitting unit It is also possible to control by the method of changing the luminescent dopant contained.
- the organic EL element of the present invention has an optical distance from the semi-transmissive electrode to the light emitting layer of the Nth light emitting unit and an optical distance from the semitransmissive electrode to the light emitting layer of the (N + 1) th light emitting unit. It is preferable that the following conditional expression (2) is satisfied.
- An organic EL element 1 shown in FIG. 2 includes a semi-transmissive electrode 2, a first light emitting unit 4, a charge generating unit 6, a second light emitting unit 8, and a reflective electrode 10.
- the first light-emitting unit 4 and the second light-emitting unit 8 are respectively composed of layers 4a and 8a having a hole transporting property composed of a hole injection layer, a hole transport layer, an electron blocking layer, and the like, and light emitting layers 4b and 8b. It has layers 4c and 8c having an electron transporting property composed of a hole blocking layer, an electron transport layer, an electron injection layer, and the like.
- the organic EL element 1 includes at least a light emitting organic material in the light emitting layers 4b and 8b.
- the light emitting organic material has the same color from among blue (B), green (G), red (R), and the like.
- the organic EL element 1 has a so-called bottom emission type configuration in which light is extracted from the translucent electrode 2 side.
- the optical distances n 1 d 1 and n 2 d 2 from the translucent electrode 2 to the light emitting layers 4b and 8b are set to (2m + 1) / 4 times the light emission wavelength of the light emitting dopant. While adjusting, the maximum emission maximum wavelength ⁇ 1 (max) of the EL spectrum of the luminescent dopant in the light emitting layer 4b at that time is the maximum emission maximum wavelength ⁇ 2 (max) of the EL spectrum of the luminescent dopant in the light emitting layer 8b. External extraction efficiency is improved by adjusting the optical distance so as to be on the short wavelength side within the range of 1 to 50 nm.
- the optical distance is appropriately changed in any layer thickness between the light emitting layer and the semi-transmissive electrode, for example, the layers 4a and 8a having hole transporting property, the light emitting layer 4b, the layer 4c having electron transporting property, and the like. To be adjusted.
- the refractive index and the optical distance are values measured and analyzed by regarding all the layers sandwiched between the semi-transmissive electrode and the light emitting layer as one layer.
- the refractive index and the layer thickness can be measured, for example, by using a UVSEL / FUV-FGMS manufactured by Horiba JYOBIN-YVON as a spectroscopic ellipsometer or an FE3000 manufactured by Otsuka Electronics as a reflective spectral film thickness meter.
- the analysis is performed with Cauchy (n (refractive index): variable, k (attenuation coefficient): fixed without wavelength) in the wavelength range of 500 to 800 nm, and the refractive index and the layer thickness are measured.
- the refractive index and the optical distance may be measured by forming a layer to be measured on a silicon wafer, or may be measured with a focused ion beam (FIB) or the like after the element or panel is manufactured. Minutes may be separated or measured.
- FIB focused
- the maximum emission maximum wavelength of the emission spectrum of the emission dopant in the emission layer of the Nth emission unit is the maximum emission of the emission spectrum of the emission dopant in the emission layer of the (N + 1) th emission unit. It is preferably 5 to 50 nm shorter than the maximum wavelength, and more preferably 20 to 50 nm shorter.
- all the light emitting layers of the organic EL element contain a light emitting dopant whose emission color is the same color.
- N is preferably an integer of 1 to 4.
- the organic EL element of the present invention can increase the color purity in the same color system because each light emitting unit is sufficiently separated by the charge generation unit or the like and can suppress the Forster transition.
- a hole blocking layer (also referred to as a hole blocking layer) may be provided between the light emitting layer and the reflective electrode or the charge generation unit, and the light emitting layer and the semitransparent electrode or charge generation may be provided.
- An electron blocking layer (also referred to as an electron barrier layer) may be provided between the units.
- Different second and third hole transport layers and electron transport layers may be formed. In the above element configuration, the case where N is an integer of 1 to 4, that is, the number of light emitting units is 2 to 5, but the number of light emitting units may be 6 or more.
- the light emitting layer of the Nth light emitting unit and the light emitting layer of the (N + 1) th light emitting unit from the translucent electrode side contain a light emitting dopant whose emission color is the same color system. It is characterized by.
- the same color system is a color system belonging to the same color system.
- red system light means red light having a wavelength band of about 550 to 700 nm
- green system light is about 480 to 600 nm.
- Green light in the wavelength band of blue is blue light in the wavelength band of about 400 to 530 nm
- the absolute value of the difference between the maximum emission maximum wavelengths of the EL spectrum is preferably within 50 nm.
- each structure of the organic EL element demonstrated below is an example for demonstrating this embodiment, and it is also possible to apply another structure suitably in the range which can comprise the above-mentioned organic EL element. is there.
- the organic EL element of the present invention has two continuous light-emitting units each having a light-emitting layer whose emission color is the same color system. When three or more light emitting units are included, it is preferable that the light emission colors of all the light emitting layers are the same color system.
- the light emitting unit may appropriately include an organic layer such as a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer in addition to the light emitting layer.
- the light emitting layer is a layer including a light emitting organic semiconductor thin film that provides a field in which electrons and holes injected from an electrode or an adjacent layer are recombined to emit light via excitons.
- the portion that emits light may be within the light emitting layer or at the interface between the light emitting layer and the adjacent layer.
- the light emitting layer preferably includes at least one light emitting material including a light emitting organic material.
- a phosphorescent light emitting material and a fluorescent light emitting material may be mixed, but it is preferable that the light emitting layer is composed only of the phosphorescent light emitting material or the fluorescent light emitting material.
- the fluorescent light emitting layer and the phosphorescent light emitting layer are preferably host-dopant type light emitting layers.
- the number of layers constituting the light emitting layer may be any number, and there may be a plurality of layers having the same light emission spectrum or light emission maximum wavelength.
- the total thickness of the light emitting layer is not particularly limited, but it prevents the uniformity of the film to be formed, the application of unnecessary high voltage during light emission, and the improvement of the stability of the emission color against the drive current. From the viewpoint, it is preferable to adjust within the range of 5 to 200 nm, and more preferably within the range of 10 to 150 nm. Further, the thickness of each light emitting layer is preferably adjusted within a range of 5 to 200 nm, more preferably within a range of 10 to 40 nm.
- Luminescent dopant As the luminescent dopant, a fluorescent luminescent dopant (also referred to as a fluorescent dopant or a fluorescent compound) and a phosphorescent dopant (also referred to as a phosphorescent dopant or a phosphorescent compound) are preferably used. .
- the concentration of the light-emitting dopant in the light-emitting layer can be arbitrarily determined based on the specific dopant used and the device requirements.
- the concentration of the light emitting dopant may be contained at a uniform concentration in the thickness direction of the light emitting layer, or may have an arbitrary concentration distribution.
- a material other than the host compound and the light emitting dopant may be included as an assist dopant for the purpose of assisting light emission.
- the phosphorescent dopant is a compound in which light emission from an excited triplet is observed, specifically, a compound that emits phosphorescence at room temperature (25 ° C.). , A compound having a phosphorescence quantum yield of 0.01 or more at 25 ° C. In the phosphorescent dopant used for a light emitting layer, a preferable phosphorescence quantum yield is 0.1 or more.
- the phosphorescence quantum yield can be measured by the method described in Spectra II, page 398 (1992 edition, Maruzen) of Experimental Chemistry Course 4 of the 4th edition. The phosphorescence quantum yield in a solution can be measured using various solvents.
- the phosphorescence emitting dopant used for the light emitting layer should just achieve the said phosphorescence quantum yield (0.01 or more) in any solvent.
- an excited state of the host compound is generated by recombination of carriers on the host compound to which carriers are transported. It is an energy transfer type in which light is emitted from the phosphorescent dopant by transferring this energy to the phosphorescent dopant.
- the other is a carrier trap type in which a phosphorescent dopant becomes a carrier trap, carrier recombination occurs on the phosphorescent dopant, and light emission from the phosphorescent dopant is obtained. In any case, it is a condition that the excited state energy of the phosphorescent dopant is lower than the excited state energy of the host compound.
- a phosphorescent dopant it can select from the well-known material used for the light emitting layer of an organic EL element suitably, and can use it.
- Specific examples of known phosphorescent dopants include Nature 395, 151 (1998), Appl. Phys. Lett. 78, 1622 (2001), Adv. Mater. 19, 739 (2007), Chem. Mater. 17, 3532 (2005), Adv. Mater. 17, 1059 (2005), International Publication No. 2009/100991, International Publication No. 2008/101842, International Publication No. 2003/040257, US Patent Application Publication No. 2006/835469, US Patent Application Publication No. 2006 /. No. 0202194, U.S. Patent Application Publication No.
- JP2013-4245A structures represented by general formula (4), general formula (5), and general formula (6) described in paragraphs [0185] to [0235] of JP2013-4245A
- Preferred examples thereof include compounds having the following formulas and exemplary compounds (Pt-1 to Pt-3, Os-1 and Ir-1 to Ir-45).
- a preferable phosphorescent dopant is an organometallic complex having Ir as a central metal. More preferably, a complex containing at least one coordination mode of metal-carbon bond, metal-nitrogen bond, metal-oxygen bond, and metal-sulfur bond is preferable.
- the fluorescent luminescent dopant is a compound that can emit light from an excited singlet, and is not particularly limited as long as light emission from the excited singlet is observed.
- Examples of the fluorescent light-emitting dopant include anthracene derivatives, pyrene derivatives, chrysene derivatives, fluoranthene derivatives, perylene derivatives, fluorene derivatives, arylacetylene derivatives, styrylarylene derivatives, styrylamine derivatives, arylamine derivatives, boron complexes, coumarin derivatives, Examples include pyran derivatives, cyanine derivatives, croconium derivatives, squalium derivatives, oxobenzanthracene derivatives, fluorescein derivatives, rhodamine derivatives, pyrylium derivatives, perylene derivatives, polythiophene derivatives, rare earth complex compounds, and the like.
- a light emitting dopant using delayed fluorescence may be used as the fluorescent light emitting dopant.
- Specific examples of the luminescent dopant using delayed fluorescence include compounds described in, for example, International Publication No. 2011/156793, Japanese Patent Application Laid-Open No. 2011-213643, Japanese Patent Application Laid-Open No. 2010-93181, and the like.
- the host compound is a compound mainly responsible for charge injection and transport in the light emitting layer, and its own light emission is not substantially observed in the organic EL element.
- it is a compound having a phosphorescence quantum yield of phosphorescence emission of less than 0.1 at room temperature (25 ° C.), more preferably a compound having a phosphorescence quantum yield of less than 0.01.
- the mass ratio in the layer is 20% or more among the compounds contained in a light emitting layer.
- the excited state energy of the host compound is preferably higher than the excited state energy of the light-emitting dopant contained in the same layer.
- the host compound may be used alone or in combination of two or more. By using a plurality of types of host compounds, it is possible to adjust the movement of electric charges, and it is possible to increase the efficiency of the organic EL element.
- the compound conventionally used with the organic EL element can be used.
- it may be a low molecular compound, a high molecular compound having a repeating unit, or a compound having a reactive group such as a vinyl group or an epoxy group.
- Tg glass transition temperature
- the glass transition point (Tg) is a value obtained by a method based on JIS K 7121 using DSC (Differential Scanning Calorimetry).
- the host compound of the light emitting layer containing the phosphorescent dopant the lowest excited triplet energy (T 1) is preferably larger than 2.1 eV.
- T 1 is larger than 2.1 eV, high luminous efficiency can be obtained.
- the lowest excited triplet energy (T 1 ) is the peak energy of the emission band corresponding to the transition between the lowest vibrational bands of the phosphorescence emission spectrum observed at the liquid nitrogen temperature or the liquid helium temperature after dissolving the host compound in the solvent.
- the hole injection layer (also referred to as “anode buffer layer”) is a layer provided between the anode and the light emitting layer in order to reduce driving voltage and improve light emission luminance.
- An example of the hole injection layer is “Organic EL device and its industrialization front line (November 30, 1998, issued by NTT)”, Chapter 2, Chapter 2, “Electrode material” (pages 123-166). It is described in.
- the hole injection layer is provided as necessary, and is provided between the anode or the charge generation unit and the light emitting layer or the hole transport layer as described above. Details of the hole injection layer are described in JP-A-9-45479, JP-A-9-260062, JP-A-8-288069 and the like.
- A represents C or N.
- X represents N or CR 0.
- R 0 represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a formyl group, an acetyl group, or benzoyl.
- R 1 and R 2 each independently represents a substituted alkyl group, aryl group, aralkyl group, alkylamino group, arylamino group, aralkylamino group or heterocyclic group.
- Y, Y ′ and Y ′′ are substituted Represents an unsubstituted 5-membered aromatic heterocycle containing A and X as ring members or a 6-membered aromatic heterocycle containing A and X as ring members.
- Y, Y ′ and Y ′′ may be the same May be different.
- the alkyl group in R 0 of the general formula (1) preferably has 1 to 20 carbon atoms, and examples thereof include a linear alkyl group such as a methyl group, an ethyl group, a propyl group, and a hexyl group, and an isopropyl group. and branched chain alkyl groups such as t-butyl group.
- the aryl group include a monocyclic aromatic hydrocarbon ring group such as a phenyl group, and a polycyclic aromatic hydrocarbon ring group such as a naphthyl group, an anthracenyl group, a pyrenyl group, and a perylenyl group.
- an alkyl group having 1 to 20 carbon atoms substituted with an aromatic hydrocarbon ring group such as a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, an anthracenyl group, a pyrenyl group, a perylenyl group, etc.
- an aromatic hydrocarbon ring group such as a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, an anthracenyl group, a pyrenyl group, a perylenyl group, etc.
- alkylamino group include an amino group substituted with an aliphatic hydrocarbon having 1 to 20 carbon atoms.
- Examples of the arylamino group include an amino group substituted with an aromatic hydrocarbon ring group such as a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, an anthracenyl group, a pyrenyl group, and a perylenyl group.
- Examples of the aralkylamino group include an aromatic hydrocarbon ring group such as a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, an anthracenyl group, a pyrenyl group, and a perylenyl group, and an aliphatic hydrocarbon having 1 to 20 carbon atoms.
- heterocyclic group examples include pyrrolyl group, thienyl group, indolyl group, oxazolyl group, imidazolyl group, thiazolyl group, pyridyl group, pyrimidinyl group, piperazinyl group, thiophenyl group, furanyl group, and pyridazinyl group.
- Examples of the alkyl group having 1 to 60 carbon atoms in R 1 and R 2 in the general formula (1) include a linear alkyl group such as a methyl group, an ethyl group, a propyl group, and a hexyl group, an isopropyl group, a t-butyl group, and the like. And branched chain alkyl groups.
- Examples of the aryl group include a monocyclic aromatic hydrocarbon ring group such as a phenyl group, and a polycyclic aromatic hydrocarbon ring group such as a naphthyl group, an anthracenyl group, a pyrenyl group, and a perylenyl group.
- Examples of the 5- to 7-membered heterocyclic group include pyrrolyl group, thienyl group, indolyl group, oxazolyl group, imidazolyl group, thiazolyl group, pyridyl group, pyrimidinyl group, piperazinyl group, thiophenyl group, furanyl group, pyridazinyl group and the like. .
- a pyrazole ring As the 5-membered aromatic heterocycle in Y, Y ′ and Y ′′ of the general formula (1), a pyrazole ring, an imidazole ring, a thiazole ring, an oxazole ring, an isoxazole ring, an indole ring, a triazole ring, a benzimidazole ring, Examples thereof include a benzopyrazole ring, a benzothiazole ring, a benzoxazole ring, and a benzoisoxazole ring.
- the 6-membered aromatic heterocycle include a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, and a triazine ring.
- R 0 to R 2 and Y, Y ′ and Y ′′ in the general formula (1) may be substituted, and examples of the substituent include linear or branched alkyl groups (for example, methyl group, ethyl group).
- alkenyl group for example, vinyl group, allyl group, etc.
- alkynyl group Formula example, ethynyl group, propargyl group, etc.
- aromatic hydrocarbon ring group also referred to as aromatic carbocyclic group, aryl group, etc.
- Aromatic heterocyclic group for example, furan ring, dibenzofuran ring, thiophene ring, dibenzothiophene ring, oxazole ring, pyrrole ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring, benzimidazole ring, oxadi Azole ring, triazole ring, imidazole ring, pyrazole ring, thiazole ring, indole ring, indazole ring, benzimidazole ring, benzothiazole ring, benzoxazole ring, quinoxaline ring, quinazoline ring, cinnoline ring, quinoline ring, isoquinoline ring A group derived from a phthalazine ring, a naphthyridine ring, a carbazole ring, a carbazole
- the compound having a structure represented by the general formula (1) is preferably a compound having a structure represented by the following general formula (2).
- R 3 to R 8 are each independently a hydrogen atom, halogen atom, cyano group, nitro group, sulfonyl group (—SO 2 R 9 ), sulfinyl group (—SOR 9 ), sulfone.
- An amide group (—SO 2 NR 9 R 10 ), a sulfonate group (—SO 3 R 9 ), a trifluoromethyl group, an ester group (—COOR 9 ), an amide group (—CONHR 9 or —CONR 9 R 10 ), and A substituted or unsubstituted linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched alkoxy group having 1 to 12 carbon atoms, an aromatic hydrocarbon ring group, an arylamino group, a non-aromatic heterocyclic group, R 9 and R 10 each independently represents a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, an aromatic heterocyclic group or an aralkylamino group. Represents a reel group or a 5- to 7-membered heterocyclic group.)
- R 9 and R 10 in the general formula (2) have the same meanings as R 1 and R 2 in the general formula (1).
- R 3 to R 10 in the general formula (2) may be substituted, and examples of the substituent include the same substituents as in the general formula (1).
- the compound having a structure represented by the general formula (1) is preferably a compound having a structure represented by the following general formula (3).
- R 11 to R 22 are each independently a halogen atom, amino group, cyano group, nitro group, alkoxy group, aryloxy group, alkylthio group, arylthio group, acyl group, alkoxycarbonyl group.
- R 11 to R 22 may each form a ring with adjacent substituents.
- Examples of the alkoxy group in R 11 to R 22 in the general formula (3) include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group, and an octyl group.
- Examples thereof include an alkoxyl group having 1 to 18 carbon atoms such as an oxy group, a tert-octyloxy group, a 2-bornyloxy group, a 2-isobornyloxy group, and a 1-adamantyloxy group.
- the aryloxy group includes a phenoxy group, a 4-tert-butylphenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 9-anthryloxy group, a 2-phenanthryloxy group, a 1-naphthacenyl group, 1 Examples thereof include aryloxy groups having 6 to 30 carbon atoms, such as -pyrenyl group, 2-chrycenyl group, 3-perylenyl group, and 1-pentacenyl group.
- alkylthio group examples include methylthio group, ethylthio group, propylthio group, butylthio group, isobutylthio group, tert-butylthio group, pentylthio group, isopentylthio group, hexylthio group, isohexylthio group, heptyl group, and octylthio group. Examples thereof include 1 to 18 alkylthio groups.
- arylthio group examples include arylthio groups having 6 to 30 carbon atoms such as phenylthio group, 4-methylphenylthio group, 4-tert-butylphenylthio group, and 1-naphthylthio group.
- acyl group examples include acyl groups having 2 to 18 carbon atoms such as acetyl group, propionyl group, pivaloyl group, cyclohexylcarbonyl group, benzoyl group, toluoyl group, anisoyl group, cinnamoyl group and the like.
- alkoxycarbonyl group examples include carbon such as methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, butoxycarbinyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, heptyloxycarbonyl group, octyloxycarbonyl group, benzyloxycarbonyl group, etc. Examples thereof include alkoxycarbonyl groups of 2 to 18.
- the aryloxycarbonyl group include aryloxycarbonyl groups having 7 to 30 carbon atoms such as a phenoxycarbonyl group, a 1-naphthyloxycarbonyl group, and a 2-phenanthryloxycarbonyl group.
- alkylsulfonyl group examples include alkylsulfonyl having 1 to 18 carbon atoms such as mesyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, heptylsulfonyl group, octylsulfonyl group, and nonylsulfonyl group.
- alkylsulfonyl having 1 to 18 carbon atoms such as mesyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, heptylsulfonyl group, octylsulfonyl group, and nonyl
- arylsulfonyl group examples include arylsulfonyl groups having 6 to 30 carbon atoms such as a benzenesulfonyl group, a p-toluenesulfonyl group, and a 1-naphthylsulfonyl group.
- Examples of the aliphatic hydrocarbon group include alkyl groups (for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, hexyl group, isohexyl group, A heptyl group, an octyl group, a nonyl group, a decyl group, a dodecyl group, a pentadecyl group, an octadecyl group and the like, an alkenyl group (for example, a vinyl group, a 1-propenyl group, a 2-propenyl group, an iso group) Propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-octenyl group, 1-decenyl group, 1-octenyl group and the like, alkyny
- Examples of the aromatic hydrocarbon ring group include 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 5-anthryl group, 1-phenanthryl group, 9-phenanthryl group, 1-acenaphthyl group, 2 -Triphenylenyl group, 1-chrycenyl group, 2-azurenyl group, 1-pyrenyl group, 2-triphenylyl group, 1-pyrenyl group, 2-pyrenyl group, 1-perylenyl group, 2-perylenyl group, 3-perylenyl group, 2 A condensed ring hydrocarbon group having 10 to 30 carbon atoms such as indenyl group, 1-acenaphthylenyl group, 2-naphthacenyl group, 2-pentacenyl group, o-biphenylyl group, m-biphenylyl group, p-biphenylyl group, terphen
- aliphatic heterocyclic group examples include monovalent aliphatic heterocyclic groups having 3 to 18 carbon atoms such as a 3-isochromanyl group, a 7-chromanyl group, a 3-coumarinyl group, a piperidino group, a morpholino group, and a 2-morpholinyl group. Can be mentioned.
- the aromatic heterocyclic group includes 2-furyl group, 3-furyl group, 2-thienyl group, 3-thienyl group, 2-benzofuryl group, 2-benzothienyl group, 2-pyridyl group, 3-pyridyl group, 4 And aromatic heterocyclic groups having 3 to 30 carbon atoms such as -pyridyl group, 2-quinolyl group and 5-isoquinolyl group.
- R 11 to R 22 in the general formula (3) may be substituted, and examples of the substituent include those similar to the substituent in the general formula (1).
- R 23 to R 28 each independently represents a substituted or unsubstituted alkyl group, aryl group, aralkyl group or heterocyclic group.
- R 23 to R 28 may be the same or different.
- R 23 and R 24 , R 25 and R 26 and R 27 and R 28 , or R 23 and R 28 , R 24 and R 25, and R 26 and R 27 form a condensed ring. May be.
- Examples of the alkyl group in R 23 to R 28 in the general formula (4) include linear alkyl groups such as a methyl group, an ethyl group, a propyl group, and a hexyl group, and branched alkyl groups such as an isopropyl group and a t-butyl group.
- Examples of the aryl group include a monocyclic aromatic hydrocarbon ring group such as a phenyl group, and a polycyclic aromatic hydrocarbon ring group such as a naphthyl group and an anthracenyl group.
- Examples of the aralkyl group include a benzyl group, a phenylpropyl group, and a naphthylmethyl group.
- heterocyclic group examples include heterocyclic monocycles such as pyrrolyl group, thienyl group, pyridyl group, phenazyl group, pyridazyl group, and acridyl group, and heterocyclic condensed rings.
- Examples of the substituent for R 23 to R 28 in the general formula (4) include a halogen atom, a cyano group, a nitro group, a formyl group, an acetyl group, a benzoyl group, an amide group, a styryl group, an ethynyl group, a phenyl group, a naphthyl group, Examples thereof include monocyclic aromatic rings such as anthranyl groups, polycyclic condensed rings, pyridyl groups, pyridazyl groups, phenazyl groups, pyrrolyl groups, imidazolyl groups, and the like, and polycyclic heterocondensed rings such as quinolyl groups and acridyl groups.
- the condensed ring formed between R 23 and R 24 , R 25 and R 26 and R 27 and R 28 , or R 23 and R 28 , R 24 and R 25, and R 26 and R 27 includes a benzo group, A naphtho group, a pyrido group, etc. are mentioned.
- each R ′ independently represents a hydrogen atom, a substituted or unsubstituted aryl group having 5 to 60 nuclear atoms or an alkyl group having 1 to 50 nuclear atoms. .
- the aryl group having 5 to 60 nucleus atoms in R ′ in the general formulas (5) to (12) includes phenyl group, naphthyl group, biphenylyl group, anthranyl group, phenanthryl group, pyrenyl group, chrysenyl group, fluoranthenyl Group, fluorenyl group, pyridinyl group, quinolyl group, isoquinolyl group, phenanthryl group and the like.
- alkyl group having 1 to 50 nucleus atoms examples include a methyl group, an ethyl group, a butyl group, a pentyl group, a hexyl group, a trifluoromethyl group, and a trifluoroethyl group.
- R ′ in the general formulas (5) to (12) may be substituted, and examples of the substituent include the same substituents as in the general formula (1).
- the material etc. which are used for the below-mentioned positive hole transport layer are mentioned, for example.
- phthalocyanine derivatives represented by copper phthalocyanine, hexaazatriphenylene derivatives as described in JP-T-2003-519432, JP-A-2006-135145, etc. metal oxides represented by vanadium oxide, amorphous Conductive polymers such as carbon, polyaniline (emeraldine) and polythiophene, orthometalated complexes represented by tris (2-phenylpyridine) iridium complex, and triarylamine derivatives are preferred.
- the materials used for the above-described hole injection layer may be used alone or in combination of a plurality of types, but the hole injection layer according to the present invention is preferably composed of a single type of compound. .
- a material system to be introduced into the hole injection layer there are generally three cases as a material system to be introduced into the hole injection layer: (i) an organic compound simple substance, (ii) a metal oxide simple substance, and (iii) an organic compound and a metal, a metal oxide, Alternatively, a p-type doping material such as biferrocene F-TCNQ can be used. From the viewpoint of stability (mass production) of the material itself, the organic compound alone is most desirable as the hole injection layer material. However, in the case of the organic compound alone, the hole transporting layer has a hole transporting property particularly in the hole injection layer portion. There was a drawback that it was lower than the material.
- ⁇ eR 2 v / k B T ⁇ exp ( ⁇ 2 ⁇ R)
- the layer thickness (d HIL ) of the hole injection layer is determined by the layer having hole transportability sandwiched between the semi-transmissive electrode or the charge generation unit and the light emitting layer (for example, the hole injection layer).
- the layer thickness ratio (d HIL / d HL ) is preferably 0.20 or less, and 0.10 or less with respect to the total layer thickness (d HL ) of the hole transport layer, the electron transport layer, etc.
- the thickness of the hole injection layer is preferably in the range of 1 to 15 nm, more preferably in the range of 1 to 10 nm.
- the hole transport layer is made of a material having a function of transporting holes.
- the hole transport layer is a layer having a function of transmitting holes injected from the anode to the light emitting layer.
- the thickness of the hole transport layer is not particularly limited, but is usually in the range of 5 nm to 5 ⁇ m, more preferably in the range of 2 to 500 nm, and still more preferably in the range of 5 to 200 nm. Is within.
- the hole transport layer may be a single layer, two layers, or three layers.
- the material used for the hole transport layer (hereinafter referred to as a hole transport material) only needs to have either a hole injecting property or a transporting property or an electron barrier property.
- a hole transport material an arbitrary material can be selected and used from conventionally known compounds.
- the hole transport material may be used alone or in combination of two or more.
- the hole transport material examples include porphyrin derivatives, phthalocyanine derivatives, oxazole derivatives, oxadiazole derivatives, triazole derivatives, imidazole derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, hydrazone derivatives, stilbene derivatives, polyarylalkane derivatives, Triarylamine derivatives, carbazole derivatives, indolocarbazole derivatives, isoindole derivatives, acene derivatives such as anthracene and naphthalene, fluorene derivatives, fluorenone derivatives, polyvinylcarbazole, polymer materials with aromatic amines introduced in the main chain or side chain Or oligomer, polysilane, conductive polymer or oligomer (for example, PEDOT: PSS, aniline copolymer, polyaniline, polythiol) Emissions, etc.) and the like.
- PEDOT PSS, ani
- triarylamine derivatives examples include a benzidine type typified by ⁇ -NPD, a starburst type typified by MTDATA, and a compound having fluorene or anthracene in the triarylamine linking core part.
- hexaazatriphenylene derivatives described in JP-T-2003-519432 and JP-A-2006-135145 can also be used as the hole transport material.
- a hole transport layer having a high p property doped with impurities can also be used.
- JP-A-4-297076, JP-A-2000-196140, 2001-102175, J. Pat. Appl. Phys. 95, 5773 (2004), etc. can also be applied to the hole transport layer.
- JP-A-11-251067, J. Org. Huang et. al. It is also possible to use so-called p-type hole transport materials and inorganic compounds such as p-type-Si and p-type-SiC, as described in the literature (Applied Physics Letters 80 (2002), p. 139).
- ortho-metalated organometallic complexes having Ir or Pt as the central metal as typified by Ir (ppy) 3 are also preferably used.
- the above-mentioned materials can be used as the hole transport material, a triarylamine derivative, a carbazole derivative, an indolocarbazole derivative, an azatriphenylene derivative, an organometallic complex, or an aromatic amine is introduced into the main chain or side chain.
- the polymer materials or oligomers used are preferably used.
- hole transporting material examples include Appl. Phys. Lett. 69, 2160 (1996), J. MoI. Lumin. 72-74,985 (1997), Appl. Phys. Lett. 78, 673 (2001), Appl. Phys. Lett. 90, 183503 (2007), Appl. Phys. Lett. 90, 183503 (2007), Appl. Phys. Lett. 51, 913 (1987), Synth. Met. 87, 171 (1997), Synth. Met. 91, 209 (1997), Synth. Met. 111, 421 (2000), SID Symposium Digest, 37, 923 (2006), J. Am. Mater. Chem. 3,319 (1993), Adv. Mater.
- the electron blocking layer is a layer having a function of a hole transport layer in a broad sense. Preferably, it is made of a material having a function of transporting holes and a small ability to transport electrons.
- the electron blocking layer can improve the probability of recombination of electrons and holes by blocking electrons while transporting holes.
- the structure of the above-mentioned hole transport layer can be used as an electron blocking layer of an organic EL element as needed.
- the electron blocking layer provided in the organic EL element is preferably provided adjacent to the anode side of the light emitting layer.
- the thickness of the electron blocking layer is preferably in the range of 3 to 100 nm, more preferably in the range of 5 to 30 nm.
- the materials used for the electron blocking layer can be preferably used.
- the material used as the above-mentioned host compound can also be preferably used as the electron blocking layer.
- the hole blocking layer is a layer having a function of an electron transport layer in a broad sense. Preferably, it is made of a material having a function of transporting electrons and a small ability to transport holes. By blocking holes while transporting electrons, the recombination probability of electrons and holes can be improved. It is more effective if the hole blocking layer also has a function as a layer for blocking triplet energy. Moreover, the structure of the below-mentioned electron carrying layer can be used as a hole-blocking layer as needed.
- the hole blocking layer provided in the organic EL element is preferably provided adjacent to the cathode side of the light emitting layer.
- the layer thickness of the hole blocking layer is preferably in the range of 3 to 100 nm, more preferably in the range of 5 to 30 nm.
- the material used for a hole-blocking layer the material used for the below-mentioned electron carrying layer is used preferably, and the material used as the above-mentioned host compound is also preferably used for a hole-blocking layer.
- the electron transport layer used for the organic EL element is made of a material having a function of transporting electrons, and has a function of transmitting electrons injected from the cathode to the light emitting layer.
- the electron transport material may be used alone or in combination of two or more.
- the thickness of the electron transport layer is not particularly limited, but is usually in the range of 2 nm to 5 ⁇ m, more preferably in the range of 2 to 500 nm, and still more preferably in the range of 5 to 200 nm.
- the organic EL element when the light generated in the light emitting layer is extracted, the light extracted directly from the light emitting layer through the anode and the light extracted after being reflected by the cathode positioned opposite to the anode cause interference. It is known. Therefore, in the organic EL device of the present invention, the total thickness of each light emitting unit is adjusted by adjusting the layer having hole transportability (for example, hole injection layer, hole transport layer, electron blocking layer, etc.) and electron transportability. It is preferable to adjust the total layer thickness of the layers (for example, the electron injection layer, the electron transport layer, and the hole blocking layer) appropriately between several nm to several ⁇ m.
- hole transportability for example, hole injection layer, hole transport layer, electron blocking layer, etc.
- electron transportability for example, the electron injection layer, the electron transport layer, and the hole blocking layer
- the electron mobility of the electron transporting layer is 1 ⁇ 10 ⁇ 5 cm 2 / Vs or higher is preferable.
- the material used for the electron transporting layer may have either an electron injecting or transporting property or a hole blocking property. Any one can be selected and used. Examples thereof include nitrogen-containing aromatic heterocyclic derivatives, aromatic hydrocarbon ring derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, silole derivatives, and the like.
- Examples of the nitrogen-containing aromatic heterocyclic derivative include a carbazole derivative, an azacarbazole derivative (one having one or more carbon atoms constituting the carbazole ring substituted with a nitrogen atom), a pyridine derivative, a pyrimidine derivative, a pyrazine derivative, a pyridazine derivative, Examples include triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, azatriphenylene derivatives, oxazole derivatives, thiazole derivatives, oxadiazole derivatives, thiadiazole derivatives, triazole derivatives, benzimidazole derivatives, benzoxazole derivatives, and benzthiazole derivatives.
- Examples of the aromatic hydrocarbon ring derivative include naphthalene derivatives, anthracene derivatives, triphenylene and the like.
- a metal complex having a quinolinol skeleton or a dibenzoquinolinol skeleton as a ligand such as tris (8-quinolinol) aluminum (Alq 3 ), tris (5,7-dichloro-8-quinolinol) aluminum, tris (5,7 -Dibromo-8-quinolinol) aluminum, tris (2-methyl-8-quinolinol) aluminum, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), etc., and their metals
- a metal complex in which the central metal of the complex is replaced with In, Mg, Cu, Ca, Sn, Ga, or Pb can also be used as the electron transport material.
- metal-free or metal phthalocyanine or those having the terminal substituted with an alkyl group or a sulfonic acid group can be preferably used as the electron transporting material.
- a distyrylpyrazine derivative used as a material for the light-emitting layer can also be used as an electron transport material, and an inorganic material such as n-type-Si, n-type-SiC, etc., like the hole injection layer and the hole transport layer.
- a semiconductor can also be used as an electron transport material.
- a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
- a doping material may be doped into the electron transport layer as a guest material to form an electron transport layer having a high n property (electron rich).
- the doping material include metal compounds such as metal complexes and metal halides, and other n-type dopants.
- Specific examples of the electron transport layer having such a structure include, for example, JP-A-4-297076, JP-A-10-270172, JP-A-2000-196140, 2001-102175, J. Pat. Appl. Phys. , 95, 5773 (2004) and the like.
- JP 2008-277810 A JP 2006-156445 A
- JP 2005-340122 A JP 2003-45662 A
- JP 2003-31367 A JP 2003-282270 A.
- More preferable electron transport materials include pyridine derivatives, pyrimidine derivatives, pyrazine derivatives, triazine derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, carbazole derivatives, azacarbazole derivatives, and benzimidazole derivatives.
- the electron injection layer (also referred to as “cathode buffer layer”) is a layer provided between the cathode and the light emitting layer in order to reduce driving voltage and improve light emission luminance.
- An example of an electron injection layer is described in the second chapter, Chapter 2, “Electrode Materials” (pages 123-166) of “Organic EL devices and their industrialization front line (November 30, 1998, NTS luminescence)”. Are listed.
- the electron injection layer is provided as necessary, and as described above, between the cathode or the charge generation unit and the light emitting layer, or between the cathode or the charge generation unit and the electron transport layer.
- the electron injection layer is preferably a very thin film, and depending on the material, the layer thickness is preferably in the range of 0.1 to 5 nm. Moreover, the nonuniform film
- JP-A-6-325871, JP-A-9-17574, and JP-A-10-74586 Specific examples of materials preferably used for the electron injection layer include metals typified by strontium and aluminum, alkali metal compounds typified by lithium fluoride, sodium fluoride, and potassium fluoride, magnesium fluoride, and fluoride. Examples thereof include alkaline earth metal compounds typified by calcium, metal oxides typified by aluminum oxide, metal complexes typified by lithium 8-hydroxyquinolate (Liq), and the like.
- the material used for said electron injection layer may be used independently, and may be used in combination of multiple types.
- a non-light emitting charge generating unit is provided between the light emitting units.
- the charge generation unit is a layer having an interface with an organic compound layer that electrically connects a plurality of light emitting units in series in an electric field.
- an organic compound or an inorganic compound can be used alone or in combination.
- the charge generation unit is composed of at least one layer, preferably two or more layers, and particularly preferably includes one or both of a p-type semiconductor layer and an n-type semiconductor layer.
- the charge generation unit may be a bipolar layer capable of generating and transporting holes and electrons inside the layer by an external electric field.
- metals, metal oxides and alloys thereof that can be used as ordinary electrode materials can be suitably used.
- the charge generation unit can have a structure of a charge generation layer having a function of injecting electrons into one light emitting unit and a function of injecting holes into the other light emitting unit.
- the charge generation unit can be formed using the same material as the semi-transmissive electrode or the reflective electrode, and can be formed using a material having lower conductivity than the semi-transmissive electrode and the reflective electrode. It is.
- an insulator or a semiconductor such as lithium oxide, lithium fluoride, or cesium carbonate can be used as the layer having a function of injecting electrons in the charge generation unit.
- a material obtained by adding an electron donating substance to a substance having a high electron transporting property can be used.
- Organic compounds used in the charge generation unit include nanocarbon materials, organic metal complex compounds that function as organic semiconductor materials (organic acceptors, organic donors), organic salts, aromatic hydrocarbon compounds and derivatives thereof, and heteroaromatic hydrocarbons. Examples thereof include compounds and derivatives thereof. Examples of inorganic compounds include metals, inorganic oxides, and inorganic salts.
- Examples of the substance having a high electron transporting property include tris (8-quinolinolato) aluminum (Alq 3 ), tris (4-methyl-8-quinolinolato) aluminum (Almq 3 ), and bis (10-hydroxybenzo [h] quinolinato).
- a metal complex having a quinoline skeleton or a benzoquinoline skeleton such as beryllium (BeBq 2 ), bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (BAlq), or the like can be used.
- a metal complex having an oxazole-based or thiazole-based ligand such as can also be used.
- 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole PBD
- 1,3-bis [5- (p -Tert-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene OXD-7
- bathophenanthroline BPhen
- bathocuproin BCP
- the substance having a high electron transporting property is a substance mainly having an electron mobility of 1 ⁇ 10 ⁇ 6 cm 2 / Vs or higher. Any substance other than those described above can be used as long as it has a property of transporting more electrons than holes.
- the electron injecting property can be increased by adding an electron donating substance to a substance having a high electron transporting property. For this reason, the drive voltage of a light emitting element can be reduced.
- an alkali metal an alkaline earth metal, a rare earth metal, a metal belonging to Group 13 of the periodic table, an oxide thereof, or a carbonate thereof can be used.
- lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), ytterbium (Yb), indium (In), lithium oxide, cesium carbonate, or the like is preferably used.
- an organic compound such as tetrathianaphthacene may be used as a donor substance.
- the layer having a function of injecting holes in the charge generation unit for example, a semiconductor such as molybdenum oxide, vanadium oxide, rhenium oxide, ruthenium oxide, or an insulator can be used.
- a material in which an electron-accepting substance is added to a substance having a high hole-transport property can be used.
- a layer made of an electron accepting substance may be used.
- Examples of the substance having a high hole transporting property include 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB or ⁇ -NPD), N, N′-bis (3- Methylphenyl) -N, N'-diphenyl- [1,1'-biphenyl] -4,4'-diamine (TPD), 4,4 ', 4 "-tris (N, N-diphenylamino) triphenylamine
- An aromatic amine compound such as (TDATA) or 4,4 ′, 4 ′′ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (MTDATA) can be used.
- the above-described substance having a high hole-transport property is mainly a substance having a hole mobility of 1 ⁇ 10 ⁇ 6 cm 2 / Vs or higher. Any substance other than those described above may be used as long as it has a property of transporting more holes than electrons. Moreover, you may use the above-mentioned host compound.
- the hole-injecting property can be increased by adding an electron-accepting substance to a substance having a high hole-transporting property. For this reason, the drive voltage of a light emitting element can be reduced.
- the electron-accepting substance 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (F4-TCNQ), chloranil, or the like can be used. Transition metal oxides can also be used. In addition, an oxide of a metal belonging to Groups 4 to 8 in the periodic table can be used.
- vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide are preferable because of their high electron accepting properties.
- molybdenum oxide is especially preferable because it is stable in the air, has a low hygroscopic property, and is easy to handle.
- another layer may be introduced between the layer having a function of injecting holes and the layer having a function of injecting electrons, if necessary.
- a conductive layer such as ITO or an electronic relay layer may be provided.
- the electron relay layer has a function of reducing voltage loss generated between a layer having a function of injecting holes and a layer having a function of injecting electrons.
- a material having a LUMO level of about ⁇ 5.0 eV or more, and it is more preferable to use a material having a range of ⁇ 5.0 to ⁇ 3.0 eV.
- PTCDA 3,4,9,10-perylenetetracarboxylic dianhydride
- PTCBI 3,4,9,10-perylenetetracarboxylic bisbenzimidazole
- the light emitting unit constituting the organic EL element may further contain other additives.
- the additive include halogen elements and halogenated compounds such as bromine, iodine, and chlorine, alkali metals and alkaline earth metals such as Pd, Ca, and Na, transition metal compounds, complexes, and salts.
- the content of the additive can be arbitrarily determined, but is preferably 1000 ppm or less, more preferably 500 ppm or less, still more preferably 50 ppm or less, based on the total mass% of the contained layer. . However, it is not within this range depending on the purpose of improving the transportability of electrons and holes or the purpose of favoring the exciton energy transfer.
- an electrode substance made of a metal, an alloy, an electrically conductive compound, and a mixture thereof having a high work function (4 eV or more, preferably 4.3 eV or more) is used. Specifically, it contains silver (Ag), aluminum (Al), indium tin oxide (ITO), indium tin oxide containing silicon oxide (hereinafter also referred to as ITSO), and 2 to 20% zinc oxide.
- the semi-transmissive electrode may be formed by forming a thin electrode material film using a method such as vapor deposition or sputtering, and forming a pattern having a desired shape by a photolithography method. Further, when pattern accuracy is not so required (about 100 ⁇ m or more), a pattern may be formed through a mask having a desired shape when the electrode material is deposited or sputtered. In the case of using a coatable material such as an organic conductive compound, a wet film forming method such as a printing method or a coating method can also be used.
- the light transmittance of the semi-transmissive electrode is preferably in the range of 10 to 100% at a wavelength of 450 nm, and the light reflectance is preferably in the range of 5 to 80%.
- the sheet resistance as a semi-transmissive electrode is several hundred ⁇ / sq. The following is preferred. Further, although the thickness of the semi-transmissive electrode depends on the material, it is usually selected within the range of 10 nm to 1 ⁇ m, preferably 10 nm to 200 nm.
- the semi-transmissive electrode in the case where translucency is required for the semi-transmissive electrode, there is a configuration in which the above-described metal material is thinned and formed so as to have semi-transparency, and the translucent material is laminated thereon.
- a semi-permeable metal material may be used in a single layer.
- the material of the semi-transmissive electrode is not limited to these.
- the film thickness of the metal material is preferably in the range of 1 to 50 nm, more preferably in the range of 5 to 40 nm. 5 nm or more is desirable from the viewpoint of film thickness stability and film quality of the metal material, and the resonance mechanism depending on the film thickness of the metal material is strengthened, but 40 nm or less is desirable from the viewpoint of extracting light emitted from the inside.
- Electrode substance made of a metal having a small work function (4 eV or less) (referred to as an electron injecting metal), an alloy, an electrically conductive compound, or a mixture thereof is used.
- electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) Mixtures, indium, lithium / aluminum mixtures, aluminum, silver, silver-based alloys, aluminum / silver mixtures, rare earth metals, and the like.
- the reflective electrode can be produced by using the above electrode material by vapor deposition or sputtering.
- the sheet resistance of the reflective electrode is several hundred ⁇ / sq. The following is preferred.
- the thickness of the reflective electrode is usually selected in the range of 10 nm to 5 ⁇ m, preferably in the range of 50 to 200 nm.
- the substrate used for the organic EL element is not particularly limited in the type such as glass and plastic, and may be transparent or opaque. When extracting light from the substrate side, the substrate is preferably transparent. Preferred examples of the transparent substrate include glass, quartz, and a transparent resin film. Particularly preferred is a resin film capable of giving flexibility to the organic EL element.
- polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), polyethylene, polypropylene, cellophane, cellulose diacetate, cellulose triacetate (TAC), cellulose acetate butyrate, cellulose acetate propionate ( CAP), cellulose esters such as cellulose acetate phthalate, cellulose nitrate or derivatives thereof, polyvinylidene chloride, polyvinyl alcohol, polyethylene vinyl alcohol, syndiotactic polystyrene, polycarbonate, norbornene resin, polymethylpentene, polyether ketone, polyimide , Polyethersulfone (PES), polyphenylene sulfide, polysulfones Cycloolefin resins such as polyetherimide, polyetherketoneimide, polyamide, fluororesin, nylon, polymethylmethacrylate, acrylic or polyarylate, Arton (trade name, manufactured by JSR) or Appel (trade name, manufactured by J
- a gas barrier film may be formed on the surface of the resin film by using an inorganic film, an organic film, or a hybrid film of both.
- the gas barrier membrane has a water vapor permeability (25 ⁇ 0.5 ° C., relative humidity (90 ⁇ 2)% RH) measured by a method according to JIS K 7129-1992, 0.01 g / (m 2 ⁇ 24 h). )
- the following gas barrier films are preferred.
- the oxygen permeability measured by a method according to JIS K 7126-1987 is 1 ⁇ 10 ⁇ 3 ml / (m 2 ⁇ 24 h ⁇ atm) or less, and the water vapor permeability is 1 ⁇ 10 ⁇ 5 g / A high gas barrier film of (m 2 ⁇ 24 h) or less is preferable.
- any material may be used as long as it has a function of suppressing intrusion of elements that cause deterioration of elements such as moisture and oxygen.
- silicon oxide, silicon dioxide, silicon nitride, or the like can be used.
- the method for forming the gas barrier film is not particularly limited.
- the vacuum deposition method, sputtering method, reactive sputtering method, molecular beam epitaxy method, cluster ion beam method, ion plating method, plasma polymerization method, atmospheric pressure plasma weight A combination method, a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or the like can be used.
- an atmospheric pressure plasma polymerization method as described in JP-A-2004-68143 is preferable.
- the opaque support substrate examples include metal plates / films such as aluminum and stainless steel, opaque resin substrates, ceramic substrates, and the like.
- sealing means used for sealing the organic EL element include a method of bonding a sealing member, an electrode, and a substrate with an adhesive.
- a sealing member it should just be arrange
- transparency and electrical insulation are not particularly limited.
- Specific examples include a glass plate, a polymer plate, a polymer film, a metal plate / film, and the like.
- the glass plate include soda-lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz.
- the polymer plate and polymer film include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, and polysulfone.
- the metal plate include metals including one or more selected from the group consisting of stainless steel, iron, copper, aluminum, magnesium, nickel, zinc, chromium, titanium, molybdenum, silicon, germanium, and tantalum, and alloys.
- the polymer film preferably has an oxygen permeability of 1 ⁇ 10 ⁇ 3 ml / (m 2 ⁇ 24 h ⁇ atm) or less and a water vapor permeability of 1 ⁇ 10 ⁇ 3 g / (m 2 ⁇ 24 h) or less. More preferably, the water vapor permeability is 1 ⁇ 10 ⁇ 5 g / (m 2 ⁇ 24 h) or less and the oxygen permeability is 1 ⁇ 10 ⁇ 5 ml / (m 2 ⁇ 24 h ⁇ atm) or less.
- adhesives include photo-curing and thermosetting adhesives having reactive vinyl groups such as acrylic acid oligomers and methacrylic acid oligomers, and moisture curing adhesives such as 2-cyanoacrylates.
- photo-curing and thermosetting adhesives having reactive vinyl groups such as acrylic acid oligomers and methacrylic acid oligomers, and moisture curing adhesives such as 2-cyanoacrylates.
- fever and chemical-curing types (2 liquid mixing), such as an epoxy type can be mentioned.
- hot-melt type polyamide, polyester, and polyolefin can be mentioned.
- a cationic curing type ultraviolet curing epoxy resin adhesive can be mentioned.
- an organic EL element may deteriorate by heat processing, it is preferable that it can be adhesively cured from room temperature (25 ° C.) to 80 ° C. Further, a desiccant may be dispersed in the adhesive.
- coating of the adhesive agent to a sealing part may use commercially available dispenser, and may print it like screen printing.
- an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil is injected in the gas phase and the liquid phase.
- a vacuum can also be used.
- a hygroscopic compound can also be enclosed inside.
- hygroscopic compound examples include metal oxides (for example, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide) and sulfates (for example, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate).
- metal oxides for example, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide
- sulfates for example, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate.
- metal halides eg calcium chloride, magnesium chloride, cesium fluoride, tantalum fluoride, cerium bromide, magnesium bromide, barium iodide, magnesium iodide etc.
- perchloric acids eg perchloric acid Barium, magnesium perchlorate, and the like
- anhydrous salts are preferably used in sulfates, metal halides, and perchloric acids.
- a protective film or a protective plate may be provided outside the sealing film.
- the mechanical strength is not necessarily high, and thus it is preferable to provide such a protective film and a protective plate.
- the same glass plate, polymer plate / film, metal plate / film, etc. as those used for the sealing can be used, but the polymer film is light and thin. Is preferably used.
- An organic EL element emits light inside a layer having a higher refractive index than air (within a refractive index of about 1.6 to 2.1), and only about 15 to 20% of the light generated in the light emitting layer is emitted. It is generally said that it cannot be taken out. This is because light incident on the interface (interface between the transparent substrate and air) at an angle ⁇ greater than the critical angle causes total reflection and cannot be taken out of the element, or between the transparent electrode or light emitting layer and the transparent substrate. This is because the light undergoes total reflection between the light, the light is guided through the transparent electrode or the light emitting layer, and as a result, the light escapes in the side surface direction of the element.
- a method for improving the light extraction efficiency for example, a method of forming irregularities on the surface of the transparent substrate to prevent total reflection at the transparent substrate and the air interface (for example, US Pat. No. 4,774,435), A method for improving efficiency by providing light condensing property (for example, Japanese Patent Laid-Open No. 63-134795), a method for forming a reflective surface on the side surface of an element (for example, Japanese Patent Laid-Open No. 1-220394), a substrate A method of forming an antireflection film by introducing a flat layer having an intermediate refractive index between the substrate and the light emitter (for example, Japanese Patent Laid-Open No. Sho 62-172691), lower than the substrate between the substrate and the light emitter.
- a method of introducing a flat layer having a refractive index for example, Japanese Patent Application Laid-Open No. 2001-202827, and forming a diffraction grating between any one of a substrate, a transparent electrode layer and a light emitting layer (including between the substrate and the outside).
- Method JP etc. 1-283751 can be mentioned.
- a desired electrode material for example, a thin film made of an anode material is formed on a suitable substrate by a method such as vapor deposition or sputtering so as to have a film thickness of 1 ⁇ m or less, preferably 10 to 200 nm, and is semi-transparent. An electrode is produced.
- a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron injection layer, and an electron transport layer are formed thereon as a first light emitting unit.
- a vapor deposition method, a wet process spin coating method, casting method, ink jet method, printing method, LB method (Langmuir-Blodget method), spray method, printing method, slot type coater
- the vacuum deposition method, spin coating method, ink jet method, printing method, and slot type coater method are particularly preferred from the standpoint that a homogeneous film can be easily obtained and pinholes are hardly formed. Different film formation methods may be applied for each layer.
- the vapor deposition conditions vary depending on the type of compound used, but generally the boat heating temperature is 50 to 450 ° C., the degree of vacuum is 1 ⁇ 10 ⁇ 6 to 1 ⁇ 10 ⁇ 2 Pa, and the vapor deposition rate. It is desirable to select appropriately within a range of 0.01 to 50 nm / second, a substrate temperature of ⁇ 50 ° C. to 300 ° C., and a layer thickness of 0.1 nm to 5 ⁇ m, preferably 5 to 200 nm.
- a charge generation unit is formed on the first light emitting unit.
- the method for forming the charge generation unit is not particularly limited as long as it is a method capable of forming a thin film. For example, vapor deposition, sputtering, wet process (spin coating method, casting method, ink jet method, LB method, spray method, printing method) Slot type coater method).
- a second light emitting unit is formed on the charge generation unit in the same manner as the first light emitting unit.
- a thin film made of, for example, a cathode material is formed thereon by a method such as vapor deposition or sputtering so as to have a film thickness of 1 ⁇ m or less, preferably in the range of 50 to 200 nm, and a reflective electrode is provided. . Thereby, a desired organic EL element is obtained.
- the organic EL element is manufactured from the first light emitting unit to the reflective electrode consistently by one evacuation, it may be taken out halfway and subjected to different film forming methods. At that time, it is necessary to consider that the work is performed in a dry inert gas atmosphere.
- the organic EL element may be sealed and protected.
- the organic EL element is covered with a thermosetting resin in a state where part or all of the semi-transmissive electrode and the reflective electrode are exposed, and this is heat-cured to seal the organic EL element.
- the organic EL element sealing body and a part or all of the semi-transmissive electrode and the reflective electrode of the organic EL element exposed therefrom are covered with a protective member, and the overlapping part of the protective member is heated at a predetermined temperature. Crimp.
- Two protective members may be overlapped to cover an organic EL element sealing body, and the side edges may be heat-pressed together, or one protective member may be folded to seal an organic EL element sealing body, etc. And the side edge portions (particularly, the open ends) may be thermocompression-bonded.
- the organic EL module which sealed and protected the organic EL element by the above process is manufactured.
- the bottom emission type organic EL element in which the semi-transmissive electrode, the first light emitting unit, the charge generating unit, the second light emitting unit, and the reflective electrode are laminated in this order from the substrate side.
- the present invention is not limited to this configuration.
- the stacking order of the layers may be reversed, the semi-transmissive electrode and the reflective electrode may be reversed, and it is sufficient that at least two light emitting layers are provided.
- the layer configuration and the number of stacked layers of the light emitting layer are not particularly limited, and a configuration capable of realizing a desired organic EL element can be obtained.
- the light emitting layer constituting the organic EL element may be two layers, or three or more light emitting layers may be laminated.
- a single light emitting material may be used, or a plurality of light emitting layers may be laminated directly or via an organic layer. A combination of these may be used as appropriate.
- the organic EL element used in the lighting device may be designed such that the organic EL element having the above-described configuration has a resonator structure.
- Examples of the purpose of use of the organic EL element configured as a resonator structure include, but are not limited to, a light source of an optical storage medium, a light source of an electrophotographic copying machine, a light source of an optical communication processor, a light source of an optical sensor, and the like. .
- the combination of light emitting materials may be a combination of a plurality of phosphorescent or fluorescent materials, or a combination of a light emitting material that emits light by fluorescence or phosphorescence and a dye material that emits light from the light emitting material as excitation light. Good.
- a plurality of light emitting dopants may be used in combination in the light emitting layer.
- Such an organic EL element is different from a structure in which organic EL elements emitting light of each color are individually arranged in parallel to obtain light emission, and the organic EL element itself emits light. For this reason, a mask is not required for the formation of most layers constituting the element, and for example, a conductive layer can be formed on one surface by vapor deposition, casting, spin coating, ink jet, printing, etc., and productivity is improved. . If the organic EL element demonstrated above is used, it is possible to produce the illuminating device whose emitted light color is substantially the same color system.
- the lighting device can increase the area of the light emitting surface by using, for example, a plurality of organic EL elements.
- the light emitting surface is enlarged by arranging a plurality of light emitting panels provided with organic EL elements on the substrate on the support substrate (that is, tiling).
- the support substrate may also serve as a sealing material, and each light emitting panel is tiled in a state where the organic EL element is sandwiched between the support substrate and the substrate of the light emitting panel.
- An adhesive may be filled between the support substrate and the organic EL element may be sealed by this. Note that the terminals of the semi-transmissive electrode and the reflective electrode are exposed around the light-emitting panel.
- the center of each light emitting panel is a light emitting region, and a non-light emitting region is generated between the light emitting panels.
- a light extraction member for increasing the amount of light extracted from the non-light emitting area may be provided in the non-light emitting area of the light extraction surface.
- a light collecting sheet or a light diffusion sheet can be used as the light extraction member.
- a hole transporting layer was formed by laminating Exemplary Compound HI-145, Compound 1-A, and Compound 1-B from the anode side.
- a compound 3 having the following structural formula was vapor-deposited such that 86 vol% and LiF were 14 vol% to form a layer having a thickness of 10 nm. Furthermore, it vapor-deposited so that the compound 3 might be 98 vol% and Li might be 2 vol%, and the layer with a layer thickness of 10 nm was formed.
- This formed the 2nd electron carrying layer (it serves as an electron injection layer) comprised from two layers, the layer which consists of a compound 3 and LiF, and the layer which consists of a compound 3 and Li.
- a first light emitting unit composed of the first hole injection layer, the first hole transport layer, the first electron blocking layer, the first light emitting layer, and the first electron transport layer was produced.
- a hole transporting layer was formed by laminating Exemplary Compound HI-145, Compound 1-A, and Compound 1-B from the charge generation unit side.
- the compound 3 was deposited so as to be 86 vol% and LiF was 14 vol%. Formed. Furthermore, it vapor-deposited so that the compound 3 might be 98 vol% and Li might be 2 vol%, and the layer with a layer thickness of 10 nm was formed. This formed the 2nd electron carrying layer comprised from two layers, the layer which consists of a compound 3 and LiF, and the layer which consists of a compound 3 and Li.
- the organic EL element was sealed by irradiating UV light from the glass case side to cure the sealing material, and the organic EL element 101 was produced.
- the sealing operation with the glass case was performed in a glove box under a nitrogen atmosphere (in an atmosphere of high-purity nitrogen gas having a purity of 99.999% or more) without bringing the organic EL element into contact with the atmosphere.
- organic EL element 201 (yellow type)
- the thickness of the first hole transport layer was 55 nm
- the thickness of the second hole transport layer was 75 nm
- the first and second light emitting layers were formed as follows.
- the organic EL element 201 was produced.
- a second phosphorescent light emitting layer having a layer thickness of 20 nm was formed.
- organic EL element 202 (yellow type)
- the organic EL element 202 was produced in the same manner except that the layer thickness of the second hole transport layer was changed to 85 nm.
- a second fluorescent light emitting layer having a thickness of 20 nm was formed.
- the organic EL element of the present invention is superior in power efficiency, normal temperature life, and driving life at 85 ° C. as compared with the organic EL element of the comparative example.
- the lambda N + 1 the difference between the (max) ( ⁇ N + 1 (max) - ⁇ N (max)), be in the range of 1 ⁇ 50 nm prove useful.
- the present invention can be particularly suitably used for providing an organic EL element having a high efficiency and a long lifetime.
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Abstract
Description
前記半透過性電極側からN番目の発光ユニットの発光層と(N+1)番目の発光ユニットの発光層とには、発光色が同色系である発光ドーパントが含有され、
前記N番目の発光ユニットの発光層における発光ドーパントのエレクトロルミネッセンススペクトルの最大発光極大波長λN(max)と、前記(N+1)番目の発光ユニットの発光層における発光ドーパントのエレクトロルミネッセンススペクトルの最大発光極大波長λN+1(max)とが、下記条件式(1)を満たすことを特徴とする有機エレクトロルミネッセンス素子。
nN+1:前記半透過性電極と前記(N+1)番目の発光ユニットの発光層との間に挟持される全ての層の屈折率
dN(nm):前記半透過性電極から前記N番目の発光ユニットの発光層までの実距離
dN+1(nm):前記半透過性電極から前記(N+1)番目の発光ユニットの発光層までの実距離
mN:0以上の整数
mN+1:1以上の整数)
本発明の有機EL素子は、一対の半透過性電極(陽極ともいう。)と反射性電極(陰極ともいう。)間に、複数の発光ユニットを有し、各発光ユニット間には、電荷発生ユニットが形成され、半透過性電極側からN番目の発光ユニットの発光層と(N+1)番目の発光ユニットの発光層とには、発光色が同色系である発光ドーパントが含有され、N番目の発光ユニットの発光層における発光ドーパントのELスペクトルの最大発光極大波長λN(max)と、(N+1)番目の発光ユニットの発光層における発光ドーパントのELスペクトルの最大発光極大波長λN+1(max)とが、下記条件式(1)を満たすことを特徴とする。
nN+1:前記半透過性電極と前記(N+1)番目の発光ユニットの発光層との間に挟持される全ての層の屈折率
dN(nm):前記半透過性電極から前記N番目の発光ユニットの発光層までの実距離
dN+1(nm):前記半透過性電極から前記(N+1)番目の発光ユニットの発光層までの実距離
mN:0以上の整数
mN+1:1以上の整数)
有機EL素子1は、発光層4b及び8bに少なくとも発光性の有機材料を含み、例えば、発光性の有機材料として、青(B)、緑(G)及び赤(R)等の中から、同色系の発光ドーパントを含む複数の発光層を有する発光素子である。
有機EL素子1は、半透過性電極2側から光を取り出す、いわゆるボトムエミッション型の構成である。
光学距離は、発光層と半透過性電極間のいずれかの層、例えば、正孔輸送性を有する層4a及び8a、発光層4b、電子輸送性を有する層4c等の層厚を適宜変更することにより、調整される。
屈折率及び層厚は、例えば、分光エリプソメータとして、堀場JYOBIN-YVON製UVSEL/FUV-FGMS、あるいは、反射分光膜厚計として、大塚電子製FE3000を使用することにより、測定することができる。解析は、波長500~800nmの範囲内にて、Cauchy(n(屈折率):可変、k(減衰係数):なしで固定)で実施して、屈折率及び層厚を測定する。
また、屈折率及び光学距離は、測定対象となる層をシリコンウエハ上に成膜し測定してもよいし、素子あるいはパネル作製後に、集束イオンビーム(Focused Ion Beam:FIB)等で所定の膜分を分離しても測定してもよい。
(II)半透過性電極/第1発光ユニット/電荷発生ユニット/第2発光ユニット/電荷発生ユニット/第3発光ユニット/反射性電極
(III)半透過性電極/第1発光ユニット/電荷発生ユニット/第2発光ユニット/電荷発生ユニット/第3発光ユニット/電荷発生ユニット/第4発光ユニット/反射性電極
(IV)半透過性電極/第1発光ユニット/電荷発生ユニット/第2発光ユニット/電荷発生ユニット/第3発光ユニット/電荷発生ユニット/第4発光ユニット/電荷発生ユニット/第5発光ユニット/反射性電極
(ii)(半透過性電極側)/正孔輸送層/発光層/電子輸送層/(反射性電極側)
(iii)(半透過性電極側)/正孔輸送層/発光層/電子輸送層/電子注入層/(反射性電極側)
(iv)(半透過性電極側)/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/(反射性電極側)
また、異なる第2や第3の正孔輸送層や電子輸送層が形成されていてもよい。
以上の素子構成では、Nが1~4の整数である場合、すなわち、発光ユニット数が2~5である場合を例示したが、発光ユニット数は6以上でもよい。
本発明の有機EL素子は、少なくとも発光色が同色系である発光層を有する、連続した二つの発光ユニットを有している。発光ユニットを三つ以上有する場合、全ての発光層の発光色が同色系であることが好ましい。
発光ユニットは、発光層の他、適宜、正孔注入層、正孔輸送層、電子阻止層、正孔阻止層、電子輸送層、電子注入層等の有機層を有していてもよい。
発光層は、電極又は隣接層から注入される電子と正孔とが再結合し、励起子を経由して発光する場を提供する、発光性の有機半導体薄膜を含む層である。発光する部分は、発光層の層内であっても発光層と隣接層との界面であってもよい。
発光層には、リン光発光材料と蛍光発光材料とを混在させてもよいが、好ましくは発光層をリン光発光材料又は蛍光発光材料のみで構成することが好ましい。
蛍光発光層及びリン光発光層は、ホスト-ドーパント型の発光層であることが好ましい。
発光層の層厚の総和は、特に制限はないが、形成する膜の均質性や、発光時に不必要な高電圧を印加するのを防止し、かつ、駆動電流に対する発光色の安定性向上の観点から、5~200nmの範囲内に調整することが好ましく、更に好ましくは10~150nmの範囲内に調整される。また、個々の発光層の層厚としては、5~200nmの範囲内に調整することが好ましく、更に好ましくは10~40nmの範囲内に調整することである。
発光ドーパントとしては、蛍光発光性ドーパント(蛍光ドーパント、蛍光性化合物ともいう。)、及び、リン光発光性ドーパント(リン光ドーパント、リン光性化合物ともいう。)が好ましく用いられる。発光層中の発光ドーパントの濃度については、使用される特定のドーパント及びデバイスの必要条件に基づいて任意に決定することができる。発光ドーパントの濃度は、発光層の層厚方向に対し、均一な濃度で含有されていてもよく、また任意の濃度分布を有していてもよい。
リン光発光性ドーパントは、励起三重項からの発光が観測される化合物であり、具体的には、室温(25℃)にてリン光発光する化合物であり、25℃においてリン光量子収率が0.01以上の化合物である。発光層に用いるリン光発光性ドーパントにおいて、好ましいリン光量子収率は0.1以上である。
リン光量子収率は、第4版実験化学講座7の分光IIの398頁(1992年版、丸善)に記載の方法により測定できる。溶液中でのリン光量子収率は、種々の溶媒を用いて測定できる。発光層に用いるリン光発光性ドーパントは、任意の溶媒のいずれかにおいて上記リン光量子収率(0.01以上)が達成されればよい。
一つは、キャリアが輸送されるホスト化合物上で、キャリアの再結合によるホスト化合物の励起状態が生成される。このエネルギーをリン光発光性ドーパントに移動させることでリン光発光性ドーパントからの発光を得るというエネルギー移動型である。もう一つは、リン光発光性ドーパントがキャリアトラップとなり、リン光発光性ドーパント上でキャリアの再結合が起こり、リン光発光性ドーパントからの発光が得られるというキャリアトラップ型である。いずれの場合においても、リン光発光性ドーパントの励起状態のエネルギーは、ホスト化合物の励起状態のエネルギーよりも低いことが条件となる。
公知のリン光発光性ドーパントの具体例としては、Nature 395,151(1998)、Appl.Phys.Lett.78,1622(2001)、Adv.Mater.19,739(2007)、Chem.Mater.17,3532(2005)、Adv.Mater.17,1059(2005)、国際公開第2009/100991号、国際公開第2008/101842号、国際公開第2003/040257号、米国特許出願公開第2006/835469号明細書、米国特許出願公開第2006/0202194号明細書、米国特許出願公開第2007/0087321号明細書、米国特許出願公開第2005/0244673号明細書、Inorg.Chem.40,1704(2001)、Chem.Mater.16,2480(2004)、Adv.Mater.16,2003(2004)、Angew.Chem.lnt.Ed.2006,45,7800、Appl.Phys.Lett.86,153505(2005)、Chem.Lett.34,592(2005)、Chem.Commun.2906(2005)、Inorg.Chem.42,1248(2003)、国際公開第2009/050290号、国際公開第2002/015645号、国際公開第2009/000673号、米国特許出願公開第2002/0034656号明細書、米国特許第7332232号明細書、米国特許出願公開第2009/0108737号明細書、米国特許出願公開第2009/0039776号明細書、米国特許第6921915号明細書、米国特許第6687266号明細書、米国特許出願公開第2007/0190359号明細書、米国特許出願公開第2006/0008670号明細書、米国特許出願公開第2009/0165846号明細書、米国特許出願公開第2008/0015355号明細書、米国特許第7250226号明細書、米国特許第7396598号明細書、米国特許出願公開第2006/0263635号明細書、米国特許出願公開第2003/0138657号明細書、米国特許出願公開第2003/0152802号明細書、米国特許第7090928号明細書、Angew.Chem.lnt.Ed.47,1(2008)、Chem.Mater.18,5119(2006)、Inorg.Chem.46,4308(2007)、Organometallics 23,3745(2004)、Appl.Phys.Lett.74,1361(1999)、国際公開第2002/002714号、国際公開第2006/009024号、国際公開第2006/056418号、国際公開第2005/019373号、国際公開第2005/123873号、国際公開第2005/123873号、国際公開第2007/004380号、国際公開第2006/082742号、米国特許出願公開第2006/0251923号明細書、米国特許出願公開第2005/0260441号明細書、米国特許第7393599号明細書、米国特許第7534505号明細書、米国特許第7445855号明細書、米国特許出願公開第2007/0190359号明細書、米国特許出願公開第2008/0297033号明細書、米国特許第7338722号明細書、米国特許出願公開第2002/0134984号明細書、米国特許第7279704号明細書、米国特許出願公開第2006/098120号明細書、米国特許出願公開第2006/103874号明細書、国際公開第2005/076380号、国際公開第2010/032663号、国際公開第第2008/140115号、国際公開第2007/052431号、国際公開第2011/134013号、国際公開第2011/157339号、国際公開第2010/086089号、国際公開第2009/113646号、国際公開第2012/020327号、国際公開第2011/051404号、国際公開第2011/004639号、国際公開第2011/073149号、米国特許出願公開第2012/228583号明細書、米国特許出願公開第2012/212126号明細書、特開2012-069737号公報、特開2012-195554号公報、特開2009-114086号公報、特開2003-81988号公報、特開2002-302671号公報、特開2002-363552号公報等に記載の化合物が挙げられる。
特に、リン光発光性ドーパントとして、特開2013-4245号公報の段落[0185]~[0235]に記載の一般式(4)、一般式(5)、一般式(6)で表される構造を有する化合物、及び、例示化合物(Pt-1~Pt-3、Os-1及びIr-1~Ir-45)を好ましく挙げることができる。
蛍光発光性ドーパントは、励起一重項からの発光が可能な化合物であり、励起一重項からの発光が観測される限り特に限定されない。
ホスト化合物は、発光層において主に電荷の注入及び輸送を担う化合物であり、有機EL素子においてそれ自体の発光は実質的に観測されない。
好ましくは室温(25℃)においてリン光発光のリン光量子収率が、0.1未満の化合物であり、更に好ましくは、リン光量子収率が0.01未満の化合物である。また、発光層に含有される化合物のうちで、その層中での質量比が20%以上であることが好ましい。
ここで、ガラス転移点(Tg)とは、DSC(Differential Scanning Calorimetry:示差走査熱量法)を用いて、JIS K 7121に準拠した方法により求められる値である。
正孔注入層(「陽極バッファー層」ともいう。)は、駆動電圧低減や発光輝度向上のために陽極と発光層との間に設けられる層である。正孔注入層の一例は、「有機EL素子とその工業化最前線(1998年11月30日エヌ・ティー・エス社発行)」の第2編第2章「電極材料」(123~166頁)に記載されている。
正孔注入層は、必要に応じて設けられ、上述のように陽極又は電荷発生ユニットと、発光層又は正孔輸送層との間に設けられる。
正孔注入層は、特開平9-45479号公報、同9-260062号公報、同8-288069号公報等にもその詳細が記載されている。
正孔注入層の構成材料としては、下記一般式(1)で表される構造を有する化合物を好適に用いることができる。
アリール基としては、フェニル基などの単環式芳香族炭化水素環基、及びナフチル基、アントラセニル基、ピレニル基、ペリレニル基などの多環式芳香族炭化水素環基などを挙げることができる。
アラルキル基としては、フェニル基、ビフェニル基、ナフチル基、テルフェニル基、アントラセニル基、ピレニル基、ペリレニル基などのような芳香族炭化水素環基で置換された炭素数1~20であるアルキル基を挙げることができる。
アルキルアミノ基としては、炭素数1~20である脂肪族炭化水素に置換されたアミノ基を挙げることができる。
アリールアミノ基としては、フェニル基、ビフェニル基、ナフチル基、テルフェニル基、アントラセニル基、ピレニル基、ペリレニル基などのような芳香族炭化水素環基で置換されたアミノ基を挙げることができる。
アラルキルアミノ基としては、フェニル基、ビフェニル基、ナフチル基、テルフェニル基、アントラセニル基、ピレニル基、ペリレニル基などのような芳香族炭化水素環基と炭素数1~20である脂肪族炭化水素で置換されたアミノ基を挙げることができる。
複素環基としては、ピロリル基、チエニル基、インドリル基、オキサゾリル基、イミダゾリル基、チアゾリル基、ピリジル基、ピリミジニル基、ピペラジニル基、チオフェニル基、フラニル基、ピリダジニル基などが挙げられる。
アリール基としては、フェニル基などの単環式芳香族炭化水素環基、及びナフチル基、アントラセニル基、ピレニル基、ペリレニル基などの多環式芳香族炭化水素環基などを挙げることができる。
5~7員の複素環基としては、ピロリル基、チエニル基、インドリル基、オキサゾリル基、イミダゾリル基、チアゾリル基、ピリジル基、ピリミジニル基、ピペラジニル基、チオフェニル基、フラニル基、ピリダジニル基等が挙げられる。
6員の芳香族複素環としては、ピリジン環、ピリダジン環、ピリミジン環、ピラジン環、トリアジン環等が挙げられる。
アリールオキシ基としては、フェノキシ基、4-tert-ブチルフェノキシ基、1-ナフチルオキシ基、2-ナフチルオキシ基、9-アンスリルオキシ基、2-フェナントリルオキシ基、1-ナフタセニル基、1-ピレニル基、2-クリセニル基、3-ペリレニル基、1-ペンタセニル基といった炭素数6~30のアリールオキシ基が挙げられる。
アルキルチオ基としては、メチルチオ基、エチルチオ基、プロピルチオ基、ブチルチオ基、イソブチルチオ基、tert-ブチルチオ基、ペンチルチオ基、イソペンチルチオ基、ヘキシルチオ基、イソヘキシルチオ基、ヘプチル基、オクチルチオ基といった炭素数1~18のアルキルチオ基が挙げられる。
アリールチオ基としては、フェニルチオ基、4-メチルフェニルチオ基、4-tert-ブチルフェニルチオ基、1-ナフチルチオといった炭素数6~30のアリールチオ基が挙げられる。
アシル基としては、アセチル基、プロピオニル基、ピバロイル基、シクロヘキシルカルボニル基、ベンゾイル基、トルオイル基、アニソイル基、シンナモイル基等の炭素数2~18のアシル基が挙げられる。
アルコキシカルボニル基としては、メトキシカルボニル基、エトキシカルボニル基、プロポキシカルボニル基、ブトキシカルビニル基、ペンチルオキシカルボニル基、ヘキシルオキシカルボニル基、ヘプチルオキシカルボニル基、オクチルオキシカルボニル基、ベンジルオキシカルボニル基等の炭素数2~18のアルコキシカルボニル基が挙げられる。
アリールオキシカルボニル基としては、フェノキシカルボニル基、1-ナフチルオキシカルボニル基、2-フェナントリルオキシカルボニル基等の炭素数7~30のアリールオキシカルボニル基が挙げられる。
アルキルスルホニル基としては、メシル基、エチルスルホニル基、プロピルスルホニル基、ブチルスルホニル基、ペンチルスルホニル基、ヘキシルスルホニル基、ヘプチルスルホニル基、オクチルスルホニル基、ノニルスルホニル基等の炭素数1~18のアルキルスルホニル基が挙げられる。
アリールスルホニル基としては、ベンゼンスルホニル基、p-トルエンスルホニル基、1-ナフチルスルホニル基等の炭素数6~30のアリールスルホニル基が挙げられる。
脂肪族炭化水素基としては、アルキル基(例えば、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、sec-ブチル基、tert-ブチル基、ペンチル基、イソペンチル基、ヘキシル基、イソヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基、ドデシル基、ペンタデシル基、オクタデシル基といった炭素数1~18のアルキル基)、アルケニル基(例えば、ビニル基、1-プロペニル基、2-プロペニル基、イソプロペニル基、1-ブテニル基、2-ブテニル基、3-ブテニル基、1-オクテニル基、1-デセニル基、1-オクタデセニル基といった炭素数2~18のアルケニル基)、アルキニル基(例えば、エチニル基、1-プロピニル基、2-プロピニル基、1-ブチニル基、2-ブチニル基、3-ブチニル基、1-オクチニル基、1-デシニル基、1-オクタデシニル基といった炭素数2~18のアルキニル基)、シクロアルキル基(例えば、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基、シクロオクタデシル基、2-ボルニル基、2-イソボルニル基、1-アダマンチル基といった炭素数3~18のシクロアルキル基)等の炭素数1~18の1価の脂肪族炭化水素基が挙げられる。
芳香族炭化水素環基としては、1-ナフチル基、2-ナフチル基、1-アンスリル基、2-アンスリル基、5-アンスリル基、1-フェナンスリル基、9-フェナンスリル基、1-アセナフチル基、2-トリフェニレニル基、1-クリセニル基、2-アズレニル基、1-ピレニル基、2-トリフェニレル基、1-ピレニル基、2-ピレニル基、1-ペリレニル基、2-ペリレニル基、3-ペリレニル基、2-インデニル基、1-アセナフチレニル基、2-ナフタセニル基、2-ペンタセニル基等の炭素数10~30の縮合環炭化水素基、o-ビフェニリル基、m-ビフェニリル基、p-ビフェニリル基、テルフェニリル基、7-(2-ナフチル)-2-ナフチル基等の炭素数12~30の環集合炭化水素基が挙げられる。
脂肪族複素環基としては、3-イソクロマニル基、7-クロマニル基、3-クマリニル基、ピペリジノ基、モルホリノ基、2-モルホリニル基等の炭素数3~18の1価の脂肪族複素環基が挙げられる。
芳香族複素環基としては、2-フリル基、3-フリル基、2-チエニル基、3-チエニル基、2-ベンゾフリル基、2-ベンゾチエニル基、2-ピリジル基、3-ピリジル基、4-ピリジル基、2-キノリル、5-イソキノリル基等の炭素数3~30の芳香族複素環基が挙げられる。
正孔注入層の構成材料としては、下記一般式(4)で表される構造を有する化合物を好適に用いることができる。
アリール基としては、フェニル基などの単環芳香族炭化水素環基、ナフチル基、アントラセニル基などの多環芳香族炭化水素環基などが挙げられる。
アラルキル基としては、ベンジル基、フェニルプロピル基、ナフチルメチル基などが挙げられる。
複素環基としては、ピロリル基、チエニル基、ピリジル基、フェナジル基、ピリダジル基、アクリジル基などの複素単環や複素縮合環などが挙げられる。
本発明においては、下記一般式(5)~(12)で表される構造を有する化合物も好適に用いられる。
核原子数1~50のアルキル基としては、メチル基、エチル基、ブチル基、ペンチル基、ヘキシル基、トリフルオロメチル基、トリフルオロエチル基などが挙げられる。
上述の正孔注入層に用いられる材料は単独で用いてもよく、また複数種を併用して用いてもよいが、本発明に係る正孔注入層は、単種の化合物からなることが好ましい。
正孔輸送層は、正孔を輸送する機能を有する材料からなる。正孔輸送層は、陽極より注入された正孔を発光層に伝達する機能を有する層である。
有機EL素子において、正孔輸送層の層厚に特に制限はないが、通常は5nm~5μmの範囲内であり、より好ましくは2~500nmの範囲内であり、更に好ましくは5~200nmの範囲内である。
正孔輸送層は、単層、2層、あるいは3層であってもよい。
また、特表2003-519432号公報や特開2006-135145号公報等に記載されているヘキサアザトリフェニレン誘導体も正孔輸送材料として用いることができる。
また、特開平11-251067号公報、J.Huang et.al.著文献(Applied Physics Letters 80(2002),p.139)に記載されているような、いわゆるp型正孔輸送材料やp型-Si、p型-SiC等の無機化合物を用いることもできる。さらに、Ir(ppy)3に代表されるような中心金属にIrやPtを有するオルトメタル化有機金属錯体も好ましく用いられる。
電子阻止層は、広い意味では正孔輸送層の機能を有する層である。好ましくは、正孔を輸送する機能を有しつつ、電子を輸送する能力が小さい材料からなる。電子阻止層は、正孔を輸送しつつ電子を阻止することで、電子と正孔の再結合確率を向上させることができる。
また、上述の正孔輸送層の構成を必要に応じて、有機EL素子の電子阻止層として用いることができる。有機EL素子に設ける電子阻止層は、発光層の陽極側に隣接して設けられることが好ましい。
電子阻止層に用いられる材料としては、上述の正孔輸送層に用いられる材料が好ましく用いることができる。また、上述のホスト化合物として用いられる材料も、電子阻止層として好ましく用いることができる。
正孔阻止層は、広い意味では電子輸送層の機能を有する層である。好ましくは、電子を輸送する機能を有しつつ、正孔を輸送する能力が小さい材料からなる。電子を輸送しつつ正孔を阻止することで、電子と正孔の再結合確率を向上させることができる。
また、正孔阻止層に、三重項エネルギーを阻止する層としての機能も有すると更に有効である。
また、後述の電子輸送層の構成を、必要に応じて正孔阻止層として用いることができる。
有機EL素子に設ける正孔阻止層は、発光層の陰極側に隣接して設けられることが好ましい。
有機EL素子において、正孔阻止層の層厚は、好ましくは3~100nmの範囲内であり、更に好ましくは5~30nmの範囲内である。
正孔阻止層に用いられる材料としては、後述の電子輸送層に用いられる材料が好ましく用いられ、また、上述のホスト化合物として用いられる材料も正孔阻止層に好ましく用いられる。
有機EL素子に用いる電子輸送層とは、電子を輸送する機能を有する材料からなり、陰極より注入された電子を発光層に伝達する機能を有する。
電子輸送材料は単独で用いてもよく、また複数種を併用して用いてもよい。
電子輸送層の層厚については特に制限はないが、通常は2nm~5μmの範囲内であり、より好ましくは2~500nmの範囲内であり、更に好ましくは5~200nmの範囲内である。
したがって、本発明の有機EL素子では、各発光ユニットの総厚の調整を、正孔輸送性を有する層(例えば、正孔注入層、正孔輸送層、電子阻止層等)及び電子輸送性を有する層(例えば、電子注入層、電子輸送層、正孔阻止層)の総層厚を数nm~数μmの間で適宜調整することで行うことが好ましい。
一方で、電子輸送性を有する層の総層厚を厚くすると電圧が上昇しやすくなるため、特に総層厚が厚い場合においては、電子輸送層の電子移動度は1×10-5cm2/Vs以上であることが好ましい。
芳香族炭化水素環誘導体としては、ナフタレン誘導体、アントラセン誘導体、トリフェニレン等が挙げられる。
また、これらの材料を高分子鎖に導入した、又は、これらの材料を高分子の主鎖とした高分子材料を用いることもできる。
より好ましい電子輸送材料としては、ピリジン誘導体、ピリミジン誘導体、ピラジン誘導体、トリアジン誘導体、ジベンゾフラン誘導体、ジベンゾチオフェン誘導体、カルバゾール誘導体、アザカルバゾール誘導体、ベンズイミダゾール誘導体が挙げられる。
電子注入層(「陰極バッファー層」ともいう。)は、駆動電圧低減や発光輝度向上のために陰極と発光層との間に設けられる層である。電子注入層の一例は、「有機EL素子とその工業化最前線(1998年11月30日エヌ・ティー・エス社発光)」の第2編第2章「電極材料」(123~166頁)に記載されている。
電子注入層はごく薄い膜であることが好ましく、素材にもよるが、その層厚は0.1~5nmの範囲内が好ましい。また、構成材料が断続的に存在する不均一な膜であってもよい。
また、上記の電子注入層に用いられる材料は単独で用いてもよく、複数種を併用して用いてもよい。
本発明の有機EL素子においては、各発光ユニットの間に、非発光性の電荷発生ユニットが設けられる。電荷発生ユニットは、電界中において、複数の発光ユニットを直列に電気的に連結する有機化合物層との界面を持つ層である。
また、電荷発生ユニットは、外部電界により、層内部で正孔、電子を発生・輸送することができるバイポーラ層としてもよい。また、通常の電極材料として使用可能な金属、金属酸化物、及びその合金などが好適に使用できる。
このように、電荷発生ユニットとしては、一方の発光ユニットに電子を注入する機能を有し、他方の発光ユニットに正孔を注入する機能を有する、電荷発生層の構成とすることができる。
無機化合物としては、金属、無機酸化物、無機塩等が挙げられる。
また、この他にもビス[2-(2-ヒドロキシフェニル)ベンズオキサゾラト]亜鉛(Zn(BOX)2)、ビス[2-(2-ヒドロキシフェニル)ベンゾチアゾラト]亜鉛(Zn(BTZ)2)等のオキサゾール系、チアゾール系配位子を有する金属錯体等も用いることができる。
有機EL素子を構成する発光ユニットは、更に他の添加剤を含んでもよい。
添加剤としては、例えば、臭素、ヨウ素、塩素等のハロゲン元素やハロゲン化化合物、Pd、Ca、Na等のアルカリ金属やアルカリ土類金属、遷移金属の化合物や錯体、塩等が挙げられる。
添加剤の含有量は、任意に決定することができるが、含有される層の全質量%に対して1000ppm以下であることが好ましく、より好ましくは500ppm以下であり、更に好ましくは50ppm以下である。
ただし、電子や正孔の輸送性を向上させる目的や、励起子のエネルギー移動を有利にするための目的などによってはこの範囲内ではない。
有機EL素子における半透過性電極としては、仕事関数の大きい(4eV以上、好ましくは4.3eV以上)金属、合金、電気伝導性化合物、及びこれらの混合物からなる電極物質が用いられる。
具体的には、銀(Ag)、アルミニウム(Al)や、インジウム錫酸化物(ITO)、酸化ケイ素を含むインジウム錫酸化物(以下、ITSOとも記す。)、2~20%の酸化亜鉛を含む酸化インジウム等の透光性材料の他、金(Au)、白金(Pt)、ニッケル(Ni)、タングステン(W)、クロム(Cr)、モリブデン(Mo)、鉄(Fe)、コバルト(Co)、銅(Cu)、パラジウム(Pd)等の金属材料、又はこれらの積層構造を用いることができる。
有機導電性化合物のように塗布可能な物質を用いる場合には、印刷方式、コーティング方式など湿式製膜法を用いることもできる。
反射性電極としては、仕事関数の小さい(4eV以下)金属(電子注入性金属と称する。)、合金、電気伝導性化合物、及びこれらの混合物からなる電極物質が用いられる。このような電極物質の具体例としては、ナトリウム、ナトリウム-カリウム合金、マグネシウム、リチウム、マグネシウム/銅混合物、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、インジウム、リチウム/アルミニウム混合物、アルミニウム、銀、銀を主成分とする合金、アルミニウム/銀混合物、希土類金属等が挙げられる。
有機EL素子に用いる基板は、ガラス、プラスチック等の種類には特に限定はなく、また、透明であっても不透明であってもよい。基板側から光を取り出す場合には、基板は透明であることが好ましい。
透明な基板として、好ましくは、ガラス、石英、透明樹脂フィルムを挙げることができる。特に好ましくは、有機EL素子にフレキシブル性を与えることが可能な樹脂フィルムである。
有機EL素子の封止に用いられる封止手段としては、例えば、封止部材と、電極、基板とを接着剤で接着する方法を挙げることができる。
封止部材としては、有機EL素子の表示領域を覆うように配置されていればよく、凹板状でも、平板状でもよい。また、透明性、電気絶縁性は特に限定されない。
ガラス板としては、特にソーダ石灰ガラス、バリウム・ストロンチウム含有ガラス、鉛ガラス、アルミノケイ酸ガラス、ホウケイ酸ガラス、バリウムホウケイ酸ガラス、石英等を挙げることができる。
また、ポリマー板及びポリマーフィルムとしては、ポリカーボネート、アクリル、ポリエチレンテレフタレート、ポリエーテルサルファイド、ポリサルフォン等を挙げることができる。
金属板としては、ステンレス、鉄、銅、アルミニウム、マグネシウム、ニッケル、亜鉛、クロム、チタン、モリブテン、シリコン、ゲルマニウム及びタンタルからなる群から選ばれる1種以上を含む金属、及び、合金が挙げられる。
有機EL素子の機械的強度を高めるために、上記封止用フィルムの外側に保護膜あるいは保護板を設けてもよい。特に、封止が上記封止膜により行われている場合には、その機械的強度は必ずしも高くないため、このような保護膜、保護板を設けることが好ましい。これに使用することができる材料としては、上記封止に用いたのと同様のガラス板、ポリマー板・フィルム、金属板・フィルム等を用いることができるが、軽量かつ薄膜化ということからポリマーフィルムを用いることが好ましい。
有機EL素子は、空気よりも屈折率の高い(屈折率1.6~2.1程度の範囲内)層の内部で発光し、発光層で発生した光のうち15~20%程度の光しか取り出せないことが一般的に言われている。これは、臨界角以上の角度θで界面(透明基板と空気との界面)に入射する光は、全反射を起こし素子外部に取り出すことができないことや、透明電極又は発光層と透明基板との間で光が全反射を起こし、光が透明電極又は発光層を導波し、結果として、光が素子側面方向に逃げるためである。
次に、半透過性電極/第1発光ユニット/電荷発生ユニット/第2発光ユニット/反射性電極からなる有機EL素子の作製方法の一例について説明する。
この有機化合物薄膜の薄膜化の方法としては、蒸着法、ウェットプロセス(スピンコート法、キャスト法、インクジェット法、印刷法、LB法(ラングミュア-ブロジェット法)、スプレー法、印刷法、スロット型コータ法)等があるが、均質な膜が得られやすく、かつピンホールが生成しにくい等の点から、真空蒸着法、スピンコート法、インクジェット法、印刷法、スロット型コータ法が特に好ましい。層毎に異なる成膜法を適用してもよい。
成膜に蒸着法を採用する場合、その蒸着条件は使用する化合物の種類等により異なるが、一般にボート加熱温度50~450℃、真空度1×10-6~1×10-2Pa、蒸着速度0.01~50nm/秒、基板温度-50℃~300℃、層厚0.1nm~5μm、好ましくは5~200nmの範囲内で適宜選ぶことが望ましい。
電荷発生ユニットの形成方法としては、薄膜形成ができる方法であれば特に限定されず、例えば、蒸着法、スパッタリング、ウェットプロセス(スピンコート法、キャスト法、インクジェット法、LB法、スプレー法、印刷法、スロット型コータ法)等が挙げられる。
これにより所望の有機EL素子が得られる。
例えば、半透過性電極及び反射性電極の一部又は全部を露出させた状態で有機EL素子を熱硬化性樹脂で被覆してこれを加熱硬化させ、有機EL素子を封止する。
その後、有機EL素子の封止体とそこから露出した有機EL素子の半透過性電極及び反射性電極の一部又は全部とを、保護部材で被覆し、保護部材の重複部分を所定温度で加熱圧着する。2枚の保護部材を重ね合わせて有機EL素子の封止体等を被覆しその側縁部同士を加熱圧着してもよいし、1枚の保護部材を折り畳んで有機EL素子の封止体等を被覆しその側縁部(特に、開放端)同士を加熱圧着してもよい。
以上の処理により、有機EL素子を封止・保護した有機ELモジュールが製造される。
なお、上述の実施態様では、基板側から、半透過性電極、第1発光ユニット、電荷発生ユニット、第2発光ユニット、及び、反射性電極がこの順に積層された、ボトムエミッション型の有機EL素子を例示したが、この構成に限定されない。例えば、各層の積層順は逆でもよいし、半透過性電極と反射性電極とが逆の構成であってもよく、少なくとも二つの発光層を有していればよい。
適宜、これらを組み合わせた構成とすることも可能である。
次に、上述の有機EL素子が用いられる電子デバイスの実施形態の一例として、照明装置について説明する。
以上に説明した有機EL素子を用いれば、実質的に発光色が同色系である照明装置を作製することが可能である。
また、照明装置は、例えば有機EL素子を複数用いることにより、発光面を大面積化することもできる。この場合、基板上に有機EL素子を設けた複数の発光パネルを、支持基板上に複数配列する(すなわち、タイリングする。)ことによって発光面を大面積化する。支持基板は、封止材を兼ねるものであってもよく、この支持基板と、発光パネルの基板との間に有機EL素子を挟持する状態で各発光パネルをタイリングする。支持基板と基板との間には接着剤を充填し、これによって有機EL素子を封止してもよい。なお、発光パネルの周囲には、半透過性電極及び反射性電極の端子を露出させておく。
有機EL素子について、発光領域面積が5cm×5cmとなるように各サンプルを作製した。
(1.1)半透過性電極の形成
透明支持基板として、厚さ0.7mmのガラス基板を準備した。透明支持基板をイソプロピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、UVオゾン洗浄を5分間行った。そして、この透明支持基板上に、Ag(銀)を20nmの厚さでマスク蒸着して、半透過性電極である陽極を形成した。
次に、陽極を形成した透明支持基板を市販の真空蒸着装置の基板ホルダーに固定した。そして、各層の材料を、真空蒸着装置内の各蒸着用るつぼに素子作製に最適な量を充填した。各蒸着用るつぼとして、モリブデン製又はタングステン製の抵抗加熱用材料で作製された蒸着用るつぼを用いた。
次に、真空度1×10-4Paまで減圧した後、例示化合物HI-145(HAT-CN)の入った蒸着用るつぼに通電して加熱し、蒸着速度0.1nm/秒で陽極上に蒸着し、層厚5nmになるように第1正孔注入層を形成した。
次に、下記構造式の化合物1-A(ガラス転移点(Tg)=140℃)を層厚65nmになるように蒸着し、第1正孔輸送層を形成した。
次に、下記構造式の化合物1-Bを、層厚20nmになるように蒸着し、第1電子阻止層を形成した。
次に、ホスト化合物として下記構造式の化合物2-A(Tg=143℃)が77vol%、アシストドーパントとして下記構造式の化合物2-B(Ir(bzq)3)が15vol%、橙色リン光発光ドーパントとして下記構造式のpq(橙1)が8vol%となるように蒸着し、橙色を呈する層厚30nmの第1リン光発光層を形成した。
次に、下記構造式の化合物3が86vol%、LiFが14vol%となるように蒸着し、層厚10nmの層を形成した。さらに、化合物3が98vol%、Liが2vol%となるように蒸着し、層厚10nmの層を形成した。これにより、化合物3及びLiFからなる層と、化合物3及びLiからなる層との2層から構成される第2電子輸送層(電子注入層を兼ねる。)を形成した。
次いで、第1発光ユニット上に、Agを厚さ1nmで成膜し、電荷発生ユニットを形成した。
(1.4.1)正孔輸送性を有する層
次いで、第1発光ユニットの正孔輸送性を有する層と同様にして、例示化合物HI-145(HAT-CN)の入った蒸着用るつぼに通電して加熱し、蒸着速度0.1nm/秒で電荷発生ユニット上に蒸着し、層厚15nmの第2正孔注入層を形成した。
次に、化合物1-Aを層厚100nmになるように蒸着し、第2正孔輸送層を形成した。
次に、化合物1-Bを層厚10nmになるように蒸着し、第2電子阻止層を形成した。
次いで、ホスト化合物として化合物2-A(Tg=143℃)が77vol%、アシストドーパントとして化合物2-Bが15vol%、橙色リン光発光ドーパントとしてpq(橙1)が8vol%となるように蒸着し、橙色を呈する層厚20nmの第2リン光発光層を形成した。
次に、第1発光ユニットの電子輸送層と同様にして、化合物3が86vol%、LiFが14vol%となるように蒸着し、層厚10nmの層を形成した。さらに、化合物3が98vol%、Liが2vol%となるように蒸着し、層厚10nmの層を形成した。これにより、化合物3及びLiFからなる層と、化合物3及びLiからなる層との2層から構成される第2電子輸送層を形成した。
次に、アルミニウム150nmを蒸着して陰極を形成した。
次に、陰極まで形成した有機EL素子の非発光面をガラスケースで覆い、有機EL素子が作製されたガラス基板と接触する、有機EL素子を覆うガラスケースの周辺部に、エポキシ系光硬化型接着剤(東亞合成社製ラクストラックLC0629B)によるシール材を設けた。そして、このシール材を上記有機EL素子の陰極側に重ねてガラス基板と密着させた。その後、ガラスケース側からUV光を照射してシール材を硬化することで有機EL素子を封止し、有機EL素子101を作製した。
なお、ガラスケースでの封止作業は、有機EL素子を大気に接触させることなく窒素雰囲気下のグローブボックス(純度99.999%以上の高純度窒素ガスの雰囲気下)で行った。
有機EL素子101の作製において、第2正孔輸送層の層厚を110nmに変更した以外は同様にして、有機EL素子102を作製した。
有機EL素子101の作製において、第1正孔輸送層の層厚を55nm、第2正孔輸送層の層厚を75nmとし、第1及び第2発光層を以下のようにして形成した以外は同様にして、有機EL素子201を作製した。
ホスト化合物として、化合物2-A(Tg=143℃)が85vol%、黄色リン光発光ドーパントとして化合物2-Bが15vol%となるように蒸着し、黄色を呈する層厚30nmの第1リン光発光層を形成した。
ホスト化合物として、化合物2-A(Tg=143℃)が85vol%、黄色リン光発光ドーパントとして化合物2-Bが15vol%となるように蒸着し、黄色を呈する層厚20nmの第2リン光発光層を形成した。
有機EL素子201の作製において、第2正孔輸送層の層厚を85nmに変更した以外は同様にして、有機EL素子202を作製した。
有機EL素子101の作製において、第1正孔輸送層の層厚を41nm、第2正孔輸送層の層厚を53nmとし、第1及び第2発光層を以下のようにして形成した以外は同様にして、有機EL素子301を作製した。
ホスト化合物として、下記構造式の化合物4-A(Tg=189℃)が98vol%、青色蛍光発光ドーパントとして下記構造式の化合物4-Bが2vol%となるように蒸着し、青色を呈する層厚30nmの第1蛍光発光層を形成した。
ホスト化合物として、化合物4-A(Tg=189℃)が85vol%、青色蛍光発光ドーパントとして化合物4-Bが15vol%となるように蒸着し、青色を呈する層厚20nmの第2蛍光発光層を形成した。
有機EL素子301の作製において、第2正孔輸送層の層厚を63nmに変更した以外は同様にして、有機EL素子302を作製した。
作製した各有機EL素子について、下記のようにして、素子特性の評価を行った。
評価結果を表1に示す。
陽極(半透過性電極)から第1及び第2発光層まで間に挟持される全ての層を1層とみなし、各発光層の発光ドーパントの最大発光極大波長における屈折率n1及びn2と、陽極(半透過性電極)から第1及び第2発光層までの実距離d1及びd2を、分光エリプソメータとして、堀場JYOBIN-YVON製UVSEL/FUV-FGMSを使用し、解析は、波長500~800nmの範囲内にて、Cauchy(n(屈折率):可変、k(減衰係数):なしで固定)で実施して、屈折率及び層厚を測定した。
具体的には、測定対象となる第1及び第2発光層までをシリコンウエハ上に成膜して、測定・解析を行った。
作製した各有機EL素子について、分光放射輝度計CS-1000(コニカミノルタ社製)を用いて、電圧ごとに、各有機EL素子の正面輝度を測定し、正面輝度1000cd/m2における電流効率を測定した。
なお、有機EL素子102、202及び302の電力効率は、それぞれ有機EL素子101、201及び301の電力効率を100とする相対値で表している。
作製した各有機EL素子について、常温(25℃)下で、初期輝度を4000cd/m2とし、残存率(輝度)が70%となる際の寿命を測定した。
なお、有機EL素子102、202及び302の常温寿命は、それぞれ有機EL素子101、201及び301の常温寿命を100とする相対値で表している。
作製した各有機EL素子について、有機EL素子自体を恒温層に入れ、恒温層を85℃に設定し、初期正面輝度1000cd/m2にて連続駆動させ、残存率(輝度)が70%となる際の寿命を測定した。
なお、有機EL素子102、202及び302の駆動寿命は、それぞれ有機EL素子101、201及び301の駆動寿命を100とする相対値で表している。
表1~3から明らかなように、本発明の有機EL素子は、比較例の有機EL素子と比較して、電力効率、常温寿命及び85℃での駆動寿命が優れている。
以上から、N番目の発光ユニットの発光層における発光ドーパントのELスペクトルの最大発光極大波長λN(max)と、(N+1)番目の発光ユニットの発光層における発光ドーパントのELスペクトルの最大発光極大波長λN+1(max)との差(λN+1(max)-λN(max))を、1~50nmの範囲内とすることが有用であることがわかる。
2 半透過性電極
4 第1発光ユニット
4a 正孔輸送性を有する層
4b 発光層
4c 電子輸送性を有する層
6 電荷発生ユニット
8 第2発光ユニット
8a 正孔輸送性を有する層
8b 発光層
8c 電子輸送性を有する層
10 反射性電極
AN 吸収スペクトル
EN、EN+1 ELスペクトル
S 重複領域
Claims (5)
- 一対の半透過性電極と反射性電極間に、複数の発光ユニットを有し、各前記発光ユニット間には、電荷発生ユニットが形成されている有機エレクトロルミネッセンス素子であって、
前記半透過性電極側からN番目の発光ユニットの発光層と(N+1)番目の発光ユニットの発光層とには、発光色が同色系である発光ドーパントが含有され、
前記N番目の発光ユニットの発光層における発光ドーパントのエレクトロルミネッセンススペクトルの最大発光極大波長λN(max)と、前記(N+1)番目の発光ユニットの発光層における発光ドーパントのエレクトロルミネッセンススペクトルの最大発光極大波長λN+1(max)とが、下記条件式(1)を満たすことを特徴とする有機エレクトロルミネッセンス素子。
1nm≦λN+1(max)-λN(max)≦50nm (1) - 前記半透過性電極から前記N番目の発光ユニットの発光層までの光学距離と、前記半透過性電極から前記(N+1)番目の発光ユニットの発光層までの光学距離とが、下記条件式(2)を満たすことを特徴とする請求項1に記載の有機エレクトロルミネッセンス素子。
1nm≦nN+1dN+1×4/(2mN+1+1)-nNdN×4/(2mN+1)≦50nm(ただし、mN<mN+1) (2)
(nN:前記半透過性電極と前記N番目の発光ユニットの発光層との間に挟持される全ての層の屈折率
nN+1:前記半透過性電極と前記(N+1)番目の発光ユニットの発光層との間に挟持される全ての層の屈折率
dN(nm):前記半透過性電極から前記N番目の発光ユニットの発光層までの実距離
dN+1(nm):前記半透過性電極から前記(N+1)番目の発光ユニットの発光層までの実距離
mN:0以上の整数
mN+1:1以上の整数) - 前記N番目の発光ユニットの発光層における発光ドーパントのエレクトロルミネッセンススペクトルの最大発光極大波長λN(max)と、前記(N+1)番目の発光ユニットの発光層における発光ドーパントのエレクトロルミネッセンススペクトルの最大発光極大波長λN+1(max)とが、下記条件式(3)を満たすことを特徴とする請求項1又は請求項2に記載の有機エレクトロルミネッセンス素子。
5nm≦λN+1(max)-λN(max)≦50nm (3) - 前記N番目の発光ユニットの発光層における発光ドーパントのエレクトロルミネッセンススペクトルの最大発光極大波長λN(max)と、前記(N+1)番目の発光ユニットの発光層における発光ドーパントのエレクトロルミネッセンススペクトルの最大発光極大波長λN+1(max)とが、下記条件式(4)を満たすことを特徴とする請求項1から請求項3までのいずれか一項に記載の有機エレクトロルミネッセンス素子。
20nm≦λN+1(max)-λN(max)≦50nm (4) - 前記複数の発光ユニットのすべての発光層には、発光色が同色系である発光ドーパントが含有されていることを特徴とする請求項1から請求項4までのいずれか一項に記載の有機エレクトロルミネッセンス素子。
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