WO2010016454A1 - 有機電界発光素子および表示装置 - Google Patents
有機電界発光素子および表示装置 Download PDFInfo
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- WO2010016454A1 WO2010016454A1 PCT/JP2009/063729 JP2009063729W WO2010016454A1 WO 2010016454 A1 WO2010016454 A1 WO 2010016454A1 JP 2009063729 W JP2009063729 W JP 2009063729W WO 2010016454 A1 WO2010016454 A1 WO 2010016454A1
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- 0 CC(*1[B+]F)=NC=C1C(C=C1)=NC1=C[C@@]1NC(c2cnc(C)[o]2)=CC1 Chemical compound CC(*1[B+]F)=NC=C1C(C=C1)=NC1=C[C@@]1NC(c2cnc(C)[o]2)=CC1 0.000 description 1
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- CVXWKNBRDWUKJM-UHFFFAOYSA-N COc(cccc1)c1-c1c(C=C(C=C2)N=C2C2=CC=CS2[F][B+]F)[nH]c(-c2ccccc2OC)c1 Chemical compound COc(cccc1)c1-c1c(C=C(C=C2)N=C2C2=CC=CS2[F][B+]F)[nH]c(-c2ccccc2OC)c1 CVXWKNBRDWUKJM-UHFFFAOYSA-N 0.000 description 1
- DNVYIXXYAINVSH-LRKGMWOTSA-N Cc(cc1)ccc1-c1c(/C(/c2cccc3c2CCC3)=C(/C(c2ccc(C)cc2)=C2)\N=C2c2ccc(C)cc2)[nH]c(-c2ccc(C)cc2)c1 Chemical compound Cc(cc1)ccc1-c1c(/C(/c2cccc3c2CCC3)=C(/C(c2ccc(C)cc2)=C2)\N=C2c2ccc(C)cc2)[nH]c(-c2ccc(C)cc2)c1 DNVYIXXYAINVSH-LRKGMWOTSA-N 0.000 description 1
- MHMMNWUJVSQSFO-UHFFFAOYSA-N Cc1c[s]c(-c2ccc(C=C(C=C3)N=C3C3=CC(C)=CS3[F][B+]F)[nH]2)c1 Chemical compound Cc1c[s]c(-c2ccc(C=C(C=C3)N=C3C3=CC(C)=CS3[F][B+]F)[nH]2)c1 MHMMNWUJVSQSFO-UHFFFAOYSA-N 0.000 description 1
- ZBSKVNKUZWWEDT-WZGDRKDQSA-N Cc1cc(-c2c(/C(/c3cccc4c3cccc4)=C(/C(c3cc(C)cc(C)c3)=C3)\N=C3c3cc(C)cc(C)c3)[nH]c(-c3cc(C)cc(C)c3)c2)cc(C)c1 Chemical compound Cc1cc(-c2c(/C(/c3cccc4c3cccc4)=C(/C(c3cc(C)cc(C)c3)=C3)\N=C3c3cc(C)cc(C)c3)[nH]c(-c3cc(C)cc(C)c3)c2)cc(C)c1 ZBSKVNKUZWWEDT-WZGDRKDQSA-N 0.000 description 1
- URMADCNUVGBBAS-UHFFFAOYSA-N Cc1ccc(C(C=C2c3ccc(C)c4c3cccc4)[N-](B(F)F)/C2=N\c([nH]c(-c2c(cccc3)c3c(C)cc2)c2)c2-c2c(cccc3)c3c(C)cc2)c2c1cccc2 Chemical compound Cc1ccc(C(C=C2c3ccc(C)c4c3cccc4)[N-](B(F)F)/C2=N\c([nH]c(-c2c(cccc3)c3c(C)cc2)c2)c2-c2c(cccc3)c3c(C)cc2)c2c1cccc2 URMADCNUVGBBAS-UHFFFAOYSA-N 0.000 description 1
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- 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
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
Definitions
- the present invention relates to an organic electroluminescent element and a display device, and more particularly to a red light emitting organic electroluminescent element and a display device using the same.
- organic electroluminescent element As-called organic EL element, a display device using an organic electroluminescent element has been attracting attention as a lightweight and highly efficient flat panel display device.
- An organic electroluminescent element constituting such a display device is provided on a transparent substrate made of glass or the like, for example, an anode made of ITO (Indium Tin Oxide: transparent electrode) in order from the substrate side, an organic layer, and A cathode is laminated.
- the organic layer has a structure in which a hole injecting layer, a hole transporting layer, and an electron transporting light emitting layer are sequentially stacked in this order from the anode side.
- the organic electroluminescence device configured as described above, electrons injected from the cathode and holes injected from the anode are recombined in the light emitting layer, and light generated during the recombination is transmitted through the anode to the substrate side. Is taken out of.
- an organic electroluminescent element in addition to the above-described structure, a structure in which a cathode, an organic layer, and an anode are sequentially laminated in order from the substrate side, and an electrode positioned on the upper side (upper electrode as a cathode or an anode)
- an electrode positioned on the upper side upper electrode as a cathode or an anode
- top-emitting type in which light is extracted from the upper electrode side opposite to the substrate by forming a transparent material.
- TFT thin film transistor
- Top Emission structure in which a top emission organic electroluminescent element is provided on the substrate on which the TFT is formed. This is advantageous in improving the aperture ratio of the light emitting portion.
- a configuration using a naphthacene derivative (including a rubrene derivative) as a dopant material is proposed as a new red light-emitting material that is replaced with a conventionally known pyran derivative typified by DCJTB (for example, see Patent Documents 1 and 2 below).
- Patent Document 2 also proposes a configuration in which white light emission is obtained by laminating a second light-emitting layer containing a penylene derivative and an anthracene derivative on a first light-emitting layer using a rubrene derivative as a dopant material. Yes.
- organic electroluminescent elements of three colors that emit light of three primary colors (red, green, and blue) are used in an array, or organic electroluminescent elements that emit white light and each color are used.
- These color filters or color conversion layers are used in combination.
- a configuration using an organic electroluminescent element that emits light of each color is advantageous.
- the light emission of the red light emitting element using the naphthacene derivative (rubrene derivative) described above has a current efficiency of about 6.7 cd / A, and the light emission color is orange light emission rather than red light emission.
- an object of the present invention is to provide a red light emitting organic electroluminescent element having sufficiently good luminous efficiency and color purity, and a display device using the same.
- An organic electroluminescent element of the present invention for achieving such an object is a red light emitting organic electroluminescent element in which an organic layer having a light emitting layer is sandwiched between an anode and a cathode.
- This light-emitting layer contains a host material made of a polycyclic aromatic hydrocarbon compound having a parent skeleton of 4 to 7 together with a red light-emitting guest material.
- a photosensitizing layer containing a phosphorescent material made of an organic material is laminated adjacent to the light emitting layer.
- the current efficiency is increased as compared with the configuration in which the photosensitizing layer is not provided, and the light containing the light emitting material is included. It was found that only red emitted light generated in the light emitting layer without being influenced by the sensitizing layer is extracted from the device.
- the phosphorescent light emission energy in the photosensitized layer is absorbed by the light emitting layer and contributes to the light emission efficiency in the light emitting layer.
- the phosphorescence emission of the phosphorescent material via the triplet exciton has higher emission efficiency than the fluorescence emission via the singlet exciton. Therefore, in principle, the use of a phosphorescent material having higher luminous efficiency than the fluorescent material as the photosensitizing layer can effectively increase the luminous efficiency from the light emitting layer.
- the present invention is also a display device in which a plurality of organic electroluminescent elements having the above-described configuration are arranged on a substrate.
- a display device using an organic electroluminescent element having high luminance and high color purity as a red light emitting element since a display device using an organic electroluminescent element having high luminance and high color purity as a red light emitting element is configured, it can be combined with other green light emitting elements and blue light emitting elements. This enables full color display with high color reproducibility.
- the organic electroluminescent element of the present invention it is possible to effectively improve the luminous efficiency of red emitted light while maintaining the color purity.
- a pixel is formed by combining a green light emitting element and a blue light emitting element together with an organic electroluminescent element that is a red light emitting element having high color purity and luminous efficiency. This enables full color display with high color reproducibility.
- the organic electroluminescent element of embodiment it is a schematic diagram of the energy level of the luminescent guest material contained in a light emitting layer, and the phosphorescent luminescent material (luminescent guest material) contained in a photosensitizing layer. It is a figure which shows an example of the circuit structure of the display apparatus of embodiment. It is a figure which shows the 1st example of the cross-sectional structure of the principal part in the display apparatus of embodiment. It is a figure which shows the 2nd example of the cross-sectional structure of the principal part in the display apparatus of embodiment. It is a figure which shows the 3rd example of the cross-sectional structure of the principal part in the display apparatus of embodiment.
- FIG. 1 is a perspective view showing a notebook personal computer to which the present invention is applied. It is a perspective view which shows the video camera to which this invention is applied.
- FIG. 1 shows the portable terminal device to which this invention is applied, for example, a mobile telephone
- A is the front view in the open state
- B is the side view
- C is the front view in the closed state
- D is a left side view
- E is a right side view
- F is a top view
- G is a bottom view.
- FIG. 1 is a cross-sectional view schematically showing an organic electroluminescent element of the present invention.
- the organic electroluminescent element 11 shown in this figure is formed by laminating an anode 13, an organic layer 14, and a cathode 15 in this order on a substrate 12.
- the organic layer 14 is formed by laminating, for example, a hole injection layer 14a, a hole transport layer 14b, a light emitting layer 14c, a photosensitizing layer 14d, and an electron transport layer 14e in this order from the anode 13 side.
- the present invention is characterized by the configuration of the light emitting layer 14c and the configuration in which the photosensitizing layer 14d is provided in contact therewith.
- the organic electroluminescent element 11 having such a stacked configuration is configured as a top-emitting element that extracts light from the side opposite to the substrate 12, and details of each layer in this case are described from the substrate 12 side. These will be described in order.
- the substrate 12 is a support on which the organic electroluminescent elements 11 are arranged and formed on one main surface side, and may be a known substrate, for example, a film or sheet made of quartz, glass, metal foil, or resin. Of these, quartz and glass are preferable.
- methacrylic resin represented by polymethyl methacrylate (PMMA), polyethylene terephthalate (PET), polyethylene naphthalate (PEN), poly Examples thereof include polyesters such as butylene naphthalate (PBN), polycarbonate resins, and the like, but it is necessary to perform a laminated structure and surface treatment that suppress water permeability and gas permeability.
- the anode 13 has a large work function from the vacuum level of the electrode material in order to inject holes efficiently, for example, aluminum (Al), chromium (Cr), molybdenum (Mo), tungsten (W), copper (Cu), silver (Ag), gold (Au) metals and alloys thereof, oxides of these metals and alloys, or alloys of tin oxide (SnO 2 ) and antimony (Sb), ITO (indium) Tin oxide), InZnO (indium zinc oxide), alloys of zinc oxide (ZnO) and aluminum (Al), and oxides of these metals and alloys are used alone or in a mixed state.
- the anode 13 may have a laminated structure of a first layer having excellent light reflectivity and a second layer having a light transmittance and a large work function provided on the first layer.
- the first layer is made of an alloy mainly composed of aluminum.
- the subcomponent may include at least one element having a work function relatively smaller than that of aluminum as a main component.
- a lanthanoid series element is preferable.
- the work function of the lanthanoid series elements is not large, the inclusion of these elements improves the stability of the anode and also satisfies the hole injection property of the anode.
- elements such as silicon (Si) and copper (Cu) may be included as subcomponents.
- the content of subcomponents in the aluminum alloy layer constituting the first layer is preferably about 10 wt% or less in total for Nd, Ni, Ti, or the like that stabilizes aluminum.
- the second layer can be exemplified by a layer made of at least one of an aluminum alloy oxide, a molybdenum oxide, a zirconium oxide, a chromium oxide, and a tantalum oxide.
- the oxide of the lanthanoid element has a high transmittance, so that this is included.
- the transmittance of the second layer is improved. For this reason, it is possible to maintain a high reflectance on the surface of the first layer.
- the second layer may be a transparent conductive layer such as ITO (Indium Tin Oxide) or IZO (Indium Zinc Oxide). These conductive layers can improve the electron injection characteristics of the anode 13.
- the anode 13 may be provided with a conductive layer on the side in contact with the substrate 11 for improving the adhesion between the anode 13 and the substrate 12.
- a conductive layer include transparent conductive layers such as ITO and IZO.
- the driving method of the display device configured using the organic electroluminescent element 11 is an active matrix method
- the anode 13 is patterned for each pixel and connected to a driving thin film transistor provided on the substrate 12. It is provided in the state that was done. Further, in this case, although not shown here, an insulating film is provided on the anode 13, and the surface of the anode 13 of each pixel is exposed from the opening of the insulating film.
- the hole injection layer 14a is for increasing the efficiency of hole injection into the light emitting layer 14c.
- Examples of the material for the hole injection layer 14a include benzine, styrylamine, triphenylamine, porphyrin, triphenylene, azatriphenylene, tetracyanoquinodimethane, triazole, imidazole, oxadiazole, polyarylalkane, and phenylene.
- Diamine, arylamine, oxazole, anthracene, fluorenone, hydrazone, stilbene or their derivatives, or heterocyclic conjugated monomers, oligomers or polymers such as polysilane compounds, vinylcarbazole compounds, thiophene compounds or aniline compounds Can be used.
- hole injection layer 14a specific materials for the hole injection layer 14a include ⁇ -naphthylphenylphenylenediamine, porphyrin, metal tetraphenylporphyrin, metal naphthalocyanine, hexacyanoazatriphenylene, 7,7,8,8-tetracyanoquino.
- TCNQ 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane
- F4-TCNQ tetracyano 4,4,4-tris (3-methylphenylphenylamino ) Triphenylamine, N, N, N ′, N′-tetrakis (p-tolyl) p-phenylenediamine, N, N, N ′, N′-tetraphenyl-4,4′-diaminobiphenyl, N-phenyl Carbazole, 4-di-p-tolylaminostilbene, poly (paraphenylenevinylene), poly (thiophene) Vinylene), poly (2,2'-thienylpyrrole), and including without being limited thereto.
- the hole transport layer 14b is for increasing the efficiency of hole injection into the light emitting layer 14c, like the hole injection layer 14a.
- Such a hole transport layer 14b is configured using a material selected from the same materials as the hole injection layer 14a described above.
- the light emitting layer 14 c is a region where holes injected from the anode 13 side and electrons injected from the cathode 15 side are recombined when a voltage is applied to the anode 13 and the cathode 15.
- the structure of the light emitting layer 14c is one feature. That is, the light emitting layer 14c uses a polycyclic aromatic hydrocarbon compound having 4 to 7 ring members as a host material as a host material, and the host material is doped with a red light emitting guest material. Red light emission is generated.
- the host material constituting the light emitting layer 14c is a polycyclic aromatic hydrocarbon compound having a parent skeleton of 4 to 7 members, and pyrene, benzopyrene, chrysene, naphthacene, benzonaphthacene, dibenzonaphthacene, perylene. , Selected from coronen.
- the host material constituting the light emitting layer 14c is a polycyclic aromatic hydrocarbon compound having a mother skeleton of 4 to 7 ring members, and pyrene, benzopyrene, chrysene, naphthacene, benzonaphthacene, dibenzonaphthacene, perylene, coronene. It shall be selected from.
- a naphthacene derivative represented by the following general formula (1) is preferable to use as a host material.
- R 1 to R 8 are each independently hydrogen, halogen, hydroxyl group, substituted or unsubstituted carbonyl group having 20 or less carbon atoms, substituted or unsubstituted carbon group having 20 or less carbon atoms.
- Carbonyl ester group substituted or unsubstituted alkyl group having 20 or less carbon atoms, substituted or unsubstituted alkenyl group having 20 or less carbon atoms, substituted or unsubstituted alkoxyl group having 20 or less carbon atoms, cyano group, nitro group, carbon A substituted or unsubstituted silyl group having 30 or fewer carbon atoms, a substituted or unsubstituted aryl group having 30 or fewer carbon atoms, a substituted or unsubstituted heterocyclic group having 30 or fewer carbon atoms, or a substituted or unsubstituted carbon group having 30 or fewer carbon atoms An amino group is shown.
- the aryl group represented by R 1 to R 8 in the general formula (1) is, for example, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a fluorenyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 1-chrycenyl group, 6-chrycenyl group, 2-fluoranthenyl group, 3-fluoranthenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, o-tolyl Group,
- the heterocyclic group represented by R 1 to R 8 is a 5- or 6-membered aromatic heterocyclic group containing O, N, or S as a hetero atom, or a condensed polycyclic aromatic heterocyclic group having 2 to 20 carbon atoms.
- a cyclic group is mentioned.
- the aromatic heterocyclic group and the condensed polycyclic aromatic heterocyclic group include thienyl group, furyl group, pyrrolyl group, pyridyl group, quinolyl group, quinoxalyl group, imidazopyridyl group, and benzothiazole group.
- Representative examples include 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1-isobenzofuranyl group
- the amino group represented by R 1 to R 8 may be any of an alkylamino group, an arylamino group, an aralkylamino group, and the like. These preferably have an aliphatic group having 1 to 6 carbon atoms and / or an aromatic carbocyclic ring having 1 to 4 rings. Examples of such a group include a dimethylamino group, a diethylamino group, a dibutylamino group, a diphenylamino group, a ditolylamino group, a bisbiphenylylamino group, and a dinaphthylamino group.
- two or more kinds of the above substituents may form a condensed ring, and may further have a substituent.
- the naphthacene derivative represented by the general formula (1) is preferably a rubrene derivative represented by the following general formula (1a).
- R 11 to R 15 , R 21 to R 25 , R 31 to R 35 , and R 41 to R 45 are each independently a hydrogen atom, aryl group, heterocyclic group, amino group, aryloxy A group, an alkyl group, or an alkenyl group; However, R 11 to R 15 , R 21 to R 25 , R 31 to R 35 , and R 41 to R 45 are preferably the same.
- R 5 to R 8 are each independently a hydrogen atom, an aryl group which may have a substituent, or an alkyl group or alkenyl group which may have a substituent.
- Preferred embodiments of the aryl group, heterocyclic group, and amino group in the general formula (1a) may be the same as R 1 to R 8 in the general formula (1).
- R 11 to R 15 , R 21 to R 25 , R 31 to R 35 , and R 41 to R 45 are amino groups, they are alkylamino groups, arylamino groups, or aralkylamino groups. These preferably have an aliphatic having 1 to 6 carbon atoms in total or an aromatic carbocyclic ring having 1 to 4 rings.
- Examples of such a group include a dimethylamino group, a diethylamino group, a dibutylamino group, a diphenylamino group, a ditolylamino group, and a bisbiphenylylamino group.
- red light-emitting guest material constituting the light-emitting layer 14c examples include perylene derivatives represented by general formula (2), diketopyrrolopyrrole derivatives represented by general formula (3), and pyromethene complexes represented by general formula (4) described below.
- a pyran derivative of the general formula (5), or a styryl derivative of the general formula (6) is used.
- the details of the red luminescent guest material will be described.
- red light-emitting guest material for example, a compound represented by the following general formula (2) (diindeno [1,2,3-cd] perylene derivative) is used.
- X 1 to X 20 are each independently hydrogen, halogen, hydroxyl group, substituted or unsubstituted carbonyl group having 20 or less carbon atoms, substituted or unsubstituted carbon group having 20 or less carbon atoms.
- Carbonyl ester group substituted or unsubstituted alkyl group having 20 or less carbon atoms, substituted or unsubstituted alkenyl group having 20 or less carbon atoms, substituted or unsubstituted alkoxyl group having 20 or less carbon atoms, cyano group, nitro group, carbon A substituted or unsubstituted silyl group having 30 or fewer carbon atoms, a substituted or unsubstituted aryl group having 30 or fewer carbon atoms, a substituted or unsubstituted heterocyclic group having 30 or fewer carbon atoms, or a substituted or unsubstituted carbon group having 30 or fewer carbon atoms An amino group is shown.
- the aryl group represented by X 1 to X 20 in the general formula (2) is, for example, a phenyl group, 1-naphthyl group, 2-naphthyl group, fluorenyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 1-chrycenyl group, 6-chrycenyl group, 2-fluoranthenyl group, 3-fluoranthenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, o-tolyl Group, m-tolyl group, p-
- the heterocyclic group represented by X 1 to X 20 is a 5-membered or 6-membered aromatic heterocyclic group containing O, N, or S as a hetero atom, or a condensed polycyclic aromatic heterocyclic ring having 2 to 20 carbon atoms.
- Groups. Examples of these aromatic heterocyclic groups and condensed polycyclic aromatic heterocyclic groups include thienyl group, furyl group, pyrrolyl group, pyridyl group, quinolyl group, quinoxalyl group, imidazopyridyl group, and benzothiazole group.
- Representative examples include 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1-isobenzofuranyl group
- the amino group represented by X 1 to X 20 may be any of an alkylamino group, an arylamino group, an aralkylamino group, and the like. These preferably have an aliphatic group having 1 to 6 carbon atoms and / or an aromatic carbocyclic ring having 1 to 4 rings. Examples of such a group include a dimethylamino group, a diethylamino group, a dibutylamino group, a diphenylamino group, a ditolylamino group, a bisbiphenylylamino group, and a dinaphthylamino group.
- two or more of the above substituents may form a condensed ring, and may further have a substituent.
- diindeno [1,2,3-cd] perylene derivative suitably used as a red light-emitting guest material in the light-emitting layer 14c include the following compounds (2) -1 to (2) -8. .
- the present invention is not limited to these.
- -Diketopyrrolopyrrole derivatives As the red light emitting guest material, for example, a compound (diketopyrrolopyrrole derivative) represented by the following general formula (3) is used.
- Y ⁇ 1 > and Y ⁇ 2 > represent an oxygen atom or a substituted or unsubstituted imino group each independently.
- Y 3 to Y 8 are each independently hydrogen, halogen, a substituted or unsubstituted alkyl group having 20 or less carbon atoms, a substituted or unsubstituted alkenyl group having 20 or less carbon atoms, a substituted or unsubstituted group having 30 or less carbon atoms.
- a substituted aryl group, a substituted or unsubstituted heterocyclic group having 30 or less carbon atoms, or a substituted or unsubstituted amino group having 30 or less carbon atoms is shown.
- Ar 1 and Ar 2 represent a divalent group selected from a substituted or unsubstituted aromatic hydrocarbon group and a substituted or unsubstituted aromatic heterocyclic group.
- Y 3 substituted or unsubstituted aryl group represented by ⁇ Y 8 heterocyclic group represented by Y 3 ⁇ Y 8, amino groups further shows that Y 3 ⁇ Y 8 have the general formula It is the same as the group shown for the perylene derivative of (2). Further, two or more of the above substituents may form a condensed ring, and it may also have a substituent.
- diketopyrrolopyrrole derivative suitably used as the red light emitting guest material in the light emitting layer 14c include the following compounds (3) -1 to (3) -14.
- the present invention is not limited to these.
- red light emitting guest material for example, a compound (pyromethene complex) represented by the following general formula (4) is used.
- Z 1 to Z 9 are each independently hydrogen, halogen, a substituted or unsubstituted alkyl group having 20 or less carbon atoms, a substituted or unsubstituted alkenyl group having 20 or less carbon atoms, A substituted or unsubstituted alkoxyl group having 20 or less carbon atoms, a cyano group, a nitro group, a substituted or unsubstituted silyl group having 30 or less carbon atoms, a substituted or unsubstituted aryl group having 30 or less carbon atoms, a 30 or less carbon atoms A substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted amino group having 30 or less carbon atoms is shown.
- Z 1 substituted or unsubstituted aryl group represented by ⁇ Z 9 amino group represented by Z 1 ⁇ Z 9 is a heterocyclic group represented, and Z 1 ⁇ Z 9, the general formula ( This is the same as the group shown for the perylene derivative in 2). Further, two or more of the above substituents may form a condensed ring, and it may also have a substituent.
- red light-emitting guest material for example, a compound (pyran derivative) represented by the following general formula (5) is used.
- L 1 to L 6 are each independently hydrogen, a substituted or unsubstituted alkyl group having 20 or less carbon atoms, a substituted or unsubstituted alkenyl group having 20 or less carbon atoms, or a carbon number 20 or less substituted or unsubstituted alkoxyl group, cyano group, nitro group, substituted or unsubstituted silyl group having 30 or less carbon atoms, substituted or unsubstituted aryl group having 30 or less carbon atoms, substituted or unsubstituted 30 carbon atoms or less An unsubstituted heterocyclic group, or a substituted or unsubstituted amino group having 30 or less carbon atoms is shown.
- L 1 and L 4 or L 2 and L 3 may take a cyclic structure through hydrocarbon.
- L 1 ⁇ substituted or unsubstituted aryl group L 6 is shown, L 1 heterocyclic group represented by ⁇ L 6, and the amino group of L 1 ⁇ L 6 represents the general formula ( This is the same as the group shown for the perylene derivative in 2).
- L 1 and L 4 or L 2 and L 3 may have a cyclic structure through hydrocarbon, and two or more of the above substituents may form a condensed ring and may further have a substituent. .
- the following compounds (5) -1 to (5) -7 are exemplified as specific examples of the pyran derivative suitably used as the red light emitting guest material in the light emitting layer 14c.
- the present invention is not limited to these.
- red luminescent guest material for example, a compound (styryl derivative) represented by the following general formula (6) is used.
- T 1 to T 3 represent a substituted or unsubstituted aryl group having 30 or less carbon atoms or a substituted or unsubstituted heterocyclic group having 30 or less carbon atoms.
- T 4 represents a substituted or unsubstituted phenylene moiety that may have a cyclic structure with T 2 and T 3 .
- a substituted or unsubstituted aryl group represented by T 1 ⁇ T 3 is the same as the group represented by the perylene derivative of the general formula (2) .
- substituents may form a condensed ring and may further have a substituent.
- group further substituted with T 1 to T 4 include, for example, hydrogen, halogen, hydroxyl group, a substituted or unsubstituted carbonyl group having 20 or less carbon atoms, and a substituted or unsubstituted group having 20 or less carbon atoms.
- Carbonyl ester group substituted or unsubstituted alkyl group having 20 or less carbon atoms, substituted or unsubstituted alkenyl group having 20 or less carbon atoms, substituted or unsubstituted alkoxyl group having 20 or less carbon atoms, cyano group, nitro group, amino group Groups and the like.
- the amino group may be any of an alkylamino group, an arylamino group, an aralkylamino group, and the like. These preferably have an aliphatic group having 1 to 6 carbon atoms and / or an aromatic carbocyclic ring having 1 to 4 rings.
- Examples of such a group include a dimethylamino group, a diethylamino group, a dibutylamino group, a diphenylamino group, a ditolylamino group, a bisbiphenylylamino group, and a dinaphthylamino group.
- the pyran derivative of the general formula (5) or the styryl derivative of the general formula (6) preferably has a molecular weight of 2000 or less, more preferably 1500 or less, and particularly preferably 1000 or less. This is because there is a concern that if the molecular weight is large, the vapor deposition property may be deteriorated when an element is formed by vapor deposition.
- the photosensitizing layer 14d is a layer for transferring energy to the light emitting layer 14c and improving the light emission efficiency in the light emitting layer 14c.
- one feature is that the photosensitizing layer 14d is formed using a phosphorescent material.
- a phosphorescent material having a higher luminous efficiency than the fluorescent material is used as the photosensitizing layer, whereby the luminous efficiency from the light emitting layer 14c can be dramatically increased.
- Such a photosensitizing layer 14d has a guest-host relationship in which a phosphorescent light emitting material is used as a light emitting guest material and this is doped into the host material.
- the phosphorescent light emitting material (light emitting guest material) constituting the photosensitizing layer 14d emits phosphorescence having a shorter wavelength than the red light generated in the light emitting layer 14c containing the red light emitting guest material.
- the phosphorescent light emitting material light emitting guest material
- the photosensitizing layer 14d emits phosphorescence having a shorter wavelength than the red light generated in the light emitting layer 14c containing the red light emitting guest material.
- FIG. 2 shows a schematic diagram of the energy levels of the luminescent guest material contained in the luminescent layer 14c and the phosphorescent luminescent material (luminescent guest material) contained in the photosensitized layer 14d.
- the singlet excited state S1 (14c) and the ground state S0 (14c) are set in the luminescent guest material contained in the luminescent layer 14c.
- the phosphorescent light emitting material (light emitting guest material) contained in the photosensitizing layer 14d the triplet excited state T1 (14d) and the ground state S0 (14d) are set. It is desirable that the energy difference between each excited state and the ground state has a relationship of
- phosphorescent materials are selected from iridium complexes, platinum complexes, rhenium complexes, osmium complexes, ruthenium complexes, and gold complexes. Moreover, it is preferable to select and use a phosphorescent material having high luminous efficiency from these materials, and for example, it is selected from iridium complexes.
- the host material that constitutes the photosensitizing layer 14d is an aromatic hydrocarbon derivative having 6 to 60 carbon atoms, or an organic material formed by linking them.
- specific examples thereof include carbazole derivatives, indene derivatives, phenanthrene derivatives, pyrene derivatives, naphthacene derivatives, triphenylene derivatives, anthracene derivatives, perylene derivatives, picene derivatives, fluoranthene derivatives, acephenanthrylene derivatives, pentaphen derivatives, pentacene derivatives.
- Coronene derivatives, butadiene derivatives, stilbene derivatives, tris (8-quinolinolato) aluminum complexes, bis (benzoquinolinolato) beryllium complexes, and the like can be used.
- the host materials having the highest luminous efficiency are selected and used for each luminescent guest material.
- a carbazole derivative is preferably used as such a host material.
- the photosensitizing layer 14d having such a configuration is provided in contact with the light emitting layer 14c. For this reason, this photosensitizing layer 14d is provided between the light emitting layer 14c and the cathode 15, for example. However, since it is important that the photosensitizing layer 14d is provided in contact with the light emitting layer 14c, it may be provided between the light emitting layer 14c and the anode 13 in contact with the light emitting layer 14c. .
- the electron transport layer 14e is for transporting electrons injected from the cathode 15 to the light emitting layer 14c.
- Examples of the material for the electron transport layer 14e include quinoline, perylene, phenanthroline, bisstyryl, pyrazine, triazole, oxazole, oxadiazole, fluorenone, and derivatives or metal complexes thereof.
- Alq3 8-hydroxyquinoline aluminum
- anthracene naphthalene
- phenanthrene pyrene
- anthracene perylene
- butadiene coumarin
- acridine stilbene
- 1,10-phenanthroline or derivatives or metal complexes thereof
- the organic layer 14 is not limited to such a layer structure, and it is sufficient that at least the light emitting layer 14c and the photosensitizing layer 14d are provided in contact therewith, and other laminated structures as required. Can be selected.
- the light emitting layer 14c may be provided in the organic electroluminescent element 11 as a hole transporting light emitting layer, an electron transporting light emitting layer, or a charge transporting light emitting layer.
- each layer constituting the organic layer 14 described above, for example, the hole injection layer 14a, the hole transport layer 14b, the light emitting layer 14c, the photosensitizing layer 14d, and the electron transport layer 14e is a laminated structure including a plurality of layers. It may be.
- the cathode 15 provided on the organic layer 14 having such a configuration has, for example, a two-layer structure in which a first layer 15a and a second layer 15b are stacked in this order from the organic layer 14 side.
- the first layer 15a is made of a material having a small work function and good light transmittance.
- a material having a small work function and good light transmittance examples include lithium oxide (Li 2 O) which is an oxide of lithium (Li), cesium carbonate (Cs 2 CO 3 ) which is a composite oxide of cesium (Cs), and further oxidation of these. Mixtures of oxides and composite oxides can be used. Further, the first layer 15a is not limited to such a material.
- alkaline earth metals such as calcium (Ca) and barium (Ba)
- alkali metals such as lithium and cesium, and indium ( In)
- magnesium (Mg) magnesium
- other metals having a low work function
- oxides and composite oxides, fluorides, and the like of these metals, alone or these metals and oxides and composite oxides You may use it, improving stability as a mixture or an alloy.
- the second layer 15b is made of a thin film using a light-transmitting layer such as MgAg.
- the second layer 15b may be a mixed layer containing an organic light emitting material such as an aluminum quinoline complex, a styrylamine derivative, or a phthalocyanine derivative.
- a layer having optical transparency such as MgAg may be additionally provided as the third layer.
- the cathode 15 when the driving method of the display device configured using the organic electroluminescent element 11 is an active matrix method, the cathode 15 includes the organic layer 14 and the above-described illustration omitted here.
- a solid film is formed on the substrate 12 while being insulated from the anode 13 by the insulating film, and is used as a common electrode of each pixel.
- the cathode 15 is not limited to the laminated structure as described above, and an optimum combination and laminated structure may be taken according to the structure of the device to be manufactured.
- the configuration of the cathode 15 of the above embodiment includes an inorganic layer (first layer 15a) that promotes functional separation of each electrode layer, that is, electron injection into the organic layer 14, and an inorganic layer (second layer 15b) that controls the electrode.
- first layer 15a that promotes functional separation of each electrode layer
- second layer 15b that controls the electrode.
- the inorganic layer that promotes electron injection into the organic layer 14 may also serve as the inorganic layer that controls the electrode, and these layers may be configured as a single layer structure.
- the current applied to the organic electroluminescent element 11 having the above-described configuration is usually a direct current, but a pulse current or an alternating current may be used.
- the current value and the voltage value are not particularly limited as long as the element is not destroyed. However, considering the power consumption and life of the organic electroluminescent element, it is desirable to emit light efficiently with as little electrical energy as possible.
- the cathode 15 is configured using a transflective material. Then, light emitted by multiple interference between the light reflecting surface on the anode 13 side and the light reflecting surface on the cathode 15 side is extracted from the cathode 15 side.
- the optical distance between the light reflecting surface on the anode 13 side and the light reflecting surface on the cathode 15 side is defined by the wavelength of light to be extracted, and the film thickness of each layer is set so as to satisfy this optical distance.
- the organic electroluminescent element 11 having such a configuration is covered with a protective layer (passivation layer) in order to prevent deterioration of the organic material due to moisture, oxygen, etc. in the atmosphere. It is preferable to use in.
- the protective film includes silicon nitride (typically Si 3 N 4 ), silicon oxide (typically SiO 2 ) film, silicon nitride oxide (SiN x O y: composition ratio X> Y) film, silicon oxynitride ( A SiOxNy: composition ratio X> Y) film, a thin film mainly composed of carbon such as DLC (Diamond Like Carbon), a CN (Carbon Nanotube) film, or the like is used.
- These films are preferably single-layered or laminated.
- a protective layer made of nitride is preferably used because it has a dense film quality and has an extremely high blocking effect against moisture, oxygen, and other impurities that adversely affect the organic electroluminescent element 11.
- the present invention has been described in detail by exemplifying a case where the organic electroluminescent element is a top emission type.
- the organic electroluminescence device of the present invention is not limited to the application to the top emission type, and can be widely applied to a configuration in which an organic layer having at least a light emitting layer is sandwiched between an anode and a cathode. is there.
- the cathode, the organic layer, and the anode are laminated in sequence, and the electrode located on the substrate side (lower electrode as the cathode or anode) is made of a transparent material and located on the opposite side of the substrate
- the electrode (upper electrode as a cathode or anode) to be formed is made of a reflective material, so that the present invention can be applied to a bottom emission type organic electroluminescence device in which light is extracted only from the lower electrode side.
- the organic electroluminescent element of the present invention may be an element formed by a pair of electrodes (anode and cathode) and an organic layer sandwiched between the electrodes. For this reason, it is not limited to what comprised only a pair of electrode and organic layer, and other components (for example, an inorganic compound layer and an inorganic component) coexist in the range which does not impair the effect of this invention. Is not to be excluded.
- the current efficiency may be increased as compared with an element having no photosensitizing layer 14d. confirmed.
- the photosensitizing layer 14d that emits green light is stacked on the red light emitting layer 14c, color mixing due to light emission from the photosensitizing layer 14d does not occur even when an electric field is applied. Luminescence can be obtained.
- the photosensitizing layer 14d holes that have penetrated the red light emitting layer 14c and electrons injected through the electron transport layer 14e are recombined, but are released by the recombination. It is considered that this energy acts to excite electrons of the host material constituting the adjacent red light emitting layer 14c and contributes to light emission in the red light emitting layer 14c.
- Such a phenomenon is caused by a phenomenon in which the target red light emitting layer hardly emits light when the photosensitizing layer 14d is composed only of the host material, as shown as a comparative example for the following examples. You can analogize.
- the organic electroluminescent element 11 having the above-described configuration, it is possible to improve the luminous efficiency of red emitted light while maintaining the color purity.
- the luminance life of the organic electroluminescent element 11 can be improved and the power consumption can be reduced by such a significant improvement in luminous efficiency.
- FIG. 3A and 3B are diagrams illustrating an example of the display device 10 according to the embodiment.
- FIG. 3A is a schematic configuration diagram
- FIG. 3B is a configuration diagram of a pixel circuit.
- an embodiment in which the present invention is applied to an active matrix display device 10 using an organic electroluminescent element 11 as a light emitting element will be described.
- a display area 12a and a peripheral area 12b are set on the substrate 12 of the display device 10.
- the display region 12a is configured as a pixel array section in which a plurality of scanning lines 21 and a plurality of signal lines 23 are wired vertically and horizontally, and one pixel a is provided corresponding to each intersection. Each of these pixels a is provided with one of the organic electroluminescent elements 11R (11), 11G, and 11B.
- a scanning line driving circuit b that scans the scanning lines 21 and a signal line driving circuit c that supplies a video signal (that is, an input signal) corresponding to the luminance information to the signal lines 23 are arranged. Yes.
- the pixel circuit provided in each pixel a includes, for example, one of the organic electroluminescent elements 11R (11), 11G, and 11B, a driving transistor Tr1, and a writing transistor (sampling transistor). It is composed of Tr2 and a holding capacitor Cs. Then, the video signal written from the signal line 23 via the write transistor Tr2 is held in the holding capacitor Cs by driving by the scanning line driving circuit b, and a current corresponding to the held signal amount is supplied to each organic electroluminescent element 11R. (11), 11G, and 11B are supplied, and the organic electroluminescent elements 11R (11), 11G, and 11B emit light with luminance according to the current value.
- a capacitor element may be provided in the pixel circuit, or a plurality of transistors may be provided to configure the pixel circuit. Further, a necessary drive circuit is added to the peripheral region 12b according to the change of the pixel circuit.
- FIG. 4 shows a first example of a cross-sectional configuration of the main part in the display area of the display device 10.
- a driving transistor In the display region of the substrate 12 on which the organic electroluminescent elements 11R (11), 11G, and 11B are provided, although not shown here, a driving transistor, a writing transistor, a scanning line, And a signal line (see FIG. 3), and an insulating film is provided so as to cover them.
- the organic electroluminescence elements 11R (11), 11G, and 11B are arranged on the substrate 12 covered with the insulating film.
- Each of the organic electroluminescent elements 11R (11), 11G, and 11B is configured as a top-emitting element that extracts light from the side opposite to the substrate 12.
- each organic electroluminescent element 11R (11), 11G, 11B is patterned for each element.
- Each anode 13 is connected to a drive transistor of the pixel circuit through a connection hole formed in an insulating film covering the surface of the substrate 12.
- each anode 13 is covered with an insulating film 30, and the central portion of the anode 13 is exposed at the opening provided in the insulating film 30.
- the organic layer 14 is patterned so as to cover the exposed portion of the anode 13, and the cathode 15 is provided as a common layer covering each organic layer 14.
- the red light emitting element 11R is configured as the organic electroluminescent element (11) of the embodiment described with reference to FIG.
- the green light emitting element 11G and the blue light emitting element 11B may have a normal element configuration.
- the organic layer 14 provided on the anode 13 uses, for example, the hole injection layer 14a, the hole transport layer 14b, and the naphthacene derivative as the host material in order from the anode 13 side.
- a red light-emitting layer 14c-R (14c), a photosensitizing layer 14d obtained by doping a host material with a light-emitting guest material that emits light in the green region, and an electron transport layer 14e are stacked.
- the organic layers in the green light emitting element 11G and the blue light emitting element 11B are, for example, in order from the anode 13 side, a hole injection layer 14a, a hole transport layer 14b, light emitting layers 14c-G and 14c-B for each color, and electron transport.
- the layer 14e is laminated in this order.
- the photosensitizing layer 14d in the red light emitting element 11R (11) is obtained by doping a green phosphorescent light emitting material as a light emitting guest material.
- a green phosphorescent light emitting material for example, the same as the green light emitting layer 14c-G in the green light emitting element 11G. It may be a configuration (material) or another configuration.
- each layer other than the light emitting layers 14c-R, 14c-G, 14c-B and the photosensitizing layer 14d includes the anode 13 and the cathode 15 in each organic electroluminescent element 11R, 11G, 11B. It may be comprised with the same material, and is comprised using each material demonstrated using FIG.
- the plurality of organic electroluminescent elements 11R (11), 11G, and 11B provided as described above are covered with a protective film (not shown).
- the protective film is provided so as to cover the entire display area where the organic electroluminescent elements 11R, 11G, and 11B are provided.
- each layer from the anode 13 to the cathode 15 constituting the red light emitting element 11R (11), the green light emitting element 11G, and the blue light emitting element 11B is formed by a vacuum deposition method, an ion beam method (EB method), a molecular beam epitaxy method. (MBE method), sputtering method, Organic (Vapor Phase Deposition (OVPD) method and the like.
- EB method ion beam method
- MBE method molecular beam epitaxy method
- sputtering method Organic (Vapor Phase Deposition (OVPD) method and the like.
- the organic layer 14 patterned for each of the organic electroluminescent elements 11R (11), 11G, and 11B is formed by, for example, a vapor deposition method or a transfer method using a mask.
- the organic layer 14c is applied by a laser transfer method, a spin coating method, a dipping method, a doctor blade method, a discharge coating method, a spray coating method, an inkjet method, an offset printing method, a relief printing method, Formation by wet processes such as intaglio printing, screen printing, and microgravure coating is also possible.
- a dry process and a wet process may be used in combination. Absent.
- the organic electroluminescent element (11) having the configuration of the present invention described with reference to FIG. 1 is used as the red light emitting element 11R.
- the red light emitting element 11R (11) has high light emission efficiency while maintaining the red light emission color. Therefore, by combining the red light emitting element 11R (11) with the green light emitting element 11G and the blue light emitting element 11B, full color display with high color expression can be performed.
- the use of the organic electroluminescent element (11) having high luminous efficiency can improve the luminance life and reduce the power consumption in the display device 10. Therefore, it can be suitably used as a flat panel display such as a wall-mounted TV or a flat light emitter, and can be applied to a light source such as a copying machine or a printer, a light source such as a liquid crystal display or an instrument, a display board, a marker lamp, etc. It becomes.
- FIG. 5 shows a second example of the cross-sectional configuration of the main part in the display area of the display device 10.
- the display device 10 of the second example shown in FIG. 5 is different from the first example shown in FIG. 4 in that the photosensitizing layer 14d (14c-G) of the red light emitting element 11R (11) and the green light emission.
- the light emitting layer 14c-G of the element 11G is formed as a common continuous pattern.
- the electron transport layer 14e is also formed as a continuous pattern of a common layer in all pixels.
- the configuration may be the same as in the first example.
- the same effect as that of the first example can be obtained.
- the photosensitizing layer 14d (14c-G) and the light emitting layer 14c-G are formed in a continuous pattern as a common layer, and the electron transport layer 14e is simultaneously formed in all pixels. Since the film can be formed, the manufacturing process of the display device 10 can be simplified.
- FIG. 6 shows a third example of the cross-sectional configuration of the main part in the display area of the display device 10.
- layers other than the anode 13 and the light emitting layers 14c-R, 14c-G, and 14c-B are shared in the organic electroluminescent elements 11R (11), 11G, and 11B.
- the other structure may be the same as that of the second example shown in FIG. That is, as compared with the second example of FIG. 5, the hole injection layer 14a and the hole transport layer 14b below the light emitting layer are also used as the common layer.
- FIG. 7 shows a fourth example of the cross-sectional configuration of the main part in the display area of the display device 10.
- the organic electroluminescent elements 11R, 11G, and 11B may have a common layer above the light emitting layers 14c-R and 14c-B.
- the green light emitting layer 14c-G that also serves as the photosensitizing layer 14d, the electron transport layer 14e, and the cathode 15 are formed as a continuous pattern common to the entire display region, and the others are used as patterned layers. .
- the green light emitting layer 14c-G serving as a common layer for all pixels is provided as the photosensitizing layer 14d in the red light emitting element 11R (11).
- the green light emitting layer 14c-G is also laminated on the blue light emitting element 11B. Even in such a configuration, such a configuration is adopted when the film thickness of the blue light emitting layer 14c-B is sufficiently thick, or when the blue light emitting center is localized at the interface of the hole transport layer 14b. Even in such a case, it is sufficiently possible to obtain blue light emission with good chromaticity.
- each of the organic electroluminescent elements 11R (11), 11G, and 11B only the blue emitted light is extracted from the blue light emitting element 11B by configuring the structure of the organic layer as a cavity structure that extracts the emitted light of each color. You may comprise.
- the layers from the green light emitting layer 14c-G (photosensitized layer 14d) to the upper layer are collectively formed on the display region using a large-diameter area mask. be able to. Therefore, the manufacturing process of the display device 10 can be simplified.
- the hole injection layer 14a and the hole transport layer 14b below the light emitting layer can also be used as a common layer (continuous pattern) in the entire display region. It is possible to simplify the manufacturing process of the device 10.
- the display device of the present invention can be applied to a passive matrix display device, and the same effect can be obtained.
- the display device according to the present invention described above includes a module-shaped one having a sealed configuration as disclosed in FIG.
- the sealing portion 31 is provided so as to surround the display region 12a that is the pixel array portion, and the sealing portion 31 is used as an adhesive and is attached to a facing portion (sealing substrate 32) such as transparent glass.
- a facing portion such as transparent glass.
- the transparent sealing substrate 32 may be provided with a color filter, a protective film, a light shielding film, and the like.
- the substrate 12 as a display module in which the display area 12a is formed may be provided with a flexible printed board 33 for inputting / outputting signals and the like from the outside to the display area 12a (pixel array portion).
- the display device according to the present invention described above is input to various electronic devices shown in FIGS. 9 to 13 such as digital cameras, notebook personal computers, mobile terminal devices such as mobile phones, and video cameras.
- the video signal generated or the video signal generated in the electronic device can be applied to a display device of an electronic device in any field for displaying as an image or a video.
- An example of an electronic device to which the present invention is applied will be described below.
- FIG. 9 is a perspective view showing a television to which the present invention is applied.
- the television according to this application example includes a video display screen unit 101 including a front panel 102, a filter glass 103, and the like, and is created by using the display device according to the present invention as the video display screen unit 101.
- FIG. 10A and 10B are diagrams showing a digital camera to which the present invention is applied, in which FIG. 10A is a perspective view seen from the front side, and FIG. 10B is a perspective view seen from the back side.
- the digital camera according to this application example includes a light emitting unit 111 for flash, a display unit 112, a menu switch 113, a shutter button 114, and the like, and is manufactured by using the display device according to the present invention as the display unit 112.
- FIG. 11 is a perspective view showing a notebook personal computer to which the present invention is applied.
- a notebook personal computer according to this application example includes a main body 121 including a keyboard 122 that is operated when characters and the like are input, a display unit 123 that displays an image, and the like. It is produced by using.
- FIG. 12 is a perspective view showing a video camera to which the present invention is applied.
- the video camera according to this application example includes a main body 131, a lens 132 for shooting an object on a side facing forward, a start / stop switch 133 at the time of shooting, a display unit 134, and the like. It is manufactured by using such a display device.
- FIG. 13 is a diagram showing a portable terminal device to which the present invention is applied, for example, a cellular phone, in which (A) is a front view in an opened state, (B) is a side view thereof, and (C) is in a closed state. (D) is a left side view, (E) is a right side view, (F) is a top view, and (G) is a bottom view.
- the mobile phone according to this application example includes an upper housing 141, a lower housing 142, a connecting portion (here, a hinge portion) 143, a display 144, a sub display 145, a picture light 146, a camera 147, and the like. And the sub display 145 is manufactured by using the display device according to the present invention.
- Examples 1 to 3 a top emission organic material in which an ITO transparent electrode with a film thickness of 12.5 nm is laminated on an Ag alloy (reflection layer) with a film thickness of 190 nm as an anode 13 on a substrate 12 made of a glass plate of 30 mm ⁇ 30 mm. A cell for an electroluminescent element was produced.
- a film made of m-MTDATA represented by the following structural formula (101) is formed to a film thickness of 12 nm (deposition rate: 0.2 to 0.4 nm / sec).
- m-MTDATA is 4,4 ′, 4 ′′ -tris (phenyl-m-tolylamino) triphenylamine.
- ⁇ -NPD represented by the following structural formula (102) was formed with a film thickness of 12 nm (deposition rate: 0.2 to 0.4 nm / sec).
- ⁇ -NPD is N, N′-bis (1-naphthyl) -N, N′-diphenyl [1,1′-biphenyl] -4,4′-diamine.
- a light emitting layer 14c having a thickness of 30 nm was deposited on the hole transport layer 14b by vapor deposition.
- rubrene was used as a host material
- dibenzo [f, f ′] diindeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene represented by the following structural formula (103) was used.
- the derivative was doped as a red light emitting guest material at a relative film thickness ratio of 1%.
- a photosensitizing layer 14d having a thickness of 25 nm was deposited on the light emitting layer 14c thus formed.
- CBP 4,4′-bis (carbazol-9-yl) -biphenyl
- Ir (ppy) represented by the following structural formula (105) was used.
- 3 was doped as a luminescent guest material (phosphorescent material).
- the luminescent guest material (phosphorescent material) was used in Examples 1 to 3 with 5%, 10%, and 15% doping amounts (relative film thickness ratio).
- Alq3 (8-hydroxyquinoline aluminum) represented by the following structural formula (106) was deposited with a thickness of 10 nm.
- the cathode 15 As the first layer 15a, a film made of LiF was formed with a film thickness of about 0.3 nm (deposition rate 0.01 nm / sec.) By a vacuum evaporation method. Finally, a 10 nm-thick MgAg film was formed as the second layer 15b of the cathode 15 on the first layer 15a by vacuum deposition.
- organic electroluminescent elements of Examples 1 to 3 were produced.
- Examples 4 and 5 In the formation of the photosensitizing layer 14d in the manufacturing procedure of the organic electroluminescent device described in Examples 1 to 3, the materials represented by the structural formula (107) and the structural formula (108) are used as the light-emitting guest material (phosphorescent material). Each was used. The doping amount of the luminescent guest material (phosphorescent material) was 10% in both Examples 4 and 5. Other than this, organic electroluminescent elements were fabricated in the same manner as in Examples 1 to 3.
- Examples 6 and 7 In the formation of the photosensitizing layer 14d in the manufacturing procedure of the organic electroluminescence device described in Examples 1 to 3, the material represented by the structural formula (109) is used as the host material, and the structure as the light-emitting guest material (phosphorescent material). The materials shown in Formula (110) and Structural Formula (111) were used. The doping amount of the luminescent guest material was 10% in both Examples 6 and 7. Other than this, organic electroluminescent elements were fabricated in the same manner as in Examples 1 to 3.
- the photosensitizing layer 14d doped with a green or blue phosphorescent light emitting material as a light emitting guest material in the host material was laminated on the red light emitting layer 14c. Nevertheless, red light emission with a color coordinate (0.64, 0.34) of the emitted light was observed, and there was no influence of color mixture derived from green light emission.
- the color coordinates of the emitted light are (0.64, 0.34).
- the red light emitted from the red light emitting layer 14c is extracted regardless of the light emitting guest material (phosphorescent light emitting material) of the photosensitizing layer 14d. It was done.
- a material selected from known organic materials as a host material and a dopant material constituting the red light-emitting layer 14c is used, and is made adjacent to the light-emitting layer 14c.
- the photosensitizing layer 14d containing various green or blue light emitting guest materials phosphorescent light emitting materials
- a large luminous efficiency (current) is maintained while maintaining the red color purity. It was confirmed that it was possible to improve efficiency.
- SYMBOLS 10 Display apparatus, 11 ... Organic electroluminescent element, 11R ... Red light emitting element, 11B ... Blue light emitting element (blue light emitting organic electroluminescent element), 11G ... Green light emitting element (green light emitting organic electroluminescent element), 12 ... Substrate, 13 ... anode, 14 ... organic layer, 14c ... light emitting layer, 14d ... photosensitized layer, 15 ... cathode
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Abstract
Description
図1は、本発明の有機電界発光素子を模式的に示す断面図である。この図に示す有機電界発光素子11は、基板12上に、陽極13、有機層14、および陰極15をこの順に積層してなる。このうち有機層14は、陽極13側から順に、例えば正孔注入層14a、正孔輸送層14b、発光層14c、光増感層14d、および電子輸送層14eを積層してなるものである。
基板12は、その一主面側に有機電界発光素子11が配列形成される支持体であって、公知のものであって良く、例えば、石英、ガラス、金属箔、もしくは樹脂製のフィルムやシートなどが用いられるこの中でも石英やガラスが好ましく、樹脂製の場合には、その材質としてポリメチルメタクリレート(PMMA)に代表されるメタクリル樹脂類、ポリエチレンテレフタレート(PET)、ポリエチレンナフタレート(PEN)、ポリブチレンナフタレート(PBN)などのポリエステル類、もしくはポリカーボネート樹脂などが挙げられるが、透水性や透ガス性を抑える積層構造、表面処理を行うことが必要である。
陽極13には、効率良く正孔を注入するために電極材料の真空準位からの仕事関数が大きいもの、例えばアルミニウム(Al)、クロム(Cr)、モリブテン(Mo)、タングステン(W)、銅(Cu)、銀(Ag)、金(Au)の金属およびその合金さらにはこれらの金属や合金の酸化物等、または、酸化スズ(SnO2)とアンチモン(Sb)との合金、ITO(インジウムチンオキシド)、InZnO(インジウ亜鉛オキシド)、酸化亜鉛(ZnO)とアルミニウム(Al)との合金、さらにはこれらの金属や合金の酸化物等が、単独または混在させた状態で用いられる。
正孔注入層14aは、発光層14cへの正孔注入効率を高めるためのものである。このような正孔注入層14aの材料としては、例えば、ベンジン、スチリルアミン、トリフェニルアミン、ポルフィリン、トリフェニレン、アザトリフェニレン、テトラシアノキノジメタン、トリアゾール、イミダゾール、オキサジアゾール、ポリアリールアルカン、フェニレンジアミン、アリールアミン、オキザゾール、アントラセン、フルオレノン、ヒドラゾン、スチルベンあるいはこれらの誘導体、または、ポリシラン系化合物、ビニルカルバゾール系化合物、チオフェン系化合物あるいはアニリン系化合物等の複素環式共役系のモノマー、オリゴマーあるいはポリマーを用いることができる。
正孔輸送層14bは、正孔注入層14aと同様に発光層14cへの正孔注入効率を高めるためのものである。このような正孔輸送層14bは、上述した正孔注入層14aと同様の材料の中から選択した材料を用いて構成される。
発光層14cは、陽極13と陰極15とに対する電圧印加時に、陽極13側から注入された正孔と、陰極15側から注入された電子とが再結合する領域である。本実施形態においては、この発光層14cの構成が一つの特徴である。つまり発光層14cは、母骨格が環員数4~7の多環式芳香族炭化水素化合物をホスト材料として用いたもので、このホスト材料に対して赤色の発光性ゲスト材料がドーピングされており、赤色の発光光を発生する。
赤色の発光性ゲスト材料として、例えば下記一般式(2)に示す化合物(ジインデノ[1,2,3-cd]ペリレン誘導体)が用いられる。
ただし本発明は、なんらこれらに限定されるものではない。
赤色の発光性ゲスト材料として、例えば下記一般式(3)に示す化合物(ジケトピロロピロール誘導体)が用いられる。
赤色の発光性ゲスト材料として、例えば下記一般式(4)に示す化合物(ピロメテン錯体)が用いられる。
赤色の発光性ゲスト材料として、例えば下記一般式(5)に示す化合物(ピラン誘導体)が用いられる。
赤色の発光性ゲスト材料として、例えば下記一般式(6)に示す化合物(スチリル誘導体)が用いられる。
光増感層14dは、発光層14cに対してエネルギーを移動させ、発光層14cにおける発光効率を向上させるための層である。本実施形態においては、燐光発光材料を用いて光増感層14dが構成されているところが1つの特徴である。これにより、原理的に蛍光材料よりも発光効率の高い燐光材料を光増感層として用いることで、発光層14cからの発光効率を飛躍的に高めることが出来る。
電子輸送層14eは、陰極15から注入される電子を発光層14cに輸送するためのものである。電子輸送層14eの材料としては、例えば、キノリン、ペリレン、フェナントロリン、ビススチリル、ピラジン、トリアゾール、オキサゾール、オキサジアゾール、フルオレノン、またはこれらの誘導体や金属錯体が挙げられる。具体的には、トリス(8-ヒドロキシキノリン)アルミニウム(略称Alq3 )、アントラセン、ナフタレン、フェナントレン、ピレン、アントラセン、ペリレン、ブタジエン、クマリン、アクリジン、スチルベン、1,10-フェナントロリンまたはこれらの誘導体や金属錯体が挙げられる。
次に、このような構成の有機層14上に設けられる陰極15は、例えば、有機層14側から順に第1層15a、第2層15bを積層させた2層構造で構成されている。
図3は、実施形態の表示装置10の一例を示す図であり、図3(A)は概略構成図、図3(B)は画素回路の構成図である。ここでは、発光素子として有機電界発光素子11を用いたアクティブマトリックス方式の表示装置10に本発明を適用した実施形態を説明する。
図4には、上記表示装置10の表示領域における主要部の断面構成の第1の例を示す。
図5には、表示装置10の表示領域における主要部の断面構成の第2の例を示す。
図6には、表示装置10の表示領域における主要部の断面構成の第3の例を示す。
図7には、表示装置10の表示領域における主要部の断面構成の第4の例を示す。
また以上説明した本発明に係る表示装置は、図9~図13に示す様々な電子機器、例えば、デジタルカメラ、ノート型パーソナルコンピュータ、携帯電話等の携帯端末装置、ビデオカメラなど、電子機器に入力された映像信号、若しくは、電子機器内で生成した映像信号を、画像若しくは映像として表示するあらゆる分野の電子機器の表示装置に適用することが可能である。以下に、本発明が適用される電子機器の一例について説明する。
先ず、30mm×30mmのガラス板からなる基板12上に、陽極13として、膜厚が190nmのAg合金(反射層)上に、膜厚12.5nmのITO透明電極を積層した上面発光用の有機電界発光素子用のセルを作製した。
実施例1~3で説明した有機電界発光素子の作製手順おける光増感層14dの形成で、発光性ゲスト材料(燐光発光材料)として構造式(107),構造式(108)に示す材料をそれぞれ用いた。発光性ゲスト材料(燐光発光材料)のドーピング量は、実施例4,5とも10%とした。これ以外は、実施例1~3と同様にして有機電界発光素子を作製した。
実施例1~3で説明した有機電界発光素子の作製手順おける光増感層14dの形成で、ホスト材料として構造式(109)に示す材料を用い、発光性ゲスト材料(燐光発光材料)として構造式(110),構造式(111)に示す材料をそれぞれ用いた。発光性ゲスト材料のドーピング量は、実施例6,7とも10%とした。これ以外は、実施例1~3と同様にして有機電界発光素子を作製した。
実施例1~3で説明した有機電界発光素子の作製手順における光増感層14dの形成を行わず、代わりにAlq3(8-ヒドロキシキノリンアルミニウム)からなる電子輸送層の膜厚を45nmに厚膜化した。これ以外は、実施例1~3と同様に行った。
実施例1~3で説明した有機電界発光素子の作製手順おける光増感層14dの形成で、発光性ゲスト材料(燐光発光材料)をドーパントせずにホスト材料のみで光増感層14dを形成した。これ以外は、実施例1~3と同様に行った。
以上の実施例1~7および比較例1,2で作製した各有機電界発光素子について、電流密度10mA/cm2での駆動時における駆動電圧(V)、電流効率(cd/A)、色座標(x、y)を測定した。この結果を、下記表1に示す。
Claims (12)
- 陽極と、
赤色の発光性ゲスト材料と共に、母骨格が環員数4~7の多環式芳香族炭化水素化合物からなるホスト材料を含有する発光層と、
有機材料からなる燐光発光材料を含有し前記発光層に隣接して積層された光増感層と、
前記陽極との間に前記発光層および前記光増感層を挟持する状態で設けられた陰極とを有する
有機電界発光素子。 - 前記燐光発光材料は、前記赤色の発光性ゲスト材料よりも短波長の燐光を発光する
請求項1に記載の有機電界発光素子。 - 前記燐光発光材料は、イリジウム錯体、白金錯体、レニウム錯体、オスミウム錯体、ルテニウム錯体、および金錯体から選択される
請求項1または2に記載の有機電界発光素子。 - 前記光増感層は、前記発光層に隣接して当該発光層と前記陰極との間に設けられている
請求項1~3のうちの何れか1項に記載の有機電界発光素子。 - 前記光増感層は、前記燐光発光材料を発光性ゲスト材料とし、炭素数6以上60以下の芳香族炭化水素の誘導体またはその連結からなる有機材料をホスト材料として含有している
請求項1~4のうちの何れか1項に記載の有機電界発光素子。 - 前記発光層のホスト材料を構成する多環式芳香族炭化水素化合物の母骨格が、ピレン、ベンゾピレン、クリセン、ナフタセン、ベンゾナフタセン、ジベンゾナフタセン、ペリレン、コロネンから選択された
請求項1~5のちの何れか1項に記載の有機電界発光素子。 - 前記発光層のホスト材料として、下記一般式(1)に示す化合物が用いられている
請求項1~6のうちの何れか1項に記載の有機電界発光素子。
- 前記発光層で発生した赤色の発光光が、前記陽極と陰極との間の何れかの層間において多重干渉して当該陽極または陰極の一方側から取り出される
請求項1~7のうちの何れか1項に記載の有機電界発光素子。 - 陽極と、
赤色の発光性ゲスト材料と共に、母骨格が環員数4~7の多環式芳香族炭化水素化合物からなるホスト材料を含有する発光層と、
有機材料からなる燐光発光材料を含有し前記発光層に隣接して積層された光増感層と、
前記陽極との間に前記発光層および前記光増感層を挟持する状態で設けられた陰極と、
前記陰極と前記陽極との間に前記発光層と前記光増感層とを挟持してなる有機電界発光素子が配列される基板とを備えた
表示装置。 - 前記有機電界発光素子が、赤色発光素子として複数の画素のうちの一部の画素に設けられている
請求項9に記載の表示装置。 - 前記赤色発光素子として設けられた前記有機電界発光素子の光増感層は、前記基板上に設けられた当該赤色発光素子以外の有機電界発光素子における発光層として、複数の画素にわたる連続パターンの形状で設けられている
請求項10に記載の表示装置。 - 前記基板上には、前記赤色発光素子と共に、青色発光性の有機電界発光素子および緑色発光性の有機電界発光素子が設けられている
請求項10または11に記載の表示装置。
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CN105702877B (zh) * | 2016-04-05 | 2018-11-06 | 深圳市华星光电技术有限公司 | Oled显示面板及其制备方法 |
JP2017220528A (ja) * | 2016-06-06 | 2017-12-14 | 株式会社Joled | 有機el表示パネル |
CN109791998B (zh) * | 2016-09-30 | 2021-02-05 | 夏普株式会社 | 显示装置及其制造方法 |
JP2018181492A (ja) | 2017-04-06 | 2018-11-15 | 株式会社ジャパンディスプレイ | 表示装置及びその製造方法 |
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TW202030902A (zh) * | 2018-09-12 | 2020-08-16 | 德商麥克專利有限公司 | 電致發光裝置 |
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US8569747B2 (en) | 2013-10-29 |
CN102113146A (zh) | 2011-06-29 |
US20110303903A1 (en) | 2011-12-15 |
JP2010040735A (ja) | 2010-02-18 |
KR20110044213A (ko) | 2011-04-28 |
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