WO2005062675A1 - 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置および表示装置 - Google Patents
有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置および表示装置 Download PDFInfo
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Definitions
- Organic electorifice luminescent element material organic electoral luminescent element, lighting device and display device
- the present invention relates to an organic electroluminescent device, an illumination device, and a display device, and more particularly, to an organic electroluminescent device having excellent emission luminance, luminous efficiency, and durability, a lighting device, and a display device having the same.
- ELD electoral luminescence display
- ELD components include an inorganic electorescence luminescent element and an organic electorescence luminescence element (hereinafter also referred to as an organic EL element).
- Inorganic electoluminescence devices require a high AC voltage to drive a power light emitting device that has been used as a planar light source.
- an organic EL element has a configuration in which a light-emitting layer containing a compound that emits light is sandwiched between a cathode and an anode. (Exciton) is generated, and the device emits light by using the light emission (fluorescence phosphorescence) when this exciton is deactivated. It can emit light at a voltage of several volts to several tens of volts. Furthermore, since it is a self-luminous type, it has a wide viewing angle and is a thin-film type solid-state element with high visibility, it is attracting attention from the viewpoint of space saving and portability.
- Non-Patent Document 1 Since Princeton University reported an organic EL device using phosphorescence emission from an excited triplet (for example, see Non-Patent Document 1), research on materials exhibiting phosphorescence at room temperature has been active. (See, for example, Non-Patent Document 2 and Patent Document 4).
- the upper limit of the internal quantum efficiency is 100. / o, the emission efficiency is S4 times higher than that of singlet excitation, and the performance is almost the same as a cold cathode fluorescent lamp.
- Non-Patent Document 3 many compounds have been studied for synthesis centering on iridium complex-based heavy metal complexes (for example, see Non-Patent Document 3).
- L Ir (acac) such as (ppy) Ir (acac) (for example, a non-patent document)
- Non-Patent Document 5 A review (for example, see Non-Patent Document 5) has been conducted.
- Non-Patent Document 6 a compound having a hole transporting property is used as a host of a phosphorescent compound (for example, see Non-Patent Document 6).
- Patent Document 1 Patent No. 3093796
- Patent Document 2 JP-A-63-264692
- Patent Document 3 JP-A-3-255190
- Patent Document 4 U.S. Patent No. 6,097,147
- Patent Document 5 JP-A-2003-234192
- Non-Patent Document 1 M.A. Baldo et al., Nature, vol. 395, 151-154 (1998)
- Non-Patent Document 2 M. A. Baldo et al., Nature, vol. 403, No. 17, 750-753 (2000 years)
- Non-Patent Document 3 S. Lamansky et al., J. Am. Chem. Soc., Vol. 123, pp. 4304 (2001)
- Non-patent document 4 ME Tompson et al., The 10th International Workshop Inorganic and Organic Electroluminescence (EL'00, Hamamatsu)
- Non-patent document 5 Moon—Jae Youn.0g, Tetsuo Tsutsuiet al., The 10th International Workshop on Inorganic and Organic Electroluminescence (EL'00, Hamamatsu)
- Non-Noon Document 6 Ikai et al., The 10th International Workshop on Inorganic and Organic Electroluminescence (EL'00, Hamamatsu)
- the present invention has been made in view of the above-mentioned problems, and an object of the present invention is to provide a material for an organic EL device having high luminous efficiency, an organic EL device using the material for an organic EL device, and a lighting device. And a display device. Another object of the present invention is to provide a material for an organic EL device having a long life, an organic EL device using the material for an organic EL device, a lighting device, and a display device.
- a material for an organic electroluminescent device represented by the following general formula (1).
- a A ⁇ each independently represents an aromatic carbocyclic group or a heterocyclic group
- C3 each independently represents a residue necessary for forming an aromatic carbocyclic or heterocyclic ring.
- a display device comprising the organic electorescence luminescent element according to (4), wherein the organic electroluminescent device according to (4) is provided.
- An illuminating device comprising the organic electorophore luminescent element according to the item (4) of item (4).
- a display device comprising: the lighting device according to (11); and a liquid crystal element as display means.
- FIG. 1 shows an active matrix type full-color display device.
- FIG. 2 is a schematic view of a display section A of a full-color display device.
- FIG. 3 shows a schematic diagram of a pixel.
- FIG. 4 is a schematic diagram of a display device using a passive matrix method.
- FIG. 5 is a schematic diagram of a lighting device.
- FIG. 6 is a cross-sectional view of a lighting device.
- the boron compound represented by the general formula (1) is used as a host conjugate or a hole blocking material in an organic EL device material.
- A, A, and A each independently represent an aromatic carbocyclic group or a heterocyclic group
- Examples of the aromatic carbocyclic group represented by 1, A include a benzene ring, naphtha 2, A
- heterocyclic group represented by A, A, A examples include a carbazole ring, a pyridine ring,
- a group derived from a phenolic ring, a pyridine ring, a pyrimidine ring, a triazole ring, or an oxaziazole ring is more preferable, and a group derived from a phenolic ring or a pyridine ring is more preferable. It is.
- Cl, C2 and C3 each independently represent a residue necessary to form an aromatic carbocyclic or heterocyclic ring, and an aromatic group formed by Cl, C2 and C3.
- the carbon ring include a benzene ring, a naphthalene ring, an anthracene ring, an azulene ring, a phenanthrene ring, a triphenylene ring, a pyrene ring, a thalicene ring, a naphthacene ring, a perylene ring, a pentacene ring, and a hexanecene ring. May have a substituent.
- preferred are a benzene ring, a naphthalene ring and a phenanthrene ring, and more preferred are a benzene ring and a naphthalene ring.
- heterocyclic ring formed by Cl, C2 and C3 examples include a carbazole ring, a pyridine ring, a pyrimidine ring, a thiophene ring, a furan ring, an imidazole ring, a pyrazole ring, a triazole ring, an oxazole ring, a thiazole ring, Examples include an isooxazole, an isothiazole ring, an indole ring, a phenanthroline ring, a quinoline ring, an isoquinoline ring, and an oxadiazole ring, which may have a substituent.
- preferred are rubazole ring, pyridine ring, pyrimidine ring and phosphorus ring of phenanthate, and more preferred are rubazole ring, pyridine ring and pyrimidine ring.
- Examples of the material for an organic EL device of the present invention are shown below, but the present invention is not limited thereto.
- the light emitting layer according to the present invention contains a phosphorescent compound, and is a layer that emits light by recombination of electrons and holes injected from an electrode or an electron transport layer and a hole transport layer, and the light emitting portion is It may be inside the light emitting layer or at the interface between the light emitting layer and the adjacent layer.
- the light emitting layer according to the present invention preferably contains the compound represented by the general formula (1) as a host compound (light emitting host).
- the principle of light emission of the phosphorescent compound is two types. One is that the recombination of carriers occurs on the host conjugate where the carriers are transported, and the excited state of the host conjugate is generated. This Energy is transferred from the phosphorescent compound by transferring the energy of the phosphorescent compound to the phosphorescent compound. The other is that the phosphorescent compound acts as a carrier trap, and the recombination of carriers on the phosphorescent compound occurs. It is a carrier trap type in which light emission from the phosphorescent compound is obtained, and in each case, the energy of the excited state of the phosphorescent compound is lower than the energy of the excited state of the host compound. It is.
- the maximum phosphorescent emission wavelength of the phosphorescent compound is not particularly limited, and in principle, a central metal, a ligand, a substituent of the ligand, and the like are selected. Thus, the emission wavelength obtained can be changed, but it is preferable that the phosphorescence emission wavelength of the phosphorescent compound has a maximum wavelength of phosphorescence at 380 nm to 480 nm.
- Organic EL devices that emit blue light and organic EL devices that emit white light are examples of devices having such a phosphorescence emission wavelength. However, these devices can further reduce the emission voltage and consume less power. Can be operated with
- the light emitting layer may contain a phos-H-conjugated compound in addition to the phosphorescent compound.
- the compound represented by the general formula (1) may be used as a host conjugate, and a plurality of known host conjugates may be used in combination.
- a plurality of types of host compounds it is possible to adjust the transfer of electric charges, and it is possible to increase the efficiency of the organic EL device.
- these known host compounds compounds which have a hole transporting ability and an electron transporting ability, prevent a longer wavelength of light emission, and have a high Tg (glass transition temperature) are preferable.
- the light emitting layer may further contain a host compound having a maximum fluorescence wavelength as the host compound.
- a host compound having a fluorescence maximum wavelength is one having a high fluorescence quantum yield in a solution state.
- the fluorescence quantum yield is preferably at least 10%, particularly preferably at least 30%.
- the host compound having the maximum fluorescence wavelength include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squarium dyes, oxobenzantracene dyes, fluorescein dyes, rhodamine dyes, and pyrylium dyes. Dyes, perylene dyes, stilbene dyes, polythiophene dyes, and the like. The fluorescence quantum yield can be measured by the method described in Spectroscopy II, p. 362 (1992 edition, Maruzen) of the 4th edition of Experimental Chemistry Lecture 7.
- the light emitting layer can be formed by forming the above compound by a known thin film forming method such as a vacuum evaporation method, a spin coating method, a casting method, an LB method, and an ink jet method.
- the thickness of the light emitting layer is not particularly limited, but is usually selected from 5 nm and 5 zm, preferably from 5 nm to 200 nm.
- the light-emitting layer may have a single-layer structure composed of one or more of these phosphorescent compounds and host conjugates, or a laminated structure composed of a plurality of layers having the same composition or different compositions. May be.
- the light emitting layer according to the present invention preferably contains a dopant, and further preferably contains a phosphorescent dopant as a dopant. As a result, higher luminous efficiency can be obtained.
- a dopant also referred to as a luminescent dopant that can be used in combination with the hostile conjugate of the present invention will be described.
- the dopants are roughly classified into two types, a fluorescent dopant that emits fluorescence and a phosphorescent dopant that emits phosphorescence.
- fluorescent dopant examples include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squarium dyes, oxobenzanthracene dyes, fluorescein dyes, and rhodamine dyes And a pyrylium-based dye, a perylene-based dye, a styrven-based dye, a polythiophene-based dye, a rare-earth complex-based phosphor, and other known fluorescent compounds.
- the phosphorescent dopant contained in the light emitting layer according to the present invention can be appropriately selected and used as a known medium used in the light emitting layer of the organic EL device.
- a known medium used in the light emitting layer of the organic EL device for example, an iridium complex described in Japanese Patent Application Laid-Open No. 2001-247859, or a formula such as that described in WO 00 / 70,655 pamphlet, pp. 16-18, for example, tris (2-pheninolehi).
- Platinum complexes such as lysine) iridium and the like, osmium complexes, and certain complexes such as 2,3,7,8,12,13,1 7,18-otataethyl-21H, 23 ⁇ -porphyrin platinum complexes are also examples of dopant.
- a phosphorescent compound as a dopant, a light emitting organic EL device having high internal quantum efficiency can be realized.
- the phosphorescent compound used in the present invention is preferably a complex compound containing one or more metals belonging to groups 8, 9, and 10 of the periodic table, More preferred are iridium compounds, osmium compounds, platinum compounds (platinum complex-based compounds), and rare earth complexes, and most preferred are iridium compounds.
- the phosphorescent compound according to the present invention has a phosphorescence quantum yield in a solution of preferably 0.001 or more at 25 ° C, more preferably 0.01 or more, and particularly preferably 0.01 or more. 0.1 or more.
- the phosphorescence quantum yield can be measured by the method described in Spectroscopy II, 4th edition, Spectroscopy II, p. 398 (1992 edition, Maruzen).
- Blocking Layer Hole Blocking Layer, Electron Blocking Layer
- the hole blocking layer is, in a broad sense, an electron transporting layer, and is made of a material having a function of transporting electrons and having a very small ability to transport holes. And the recombination probability of holes can be improved.
- the hole blocking layer functions to prevent holes moving from the hole transport layer from reaching the cathode, and to efficiently transport electrons injected from the cathode toward the light emitting layer. It is formed by a possible compound.
- the physical properties required of the material constituting the hole blocking layer are that the electron mobility is high and the hole mobility is low, and that the hole ionization potential of the light emitting layer is higher than that of the material. It is preferable to have a force having a large value of the ionization potential and a band gap larger than the band gap of the light emitting layer.
- the compound represented by the general formula (1) of the present invention is preferable to use as a hole blocking material.
- a hole blocking material at least one of a styryl compound, a triazole derivative, a phenolic phosphorus derivative, an oxadiazole derivative, and a boron derivative is also effective for obtaining the effects of the present invention.
- the electron blocking layer is a hole transport layer in a broad sense, and has a function of transporting holes. It is made of a material that has an extremely small ability to transport electrons while transporting holes. By blocking electrons while transporting holes, the recombination probability of electrons and holes can be improved.
- the hole blocking layer and the electron blocking layer are formed by thinning the above-mentioned material by a known method such as a vacuum deposition method, a spin coating method, a casting method, an ink jet method, and an LB method. That power S can.
- the hole transporting material has any of hole injection or transport and electron barrier properties, and may be any of an organic substance and an inorganic substance.
- triazole derivatives for example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styryl anthracene derivatives, fluorenone derivatives,
- Conventionally known materials such as hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline-based copolymers, and conductive polymer oligomers, particularly thiophene oligomers, may be used.
- the hole transporting material As the hole transporting material, the above-mentioned materials can be used. It is preferable to use a porphyrin compound, an aromatic tertiary amine compound and a styrylamine compound, particularly an aromatic tertiary amine compound. .
- aromatic tertiary amine compound and styrylamine compound include N, N, N ', N'-tetraphenyl-4, ⁇ '-diaminophenyl; ⁇ , N'-diphenyl ⁇ , N '-Bis (3-methylpheninole) -1- [1,1'-bipheninole] -1,4,1-diamine (TPD); 2,2-bis (4-di- ⁇ -tolylaminophenyl) propane; 1 , 1-bis (4-di ⁇ -tolylaminophenyl) cyclohexane; ⁇ , ⁇ , ⁇ ', N'-tetra- ⁇ -tolyl 4, 4'-diaminobiphenyl; 1,1-bis (4- Di- ⁇ -tolylaminophenyl) -4-phenylcyclohexane; bis (4-dimethylamino-2-methylphenyl) phenylmethane; bis
- a polymer material in which these materials are introduced into a polymer chain, or in which these materials are used as a polymer main chain can also be used.
- inorganic compounds such as p-type-Si and p-type-SiC can also be used as the hole injection material and the hole transport material.
- the hole transport layer is formed by thinning the above-described hole transport material by a known method such as a vacuum evaporation method, a spin coating method, a casting method, a printing method including an inkjet method, and an LB method. Can be formed.
- the thickness of the hole transport layer is not particularly limited, but is usually! ! ! -! ! ! Degree, preferably 5 nm to 200 nm.
- the hole transport layer may have a single-layer structure composed of one or more of the above materials.
- the material of the electron transporting layer according to the present invention is not particularly limited as long as it has a function of transmitting electrons injected from the cathode to the light emitting layer. Can be.
- electron transporting material examples include a heterocyclic tetracyclic compound such as a nitro-substituted fluorene derivative, a diphenylquinone derivative, a thiopyrandioxide derivative, and a naphthalene perylene.
- heterocyclic tetracyclic compound such as a nitro-substituted fluorene derivative, a diphenylquinone derivative, a thiopyrandioxide derivative, and a naphthalene perylene.
- examples thereof include carboxylic acid anhydrides, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, and oxadiazole derivatives.
- a thiadiazole derivative in which an oxygen atom of the oxaziazono ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron-withdrawing group can also be used as the electron transport material.
- a polymer material in which these materials are introduced into a polymer chain, or in which these materials are used as a polymer main chain can also be used.
- a metal complex of an 8_quinolinol derivative for example, tris (8-quinolinol) aluminum (Alq3), tris (5,7-dichroic-8_quinolinol) aluminum, tris (5,7-dib Mouth Mo-8-quinolinol) aluminum, tris (2-methyl-8-quinolinol) aluminum, tris (5-methyl_8_quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), and other metal complexes Metal complexes in which the central metal is replaced by In, Mg, Cu, Ca, Sn, Ga or Pb can also be used as an electron transport material.
- metal-free or metal phthalocyanine and those whose terminals are substituted with an alkyl group / sulfonic acid group or the like, can also be preferably used as the electron transporting material.
- the distyryl virazine derivative exemplified as a material for the light emitting layer can also be used as an electron transporting material, and like the hole injection layer and the hole transport layer, n-type Si, n-type SiC, etc. Can also be used as an electron transport material.
- the electron transport layer can be formed by forming a film of the above compound by a known thin film forming method such as a vacuum evaporation method, a spin coating method, a casting method, and an LB method.
- a known thin film forming method such as a vacuum evaporation method, a spin coating method, a casting method, and an LB method.
- the electron transporting layer can be formed by thinning the electron transporting material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an inkjet method, and an LB method. it can.
- the thickness of the electron transport layer is not particularly limited, but is usually! ! ! -! ! ! Degree, preferably 5 nm to 200 nm.
- the electron transport layer may have a single-layer structure composed of one or more of the above materials.
- anode in the organic EL device a metal, an alloy, an electrically conductive compound, or a mixture thereof having a large work function (4 eV or more) as an electrode material is preferably used.
- electrode materials include metals such as Au, and conductive transparent materials such as Cul, indium tin oxide (ITO), SnO, and Zn ⁇ . Also, IDIXO (In O _Zn ⁇ ) etc.
- a material that is amorphous and can form a transparent conductive film may be used.
- the anode is formed by depositing these electrode materials into a thin film by vapor deposition, sputtering, or the like, and then using a photolithography method to form a pattern of the desired shape. (Approximately 100 ⁇ m or more). The pattern may be formed via a mask. When light emission is extracted from this anode, it is desirable that the transmittance be greater than 10%. Further, the sheet resistance of the anode is preferably several hundreds ⁇ / port or less. Further, the film thickness is selected in the range of usually 10 nm to 1000 nm, preferably 10 nm to 200 nm, depending on the material.
- a cathode a metal having a small work function (4 eV or less) (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof are used as an electrode material.
- electrode materials include sodium, sodium-potassium alloys, magnesium, lithium, magnesium / copper mixtures, magnesium / silver mixtures, magnesium / aluminum mixtures, magnesium Z indium mixtures, aluminum Z aluminum oxide (Al O) mixture, indium, lithium
- a 23Z aluminum mixture, a rare earth metal and the like can be mentioned.
- a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function value, such as a magnesium / silver mixture, magnesium / Aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3) mixture, lithium / a
- Luminum mixtures, aluminum and the like are preferred.
- the cathode can be manufactured by forming a thin film from these electrode substances by a method such as evaporation or sputtering.
- the sheet resistance as the cathode is preferably several hundreds ⁇ / port or less.
- the film thickness is usually selected in the range of lOnm-5 ⁇ , preferably 50-200 nm. Note that if one of the anode and the cathode of the organic EL element is transparent or translucent in order to transmit the emitted light, the emission luminance is advantageously improved.
- a transparent or translucent cathode can be produced by producing the above metal on the cathode with a thickness of lnm 20nm and then producing the conductive transparent material mentioned in the description of the anode thereon. By applying this, it is possible to produce a device in which both the anode and the cathode have transparency.
- Buffer Layer Anode Buffer Layer, Cathode Buffer Layer
- the injection layer is provided as necessary, and includes a cathode buffer layer (electron injection layer) and an anode buffer layer (hole injection layer). As described above, between the anode and the light emitting layer or the hole transport layer, and between the cathode and the cathode. It may be present between the light layer or the electron transport layer.
- a cathode buffer layer electron injection layer
- an anode buffer layer hole injection layer
- the buffer layer is a layer provided between an electrode and an organic layer in order to lower the driving voltage and improve the light emission luminance, and is referred to as "the organic EL element and the forefront of its industrialization (Nov. This is described in detail in Chapter 2, Chapter 2, “Electrode Materials” (page 123, 166) of Volume 2 of “TS Inc.”, and includes an anode buffer layer and a cathode buffer layer.
- anode buffer layer hole injection layer
- Phthalocyanine buffer layer represented by copper phthalocyanine oxide buffer layer represented by vanadium oxide
- amorphous carbon buffer layer polymer buffer layer using conductive polymers such as polyaniline (emeraldine) and polythiophene, etc. Is mentioned.
- cathode buffer layer (electron injection layer) The details of the cathode buffer layer (electron injection layer) are also described in JP-A-6-325871, JP-A-9-17574, JP-A-10-74586 and the like.
- strontium Buffer layer such as aluminum and aluminum
- alkaline metal compound buffer layer such as lithium fluoride
- alkaline earth metal compound buffer layer such as magnesium fluoride
- oxide buffer layer such as aluminum oxide And the like.
- the buffer layer (injection layer) is preferably a very thin film, depending on the material to be used.
- the film thickness is preferably in the range of 0.1 nm to 5 ⁇ m.
- Substrate also referred to as substrate, substrate, support, etc.
- the organic EL device of the present invention is preferably formed on a substrate.
- the substrate of the organic EL device of the present invention is not particularly limited in the type of glass, plastic, etc., and is not particularly limited as long as it is transparent. Glass, quartz, and a light-transmitting resin film can be used. A particularly preferred substrate is a resin film that can provide flexibility to the organic EL device.
- Examples of the resin film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyether sulfone (PES), polyether imide, polyether ether ketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC), Examples of the film include cellulose triacetate (TAC), cellulose acetate propionate (CAP), and the like.
- PET polyethylene terephthalate
- PEN polyethylene naphthalate
- PES polyether sulfone
- PES polyether imide
- polyether ether ketone polyphenylene sulfide
- PC polycarbonate
- Examples of the film include cellulose triacetate (TAC), cellulose acetate propionate (CAP), and the like.
- TAC cellulose triacetate
- CAP cellulose acetate propionate
- an inorganic substance or An organic coating or a hybrid coating of both may be formed on the surface of the resin film.
- the organic light-emitting device of the present invention has an external extraction quantum efficiency of light emission at room temperature of preferably 1% or more, more preferably 5% or more.
- the external extraction quantum efficiency (%) the number of photons emitted to the outside of the organic EL element / the number of electrons flowing to the organic EL element X I 00.
- a hue improving filter such as a color filter or the like may be used in combination, or a color conversion filter that converts a color emitted from the organic EL element into multiple colors using a phosphor may be used in combination.
- the emission maximum of the organic EL device is preferably 480 nm or less.
- a method for producing an organic EL device of the present invention comprising an anode Z, an anode buffer layer Z, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, a cathode buffer layer, and a cathode. Will be described.
- a thin film made of a desired electrode material for example, an anode material ITO
- a suitable substrate by a method such as evaporation or sputtering so as to have a thickness of 1 / im or less, preferably 10 nm to 200 nm.
- an organic compound thin film of an organic EL device material such as an anode buffer layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, and a cathode buffer layer is formed thereon.
- the vapor deposition conditions vary depending on the type of compound used, etc., but generally, the boat heating temperature is 50 ° C to 450 ° C, the degree of vacuum is 10 to 6 Pa 10 to 2 Pa, It is desirable to appropriately select a vapor deposition rate in the range of 0 to 50 nm / sec, substrate temperature of -50 ° C to 300 ° C, and film thickness of 0.1 to 5 nm, preferably 5 to 200 nm.
- a cathode material for example, a thin film made of A1 is formed thereon to a thickness of 1 ⁇ m or less, preferably 50 to 200 nm, for example, by vapor deposition or sputtering.
- a desired organic EL device can be obtained by forming the cathode by the method and providing the cathode. In the production of this organic EL device, it is preferable that the hole injection layer to the cathode be produced consistently by a single evacuation, but it is still powerful even if it is taken out and subjected to a different film forming method. At that time, it is necessary to consider that the work is performed in a dry inert gas atmosphere.
- a shadow mask is provided only when a light emitting layer is formed, and since other layers are common, a pattern mask such as a shadow mask is unnecessary.
- the film can be formed by a spin coating method, an ink jet method, a printing method, or the like.
- the method is not particularly limited, but is preferably an evaporation method, an inkjet method, or a printing method.
- a vapor deposition method a shadow mask is used, and Patterjung is preferred.
- the production order can be reversed, and the cathode, the cathode buffer layer, the electron transport layer, the hole transport layer, the light emitting layer, the hole transport layer, the anode buffer layer, and the anode can be produced in this order.
- a DC voltage is applied to the multicolor display device obtained in this manner, light emission can be observed by applying a voltage of about 2 to 40 V with the anode being + and the cathode being of one polarity.
- an AC voltage may be applied.
- the alternating current waveform to be applied may be arbitrary.
- the display device of the present invention can be used as a display device, a display, and various light-emitting light sources.
- full-color display is possible by using three types of organic EL elements emitting blue, red and green light.
- Examples of the display device and display include a television, a personal computer, a mopile device, an AV device, a character broadcast display, and information display in a car.
- the driving method may be either a simple matrix (passive matrix) method or an active matrix method.
- the lighting device of the present invention can be used for home lighting, vehicle interior lighting, backlights for clocks and liquid crystals, billboard advertisements, traffic lights, light sources for optical storage media, light sources for electrophotographic copiers, light sources for optical communication processors, Examples include a light source of an optical sensor, but the present invention is not limited to this.
- the organic EL device according to the present invention may be used as an organic EL device having a resonator structure.
- the intended use of the organic EL device having such a resonator structure is, for example, 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. Power is not limited to these. Further, laser oscillation may be used for the above purpose.
- the organic EL element of the present invention may be used as a kind of lamp for illumination or an exposure light source, a projection device of a type for projecting an image, or of a type for directly viewing a still image or a moving image. It may be used as a display device (display).
- the driving method may be either a simple matrix (passive matrix) method or an active matrix method.
- a full-color display device can be manufactured by using three or more kinds of the organic EL elements of the present invention having different emission colors.
- a force S that can convert the emission color of the organic EL to another color by using a color conversion filter to obtain a full color, in which case the ⁇ max of the organic EL emission is preferably 480 nm or less.
- FIG. 1 is a schematic diagram showing an example of a display device including an organic EL element.
- FIG. 2 is a schematic view of a display such as a mobile phone for displaying image information by light emission of an organic EL element.
- the display 1 includes a display unit A having a plurality of pixels, a control unit B that performs image scanning of the display unit A based on image information, and the like.
- the control unit B is electrically connected to the display unit A, sends a scan signal and an image data signal to each of a plurality of pixels based on image information from the outside, and uses the scan signal to control pixels for each scan line. , Sequentially emit light according to the image data signal, perform image scanning, and display image information on the display unit A.
- FIG. 2 is a schematic diagram of the display unit A.
- the display section A includes a wiring section including a plurality of scanning lines 5 and data lines 6, and a plurality of images on a substrate. Element 3 and so on.
- the main members of the display unit A will be described below.
- FIG. 2 shows a case where the light emitted from the pixel 3 is extracted in the white arrow direction (downward).
- the scanning lines 5 and the plurality of data lines 6 of the wiring portion are each made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a grid and connected to the pixels 3 at orthogonal positions. (Details not shown).
- the pixel 3 When the scan signal is applied from the scanning line 5, the pixel 3 receives the image data signal from the data line 6, and emits light in accordance with the received image data. By properly arranging pixels in the red, green, and blue light emission regions on the same substrate, full color display is possible.
- FIG. 3 shows a schematic diagram of a pixel.
- the pixel includes an organic EL element 10, a switching transistor 11, a driving transistor 12, a capacitor 13, and the like.
- a full-color display can be performed by using red, green, and blue light emitting organic EL elements as the organic EL elements 10 for a plurality of pixels and juxtaposing them on the same substrate.
- an image data signal is applied from the control unit B to the drain of the switching transistor 11 via the data line 6.
- a scanning signal is applied from the control unit B to the gate of the switching transistor 11 via the scanning line 5
- the driving of the switching transistor 11 is turned on, and the image data signal applied to the drain is transferred to the capacitor 13 and the driving transistor. It is transmitted to the gate of star 12.
- the capacitor 13 is charged according to the potential of the image data signal, and the driving of the drive transistor 12 is turned on.
- the drive transistor 12 has a drain connected to the power supply line 7, a source connected to the electrode of the organic EL element 10, and an organic EL element connected from the power supply line 7 according to the potential of the image data signal applied to the gate. Element 10 is supplied with current.
- the driving of the switching transistor 11 is turned off. Even if the driving of the switching transistor 11 is turned off, the capacitor 13 holds the potential of the charged image data signal. Is kept on, and the organic EL element 10 continues to emit light until the next scanning signal is applied.
- the driving transistor 12 is driven according to the potential of the next image data signal synchronized with the scanning signal, and the organic EL element 10 emits light.
- the organic EL element 10 emits light by providing a switching transistor 11 and a driving transistor 12 as active elements to the organic EL element 10 of each of the plurality of pixels, and The element 10 emits light.
- a light emitting method is called an active matrix method.
- the light emission of the organic EL element 10 may be light emission of a plurality of gradations by a multi-valued image data signal having a plurality of gradation potentials, or light emission of a predetermined light emission amount by a binary image data signal. It may be on or off.
- the potential of the capacitor 13 may be maintained until the next scan signal is applied, or may be discharged immediately before the next scan signal is applied. .
- the present invention is not limited to the active matrix method described above, but may be a passive matrix light emission drive in which an organic EL element emits light in accordance with a data signal only when a scanning signal is scanned.
- FIG. 4 is a schematic diagram of a display device using a passive matrix system.
- a plurality of scanning lines 5 and a plurality of image data lines 6 are provided in a lattice shape so as to face each other with the pixel 3 interposed therebetween.
- the pixels 3 connected to the applied scanning line 5 emit light according to the image data signal.
- the manufacturing cost can be reduced because the active elements are connected to the pixels 3.
- An IT ⁇ indium tin oxide
- a 100 mm X 100 mm X 1.1 mm glass substrate as an anode.
- (Oxide) was patterned on a substrate (NA45, manufactured by NH Techno Glass Co., Ltd.) on which a transparent support substrate provided with the ITO transparent electrodes was ultrasonically washed with isopropyl alcohol and dried with dry nitrogen gas. UV ozone cleaning was performed for 5 minutes.
- This transparent support substrate was fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while 200 mg of Hi-NPD was placed in a molybdenum resistance heating boat, and Compound 1 was used as a host compound in another molybdenum resistance heating boat.
- the heating boat containing BCP is energized and heated, and is deposited on the light emitting layer at a deposition rate of 0.1 nm / sec to form a 10 nm-thick electron transport layer also serving as a hole blocking layer. Provided. On top of that, the heating boat containing Alq was further energized and heated,
- An electron injection layer having a thickness of 40 nm was further provided by vapor deposition on the electron transport layer at a deposition rate of 0.1 nm / sec.
- the substrate temperature at the time of vapor deposition was room temperature.
- the organic EL device 1 was prepared in the same manner as in the organic EL device 1 except that the exemplified compound 1 used as the host conjugate in the light emitting layer was replaced with the compound shown in Table 1 to obtain the host conjugate.
- 1 2 1 1 1 15 was prepared in the same manner as 1 1. The structure of each compound used above is shown below. [0134] [Formula 10]
- the quantum efficiency (%) taken out of the fabricated organic EL device was measured at a constant current of 2.5 mA / cm 2 at 23 ° C. in a dry nitrogen gas atmosphere.
- a spectral radiance meter CS-1000 manufactured by Koniki Minolta was used.
- the measurement results of the external takeout quantum efficiency in Table 1 were expressed as relative values when the measured value of the organic EL element 1-15 was set to 100.
- the IT ⁇ transparent electrode After patterning a 100 mm X 100 mm X 1.1 mm glass substrate on a 100 mm x 100 mm x 1.1 mm glass substrate with ITOO (indium tin oxide) formed by lOOnm (NH45, NA Technoglass Co., Ltd. NA45), the IT ⁇ transparent electrode
- ITOO indium tin oxide
- the transparent support substrate provided with was cleaned by ultrasonic cleaning with isopropyl alcohol, dried by dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
- This transparent support substrate was fixed to the substrate holder of a commercially available vacuum evaporation system, while 200 mg of ⁇ -NPD was placed in a molybdenum resistance heating boat, and 200 mg of CBP was placed in another molybdenum resistance heating boat.
- a molybdenum resistance heating boat was charged with 200 mg of Compound 1 as a hole-blocking material, another molybdenum resistance heating boat was charged with 100 mg of Ir-1, and another molybdenum resistance heating boat was charged with 200 mg of Alq. Attached to.
- the heating boat containing Compound 1 is energized and heated, and is deposited on the light emitting layer at a deposition rate of 0.1 nm / sec. Layers were provided. On top of that, the heating boat containing Alq was further energized and heated to deposit
- An electron injection layer having a thickness of 40 nm was further formed by vapor deposition on the electron transport layer at a speed of InmZsec.
- the substrate temperature at the time of vapor deposition was room temperature.
- Example 2 In the same manner as in Example 1, the external extraction quantum efficiency of the organic EL element 2-1-11-2 was evaluated. Further, the life was evaluated according to the following measurement method.
- the phosphorescent compounds of the organic EL device 1-1 of the present invention prepared in Example 1, the organic EL device 2_7 of the present invention prepared in Example 2, and the organic EL device 2_7 of the present invention were represented by the following Btp Ir ( acac
- FIG. 2 shows only a schematic diagram of the display section A of the manufactured full-color display device. That is, on the same substrate, a wiring section including a plurality of scanning lines 5 and data lines 6 and a plurality of juxtaposed pixels 3 (pixels in a red region, pixels in a green region, pixels in a blue region, and the like) are arranged side by side.
- the scanning line 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material, and the scanning line 5 and the data line 6 are orthogonal to each other in a grid and are connected to the pixel 3 at orthogonal positions ( Details are not shown).
- the plurality of images Element 3 is driven by an active matrix method including an organic EL element corresponding to each emission color, a switching transistor as an active element, and a driving transistor, and a scanning signal is applied from a scanning line 5.
- An organic EL element 111W was produced in the same manner as the organic EL element 111 except that the light emitting layer was provided so as to have a thickness of 30 nm by adjusting the thickness to be 0: 5: 0.6.
- the non-light-emitting surface of the obtained organic EL element 111W was covered with a glass case to obtain a lighting device shown in FIGS.
- the illuminator was able to be used as a thin illuminator that emits white light with high luminous efficiency and long luminous life.
- FIG. 5 is a schematic diagram of the lighting device
- FIG. 6 is a cross-sectional view of the lighting device.
- the organic EL element 100 is covered with a glass cover 102, the glass substrate 101 with a transparent electrode and the glass cover 102 are sealed with a sealing agent 107, and a power line (anode) 103 and a power line (cathode) 104 are formed. It is connected. 105 is a cathode and 106 is an organic EL layer.
- the glass cover 102 is filled with a nitrogen gas 108 and a water replenisher 109 is provided.
- a material for an organic EL device having high luminous efficiency and a material for the organic EL device are used.
- an organic EL device, a lighting device, and a display device can be provided. Further, it was possible to provide a material for an organic EL device having a long life, an organic EL device using the material for an organic EL device, a lighting device, and a display device.
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Abstract
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KR102050145B1 (ko) * | 2014-07-31 | 2019-11-28 | 코니카 미놀타 가부시키가이샤 | 유기 일렉트로루미네센스 소자, 표시 장치, 조명 장치, π공액계 화합물, 발광성 박막 |
EP3147958A1 (en) * | 2015-09-28 | 2017-03-29 | Novaled GmbH | Organic electroluminescent devices comprising borane compounds |
JP2018534768A (ja) * | 2015-09-28 | 2018-11-22 | ノヴァレッド ゲーエムベーハー | 有機elデバイス |
WO2017055263A1 (en) | 2015-09-28 | 2017-04-06 | Novaled Gmbh | Organic electroluminescent devices comprising borane compounds |
KR20180132129A (ko) | 2016-05-13 | 2018-12-11 | 코니카 미놀타 가부시키가이샤 | 유기 일렉트로루미네센스 소자용 재료, 유기 일렉트로루미네센스 소자, 표시 장치 및 조명 장치 |
US11437590B2 (en) | 2016-05-13 | 2022-09-06 | Konica Minolta, Inc. | Organic electroluminescence element material, organic electroluminescence element, display apparatus and illumination apparatus |
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JPWO2005062675A1 (ja) | 2007-12-13 |
JP4600287B2 (ja) | 2010-12-15 |
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