JP2008135498A - Light emitting element - Google Patents

Light emitting element Download PDF

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JP2008135498A
JP2008135498A JP2006319658A JP2006319658A JP2008135498A JP 2008135498 A JP2008135498 A JP 2008135498A JP 2006319658 A JP2006319658 A JP 2006319658A JP 2006319658 A JP2006319658 A JP 2006319658A JP 2008135498 A JP2008135498 A JP 2008135498A
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light
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light emitting
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Takeshi Ikeda
Takeshi Ishigaki
Takeshi Tominaga
剛 富永
武史 池田
剛 石垣
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Toray Ind Inc
東レ株式会社
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Abstract

A light-emitting element with high luminous efficiency and low driving voltage is provided.
A light emitting layer composed of a host material and a dopant material exists between an anode and a cathode, and emits light by electric energy. The host material has a carbazole skeleton represented by the general formula (1). A light-emitting element which is a compound and whose dopant material is a triplet light-emitting material.

[Selection figure] None

Description

  The present invention is an element that can convert electrical energy into light, and can be used in the fields of display elements, flat panel displays, backlights, lighting, interiors, signs, signboards, electrophotographic machines, optical signal generators, and the like. It relates to an element.

  In recent years, research on organic thin-film light-emitting devices that emit light when electrons injected from a cathode and holes injected from an anode are recombined in an organic light-emitting body sandwiched between both electrodes has been actively conducted. This light-emitting element is characterized by thin light emission with high luminance under a low driving voltage and multicolor light emission by selecting a light-emitting material.

This study was conducted by C.D. W. Since Tang et al. Have shown that organic thin-film light-emitting elements emit light with high brightness, many research institutions have studied. The representative structure of the organic thin film light emitting device presented by the Kodak research group is a hole transporting diamine compound on an ITO glass substrate, tris (8-quinolinolato) aluminum (III) as a light emitting layer, and a cathode. Mg: Ag was sequentially provided, and green light emission of 1,000 cd / m 2 was possible with a driving voltage of about 10 V (see Non-Patent Document 1).

  In addition, organic thin-film light-emitting elements can be obtained in various light-emitting colors by using various light-emitting materials for the light-emitting layer. In particular, research on light emitting materials of the three primary colors of red, green, and blue is the most active, and intensive research has been conducted with the aim of improving characteristics.

  One of the biggest problems in organic thin-film light-emitting elements is the compatibility between high luminous efficiency and low driving voltage. As a means for obtaining a highly efficient light-emitting element, a method of forming a light-emitting layer by doping a host material with a dopant material of several percent is known (see Patent Document 1). The host material is required to have high carrier mobility and uniform film formability, and the dopant material is required to have high fluorescence quantum yield and uniform dispersibility.

  In addition, as a dopant material, a fluorescent (singlet light emission) material is generally used in the past, but a phosphorescent (triplet light emission) material has been used in order to improve the light emission efficiency. Attempts have been made and a group at Princeton University has shown that the luminous efficiency is significantly higher than conventional fluorescent materials (see Non-Patent Document 2). As a phosphorescent dopant material, a technique using a metal complex having iridium, osmium, rhodium, palladium, platinum or the like as a central metal is disclosed (see Patent Documents 2 to 4). Moreover, as a host material combined with a phosphorescent dopant material, a technique using a carbazole derivative, an aromatic amine derivative, a quinolinol metal complex, or the like has been disclosed (see Patent Documents 2 to 6). None showed a low drive voltage.

In addition to the above, there are a large number of host materials and dopant materials that form a light emitting material, and the combination of these materials becomes enormous. In general, as a guideline for easy transfer of energy from the host material to the phosphorescent dopant material, the relationship between the triplet levels of the host material and the dopant material is known (see Patent Document 2). Not all light emission mechanisms have been elucidated, and there are many trial and error parts. That is, in order to obtain a light-emitting element having better light emission characteristics, it is important not only to discover a new host material and dopant material, but also to find an optimal combination of host material and dopant material.
Applied Physics Letters (USA), 1987, 51, 12, 913-915 Japanese Patent No. 2814435 Applied Physics Letters (USA), 1999, Vol. 75, No. 1, page 4. Special table 2003-526876 gazette Special table 2003-515897 gazette JP 2003-81988 A JP 2003-133075 A Japanese translation of PCT publication No. 2002-540572

  Accordingly, the present invention solves the problems of the prior art and provides a light emitting element with high luminous efficiency and low driving voltage.

  That is, the present invention is an element in which a light emitting layer composed of at least a host material and a dopant material exists between an anode and a cathode and emits light by electric energy, and the host material is a carbazole skeleton represented by the general formula (1). A light-emitting element characterized in that the dopant material is a triplet light-emitting material.

(R 1 to R 24 are each hydrogen, an alkyl group, a cycloalkyl group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl thioether group, an aryl group, an amino group, a silyl group, or an adjacent substituent. (It is selected from ring structures, provided that at least one of R 15 to R 24 is selected from an amino group and a ring structure with an adjacent substituent.)

  The light emitting device of the present invention has high luminous efficiency and can be driven with a low driving voltage.

  The light emitting device of the present invention comprises at least an anode and a cathode, and an organic layer made of a light emitting device material interposed between the anode and the cathode.

  The anode used in the present invention is not particularly limited as long as it can efficiently inject holes into the organic layer, but it is preferable to use a material having a relatively large work function. For example, tin oxide, indium oxide, zinc oxide Conductive metal oxides such as indium and indium tin oxide (ITO), metals such as gold, silver and chromium, inorganic conductive materials such as copper iodide and copper sulfide, conductive polymers such as polythiophene, polypyrrole and polyaniline, etc. Is mentioned. These electrode materials may be used alone, or a plurality of materials may be laminated or mixed.

  The resistance of the electrode is not limited as long as a current sufficient for light emission of the light-emitting element can be supplied. For example, an ITO substrate of 300Ω / □ or less functions as an element electrode, but since it is now possible to supply a substrate of about 10Ω / □, use a low-resistance product of 100Ω / □ or less. Is particularly desirable. The thickness of ITO can be arbitrarily selected according to the resistance value, but is usually used in a range of 100 to 300 nm.

In order to maintain the mechanical strength of the light emitting element, the light emitting element is preferably formed over a substrate. As the substrate, a glass substrate such as soda glass or non-alkali glass is preferably used. As the thickness of the glass substrate, it is sufficient that the thickness is sufficient to maintain the mechanical strength. The glass material is preferably alkali-free glass because it is better to have less ions eluted from the glass, but soda lime glass with a barrier coat such as SiO 2 is also available on the market. it can. Furthermore, if the anode functions stably, the substrate does not have to be glass. For example, the anode may be formed on a plastic substrate. The ITO film forming method is not particularly limited, such as an electron beam method, a sputtering method, and a chemical reaction method.

  The material used for the cathode used in the present invention is not particularly limited as long as it can efficiently inject electrons into the organic layer, but generally platinum, gold, silver, copper, iron, tin, zinc, aluminum, indium, Examples thereof include chromium, lithium, sodium, potassium, cesium, calcium, magnesium, and alloys thereof. Lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective for increasing the electron injection efficiency and improving device characteristics. However, these low work function metals are generally unstable in the atmosphere. For example, the organic layer is doped with a small amount of lithium or magnesium (1 nm or less in the vacuum vapor deposition thickness meter display) to be stable. A method using a high electrode can be cited as a preferred example. Also, an inorganic salt such as lithium fluoride can be used. Furthermore, for electrode protection, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys using these metals, and inorganic substances such as silica, titania and silicon nitride, polyvinyl alcohol, vinyl chloride Lamination of hydrocarbon polymer compounds and the like is a preferred example. The method for producing these electrodes is not particularly limited as long as conduction can be achieved, such as resistance heating, electron beam, sputtering, ion plating, and coating.

  The organic layer constituting the light emitting device of the present invention is composed of at least a light emitting layer made of a light emitting device material. As an example of the organic layer configuration, in addition to the configuration consisting of only the light emitting layer, 1) hole transport layer / light emitting layer / electron transport layer and 2) light emitting layer / electron transport layer, 3) hole transport layer / light emission A laminated structure such as a layer can be mentioned. Moreover, each said layer may consist of a single layer, respectively, and may consist of multiple layers. When the hole transport layer and the electron transport layer are composed of a plurality of layers, the layers in contact with the electrode may be referred to as the hole injection layer and the electron injection layer, respectively. In the material, the electron injection material is included in the electron transport material.

  The hole transport layer is formed by laminating and mixing one or more hole transport materials or a mixture of the hole transport material and the polymer binder. Examples of the hole transport material include 4,4′-bis (N- (3-methylphenyl) -N-phenylamino) biphenyl and 4,4′-bis (N- (1-naphthyl) -N-phenyl. Amino) biphenyl, triphenylamine derivatives such as 4,4 ′, 4 ″ -tris (3-methylphenyl (phenyl) amino) triphenylamine, bis (N-allylcarbazole) or bis (N-alkylcarbazole) Biscarbazole derivatives, pyrazoline derivatives, stilbene compounds, hydrazone compounds, benzofuran derivatives and thiophene derivatives, oxadiazole derivatives, phthalocyanine derivatives, porphyrin derivatives and other heterocyclic compounds, and polymers having the above monomers in the side chain And styrene derivatives, polythiophene, polyaniline Polyfluorene, polyvinylcarbazole, polysilane, and the like are preferable, but there is no particular limitation as long as it is a compound that can form a thin film necessary for manufacturing a light-emitting element, can inject holes from the anode, and can further transport holes. .

  In the present invention, the light emitting layer is a layer that actually manages light emission by accumulating electric energy injected from the anode and the cathode as energy for light emission. The light emitting layer of the present invention comprises at least a host material and a dopant material. The host material is a compound having a carbazole skeleton represented by the following general formula (1), and the dopant material is a triplet light emitting material.

R 1 to R 24 are each a hydrogen, an alkyl group, a cycloalkyl group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl thioether group, an aryl group, an amino group, a silyl group, or a ring between adjacent substituents. Selected from among structures. However, at least one of R 15 to R 24 is selected from an amino group and a ring structure with an adjacent substituent.

  Among these substituents, the alkyl group represents, for example, a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, or a butyl group, which may be unsubstituted or substituted. The substituent in the case of being substituted is not particularly limited, and examples thereof include an alkyl group, an aryl group, a heteroaryl group, and the like, and this point is common to the following description. Further, the number of carbon atoms of the alkyl group is not particularly limited, but is usually in the range of 1 to 20 from the viewpoint of availability and cost.

  The cycloalkyl group represents a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, and the like, which may be unsubstituted or substituted. Although carbon number of an alkyl group part is not specifically limited, Usually, it is the range of 3-20.

  The alkoxy group refers to, for example, an aliphatic hydrocarbon group via an ether bond such as a methoxy group, and the aliphatic hydrocarbon group may be unsubstituted or substituted. Although carbon number of an alkoxy group is not specifically limited, Usually, it is the range of 1-20.

  The alkylthio group is a group in which an oxygen atom of an ether bond of an alkoxy group is substituted with a sulfur atom.

  The aryl ether group refers to, for example, an aromatic hydrocarbon group via an ether bond such as a phenoxy group, and the aromatic hydrocarbon group may be unsubstituted or substituted. Although carbon number of an aryl ether group is not specifically limited, Usually, it is the range of 6-40.

  The arylthioether group is a group in which the oxygen atom of the ether bond of the arylether group is substituted with a sulfur atom.

  Moreover, an aryl group shows aromatic hydrocarbon groups, such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, a pyrenyl group, for example. The aryl group may be unsubstituted or substituted. Although carbon number of an aryl group is not specifically limited, Usually, it is the range of 6-40.

  The amino group may or may not have a substituent, and examples of the substituent include an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group. These substituents are further substituted. Also good.

  A silyl group refers to, for example, a functional group having a bond to a silicon atom, such as a trimethylsilyl group, which may or may not have a substituent. Although carbon number of a silyl group is not specifically limited, Usually, it is the range of 3-20. The number of silicon is usually 1 or more and 6 or less.

When the ring structure formed between adjacent groups is described in the general formula (1), any two adjacent substituents selected from R 15 to R 19 (for example, R 15 and R 16 ) are mutually bonded. Bonds to form a conjugated or non-serving ring structure. These ring structures may contain nitrogen, oxygen and sulfur atoms in the ring structure, or may be condensed with another ring, but the atoms constituting these ring structures are composed of only carbon atoms and hydrogen atoms. The conjugated ring structure is preferable because excellent heat resistance can be obtained.

The compound having a carbazole skeleton represented by the general formula (1) of the present invention has at least one of R 15 to R 24 substituted with an amino group or a ring structure with an adjacent substituent. Carrier transportability is improved, and both high-efficiency energy transfer to a triplet light-emitting material as a dopant and a low driving voltage can be achieved. As the other substituents R, in view of the effects of the present invention, hydrogen on the carbazole skeleton and substituents having equivalent properties are listed.

  Specific examples of the compound having the carbazole skeleton include the following structures.

  As a triplet light emitting material used as a dopant material, a metal complex having iridium, osmium, rhodium, palladium, platinum as a central metal is preferably used. Specifically, a tris (2-phenylpyridyl) iridium complex, tris {2- (2-thiophenyl) pyridyl} iridium complex, tris {2- (2-benzothiophenyl) pyridyl} iridium complex, tris (2-phenylbenzothiazole) iridium complex, tris (2-phenylbenzoxazole) iridium complex , Trisbenzoquinoline iridium complex, bis (2-phenylpyridyl) (acetylacetonato) iridium complex, bis {2- (2-thiophenyl) pyridyl} iridium complex, bis {2- (2-benzothiophenyl) pyridyl} ( Acetylacetonate Iridium complex, bis (2-phenylbenzothiazole) (acetylacetonato) iridium complex, bis (2-phenylbenzoxazole) (acetylacetonato) iridium complex, bisbenzoquinoline (acetylacetonato) iridium complex, bis {2- (2,4-difluorophenyl) pyridyl} (acetylacetonato) iridium complex, tetraethylporphyrin platinum complex, {tris (cenoyltrifluoroacetone) mono (1,10-phenanthroline)} europium complex, {tris (cenoyltrifluoroacetone) ) Mono (4,7-diphenyl-1,10-phenanthroline)} europium complex, {tris (1,3-diphenyl-1,3-propanedione) mono (1,10-phenanthroline)} europium complex , And the like tris-acetylacetone terbium complex. Although not limited thereto, an iridium complex or a platinum complex is preferably used because high-efficiency light emission is easily obtained.

  If the amount of the dopant material relative to the host material is too large, a concentration quenching phenomenon occurs. As a doping method, it can be formed by a co-evaporation method with a host material, but it may be pre-mixed with the host material and then simultaneously deposited. Alternatively, the host material and the dopant material may be dissolved in a desired ratio and applied.

  The compound having a carbazole skeleton used as a host material and the triplet light emitting material used as a dopant material may each include only one type in the light emitting layer, or a mixture of two or more types may be used. Also good. When two or more triplet light emitting materials are used, the total weight of the dopant material is preferably 20% by weight or less with respect to the host material.

  In addition to the host material and the triplet light emitting material, the light emitting layer may further include a third component for adjusting the carrier balance in the light emitting layer or stabilizing the layer structure of the light emitting layer. . However, as the third component, a material that does not cause an interaction between the host material composed of the compound having the carbazole skeleton and the dopant material composed of the triplet light emitting material is selected.

  Furthermore, the light emitting layer may be composed of a plurality of layers as well as a single layer made of the above material group. In the case of being composed of a plurality of layers, it is sufficient that at least one layer contains the compound having the carbazole skeleton and the triplet light-emitting material, and the fluorescent light comprising the known host material and singlet light-emitting material is contained in the other layers. An ionic dopant material may be used.

  Although it does not specifically limit as a known host material, Condensed ring derivatives, such as anthracene and pyrene which were known as a light-emitting body, 4,4'-bis (N- (1-naphthyl) -N- Aromatic amine derivatives such as phenylamino) biphenyl, metal chelated oxinoid compounds such as tris (8-quinolinolato) aluminum (III), bisstyryl derivatives such as distyrylbenzene derivatives, tetraphenylbutadiene derivatives, indene derivatives, oxadi Azole derivatives, pyrrolopyridine derivatives, perinone derivatives, cyclopentadiene derivatives, oxadiazole derivatives, pyrrolopyrrole derivatives, in polymer systems, polyphenylene vinylene derivatives, polyparaphenylene derivatives, polyfluorene derivatives, polyvinylcarbazole derivatives , Polythiophene derivatives are suitably used.

  The known singlet dopant material is not particularly limited, but specifically, conventionally known compounds having a condensed aryl ring such as pyrene, perylene, rubrene, and derivatives thereof, furan, isobenzofuran. , A compound having a heteroaryl ring such as pyrrole, thiophene, indole, imidazopyridine, pyrazine, pyrrolopyridine, thioxanthene and derivatives thereof, azole derivatives such as imidazole, thiazole, thiadiazole, oxazole, oxadiazole, triazole, benzimidazole, Aromatic amine derivatives, pyrazoline derivatives, stilbene derivatives, pyromethene derivatives and metal complexes thereof, coumarin derivatives such as 3-benzthiazolyl coumarin derivatives, dicyanomethylenepyran derivatives, cyanine derivatives, full Resin derivatives, pyrylium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives, diazaflavin derivatives, etc. it can.

  In the present invention, the electron transport layer is a layer in which electrons are injected from the cathode and further transports electrons. The electron transport layer has high electron injection efficiency, and it is desired to efficiently transport injected electrons. Therefore, it is desirable that the electron transport layer is made of a material having a high electron affinity, a high electron mobility, excellent stability, and a trapping impurity that is unlikely to be generated during manufacture and use. However, considering the transport balance between holes and electrons, if the electron transport layer mainly plays a role of effectively preventing the holes from the anode from recombining and flowing to the cathode side, the electron transport Even if it is made of a material that does not have a high capability, the effect of improving the luminous efficiency is equivalent to that of a material that has a high electron transport capability. Therefore, the electron transport layer in the present invention includes a hole blocking layer that can efficiently block the movement of holes as the same meaning.

  Examples of the electron transport material used in the electron transport layer include condensed polycyclic aromatic derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 4,4′-bis (diphenylethenyl) biphenyl, anthraquinone, diphenoquinone, and the like. Quinoline derivatives, phosphorus oxide derivatives, quinolinol complexes such as tris (8-quinolinolato) aluminum (III), benzoquinolinol complexes, hydroxyazole complexes, azomethine complexes, tropolone metal complexes and flavonol metal complexes. A compound having a heteroaryl ring structure composed of an element selected from carbon, hydrogen, nitrogen, oxygen, silicon, and phosphorus and containing electron-accepting nitrogen, because driving voltage is reduced and high-efficiency light emission is obtained. Is preferably used. In particular, when used in combination with a light-emitting layer containing a compound having a pyromethene skeleton of the present invention or a metal complex thereof and a naphthacene derivative, it is easy to maintain the balance of holes and electrons in the light-emitting element, and the balance is Since it is realized while maintaining a high charge transport capability, it is possible to achieve both a low driving voltage and a long life.

  The electron-accepting nitrogen in the present invention represents a nitrogen atom that forms a multiple bond with an adjacent atom. Since the nitrogen atom has a high electronegativity, the multiple bond has an electron accepting property. Therefore, a heteroaryl ring containing electron-accepting nitrogen has high electron affinity, excellent electron transport ability, and can be used for an electron transport layer to reduce the driving voltage of a light-emitting element. Heteroaryl rings containing electron-accepting nitrogen include, for example, pyridine ring, pyrazine ring, pyrimidine ring, quinoline ring, quinoxaline ring, naphthyridine ring, pyrimidopyrimidine ring, benzoquinoline ring, phenanthroline ring, imidazole ring, oxazole ring, oxalate ring, Examples include a diazole ring, a triazole ring, a thiazole ring, a thiadiazole ring, a benzoxazole ring, a benzothiazole ring, a benzimidazole ring, and a phenanthrimidazole ring.

  Examples of these compounds having a heteroaryl ring structure include benzimidazole derivatives, benzoxazole derivatives, benzthiazole derivatives, oxadiazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazine derivatives, phenanthroline derivatives, quinoxaline derivatives, quinoline derivatives, benzoins. Preferred compounds include quinoline derivatives, oligopyridine derivatives such as bipyridine and terpyridine, quinoxaline derivatives and naphthyridine derivatives. Among them, imidazole derivatives such as tris (N-phenylbenzimidazol-2-yl) benzene, oxadiazole derivatives such as 1,3-bis [(4-tert-butylphenyl) 1,3,4-oxadiazolyl] phenylene, Triazole derivatives such as N-naphthyl-2,5-diphenyl-1,3,4-triazole, phenanthroline derivatives such as bathocuproine and 1,3-bis (1,10-phenanthroline-9-yl) benzene, 2,2 ′ A benzoquinoline derivative such as bis (benzo [h] quinolin-2-yl) -9,9′-spirobifluorene, 2,5-bis (6 ′-(2 ′, 2 ″ -bipyridyl))-1, Bipyridine derivatives such as 1-dimethyl-3,4-diphenylsilole, 1,3-bis (4 ′-(2,2 ′: 6′2 ″ -ta Terpyridine derivatives such as pyridinyl)) benzene, naphthyridine derivatives such as bis (1-naphthyl) -4- (1,8-naphthyridin-2-yl) phenylphosphine oxide are preferably used from the viewpoint of electron transporting capability.

  The electron transport material may be used alone, but two or more of the electron transport materials may be mixed and used, or one or more of the other electron transport materials may be mixed and used in the electron transport material. It is also possible to use a mixture with a metal such as an alkali metal or an alkaline earth metal. The ionization potential of the electron transport layer is not particularly limited, but is preferably 5.8 eV or more and 8 eV or less, more preferably 6 eV or more and 7.5 eV or less.

  The method of forming each of the above layers constituting the light emitting element is not particularly limited, such as resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, coating method, ink jet method, printing method, laser induced thermal transfer method, etc. From this point, resistance heating vapor deposition or electron beam vapor deposition is preferable.

  The light-emitting element of the present invention is a light-emitting element that can convert electrical energy into light. Here, the electric energy mainly indicates a direct current, but a pulse current or an alternating current can also be used. The current value and the voltage value are not particularly limited, but the maximum luminance can be obtained with as low energy as possible in consideration of the power consumption and lifetime of the element.

  The light emitting device of the present invention is suitably used as a display for displaying in a matrix and / or segment system, for example.

  The matrix system in the present invention refers to a pixel in which pixels for display are two-dimensionally arranged such as a lattice shape or a mosaic shape, and displays characters and images by a set of pixels. The shape and size of the pixel are determined by the application. For example, a square pixel with a side of 300 μm or less is usually used for displaying images and characters on a personal computer, monitor, TV, and a pixel with a side of mm order for a large display such as a display panel. become. In monochrome display, pixels of the same color may be arranged. However, in color display, red, green, and blue pixels are displayed side by side. In this case, there are typically a delta type and a stripe type. The matrix driving method may be either a line sequential driving method or an active matrix. The line-sequential driving has an advantage that the structure is simple, but the active matrix may be superior in consideration of operation characteristics.

  In the segment system (type) in the present invention, a pattern is formed so as to display predetermined information, and a predetermined region is caused to emit light. For example, the time and temperature display in a digital clock or a thermometer, the operation state display of an audio device or an electromagnetic cooker, the panel display of an automobile, and the like can be mentioned. The matrix display and the segment display may coexist in the same panel.

  The light emitting device of the present invention is also preferably used as a backlight for various devices. The backlight is used mainly for the purpose of improving the visibility of a display device that does not emit light, and is used for a liquid crystal display device, a clock, an audio device, an automobile panel, a display panel, a sign, and the like. In particular, as a backlight for a liquid crystal display device, especially a personal computer for which thinning is a problem, considering that it is difficult to thin the conventional backlight because it is made of a fluorescent lamp or a light guide plate, the present invention The backlight using the light emitting element in can be made thin and light.

  EXAMPLES Hereinafter, although an Example and a comparative example are given and this invention is demonstrated, this invention is not limited by these examples. In addition, the number of the compound in each following Example points out the number of the compound described above.

Example 1
A glass substrate (manufactured by Geomat Co., Ltd., 11Ω / □, product formed by sputtering) on which an ITO transparent conductive film was deposited to 150 nm was cut into 38 × 46 mm and etched. The obtained substrate was ultrasonically cleaned with “Semicocrine 56” (trade name, manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes and then with ultrapure water. This substrate was subjected to UV-ozone treatment for 1 hour immediately before producing the device, placed in a vacuum deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 × 10 −4 Pa or less. By the resistance heating method, first, copper phthalocyanine was deposited as a hole injecting material at 10 nm, and 4,4′-bis (N- (1-naphthyl) -N-phenylamino) biphenyl was deposited as a hole transporting material at 50 nm. Next, the compound [2] as a host material and a bis (2-phenylquinoline) (acetylacetonato) iridium complex as a dopant material were vapor-deposited to a thickness of 35 nm so as to have a doping concentration of 10%. . Next, bis (2-methyl-8-quinolinolato)-(4-phenylphenolate) aluminum complex is 10 nm as the hole blocking material, and tris (8-quinolinolato) aluminum complex is 65 nm thick as the electron transporting material. Laminated. Next, after depositing 0.5 nm of lithium fluoride, 1000 nm of aluminum was vapor-deposited to form a cathode, and a 5 × 5 mm square device was fabricated. The film thickness referred to here is a crystal oscillation type film thickness monitor display value. When this light emitting element was DC-driven at 10 mA / cm 2 , red light emission with a light emission efficiency of 5 cd / A and chromaticity CIE (x, y) = (0.66, 0.33) was obtained. The voltage was 8V.

Comparative Example 1
A light emitting device was produced in the same manner as in Example 1 except that 4,4′-bis (N-carbazolyl) biphenyl (CBP) was used as the host material of the light emitting material. When this light emitting device was DC-driven at 10 mA / cm 2 , red light emission with a luminous efficiency of 4.3 cd / A and chromaticity CIE (x, y) = (0.65, 0.33) was obtained. The drive voltage was 13.3V.

Example 2
Example 1 except that 1,3-bis (1,10-phenanthroline-9-yl) benzene was vapor-deposited to a thickness of 75 nm as an electron transport material instead of the hole blocking material and the electron transport material of Example 1. In the same manner as in Example 1, a light emitting device was manufactured. When this light emitting device was DC driven at 10 mA / cm 2 , red light emission with a light emission efficiency of 5.8 cd / A and chromaticity CIE (x, y) = (0.69, 0.30) was obtained. The driving voltage was 5.8V.

Example 3
A light emitting device was produced in the same manner as in Example 2 except that the host material of the light emitting material was changed to the compound [7]. When this light emitting element was DC-driven at 10 mA / cm 2 , red light emission with a luminous efficiency of 6 cd / A and chromaticity CIE (x, y) = (0.69, 0.30) was obtained. The voltage was 7.3V.

Example 4
A glass substrate (manufactured by Asahi Glass Co., Ltd., 15Ω / □, product formed by an electron beam method) on which an ITO transparent conductive film is deposited by 150 nm is cut into 30 × 40 mm, and 300 μm pitch (remaining width 270 μm) × 32 by photolithography. Patterned into strips of books. One side of the ITO stripe in the long side direction is expanded to a pitch of 1.27 mm (opening width 800 μm) in order to facilitate electrical connection with the outside. The obtained substrate was subjected to ultrasonic cleaning with “Semicocrine 56” and ultrapure water for 15 minutes, respectively, and then dried. This substrate was subjected to UV-ozone treatment for 1 hour immediately before producing the light-emitting element, placed in a vacuum vapor deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 × 10 −4 Pa or less. First, 4,4′-bis (N- (1-naphthyl) -N-phenylamino) biphenyl (αNPD) was deposited as a hole transporting material by a resistance heating method to a thickness of 60 nm. Next, the compound [2] as a host material and a bis (2-phenylquinoline) (acetylacetonato) iridium complex as a dopant material were vapor-deposited to a thickness of 35 nm so as to have a doping concentration of 10%. . Next, 1,3-bis (1,10-phenanthroline-9-yl) benzene was deposited as an electron transporting material to a thickness of 75 nm. Next, the mask having 16 250 μm openings (corresponding to the remaining width of 50 μm and 300 μm pitch) formed by wet etching on a 50 μm thick Kovar plate was replaced in a vacuum so as to be orthogonal to the ITO stripe. And it fixed with the magnet from the back so that an ITO board | substrate might contact | adhere. And after doping lithium with a 0.5 nm organic layer, aluminum was vapor-deposited 200 nm, and the 32 * 16 dot matrix element was produced. When this element was driven in matrix, characters could be displayed without crosstalk.

Claims (2)

  1. A light emitting layer composed of at least a host material and a dopant material exists between an anode and a cathode, and is an element that emits light by electric energy, and the host material is a compound having a carbazole skeleton represented by the general formula (1) A light-emitting element, wherein the dopant material is a triplet light-emitting material.
    (R 1 to R 24 are each hydrogen, an alkyl group, a cycloalkyl group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl thioether group, an aryl group, an amino group, a silyl group, or an adjacent substituent. (It is selected from ring structures, provided that at least one of R 15 to R 24 is selected from an amino group and a ring structure with an adjacent substituent.)
  2. At least an electron transport layer exists between the light emitting layer and the cathode, and the electron transport layer is composed of an element selected from carbon, hydrogen, nitrogen, oxygen, silicon, and phosphorus, and includes a heteroaryl ring containing electron-accepting nitrogen The light emitting device according to claim 1, comprising a compound having a structure.
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