WO2006100888A1 - Material for organic el device, organic el device, display and illuminating device - Google Patents

Abstract

Disclosed is a material for organic EL devices which is high in synthesis yield and luminous efficiency while having long emission life. Also disclosed are an organic EL device using such a material, and a display and illuminating device using such an organic EL device. The organic EL material is composed of a metal complex having a partial structure represented by the general formula (1) below, and is characterized by having at least one substituent in a ligand part which suppresses bidentate coordination.

Description

 Specification

 Materials for organic EL elements, organic EL elements, display devices and lighting devices

 Technical field

 The present invention relates to an organic EL element material, and an organic EL element, a display device, and an illumination device using the same.

 Background art

 Conventionally, there is an EL display (hereinafter referred to as ELD) as a light-emitting electronic display device. ELD components include inorganic EL elements and organic EL elements. Inorganic EL elements have been used as planar light sources, but a high AC voltage is required to drive the light emitting elements. An organic EL device has a structure in which a light-emitting layer containing a light-emitting compound is sandwiched between a cathode and an anode, and electrons and holes are injected into the light-emitting layer and recombined to generate excitons. This is an element that emits light by using light emission (fluorescence / phosphorescence) when this exciton is deactivated, and can emit light at a voltage of several volts to several tens of volts, and is self-luminous. In addition, it is a thin-film, complete solid-state device with a wide viewing angle and high visibility, so it is attracting attention from the viewpoint of space saving and portability.

 [0003] However, for organic EL elements for practical use in the future, it is desired to develop organic EL elements that emit light efficiently and with high luminance with lower power consumption.

 [0004] In Japanese Patent No. 3093796, a small amount of phosphor is doped into a stilbene derivative, a distyrylarylene derivative or a tristyrylarylene derivative to improve emission luminance and extend the lifetime of an organic EL device. And les.

 [0005] Further, an organic EL device having an organic light emitting layer in which an 8-hydroxyquinoline aluminum complex is used as a host compound and a small amount of a phosphor is doped therein (for example, Japanese Patent Laid-Open No. 63-264692), 8 An organic EL device having an organic light emitting layer in which a hydroxyquinoline aluminum complex is a host compound and doped with a quinatalidone dye is known (for example, JP-A-3-255190).

[0006] As described above, when emission from excited singlet is used, the generation ratio of singlet excitons and triplet excitons is 1: 3, so the generation probability of luminescent excited species is 25%. Extraction effect Since the rate is about 20%, the limit of external extraction quantum efficiency ext) is set to 5%.

[0007] However, Princeton University has reported on organic EL devices using phosphorescence from excited triplets (MA Baldo et al., Nature, 395 卷, 151-: 154 (1998)). Recently, research on materials that exhibit phosphorescence at room temperature has become active. For example, M. A. Baldo et al., Nature, 403 卷, 17, 750-753 (2000), and US Pat.

No. 97, 147 and the like are also disclosed.

[0008] The upper limit of internal quantum efficiency is 100 when excited triplets are used. As a result, the luminous efficiency is S4 times in principle compared to the case of singlet excitation, and there is a possibility of obtaining almost the same performance as a cold cathode tube. .

[0009] For example, in S. Lamansky et al., J. Am. Chem. So, 123 卷, p. 4304 (2001), many compounds have been synthesized and studied focusing on heavy metal complexes such as iridium complexes. ing.

 [0010] In addition, in the above-mentioned MA Baldo et al., Nature, 403 卷, 17, 750-753 (2000), a study using tris (2-phenylpyridine) iridium as a dopant was conducted. Has been.

 [0011] In addition, M. E. Tompson et al.

 In Workshop on Inorganic and Organic Electroluminescence (EL 00, Hamamatsu), L Ir (acac), for example, (ppy) Ir (acac) as a dopant, and Moon—Jae Youn. Og, Tetsuo Tsutsui, etc. In Workshop on Inorganic and Organic Electroluminescence (EL'00, Hamamatsu), as dopants, tris (2- (p-tolyl) pyridine) iridium (Ir (ptpy)), tris (benzo [h] quinoline) iridium (Ir (bzq)) etc. are being studied. These metal complexes are generally called orthometalated iridium complexes.

 [0012] In addition, in the above-mentioned S. Lamansky et al., J. Am. Chem. So, 123 頁, p. 4304 (2001), attempts have been made to make organic EL devices using various iridium complexes. Yes.

[0013] In order to obtain high luminous efficiency, the 10th International Workshop on Inorganic and Organic Electroluminescence (EL'00, Hamamatsu) Uses a hole transporting compound as a host of a phosphorescent compound. In addition, ME Thompson et al. Use various electron transport materials as a host of phosphorescent compounds and dope these with new iridium complexes.

 [0014] An onoleto metal complex having a central metal platinum instead of iridium is also attracting attention. With regard to this type of complex, there are many known examples in which a ligand is characterized (see, for example, Patent Documents:! To 7).

 [0015] In any case, bidentate ligands and derivatives thereof, which are mainly bonded to the central metal through two coordination atoms, such as phenylpyridine, have been used as preferred examples of orthometalated complexes. The light emission brightness and light emission efficiency when these are used as light emitting elements are greatly improved compared to conventional organic EL elements because the emitted light is derived from phosphorescence. It is known that the lifetime is lower than that of conventional organic EL devices.

 [0016] In recent years, platinum complexes and iridium complexes using a tridentate ligand having three coordination atoms have been reported (see, for example, Patent Documents 8 and 9 and Non-Patent Documents 1 and 2). However, the light-emitting properties of these organic EL devices are still insufficient, and there has been a demand for the development of organic EL devices that use high-performance phosphorescent materials that can withstand practical use.

 Patent Document 1: Japanese Patent Laid-Open No. 2001-181617

 Patent Document 2: Japanese Patent Laid-Open No. 2001-247859

 Patent Document 3: Japanese Patent Laid-Open No. 2002-332291

 Patent Document 4: Japanese Patent Laid-Open No. 2002-332292

 Patent Document 5: Japanese Unexamined Patent Application Publication No. 2002-338588

 Patent Document 6: Japanese Patent Laid-Open No. 2002-226495

 Patent Document 7: Japanese Patent Laid-Open No. 2002-234894

 Patent Document 8: Japanese Unexamined Patent Publication No. 2003-73355

 Patent Document 9: W〇2004Z39781 Non-Fret

 Non-Patent Document 1: Inorganic Chemistry, No. 43, No. 21, pp. 6513-6515 (2004)

Non-Patent Document 2: IDW 2004, pages 1425-1426 Disclosure of the invention

 Problems to be solved by the invention

 [0017] The present invention has been made in view of the above problems, and an object of the present invention is to provide a material for an organic EL element having a high synthesis yield and a high light emission efficiency and a long emission lifetime, an organic EL element using the same, and It is to provide a display device and a lighting device using an EL element.

 Means for solving the problem

[0018] The above-described problems of the present invention are achieved by the following configurations.

 [0019] (1) A metal complex having a partial structure represented by the following general formula (1), characterized in that the ligand portion has at least one substituent that suppresses bidentate coordination. Materials for organic EL devices.

 [0020] [Chemical 1]

 [In the formula, M is a metal atom, X, Y, and Ζ are constituents of ring Α, ring Β, and ring C, respectively, and are a carbon atom or a nitrogen atom, and at least one is a carbon atom. The ring Α, ring Β, and ring C are aromatic hydrocarbon rings, aromatic heterocycles, or heterocycles R to R are substituents, and nl, n2, and n3 are 0 or a positive integer L is auxiliary

 13

 Represents a ligand, and m is an integer of 1 to 3. )

 (2) In the general formula (1), at least one of the substituents R of the ring B includes a ring A and a ring C;

 2

No bond, van der Waals volume (VDW) force S45A ³ or more alkyl group, cycloanolalkyl group, alkenyl group, alkynyl group, heterocyclic group, alkoxy group, cycloalkoxy group, snorfininore group, alkylsulfonyl group or silyl group Before characterized by The material for an organic EL device according to (1).

[0022] (3) An organic EL device comprising the organic EL device material according to any one of the above (1) and (2) in one of the constituent layers forming the organic EL device. EL element.

[0023] (4) The organic EL device according to (3), wherein one of the constituent layers is a light emitting layer.

 [0024] (5) The organic EL device according to (3) or (4), wherein a compound represented by the following general formula (2) is contained in at least one of the constituent layers.

[0025] [Chemical 2]

—General formula << 2ί

[0026] (wherein Z represents an atomic group forming an aromatic heterocycle, Z represents an aromatic heterocycle or aromatic

 1 2

 Represents a group of atoms that form an aromatic hydrocarbon ring, and Z represents a divalent linking group or a simple bond.

 Three

 The R represents a hydrogen atom or a substituent. )

 Four

 (6) A display device comprising the organic EL element according to the item (3) to (5), and the displacement force described in item 4.

 [0027] (7) A lighting device comprising the organic EL element according to item (3) to (5), wherein the organic EL element according to item 1 is provided.

 [0028] Regarding the following (8) to (16), at least one substituent having a partial structure represented by the general formula (1) and suppressing bidentate coordination is coordinated. The preferred and mode of materials for organic EL elements that are metal complexes in the child part are shown.

[0029] (8) In the above general formula (1), at least one of ring A and ring C is a monocyclic nitrogen-containing 5-membered ring, described in (1) or (2) above Material for organic EL devices.

[0030] (9) In the general formula (1), at least one of the ring A and the ring C is a heterocyclic ring bonded to the ring B with a nitrogen atom, (1), (2) And (8) Any of the forces described in item 1 for organic EL device materials. [0031] (10) In the general formula (1), Y is a carbon atom, and the auxiliary ligand L is bonded to the metal M by a carbon atom, a nitrogen atom, or a sulfur atom. The material for an organic EL device according to any one of (1), (2), (8) and (9).

 (11) In the general formula (1), Y is a nitrogen atom, and the auxiliary ligand L is bonded to the metal M through a nitrogen atom, an oxygen atom, or a sulfur atom. 10. The organic EL device material according to any one of (1), (2), (8) and (9), which is characterized in that

 [0033] (12) In the general formula (1), the auxiliary ligand L is a dione bonded to the metal M by a nitrogen atom, (1), (2), (8) The material for organic EL elements according to 1 above, wherein any one of (9) and (11) is used.

 [0034] (13) In the above general formula (1), at least one of the auxiliary ligands L is a bidentate ligand. (1), (2) and (8) Any of the powers of (12) to the organic EL element material according to item 1.

 [0035] (14) In the general formula (1), the metal M is Ir, Pt, Rh, Pd, Os or Au, (1), (2) and (8) to (13 The organic EL element material described in item 1 above.

 [0036] (15) The material for an organic EL element as described in 14 above, wherein in the general formula (1), the metal M is Pt, Pd or Au.

[0037] (16) The metal complex represented by the general formula (1) is a part of a main chain or a side chain of the polymer (1), (2) and (8) Any of the powers of ~ (: 15)

Materials for EL elements.

 The invention's effect

 [0038] According to the present invention, there are provided a material for an organic EL element having a high synthesis yield and luminous efficiency and a long emission lifetime, an organic EL element using the material, a display device using the organic EL element, and a lighting device. That power S.

 Brief Description of Drawings

 FIG. 1 is a schematic view showing an example of a display device composed of organic EL elements.

 FIG. 2 is a schematic diagram of display unit A.

FIG. 3 is an equivalent circuit diagram of a drive circuit constituting a pixel. FIG. 4 is a schematic diagram of a passive matrix display device.

 FIG. 5 is a schematic diagram of a sealing structure of an organic EL element.

 FIG. 6 is a schematic diagram of a lighting device including an organic EL element.

 Explanation of symbols

[0040] 1 display

 3 pixels

 5 scan lines

 6 Data line

 7 Power line

 10 Organic EL devices

12 Drive transistor

 13 Capacitor

 A Display section

 B Control unit

 101 Glass substrate with transparent electrode

 102 OLED layer

 103 cathode

 104 glass sealing can

 105 Barium oxide (water trapping agent)

 106 Nitrogen gas

 107 UV curable adhesive

 BEST MODE FOR CARRYING OUT THE INVENTION

[0041] The organic EL device material of the present invention has a tridentate ligand having three rings, and each ring is directly bonded. Such tridentate ligands have more bonds with the central metal than bidentate ligands such as phenylpyridine, which have been used so far, making it easy to transfer energy between the metal and ligand. Thus, highly efficient light emission is possible, and more stabilization energy associated with complex formation can be obtained. [0042] In the present invention, the organic EL device material described in any one of (1) or (2) or (8) to (16) is preferably used. As a result, it was possible to obtain an organic EL device having a high emission efficiency and a long emission lifetime.

 [0043] As a result of diligent investigations on the above problems, the present inventors have replaced the bidentate ligands that have been studied in various fields so far, as shown in the general formula (1). It has been found that by using a metal complex using a bidentate ligand, it is possible to provide a material for an organic EL device that has a high synthesis yield and luminous efficiency and has a significantly improved luminous lifetime.

[0044] The tridentate ligand according to the present invention has three ring structures of ring A, ring B, and ring C, and has a substituent that suppresses bidentate coordination. Such a substituent enables the metal to selectively form a tridentate coordination with a ligand, and a desired metal complex can be obtained with high selectivity. At this time, the bonding position and bulkiness of the substituent are not particularly limited as long as bidentate coordination can be suppressed, but in particular, ring B has a substituent of van der Waals volume (VDW) force S45A ³ or more. it is preferred instrument 45～250A ³ is a more preferable device 45: it forces S more preferably 150A is ^three. As the types of substituents, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a heterocyclic group, an alkoxy group, a cycloalkoxy group, a sulfinyl group, an alkylsulfonyl group, and an alkyl group, preferably a silyl group, A cycloalkyl group, an alkenyl group, an alkynyl group, an alkoxy group and a silyl group are more preferred, and an alkyl group, a cycloalkyl group, an alkenyl group and a silyl group are more preferred.

 [0045] The tridentate ligand in the present invention has three ring structures, and these are aromatic hydrocarbon rings, aromatic heterocyclic rings or heterocyclic rings, which are 5-membered or 6-membered rings. Is preferred. In particular, ring B preferably has a 6-membered ring structure. In order to adjust the emission wavelength, at least one of ring A or ring C is preferably a nitrogen-containing 5-membered ring structure or a heterocyclic ring bonded to ring B with a nitrogen atom.

[0046] According to the study by the present inventors, the tridentate ligand has coordinating atoms X, Y, and に in ring A, ring B, and ring C, respectively. It became clear that the selection of the auxiliary ligand L has a great influence on the stability and emission characteristics of organic EL devices. Specifically, in the general formula (1), when the ring Υ is a carbon atom, the auxiliary ligand L is preferably bonded to the metal に よ っ て by a carbon atom, a nitrogen atom, or a sulfur atom. Mashigu ring When Y in B is a nitrogen atom, the auxiliary ligand L is preferably bonded to the metal cage by a nitrogen atom, oxygen atom, or sulfur atom.

[0047] The auxiliary ligand L is preferably an anion bonded to the metal cage with a nitrogen atom.

[0048] The auxiliary ligand L may be one kind or more, but preferably satisfies the coordination number of the central metal. For this reason, the auxiliary ligand may be monodentate, bidentate or tridentate, or a combination thereof. However, if there are multiple vacant coordination sites, the chelating effect In order to obtain stabilization, it is preferable to use a double-dentate ligand. Further, it is more preferable that the material for the organic EL element has a counter ion but is neutral as a whole.

 [0049] The central metal is not particularly limited as long as it can emit phosphorescence, but is preferably a metal included in Group 8 to 11 in the periodic table: Ir, Pt, Pd, Rh, Pt, Pd or Au is more preferred, with Os or Au being more preferred.

 [0050] The method for producing the organic EL device is not particularly limited, but the metal complex in the present invention, which is preferably wet, is preferably a main chain or a part of a side chain of the polymer chain.

 [0051] The material for an organic EL device of the present invention is preferably used for a light emitting layer among the constituent layers of the organic EL device. It is preferable to be used as a dopant in the light emitting layer for further highly efficient light emission. At this time, by combining with the materials that make up the other organic layers, such as the electron transport layer used, the hole transport layer, and the light-emitting host, it is possible to emit light with higher brightness and higher efficiency, and to further increase the lifetime of the organic EL device Is possible. From this point of view, it is preferable to use the general formula (2) as a light emitting host and / or hole blocking material that preferably uses the compound represented by the general formula (2) in at least one of the organic layers. preferable.

 [0052] Hereinafter, the present invention will be described in detail.

 [Metal complex represented by general formula (1)]

 The metal complex having a partial structure represented by the general formula (1) of the present invention (hereinafter also referred to as a metal complex represented by the general formula (1)) will be described.

[0054] The present inventors have replaced a bidentate ligand that has been studied in various fields so far with a metal complex using a tridentate ligand represented by the general formula (1). By using this, it is possible to provide materials for organic EL devices that have a high synthesis yield and light emission efficiency, and that have a significantly improved light emission lifetime. It was.

[0055] The tridentate ligand in the present invention has three ring structures of ring A, ring B, and ring C directly connected by a carbon atom. In particular, ring B has a van der Waals volume (VDW) of 45 A. It preferably has ³ or more substituents. Such bulky substituents allow the metal to selectively tridentate with the ligand and prevent the formation of undesirable bidentate complexes.

 卜 O C

 [0056] replacement 卜

 Basic van der Waals O O L

 σι Dimension D CD C volume (VDW) volume means Accelrys molecular simulation M 〇 C

 Force using parameters determined by Yonsoft Cerius2 Introducing substituents into the benzene ring, optimizing the molecular structure using MM calculation using Dreiding Force Field, and using Connoly Surface Defined as a Volume value. Specific van der Waals (VDW) volumes of substituents are shown below.

Substituent A ³

 Methyl group

 Ethyl group 42.6

 Isopropyl group

 tert-butyl group

 Trimethylsilyl group 91.9

 Phenyl group

Phenoxy group

 Methoxy group

 Amino group 22.2

 Dimethinoreamino group

 Hydroxy group

 Chlorine atom

 Bromine atom

 Fluorine atom 13.3

 Trifluoromethyl group

Ring A, ring B, and ring C are aromatic hydrocarbon rings, aromatic heterocycles, or heterocycles. [0058] The aromatic hydrocarbon rings constituting Ring A, Ring B, and Ring C include benzene ring, biphenyl ring, naphthalene ring, azulene ring, anthracene ring, phenanthrene ring, pyrene ring, talycene ring, naphthacene ring, triphenyl ring. Diene ring, o-terfenyl ring, m-terphenyl ring, p-thenophenyl ring, acenaphthene ring, coronene ring, fluorene ring, fluoranthrene ring, naphthacene ring, pentacene ring, perylene ring, pentaphen ring, picene ring, Examples include a pyrene ring, a pyranthrene ring, and an anthraanthrene ring.

 [0059] The aromatic heterocyclic ring constituting Ring A, Ring B, and Ring C includes a furan ring, a thiophene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, a benzimidazole ring, and an oxadiazole ring. , Triazole ring, imidazole ring, pyrazole ring, thiazole ring, indole ring, benzimidazole ring, benzothiazole ring, benzoxazole ring, quinoxaline ring, quinazoline ring, phthalazine ring, force rubazole ring, canoleporin ring, diaza force And a rubazole ring (representing a ring in which one of the carbon atoms of the hydrocarbon ring constituting the carboline ring is further substituted with a nitrogen atom).

 [0060] R to R are substituents, and examples of the substituent include an alkyl group (for example, a methyl group and an ethyl group).

 13

Propyl group, isopropyl group, tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group, tridecyl group, tetradecinole group, pentadecyl group, etc.), cycloalkyl group (for example, cyclopentyl group, cyclohexyl group, etc.) ), Alkenyl groups (eg, vinyl groups, aryl groups, etc.), alkynyl groups (eg, ethynyl groups, propargyl groups, etc.), aryl groups (eg, phenyl groups, naphthyl groups, etc.), aromatic heterocyclic groups (eg, furyl) Group, phenyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyraduryl group, triazinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, quinazolinyl group, phthalagel group, etc.), bicyclic ring group (for example, pyrrolidinole group, imidazolidinole group) , Morpholyl group, oxazolidyl group, etc.), alkoxyl (For example, methoxy group, ethoxy group, propyloxy group, pentyloxy group, hexyloxy group, octyloxy group, dodecinoleoxy group, etc.), cycloalkoxy group (for example, cyclopentyloxy group, cyclohexyloxy group, etc.), aryloxy group ( For example, phenoxy group, naphthyloxy group, etc.), alkylthio group (for example, methenoretio group, ethylthio group, propylthio group, pentylthio group, hexylthio group, octylthio group, dodecinoretio group, etc.), cycloalkylthio group (for example, cyclopentylthio group). Group, cyclohexenoretio group, etc.), arylthio group (for example, phenylthio group, naphthylthio group, etc.), alkoxycarbonyl group (for example, methyloxycarbonyl group, ethyloxycarbonyl group, butoxycarbonyl group, Octyloxycarbonyl group, dodecyloxycarbonyl group, etc.), aryloxycarbonyl group (eg, phenylcarbonyl group, naphthyloxycarbonyl group, etc.), sulfamoyl group (eg, aminosulfonyl group, methyl) Aminosulfonyl group, dimethylaminosulfonyl group, butyraminosulfonyl group, hexylaminosulfonyl group, cyclohexylaminosulfonyl group, octylaminosulfonyl group, dodecylaminosulfonyl group, phenylaminosulfonyl group, naphthylaminosulfonyl group, 2 _Pyridylaminosulfonyl group, etc.), acyl groups (eg, acetyl group, ethylcarbonyl group, propylcarbonyl group, pentylcarbonyl group, cyclohexylcarbonyl group, octylcarbonyl group, 2_ethylhexylcarbonyl group, dodecylcarbocycle group) Diyl group, phenylcarbonyl group, naphthylcarbonyl group, pyridylcarbonyl group, etc.), acyloxy group (eg, acetyloxy group, ethylcarbonyloxy group, butylcarbonyloxy group, octylcarbonyloxy group, dodecylcarbonyloxy group) , Phenylcarbonyloxy groups, etc.), amide groups (eg, methylcarbonylamino groups, ethylcarbonylamino groups, dimethylcarbonylamino groups, propylcarbonylamino groups, pentylcarbonylamino groups, cyclohexylcarbonylamino groups, etc.) A mino group, a 2-ethylhexylcarbonylamino group, an octylcarbonylamino group, a dodecylcarbonylamino group, a phenylcarbonylamino group, a naphthylcarbonylamino group, etc., a canolamoyl group (for example, an aminocarbonyl group, Methylaminocanolonyl group, dimethylamino group, propylaminocarbonyl group, pentylaminocarbonyl group, cyclohexylaminocarbonyl group, octylaminocarbonyl group, 2-ethylhexylaminocarbonyl group, dodecylamino Carbonyl group, phenylaminocarbonyl group, naphthylaminocarbonyl group, 2_pyridylaminocarbonyl group, etc.), ureido group (for example, methylureido group, ethylureido group, pentylureido group, cyclohexylureido group, octylureido group, Dode Silureido group, phenylureido group, naphthylureido group, 2_pyridinoreaminoureido group, etc.), sulfiel group (for example, methylsulfiel group, ethylsulfinyl group, butylsulfinyl group, cyclohexylsulfinyl group, 2_ethylhexylsulfurate) Fier group, dodecylsulfinyl group, phenylsulfinyl group, naphthylsulfinyl group, 2-pyridylsulfinyl group, etc.), alkylsulfonyl group (for example, methylsulfonanol group, ethylsulfonyl group, butylsulfonyl group, cyclohexylsulfonyl group, 2-ethylhexylsulfonyl group, dodecylsulfonyl group, etc.), arylsulfonyl group (eg, phenylsulfonyl group, naphthylsulfonyl group, 2-pyridylsulfonyl group, etc.), amino group (eg, amino group, ethynoleamino group, Dimethinoreamino group, Butinoreamino group, Cyclic pentylamino group, 2-Ethylhexylamino group, Dodecylamino group, Anilino group, Naphtylamino group, 2_pyridinoleamino group, etc.), Halogen atom (for example, fluorine atom, chlorine atom, bromine atom, etc.) ) Fluorohydrocarbon groups (for example, fluoromethyl group, trifluoromethyl group, pentafluoroethyl group, pentafluorophenyl group, etc.), cyan group, nitro group, hydroxy group, mercapto group, silyl group ( For example, a trimethylsilyl group, a triisopropylsilyl group, a triphenylsilyl group, a phenyljetylsilyl group, and the like. These substituents may be further substituted with the above substituents.

[0061] nl, n2, and n3 are 0 or a positive integer, and an integer of 0 to 4 is preferable.

[0062] Specific examples of the metal complex represented by the general formula (1) preferably used in the present invention are listed below, but the present invention is not limited thereto.

[0063] [Chemical 3]

[[]]

[0065] [Chemical 5] [9 ^] [9900]

Z90tO £ l900Zdt / L3d 9188800T / 9001 OAV [Z900]

 [0068] These compounds can be synthesized with reference to D. J. Cardenas, etal., Organometallics 18, 3337 (199 9) and the like.

[0069] The compound represented by the general formula (1) of the present invention is preferably used in at least one of the constituent layers (organic layers) of the organic EL device. In order to further improve the light emission efficiency, one of the constituent layers is a light emitting layer, and it is preferable to use a compound represented by the general formula (1) as a dopant in this light emitting layer. At this time, by using an appropriate combination with the materials constituting the other organic layers, such as the electron transport layer used, the hole transport layer, and the light emitting host, light emission with higher brightness and higher efficiency can be achieved. Furthermore, it is possible to extend the life of organic EL devices.

[0070] [Application of organic EL element materials to organic EL elements]

 When an organic EL device is produced using the organic EL device material of the present invention, it is preferably used for the light emitting layer in the constituent layers (details will be described later) of the organic EL device. In the light emitting layer, as described above, it is preferably used as a light emitting dopant.

[0071] (Luminescent Host and Luminescent Dopant)

 The mixing ratio of the light-emitting dopant to the light-emitting host, which is a host compound as a main component in the light-emitting layer, is preferably 0.:! To less than 30 mass%.

[0072] However, the luminescent dopant may be a mixture of a plurality of types of compounds. The partner to be mixed may have a different structure, and other metal complexes or phosphorescent dopants or fluorescent dopants having other structures may be used. Good.

[0073] Here, the dopant (phosphorescent dopant, fluorescent dopant, etc.) that may be used in combination with the metal complex used as the light emitting dopant will be described. Luminescent dopants can be broadly divided

There are two types: fluorescent dopants that emit fluorescence and phosphorescent dopants that emit phosphorescence.

 [0074] Representative examples of the former (fluorescent dopant) include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes. And pyrylium dyes, perylene dyes, stilbene dyes, polythiophene dyes, and rare earth complex phosphors.

 [0075] A typical example of the latter (phosphorescent dopant) is preferably a complex compound containing a metal of group 8 to 10 in the periodic table of elements, more preferably an iridium compound or an osmium compound. Of these, iridium compounds are most preferred.

 [0076] Specifically, it is a compound described in the following patent publications.

[0077] International Publication No. 00/70655 Pamphlet, JP 2002-280178, 2001-181616, 2002-280179, 2001-181617, 2002-280180, 2001-247859, 2002-299060, 20 01-313178, 2002-302671, 2001-345183, 2002-324679, WO 02/15645, pamphlet , JP 2002-33 No. 2291, No. 2002-50484, No. 2002-332292, No. 2002-8 3684, No. 2002-540572, No. 2002-117978, No. 2002-338588, 2002-170684, 2002-352960, WO 01/93642, JP 2002-50483, 2002-10047 6, 2002-173674, 2002- 359082 Publication No. 2002-175 884 Publication No. 2002-363552 Publication No. 2002-184582 Publication No. 2003-7469 Publication Special Table No. 2002-525808 Publication No. JP 2003-7471 Publication No. Table 2002-525833, JP 2003-31366, 2002-226495, 2002-234894, 2002-235076, 2002-241751, 2001-319779 2001-319780, 2002-62824, 2002-100474, 2002-203679, 2002-343572, 2002-20 No. 3678.

 [0078] Some of the specific examples are shown below.

[0079] [Chemical 8]

[0081] [Chemical 10] Pt— 2

[0082] (Light-emitting host)

 A light-emitting host (also simply referred to as a host) means the compound with the highest mixing ratio (mass) in a light-emitting layer composed of two or more compounds, and other compounds It is called “Dopan Pantoy compound (also simply called dopant)”. For example, if the light emitting layer is composed of two types of compound A and compound B and the mixing ratio is A: B = 10: 90, compound A is a dopant compound and compound B is a host compound. Furthermore, if the light emitting layer is composed of three types of compound A, compound B, and compound C, and the mixing ratio is 8: 8: ○ = 5: 10: 85, compound A and compound B are dopant compounds. Compound C is a host compound.

[0083] As the luminescent host used in the present invention, phosphorescence of the luminescent dopant used in combination is 0-0 bar. When a compound containing a blue light-emitting component whose phosphorescence 0-0 band is 480 nm or less is used as a preferred light-emitting dopant, a compound having a phosphorescence 0-0 band with a wavelength shorter than that of Preferably, the phosphorescence 0-0 band is 450 nm or less.

 [0084] The light-emitting host according to the present invention is not particularly limited in terms of structure, but is typically a carbazole derivative, a triarylamine derivative, an aromatic borane derivative, a nitrogen-containing heterocyclic compound, thiophene. Preferred compounds include those having a basic skeleton such as derivatives, furan derivatives, and oligoarylene compounds, and having the 0_0 band of 450 nm or less. In addition, the light emitting host according to the present invention may be a low molecular compound, a high molecular compound having a repeating unit, or a low molecular compound having a polymerizable group such as a vinyl group or an epoxy group (evaporation polymerizable light emitting host). Good.

 [0085] As the light-emitting host, a compound that has a hole transporting ability and an electron transporting ability, prevents an increase in the wavelength of light emission, and has a high Tg (glass transition temperature) is preferable.

 [0086] As specific examples of the luminescent host, compounds described in the following documents are suitable.

 For example, JP 2001-257076, 2002-308855, 2001-313 179, 2002-319491, 2001-357977, 2002-3 34786, 2002- 8860, 2002-334787, 2002-1 5871, 2002-334788, 2002-43056, 2002-3 34789, 2002-75645, 2002 -338579, 2002-105445, 2002-343568, 2002-141173, 2002-352957, 2002-203683, 2002-363227, 20

02-231453, 2003-3165, 2002-234888, 20

03-27048, 2002-255934, 2002-260861, 2002-280183, 2002-299060, 2002-302516, 2002-305083, 2002-305084, 2002-308837, etc.

 Next, the configuration of a typical organic EL element will be described.

[0088] [Constitutional layer of organic EL element]

Preferred specific examples of the layer structure of the organic EL device of the present invention are shown below. It is not limited to it. (1) Anode / light emitting layer / electron transport layer / cathode (2) Anode / hole transport layer / light emitting layer / electron transport layer / cathode (3) Anode / hole transport layer / light emitting layer / hole blocking layer / electric Child transport layer / cathode (4) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode buffer layer / cathode (5) anode / anode buffer layer / hole transport layer / light emitting layer / Hole blocking layer / electron transport layer / cathode buffer layer / cathode

 [Light emitting layer]

 In the present invention, the organic EL device material is preferably used for the light emitting layer, but in addition to these materials, the above known light emitting host and light emitting dopant may be used in combination.

 [0089] Here, from the viewpoint of further improving the effect of the present invention, the light emitting layer preferably contains a compound represented by the general formula (2). These compounds are preferably used as a light emitting host in the light emitting layer.

 [0090] In the general formula (2), Z is an element forming an aromatic heterocyclic ring which may have a substituent.

 1

 And z represents an aromatic heterocyclic ring or an aromatic hydrocarbon ring which may have a substituent.

 2

 Represents a group of atoms, and Z represents a divalent linking group or a simple bond. R is a hydrogen atom

 3 4

 Or represents a substituent.

 [0091] Examples of the aromatic heterocycle represented by the atomic group of Z and Z include a furan ring, a thiophene ring, and a pyri ring.

 1 2

 Gin ring, pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring, benzimidazole ring, oxadiazole ring, triazole ring, imidazole ring, pyrazole ring, thiazole ring, indole ring, benzimidazole ring, benzothiazole ring, benzoxazole ring Quinoxaline ring, quinazoline ring, phthalazine ring, force rubazole ring, carboline ring, diaza force rubazole ring (indicates a ring in which one of the carbon atoms of the hydrocarbon ring constituting the carboline ring is further substituted with a nitrogen atom), etc. Is mentioned. Further, the aromatic heterocycle may have a substituent represented by R described later.

 41

 [0092] The aromatic hydrocarbon ring represented by the atomic group of Z includes a benzene ring, a biphenyl ring,

 2

Naphthalene ring, azulene ring, anthracene ring, phenanthrene ring, pyrene ring, talycene ring, naphthacene ring, triphenylene ring, o _ terphenyl ring, m-terphenyl ring, p _tenolephenyl ring, acenaphthene ring, coronene ring, fluorene ring , Fluoranthrene ring, naphthacene ring, pentacene ring, perylene ring, pentaphen ring, picene ring, pyrene ring, pyranthrene Ring, anthraanthrene ring and the like. Further, the aromatic hydrocarbon ring may have a substituent represented by R described later.

 Four

 Examples of the substituent represented by R include an alkyl group (for example, methyl group, ethyl group, propyl group).

Four

Group, isopropyl group, tert_butyl group, pentyl group, hexyl group, octyl group, dodecyl group, tridecinole group, tetradecinole group, pentadecinole group, etc.), cycloalkyl group (eg, cyclopentyl group, cyclohexyl group, etc.) An alkenyl group (for example, a buyl group, an aranole group, etc.), an alkynyl group (for example, an ethur group, a propargyl group, etc.), an allyl group (for example, a phenyl group, a naphthyl group, etc.), Furyl group, chenyl group, pyridinole group, pyridazinyl group, pyrimidinyl group, pyraduryl group, triazinyl group, imidazolinole group, pyrazolyl group, thiazolyl group, quinazolinyl group, phthaladyl group, etc.), heterocyclic group (for example, pyrrolidyl group, imidazolidyl group) Group, morpholyl group, oxazolidyl group, etc.), alkoxyl group (ex. For example, a methoxy group, an ethoxy group, a propyloxy group, a pentyloxy group, a hexinoreoxy group, an octyloxy group, a dodecinoreoxy group, etc.), a cycloalkoxynole group (for example, a cyclopentyloxy group, a cyclohexyloxy group, etc.), an aryloxy group ( For example, phenoxy group, naphthyloxy group, etc.), alkylthio group (for example, methylthio group, ethylthio group, propylthio group, pentylthio group, hexylthio group, octylthio group, dodecylthio group, etc.), cycloalkylthio group (for example, cyclopentylthio group) , Cyclohexylthio group, etc.), arylthio group (eg, phenylthio group, naphthylthio group, etc.), alkoxycarbonyl group (eg, methyloxycarbonyl group, ethyloxycarbonyl group, butoxycarbonyl group, The Oxycarbonyl group, dodecyloxycarbonyl group, etc.), aryloxycarbonyl group (eg, phenyloxycarbonyl group, naphthyloxycarbonyl group, etc.), sulfamoyl group (eg, aminosulfonyl group, methylaminosulfonyl group, dimethyl) Aminosulfonyl group, butylaminosulfonyl group, hexylaminosulfonyl group, cyclohexylaminosulfonyl group, octylaminosulfonyl group, dodecylaminosulfonyl group, phenylaminosulfonyl group, naphthylaminosulfonyl group, 2_pyridylaminosulfonyl group, etc.) A acyl group (eg, acetyl group, ethylcarbonyl group, propylcarbonyl group, pentylcarbonyl group, cyclohexylcarbonyl group, octylcarbonyl group, 2-ethylhexylcarbonyl group) De de A silcarbonyl group, a phenylcarbonyl group, a naphthylcarbonyl group, a pyridylcarbonyl group, etc.), an acyloleoxy group (eg, acetyloxy group, ethylcarbonyloxy group, butylcarbonyloxy group, octylcarbonyloxy group, dodecylcarbonyl group) Oxy group, phenylcarbonyloxy group, etc.), amide group (for example, methylcarbonylamino group, ethylcarbonylamino group, dimethylcarbonylamino group, propylcarbonylamino group, pentylcarbonylamino group, cyclohexane) Hexylcarbonylamino groups, 2-ethynole hexylcarbonylamino groups, octylcarbonylamino groups, dodecylcarbonylamino groups, phenylcarbonylamino groups, naphthylcarbonylamino groups, etc.) , Aminocarbonyl group, Tyraminocarbonyl group, dimethylaminocarbonyl group, propylaminocarbonyl group, pentylaminocarbonyl group, cyclohexylamino force carbonyl group, octylaminocarbonyl group, 2_ethylhexylaminocarbonyl group, dodecylamino Carbonyl group, phenylaminocarbonyl group, naphthylaminocarbonyl group, 2-pyridinoreaminocarbonyl group, etc.), ureido group (for example, methenoureido group, ethylureido group, pentylureido group, cyclohexylureido group, Octylureido group, dodecinoureido group, phenylureido group naphthylureido group, 2-pyridinoreaminoureido group, etc., sulfier group (for example, methylsulfifer group, ethylsulfinyl group, butinourenorefinole group, cyclohexene) Xinoles Norefienol group, 2-ethynolehexinolesnorefienol group, dodecylsulfinyl group, phenylsulfinyl group, naphthylsulfinyl group, 2-pyridylsulfinyl group, etc.), alkylsulfonyl group (for example, methylsulfonyl group, ethylsulfonyl group) Butylsulfonyl group, cyclohexylsulfonyl group, 2-ethynolehexylsulfonyl group, dodecylsulfonyl group, etc.), arylsulfonyl group (eg phenylsulfonyl group, naphthylsulfonyl group, 2_pyridylsulfonyl group, etc.), amino Group (for example, amino group, ethylamino group, dimethylamino group, butylamino group, cyclopentynoleamino group, 2-ethylhexylamino group, dodecylamino group, anilino group, naphthylamino group, 2_pyridinoreamino group, etc.), no, logogen (For example, fluorine atom, chlorine atom, bromine atom), fluorinated hydrocarbon group (for example, fluoromethyl group, trifluoromethyl group, pentafluoroethyl group, pentafluorophenyl group, etc.), cyano group, nitro group, Hydroxyl group, mercapto group, silyl group (for example, trimethylsilyl group, triisopropylpropyl group, A phenylsilyl group, a phenyljetylsilyl group, etc.).

 [0094] These substituents may be further substituted with the above substituents. In addition, a plurality of these substituents may be bonded to each other to form a ring. Preferred substituents are an alkyl group, a cycloalkyl group, a fluorinated hydrocarbon group, an aryl group, and an aromatic heterocyclic group.

 [0095] The divalent linking group may be a hydrocarbon group such as alkylene, alkenylene, alkynylene, arylene, etc., or may contain a heteroatom, and thiophene _ 2,5-diyl group may be pyrazine. 1 It may be a divalent linking group derived from a compound having an aromatic heterocycle such as a 2,3-diyl group (also referred to as a heteroaromatic compound), or it may be a force lucogen atom such as oxygen or sulfur. It ’s okay. In addition, a hetero atom such as an anolequinolemino group, a dialkylsilane diyl group or a diarylgermandyl group may be linked to meet each other.

[0096] The simple bond is a bond that directly bonds the connecting substituents together.

[0097] In the present invention, the ring formed by Z in the general formula (2) is preferably a 6-membered ring.

 1

 Les. Thereby, luminous efficiency can be made higher. In the present invention, z is

 2 The ring to be formed is preferably a 6-membered ring. Thereby, the luminous efficiency can be further increased. Furthermore, if both Z and Z are 6-membered rings, the luminous efficiency can be further increased.

 1 2

 Therefore, it is preferable.

 [0098] Specific examples of the compound represented by the general formula (2) according to the present invention are shown below, but the present invention is not limited thereto.

[0099] [Chemical 11]

Central skeleton

12] Compound .Φ heart skeleton A

13]

[0102] [Chemical 14]

[0103] [Chemical 15] Compound central urn

16]

[0105] [Chemical 17] Compound Central skeleton A

18]

[0107] [Chemical 19]

[0108] [Chemical 20]

[0109] [Chemical 21]

ZZ ^ [OIIO]

Z90l70C / 900Zdf / X3d 6S 888001/9001; OAV

[0111] [Chemical 23]

[0112] [Chemical 24]

OAV Ġ

[0114] [Chemical 26]

[0115] [Chemical 27]

[0117] [Chemical 29]

[0118] [Chemical 30]

[0119] [Chemical 31]

[0120] [Chemical 32]

[0121] [Chemical 33]

[0122] [Chemical 34]

[0123] [Chemical 35]

[0124] [Chemical 36]

[0125] [Chemical 37]

147

39]

[0128] [Chemical 40]

[0130] [Chemical 42]

[0132] [Chemical 44]

[0133] [Chemical 45]

The light emitting layer according to the present invention can be formed by forming the above compound by a known thinning method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. The thickness of the light emitting layer is not particularly limited, but is usually selected in the range of 5 nm to 5 m. This light emitting layer may have a single layer structure composed of one or two or more of these light emitting materials, or may have a laminated structure composed of a plurality of layers having the same composition or different compositions. [0135] Further, as described in JP-A-57-51781, this light-emitting layer is made into a solution by dissolving the above light-emitting material in a solvent together with a binder such as a resin, and then spinning it. It can be formed as a thin film by a coating method or the like. The film thickness of the light emitting layer formed in this manner can be appropriately selected depending on the situation where there is no particular limitation, but is usually in the range of 5 nm to 5 μm.

 [Blocking layer (hole blocking layer, electron blocking layer)]

 The blocking layer (for example, hole blocking layer, electron blocking layer) according to the present invention will be described. The thickness of the blocking layer according to the present invention is preferably 3 to:! OOnm, more preferably 5 to 30 nm.

 [0137] (Hole blocking layer)

 The hole blocking layer has a function of an electron transport layer in a broad sense, and is made of a material that has a function of transporting electrons and has a very small ability to transport holes, and blocks holes while transporting electrons. By doing so, the probability of recombination of electrons and holes can be improved.

 In the present invention, the organic EL device material of the present invention can be preferably used for the hole blocking layer in an adjacent layer adjacent to the light emitting layer, for example, a hole blocking layer, an electron blocking layer and the like.

 [0139] Examples of the hole blocking layer include those disclosed in JP-A-11-204258, JP-A-11204359, and “OLED device and its forefront of industrialization” (November 30, 1998, NTS). The hole blocking (hole blocking) layer described on page 237 of “Issued by the company” can be used as the hole blocking layer according to the present invention. Moreover, the structure of the electron carrying layer mentioned later can be used as a hole-blocking layer concerning this invention as needed.

 [0140] The hole blocking layer according to the present invention preferably contains the compound represented by the general formula (2). The hole blocking layer according to the present invention preferably contains a boron derivative.

 [0141] (Electron blocking layer)

On the other hand, the electron blocking layer has a function of a hole transport layer in a broad sense, and is made of a material having a function of transporting holes and an extremely small capacity of transporting electrons. The probability of recombination of electrons and holes can be improved by blocking the children. Moreover, the structure of the positive hole transport layer mentioned later can be used as an electron blocking layer as needed. [0142] In the present invention, it is preferable to use the organic EL device material of the present invention described above for the adjacent layer adjacent to the light emitting layer, that is, the hole blocking layer and the electron blocking layer. It is preferable to use it for the layer.

[Hole transport layer]

 The hole transport layer includes a material having a function of transporting holes, and in a broad sense, a hole injection layer and an electron blocking layer are also included in the hole transport layer. The hole transport layer can be provided as a single layer or a plurality of layers.

 [0144] There are no particular restrictions on the hole transport material. Conventionally, in photoconductive materials, it is commonly used as a hole charge injection / transport material, and used in the hole injection layer and hole transport layer of EL devices. Any known medium force can be selected and used.

 [0145] The hole transport material has either a hole injection or transport or electron barrier property, and may be either an organic or inorganic substance. 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, styrylanthracene derivatives, fluorenone derivatives, hydrazones Derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.

 [0146] The ability to use the above-mentioned materials as the hole transport material. It is preferable to use a porphyrin compound, an aromatic tertiary amine compound, and a styrylamine compound, particularly an aromatic tertiary amine compound.

[0147] Typical examples of aromatic tertiary amine compounds and styrylamine compounds include N, N, N ', N ^r —tetraphenyl _4, 4 ^; — diaminophenyl; Ν, Ν' — diphenylenole _Ν, Ν '— Bis (3-methylphenyl) -1- [1,1'-biphenyl] -1,4-diamine (TPD); 2, 2 _bis (4-di-ρ-tolylaminophenyl) propane; 1, 1 _Bis (4_di__trilaminophenyl) cyclohexane; Ν, Ν, Ν ', N ^r —tetra-p-tolyl-1,4′-diaminobiphenyl; 1,1-bis (4-di-one) p-tolylaminophenyl) 1-4-phenyl mouth hexane; bis (4-dimethylamino-2-methylphenyl) phenylmethane; bis (4-di-p-tolylaminophenyl) phenylmethane; N, N '— Gifu Ninore N, N '— Di (4— Methoxyphenyl) 1,4,1 diaminobiphenyl; N, N,, Ν '—tetraphenyl — 4, 4' —diaminodiphenyl ether; 4, 1 bis (diphenylamino) quadophenyl; Ν, Ν, Ν —Tri (ρ-tolyl) amine; 4— (Di-ρ-tolylamino) — — [4— (Di_ρ-tolylamino) styryl] stilbene; 4 _ Ν, Ν-diphenylamino (2-diphenyl) benzene 3-methoxy-1 4′_Ν, Ν-diphenylaminostilbenzene; Ν-vinylcarbazole, and two condensed aromatics described in US Pat. No. 5,061,569 Having a hydrocarbon ring in the molecule, for example, triphenylamine described in 4,1bis [Ν- (1-naphthyl) _Ν_phenylamino] biphenyl (NPD), JP-A-4-308688 3 units Starverse 4,, "-tris [1 ^-(3-methylphenyl) -l-phenylamino] triphenylamine (MTDATA), etc., linked in a to-type form.

 [0148] Furthermore, a polymer material in which these materials are introduced into a polymer chain or these materials as a polymer main chain can also be used. Inorganic compounds such as ρ-type-Si and p-type-SiC can also be used as the hole injection material and the hole transport material. In the present invention, the hole transport material of the hole transport layer preferably has a fluorescence maximum wavelength of 415 nm or less, and more preferably has a 0-0 band of phosphorescence of 450 nm or less. Also, the hole transport material is preferably high Tg.

 [0149] The hole transport layer is formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, an ink jet method, or an LB method. That power S. The thickness of the hole transport layer is not particularly limited, but is usually about 5 to 5000 nm. The hole transport layer may have a single layer structure composed of one or more of the above materials.

 [0150] [Electron transport layer]

 The electron transport layer is made of a material having a function of transporting electrons, and in a broad sense, an electron injection layer and a hole blocking layer are also included in the electron transport layer. The electron transport layer can be provided with a single layer or multiple layers.

[0151] Conventionally, when a single electron transport layer and a plurality of layers are used, an electron transport material (also serving as a hole blocking material) used for an electron transport layer adjacent to the light emitting layer on the cathode side is used. ,under The following materials are known. Further, the electron transport layer only needs to have a function of transferring electrons injected from the cathode to the light emitting layer, and any material of any conventionally known compound can be selected and used. .

 [0152] Examples of materials used for this electron transport layer (hereinafter referred to as electron transport materials) include heterocyclic tetrafluoride derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, naphthalene perylene, and other heterocyclic tetra Examples thereof include carboxylic acid anhydrides, force-repository imides, fluorenylidene methane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives, and the like. Furthermore, in the above oxadiazole derivative, a thiadiazole derivative in which the oxygen atom of the oxadiazole 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 an electron transport material.

 [0153] Furthermore, a polymer material in which these materials are introduced into a polymer chain or these materials as a polymer main chain can also be used.

[0154] In addition, metal complexes of 8 quinolinol derivatives such as tris (8 quinolinol) aluminum (Alq), tris (5,7-dichloro-1-8-quinolinol) aluminum, tris (5,7-dib mouth mode) 8 quinolinol) aluminum, tris (2methyl 8quinolinol) aluminum, tris (5-methyl 8-quinolinol) aluminum, bis (8-quinolinol) zinc (Zn q), etc., and the central metal of these metal complexes is In, Metal complexes replacing Mg, Cu, Ca, Sn, Ga or Pb can also be used as electron transport materials. In addition, metal free or metal phthalocyanine, or those having terminal ends substituted with an alkyl group or a sulfonic acid group can be preferably used as the electron transporting material. In addition, the distyrylvirazine derivative exemplified as the material for the light-emitting layer can also be used as an electron transport material, and, like the hole injection layer and the hole transport layer, n-type Si, _n- type SiC, etc. Inorganic semiconductors can also be used as electron transport materials.

[0155] This electron transport layer can be formed by thinning the electron transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, an ink jet method, or an LB method. S can. Although there is no restriction | limiting in particular about the film thickness of an electron carrying layer, Usually, it is about 5-5000 nm. This electron transport layer has a single layer structure composed of one or more of the above materials. It may be made.

 Next, an injection layer used as a constituent layer of the organic EL element of the present invention will be described.

[Injection layer (electron injection layer, hole injection layer)]

 The injection layer is provided as necessary, and has an electron injection layer and a hole injection layer, and as described above, exists between the anode and the light emitting layer or hole transport layer and between the cathode and the light emitting layer or electron transport layer. May be.

 [0158] The injection layer is a layer provided between the electrode and the organic layer in order to lower the driving voltage and improve the luminance of the light emission. “The organic EL element and the forefront of industrialization (November 30, 1998, NTT) 2) Chapter 2 “Electrode Materials” (pages 123 to 166) of “The Company”), the hole injection layer (anode buffer layer) and the electron injection layer (cathode buffer layer). There is.

 [0159] The details of the anode buffer layer (hole injection layer) are described in JP-A-9-45479, JP-A-9-260062, JP-A-8-288069 and the like. One layer of phthalocyanine buffer typified by copper phthalocyanine, one layer of oxide buffer typified by vanadium oxide, one layer of amorphous carbon buffer, one layer of polymer buffer using a conductive polymer such as polyaniline (emeraldine) or polythiophene, etc. Can be mentioned

[0160] The details of the cathode buffer layer (electron injection layer) are described in JP-A-6-325871, JP-A-917574, JP-A-10-74586, and the like. Specifically, strontium Metal buffer layer typified by aluminum, alkali metal compound buffer layer typified by lithium fluoride, alkaline earth metal compound buffer layer typified by magnesium fluoride, oxide buffer layer typified by aluminum oxide Etc.

 [0161] The buffer layer (injection layer) preferably has a very thin film thickness, although the film thickness is preferably in the range of 0.1 to: OOnm.

[0162] This injection layer can be formed by thin-filming the above material by a known method such as a vacuum deposition method, a spin coating method, a casting method, an ink jet method, or an LB method. The thickness of the injection layer is not particularly limited, but is usually about 5 to 5000 nm. This The injection layer may have a single layer structure composed of one or more of the above materials.

 [0163] [Anode]

 As the anode of the organic EL device of the present invention, an electrode material made of a metal, an alloy, an electrically conductive compound or a mixture thereof having a high work function (4 eV or more) is preferably used. Specific examples of such electrode materials include metals such as Au, and conductive transparent materials such as Cul, indium tin oxide (ITO), SnO, and ZnO. IDIX〇 (In〇

 2 2 3

A material such as _ZnO) that is amorphous and capable of producing a transparent conductive film may be used. For the anode, these electrode materials can be formed into a thin film by vapor deposition or sputtering, and a pattern of the desired shape can be formed by photolithography, or when the pattern accuracy is not so high (100 μm As described above, a pattern may be formed through a mask having a desired shape when the electrode material is deposited or sputtered. In the case of taking out light emission from this anode, it is desirable to have a transmittance of more than 10%, and the sheet resistance as the anode is preferably several hundred Ω / mouth or less. Further, the film thickness is a force depending on the material. Usually, 10 to 1000 nm, preferably 10 to 200 nm is selected.

[0164] [Cathode]

 On the other hand, as the cathode according to the present invention, a material having a low work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof is used. Specific examples of such electrode materials include sodium, sodium isotropic lithium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al O) mixture, indium, lithium / aluminum mixture, dilute

 twenty three

 Examples include earth metals. Among these, from the viewpoint of electron injectability and durability against oxidation, etc., a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function value than this, for example, a magnesium Z silver mixture , Magnesium Z aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O) mixture

2 3 compounds, lithium / aluminum mixtures, aluminum and the like are preferred. The cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. In addition, the sheet resistance as a cathode is several hundred Ω. Usually 10 to: 1000 nm, preferably 50 to 200 nm. In order to transmit light, it is convenient that either the anode or the cathode of the organic EL element is transparent or translucent to improve the light emission luminance.

[Substrate (also referred to as substrate, substrate, support, etc.)]

 The substrate of the organic EL device of the present invention is not particularly limited as long as it is transparent or transparent, and there are no particular restrictions on the type of glass, plastic, etc. Examples of substrates that are preferably used include glass, Examples thereof include quartz and a light-transmitting resin film. A particularly preferred substrate is a resin film that can give flexibility to the organic EL element.

 [0166] Examples of the resin film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyether ether ketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate ( PC), cellulose triacetate (TAC), cellulose acetate propionate (CAP) and the like.

[0167] The surface of the resin film may have an inorganic or organic coating or a hybrid coating of both, and the water vapor permeability is 0.01 g / m ² 'day' atm or less. It is preferred to be a film.

 [0168] The external extraction quantum efficiency at room temperature of light emission of the organic EL device of the present invention is preferably 1% or more, more preferably 2% or more. Here, the external extraction quantum efficiency (%) = the number of photons emitted to the outside of the organic EL element / the number of electrons flowed to the organic EL element × 100.

 [0169] Further, a hue improving filter such as a color filter may be used in combination.

 [0170] When used for illumination, a roughened film (such as anti-glare phenol) may be used in combination in order to reduce unevenness in light emission.

[0171] When used as a multicolor display device, it is composed of at least two types of organic EL elements having different light emission maximum wavelengths. A preferred example of producing an organic EL element will be described.

[Method of manufacturing organic EL element]

As an example of a method for producing the organic EL device of the present invention, an anode Z hole injection layer Z hole transport layer A method for producing an organic EL device composed of / luminescent layer / hole blocking layer / electron transport layer / cathode buffer layer / cathode will be described.

[0173] First, a desired electrode material, for example, a thin film made of an anode material is formed on a suitable substrate by a method such as vapor deposition or sputtering so as to have a thickness of 1 μm or less, preferably 10 to 200 nm. To produce an anode. Next, a thin film containing an organic compound such as a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, or an electron transport layer, which is an element material, is formed thereon.

[0174] As described above, there are spin coating method, casting method, ink jet method, vapor deposition method, printing method and the like as a method for thinning the thin film containing the organic compound, but it is easy to obtain a homogeneous film. The vacuum deposition method or the spin coating method is particularly preferable from the viewpoint of difficulty in generating pinholes. Further, different film forming methods may be applied for each layer. If you use the film adopts the deposition, the deposition conditions vary due to kinds of materials used, generally baud solved卩熱temperature 50 to 450 ° C, vacuum degree of 10- ⁶ ~: 10- ² Pa Desirably, the deposition rate is 0.01 to 50 nm / second, the substrate temperature is 50 to 300 ° C., and the film thickness is 0.1 nm to 5 / im.

 [0175] After these layers are formed, a thin film made of a cathode material is formed thereon by a method such as vapor deposition or sputtering so that the film thickness is 1 β m or less, preferably in the range of 50 to 200 nm. The desired organic EL device can be obtained by forming the cathode and providing a cathode. The organic EL element is preferably manufactured from the hole injection layer to the cathode consistently by a single evacuation, but it may be taken out halfway and subjected to different film forming methods. At that time, it is necessary to consider that the work is performed in a dry inert gas atmosphere.

 [Display device]

 The display device of the present invention will be described.

 [0177] The display device of the present invention may be monochromatic or multicolor, but here, a multicolor display device will be described. In the case of a multicolor display device, a shadow mask is provided only at the time of forming a light emitting layer, and a film can be formed on one surface by a vapor deposition method, a casting method, a spin coating method, an ink jet method, a printing method, or the like.

[0178] When patterning is performed only on the light emitting layer, the method is not limited, but the vapor deposition method, the ink jet method, and the printing method are preferable. When using a vapor deposition method, use a shadow mask, and use a patterning plate. [0179] Further, the order of preparation may be reversed, and the cathode, the electron transport layer, the hole blocking layer, the light emitting layer, the hole transport layer, and the anode may be formed in this order.

 [0180] When a DC voltage is applied to the multicolor display device thus obtained, light emission can be observed by applying a voltage of about 2 to 40 V with the positive polarity of the anode and the negative polarity of the cathode. In addition, even if a voltage is applied with the opposite polarity, no current flows and no light is emitted. In addition, when an AC voltage is applied, light is emitted only when the anode is in the ten state and the cathode is in the negative state. The AC waveform to be applied is arbitrary.

 [0181] The multicolor display device can be used as a display device, a display, and various light sources. Full color display is possible by using three types of organic EL elements, blue, red, and green, for display devices and displays.

 [0182] Display devices and displays include TVs, personal computers, mopile devices, AV devices, text broadcast displays, information displays in automobiles, and the like. In particular, the driving method when used as a display device for reproducing moving images, which may be used as a display device for reproducing still images or moving images, may be either a simple matrix (passive matrix) method or an active matrix method.

 [0183] Light emitting sources include home lighting, interior lighting, clock and liquid crystal backlights, billboard advertisements, traffic lights, light sources for optical storage media, light sources for electrophotographic copying machines, light sources for optical communication processors, light sensors Although a light source etc. are mentioned, it is not limited to this.

 [0184] [Lighting device]

 The lighting device of the present invention will be described.

 [0185] The organic EL element having a resonator structure may be used as an organic EL element having a resonator structure in the organic EL element of the present invention. Examples include, but are not limited to, light sources for electrophotographic copying machines, light sources for optical communication processors, light sources for optical sensors, and the like. Further, it may be used for the above application by causing laser oscillation.

[0186] Further, the organic EL device of the present invention may be used as a kind of lamp such as an illumination or exposure light source, a projection device of a type for projecting an image, a still image or a moving image. It may be used as a type of display device (display) that is directly visible. For video playback When used as a display device, the driving method may be either a simple matrix (passive matrix) method or an active matrix method. Alternatively, a full color display device can be produced by using two or more organic EL elements of the present invention having different emission colors.

 An example of a display device composed of the organic EL element of the present invention will be described with reference to the drawings.

[0188] FIG. 1 is a schematic view showing an example of a display device composed of organic EL elements. FIG. 2 is a schematic diagram of a display such as a mobile phone that displays image information by light emission of an organic EL element.

 [0189] The display 1 includes a display unit A having a plurality of pixels, a control unit B that performs image staging of the display unit A based on image information, and the like.

[0190] The control unit B is electrically connected to the display unit A, and sends a scanning signal and an image data signal to each of a plurality of pixels based on image information from the outside. The image information is displayed by sequentially emitting light according to the image data signal and displaying the image information.

Display on A.

FIG. 2 is a schematic diagram of the display unit A.

 The display unit A has a wiring unit including a plurality of scanning lines 5 and data lines 6, a plurality of pixels 3 and the like on a substrate. 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 direction of the white arrow (downward).

 [0193] 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 lines 5 and the data lines 6 are orthogonal to each other in a grid pattern and are connected to the pixels 3 at the orthogonal positions. (The details are not shown).

 [0194] When a scanning signal is applied from the scanning line 5, the pixel 3 receives an image data signal from the data line 6 and emits light in accordance with the received image data. Full color display is possible by appropriately arranging pixels in the red region, the green region, and the blue region on the same substrate.

 [0195] Next, the light emission process of the pixel will be described.

FIG. 3 is a schematic diagram of a pixel. [0197] The pixel includes an organic EL element 10, a switching transistor 11, a driving transistor 12, a capacitor 13, and the like. Full-color display can be performed by using organic EL elements of red, green, and blue light emission as organic EL elements 10 in a plurality of pixels and arranging them on the same substrate.

 In FIG. 3, an image data signal is applied from the control unit B to the drain of the switching transistor 11 via the data line 6. When a stray 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 driven by the capacitor 13. It is transmitted to the gate of transistor 12.

 By transmitting the image data signal, the capacitor 13 is charged according to the potential of the image data signal, and the drive of the drive transistor 12 is turned on. The drive transistor 12 has a drain connected to the power supply line 7 and a source connected to the electrode of the organic EL element 10, and the organic EL element is connected from the power supply line 7 according to the potential of the image data signal applied to the gate. Current is supplied to element 10.

 When the scanning signal is moved to the next scanning line 5 by the sequential scanning of the control unit B, the driving of the switching transistor 11 is turned off. However, even if the driving of the switching transistor 11 is turned off, the capacitor 13 holds the potential of the charged image data signal, so that the driving of the driving transistor 12 is kept on and the next scanning signal is applied. The organic EL device 10 continues to emit light until it is seen. When a scanning signal is next applied by sequential scanning, 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.

 That is, the organic EL element 10 emits light by providing a switching transistor 11 and a driving transistor 12 as active elements for each of the organic EL elements 10 of each of the plurality of pixels. Element 10 is emitting light. Such a light emitting method is called an active matrix method.

[0202] Here, the light emission of the organic EL element 10 may be light emission of a plurality of gradations by a multi-value image data signal having a plurality of gradation potentials, or a predetermined light emission amount of the binary image data signal. It may be on or off. [0203] Also, the potential of the capacitor 13 can be maintained until the next scanning signal is applied, or can be discharged immediately before the next scanning signal is applied.

[0204] In the present invention, not only the active matrix method described above, but also a passive matrix light emission drive in which the organic EL element emits light according to the data signal only when the scanning signal is scanned.

FIG. 4 is a schematic diagram of a display device using a passive matrix method. In FIG. 4, 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.

 [0206] When the scanning signal of the scanning line 5 is applied by sequential scanning, the pixel 3 connected to the applied scanning line 5 emits light according to the image data signal. The passive matrix method can reduce the manufacturing cost of an active element in addition to pixel 3.

 [0207] The organic EL material according to the present invention can also be applied to an organic EL element that emits substantially white light as a lighting device. A plurality of light emitting colors are simultaneously emitted by a plurality of light emitting materials to obtain white light emission by mixing colors. The combination of multiple emission colors may include the three maximum emission wavelengths of the three primary colors of blue, green, and blue, and it uses the relationship of complementary colors such as blue and yellow, and blue-green and orange 2 It may be one containing two emission maximum wavelengths.

 [0208] In addition, a combination of light emitting materials for obtaining a plurality of emission colors includes a combination of a plurality of phosphorescent or fluorescent materials (light emitting dopants), a light emitting material that emits fluorescent or phosphorescent light, and A combination of a dye material that emits light of the light emitting material power as excitation light may be misaligned. However, the white organic EL element according to the present invention may be combined with a plurality of light emitting dopants. Is preferred.

 [0209] The layer structure of the organic EL device for obtaining a plurality of emission colors includes a method in which a plurality of emission dopants exist in one emission layer, a plurality of emission layers, and each emission layer includes Examples include a method in which dopants having different emission wavelengths are present, and a method in which minute pixels that emit light at different wavelengths are formed in a matrix.

[0210] In the white organic EL device according to the present invention, patterning may be performed by a metal mask or an ink jet printing method when forming a film, if necessary. When patterning, only the electrode may be patterned, or the electrode and the light emitting layer may be patterned. However, the entire layer of the element may be patterned.

 [0211] The light emitting material used for the light emitting layer is not particularly limited. For example, in the case of a backlight in a liquid crystal display element, the light emitting material according to the present invention is adapted so as to conform to the wavelength range corresponding to the CF (color filter) characteristics. Select a platinum complex or any of the known luminescent materials and combine them to make them white.

 [0212] Thus, in addition to the display device and the display, the white light-emitting organic EL element is used as various types of light sources, lighting devices, home lighting, interior lighting, and a kind of lamp such as an exposure light source. It is also useful for display devices such as backlights for liquid crystal display devices.

 [0213] Other light sources such as backlights for watches, billboard advertisements, traffic lights, optical storage media, light sources for electronic photocopiers, light sources for optical communication processors, light sources for optical sensors, etc. And a wide range of uses such as general household appliances.

 Example

 [0214] Hereinafter, the present invention will be described by way of examples, but the present invention is not limited thereto.

[0215] Example 1

 [Production of organic EL element 1]

 After patterning a substrate with 150nm ITO film on glass (NH Techno Glass: NA-45) as the anode, this transparent support substrate with ITO transparent electrode was ultrasonically cleaned with isopropyl alcohol Then, it was dried with dry nitrogen gas, and UV ozone cleaning was performed for 5 minutes. This transparent support substrate is fixed to the substrate holder of a commercially available vacuum deposition apparatus, while _NPD, CBP, Ir_ll, BCP, and Alq are placed in five resistance heating boats made of tantalum, respectively. It was attached to the first vacuum chamber.

[0216] Further, lithium fluoride was placed in a tantalum resistance heating boat, and aluminum was placed in a tungsten resistance heating boat, which were attached to the second vacuum chamber of the vacuum evaporation system.

[0217] First, after the vacuum of the first vacuum chamber to 4 X 10- ⁴ Pa, and heated by supplying an electric current to the baud preparative containing the shed NPD, deposition rate 0.:!~ 0. 2nm The film was deposited on the transparent support substrate at a film thickness of 25 nm per second, and a hole injection / transport layer was provided.

[0218] Furthermore, the heating boat containing CBP and the boat containing Ir 11 are independently energized, so that the deposition rate of CBP as the light emitting host and Ir-11 as the light emitting dopant is 100: 6. The light emitting layer was provided by vapor deposition so that the film thickness was adjusted to 30 nm.

[0219] Next, the heating boat containing BCP was energized and heated, and a hole blocking layer having a thickness of 10 nm was provided at a deposition rate of 0.0 :! to 0.2 nm / sec. Furthermore, the heated boat containing Alq

 Three

 An electron transport layer with a film thickness of 40 nm was provided at a deposition rate of 0 :! to 0.2 nm / sec.

[0220] Next, after the element formed up to the electron transport layer as described above is transferred to the second vacuum chamber while being vacuumed, a rectangular perforated mask made of stainless steel is placed on the electron transport layer. Equipment Remotely installed from outside.

[0221] After decompression of the second vacuum chamber up to 2 X 10- ⁴ Pa, evaporation Chakusokudo 0.01 to 0 by supplying an electric current to the boat of the lithium fluoride-containing. 02nm / sec to a film thickness 0. 5 nm cathode buffer One layer was provided, and then a boat with an anoromiumium was energized, and a cathode having a film thickness of 150 nm was attached at a deposition rate of 1 to 2 nm / second. Furthermore, this organic EL element was transferred to a glove box under nitrogen atmosphere (a glove box substituted with high-purity nitrogen gas with a purity of 99.999% or more) without being exposed to the atmosphere, and the interior as shown in Fig. 5 was filled with nitrogen. An organic EL element 1 was fabricated with a substituted sealing structure.

 [0222] Barium oxide 105, a water-absorbing agent, is made of Aldrich's high-purity barium oxide powder with a fluororesin-based semipermeable membrane (Microtex S-NTF8031Q made by Nitto Denko) with adhesive. What was affixed on the sealing can 104 was prepared in advance and used. An ultraviolet curable adhesive 107 was used to bond the sealing can and the organic EL element, and the sealing element was prepared by irradiating an ultraviolet lamp to bond them together.

 In FIG. 5, 101 is a glass substrate provided with a transparent electrode, 102 is an organic EL layer comprising the hole injection / transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, and the like, and 103 is a cathode.

 [Organic EL device 2 ~: Fabrication of 16]

 In the production of the organic EL element 1, as described in Table 1, organic EL elements 2 to 16 were produced in the same manner except that the light emitting host, the light emitting dopant and the hole blocking layer were changed.

[0225] [Chem 46]

 [0226] [Evaluation of organic EL devices]

 The produced organic EL device was evaluated as follows. The evaluation results are shown in Table 1.

 [0227] (External quantum efficiency)

With respect to the obtained organic EL device, the external extraction quantum efficiency (%) was measured when a constant current of ^2.5 mA / cm ² was applied at 23 ° C. in a dry nitrogen gas atmosphere. A spectral radiance meter CS-1000 (Konica Minolta Sensing) was used for the measurement. The quantum efficiency is expressed as a relative value when the organic EL element 1 is 100.

 [0228] (Luminescence lifetime)

The organic EL device was continuously lit at a constant current of ^2.5 mA / cm ² at room temperature, and the time ( _τ 1/9) required to reach ₉₀ % of the initial luminance was measured. Similarly, a spectral radiance meter CS-1000 (manufactured by Konica Minolta Sensing) was used for the measurement. The light emission lifetime is expressed as a relative value when the organic EL element 1 is 100.

[0229] [Table 1] Organic EL element Light emission Light emission Hole External extraction light emission

 Remarks

 No. Phosphine dopant blocking layer quantum efficiency lifetime

 1 CBP lr-11 BCP 100 100 Comparative example

2 CBP Pt- 2 BCP 90 74 Comparative example

3 CBP (1 1 1) BCP 118 122 The present invention

4 CBP (1 1 11) BCP 116 131 The present invention

5 CBP (2 -10) 74 125 120 The present invention

6 CBP (2-11) BCP 121 124 The present invention

7 CBP (3-7) BCP 116 119 The present invention

 Size

 8 CBP (ω3 -10) BCP 117 114 The present invention

9 CBP ω 38 122 129 The present invention

10 CBP (5-1) BCP 119 120 The present invention

11 CBP (5-5) BCP 120 127 The present invention

12 74 (1-6) 74 127 130 The present invention

13 74 (4-1) 74 126 128 The present invention

14 74 BCP 129 133 The present invention

15 74 74 137 138 The present invention

16 74 (5-4) 38 134 144 The present invention

17 74 74 141 139 The present invention

[0230] From Table 1, the organic EL device using the metal complex according to the present invention for the light-emitting layer is a comparative organic E element.

It is clear that the light emission efficiency is high and the light emission lifetime is long as compared with the L element. The general formula (

It can be seen that the quantum efficiency is further improved by using the compound represented by 2) in the light-emitting host and the Z or hole blocking layer.

 [0231] Example 2

 [Production of white organic EL elements by coating]

A direct current power supply was used on a glass support substrate of 25mm X 25mm XO.5mm, and an anode of indium tin oxide (ITO, indium / tin = 95/5 molar ratio) was formed by sputtering (thickness 200nm) . The surface resistance of this anode was 10 Ω / mouth. Polyvinylcarbazole (hole transporting binder polymer) / (3-12) / (4-11) / (4-3) / 2— (4-biphenylyl) -5 (4 t butylphenyl) -1,3,4-Oxadiazole (electron transport material) = 200/2/3/2/50 (mass ratio) prepared, dissolved dichloroethane solution was applied with a spin coater, lOOnm The light emitting layer was obtained. A buttered mask (a mask with a light emitting area of 5 mm x 5 mm) is placed on the organic compound layer, and the cathode mask is placed in the vapor deposition system. A cathode was provided by depositing lithium fluoride 0.5 nm as a fur layer and 150 nm of aluminum as a cathode. A light emitting element was manufactured by extending aluminum lead wires from the anode and the cathode, respectively. The light-emitting element was put in a glove box substituted with nitrogen gas, and sealed with a glass sealing container using an ultraviolet curable adhesive (XNR5493, manufactured by Chiba Nagase) to produce an organic EL element.

 [0232] When this organic EL element was energized, almost white light was obtained.

It was found that the organic EL element can be produced by coating the material for the L element.

[0233] Example 3

 [Production of full-color display device]

 (Production of blue light-emitting elements)

 The organic EL element 15 of Example 1 was used as a blue light emitting element.

[0234] (Production of green light-emitting element)

 The organic EL device 13 of Example 1 was used as a green light emitting device.

[0235] (Production of red light-emitting element)

 The organic EL element 14 of Example 1 was used as a red light emitting element.

[0236] Each of the red, green, and blue light emitting organic EL elements produced above is juxtaposed on the same substrate to produce an active matrix type full-color display device having the configuration shown in FIG. 1, and FIG. Only the schematic view of the display part A of the produced display device is shown. That is, on the same substrate, a wiring portion including a plurality of scanning lines 5 and data lines 6 and a plurality of juxtaposed pixels 3 (emission color is a red region pixel, a green region pixel, a blue region pixel, etc.) 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 lines 5 and the data lines 6 are orthogonal to each other in a grid pattern and are connected to the pixels 3 at the orthogonal positions. (Details not shown). The plurality of pixels 3 are driven by a formula that is an organic EL element and an active element corresponding to each emission color, and when a scanning signal is applied from the scanning line 5, the image data is transmitted from the data line 6. A signal is received, and light is emitted according to the received image data. Thus, a full-color display device was produced by juxtaposing the red, green, and blue pixels appropriately.

[0237] By driving this full-color display device, the luminance is high and the durability is high. It was found that a clear full-color moving image display can be obtained.

 [0238] Example 4

 [Production of white light-emitting element and white illumination device]

 The electrode of the transparent support substrate of Example 1 was patterned to 20 mm x 20 mm, and then a single NPD was formed to a thickness of 25 nm as a hole injection / transport layer in the same manner as in Example 1, The heating boat containing the compound 74, the boat containing the compound (1 1 1) and the boat containing the compound (2-10) are energized independently, respectively, A boat containing a compound (1 1 1) and a compound (2-10) were deposited so that the deposition rate was 10 0: 7: 1 and deposited to a thickness of 40 nm. Provided.

[0239] Next, BCP was deposited to a thickness of 10 nm to provide a hole blocking layer. In addition, Alq was deposited at 40 nm to provide an electron transport layer.

[0240] Next, as in Example 1, a square perforated mask having substantially the same shape as the transparent electrode made of stainless steel was placed on the electron transport layer, and lithium fluoride 0.5 nm and the cathode were formed as one cathode buffer layer. As a film, 150 nm of aluminum was deposited.

[0241] This element was equipped with a sealing can having the same method and the same structure as in Example 1 to produce a planar lamp. Figure 6 shows a schematic diagram of a flat lamp. Fig. 6 (a) shows a schematic plan view and Fig. 6 (b) shows a schematic cross-sectional view.

 [0242] When this flat lamp was energized, almost white light was obtained, and it was found that it could be used as a lighting device.

Claims

The scope of the claims

 A material for an organic EL device, which is a metal complex having a partial structure represented by the following general formula (1), wherein the ligand portion has at least one substituent that suppresses bidentate coordination.

'General Rejection'

 (In the formula, M is a metal atom, X, Y, and Ζ are constituents of ring Α, ring Β, and ring C, respectively, and are carbon atoms or nitrogen atoms, and at least one is a carbon atom, Ring Α, ring Β, and ring C are aromatic hydrocarbon rings, aromatic heterocycles or heterocycles R to R are substituents, and nl, n2, and n3 are 0 or positive L is an auxiliary arrangement

 13

 Represents a ligand, and m is an integer of 1 to 3. )

[2] In the general formula (1), at least one of the substituents R of ring B is bonded to ring A and ring C.

 2

No, van der Waals volume (VDW) is 45A ³ or higher alkyl group, cycloalkyl group, alkenyl group, alkynyl group, heterocyclic group, alkoxy group, cycloalkoxy group, snowfininore group, alkylsulfonyl group or silyl group 2. The material for an organic EL device according to claim 1, wherein the material is an organic EL device material.

 [3] An organic EL device comprising the organic EL device material according to claim 1 or 2 in one of the constituent layers forming the organic EL device.

 4. The organic EL device according to claim 3, wherein one of the constituent layers is a light emitting layer.

[5] The compound represented by the following general formula (2) is contained in at least one of the constituent layers. 5. The organic EL device according to claim 3 or 4, wherein

 [Chemical 2] — General formula ί

(In the formula, Z represents an atomic group forming an aromatic heterocycle, Z is an aromatic heterocycle or aromatic

 1 2

 Represents a group of atoms that form an aromatic hydrocarbon ring, and Z represents a divalent linking group or a simple bond.

 Three

 The R represents a hydrogen atom or a substituent. )

 Four

 [6] A display device comprising the organic EL element according to any one of claims 35 to 35.

 [7] An illuminating device comprising the organic EL element according to any one of claims 35.