JP5556602B2 - Material for organic electronics element, organic electronics element, lighting device and display device - Google Patents

Description

  The present invention relates to a material for an organic electronics element, an organic electronics element, a lighting device, and a display device, and more particularly to an organic electronics element and a compound that can be preferably used for the organic electronics element.

  In recent years, there has been great interest in so-called organic electronics materials based on organic semiconductors, as well as organic electronics elements using them. Examples of the organic electronics element include an organic electroluminescence (EL) element, an organic thin film solar cell, and an organic transistor. In general, organic electronics elements are light, thin, and flexible. In addition to dry (vacuum) processes such as vapor deposition that have been widely used in inorganic semiconductors, they also match with wet processes such as printing and coating film formation. Therefore, there is an expectation for large area and low price. On the other hand, compared to inorganic semiconductors, there is a problem in material stability, and development of new materials is awaited.

  For example, an organic EL element that has been attracting attention in recent years has a configuration in which a light emitting layer containing a light emitting compound is sandwiched between a cathode and an anode, and by injecting electrons and holes into the light emitting layer and recombining them. It is an element that generates excitons (excitons) and emits light using light emission (fluorescence / phosphorescence) when the excitons are deactivated. Light emission is possible at a voltage of several volts to several tens of volts, and since it is a self-luminous type, it has a wide viewing angle, and since it is a thin-film type completely solid element, it is very interesting from the viewpoint of space saving and portability. Collecting.

  As for development of organic EL elements for practical use, Princeton University has reported organic EL elements that use phosphorescence emission from excited triplets (see, for example, Non-Patent Document 1). Research on the materials shown has become active (see, for example, Patent Documents 1 and 2 and Non-Patent Document 2).

  In addition, recently discovered organic EL devices that use phosphorescence can realize a luminous efficiency that is approximately four times that of previous devices that use fluorescence. Research and development of light-emitting element layer configurations and electrodes are performed all over the world. For example, many compounds have been studied for synthesis centering on heavy metal complexes such as iridium complexes (see, for example, Non-Patent Document 3).

  Although this is a very high potential method, the organic EL device using phosphorescence emission is greatly different from the organic EL device using fluorescence emission, and the position of the emission center is controlled. The use of thermally and electrically stable materials that can recombine in order to stabilize light emission is an important technical issue in terms of capturing device efficiency and lifetime. .

US Pat. No. 6,097,147 JP 2005-112765 A

M.M. A. Baldo et al. , Nature, 395, 151-154 (1998) M.M. A. Baldo et al. , Nature, 403, 17, 750-753 (2000) S. Lamansky et al. , J .; Am. Chem. Soc. 123, 4304 (2001)

  The present invention has been made in view of the above problems, and its object is to provide an organic electronics element material, an organic electronics element, a display device, and a lighting device that have high luminous efficiency, long luminous lifetime, and low driving voltage. There is to do.

  The above object of the present invention can be achieved by the following configuration.

  1. The organic electronic device material used for the light emitting layer of the organic electronic device having at least an anode, an organic light emitting layer, and a cathode on the support substrate is a cyclic silicon compound represented by the following general formula (1). A characteristic material for organic electronics elements.

(Wherein X1 and X2 represent a substituted or unsubstituted arylene or heteroarylene group, and R _{1 to} R ₈ are a hydrogen atom, a halogen atom, a nitro group, a cyano group or a substituted, unsubstituted amino group, an alkyl group, Represents an alkoxy group, an aryl group, or a heteroaryl group.)
2. 2. The material for an organic electronic device as described in 1 above, wherein a band gap between the ground state and the triplet excited state of the cyclic silicon compound is 2.1 eV or more and 3.8 eV or less.

  3. 3. The material for an organic electronics element as described in 1 or 2 above, wherein a band gap between the ground state and the triplet excited state of the cyclic silicon compound is 2.7 eV or more and 3.8 eV or less.

  4). X1 or X2 of the general formula (1) is any one selected from the following general formulas (2) to (5): material.

(In the formula, two arbitrary hydrogen atoms are linking groups. Y _{1 to} Y ₅ represent NR, O, S, BR, CRR ′ or SiRR ′, and R and R ′ each represent a hydrogen atom or a substituent. Z _{1 to} Z ₁₀ each represent N or CR, and each R represents a hydrogen atom or a substituent, provided that at least one of Z _{1 to} Z ₁₀ is N).

  5. 5. An organic electronic device having at least an anode, a light emitting layer made of an organic substance, and a cathode on a support substrate, wherein the light emitting layer contains the material for an organic electronic device according to any one of 1 to 4 above. Organic electronics element.

  6). 6. The organic electronic device as described in 5 above, wherein the light emitting material contained in the light emitting layer is a phosphorescent material.

  7). 7. The organic electronic device as described in 6 above, wherein the phosphorescent material is an Ir complex.

  8). 8. The organic electronic device as described in 7 above, wherein the band gap between the ground state and triplet excited state of the Ir complex is 2.7 eV or more and 3.8 eV or less.

  9. 9. The organic electronics element as described in any one of 5 to 8 above, which emits white light.

  10. An illumination device comprising the organic electronic element according to any one of 5 to 9 above.

  11. A display device comprising the organic electronic element according to any one of 5 to 9 above.

  The organic electronics element material of the present invention can provide an organic electronics element that exhibits high emission luminance, has a long half-life, and has a low driving voltage, and an illumination device and a display device using the element.

It is the schematic diagram which showed an example of the display apparatus comprised from an organic EL element. 4 is a schematic diagram of a display unit A. FIG. It is a schematic diagram of a pixel. It is a schematic diagram of a passive matrix type full-color display device. It is the schematic of an illuminating device. It is a schematic diagram of an illuminating device. The schematic block diagram of an organic electroluminescent full color display apparatus is shown.

  The best mode for carrying out the present invention will be described in detail below, but the present invention is not limited thereto.

  The best mode for carrying out the present invention will be described in detail below, but the present invention is not limited thereto.

  As a result of intensive studies in view of the above-mentioned problems, the present inventors show high emission luminance by using at least one compound represented by the general formula (1), have a long half-life, and have a driving voltage of It has been found that a low organic EL element and an illumination device and a display device using the organic EL element can be provided, and the present invention has been achieved. For example, in the organic EL element which is an example of the organic electronics element of the present invention, all the characteristics of the external extraction quantum efficiency, the driving voltage, and the emission lifetime are improved as compared with the conventional case.

  Hereinafter, the best mode for carrying out the present invention will be described in detail, but the present invention is not limited thereto.

  The cyclic silicon compound represented by the general formula (1), which is a material for organic electronics elements of the present invention, will be described.

<< Cyclic silicon compound represented by general formula (1) >>
In the general formula (1), as the arylene groups represented by X1 and X2, respectively, o-phenylene group, m-phenylene group, p-phenylene group, naphthalenediyl group, anthracenediyl group, naphthacenediyl group, pentacenediyl group, Pyrenediyl group, naphthylnaphthalenediyl group, biphenyldiyl group (for example, [1,1′-biphenyl] -4,4′-diyl group, 3,3′-biphenyldiyl group, 3,6-biphenyldiyl group, etc.), Examples thereof include a terphenyldiyl group, a quaterphenyldiyl group, a kinkphenyldiyl group, a sexiphenyldiyl group, a septiphenyldiyl group, an octylphenyldiyl group, a nobiphenyldiyl group, and a deciphenyldiyl group.

  Further, the arylene group may further have a substituent described later.

  In the general formula (1), examples of the heteroarylene groups represented by X1 and X2 include a carbazole ring, a carboline ring, a diazacarbazole ring (also referred to as a monoazacarboline ring, one of carbon atoms constituting the carboline ring). Are substituted with a nitrogen atom), triazole ring, pyrrole ring, pyridine ring, pyrazine ring, quinoxaline ring, thiophene ring, oxadiazole ring, dibenzofuran ring, acridine ring, phenazine ring, dibenzothiophene ring, And divalent groups derived from the group consisting of indole rings.

  The heteroarylene group may further have a substituent described later.

  Specific examples of the arylene group or heteroarylene group represented by X1 and X2 in the general formula (1) are shown below, but the present invention is not limited thereto.

In the general formula (1), examples of the amino groups represented by R _{1 to} R ₈ include an amino group, an ethylamino group, a dimethylamino group, a butylamino group, a cyclopentylamino group, a 2-ethylhexylamino group, and dodecyl. An amino group, an anilino group, a naphthylamino group, a 2-pyridylamino group, etc. are mentioned.

In the general formula (1), examples of the alkyl group represented by each of R _{1 to} R ₈ include a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a hexyl group, an octyl group, A dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, etc. are mentioned. These groups may further have a substituent described later.

In the general formula (1), examples of the alkoxy group represented by R _{1 to} R ₈ include a methoxy group, an ethoxy group, a propyloxy group, a pentyloxy group, a hexyloxy group, an octyloxy group, and a dodecyloxy group. ), A cycloalkoxy group (for example, a cyclopentyloxy group, a cyclohexyloxy group, etc.).

  These groups may further have a substituent described later.

In the general formula (1), examples of the aromatic hydrocarbon ring group represented by each of R _{1 to} R ₈ include a phenyl group, a p-chlorophenyl group, a mesityl group, a tolyl group, a xylyl group, a naphthyl group, and an anthryl group. , Azulenyl group, acenaphthenyl group, fluorenyl group, phenanthryl group, indenyl group, pyrenyl group, biphenylyl group and the like. These groups may further have a substituent described later.

In the general formula (1), examples of the aromatic heterocyclic group represented by R _{1 to} R ₈ include a furyl group, a thienyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, and an imidazolyl group. , Pyrazolyl group, thiazolyl group, quinazolinyl group, carbazolyl group, carbolinyl group, diazacarbazolyl group (indicating that one of the carbon atoms constituting the carboline ring of the carbolinyl group is replaced by a nitrogen atom), quinoxalinyl Group, pyridazinyl group, triazinyl group, quinazolinyl group, phthalazinyl group and the like. These groups may further have a substituent described later.

In the general formula (1), examples of the substituent that each of the groups represented by X1, X2, and R _{1 to} R ₈ may further include an alkyl group (for example, a methyl group, an ethyl group, a propyl group, an isopropyl group). Tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, etc.), cycloalkyl group (for example, cyclopentyl group, cyclohexyl group, etc.), alkenyl group (for example, vinyl group) Allyl group, 1-propenyl group, 2-butenyl group, 1,3-butadienyl group, 2-pentenyl group, isopropenyl group, etc.), alkynyl group (for example, ethynyl group, propargyl group, etc.), aromatic hydrocarbon group (Aromatic hydrocarbon ring group, aromatic carbocyclic group, aryl group, etc., for example, phenyl group, p-chlorophenyl group, mesity Group, tolyl group, xylyl group, naphthyl group, anthryl group, azulenyl group, acenaphthenyl group, fluorenyl group, phenanthryl group, indenyl group, pyrenyl group, biphenylyl group, etc.), aromatic heterocyclic group (for example, furyl group, thienyl group) , Pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, quinazolinyl group, carbazolyl group, carbolinyl group, diazacarbazolyl group Any one of carbon atoms is replaced by a nitrogen atom), a phthalazinyl group, etc.), a heterocyclic group (eg, a pyrrolidyl group, an imidazolidyl group, a morpholyl group, an oxazolidyl group, etc.), an alkoxy group (eg, a methoxy group, Ethoxy group, propyloxy , Pentyloxy group, hexyloxy group, octyloxy group, dodecyloxy group, etc.), cycloalkoxy group (eg, cyclopentyloxy group, cyclohexyloxy group, etc.), aryloxy group (eg, phenoxy group, naphthyloxy group, etc.), An alkylthio group (eg, methylthio group, ethylthio group, propylthio group, pentylthio group, hexylthio group, octylthio group, dodecylthio group, etc.), cycloalkylthio group (eg, cyclopentylthio group, cyclohexylthio group, etc.), arylthio group (eg, phenylthio group) Group, naphthylthio group, etc.), alkoxycarbonyl group (eg, methyloxycarbonyl group, ethyloxycarbonyl group, butyloxycarbonyl group, octyloxycarbonyl group, dodecyloxycarbonyl group, etc.), Reeloxycarbonyl group (eg, phenyloxycarbonyl group, naphthyloxycarbonyl group, etc.), sulfamoyl group (eg, aminosulfonyl group, methylaminosulfonyl group, dimethylaminosulfonyl group, butylaminosulfonyl group, hexylaminosulfonyl group, cyclohexylamino) Sulfonyl group, octylaminosulfonyl group, dodecylaminosulfonyl group, phenylaminosulfonyl group, naphthylaminosulfonyl group, 2-pyridylaminosulfonyl group, etc.), acyl group (for example, acetyl group, ethylcarbonyl group, propylcarbonyl group, pentylcarbonyl group) Cyclohexylcarbonyl group, octylcarbonyl group, 2-ethylhexylcarbonyl group, dodecylcarbonyl group, phenylcarbonyl group, naphthylcarbonyl Group, pyridylcarbonyl group, etc.), acyloxy group (eg, acetyloxy group, ethylcarbonyloxy group, butylcarbonyloxy group, octylcarbonyloxy group, dodecylcarbonyloxy group, phenylcarbonyloxy group, etc.), amide group (eg, methyl Carbonylamino group, ethylcarbonylamino group, dimethylcarbonylamino group, propylcarbonylamino group, pentylcarbonylamino group, cyclohexylcarbonylamino group, 2-ethylhexylcarbonylamino group, octylcarbonylamino group, dodecylcarbonylamino group, phenylcarbonylamino group , Naphthylcarbonylamino group, etc.), carbamoyl group (for example, aminocarbonyl group, methylaminocarbonyl group, dimethylaminocarbonyl group, propylamino group) Carbonyl group, pentylaminocarbonyl group, cyclohexylaminocarbonyl group, octylaminocarbonyl group, 2-ethylhexylaminocarbonyl group, dodecylaminocarbonyl group, phenylaminocarbonyl group, naphthylaminocarbonyl group, 2-pyridylaminocarbonyl group, etc.), ureido group (For example, methylureido group, ethylureido group, pentylureido group, cyclohexylureido group, octylureido group, dodecylureido group, phenylureido group, naphthylureido group, 2-pyridylaminoureido group), sulfinyl group (for example, methylsulfinyl group) Ethylsulfinyl group, butylsulfinyl group, cyclohexylsulfinyl group, 2-ethylhexylsulfinyl group, dodecylsulfinyl group, phenylsulfinyl group, Finyl group, naphthylsulfinyl group, 2-pyridylsulfinyl group, etc.), alkylsulfonyl group (for example, methylsulfonyl group, ethylsulfonyl group, butylsulfonyl group, cyclohexylsulfonyl group, 2-ethylhexylsulfonyl group, dodecylsulfonyl group, etc.), aryl A sulfonyl group or a heteroarylsulfonyl group (eg, phenylsulfonyl group, naphthylsulfonyl group, 2-pyridylsulfonyl group, etc.), amino group (eg, amino group, ethylamino group, dimethylamino group, butylamino group, cyclopentylamino group, 2-ethylhexylamino group, dodecylamino group, anilino group, naphthylamino group, 2-pyridylamino group, etc.), halogen atom (for example, fluorine atom, chlorine atom, bromine atom, etc.), fluorinated hydrocarbon group (for example, Fluoromethyl group, trifluoromethyl group, pentafluoroethyl group, pentafluorophenyl group, etc.), cyano group, nitro group, hydroxy group, mercapto group, silyl group (for example, trimethylsilyl group, triisopropylsilyl group, triphenylsilyl group) , Phenyldiethylsilyl group, etc.), phosphono group and the like.

  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.

  Hereinafter, although the specific example of the cyclic silicon compound represented by General formula (1) which is a material for organic electronics elements of this invention is shown, this invention is not limited to these.

  Furthermore, in the said cyclic silicon compound general formula (1), it is preferable that X1 and X2 have a structure represented by General formula (2)-(5).

Two arbitrary hydrogen atoms in the general formulas (2) to (5) are linking groups. Y _{1 to} Y ₃ represent NR, O, S, BR, CRR ′ or SiRR ′, and R and R ′ each represent a hydrogen atom or a substituent.

Z _{1 to} Z ₁₀ represent N or CR, and R represents a hydrogen atom or a substituent, respectively. However, at least one of Z _{1 to} Z ₁₀ is N. The substituents R and R ′ are the same as those used for the substituents R _{1 to} R ₈ .

  Examples of the structures represented by the general formulas (2) to (5) are shown below, but the present invention is not limited thereto.

  Hereinafter, although the specific example of the cyclic silicon compound which has the partial structure of General formula (2)-(5) which is a material for organic electronics elements of this invention is shown, this invention is not limited to these.

<< Method for Manufacturing Organic EL Element >>
As an example of a method for producing an organic EL device, a device comprising an anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode buffer layer (electron injection layer) / cathode Will be described.

  First, a desired electrode material, for example, a thin film made of a material for an anode is formed on a suitable substrate so as to have a thickness of 1 μm or less, preferably 10 nm to 200 nm, thereby producing 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, an electron transport layer, or a cathode buffer layer, which is an element material, is formed thereon.

  The thin film formation method is roughly classified into a dry method and a wet method. Examples of the dry method include a vacuum deposition method and a sputtering method. Examples of the wet method include a spin coating method, a casting method, a die coating method, and a blade. There are coating method, roll coating method, ink jet method, printing method, spray coating method, curtain coating method, LB method, etc., but it is possible to form a precise thin film and from the point of high productivity, vacuum deposition method and die coating. A method having high suitability for a roll-to-roll method such as a method, a roll coating method, an ink jet method, or a spray coating method is preferable. Different film forming methods may be applied for each layer.

  After the formation of these layers, a thin film made of a cathode material is formed thereon so as to have a thickness of 1 μm or less, preferably in the range of 50 to 200 nm, and a desired organic EL device can be obtained by providing a cathode. .

  Further, the order can be reversed, and the cathode, cathode buffer layer, electron transport layer, hole blocking layer, light emitting layer, hole transport layer, hole injection layer, and anode can be formed in this order.

  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 V to 40 V with the anode as + and the cathode as-. An alternating voltage may be applied. The alternating current waveform to be applied may be arbitrary.

  The organic EL device of the present invention is preferably produced from the hole injection layer to the cathode consistently by a single evacuation, but 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.

<< Constituent layers of organic EL elements >>
The constituent layers of the organic EL element of the present invention will be described. In this invention, although the preferable specific example of the layer structure of an organic EL element is shown below, this invention is not limited to these.

(I) Anode / light emitting layer / electron transport layer / cathode (ii) Anode / hole transport layer / light emitting layer / electron transport layer / cathode (iii) Anode / hole transport layer / light emitting layer / hole blocking layer / electron Transport layer / cathode (iv) Anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode buffer layer / cathode (v) Anode / anode buffer layer / hole transport layer / light emitting layer / hole Blocking layer / electron transport layer / cathode buffer layer / cathode (vi) anode // hole transport layer / anode buffer layer / light emitting layer / hole blocking layer / electron transport layer / cathode buffer layer / cathode (vii) anode / anode Buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode buffer layer / cathode The light emitting layer may form a unit to form a light emitting layer unit.

  Further, a non-light emitting intermediate layer may be provided between the light emitting layers, and the intermediate layer may include a charge generation layer. The organic EL element of the present invention is preferably a white light emitting layer, and is preferably a lighting device using these.

  Each layer which comprises the organic EL element of this invention is demonstrated.

<Light emitting layer>
The light emitting layer according to the present invention is a layer that emits light by recombination of electrons and holes injected from the electrode, the electron transport layer, or the hole transport layer, and the light emitting portion is not a layer of the light emitting layer. May be the interface between the light emitting layer and the adjacent layer.

  The thickness of the light emitting layer is not particularly limited, but from the viewpoint of the uniformity of the film to be formed, the application of unnecessary high voltage during light emission, and the improvement of the stability of the emission color with respect to the drive current. It is preferable to adjust to the range of 2 nm-200 nm, More preferably, it adjusts to the range of 5 nm-100 nm.

  The light emitting layer of the organic EL device of the present invention preferably contains at least one kind of a host compound (also called a light emitting host) and a light emitting dopant as a guest material, and contains a host compound and three or more kinds of light emitting dopants. More preferably. A host compound and a light emitting dopant (also referred to as a light emitting dopant compound) contained in the light emitting layer will be described below.

(Host compound and luminescent dopant)
(Host compound)
The host compound according to the present invention will be described.

  Here, the host compound in the present invention is a phosphorescent quantum yield of phosphorescence emission at a room temperature (25 ° C.) having a mass ratio of 20% or more in the compound contained in the light emitting layer. Is defined as a compound of less than 0.1. The phosphorescence quantum yield is preferably less than 0.01. Moreover, it is preferable that the mass ratio in the layer is 20% or more among the compounds contained in a light emitting layer.

  As the host compound, known host compounds may be used alone or in combination of two or more. By using a plurality of types of host compounds, it is possible to adjust the movement of charges, and the organic EL element can be made highly efficient. Moreover, it becomes possible to mix different light emission by using multiple types of light emission dopants mentioned later, and, thereby, arbitrary luminescent colors can be obtained.

  The light emitting host used in the present invention may be a conventionally known low molecular compound or a high molecular compound having a repeating unit, and a low molecular compound having a polymerizable group such as a vinyl group or an epoxy group (deposition polymerization property). Light emitting host).

  The compound represented by the general formula (1) according to the present invention is preferably used as the host compound according to the present invention.

When the compound represented by the general formula (1) according to the present invention is used as a host compound, the 6-membered aromatic ring represented by Ar ₂ is preferably a group derived from a benzene ring.

  As the known host compound that may be used in combination, a compound that has a hole transporting ability and an electron transporting ability, prevents the emission of light from becoming longer, and has a high Tg (glass transition temperature) is preferable.

  Specific examples of known host compounds include compounds described in the following documents.

  JP-A-2001-257076, 2002-308855, 2001-313179, 2002-319491, 2001-357777, 2002-334786, 2002-8860, 2002-334787, 2002-15871, 2002-334788, 2002-43056, 2002-334789, 2002-75645, 2002-338579, 2002-105445 gazette, 2002-343568 gazette, 2002-141173 gazette, 2002-352957 gazette, 2002-203683 gazette, 2002-363227 gazette, 2002-231453 gazette, No. 003-3165, No. 2002-234888, No. 2003-27048, No. 2002-255934, No. 2002-286061, No. 2002-280183, No. 2002-299060, No. 2002. -302516, 2002-305083, 2002-305084, 2002-308837, and the like.

  Hereinafter, although the specific example of the conventionally well-known compound used as a host compound of the light emitting layer of the organic EL element of this invention is given, this invention is not limited to these.

(Luminescent dopant)
The light emitting dopant according to the present invention will be described.

  As the light-emitting dopant, a fluorescent light-emitting dopant (also referred to as a fluorescent compound) or a phosphorescent light-emitting dopant (also referred to as a phosphorescent light emitter, a phosphorescent compound, a phosphorescent dopant, or the like) can be used.

(Fluorescent dopant)
Fluorescent dopants include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes, pyrylium dyes, perylene dyes, stilbene dyes , Polythiophene dyes, rare earth complex phosphors, and the like, and compounds having a high fluorescence quantum yield represented by laser dyes.

(Phosphorescent dopant)
The phosphorescent dopant according to the present invention will be described.

  The phosphorescent dopant according to the present invention is a compound in which light emission from an excited triplet is observed. Specifically, it is a compound that emits phosphorescence at room temperature (25 ° C.) and has a phosphorescence quantum yield. The phosphorescence quantum yield is preferably 0.1 or more, although it is defined as a compound of 0.01 or more at 25 ° C.

  The phosphorescence quantum yield can be measured by the method described in Spectroscopic II, page 398 (1992 edition, Maruzen) of Experimental Chemistry Course 4 of the 4th edition. Although the phosphorescence quantum yield in a solution can be measured using various solvents, the phosphorescence emitting dopant according to the present invention achieves the above phosphorescence quantum yield (0.01 or more) in any solvent. It only has to be done.

  There are two types of light emission of phosphorescent dopants in principle. One is the recombination of carriers on the host compound to which carriers are transported to generate an excited state of the host compound, and this energy is used as the phosphorescent dopant. The energy transfer type that obtains light emission from the phosphorescent dopant by moving to the phosphor, and the other is that the phosphorescent dopant becomes a carrier trap, and carrier recombination occurs on the phosphorescent dopant to cause phosphorescence emission. In any case, the excited state energy of the phosphorescent dopant is lower than the excited state energy of the host compound.

  The phosphorescent dopant can be appropriately selected from known materials used for the light emitting layer of the organic EL device.

  The phosphorescent dopant according to the present invention is preferably a complex compound containing a group 8-10 metal in the periodic table of elements, more preferably an iridium compound, an osmium compound, or a platinum compound (platinum complex system). Compound) and rare earth complexes, and most preferred is an iridium compound.

  Hereinafter, although the specific example of the phosphorescent dopant which can be preferably used in this invention is shown, this invention is not limited to these.

<< Charge transport layer: electron transport layer, hole transport layer >>
Examples of the charge transport layer according to the present invention include an electron transport layer and a hole transport layer.

  Hereinafter, the electron transport layer and the hole transport layer according to the present invention will be described in detail.

《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 as a single layer or a plurality of layers. Examples of conventionally known materials used for the electron transport layer (hereinafter referred to as electron transport materials) include heterocyclic tetracarboxylic acid anhydrides such as nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, naphthalene perylene, And azacarbazole derivatives including carbodiimide, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives, carboline derivatives, and the like.

  Conventionally, an electron transport material (also serving as a hole blocking material) used for the electron transport layer may have a function of transmitting electrons injected from the cathode to the light emitting layer. As the electron transporting material, any one of conventionally known compounds can be selected and used. Anthraquinodimethane and anthrone derivatives, oxadiazole derivatives, pyridine derivatives, azacarbazole derivatives and the like can be mentioned.

  In the 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.

  Furthermore, a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used. Also, metal complexes of 8-quinolinol derivatives such as tris (8-quinolinol) aluminum (Alq), tris (5,7-dichloro-8-quinolinol) aluminum, tris (5,7-dibromo-8-quinolinol) aluminum, Tris (2-methyl-8-quinolinol) aluminum, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), etc., and the central metals of these metal complexes are In, Mg, Cu , Ca, Sn, Ga, or Pb can also be used as an electron transport material.

  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 distyrylpyrazine derivative exemplified as the material of the light emitting layer can also be used as an electron transport material, and an inorganic semiconductor such as n-type-Si, n-type-SiC, etc. as in the case of the hole injection layer and the hole transport layer. Can also be used as an electron transporting material.

  The 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, a printing method including an ink jet method, or an LB method.

  Although there is no restriction | limiting in particular about the film thickness of an electron carrying layer, Usually, 5 nm-about 5 micrometers, Preferably it is 5 nm-200 nm. The electron transport layer may have a single layer structure composed of one or more of the above materials.

  Alternatively, an electron transport layer with high n property doped with impurities as a guest material can be used. Examples thereof include JP-A-4-297076, JP-A-10-270172, JP-A-2000-196140, 2001-102175, J.A. Appl. Phys. 95, 5773 (2004), and the like.

  In the present invention, it is preferable to use an electron transport layer having such a high n property because an element with lower power consumption can be manufactured. Hereinafter, although the specific example of the conventionally well-known compound used for formation of the electron carrying layer of the organic EL element of this invention is given, this invention is not limited to these.

《Hole transport layer》
The hole transport layer is made of a hole transport 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.

  The hole transport material has any one of hole injection or transport and electron barrier properties, and may be either organic or inorganic. 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, hydrazone derivatives, Examples thereof include stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.

  The above-mentioned materials can be used as the hole transport material, but it is preferable to use a porphyrin compound, an aromatic tertiary amine compound and a styrylamine compound, particularly an aromatic tertiary amine compound.

  Representative examples of aromatic tertiary amine compounds and styrylamine compounds include N, N, N ', N'-tetraphenyl-4,4'-diaminophenyl; N, N'-diphenyl-N, N'- Bis (3-methylphenyl)-[1,1′-biphenyl] -4,4′-diamine (TPD); 2,2-bis (4-di-p-tolylaminophenyl) propane; 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane; N, N, N ′, N′-tetra-p-tolyl-4,4′-diaminobiphenyl; 1,1-bis (4-di-p-tolyl) Aminophenyl) -4-phenylcyclohexane; bis (4-dimethylamino-2-methylphenyl) phenylmethane; bis (4-di-p-tolylaminophenyl) phenylmethane; N, N'-diphenyl-N, N ' − (4-methoxyphenyl) -4,4'-diaminobiphenyl; N, N, N ', N'-tetraphenyl-4,4'-diaminodiphenyl ether; 4,4'-bis (diphenylamino) quadriphenyl; N, N, N-tri (p-tolyl) amine; 4- (di-p-tolylamino) -4 '-[4- (di-p-tolylamino) styryl] stilbene; 4-N, N-diphenylamino- (2-diphenylvinyl) benzene; 3-methoxy-4′-N, N-diphenylaminostilbenzene; N-phenylcarbazole, and also two of those described in US Pat. No. 5,061,569. Having a condensed aromatic ring in the molecule, for example, 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPD), JP-A-4-3086 4,4 ', 4 "-tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine in which three triphenylamine units described in Japanese Patent No. 8 are linked in a starburst type ( MTDATA) and the like.

  Furthermore, a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used. In addition, inorganic compounds such as p-type-Si and p-type-SiC can also be used as the hole injection material and the hole transport material.

  JP-A-11-251067, J. Org. Huang et. al. A so-called p-type hole transport material as described in a book (Applied Physics Letters 80 (2002), p. 139) can also be used. In the present invention, these materials are preferably used because a light-emitting element with higher efficiency can be obtained.

  The hole transport layer can be formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. it can. About the film thickness of a positive hole transport layer, it is preferable that it is the range of 5 nm-5 micrometers, More preferably, it is 5 nm-200 nm. The hole transport layer may have a single layer structure composed of one or more of the above materials.

  Alternatively, a hole transport layer having a high p property doped with impurities can be used. Examples thereof include JP-A-4-297076, JP-A-2000-196140, 2001-102175, J. Pat. Appl. Phys. 95, 5773 (2004), and the like.

  In the present invention, it is preferable to use a hole transport layer having such a high p property because a device with lower power consumption can be produced. Hereinafter, although the specific example of the conventionally well-known compound used for formation of the positive hole transport layer of the organic EL element of this invention is given, this invention is not limited to these.

<Blocking layer: hole blocking layer, electron blocking layer>
The blocking layer is provided as necessary in addition to the basic constituent layer of the organic compound thin film as described above. For example, it is described in JP-A Nos. 11-204258, 11-204359, and “Organic EL elements and their forefront of industrialization” (issued by NTT, Inc. on November 30, 1998). There is a hole blocking (hole blocking) layer.

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

  Moreover, the structure of the above-mentioned electron carrying layer can be used as a hole-blocking layer concerning this invention as needed.

  The hole blocking layer of the organic EL device according to the present invention is preferably provided adjacent to the light emitting layer.

  The hole blocking layer preferably contains the carbazole derivative, azacarbazole derivative, pyridine derivative, or the like mentioned as the host compound.

  In the present invention, when a plurality of light emitting layers having different light emission colors are provided, the light emitting layer having the shortest wavelength of light emission is preferably closest to the anode among all the light emitting layers. In this case, it is preferable to additionally provide a hole blocking layer between the shortest wave layer and the light emitting layer next to the anode next to the anode.

  Furthermore, it is preferable that 50% by mass or more of the compound contained in the hole blocking layer provided at the position has an ionization potential of 0.3 eV or more larger than the host compound of the shortest wave emitting layer.

  The ionization potential is defined by the energy required to emit an electron at the HOMO (highest occupied molecular orbital) level of the compound to the vacuum level, and can be obtained by the following method, for example.

  (1) Using Gaussian 98 (Gaussian 98, Revision A.11.4, MJ Frisch, et al, Gaussian, Inc., Pittsburgh PA, 2002.), a molecular orbital calculation software manufactured by Gaussian, USA The ionization potential can be obtained as a value obtained by rounding off the second decimal place of the value (eV unit converted value) calculated by performing structural optimization using B3LYP / 6-31G *. This calculation value is effective because the correlation between the calculation value obtained by this method and the experimental value is high.

  (2) The ionization potential can also be obtained by a method of directly measuring by photoelectron spectroscopy. For example, a method known as ultraviolet photoelectron spectroscopy can be suitably used by using a low energy electron spectrometer “Model AC-1” manufactured by Riken Keiki Co., Ltd.

  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 that has a function of transporting holes and has an extremely small ability to transport electrons, and transports electrons while transporting holes. By blocking, the recombination probability of electrons and holes can be improved. Moreover, the structure of the positive hole transport layer mentioned later can be used as an electron blocking layer as needed. The film thickness of the hole blocking layer and the electron transport layer according to the present invention is preferably 3 nm to 100 nm, and more preferably 5 nm to 30 nm.

<< Charge injection layer: electron injection layer, hole injection layer >>
The charge injection layer according to the present invention is provided as necessary, and includes an electron injection layer and a hole injection layer, and as described above, between the anode and the light emitting layer or the hole transport layer, and the cathode and the light emitting layer or the electron transport layer. It may be present between.

  An injection layer is a layer provided between an electrode and an organic layer in order to reduce drive voltage and improve light emission luminance. “Organic EL element and its forefront of industrialization (issued by NTT Corporation on November 30, 1998) 2), Chapter 2, “Electrode Materials” (pages 123 to 166) in detail, and includes a hole injection layer (anode buffer layer) and an electron injection layer (cathode buffer layer).

  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. As a specific example, copper phthalocyanine is used. Examples thereof include a phthalocyanine buffer layer represented by an oxide, an oxide buffer layer represented by vanadium oxide, an amorphous carbon buffer layer, and a polymer buffer layer using a conductive polymer such as polyaniline (emeraldine) or polythiophene.

  The details of the cathode buffer layer (electron injection layer) are described in JP-A-6-325871, JP-A-9-17574, JP-A-10-74586, and the like. Specifically, strontium, aluminum, etc. Metal buffer layer typified by lithium, 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. . The buffer layer (injection layer) is preferably a very thin film, and the film thickness is preferably in the range of 0.1 nm to 5 μm although it depends on the material.

  In addition, the materials used for the anode buffer layer and the cathode buffer layer can be used in combination with other materials. For example, the materials can be mixed in the hole transport layer or the electron transport layer.

"anode"
As the anode in the organic EL element, 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 CuI, indium tin oxide (ITO), SnO ₂ , and ZnO. Alternatively, an amorphous material such as IDIXO (In ₂ O ₃ —ZnO) capable of forming a transparent conductive film may be used.

  For the anode, these electrode materials may be formed into a thin film by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by a photolithography method, or when pattern accuracy is not so high (about 100 μm or more) A pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering of the electrode material.

  Or when using the substance which can be apply | coated like an organic electroconductivity compound, wet film-forming methods, such as a printing system and a coating system, can also be used. When light emission is extracted from the anode, it is desirable that the transmittance be greater than 10%, and the sheet resistance as the anode is preferably several hundred Ω / □ or less.

  Further, although the film thickness depends on the material, the range of 10 nm to 1000 nm is preferable, and the range of 10 nm to 200 nm is more preferable.

"cathode"
As the cathode, a material having a work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound and a mixture thereof as an electrode material is used. Specific examples of such electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al ₂ O ₃ ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like.

Among these, from the point of durability against electron injection and oxidation, etc., a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function than this, for example, a magnesium / silver mixture, Magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al ₂ O ₃ ) mixtures, lithium / aluminum mixtures, aluminum and the like are preferred.

  In the present invention, these electrode substances (also referred to as conductive materials) are used as a conductive paste to form a thin film by a wet method to produce a cathode.

  The sheet resistance as the cathode is preferably several hundred Ω / □ or less, and the film thickness is preferably in the range of 10 nm to 5 μm, more preferably in the range of 50 nm to 200 nm. In order to transmit the emitted light, if either one of the anode or the cathode of the organic EL element is transparent or translucent, the light emission luminance is improved, which is convenient. Moreover, after producing the said metal by the film thickness of 1 nm-20 nm to a cathode, the transparent or semi-transparent cathode can be produced by producing the electroconductive transparent material quoted by description of the anode on it, By applying this, an element in which both the anode and the cathode are transmissive can be manufactured.

"substrate"
As a substrate (hereinafter also referred to as a base, a base material, a support substrate, a support, etc.) that can be used in the organic EL device according to the present invention, there is no particular limitation on the type of glass, plastic, etc., and it is transparent. Or opaque. When extracting light from the substrate side, the substrate is preferably transparent. Examples of the transparent substrate preferably used include glass, quartz, and a transparent resin film. A particularly preferable substrate is a resin film capable of giving flexibility to the organic EL element. Examples of the resin film include polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), polyethylene, polypropylene, cellophane, cellulose diacetate, cellulose triacetate, cellulose acetate butyrate, cellulose acetate propionate (CAP), Cellulose esters such as cellulose acetate phthalate (TAC) and cellulose nitrate or derivatives thereof, polyvinylidene chloride, polyvinyl alcohol, polyethylene vinyl alcohol, syndiotactic polystyrene, polycarbonate, norbornene resin, polymethylpentene, polyether ketone, polyimide , Polyethersulfone (PES), polyphenylene sulfide, polysulfones Cycloolefin resins such as polyetherimide, polyetherketoneimide, polyamide, fluororesin, nylon, polymethylmethacrylate, acrylic or polyarylate, Arton (trade name, manufactured by JSR) or Appel (trade name, manufactured by Mitsui Chemicals) Can be mentioned. On the surface of the resin film, an inorganic film, an organic film, or a hybrid film of both may be formed. Water vapor permeability measured by a method in accordance with JIS K 7129-1992 (25 ± 0.5 ° C., It is preferably a barrier film having a relative humidity (90 ± 2)% RH) of 0.01 g / (m ² · 24 h) or less, and further, oxygen permeation measured by a method according to JIS K 7126-1987. The film is preferably a high barrier film having a degree of 10 ⁻³ ml / (m ² · 24 h · MPa) or less and a water vapor permeability of 10 ⁻⁵ g / (m ² · 24 h) or less. As a material for forming the barrier film, any material may be used as long as it has a function of suppressing entry of elements that cause deterioration of elements such as moisture and oxygen. For example, silicon oxide, silicon dioxide, silicon nitride, or the like can be used. Further, in order to improve the brittleness of the film, it is more preferable to have a laminated structure of these inorganic layers and organic material layers. Although there is no restriction | limiting in particular about the lamination | stacking order of an inorganic layer and an organic layer, It is preferable to laminate | stack both alternately several times. The method for forming the barrier film is not particularly limited. For example, the vacuum deposition method, the sputtering method, the reactive sputtering method, the molecular beam epitaxy method, the cluster ion beam method, the ion plating method, the plasma polymerization method, the atmospheric pressure plasma weighting. A combination method, a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, and the like can be used. However, an atmospheric pressure plasma polymerization method as described in JP-A-2004-68143 is particularly preferable.

  Examples of the opaque substrate include a metal plate such as aluminum and stainless steel, a film, an opaque resin substrate, a ceramic substrate, and the like. The external extraction efficiency at room temperature of light emission of the organic EL device according to the present invention is preferably 1% or more, more preferably 5% 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 sent to the organic EL element × 100.

  In addition, a hue improvement filter such as a color filter may be used in combination, or a color conversion filter that converts the emission color from the organic EL element into multiple colors using a phosphor may be used in combination. In the case of using a color conversion filter, the λmax of light emission of the organic EL element is preferably 480 nm or less.

<Sealing>
As a sealing means of the organic EL element used for this invention, the method of adhere | attaching a sealing member, an electrode, and a support substrate with an adhesive agent can be mentioned, for example.

  As a sealing member, it should just be arrange | positioned so that the display area | region of an organic EL element may be covered, and concave plate shape or flat plate shape may be sufficient. Further, transparency and electrical insulation are not particularly limited.

  Specific examples include a glass plate, a polymer plate / film, and a metal plate / film. Examples of the glass plate include soda-lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz. Examples of the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, and polysulfone. Examples of the metal plate include those made of one or more metals or alloys selected from the group consisting of stainless steel, iron, copper, aluminum, magnesium, nickel, zinc, chromium, titanium, molybdenum, silicon, germanium, and tantalum.

  In the present invention, a polymer film and a metal film can be preferably used because the organic EL element can be thinned.

Furthermore, the polymer film has an oxygen permeability measured by a method according to JIS K 7126-1987 of 1 × 10 ⁻³ ml / (m ² / 24h) or less, and is measured by a method according to JIS K 7129-1992. is water vapor transmission rate (25 ± 0.5 ° C., relative humidity (90 ± 2)% RH) is preferably that of ^{1 × 10 -3 ml / (m} 2 / 24h) or less.

  For processing the sealing member into a concave shape, sandblasting, chemical etching, or the like is used.

  Specific examples of the adhesive include photocuring and thermosetting adhesives having reactive vinyl groups such as acrylic acid oligomers and methacrylic acid oligomers, and moisture curing adhesives such as 2-cyanoacrylates. be able to. Moreover, heat | fever and chemical curing types (two-component mixing), such as an epoxy type, can be mentioned. Moreover, hot-melt type polyamide, polyester, and polyolefin can be mentioned. Moreover, a cationic curing type ultraviolet curing epoxy resin adhesive can be mentioned.

  In addition, since an organic EL element may deteriorate by heat processing, what can be adhesive-hardened from room temperature to 80 degreeC is preferable. A desiccant may be dispersed in the adhesive. Application | coating of the adhesive agent to a sealing part may use commercially available dispenser, and may print like screen printing.

  In addition, it is also possible to suitably form an inorganic or organic layer as a sealing film by covering the electrode and the organic layer on the outer side of the electrode facing the substrate with the organic layer interposed therebetween, and in contact with the substrate. In this case, the material for forming the film may be any material that has a function of suppressing intrusion of elements that cause deterioration of elements such as moisture and oxygen. For example, silicon oxide, silicon dioxide, silicon nitride, or the like may be used. it can.

  Further, in order to improve the brittleness of the film, it is preferable to have a laminated structure of these inorganic layers and layers made of organic materials. The method for forming these films is not particularly limited. For example, vacuum deposition, sputtering, reactive sputtering, molecular beam epitaxy, cluster ion beam method, ion plating method, plasma polymerization method, atmospheric pressure plasma A polymerization method, a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or the like can be used.

  In the gap between the sealing member and the display area of the organic EL element, an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil can be injected in the gas phase and liquid phase. preferable. A vacuum is also possible. Moreover, a hygroscopic compound can also be enclosed inside.

  Examples of the hygroscopic compound include metal oxides (for example, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide) and sulfates (for example, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate). Etc.), metal halides (eg calcium chloride, magnesium chloride, cesium fluoride, tantalum fluoride, cerium bromide, magnesium bromide, barium iodide, magnesium iodide etc.), perchloric acids (eg perchloric acid) Barium, magnesium perchlorate, and the like), and anhydrous salts are preferably used in sulfates, metal halides, and perchloric acids.

《Protective film, protective plate》
In order to increase the mechanical strength of the element, a protective film or a protective plate may be provided on the outer side of the sealing film on the side facing the substrate with the organic layer interposed therebetween or on the sealing film. In particular, when the sealing is performed by the sealing film, the mechanical strength is not necessarily high, and thus it is preferable to provide such a protective film and a protective plate. As a material that can be used for this, the same glass plate, polymer plate / film, metal plate / film, etc. used for the sealing can be used, but the polymer film is light and thin. Is preferably used.

《Light extraction》
The organic EL element emits light inside a layer having a refractive index higher than that of air (refractive index is about 1.7 to 2.1) and can extract only about 15% to 20% of the light generated in the light emitting layer. It is generally said. This is because light incident on the interface (interface between the transparent substrate and air) at an angle θ greater than the critical angle causes total reflection and cannot be taken out of the device, or between the transparent electrode or light emitting layer and the transparent substrate. This is because the light is totally reflected between the light and the light is guided through the transparent electrode or the light emitting layer, and as a result, the light escapes in the direction of the element side surface.

  As a method for improving the light extraction efficiency, for example, a method of forming irregularities on the surface of the transparent substrate to prevent total reflection at the interface between the transparent substrate and the air (US Pat. No. 4,774,435), A method for improving efficiency by giving light condensing property to a substrate (Japanese Patent Laid-Open No. 63-314795), a method for forming a reflective surface on the side surface of an organic EL element (Japanese Patent Laid-Open No. 1-220394), a substrate A method of forming an antireflection film by introducing a flat layer having an intermediate refractive index between the substrate and the light emitter (Japanese Patent Laid-Open No. 62-172691), and lowering the refractive index than the substrate between the substrate and the light emitter. A method of introducing a flat layer having a structure (Japanese Patent Laid-Open No. 2001-202827), a method of forming a diffraction grating between any one of a substrate, a transparent electrode layer, and a light emitting layer (including between the substrate and the outside) No. 283751) .

  In the present invention, these methods can be used in combination with the organic EL device according to the present invention. However, a method of introducing a flat layer having a lower refractive index than the substrate between the substrate and the light emitter, or a substrate, A method of forming a diffraction grating between any layers of the transparent electrode layer and the light emitting layer (including between the substrate and the outside) can be suitably used.

  In the present invention, by combining these means, it is possible to obtain an organic EL device having further high luminance or durability.

  When a medium having a low refractive index is formed between the transparent electrode and the transparent substrate with a thickness longer than the wavelength of light, the light extracted from the transparent electrode has a higher extraction efficiency to the outside as the refractive index of the medium is lower.

  Examples of the low refractive index layer include aerogel, porous silica, magnesium fluoride, and a fluorine-based polymer. Since the refractive index of the transparent substrate is generally about 1.5 to 1.7, the low refractive index layer preferably has a refractive index of about 1.5 or less, more preferably 1.35 or less. .

  The thickness of the low refractive index medium is preferably at least twice the wavelength in the medium. This is because the effect of the low refractive index layer is diminished when the thickness of the low refractive index medium is about the wavelength of light and the electromagnetic wave that has exuded by evanescent enters the substrate.

  The method of introducing a diffraction grating into an interface or any medium that causes total reflection is characterized by a high effect of improving light extraction efficiency.

  This method uses the property that the diffraction grating can change the direction of light to a specific direction different from refraction by so-called Bragg diffraction such as first-order diffraction and second-order diffraction. Light that cannot be emitted due to total internal reflection between layers is diffracted by introducing a diffraction grating in any layer or medium (in a transparent substrate or transparent electrode), and the light is removed. I want to take it out.

  The introduced diffraction grating desirably has a two-dimensional periodic refractive index. This is because light emitted from the light-emitting layer is randomly generated in all directions, so in a general one-dimensional diffraction grating having a periodic refractive index distribution only in a certain direction, only light traveling in a specific direction is diffracted. Therefore, the light extraction efficiency does not increase so much.

  However, by making the refractive index distribution a two-dimensional distribution, light traveling in all directions is diffracted, and light extraction efficiency is increased.

  As described above, the position where the diffraction grating is introduced may be in any of the layers or in the medium (in the transparent substrate or in the transparent electrode), but is preferably in the vicinity of the organic light emitting layer where light is generated.

  At this time, the period of the diffraction grating is preferably about 1/2 to 3 times the wavelength of light in the medium.

  The arrangement of the diffraction grating is preferably two-dimensionally repeated such as a square lattice, a triangular lattice, or a honeycomb lattice.

<Condenser sheet>
The organic EL device according to the present invention can be processed on the light extraction side of the substrate, for example, by providing a microlens array-like structure, or combined with a so-called condensing sheet, for example, in a specific direction, for example, the device light emitting surface On the other hand, the brightness | luminance in a specific direction can be raised by condensing in a front direction.

  As an example of the microlens array, quadrangular pyramids having a side of 30 μm and an apex angle of 90 degrees are two-dimensionally arranged on the light extraction side of the substrate. One side is preferably 10 μm to 100 μm.

  If it becomes smaller than this, the effect of diffraction will generate | occur | produce and color, and if too large, thickness will become thick and is not preferable.

  As the condensing sheet, for example, a sheet that is put into practical use in an LED backlight of a liquid crystal display device can be used. As such a sheet, for example, a brightness enhancement film (BEF) manufactured by Sumitomo 3M Limited can be used.

  As the shape of the prism sheet, for example, the base material may be formed by forming a △ -shaped stripe having a vertex angle of 90 degrees and a pitch of 50 μm, or the vertex angle is rounded and the pitch is changed randomly. Other shapes may be used.

  Moreover, in order to control the light emission angle from a light emitting element, you may use together a light diffusing plate and a film with a condensing sheet. For example, a diffusion film (light-up) manufactured by Kimoto Co., Ltd. can be used.

<Application>
The organic EL element of the present invention can be used as a display device, a display, and various light emission sources. For example, lighting devices (home lighting, interior lighting), clock and liquid crystal backlights, billboard advertisements, traffic lights, light sources of optical storage media, light sources of electrophotographic copying machines, light sources of optical communication processors, light Although the light source of a sensor etc. are mentioned, It is not limited to this, Especially, it can use effectively for the use as a backlight of a liquid crystal display device, and a light source for illumination.

  In the organic EL element of the present invention, patterning may be performed by a metal mask, an ink jet printing method, or the like as needed during film formation. In the case of patterning, only the electrode may be patterned, the electrode and the light emitting layer may be patterned, or the entire layer of the device may be patterned. Can do.

  The light emission color of the organic EL device of the present invention and the compound according to the present invention is shown in FIG. 4.16 on page 108 of “New Color Science Handbook” (edited by the Japan Color Society, University of Tokyo Press, 1985). It is determined by the color when the result measured with the total CS-1000 (manufactured by Konica Minolta Sensing) is applied to the CIE chromaticity coordinates.

Further, when the organic EL element according to the present invention is a white element, white means that the chromaticity in the CIE1931 color system at 1000 cd / m ² is measured when the front luminance at 2 ° viewing angle is measured by the above method. , X = 0.33 ± 0.07 and Y = 0.33 ± 0.1.

<Display device>
The display device of the present invention will be described. The display device of the present invention comprises the organic EL element of the present invention.

  Although the display device of the present invention may be single color or multicolor, the multicolor display device will be described here. 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 vapor deposition, casting, spin coating, ink jet, printing, or the like.

  In the case of patterning only the light emitting layer, the method is not limited. However, the vapor deposition method, the ink jet method, the spin coating method, and the printing method are preferable.

  The configuration of the organic EL element provided in the display device is selected from the above-described configuration examples of the organic EL element as necessary.

  Moreover, the manufacturing method of an organic EL element is as having shown to the one aspect | mode of manufacture of the organic EL element of said invention.

  In the case of applying a DC voltage to the obtained multicolor display device, light emission can be observed by applying a voltage of about 2V to 40V with the positive polarity of the anode and the negative polarity of the cathode. Further, even when a voltage is applied with the opposite polarity, no current flows and no light emission occurs. Further, when an AC voltage is applied, light is emitted only when the anode is in the + state and the cathode is in the-state. The alternating current waveform to be applied may be arbitrary.

  The multicolor display device can be used as a display device, a display, and various light emission sources. In a display device or display, full-color display is possible by using three types of organic EL elements of blue, red, and green light emission.

  Examples of the display device and display include a television, a personal computer, a mobile device, an AV device, a character broadcast display, and an information display in an automobile. In particular, it may be used as a display device for reproducing still images and moving images, and the driving method when used as a display device for reproducing moving images may be either a simple matrix (passive matrix) method or an active matrix method.

  Light 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 sources for optical sensors, etc. The present invention is not limited to these examples.

  Hereinafter, an example of a display device having the organic EL element of the present invention will be described with reference to the drawings.

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

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

  The control unit B is electrically connected to the display unit A, and sends a scanning signal and an image data signal to each of a plurality of pixels based on image information from the outside, and the pixels for each scanning line respond to the image data signal by the scanning signal. The image information is sequentially emitted to scan the image and display the image information on the display unit A.

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

  The display unit A includes 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.

  In the figure, the light emitted from the pixel 3 is extracted in the direction of the white arrow (downward).

  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 are illustrated). Not)

  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 according to 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.

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

  FIG. 3 is a schematic diagram of a pixel.

  The pixel includes an organic EL element 10, a switching transistor 11, a driving transistor 12, a capacitor 13, and the like. A full color display can be performed by using red, green, and blue light emitting organic EL elements as the organic EL elements 10 in a plurality of pixels, and juxtaposing 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 through the data line 6. When a scanning signal is applied from the control unit B to the gate of the switching transistor 11 via the scanning line 5, the driving of the switching transistor 11 is turned on, and the image data signal applied to the drain is supplied to the capacitor 13 and the driving transistor 12. Is transmitted to the gate.

  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 power supply line 7 connects to the organic EL element 10 according to the potential of the image data signal applied to the gate. Current is supplied.

  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 maintains 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. Until then, the light emission of the organic EL element 10 continues. When the 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 light emission of the organic EL element 10 is performed by providing the switching transistor 11 and the drive transistor 12 which are active elements with respect to the organic EL element 10 of each of the plurality of pixels. It is carried out. Such a light emitting method is called an active matrix method.

  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 by turning on / off a predetermined light emission amount by a binary image data signal. Good. The potential of the capacitor 13 may be maintained until the next scanning signal is applied, or may be discharged immediately before the next scanning signal is applied.

  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 passive matrix display device. 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.

  When the scanning signal of the scanning line 5 is applied by sequential scanning, the pixels 3 connected to the applied scanning line 5 emit light according to the image data signal.

  In the passive matrix system, the pixel 3 has no active element, and the manufacturing cost can be reduced.

《Lighting device》
The lighting device of the present invention will be described. The illuminating device of this invention has the said organic EL element.

  The organic EL element of the present invention may be used as an organic EL element having a resonator structure. The purpose of use of the organic EL element having such a resonator structure is as follows. The light source of a machine, the light source of an optical communication processing machine, the light source of a photosensor, etc. are mentioned, However, It is not limited to these. Moreover, you may use for the said use by making a laser oscillation.

  Further, the organic EL element of the present invention may be used as a kind of lamp for illumination or exposure light source, a projection device for projecting an image, or a display for directly viewing a still image or a moving image. It may be used as a device (display).

  The driving method when used as a display device for moving image reproduction may be either a simple matrix (passive matrix) method or an active matrix method. Alternatively, a full-color display device can be manufactured by using two or more organic EL elements of the present invention having different emission colors.

  The organic EL material of the present invention can 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 color mixing. The combination of a plurality of emission colors may include three emission maximum wavelengths of the three primary colors of blue, green, and blue, or two using the relationship of complementary colors such as blue and yellow, blue green and orange, etc. The thing containing the light emission maximum wavelength may be used.

  In addition, a combination of light emitting materials for obtaining a plurality of emission colors is a combination of a plurality of phosphorescent or fluorescent materials, a light emitting material that emits fluorescence or phosphorescence, and light from the light emitting material as excitation light. Any of those combined with a dye material that emits light may be used, but in the white organic EL device according to the present invention, only a combination of a plurality of light-emitting dopants may be mixed.

  It is only necessary to provide a mask only when forming a light emitting layer, a hole transport layer, an electron transport layer, etc., and simply arrange them separately by coating with the mask. Since other layers are common, patterning of the mask or the like is not necessary. In addition, for example, an electrode film can be formed by a vapor deposition method, a cast method, a spin coating method, an ink jet method, a printing method, or the like, and productivity is also improved.

  According to this method, unlike a white organic EL device in which light emitting elements of a plurality of colors are arranged in parallel in an array, the elements themselves are luminescent white.

  There is no restriction | limiting in particular as a luminescent material used for a light emitting layer, For example, if it is a backlight in a liquid crystal display element, the metal complex which concerns on this invention so that it may suit the wavelength range corresponding to CF (color filter) characteristic, Any one of known luminescent materials may be selected and combined to whiten.

<< One Embodiment of Lighting Device of the Present Invention >>
One aspect of the lighting device of the present invention that includes the organic EL element of the present invention will be described.

  The non-light emitting surface of the organic EL device of the present invention is covered with a glass case, a glass substrate having a thickness of 300 μm is used as a sealing substrate, and an epoxy-based photocurable adhesive (LUX TRACK manufactured by Toagosei Co., Ltd.) is used as a sealing material. LC0629B) is applied, and this is overlaid on the cathode and brought into close contact with the transparent support substrate, irradiated with UV light from the glass substrate side, cured and sealed, and an illumination device as shown in FIGS. Can be formed.

  FIG. 5 shows a schematic diagram of a lighting device, and the organic EL element 101 of the present invention is covered with a glass cover 102 (in addition, the sealing operation with the glass cover is to bring the organic EL element 101 into contact with the air And a glove box under a nitrogen atmosphere (in an atmosphere of high-purity nitrogen gas having a purity of 99.999% or more).

  FIG. 6 shows a cross-sectional view of the lighting device. In FIG. 6, 105 denotes a cathode, 106 denotes an organic EL layer, and 107 denotes a glass substrate with a transparent electrode. The glass cover 102 is filled with nitrogen gas 108 and a water catching agent 109 is provided.

  EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited thereto.

Example 1
(Synthesis Method of General Formula (3) (CSi-29))

Tert-Butyllithium pentane solution (1.55 M / l, 24.0 ml, 37) in THF (186 ml) solution of 4,6-dibromodibenzofuran (3.00 g, 9.30 mmol) at −78 ° C. under nitrogen atmosphere. .2 mmol) was added dropwise to prepare a 4,6-dibromodibenzofuran solution. The prepared THF solution of 4,6-dibromodibenzofuran was added dropwise to a THF solution of 1,2-dichlorotetramethyldisilane (1.74 g, 9.30 mmol) over 40 minutes at room temperature under a nitrogen atmosphere. After completion of the dropwise addition, the mixture was stirred for 40 minutes, and pure water (50 ml) was added to stop the reaction. After separating the organic layer, the aqueous layer was extracted with CHCl ₃ (3 × 500 ml), and the organic layer was washed with saturated brine and dried over magnesium sulfate. After completion of drying, the solvent was removed under reduced pressure, and the residue was washed with about 20 ml of diethyl ether to obtain CSi-29 (1.00 g, 50%) as the target product as a yellow solid. The compound was identified by NMR and Mass, and the purity was measured by HPLC and confirmed to be> 99%. The glass transition temperature was 171 ° C. and the decomposition temperature was 309 ° C.

  Cyclic silicon compounds used in the invention can be synthesized relatively easily in the same manner as described above, and the synthesis of dihalogen intermediates and the like can be carried out by known methods described in the Chemical Chemistry, 5th edition, Experimental Chemistry Course, etc. It can be used as appropriate.

Example 2
<Preparation of organic EL element 1-2>

  Transparent support provided with this ITO transparent electrode after patterning on a substrate (NH45 manufactured by NH Techno Glass) made of ITO (indium tin oxide) with a thickness of 100 nm on a glass substrate of 100 mm × 100 mm × 1.1 mm as an anode The substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.

  A solution obtained by diluting poly (3,4-ethylenedioxythiophene) -polystyrene sulfonate (PEDOT / PSS, manufactured by HC Starck Co., Ltd., CLEVIO P VP AI 4083) to 70% with pure water on the transparent support substrate. A thin film was formed by spin coating under conditions of 3000 rpm and 30 seconds, and then dried at 200 ° C. for 1 hour to provide a 20 nm-thick hole transport layer.

This transparent support substrate was fixed to a substrate holder of a commercially available vacuum deposition apparatus, while 100 mg of CSi-7 was placed in a molybdenum resistance heating boat and mounted on the vacuum deposition apparatus. Similarly, 100 mg each of α-NPD, CBP, Ir (ppy) ₃ , and Alq ₃ was put into a boat and mounted.

Next, after reducing the vacuum chamber to 4 × 10 ⁻⁴ Pa, the heating boat containing α-NPD was energized and heated, and deposited on the transparent support substrate at a deposition rate of 0.1 nm / sec. A hole transport layer was provided.

Further, the heating boat containing the light-emitting host CSi-7 and Ir (ppy) ₃ was energized and heated, and co-deposited on the hole transport layer at a deposition rate of 0.1 nm / sec and 0.006 nm / sec, respectively. A 40 nm light emitting layer was provided.

Further, the heating boat containing Alq ₃ was heated by energization, and was deposited on the light emitting layer at a deposition rate of 0.1 nm / sec to provide an electron transport layer having a thickness of 30 nm. In addition, the substrate temperature at the time of vapor deposition was room temperature.

  Then, 0.5 nm of lithium fluoride was vapor-deposited as a cathode buffer layer, and also aluminum 110nm was vapor-deposited, the cathode was formed, and the organic EL element 1-2 was produced.

  Organic EL elements 1-1 and 1-3 to 1-13 were produced in exactly the same manner except that CSi-7 used for the light-emitting host was changed to the material shown in Table 1.

  The band gap of the compound of the present invention used for the organic EL devices 1-1 to 1-13 was measured by the following method, and the results are shown in Table 1.

  The band gap between the ground state and the triplet excited state is determined by Gaussian 98 (Gaussian 98, Revision A.11.4, MJ Frisch, et al, Gaussian, Inc., software for molecular orbital calculation manufactured by Gaussian, USA). Pittsburgh PA, 2002.), and a value (eV unit converted value) calculated by performing structure optimization using B3LYP / 6-31G * as a keyword is shown.

<< Evaluation of Organic EL Elements 1-1 to 1-13 >>
When evaluating the obtained organic EL elements 1-1 to 1-13, the non-light-emitting surface of each organic EL element after production is covered with a glass cover, and the glass cover and the glass plate on which the organic EL element is produced are prepared. An epoxy-based photo-curing adhesive (Luxtrac LC0629B manufactured by Toagosei Co., Ltd.) is applied as a sealant around the glass cover side that comes into contact with the transparent support substrate so as to overlap the cathode side, and the glass substrate side. Then, it was cured by irradiating with UV light and sealed, and the lighting device as shown in FIGS. 5 and 6 was formed and evaluated. Subsequently, the following evaluation was performed.

(External quantum efficiency)
By causing the organic EL device to emit light at room temperature (about 23 ° C. to 25 ° C.) and a constant current of ^2.5 mA / cm ² , and measuring the light emission luminance (L) [cd / m ² ] immediately after the start of light emission, The external extraction quantum efficiency (η) was calculated. Here, CS-1000 (manufactured by Konica Minolta Sensing) was used for measurement of light emission luminance.

(Drive voltage)
The voltage was measured when the organic EL device was driven at room temperature (about 23 ° C. to 25 ° C.) under a constant current condition of ^2.5 mA / cm ² .

(Luminescent life)
The organic EL device continuously emitted light at room temperature under a constant current condition of ^2.5 mA / cm ² , and the time (τ1 / 2) required to obtain half the initial luminance was measured. The external extraction quantum efficiency, drive voltage, and light emission lifetime are expressed as relative values at which the organic EL element 1-13 is set to 100. The results obtained are shown below.

(Green light-emitting organic EL device)
As the green light-emitting organic EL element, the organic EL element 1-1 produced in Example 2 was used.

(Red light emitting organic EL device)
A red light emitting organic EL element 3-1R was produced in the same manner as in the production of the organic EL element 1-1 of Example 2, except that Ir (ppy) ₃ was changed to D-10.

  The above red, green and blue light emitting organic EL elements are juxtaposed on the same substrate to produce an active matrix type full color display device having the form shown in FIG. 1, and FIG. 2 shows a display portion of the produced display device. Only the schematic diagram of A is shown. That is, a wiring portion including a plurality of scanning lines 5 and data lines 6 on the same substrate, and a plurality of juxtaposed pixels 3 (light emission color is a red region pixel, a green region pixel, a blue region pixel, etc.) The scanning lines 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 lattice shape and are connected to the pixels 3 at the orthogonal positions ( Details are not shown). The plurality of pixels 3 are driven by an active matrix system provided with an organic EL element corresponding to each emission color, a switching transistor as an active element, and a driving transistor, and a scanning signal is applied from a scanning line 5. Then, an image data signal is received from the data line 6 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.

  It was confirmed that by driving the full-color display device, a full-color moving image display having a high light emission efficiency and a long light emission life can be obtained.

Example 4
(Production of white light emitting lighting device)
In the production of the organic EL element 2-1B produced in Example 3, the white light-emitting organic EL element 4-1W was similarly obtained except that D-26 was changed to Ir (ppy) 3, D-10, and D-26. Was made. The obtained organic EL device 4-1W was covered with a glass case on the non-light-emitting surface in the same manner as in the above example to obtain a lighting device. The illuminating device could be used as a thin illuminating device that emits white light with high luminous efficiency and long emission life.

DESCRIPTION OF SYMBOLS 1 Display 3 Pixel 5 Scan line 6 Data line 7 Power supply line 10 Organic EL element 11 Switching transistor 12 Drive transistor 13 Capacitor A Display part B Control part 101 Organic EL element 102 Glass cover 105 Cathode 106 Organic EL layer 107 Glass substrate with a transparent electrode 108 Nitrogen gas 109 Water trapping agent 201 Glass substrate 202 ITO transparent electrode 203 Partition wall 204 Hole injection layer 205B, 205G, 205R Light emitting layer

Claims (11)

The organic electronic device material used for the light emitting layer of the organic electronic device having at least an anode, an organic light emitting layer, and a cathode on the support substrate is a cyclic silicon compound represented by the following general formula (1). A characteristic material for organic electronics elements.

(Wherein X1 and X2 represent a substituted or unsubstituted arylene or heteroarylene group, and R _{1 to} R ₈ are a hydrogen atom, a halogen atom, a nitro group, a cyano group or a substituted, unsubstituted amino group, an alkyl group, Represents an alkoxy group, an aryl group, or a heteroaryl group.)   The organic electronic device material according to claim 1, wherein a band gap between the ground state and the triplet excited state of the cyclic silicon compound is 2.1 eV or more and 3.8 eV or less.   The organic electronic device material according to claim 1 or 2, wherein a band gap between the ground state and the triplet excited state of the cyclic silicon compound is 2.7 eV or more and 3.8 eV or less. The organic electronic device according to any one of claims 1 to 3, wherein X1 or X2 in the general formula (1) is any one selected from the following general formulas (2) to (5). Materials.

(In the formula, two arbitrary hydrogen atoms are linking groups. Y _{1 to} Y ₅ represent NR, O, S, BR, CRR ′ or SiRR ′, and R and R ′ each represent a hydrogen atom or a substituent. Z _{1 to} Z ₁₀ each represent N or CR, and each R represents a hydrogen atom or a substituent, provided that at least one of Z _{1 to} Z ₁₀ is N).   In the organic electronics element which has an anode, the light emitting layer which consists of an organic substance, and a cathode on a support substrate, this light emitting layer contains the organic electronics element material of any one of Claims 1-4. Features organic electronics elements.   6. The organic electronics element according to claim 5, wherein the light emitting material contained in the light emitting layer is a phosphorescent light emitting material.   The organic electronic device according to claim 6, wherein the phosphorescent material is an Ir complex.   The organic electronic device according to claim 7, wherein the band gap between the ground state and the triplet excited state of the Ir complex is 2.7 eV or more and 3.8 eV or less.   The organic electronic device according to claim 5, which emits white light.   A lighting device comprising the organic electronics element according to claim 5.   A display device comprising the organic electronics element according to claim 5.

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