JP2008270729A - Organic electroluminescence element - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an organic electroluminescence element that exhibits high light-emission efficiency and is excellent in durability. <P>SOLUTION: The organic electroluminescence element has at least one organic layer including a light-emitting layer between a pair of electrodes; and an electron transport layer containing a phosphine oxide compound and an electron transport layer that does not substantially contain the phosphine oxide compound between the light-emitting layer and a cathode, wherein the electron transport layer containing the phosphine oxide compound is nearer to the cathode, and the electron transport layer that does not substantially contain the phosphine oxide compound is nearer to the light-emitting layer. <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

  The present invention relates to an organic electroluminescent element (hereinafter sometimes referred to as an organic EL element) that can be effectively used for a surface light source such as a full color display, a backlight, and an illumination light source, and a light source array such as a printer.

  The organic EL element is composed of a light emitting layer or a plurality of organic layers including a light emitting layer and a counter electrode sandwiching the organic layer. In the organic EL element, electrons injected from the cathode and holes injected from the anode are recombined in the organic layer, emitted light from the generated excitons, and other molecules generated by energy transfer from the excitons. It is an element for obtaining light emission using at least one of light emission from the excitons.

  Until now, organic EL elements have been developed with greatly improved brightness and element efficiency by using a laminated structure with separated functions. For example, a two-layer stacked device in which a hole transport layer and a light-emitting / electron transport layer are stacked, a three-layer stacked device in which a hole transport layer, a light-emitting layer, and an electron transport layer are stacked, a hole transport layer, and a light-emitting layer A four-layer stacked element in which a hole blocking layer and an electron transport layer are stacked is often used.

  However, many problems still remain in practical use of organic EL elements, such as improving luminous efficiency and driving durability. In particular, increasing the light emission efficiency can reduce power consumption and is advantageous in terms of driving durability. Therefore, many improvement means have been disclosed so far. However, in general, a light emitting material with high luminous efficiency has a defect of causing luminance deterioration during driving, and a material with excellent driving durability has a defect of low luminance, which improves luminous efficiency and driving durability. It is not easy to achieve both enhancements, and further improvements are being sought.

Among them, the search for a hole transport material for promoting hole injection and hole transport from the anode and an electron transport material for promoting electron injection and electron transport from the cathode has been advanced. In particular, there is a demand for an electron transport material that can quickly inject electrons from a cathode and has excellent electron transport properties. For example, a phosphine oxide compound is known as an electron transport material having excellent electron transport properties (see, for example, Patent Document 1) However, there is an electron injection barrier from the cathode including the phosphine oxide compound. A small electron transport material with high electron mobility has a problem of low driving durability.
On the other hand, a search for a light emitting material having high light emission efficiency is also in progress. For example, since a phosphine oxide compound is excellent in electron injecting property and transporting property, it is disclosed that use in a light emitting layer is expected to improve luminous efficiency and lower voltage (for example, Patent Document 2, Non-Patent Document 2). (See Patent Document 1). However, when a phosphine oxide compound is used as the host material of the light emitting layer, the phosphine oxide compound deteriorates during continuous driving and loses its function as a host material, so that there is a problem that driving durability is remarkably deteriorated.
Therefore, development of an organic EL element having high luminous efficiency and excellent driving durability is demanded.
JP 2006-73581 A Japanese Patent Application Laid-Open No. 2002-63989 "New Charge Transforming Host Material for Short Wavelength Organic Electrophoresis: 2, 7-Bis (diphenylphosphine oxide) -9, 9-dimethyl-fluor." Mater. , 18, page 2389-2396 (2006).

  An object of the present invention is to provide an organic electroluminescent device exhibiting high luminous efficiency and excellent durability.

The present invention has been made in view of the above problems, and is achieved by the following means.
<1> An organic electroluminescence device having at least one organic layer including a light emitting layer between a pair of electrodes, the electron transport layer containing a phosphine oxide compound between the light emitting layer and the cathode, and the phosphine oxide An electron transport layer substantially free of a compound, the electron transport layer containing the phosphine oxide compound is close to the cathode, and the electron transport layer substantially free of the phosphine oxide compound is in the light emitting layer. An organic electroluminescence device characterized by being close to each other.
<2> The organic electroluminescent element according to <1>, wherein the electron transport layer containing the phosphine oxide is a layer in contact with the electron injection layer.
<3> The organic electroluminescence device according to <1> or <2>, wherein the electron transport layer containing the phosphine oxide has a thickness of 0.01 nm to 10 nm.
<4> The organic electroluminescence device according to <3>, wherein the electron transport layer containing the phosphine oxide has a thickness of 0.01 nm to 5 nm.
<5> The organic electroluminescent element according to any one of <1> to <4>, wherein the phosphine oxide compound is a compound represented by the following general formula (I):

Wherein R ¹ , R ² and R ³ are each independently an alkyl group, alkenyl group, alkynyl group, aryl group, amino group, alkoxy group, aryloxy group, heterocyclic oxy group, acyl group, alkoxycarbonyl Group, aryloxycarbonyl group, acyloxy group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group, arylthio group, heterocyclic thio group, or heterocyclic group To express.).
<6> The organic electroluminescent element according to <5>, wherein the phosphine oxide compound represented by the general formula (I) is a compound represented by the following general formula (II):

(In the formula, Ar ¹ , Ar ² , and Ar ³ each independently represents an aryl group or a heterocyclic group).
<7> The organic luminescence device according to any one of <1> to <4>, wherein the phosphine oxide compound is a compound represented by the following general formula (III):

(In the formula, R ^{21 to} R ²⁴ each independently represents an aryl group or a heterocyclic group. L represents a divalent linking group).
<8> The organic electroluminescent element according to any one of <1> to <7>, wherein the light emitting layer contains a phosphorescent material.
<9> The organic electroluminescent element according to <8>, wherein the phosphorescent material is an organometallic complex having platinum as a central metal.
<10> The organic electroluminescent element according to any one of <1> to <9>, wherein the light emitting layer contains a hole transporting organic material as a host material.

  ADVANTAGE OF THE INVENTION According to this invention, the organic electroluminescent element which shows high luminous efficiency and was excellent in durability is provided.

Hereinafter, the organic electroluminescent element of the present invention (hereinafter sometimes referred to as “organic EL element” as appropriate) will be described in detail.
The light-emitting element of the present invention has a cathode and an anode on a substrate, and an organic compound layer including an organic light-emitting layer (hereinafter sometimes simply referred to as “light-emitting layer”) between both electrodes. In view of the properties of the light emitting element, at least one of the anode and the cathode is preferably transparent.
The organic compound layer in the present invention may be either a single layer or a laminate. As an aspect in the case of lamination, an aspect in which a hole transport layer, a light emitting layer, and an electron transport layer are laminated in this order from the anode side is preferable. Further, a charge blocking layer or the like may be provided between the hole transport layer and the light-emitting layer, or between the light-emitting layer and the electron transport layer. A hole injection layer may be provided between the anode and the hole transport layer, and an electron injection layer may be provided between the cathode and the electron transport layer. Each layer may be divided into a plurality of secondary layers.

1. Description of Phosphine Oxide Compound Next, the phosphine oxide compound used in the organic electroluminescence device of the present invention will be described in detail.
The phosphine oxide compound used in the present invention is preferably a compound represented by the following general formula (I).

In the formula, R ¹ , R ² , and R ³ are each independently an alkyl group, alkenyl group, alkynyl group, aryl group, amino group, alkoxy group, aryloxy group, heterocyclic oxy group, acyl group, alkoxycarbonyl group , Aryloxycarbonyl group, acyloxy group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group, arylthio group, heterocyclic thio group, or heterocyclic group .

  Preferably, it is a phosphine oxide compound represented by the following general formula (II).

In the formula, Ar ¹ , Ar ² , and Ar ³ each independently represent an aryl group or a heterocyclic group.

  Another preferred group of phosphine oxide compounds in the present invention is a compound represented by the following general formula (III).

In the formula, R ^{31 to} R ³⁴ each independently represents an aryl group or a heterocyclic group. L represents a divalent linking group.

The general formula (I) will be described.
R ¹ , R ² and R ³ are alkyl groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms such as methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, Particularly preferably, it has 2 to 10 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl, and 3-pentenyl.), An alkynyl group (preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms). , Particularly preferably having 2 to 10 carbon atoms, such as propargyl and 3-pentynyl).

An aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms, such as phenyl, p-methylphenyl, naphthyl, and anthryl); An amino group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, and And dtolylamino), an alkoxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy, and 2-ethyl). Hexyloxy, etc.), aryloxy groups (preferably having 6 to 30 carbon atoms, more preferred) Ku 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenyloxy, 1-naphthyloxy, and 2-naphthyloxy and the like.),

Heterocyclic oxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, and examples thereof include pyridyloxy, pyrazyloxy, pyrimidyloxy, and quinolyloxy). An acyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include acetyl, benzoyl, formyl, and pivaloyl), an alkoxycarbonyl group. (Preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 12 carbon atoms. Examples thereof include methoxycarbonyl and ethoxycarbonyl).

An aryloxycarbonyl group (preferably having a carbon number of 7 to 30, more preferably a carbon number of 7 to 20, particularly preferably a carbon number of 7 to 12, such as phenyloxycarbonyl), an acyloxy group (preferably carbon 2 to 30, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetoxy and benzoyloxy), acylamino group (preferably 2 to 30 carbon atoms, more preferably Has 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include acetylamino, benzoylamino and the like, and an alkoxycarbonylamino group (preferably 2 to 30 carbon atoms, more preferably 2 carbon atoms). -20, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino Is.), An aryloxycarbonylamino group (preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, e.g., phenyloxycarbonylamino and the like.),

A sulfonylamino group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonylamino), a sulfamoyl group ( Preferably it is C0-30, More preferably, it is C0-20, Most preferably, it is C0-12, for example, sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl, etc. are mentioned. ), A carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include carbamoyl, methylcarbamoyl, diethylcarbamoyl, and phenylcarbamoyl. ), An alkylthio group (preferably having a carbon number of 1 to 0, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio and ethylthio, and arylthio groups (preferably 6 to 30 carbon atoms, more preferably 6 carbon atoms). To 20 and particularly preferably 6 to 12 carbon atoms, such as phenylthio).

Heterocyclic thio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, And 2-benzthiazolylthio and the like.

Or a heterocyclic group (preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom, specifically imidazolyl, pyridyl, Quinolyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl group, azepinyl group, etc.), silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 carbon atoms) To 30 and particularly preferably 3 to 24 carbon atoms such as trimethylsilyl and triphenylsilyl), silyloxy groups (preferably 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms such as trimethylsilyloxy, triphenylsilyloxy And the like.), Or a phosphoryl group (e.g., diphenylphosphoryl, dimethyl phosphoryl and the like.).

The groups represented by R ¹ , R ² and R ³ may be the same as or different from each other. The substituent represented by R ¹ , R ² and R ³ is preferably an alkyl group, an alkenyl group, an alkynyl group, an aryl group or a heterocyclic group, more preferably an alkyl group, an aryl group or a heterocyclic group. And particularly preferably an aryl group or a heterocyclic group.

The substituent represented by R ¹ , R ² and R ³ may further have a substituent, and as the substituent, an alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 1 carbon atom). 20, Particularly preferably, it has 1 to 10 carbon atoms, and examples thereof include methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, and cyclohexyl. ), An alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl, and 3-pentenyl. ),

Alkynyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as propargyl, 3-pentynyl, etc.), aryl group (preferably carbon 6 to 30, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenyl, p-methylphenyl, naphthyl, and anthryl.), Amino group (preferably carbon It has 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, and particularly preferably 0 to 10 carbon atoms. Examples thereof include amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, and ditolylamino. ), An alkoxy group (preferably having 1 to 30 carbon atoms, more preferably having 1 to 20 carbon atoms, particularly preferred) Has 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy, and 2-ethylhexyloxy), an aryloxy group (preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, Particularly preferably, it has 6 to 12 carbon atoms, and examples thereof include phenyloxy, 1-naphthyloxy, 2-naphthyloxy and the like, and a heterocyclic oxy group (preferably having 1 to 30 carbon atoms, more preferably having carbon atoms). 1 to 20, particularly preferably 1 to 12 carbon atoms, such as pyridyloxy, pyrazyloxy, pyrimidyloxy and quinolyloxy), acyl groups (preferably 1 to 30 carbon atoms, more preferably 1 to 1 carbon atoms). 20, particularly preferably having 1 to 12 carbon atoms, such as acetyl, benzoyl, formyl, and pivaloyl Etc., and the like.),

An alkoxycarbonyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, etc.), an aryloxycarbonyl group ( Preferably it has 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, and examples thereof include phenyloxycarbonyl, etc.), an acyloxy group (preferably 2 to 30 carbon atoms, More preferably, it has 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include acetoxy and benzoyloxy.), Acylamino group (preferably 2 to 30 carbon atoms, more preferably 2 to 2 carbon atoms). 20, particularly preferably 2 to 10 carbon atoms, such as acetylamino, benzoylamino An alkoxycarbonylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino). Aryloxycarbonylamino group (preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonylamino), sulfonylamino group ( Preferably it is C1-C30, More preferably, it is C1-C20, Most preferably, it is C1-C12, for example, methanesulfonylamino, benzenesulfonylamino, etc. are mentioned.

Sulfamoyl group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 12 carbon atoms, such as sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl, etc. ), A carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl, etc. An alkylthio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms such as methylthio and ethylthio), an arylthio group. (Preferably 6 to 30 carbon atoms, more preferably 6 to 6 carbon atoms. 0, particularly preferably 6 to 12 carbon atoms, such as phenylthio, etc.), a heterocyclic thio group (preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 carbon atom). -12, and examples thereof include pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, and 2-benzthiazolylthio).

A sulfonyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as mesyl and tosyl), a sulfinyl group (preferably having 1 carbon atom). To 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfinyl, benzenesulfinyl, etc.), ureido groups (preferably 1 to 30 carbon atoms, more preferably C1-C20, Most preferably, it is C1-C12, for example, ureido, methylureido, phenylureido etc. are mentioned), phosphoric acid amide groups (preferably C1-C30, more preferably carbon 1 to 20, particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide and phenyl phosphoric acid amide. Hydroxy group, mercapto group, fluoro group, chloro group, bromo group, iodo group, cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, heterocyclic group (Preferably having 1 to 30 carbon atoms, more preferably having 1 to 12 carbon atoms, and the hetero atom is, for example, a nitrogen atom, an oxygen atom, or a sulfur atom, specifically imidazolyl, pyridyl, quinolyl, furyl, Thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl group, azepinyl group and the like.

A silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, such as trimethylsilyl, triphenylsilyl, etc.), a silyloxy group (preferably carbon 3 to 40, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, for example, trimethylsilyloxy, triphenylsilyloxy, etc.) or phosphoryl group (for example, diphenylphosphoryl, dimethylphosphoryl) Etc.) can be applied.

The substituent represented by the group represented by R ¹ , R ² and R ³ is preferably an alkyl group, alkenyl group, alkynyl group, aryl group, amino group, alkoxy group, aryloxy group, heterocyclic oxy group, alkylthio group. , Arylthio group, heterocyclic thio group, sulfonyl group, sulfinyl group, fluoro group, chloro group, bromo group, iodo group, cyano group, heterocyclic group, silyl group, silyloxy group, or phosphoryl group, more preferably alkyl Group, alkenyl group, aryl group, amino group, alkoxy group, aryloxy group, heterocyclic oxy group, sulfonyl group, fluoro group, cyano group, heterocyclic group, silyl group, silyloxy group, or phosphoryl group, more preferably Is an alkyl group, aryl group, amino group, fluoro group, cyano group, heterocyclic group, Ryl group or phosphoryl group, more preferably an alkyl group, an aryl group, a cyano group, a heterocyclic group, or a phosphoryl group.

  The compound represented by the general formula (I) is more preferably a compound represented by the general formula (II).

In the formula, Ar ¹ , Ar ² , and Ar ³ each independently represent an aryl group or a heterocyclic group.

  Next, general formula (II) will be described.

In the formula, Ar ¹ , Ar ² , and Ar ³ represent a substituted or unsubstituted aryl group or heterocyclic group. Examples of the aryl group represented by Ar ¹ , Ar ² , and Ar ³ include a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a fluoranthenyl group, a fluorenyl group, a chrysenyl group, a tetracenyl group, Examples include a pentacenyl group, a triphenylenyl group, and a tetraphenylenyl group. These aryl groups may have a substituent, and examples of the substituent include those listed as the substituents of the groups represented by R ¹ , R ² and R ³ in the general formula (I). The preferred range is also the same.

Heteroaryl groups represented by Ar ¹ , Ar ² , and Ar ³ include pyridyl group, pyrazinyl group, triazinyl group, pyrimidinyl group, pyridazinyl group, quinolyl group, quinoxalinyl group, phthalazinyl group, quinazolinyl group, cinnolinyl group, isoquinolyl group Group, acridinyl group, phenanthridinyl group, phenanthrolinyl group, pteridinyl group, imidazolidyl group, pyrrolyl group, indolyl group, pyrazolyl group, indazolyl group, imidazolyl group, benzimidazolyl group, carbazolyl group, carbolinyl group, purinyl group , Furyl group, thienyl group, isoxazolyl group, isothiazolyl group, oxazolyl group, thiazolyl group, benzoxazolyl group, benzothiazolyl group, indolizinyl group, benzoquinolinyl group, quinolidinyl group, triazolyl , Benzotriazolyl group, and the like naphthyridinyl group. These heteroaryl groups may have a substituent, and examples of the substituent include those listed as the substituents of the groups represented by R ¹ , R ² and R ³ in the general formula (I). The applicable range is also the same.

As the group represented by Ar ¹ , Ar ² , and Ar ³ , a substituted or unsubstituted phenyl group, naphthyl group, anthryl group, phenanthryl group, pyrenyl group, fluorenyl group, pyridyl group, pyrazinyl group, quinolyl group, A quinoxalinyl group, an acridinyl group, a phenanthrolinyl group, or a benzoquinolinyl group, more preferably a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a pyridyl group, a pyrazinyl group, a quinolyl group, a phenanthrolinyl group Or a benzoquinolinyl group.

A more preferred group of phosphine oxide compounds in the present invention are compounds represented by the general formula (III).

In formula, R < ³¹ > -R < ³⁴ > represents an aryl group or a heterocyclic group each independently. L represents a divalent linking group.

  Next, general formula (III) will be described.

In general formula (III), the aryl group or heterocyclic group represented by R ^{31 to} R ³⁴ has the same meaning as the aryl group or heterocyclic group described for R ^{1 to} R ³ in general formula (I), and The preferable range is also the same. L represents a divalent linking group. The divalent linking group is not particularly limited, but is preferably a linking group comprising a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, or a halogen atom, more preferably a carbon atom, a nitrogen atom, or a silicon atom. A linking group.

  The divalent linking group represented by L is preferably p-phenylene, m-phenylene, o-phenylene, biphenyldiyl, naphthalenediyl, fluorenediyl, dibenzofurandyl, pyridinediyl, or pyrazinediyl, more preferably Biphenyldiyl, fluorenediyl, pyridinediyl, or pyrazinediyl.

  Specific examples of the phosphine oxide compound used in the present invention are given below, but the compound of the present invention is not limited thereto.

  Specific examples of the phosphine oxide compound used in the present invention include the compounds exemplified in Compound Paragraph Nos. 5 to 7 described in JP-A No. 2002-63989, for example.

<How to use>
In the present invention, a method for forming a layer containing a phosphine oxide compound is not particularly limited, but a resistance heating vapor deposition method, an electron beam method, a sputtering method, a molecular lamination method, a wet coating method (spray coating method, Dip coating method, impregnation method, roll coating method, gravure coating method, reverse coating method, roll brush method, air knife coating method, curtain coating method, spin coating method, flow coating method, bar coating method, micro gravure coating method, air Doctor coating, blade coating method, squeeze coating method, transfer roll coating method, kiss coating method, cast coating method, extrusion coating method, wire bar coating method, screen coating method, etc.), inkjet method, printing method, transfer method, etc. The method is used.

2. Organic Electroluminescent Device Hereinafter, the configuration of the organic electroluminescent device of the present invention will be described in detail.
The light emitting device of the present invention is an organic electroluminescent device having a cathode and an anode on a substrate, and an organic layer including an organic light emitting layer (hereinafter sometimes simply referred to as “light emitting layer”) between both electrodes. An electron transport layer having an electron transport layer containing a phosphine oxide compound and an electron transport layer substantially free of the phosphine oxide compound between the light emitting layer and the cathode, and containing the phosphine oxide compound A layer is close to the cathode, and an electron transport layer substantially free of the phosphine oxide compound is close to the light emitting layer. In view of the properties of the light emitting element, at least one of the anode and the cathode is preferably transparent.
Preferably, the electron transport layer containing the phosphine oxide is a layer in contact with the electron injection layer.

  As an aspect of lamination of the organic layer in the present invention, an aspect in which a hole transport layer, a light emitting layer, and an electron transport layer are laminated in this order from the anode side is preferable. Further, a charge blocking layer or the like may be provided between the hole transport layer and the light-emitting layer, or between the light-emitting layer and the electron transport layer. A hole injection layer may be provided between the anode and the hole transport layer, and an electron injection layer may be provided between the cathode and the electron transport layer. Each layer may be divided into a plurality of secondary layers.

Next, the elements constituting the light emitting material of the present invention will be described in detail.
<Board>
The substrate used in the present invention is preferably a substrate that does not scatter or attenuate light emitted from the organic compound layer. Specific examples thereof include zirconia stabilized yttrium (YSZ), inorganic materials such as glass, polyesters such as polyethylene terephthalate, polybutylene phthalate, and polyethylene naphthalate, polystyrene, polycarbonate, polyethersulfone, polyarylate, polyimide, and polycycloolefin. , Norbornene resins, and organic materials such as poly (chlorotrifluoroethylene).
For example, when glass is used as the substrate, it is preferable to use non-alkali glass as the material in order to reduce ions eluted from the glass. Moreover, when using soda-lime glass, it is preferable to use what gave barrier coatings, such as a silica. In the case of an organic material, it is preferable that it is excellent in heat resistance, dimensional stability, solvent resistance, electrical insulation, and workability.

  There is no restriction | limiting in particular about the shape of a board | substrate, a structure, a magnitude | size, It can select suitably according to the use, purpose, etc. of a light emitting element. In general, the shape of the substrate is preferably a plate shape. The structure of the substrate may be a single layer structure, a laminated structure, may be formed of a single member, or may be formed of two or more members.

  The substrate may be colorless and transparent or colored and transparent, but is preferably colorless and transparent in that it does not scatter or attenuate light emitted from the organic light emitting layer.

The substrate can be provided with a moisture permeation preventing layer (gas barrier layer) on the front surface or the back surface.
As a material for the moisture permeation preventive layer (gas barrier layer), inorganic materials such as silicon nitride and silicon oxide are preferably used. The moisture permeation preventing layer (gas barrier layer) can be formed by, for example, a high frequency sputtering method.
When a thermoplastic substrate is used, a hard coat layer, an undercoat layer, or the like may be further provided as necessary.

<Anode>
The anode usually has a function as an electrode for supplying holes to the organic compound layer, and there is no particular limitation on the shape, structure, size, etc., depending on the use and purpose of the light-emitting element. , Can be appropriately selected from known electrode materials. As described above, the anode is usually provided as a transparent anode.

  Suitable examples of the material for the anode include metals, alloys, metal oxides, conductive compounds, and mixtures thereof. Specific examples of the anode material include conductive metals such as tin oxide (ATO, FTO) doped with antimony or fluorine, tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc. Metals such as oxides, gold, silver, chromium, nickel, and mixtures or laminates of these metals and conductive metal oxides, inorganic conductive materials such as copper iodide and copper sulfide, polyaniline, polythiophene, polypyrrole, etc. Organic conductive materials, and a laminate of these and ITO. Among these, conductive metal oxides are preferable, and ITO is particularly preferable from the viewpoints of productivity, high conductivity, transparency, and the like.

  The anode is composed of, for example, a wet method such as a printing method and a coating method, a physical method such as a vacuum deposition method, a sputtering method, and an ion plating method, and a chemical method such as a CVD and a plasma CVD method. It can be formed on the substrate according to a method appropriately selected in consideration of suitability with the material to be processed. For example, when ITO is selected as the anode material, the anode can be formed according to a direct current or high frequency sputtering method, a vacuum deposition method, an ion plating method, or the like.

  In the organic electroluminescent element of the present invention, the formation position of the anode is not particularly limited and can be appropriately selected according to the use and purpose of the light emitting element. Is preferably formed on the substrate. In this case, the anode may be formed on the entire one surface of the substrate, or may be formed on a part thereof.

  The patterning for forming the anode may be performed by chemical etching such as photolithography, or may be performed by physical etching such as laser, or vacuum deposition or sputtering with a mask overlapped. It may be performed by a lift-off method or a printing method.

  The thickness of the anode can be appropriately selected depending on the material constituting the anode and cannot be generally defined, but is usually about 10 nm to 50 μm, and preferably 50 nm to 20 μm.

The resistance value of the anode is preferably 10 ³ Ω / □ or less, and more preferably 10 ² Ω / □ or less. When the anode is transparent, it may be colorless and transparent or colored and transparent. In order to take out light emission from the transparent anode side, the transmittance is preferably 60% or more, and more preferably 70% or more.

  The transparent anode is described in detail in the book “New Development of Transparent Electrode Films” published by CMC (1999), supervised by Yutaka Sawada, and the matters described here can be applied to the present invention. In the case of using a plastic substrate having low heat resistance, a transparent anode formed using ITO or IZO at a low temperature of 150 ° C. or lower is preferable.

<Cathode>
The cathode usually has a function as an electrode for injecting electrons into the organic compound layer, and there is no particular limitation on the shape, structure, size, etc., depending on the use and purpose of the light-emitting element, It can select suitably from well-known electrode materials.

  Examples of the material constituting the cathode include metals, alloys, metal oxides, electrically conductive compounds, and mixtures thereof. Specific examples include alkali metals (eg, LI, Na, K, or Cs), alkaline earth metals (eg, Mg, Ca, etc.), gold, silver, lead, aluminum, sodium-potassium alloys, lithium-aluminum alloys, And a rare earth metal such as magnesium-silver alloy, indium, and ytterbium. These may be used alone, but two or more can be suitably used in combination from the viewpoint of achieving both stability and electron injection.

Among these, as a material constituting the cathode, an alkali metal or an alkaline earth metal is preferable from the viewpoint of electron injecting property, and a material mainly composed of aluminum is preferable from the viewpoint of excellent storage stability.
The material mainly composed of aluminum is aluminum alone, an alloy of aluminum and 0.01% by mass to 10% by mass of alkali metal or alkaline earth metal, or a mixture thereof (for example, lithium-aluminum alloy or magnesium-aluminum). Alloy).

  The cathode materials are described in detail in JP-A-2-15595 and JP-A-5-121172, and the materials described in these publications can also be applied in the present invention.

There is no restriction | limiting in particular about the formation method of a cathode, According to a well-known method, it can carry out.
For example, the cathode described above is configured from a wet method such as a printing method or a coating method, a physical method such as a vacuum deposition method, a sputtering method, or an ion plating method, or a chemical method such as CVD or plasma CVD method. It can be formed according to a method appropriately selected in consideration of suitability with the material. For example, when a metal or the like is selected as the cathode material, one or more of them can be simultaneously or sequentially performed according to a sputtering method or the like.

  Patterning when forming the cathode may be performed by chemical etching such as photolithography, physical etching by laser, or the like, or by vacuum deposition or sputtering with the mask overlaid. It may be performed by a lift-off method or a printing method.

In the present invention, the cathode formation position is not particularly limited, and may be formed on the entire organic compound layer or a part thereof.
Further, a dielectric layer made of an alkali metal or alkaline earth metal fluoride or oxide may be inserted between the cathode and the organic compound layer with a thickness of 0.1 nm to 5 nm. This dielectric layer can also be regarded as a kind of electron injection layer. The dielectric layer can be formed by, for example, a vacuum deposition method, a sputtering method, an ion plating method, or the like.

The thickness of the cathode can be appropriately selected depending on the material constituting the cathode and cannot be generally defined, but is usually about 10 nm to 5 μm, and preferably 50 nm to 1 μm.
Further, the cathode may be transparent or opaque. The transparent cathode can be formed by depositing a thin cathode material to a thickness of 1 nm to 10 nm and further laminating a transparent conductive material such as ITO or IZO.

<Organic compound layer>
The organic compound layer in the present invention will be described.
The organic electroluminescent element of the present invention has at least one organic compound layer including a light emitting layer, and the organic compound layer other than the organic light emitting layer includes a hole transport layer, an electron transport layer as described above. , Charge blocking layer (hole blocking layer, electron blocking layer), hole injection layer, electron injection layer, and the like.

  In the organic electroluminescence device of the present invention, each layer constituting the organic compound layer is suitably formed by any of dry film forming methods such as vapor deposition and sputtering, wet coating methods, transfer methods, printing methods, and ink jet methods. can do.

1) Organic light-emitting layer The organic light-emitting layer receives holes from the anode, hole injection layer, or hole transport layer and receives electrons from the cathode, electron injection layer, or electron transport layer when an electric field is applied. This layer has a function of emitting light by providing a recombination field of electrons.
The light emitting layer in the present invention preferably contains a host material and a light emitting material.
The light emitting material may be a fluorescent light emitting material or a phosphorescent light emitting material, and the dopant may be one type or two or more types, but in the present invention, the phosphorescent light emitting material is preferable. The light emitting material may be a low molecular compound or a high molecular compound.
The host material is preferably a charge transport material, and in the present invention, a hole transportable host material is particularly preferable. The host material may be one kind or two or more kinds. For example, a hole transporting host material may be mixed with an electron transporting host material. Further, the light emitting layer may include a material that does not have charge transporting properties and does not emit light.
Further, the light emitting layer may be a single layer or two or more layers, and each layer may emit light in different emission colors.

(Luminescent material)
Examples of fluorescent materials that can be used in the present invention include, for example, benzofuran derivatives, benzothiophene derivatives, pyran derivatives, benzoxazole derivatives, benzimidazole derivatives, benzothiazole derivatives, styrylbenzene derivatives, polyphenyl derivatives, diphenylbutadiene derivatives, tetra Phenylbutadiene derivatives, naphthalimide derivatives, coumarin derivatives, condensed aromatic compounds, perylene derivatives, oxadiazole derivatives, oxazine derivatives, aldazine derivatives, pyrazine derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives, quinacridone derivatives, pyrrolopyridine derivatives, thiols Asiazolopyridine derivatives, cyclopentadiene derivatives, styrylamine derivatives, diketopyrrolopyrrole derivatives, aromatic dimethylidin compounds , 8-quinolinol derivatives of various metal complexes typified by metal complexes of the metal complex and pyrromethene derivatives, polythiophene, polyphenylene, polyphenylene vinylene polymer compounds include compounds such as organic silane derivatives.

Examples of the phosphorescent material that can be used in the present invention include complexes containing transition metal atoms or lanthanoid atoms.
Although it does not specifically limit as a transition metal atom, Preferably, ruthenium, rhodium, palladium, tungsten, rhenium, osmium, iridium, and platinum are mentioned, More preferably, they are rhenium, iridium, and platinum. In the present invention, an organometallic complex having platinum as a central metal is particularly preferable.
Examples of lanthanoid atoms include lanthanum, cerium, praseodymium, neodymium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, and lutetium. Among these lanthanoid atoms, neodymium, europium, and gadolinium are preferable.

Examples of the ligand of the complex include G.I. Wilkinson et al., Comprehensive Coordination Chemistry, Pergamon Press, 1987, H.C. Examples include ligands described in Yersin's "Photochemistry and Photophysics of Coordination Compounds" published by Springer-Verlag 1987, Akio Yamamoto "Organic Metal Chemistry-Fundamentals and Applications-" .
The specific ligand is preferably a halogen ligand (preferably a chlorine ligand), an aromatic ligand (eg, cyclopentadienyl anion, benzene anion, naphthyl anion, etc.), nitrogen-containing hetero Ring ligands (eg, phenylpyridine, benzoquinoline, isoquinoline, quinolinol, bipyridyl, phenanthroline, etc.), diketone ligands (eg, acetylacetone), carboxylic acid ligands (eg, acetate ligand, picolinato, etc.) , A carbon monoxide ligand, an isonitrile ligand, and a cyano ligand, and more preferably a nitrogen-containing heterocyclic ligand. The complex may have one transition metal atom in the compound, or may be a so-called binuclear complex having two or more. Different metal atoms may be contained at the same time.

  The phosphorescent material is preferably contained in the light emitting layer in an amount of 0.1% by mass to 40% by mass, and more preferably 0.5% by mass to 30% by mass.

  Specific examples of the platinum complex used in the present invention are illustrated below, but the present invention is not limited thereto.

(Host material)
The host material in the present invention is not particularly limited, but the use of a hole transporting host material is particularly effective because it is highly effective.

《Hole-transporting host》
The hole transporting host used in the organic layer of the present invention preferably has an Ip of 5.1 eV or more and 6.3 eV or less from the viewpoint of improving durability and lowering driving voltage. More preferably, it is 5.6 eV or more and 5.8 eV or less. Further, from the viewpoint of improving durability and lowering driving voltage, the electron affinity Ea is preferably 1.2 eV or more and 3.1 eV or less, more preferably 1.4 eV or more and 3.0 eV or less, and 1.8 eV or more. More preferably, it is 2.8 eV or less.
Specific examples of such a hole transporting host include the following materials. Pyrrole, carbazole, pyrazole, imidazole, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, arylamine, amino-substituted chalcone, styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatic tertiary amine compound, styrylamine compound, aromatic Group dimethylidin compounds, porphyrin compounds, polysilane compounds, poly (N-vinylcarbazole), aniline copolymers, thiophene oligomer thiophene oligomers, conductive polymer oligomers such as polythiophene, organic silanes, carbon films, and their Derivatives and the like.
Specific examples of the hole transporting host include the following compounds, but the present invention is not limited thereto.

(Light emitting layer thickness)
Although the thickness of a light emitting layer is not specifically limited, Usually, it is preferable that they are 1 nm-500 nm, it is more preferable that they are 5 nm-200 nm, and it is still more preferable that they are 10 nm-100 nm.

2) Hole injection layer, hole transport layer The hole injection layer and the hole transport layer are layers having a function of receiving holes from the anode or the anode side and transporting them to the cathode side. The material that can be used for the hole injection layer and the hole transport layer of the present invention is not particularly limited, and may be a low molecular compound or a high molecular compound.
Specifically, pyrrole derivatives, carbazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives , Silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidin compounds, phthalocyanine compounds, porphyrin compounds, thiophene derivatives, organic silane derivatives, carbon, phenylazole, phenylazine A layer containing a metal complex or the like is preferable.

  An electron-accepting dopant can be contained in the hole injection layer or the hole transport layer of the organic EL device of the present invention. As the electron-accepting dopant introduced into the hole-injecting layer or the hole-transporting layer, an inorganic compound or an organic compound can be used as long as it has an electron-accepting property and oxidizes an organic compound.

  Specifically, examples of the inorganic compound include metal halides such as ferric chloride, aluminum chloride, gallium chloride, indium chloride, and antimony pentachloride, metal oxides such as vanadium pentoxide, and molybdenum trioxide.

In the case of an organic compound, a compound having a nitro group, halogen, cyano group, or trifluoromethyl group as a substituent, a quinone compound, an acid anhydride compound, or fullerene can be preferably used.
In addition, JP-A-6-212153, JP-A-11-111463, JP-A-11-251067, JP-A-2000-196140, JP-A-2000-286054, JP-A-2000-315580, JP-A-2001-102175, JP-A-2001-2001. -160493, JP2002-252085, JP2002-56985, JP2003-157981, JP2003-217862, JP2003-229278, JP2004-342614, JP2005-72012, JP20051666667 The compounds described in JP-A-2005-209643 and the like can be preferably used.

These electron-accepting dopants may be used alone or in combination of two or more.
Although the usage-amount of an electron-accepting dopant changes with kinds of material, it is preferable that it is 0.01 mass%-50 mass% with respect to hole transport layer material, and it is 0.05 mass%-20 mass%. It is further more preferable and it is especially preferable that it is 0.1 mass%-10 mass%.

The thicknesses of the hole injection layer and the hole transport layer are each preferably 500 nm or less from the viewpoint of lowering the driving voltage.
The thickness of the hole transport layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and still more preferably 10 nm to 100 nm. In addition, the thickness of the hole injection layer is preferably 0.1 nm to 200 nm, more preferably 0.5 nm to 100 nm, and still more preferably 1 nm to 100 nm.
The hole injection layer and the hole transport layer may have a single-layer structure composed of one or more of the materials described above, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions. .

3) Electron transport layer The electron transport layer is a layer having a function of receiving electrons from the cathode or the cathode side and transporting them to the anode side.
The electron transport layer in the present invention has an electron transport layer containing a phosphine oxide compound and an electron transport layer substantially free of a phosphine oxide compound, and the electron transport layer containing the phosphine oxide compound is close to the cathode. And the electron carrying layer which does not contain the said phosphine oxide compound substantially is adjoining to the light emitting layer, It is characterized by the above-mentioned. In the present invention, “proximity” means that one is relatively closer to the target layer than the other. In the present application, of the electron transport layer containing the phosphine oxide compound and the electron transport layer substantially free of the phosphine oxide compound, the layer substantially not containing the phosphine oxide compound is closer to the light emitting layer. It means that there is. That is, the electron transport layer containing the phosphine oxide compound is not close to the light emitting layer, and is closer to the cathode than the layer substantially not containing the phosphine oxide compound.
Preferably, an electron injection layer is provided between the cathode and the electron transport layer, and the electron transport layer containing the phosphine oxide compound is in contact with the electron injection layer.

  In the present invention, if the electron transport layer containing the phosphine oxide compound is located near the light emitting layer, the device durability is adversely affected. Therefore, the distance between the electron transport layer containing the phosphine oxide compound and the light emitting layer is For the purpose of separation, an “electron transport layer substantially free of a phosphine oxide compound” is provided. The electron transport layer substantially not containing a phosphine oxide compound is provided by employing an electron transport material other than phosphine oxide as a constituent material. In the electron transport layer substantially free of a phosphine oxide compound, the ratio of the phosphine oxide compound in the region from the light emitting layer side interface of the electron transport layer to 10% of the total thickness of the electron transport layer (up to 10% above) The amount of phosphine oxide compound in the region / the amount of phosphine oxide compound in the entire electron transport layer) is preferably 0.05 or less, more preferably 0.03 or less, and most preferably 0.01 or less. is there.

Preferably, the thickness of the electron transport layer containing the phosphine oxide compound is preferably 0.01 nm or more and 10 nm or less, and more preferably 0.01 nm or more and 5 nm or less. If it is less than 0.01 nm, it is not preferable in that it is difficult to obtain the effect of promoting electron injection, and if it exceeds 10 nm, the drive voltage may be increased or the durability may be deteriorated.
Preferably, the film thickness of the electron transport layer substantially free of a phosphine oxide compound is preferably 5 nm to 60 nm, and more preferably 10 nm to 30 nm. If it is less than 5 nm, it is not preferable in terms of durability, and if it exceeds 60 nm, it is not preferable in terms of driving voltage.

  The electron transport layer substantially free of phosphine oxide is not particularly limited, and a general electron transporting organic material can be used. For example, specifically, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimide derivatives, fluorenylidenemethane Derivatives, distyrylpyrazine derivatives, aromatic ring tetracarboxylic anhydrides such as naphthalene and perylene, phthalocyanine derivatives, 8-quinolinol metal complexes, metal phthalocyanines, metal complexes with benzoxazole and benzothiazole as ligands Various metal complexes, organosilane derivatives, and the like can be used.

The electron transport layer of the organic EL device of the present invention can contain an electron donating dopant. The electron-donating dopant introduced into the electron-transporting layer only needs to have an electron-donating property and reduce the organic compound, and includes alkali metals such as Li, alkaline earth metals such as Mg, and rare earth metals. Transition metals and reducing organic compounds are preferably used. As the metal, a metal having a work function of 4.2 eV or less can be preferably used. Specifically, Li, Na, K, Be, Mg, Ca, Sr, Ba, Y, Cs, La, Sm, Gd , And Yb. Examples of the reducing organic compound include nitrogen-containing compounds, sulfur-containing compounds, and phosphorus-containing compounds.
In addition, materials described in JP-A-6-212153, JP-A-2000-196140, JP-A-2003-68468, JP-A-2003-229278, JP-A-2004-342614, and the like can be used.

These electron donating dopants may be used alone or in combination of two or more.
The amount of the electron donating dopant varies depending on the type of material, but is preferably 0.1% by mass to 99% by mass, and 1.0% by mass to 80% by mass with respect to the electron transport layer material. Is more preferable, and 2.0 mass% to 70 mass% is particularly preferable.

4) Hole blocking layer The hole blocking layer is a layer having a function of preventing holes transported from the anode side to the light emitting layer from passing through to the cathode side. In the present invention, a hole blocking layer can be provided as an organic compound layer adjacent to the light emitting layer on the cathode side.
Examples of the compound constituting the hole blocking layer include aluminum complexes such as BAlq, triazole derivatives, phenanthroline derivatives such as BCP, and the like.
The thickness of the hole blocking layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and still more preferably 10 nm to 100 nm.
The hole block layer may have a single-layer structure made of one or more of the materials described above, or may have a multilayer structure made up of a plurality of layers having the same composition or different compositions.

5) Electron blocking layer The electron blocking layer is a layer having a function of preventing electrons transported from the cathode side to the light emitting layer from passing through to the anode side. In the present invention, an electron blocking layer can be provided as the organic compound layer adjacent to the light emitting layer on the anode side.
As examples of the compound constituting the electron blocking layer, for example, those mentioned as the hole transport material described above can be applied.
The thickness of the electron blocking layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100 nm.
The hole block layer may have a single-layer structure made of one or more of the materials described above, or may have a multilayer structure made up of a plurality of layers having the same composition or different compositions.
6) Electron Injection Layer In the present invention, it is preferable that an electron injection layer is provided between the cathode and the electron transport layer, and the electron transport layer containing the phosphine oxide compound is in contact with the electron injection layer.
The electron injection layer is a layer that facilitates injection of electrons from the cathode into the electron transport layer. Specifically, lithium salts such as lithium fluoride, lithium chloride, and lithium bromide, sodium fluoride, sodium chloride, fluoride An alkali metal salt such as cesium, an insulating metal oxide such as lithium oxide, aluminum oxide, indium oxide, or magnesium oxide can be preferably used.
The thickness of the electron injection layer is preferably 0.1 nm to 5 nm.

<Protective layer>
In the present invention, the entire organic EL element may be protected by a protective layer.
As a material contained in the protective layer, any material may be used as long as it has a function of preventing materials that promote device deterioration such as moisture and oxygen from entering the device.
Specific examples thereof include metals such as In, Sn, Pb, Au, Cu, Ag, Al, Ti, and Ni, MgO, SiO, SiO ₂ , Al ₂ O ₃ , GeO, NiO, CaO, BaO, and Fe _2. Metal oxides such as O ₃ , Y ₂ O ₃ , or TiO ₂ , metal nitrides such as SiN _x , SiN _x O _y , metal fluorides such as MgF ₂ , LiF, AlF ₃ , or CaF ₂ , polyethylene, polypropylene Polymethyl methacrylate, polyimide, polyurea, polytetrafluoroethylene, polychlorotrifluoroethylene, polydichlorodifluoroethylene, a copolymer of chlorotrifluoroethylene and dichlorodifluoroethylene, tetrafluoroethylene and at least one comonomer. A copolymer obtained by copolymerizing a monomer mixture containing Examples thereof include a fluorine-containing copolymer having a cyclic structure in the main chain, a water-absorbing substance having a water absorption of 1% or more, and a moisture-proof substance having a water absorption of 0.1% or less.

  The method for forming the protective layer is not particularly limited. For example, vacuum deposition, sputtering, reactive sputtering, MBE (molecular beam epitaxy), cluster ion beam, ion plating, plasma polymerization (high frequency) Excited ion plating method), plasma CVD method, laser CVD method, thermal CVD method, gas source CVD method, coating method, printing method, or transfer method can be applied.

<Sealing>
Furthermore, the organic electroluminescent element of this invention may seal the whole element using a sealing container.
Further, a moisture absorbent or an inert liquid may be sealed in a space between the sealing container and the light emitting element.
Although it does not specifically limit as a moisture absorber, For example, barium oxide, sodium oxide, potassium oxide, calcium oxide, sodium sulfate, calcium sulfate, magnesium sulfate, phosphorus pentoxide, calcium chloride, magnesium chloride, copper chloride Cesium fluoride, niobium fluoride, calcium bromide, vanadium bromide, molecular sieve, zeolite, magnesium oxide, and the like. The inert liquid is not particularly limited, and examples thereof include paraffins, liquid paraffins, fluorinated solvents such as perfluoroalkane, perfluoroamine, and perfluoroether, chlorinated solvents, and silicone oils. Can be mentioned.

<Drive>
The organic electroluminescence device of the present invention emits light by applying a direct current (which may include an alternating current component as necessary) voltage (usually 2 to 15 volts) or a direct current between the anode and the cathode. Obtainable. The driving method of the organic electroluminescence device of the present invention is described in JP-A-2-148687, JP-A-6-301355, JP-A-5-29080, JP-A-7-134558, JP-A-8-234658, and JP-A-8-2441047. The driving method described in each publication, Japanese Patent No. 2784615, US Pat. Nos. 5,828,429, 6023308, and the like can be applied.

  The light-emitting element of the present invention can improve the light extraction efficiency by various known devices. For example, by processing the substrate surface shape (for example, forming a fine concavo-convex pattern), controlling the refractive index of the substrate / ITO layer / organic layer, controlling the film thickness of the substrate / ITO layer / organic layer, etc. It is possible to improve light extraction efficiency and external quantum efficiency.

  The light-emitting element of the present invention may be a so-called top emission type in which light emission is extracted from the anode side.

(Use of the present invention)
The organic electroluminescent element of the present invention can be suitably used for a display element, a display, a backlight, an electrophotography, an illumination light source, a recording light source, an exposure light source, a reading light source, a sign, a signboard, an interior, or optical communication.

  The present invention will be specifically described using examples, but the present invention is not limited to these examples.

Example 1
(Production of organic EL element)
<Production of Comparative Organic EL Element 1>
1) Formation of anode An indium tin oxide film (hereinafter abbreviated as ITO) is deposited on a 25 mm × 25 mm × 0.7 mm glass substrate with a thickness of 150 nm (Tokyo Sanyo Vacuum Co., Ltd.). A transparent support substrate was used. This transparent support substrate was etched and washed.
2) Hole injection / transport layer 4,4-bis (N- (m-tolyl) -N-phenyl-amino) biphenyl (hereinafter abbreviated as TPD) was deposited on this ITO glass substrate at 50 nm.

3) Light-Emitting Layer On the hole injection / transport layer, 4,4′-di- (N-carbazole) -biphenyl (hereinafter abbreviated as CBP) as a host material and fac-tris (2-phenylpyridine) — A light emitting layer containing 6% by mass of N, C2 ′) iridium (III) (hereinafter abbreviated as Ir (ppy) ₃ ) with respect to CBP was deposited at 50 nm.

4) Electron transport layer On the light emitting layer, a phosphine oxide compound A-1 was deposited to a thickness of 50 nm.
5) Electron injection layer Furthermore, LiF was vapor-deposited with a film thickness of 0.5 nm.
6) Formation of cathode electrode A patterned mask (a mask having a light emitting area of 2 mm × 2 mm) was placed thereon, and aluminum was evaporated to a film thickness of about 200 nm to produce a device. The produced element was sealed in a dry glove box.
Said vapor deposition was performed in the vacuum of 10 < ^-3 > Pa-10 < ^-4 > Pa, and the substrate temperature on the conditions of room temperature.

<Preparation of the organic EL element 1 of the present invention>
In the production of the comparative organic EL element 1, the organic EL element 1 of the present invention was produced in the same manner as the production of the comparative organic EL element 1 except that the following two layers were used as the electron transport layer.
First electron transport layer: a layer close to the cathode.
The phosphine oxide compound A-1 was deposited to a thickness of 30 nm.
Second electron transport layer: a layer close to the light emitting layer.
Aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate (hereinafter abbreviated as BAlq) was deposited to a thickness of 20 nm.

<Preparation of the organic EL element 2 of the present invention>
In the production of the comparative organic EL element 1, the organic EL element 2 of the present invention was produced in exactly the same manner as the production of the comparative organic EL element 1 except that the following two layers were used as the electron transport layer.
First electron transport layer: a layer close to the cathode.
The phosphine oxide compound A-1 was deposited to a thickness of 10 nm.
Second electron transport layer: a layer close to the light emitting layer.
BAlq was deposited to a film thickness of 40 nm.

<Preparation of the organic EL element 3 of the present invention>
In the production of the comparative organic EL element 1, the organic EL element 3 of the present invention was produced in exactly the same manner as the production of the comparative organic EL element 1 except that the following two layers were used as the electron transport layer.
First electron transport layer: a layer close to the cathode.
The phosphine oxide compound A-1 was deposited to a thickness of 3 nm.
Second electron transport layer: a layer close to the light emitting layer.
BAlq was deposited to a thickness of 47 nm.

<Preparation of the organic EL element 4 of the present invention>
In the production of the comparative organic EL element 1, the organic EL element 4 of the present invention was produced in exactly the same manner as the production of the comparative organic EL element 1, except that the following two layers were used as the electron transport layer.
First electron transport layer: a layer close to the cathode.
The phosphine oxide compound A-1 was deposited to a thickness of 1 nm.
Second electron transport layer: a layer close to the light emitting layer.
BAlq was deposited to a film thickness of 49 nm.

  The chemical structure of the material used in the examples is shown below.

(Performance evaluation of organic EL elements)
1) External quantum efficiency Using a source measure unit 2400 manufactured by Toyo Technica Co., Ltd., a direct current voltage was applied to each element to emit light. The brightness was measured using a luminance meter BM-8 manufactured by Topcon Corporation. The emission spectrum and emission wavelength were measured using a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics. Based on these numerical values, the external quantum efficiency at a luminance of 1000 cd / m ² was calculated by a luminance conversion method.

2) Driving voltage Using a source measure unit 2400 manufactured by Toyo Technica Co., Ltd., a DC voltage was applied to each element to emit light. The voltage when the luminance was 1000 cd / m ² was measured as the driving voltage.
3) driving durability: a luminance half-life each element by applying a DC voltage so that the luminance 1000 cd / ^{m 2,} the luminance was measured the time until 500 cd / ^{m 2} is continuously driven. This luminance half time was used as an index of driving durability.

  The results obtained are summarized in Table 1 below.

  As is apparent from the above results, the device of the present invention has an increased external quantum efficiency, a reduced drive voltage, and a high drive durability compared to the comparative device 1. In particular, the elements 3 and 4 of the present invention showed high driving durability. That is, it is apparent that the device of the present invention exhibits excellent effects in the thin layer region of 1 nm and 3 nm of the electron transport layer containing the phosphine oxide compound.

Example 2
(Production of organic EL element)
<Production of Comparative Organic EL Element 2>
1) Formation of anode A transparent support substrate was formed by depositing ITO on a glass substrate of 25 mm × 25 mm × 0.7 mm to a thickness of 150 nm to form a film (Tokyo Sanyo Vacuum Co., Ltd.). This transparent support substrate was etched and washed.
2) Hole Injecting Layer 4,4 ′, 4 ″ -Tris (2-naphthylphenylamino) triphenylamine (hereinafter abbreviated as 2-TNATA) was deposited on the ITO glass substrate. The deposition thickness was 120 nm. did.

3) Hole transport layer N, N′-Dinaphthyl-N, N′-diphenyl- [1,1′-biphenyl] -4,4′-diamine (hereinafter referred to as α-NPD) on the hole injection / transport layer. And abbreviated to 10 nm.

4) Light-Emitting Layer On the hole transport layer, 1,3-bis (N-carbazolyl) benzene (hereinafter abbreviated as mCP) is used as a host material, and iridium (III) bis (4,6- (di-) is used as a light-emitting material. Fluoropheny) -pyridinate-N, C2 ′) picolinate (hereinafter abbreviated as FIrpic) was co-evaporated to 6 mass% with respect to mCP. The deposition thickness was 30 nm.

5) Electron transport layer On the said light emitting layer, the phosphine oxide compound A-2 was vapor-deposited by the film thickness of 40 nm.
6) Electron injection layer Further, LiF was deposited to a thickness of about 0.5 nm.
7) Formation of cathode electrode A patterned mask (a mask having a light emitting area of 2 mm × 2 mm) was placed thereon, and aluminum was evaporated to a film thickness of about 100 nm to produce a device. The produced element was sealed in a dry glove box.
Said vapor deposition was performed in the vacuum of 10 < ^-3 > Pa-10 < ^-4 > Pa, and the substrate temperature on the conditions of room temperature.

<Production of Comparative Organic EL Element 3>
In the production of the comparative organic EL element 2, the comparative organic EL element 2 was produced in exactly the same manner as the production of the comparative organic EL element 1, except that the following layers were used as the electron transport layer.
Electron transport layer: 20% by mass of cesium (Cs) was doped into the phosphine oxide compound A-2 and evaporated to a thickness of 40 nm.

<Preparation of the organic EL element 5 of the present invention>
In the production of the comparative organic EL element 2, the organic EL element 5 of the present invention was produced in exactly the same manner as the production of the comparative organic EL element 2 except that the following two layers were used as the electron transport layer.
First electron transport layer: a layer close to the cathode.
Phosphine oxide compound A-2 was deposited to a thickness of 30 nm.
Second electron transport layer: a layer close to the light emitting layer.
BAlq was deposited to a thickness of 10 nm.

<Preparation of the organic EL element 6 of the present invention>
In the production of the comparative organic EL element 2, the organic EL element 6 of the present invention was produced in exactly the same manner as the production of the comparative organic EL element 2 except that the following two layers were used as the electron transport layer.
First electron transport layer: a layer close to the cathode.
The phosphine oxide compound A-2 was deposited to a thickness of 10 nm.
Second electron transport layer: a layer close to the light emitting layer.
BAlq was deposited to a thickness of 30 nm.

<Preparation of the organic EL element 7 of the present invention>
In the production of the comparative organic EL element 2, the organic EL element 7 of the present invention was produced in exactly the same manner as the production of the comparative organic EL element 2 except that the following two layers were used as the electron transport layer.
First electron transport layer: a layer close to the cathode.
The phosphine oxide compound A-2 was deposited to a thickness of 3 nm.
Second electron transport layer: a layer close to the light emitting layer.
BAlq was deposited to a thickness of 37 nm.

<Preparation of the organic EL element 8 of the present invention>
In the production of the comparative organic EL element 2, the organic EL element 8 of the present invention was produced in the same manner as the production of the comparative organic EL element 2 except that the following two layers were used as the electron transport layer.
First electron transport layer: a layer close to the cathode.
The phosphine oxide compound A-2 was deposited to a thickness of 1 nm.
Second electron transport layer: a layer close to the light emitting layer.
BAlq was deposited to a film thickness of 39 nm.

  The chemical structure of the material used in the examples is shown below.

(Performance evaluation of organic EL elements)
In the same manner as in Example 1, the external quantum efficiency, drive voltage, and drive durability were evaluated.
However, the external quantum efficiency and the driving voltage are values at a luminance of 300 cd / m ² . The driving durability is a luminance half time at an initial luminance of 300 cd / m ² .

  The results obtained are shown in Table 2 below.

  As is apparent from the above results, the comparative element 3 has an external quantum efficiency improved and a driving voltage has decreased, but the driving durability remains extremely low. In the elements 5 to 8 of the present invention, the external quantum efficiency was improved, the driving voltage was lowered, and the driving durability was remarkably improved. In particular, the elements 7 and 8 of the present invention showed high driving durability. That is, it is apparent that the device of the present invention exhibits excellent effects in the thin layer region of 1 nm and 3 nm of the electron transport layer containing the phosphine oxide compound.

Example 3
(Production of organic EL element)
<Production of Comparative Organic EL Element 3>
1) Formation of anode A transparent support substrate was formed by depositing ITO on a glass substrate of 25 mm × 25 mm × 0.7 mm to a thickness of 150 nm to form a film (Tokyo Sanyo Vacuum Co., Ltd.). This transparent support substrate was etched and washed.
2) Hole injection layer 2-TNATA was vapor-deposited on this ITO glass substrate. The deposition thickness was 120 nm.

3) Hole transport layer α-NPD was vapor-deposited at 10 nm on the hole injection / transport layer.

4) Light-Emitting Layer On the hole transport layer, mCP as a host material and platinum complex Pt-1 as a light-emitting material were co-deposited so as to be 15% by mass with respect to mCP. The deposition thickness was 30 nm.

5) Electron transport layer On the light emitting layer, a phosphine oxide compound A-3 was deposited to a thickness of 40 nm.
6) Electron injection layer Further, LiF was deposited to a thickness of about 0.5 nm.
7) Formation of cathode electrode A patterned mask (a mask having a light emitting area of 2 mm × 2 mm) was placed thereon, and aluminum was evaporated to a film thickness of about 100 nm to produce a device. The produced element was sealed in a dry glove box.
Said vapor deposition was performed in the vacuum of 10 < ^-3 > Pa-10 < ^-4 > Pa, and the substrate temperature on the conditions of room temperature.

<Preparation of the organic EL element 9 of the present invention>
In the production of the comparative organic EL element 4, the organic EL element 9 of the present invention was produced in the same manner as the production of the comparative organic EL element 4 except that the following two layers were used as the electron transport layer.
First electron transport layer: a layer close to the cathode.
The phosphine oxide compound A-3 was deposited to a thickness of 30 nm.
Second electron transport layer: a layer close to the light emitting layer.
BAlq was deposited to a thickness of 10 nm.

<Preparation of the organic EL element 10 of the present invention>
In the production of the comparative organic EL element 4, the organic EL element 10 of the present invention was produced in exactly the same manner as the production of the comparative organic EL element 4 except that the following two layers were used as the electron transport layer.
First electron transport layer: a layer close to the cathode.
Phosphine oxide compound A-3 was deposited to a thickness of 10 nm.
Second electron transport layer: a layer close to the light emitting layer.
BAlq was deposited to a thickness of 30 nm.

<Preparation of the organic EL element 11 of the present invention>
In the production of the comparative organic EL element 4, the organic EL element 11 of the present invention was produced in exactly the same manner as the production of the comparative organic EL element 4 except that the following two layers were used as the electron transport layer.
First electron transport layer: a layer close to the cathode.
Phosphine oxide compound A-3 was deposited to a thickness of 3 nm.
Second electron transport layer: a layer close to the light emitting layer.
BAlq was deposited to a thickness of 37 nm.

<Preparation of the organic EL element 12 of the present invention>
In the production of the comparative organic EL element 4, the organic EL element 12 of the present invention was produced in exactly the same manner as the production of the comparative organic EL element 4 except that the following two layers were used as the electron transport layer.
First electron transport layer: a layer close to the cathode.
Phosphine oxide compound A-3 was deposited to a thickness of 1 nm.
Second electron transport layer: a layer close to the light emitting layer.
BAlq was deposited to a film thickness of 39 nm.

  The chemical structure of the material used in the examples is shown below.

(Performance evaluation of organic EL elements)
In the same manner as in Example 1, the external quantum efficiency, drive voltage, and drive durability were evaluated.

  The results obtained are shown in Table 3 below.

  As is clear from the above results, the devices 9 to 12 of the present invention have an improved external quantum efficiency, a reduced driving voltage, and a significantly improved driving durability relative to the comparative device 4. In particular, the elements 11 and 12 of the present invention showed high driving durability. That is, it was clear that the device of the present invention exhibited excellent effects in the thin layer region of 1 nm and 3 nm of the electron transport layer containing the phosphine oxide compound. It shows that a combination of an electron transport layer using a phosphine oxide compound and a light emitting layer using a platinum complex exhibits a particularly excellent effect.

Example 4
(Production of organic EL element)
<Production of Comparative Organic EL Element 5>
1) Formation of anode A transparent support substrate was formed by depositing ITO on a glass substrate of 25 mm × 25 mm × 0.7 mm to a thickness of 150 nm to form a film (Tokyo Sanyo Vacuum Co., Ltd.). This transparent support substrate was etched and washed.
2) Hole injection layer 2-TNATA was vapor-deposited on this ITO glass substrate. The deposition thickness was 120 nm.

3) Hole transport layer α-NPD was vapor-deposited at 10 nm on the hole injection / transport layer.

4) Light-emitting layer On the hole transport layer, mCP as a host material and platinum complex Pt-2 as a light-emitting material were co-deposited so as to be 15% by mass with respect to mCP. The deposition thickness was 30 nm.

5) Electron transport layer On the light emitting layer, a phosphine oxide compound A-4 was deposited to a thickness of 40 nm.
6) Electron injection layer Further, LiF was deposited to a thickness of about 0.5 nm.
7) Formation of cathode electrode A patterned mask (a mask having a light emitting area of 2 mm × 2 mm) was placed thereon, and aluminum was evaporated to a film thickness of about 100 nm to produce a device. The produced element was sealed in a dry glove box.
Said vapor deposition was performed in the vacuum of 10 < ^-3 > Pa-10 < ^-4 > Pa, and the substrate temperature on the conditions of room temperature.

<Preparation of the organic EL element 13 of the present invention>
In the production of the comparative organic EL element 5, the organic EL element 13 of the present invention was produced in exactly the same manner as the production of the comparative organic EL element 5 except that the following two layers were used as the electron transport layer.
First electron transport layer: a layer close to the cathode.
Phosphine oxide compound A-4 was deposited to a thickness of 30 nm.
Second electron transport layer: a layer close to the light emitting layer.
BAlq was deposited to a thickness of 10 nm.

<Preparation of the organic EL element 14 of the present invention>
In the production of the comparative organic EL element 5, the organic EL element 14 of the present invention was produced in exactly the same manner as the production of the comparative organic EL element 5 except that the following two layers were used as the electron transport layer.
First electron transport layer: a layer close to the cathode.
Phosphine oxide compound A-4 was deposited to a thickness of 10 nm.
Second electron transport layer: a layer close to the light emitting layer.
BAlq was deposited to a thickness of 30 nm.

<Preparation of the organic EL element 15 of the present invention>
In the production of the comparative organic EL element 5, the organic EL element 15 of the present invention was produced in the same manner as the production of the comparative organic EL element 5 except that the following two layers were used as the electron transport layer.
First electron transport layer: a layer close to the cathode.
Phosphine oxide compound A-4 was deposited to a thickness of 3 nm.
Second electron transport layer: a layer close to the light emitting layer.
BAlq was deposited to a thickness of 37 nm.

<Preparation of the organic EL element 16 of the present invention>
In the production of the comparative organic EL element 5, the organic EL element 16 of the present invention was produced in exactly the same manner as the production of the comparative organic EL element 5 except that the following two layers were used as the electron transport layer.
First electron transport layer: a layer close to the cathode.
Phosphine oxide compound A-4 was deposited to a thickness of 1 nm.
Second electron transport layer: a layer close to the light emitting layer.
BAlq was deposited to a film thickness of 39 nm.

  The chemical structure of the material used in the examples is shown below.

(Performance evaluation of organic EL elements)
In the same manner as in Example 1, the external quantum efficiency, drive voltage, and drive durability were evaluated.
However, the external quantum efficiency and the driving voltage are values at a luminance of 300 cd / m ² . The driving durability is a luminance half time at an initial luminance of 300 cd / m ² .

  The results obtained are shown in Table 4 below.

As is clear from the above results, the devices 13 to 16 of the present invention have an improved external quantum efficiency, a lower driving voltage, and a significantly improved driving durability relative to the comparative device 5. In particular, the device 15.16 of the present invention showed high driving durability. That is, it is apparent that the device of the present invention exhibits excellent effects in the thin layer region of 1 nm and 3 nm of the electron transport layer containing the phosphine oxide compound.

Claims (10)

  An organic electroluminescence device having at least one organic layer including a light emitting layer between a pair of electrodes, wherein an electron transport layer containing a phosphine oxide compound and the phosphine oxide compound are substantially disposed between the light emitting layer and the cathode. And an electron transport layer containing no phosphine oxide compound is close to the cathode, and an electron transport layer substantially not containing the phosphine oxide compound is close to the light emitting layer. An organic electroluminescent element characterized by comprising:   The organic electroluminescent element according to claim 1, wherein the electron transport layer containing the phosphine oxide is a layer in contact with the electron injection layer.   3. The organic electroluminescence device according to claim 1, wherein a film thickness of the electron transport layer containing the phosphine oxide is 0.01 nm or more and 10 nm or less.   The organic electroluminescent element according to claim 3, wherein the electron transport layer containing the phosphine oxide has a thickness of 0.01 nm or more and 5 nm or less. 5. The organic electroluminescent element according to claim 1, wherein the phosphine oxide compound is a compound represented by the following general formula (I):

Wherein R ¹ , R ² and R ³ are each independently an alkyl group, alkenyl group, alkynyl group, aryl group, amino group, alkoxy group, aryloxy group, heterocyclic oxy group, acyl group, alkoxycarbonyl Group, aryloxycarbonyl group, acyloxy group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group, arylthio group, heterocyclic thio group, or heterocyclic group To express.). The organic electroluminescent element according to claim 5, wherein the phosphine oxide compound represented by the general formula (I) is a compound represented by the following general formula (II):

(In the formula, Ar ¹ , Ar ² , and Ar ³ each independently represents an aryl group or a heterocyclic group). 5. The organic electroluminescent element according to claim 1, wherein the phosphine oxide compound is a compound represented by the following general formula (III):

(Wherein R ^{31 to} R ³⁴ each independently represents an aryl group or a heterocyclic group; L represents a divalent linking group).   The organic electroluminescent element according to claim 1, wherein the light emitting layer contains a phosphorescent material.   The organic electroluminescent element according to claim 8, wherein the phosphorescent material is an organometallic complex having platinum as a central metal.   The organic light-emitting device according to claim 1, wherein the light-emitting layer contains a hole-transporting organic material as a host material.