JP2012019172A - Organic electroluminescent element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an organic electroluminescent element which suppresses decrease of efficiency during high luminance driving and initial decrease of drive durability.SOLUTION: The organic electroluminescent element has a pair of electrodes consisting of a positive electrode and a negative electrode on a substrate, an emissive layer between the electrodes, at least one organic layer between the emissive layer and the positive electrode, and at least one organic layer between the emissive layer and the negative electrode. At least one organic layer between the emissive layer and the negative electrode contains at least one compound represented by (a-3), and at least one organic layer between the emissive layer and the positive electrode contains at least one compound represented by (h-1).

Description

  The present invention relates to an organic electroluminescent device.

  Organic electroluminescent elements (hereinafter also referred to as “elements” and “organic EL elements”) are actively researched and developed because they emit light with high luminance when driven at a low voltage. An organic electroluminescent element has an organic layer between a pair of electrodes, and electrons injected from the cathode and holes injected from the anode recombine in the organic layer, and the generated exciton energy is used for light emission. To do.

In recent years, the use of phosphorescent light emitting materials has led to higher efficiency of devices. In addition, a doped element using a light emitting layer in which a light emitting material is doped in a host material is widely used.
For example, Patent Documents 1 and 2 describe an organic electroluminescent device using an iridium complex as a phosphorescent material in a light-emitting layer and a compound containing a carbazole structure and a nitrogen-containing aromatic hetero 6-membered ring as a host material. ing.

In addition, for the purpose of improving the efficiency and durability of an organic electroluminescence device, a compound having electrical stability and high charge transport capability has been developed.
For example, Patent Document 3 describes an organic electroluminescent element in which a layer made of a specific compound containing a phenylcarbazole structure is provided between a light emitting layer and an anode.

JP 2009-88538 A International Publication No. 05/085387 JP 2006-151979 A

The organic electroluminescent element can be driven at a high luminance of about 10,000 cd / m ² for television and lighting applications, for example. According to the study by the present inventors, in the conventional organic electroluminescent element, It was found that the efficiency decreased when driving at high brightness compared to when driving at low brightness.
Further, when the conventional organic electroluminescence device is driven at a constant current and the decrease in luminance is observed, the decrease rate of luminance immediately after the start of light emission is large (the time until the luminance becomes 95% of the initial value is short), and then gradually. The brightness tends to decrease. This decrease in luminance at the initial stage is called “initial drop”. This initial drop is a so-called “burn-in” in which when an organic electroluminescent element is applied to a display, the luminance reduction of a pixel group exposed to continuous lighting due to a fixed image pattern or the like is recognized by the observer as a luminance step with respect to surrounding pixels. Cause. Therefore, in order to put the organic electroluminescent element into practical use in a television or the like, it is necessary to prevent this burn-in, and it is important to suppress an initial drop in driving durability.

  In view of the above circumstances, an object of the present invention is to provide an organic electroluminescent element that is less likely to have a decrease in efficiency during high-luminance driving and that has a low initial drop in driving durability.

  That is, the present invention can be achieved by the following means.

[1]
On the substrate, a pair of electrodes consisting of an anode and a cathode, a light emitting layer between the electrodes, and at least one organic layer between the light emitting layer and the anode, between the light emitting layer and the cathode An organic electroluminescent device having at least one organic layer,
Containing at least one compound represented by the following general formula (1) in at least one organic layer between the light emitting layer and the cathode;
An organic electroluminescence device comprising at least one compound represented by the following general formula (H-1) in at least one organic layer between the light emitting layer and the anode.

(In general formula (1), X ₃ , X ₄ and X ₅ are each independently a carbon atom to which a nitrogen atom or a hydrogen atom is bonded, and the ring containing X ₃ , X ₄ and X ₅ is pyridine or pyrimidine. L ′ represents a single bond or a benzene ring, and R ^{1 to} R ⁵ each independently represents a fluorine atom, a methyl group, a phenyl group, a cyano group, a pyridyl group, a pyrimidyl group, a silyl group, a carbazolyl group, or tert-butyl. N1 to n5 each independently represents 0 or 1, and p ′ and q ′ each independently represent 1 or 2.)

(In general formula (H-1), X represents a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group. .
R _H1 , R _H1 ′, R _H2 , R _H2 ′, R _H3 , and R _H3 ′ are each independently a hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted Alternatively, it represents an unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heterocyclic group, a hydroxy group, a cyano group, or a substituted or unsubstituted amino group. At least two of R _H1 , R _H2 and R _H3 may be bonded to each other to form a ring. At least two of R _H1 ′, R _H2 ′, and R _H3 ′ may be bonded to each other to form a ring.
A _H1 and A _H1 ′ are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted aromatic heterocyclic group. )
[2]
In the general formula (H-1), the organic electroluminescent device according to the above [1], wherein A _H1 and A _H1 ′ are substituted or unsubstituted aryl groups.
[3]
In the general formula (H-1), the organic electroluminescent element according to the above [1] or [2], wherein X is an unsubstituted arylene group.
[4]
In said general formula (H-1), _AH1 and _AH1 'are a substituted or unsubstituted phenyl group, a biphenyl group, or an anthryl group, Any one of said [1]-[3]. Organic electroluminescent device.
[5]
The organic electroluminescent element according to any one of [1] to [4], wherein in the general formula (H-1), X is a phenylene group, a naphthylene group, or a biphenylene group.
[6]
The organic electroluminescent element according to any one of [1] to [5], wherein the general formula (H-1) is represented by the following general formula (H-2).

(In General Formula (H-2), R _H1 , R _H1 ′, R _H2 , R _H2 ′, R _H3 , and R _H3 ′ are each independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group. Represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a cyano group, or a substituted or unsubstituted amino group.
R _H4 and R _H4 ′ are each independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a cyano group, or a substituted group Alternatively, it represents an unsubstituted amino group. )
[7]
The organic electroluminescent element according to any one of [1] to [6], wherein R _H1 , R _H1 ′, R _H2 , R _H2 ′, R _H3 , and R _H3 ′ are hydrogen atoms.
[8]
The organic electroluminescent element according to the above [6] or [7], wherein R _H4 and R _H4 ′ are a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group, or a cyano group.
[9]
The organic electroluminescent element according to any one of the above [1] to [8], wherein the light emitting layer contains a phosphorescent light emitting material.
[10]
The organic electroluminescence device according to [9], wherein the phosphorescent light-emitting material is an iridium complex.
[11]
The light-emitting device using the organic electroluminescent element of any one of said [1]-[10].
[12]
The display apparatus using the organic electroluminescent element of any one of said [1]-[10].
[13]
The illuminating device using the organic electroluminescent element of any one of said [1]-[10].

  ADVANTAGE OF THE INVENTION According to this invention, the organic electroluminescent element with a little fall of the efficiency at the time of a high-intensity drive and a little initial fall of drive durability can be provided.

It is the schematic which shows an example of a structure of the organic electroluminescent element which concerns on this invention. It is the schematic which shows an example of the light-emitting device which concerns on this invention. It is the schematic which shows an example of the illuminating device which concerns on this invention.

  The hydrogen atom in the description of the general formula (1) and the general formula (H-1) includes an isotope (deuterium atom, etc.), and the atoms constituting the substituent further include the isotope. .

In the present invention, the substituent group A and the substituent group B are defined as follows.
(Substituent group A)
An alkyl group (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, isopropyl, t-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, neopentyl, etc.), alkenyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, For example, vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, For example, propargyl, 3-pentynyl, etc.), aryl groups (preferably having 6 to 30 carbon atoms, more preferred) Has 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyl, 4-methylphenyl, 2,6-dimethylphenyl, and the like, and amino groups (preferably having 0 to 30 carbon atoms, More preferably, it has 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, and examples thereof include amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino and the like, and an alkoxy group (preferably). Has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, and examples thereof include methoxy, ethoxy, butoxy, 2-ethylhexyloxy and the like, and aryloxy groups ( Preferably it has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms. For example, phenyloxy, 1-naphthyloxy, 2-naphthyloxy, etc.), a 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). For example, pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, etc.), acyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, For example, acetyl, benzoyl, formyl, pivaloyl, etc.), 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.), aryloxycarbonyl group ( Preferably it is C7-30, More preferably, it is C7-20, Most preferably, it is C7-12, for example, phenyloxycarbonyl etc. are mentioned. ), An acyloxy group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms such as acetoxy and benzoyloxy), an acylamino group (preferably 2-30 carbon atoms, more preferably 2-20 carbon atoms, particularly preferably 2-10 carbon atoms, and examples thereof include acetylamino, benzoylamino, and the like, and an alkoxycarbonylamino group (preferably having 2-2 carbon atoms). 30, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino, etc.), aryloxycarbonylamino group (preferably 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonyl And sulfonylamino groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonylamino). ), A 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, phenyl Sulfamoyl, 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.), alkylthio group ( Preferably, it has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include methylthio, ethylthio and the like, and an arylthio group (preferably 6 to 30 carbon atoms). , More preferably 6 to 20 carbon atoms, 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 carbon atoms). 20, particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio and the like, and a sulfonyl group (preferably having a carbon number). 1 to 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as mesyl and tosyl). Rufinyl 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 methanesulfinyl and benzenesulfinyl. ), A ureido group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as ureido, methylureido, phenylureido, etc.), phosphoric acid. An amide group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide and phenylphosphoric acid amide), a hydroxy group , Mercapto group, halogen atom (eg fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, heterocyclic group ( An aromatic heterocyclic group is also included, preferably 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, Is, for example, a nitrogen atom, oxygen atom, sulfur atom, phosphorus atom, silicon atom, selenium atom, tellurium atom, specifically pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, And isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, benzoimidazolyl, benzothiazolyl, carbazolyl group, azepinyl group, silolyl 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, and examples thereof include trimethylsilyl and triphenylsilyl). Ryloxy group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, such as trimethylsilyloxy, triphenylsilyloxy, etc.), phosphoryl group (for example, A diphenylphosphoryl group, a dimethylphosphoryl group, etc.). These substituents may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above.

(Substituent group B)
An alkyl group (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, isopropyl, t-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 2 to 10 carbon atoms, for example vinyl , Allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl groups (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.), an aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 6 carbon atoms). 0, particularly preferably 6 to 12 carbon atoms, including phenyl, p-methylphenyl, naphthyl, anthranyl, etc.), cyano group, heterocyclic group (including aromatic heterocyclic group, preferably carbon The hetero atom is, for example, a nitrogen atom, oxygen atom, sulfur atom, phosphorus atom, silicon atom, selenium atom, tellurium atom, specifically pyridyl. , Pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, Benzimidazolyl, Nzothiazolyl, carbazolyl group, azepinyl group, silylyl group, etc.) These substituents may be further substituted, and examples of further substituents include groups selected from the substituent group B. . Moreover, the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group B described above. Moreover, the substituent substituted by the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group B described above.

The organic electroluminescent element of the present invention has a pair of electrodes comprising an anode and a cathode on a substrate, a light emitting layer between the electrodes, and at least one organic layer between the light emitting layer and the anode. An organic electroluminescent device having at least one organic layer between the light emitting layer and the cathode,
Containing at least one compound represented by the following general formula (1) in at least one organic layer between the light emitting layer and the cathode;
At least one organic layer between the light emitting layer and the anode contains at least one compound represented by the following general formula (H-1).

[Compound represented by the general formula (1)]
Hereinafter, the compound represented by the general formula (1) will be described.

(In general formula (1), X ₃ , X ₄ and X ₅ are each independently a carbon atom to which a nitrogen atom or a hydrogen atom is bonded, and the ring containing X ₃ , X ₄ and X ₅ is pyridine or pyrimidine. L ′ represents a single bond or a benzene ring, and R ^{1 to} R ⁵ each independently represents a fluorine atom, a methyl group, a phenyl group, a cyano group, a pyridyl group, a pyrimidyl group, a silyl group, a carbazolyl group, or tert-butyl. N1 to n5 each independently represents 0 or 1, and p ′ and q ′ each independently represent 1 or 2.)

The general formula (1) will be described.
X ₃ , X ₄ and X ₅ are each independently a carbon atom to which a nitrogen atom or a hydrogen atom is bonded, and the ring containing X ₃ , X ₄ and X ₅ is pyridine or pyrimidine. The ring containing X ₄ and X ₅ is particularly preferably a pyrimidine, X ₃ is preferably a nitrogen atom, X ₄ is preferably a carbon atom to which a hydrogen atom is bonded, and X ₅ is a nitrogen atom. Preferably there is.
L ′ represents a single bond or a benzene ring (for example, when p ′ + q ′ is 2, a phenylene group). L ′ is linked to the benzene ring in the nitrogen-containing heteroaromatic structure in the general formula (1).
R ^{1 to} R ⁵ each independently represents a fluorine atom, a methyl group, a phenyl group, a cyano group, a pyridyl group, a pyrimidyl group, a silyl group, a carbazolyl group, or a tert-butyl group. When R ¹ to R ⁵ is plural, or different in each of a plurality of ^R 1 to R ⁵ are the same.
R ^{1 to} R ⁵ may further have a substituent if possible. Examples of the substituent include a fluorine atom, a methyl group, a phenyl group, a cyano group, a pyridyl group, a pyrimidyl group, a silyl group, and a carbazolyl group. Or a tert-butyl group.
R ¹ and R ² are preferably a tert-butyl group or a silyl group, and the silyl group is more preferably a triphenylsilyl group.
R ³ is preferably a pyrimidyl group, and the pyrimidyl group preferably has a phenyl group as a substituent.
R ⁴ and R ⁵ are preferably phenyl groups.
q ′ is preferably 1.

  The compound represented by the general formula (1) is most preferably composed of only a carbon atom, a hydrogen atom and a nitrogen atom.

  The molecular weight of the compound represented by the general formula (1) is preferably 400 or more and 1000 or less, more preferably 450 or more and 800 or less, and further preferably 500 or more and 700 or less.

The lowest excited triplet (T ₁ ) energy in the film state of the compound represented by the general formula (1) is preferably 2.61 eV (62 kcal / mol) or more and 3.51 eV (80 kcal / mol) or less. More preferably, it is not less than .69 eV (63.5 kcal / mol) and not more than 3.51 eV (80 kcal / mol), and more preferably not less than 2.76 eV (65 kcal / mol) and 3.51 eV (80 kcal / mol).

  The glass transition temperature (Tg) of the compound represented by the general formula (1) is preferably 80 ° C. or higher and 400 ° C. or lower, more preferably 100 ° C. or higher and 400 ° C. or lower, and 120 ° C. or higher and 400 ° C. or lower. More preferably it is.

When the general formula (1) has a hydrogen atom, an isotope (such as deuterium atom) is also included. In this case, all hydrogen atoms in the compound may be replaced with isotopes, or a mixture in which a part is a compound containing isotopes may be used.
Although the specific example of a compound represented by General formula (1) below is illustrated, this invention is not limited to these. In the specific examples below, Ph represents a phenyl group.

The compounds exemplified as the compound represented by the above general formula (1) are the method described in International Publication No. 03/080760, the method described in International Publication No. 03/078541, pamphlet, International Publication No. 05/085387. It can be synthesized by various methods such as the method described in the pamphlet.
For example, the above exemplified compound (a-3) uses m-bromobenzaldehyde as a starting material, and paragraphs [0074]-[0075] (page 45, line 11 to page 46, 18) of WO 05/085387. Line). The above exemplary compound (a-17) is synthesized by the method described on pages 46, 9 to 46 and 12 of WO 03/080760 using 3,5-dibromobenzaldehyde as a starting material. be able to. The above exemplified compound (a-39) is synthesized by the method described on page 137, page 10 to page 139, line 9 of International Publication No. 05/022962, using N-phenylcarbazole as a starting material. Can do.

  After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.

In the present invention, the compound represented by the general formula (1) is not limited in its use, and is contained in any of the other organic layers in addition to the organic layer between the light emitting layer and the cathode. May be. As the introduction layer of the compound represented by the general formula (1), any one of a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, and a charge block layer, Or it is preferable to contain in multiple, a light emitting layer, an electron carrying layer, or an electron injection layer is more preferable, and an electron carrying layer is still more preferable.
When the compound represented by the general formula (1) is contained in the organic layer between the cathode and the light emitting layer, it is preferably contained in an amount of 70 to 100% by mass, and 85 to 100% by mass with respect to the total mass of the organic layer. % Is more preferable. When the light emitting layer contains the compound represented by the general formula (1), it is preferably included in an amount of 0.1 to 99% by weight, more preferably 1 to 95% by weight, based on the total weight of the light emitting layer. Preferably, 10 to 95% by mass is included.

[Compound represented by formula (H-1)]
The compound represented by the following general formula (H-1) will be described.

(In general formula (H-1), X represents a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group. .
R _H1 , R _H1 ′, R _H2 , R _H2 ′, R _H3 , and R _H3 ′ are each independently a hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted Alternatively, it represents an unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heterocyclic group, a hydroxy group, a cyano group, or a substituted or unsubstituted amino group. At least two of R _H1 , R _H2 and R _H3 may be bonded to each other to form a ring. At least two of R _H1 ′, R _H2 ′, and R _H3 ′ may be bonded to each other to form a ring.
A _H1 and A _H1 ′ are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted aromatic heterocyclic group. )

  In the organic electroluminescent element of the present invention, the compound represented by the general formula (H-1) is contained in at least one organic layer between the anode and the light emitting layer, but may be further contained in other layers. .

In the element of the present invention, it has been found that the efficiency reduction during high luminance driving is suppressed. This includes a compound represented by the general formula (1) in the light emitting layer and a compound represented by the general formula (H-1) in at least one organic layer between the light emitting layer and the anode. In the high luminance region, that is, the injection amount of holes and electrons into the light emitting layer in the high current region, the hole injection amount by the compound represented by the general formula (H-1) and the general formula (1) The main reason is that there is a balance between the electron injection amounts of the compounds represented.
Further, it was found that the initial drop in drive durability was suppressed in the element of the present invention. The cause of the initial drop in driving durability is considered to be mainly caused by the accumulation of electrons or holes at the interface between the light emitting layer and the adjacent layer and causing interface deterioration. If the amount of injected holes and the amount of injected electrons are balanced, it is presumed that recombination of electrons and holes is promoted, the accumulation of electrons or holes is eliminated, and initial drop suppression is achieved.

  In General Formula (H-1), X represents a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group.

When X represents a substituted or unsubstituted alkylene group, the alkylene group is preferably an alkylene group having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, such as a methylene group, an ethylene group, or a propylene group. , Butylene, octylene, decylene, hexadecylene, cyclopropylene, cyclopentylene, cyclohexylene, and the like.
When the alkylene group has a substituent, examples of the substituent include a substituent selected from the substituent group A, preferably an alkyl group (preferably an alkyl group having 1 to 8 carbon atoms, more Preferably it is a C1-C6 alkyl group, for example, a methyl group, an ethyl group, n-propyl group, isopropyl group, isobutyl group, t-butyl group, n-butyl group, cyclopropyl group etc. are mentioned, A group, an ethyl group, an isobutyl group, or a t-butyl group), an aryl group (preferably an aryl group having 6 to 18 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, A phenyl group, a biphenyl group, a fluorenyl group, a naphthyl group, and the like. A phenyl group or a biphenyl group is preferred.), A halogen atom (preferably a fluorine atom), An ano group, an alkoxy group (preferably having 1 to 20 carbon atoms, and particularly preferably a methoxy group and an ethoxy group), or an aromatic heterocyclic group (preferably an aromatic heterocyclic group having 2 to 12 carbon atoms, For example, a pyridyl group, a furyl group, a thienyl group, etc. are mentioned, A pyridyl group is more preferable.

When X represents a substituted or unsubstituted alkenylene group, the alkenylene group is preferably an alkenylene group having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, such as a vinyl group, an allyl group, 2- Examples include butenyl group and 3-pentenyl group.
When the alkenylene group has a substituent, the substituent is the same as the substituent when the alkylene group has a substituent.

When X represents a substituted or unsubstituted arylene group, the arylene group is preferably an arylene group having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms. Examples of the arylene group include a phenylene group, a naphthylene group, a biphenylene group, an anthrylene group, a terphenylene group, a fluorenylene group, a phenanthrylene group, a pyrenylene group, a triphenylenylene group, and the like. Or an anthrylene group is preferred, a phenylene group, a naphthylene group (preferably 1,5-naphthylene group) or a biphenylene group is more preferred, and a biphenylene group is still more preferred.
When the arylene group has a substituent, the substituent is the same as the substituent when the alkylene group has a substituent.

When X represents a substituted or unsubstituted divalent heterocyclic group, the divalent heterocyclic group includes 1, 2 or 3 selected from a nitrogen atom, an oxygen atom, a phosphorus atom, or a sulfur atom. It preferably contains a heteroatom. Examples of the heterocyclic group include a group in which at least one carbon atom forming a ring of a cycloalkyl group or an aryl group is replaced with the heteroatom. A divalent heterocyclic group is a group formed by removing one hydrogen atom from a monovalent heterocyclic group. Preferably it is C2-C30, More preferably, it is C2-C20, Most preferably, it is C2-C12 bivalent heterocyclic group. The divalent heterocyclic group is preferably a divalent aromatic heterocyclic group. Examples of the divalent aromatic heterocyclic group include a divalent azole group, a divalent diazole group, a divalent divalent group, and the like. Examples include a triazole group, a divalent oxazole group, a divalent thiazole group, a divalent pyridyl group, a divalent furyl group, a divalent thienyl group, and the like. A divalent azole group, a divalent diazole group, 2 A valent pyridyl group is preferred. Further, the heterocycle may have a condensed ring structure, and examples thereof include a quinoline ring.
When the divalent heterocyclic group has a substituent, the substituent is the same as the substituent when the alkylene group has a substituent.

  X preferably represents a substituted or unsubstituted arylene group, and more preferably represents an unsubstituted arylene group. Specific examples and preferred ranges when X is an arylene group are as described above.

In General Formula (H-1), R _H1 , R _H1 ′, R _H2 , R _H2 ′, R _H3 , and R _H3 ′ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, A substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heterocyclic group, a hydroxy group, a cyano group, or a substituted or unsubstituted amino group; To express.

When R _H1 , R _H1 ′, R _H2 , R _H2 ′, R _H3 , and R _H3 ′ represent a halogen atom, examples thereof include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom is preferable.

When R _H1 , R _H1 ′, R _H2 , R _H2 ′, R _H3 , and R _H3 ′ represent a substituted or unsubstituted alkyl group, the alkyl group preferably has 1 to 30 carbon atoms, and has 1 carbon atom. -20 are more preferable, and examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a pentyl group, an isoamyl group, and a hexyl group. One or more hydrogen atoms among the above alkyl groups Atoms are halogen atom, C1-C30 alkyl group, C1-C30 alkoxy group, lower alkylamino group, hydroxy group, nitro group, cyano group, amino group, amidino group, hydrazine, hydrazone, carboxylic acid group In addition, a substituent such as a sulfonic acid group or a phosphoric acid group may be substituted.

When R _H1 , R _H1 ′, R _H2 , R _H2 ′, R _H3 , and R _H3 ′ represent a substituted or unsubstituted alkoxy group, the alkoxy group preferably has 1 to 30 carbon atoms, and has 1 carbon atom. To 20 is more preferable, and examples thereof include a methoxy group, an ethoxy group, a propoxy group, an isobutyloxy group, a sec-butyloxy group, a pentyloxy group, an isoamyloxy group, and a hexyloxy group. The above hydrogen atoms include halogen atoms, alkyl groups having 1 to 30 carbon atoms, alkoxy groups having 1 to 30 carbon atoms, lower alkylamino groups, hydroxy groups, nitro groups, cyano groups, amino groups, amidino groups, hydrazines, hydrazones. Further, it may be substituted with a substituent such as a carboxylic acid group, a sulfonic acid group, or a phosphoric acid group.

When R _H1 , R _H1 ′, R _H2 , R _H2 ′, R _H3 , and R _H3 ′ represent a substituted or unsubstituted aryl group, the aryl group preferably has 6 to 30 carbon atoms, more preferably An aryl group having 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms. Examples of the aryl group include a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, a terphenyl group, a fluorenyl group, a phenanthryl group, a pyrenyl group, a triphenylenyl group, and the like. Group or terphenyl group is preferred. One or more hydrogen atoms in the aryl group are a halogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a lower alkylamino group, a hydroxy group, a nitro group, a cyano group, and an amino group. And a substituent such as an amidino group, hydrazine, hydrazone, carboxylic acid group, sulfonic acid group, and phosphoric acid group.

When R _H1 , R _H1 ′, R _H2 , R _H2 ′, R _H3 , and R _H3 ′ represent a substituted or unsubstituted aryloxy group, the aryloxy group preferably has 6 to 30 carbon atoms. Preferably it is a C6-C20, Most preferably, it is a C6-C12 aryloxy group. Examples of the aryloxy group include a phenyloxy group, a naphthyloxy group, and a biphenyloxy group, and a phenyloxy group and a naphthyloxy group are preferable. One or more hydrogen atoms in the aryloxy group are a halogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a lower alkylamino group, a hydroxy group, a nitro group, a cyano group, an amino group. Substituents such as a group, amidino group, hydrazine, hydrazone, carboxylic acid group, sulfonic acid group, and phosphoric acid group may be substituted.

When R _H1 , R _H1 ′, R _H2 , R _H2 ′, R _H3 , and R _H3 ′ represent a substituted or unsubstituted heterocyclic group, the heterocyclic group includes a nitrogen atom, an oxygen atom, a phosphorus atom, Alternatively, it preferably contains 1, 2 or 3 heteroatoms selected from sulfur atoms. Examples of the heterocyclic group include a group in which at least one carbon atom forming a ring of a cycloalkyl group or an aryl group is replaced with the heteroatom. Preferably it is C2-C30, More preferably, it is C2-C20, Most preferably, it is C2-C12 heterocyclic group. As the heterocyclic group, an aromatic heterocyclic group is preferable. Examples of the aromatic heterocyclic group include an azole group, a diazole group, a triazole group, an oxazole group, a thiazole group, a pyridyl group, a furyl group, and a thienyl group. And an azole group, a diazole group, and a pyridyl group are preferable. Further, the heterocycle may have a condensed ring structure, and examples thereof include a quinoline ring.
When the heterocyclic group has a substituent, examples of the substituent include a substituent selected from the substituent group A, specifically, a halogen atom, an alkyl group having 1 to 30 carbon atoms, carbon Examples thereof include an alkoxy group of 1 to 30, a lower alkylamino group, a hydroxy group, a nitro group, a cyano group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxylic acid group, a sulfonic acid group, and a phosphoric acid group.

When R _H1 , R _H1 ′, R _H2 , R _H2 ′, R _H3 , and R _H3 ′ represent a substituted or unsubstituted amino group, the substituent is preferably an alkyl group (preferably having a carbon number of 1 to An alkyl group having 8 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms. For example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an isobutyl group, a t-butyl group, an n-butyl group, a cyclo A propyl group, and the like, and a methyl group, an ethyl group, an isobutyl group, or a t-butyl group is preferable.), An aryl group (preferably an aryl group having 6 to 18 carbon atoms, more preferably 6 to 12 carbon atoms). For example, a phenyl group, a biphenyl group, a fluorenyl group, a naphthyl group, etc., and a phenyl group or a biphenyl group is preferred.

At least two of R _H1 , R _H2 and R _H3 may be bonded to each other to form a ring. For example, two R _H1 may combine to form a ring. The same applies to R _H1 ′, R _H2 ′, and R _H3 ′. As the ring, an aromatic ring is preferable, and a benzene ring is particularly preferable.

R _H1 , R _H1 ′, R _H2 , R _H2 ′, R _H3 , and R _H3 ′ are preferably a hydrogen atom, an alkyl group, a halogen atom, an aryl group, a cyano group, or an aromatic heterocyclic group, An atom, a methyl group, a fluorine atom, a phenyl group, a cyano group, or a pyridyl group is more preferable, and a hydrogen atom is still more preferable.

In General Formula (H-1), A _H1 and A _H1 ′ are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group.

When A _H1 and A _H1 ′ represent a substituted or unsubstituted aryl group, the aryl group is preferably an aryl group having 6 to 30 carbon atoms, particularly preferably 6 to 20 carbon atoms. Examples of the aryl group include a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, a terphenyl group, a fluorenyl group, a phenanthryl group, a pyrenyl group, a triphenylenyl group, and the like. Group is preferable, and a phenyl group, a biphenyl group, or an anthryl group is more preferable.
When the aryl group has a substituent, examples of the substituent include a substituent selected from the substituent group A, preferably an alkyl group (preferably an alkyl group having 1 to 8 carbon atoms, more Preferably it is a C1-C6 alkyl group, for example, a methyl group, an ethyl group, n-propyl group, isopropyl group, isobutyl group, t-butyl group, n-butyl group, cyclopropyl group etc. are mentioned, A group, an ethyl group, an isobutyl group, or a t-butyl group), an aryl group (preferably an aryl group having 6 to 18 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, A phenyl group, a biphenyl group, a fluorenyl group, a naphthyl group, and the like. A phenyl group or a biphenyl group is preferred.), A halogen atom (preferably a fluorine atom), Group, an alkoxy group (preferably having 1 to 20 carbon atoms, particularly preferably a methoxy group or an ethoxy group), or an aromatic heterocyclic group (preferably an aromatic heterocyclic group having 2 to 12 carbon atoms, For example, a pyridyl group, a furyl group, a thienyl group, etc. are mentioned, A pyridyl group is more preferable.) A cyano group, an alkyl group, a halogen atom, and an alkoxy group are particularly preferable.

When A _H1 and A _H1 ′ represent a substituted or unsubstituted aromatic heterocyclic group, the aromatic heterocyclic group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably It is a C2-C12 aromatic heterocyclic group. Examples of the aromatic heterocyclic group include azole group, diazole group, triazole group, oxazole group, thiazole group, pyridyl group, furyl group, thienyl group, carbazolyl group and the like.
When the heterocyclic group has a substituent, the substituent is the same as the substituent that may be included when A _H1 and A _H1 ′ are aryl groups.

A _H1 and A _H1 ′ are preferably substituted or unsubstituted aryl groups. Specific examples and preferred ranges when A _H1 and A _H1 ′ are aryl groups are as described above.

Specific examples of A _H1 and A _H1 ′ include phenyl group, ethylphenyl group, ethylbiphenyl group, o-, m- or p-fluorophenyl group, dichlorophenyl group, dicyanophenyl group, trifluoromethoxyphenyl group, o- , M- or p-tolyl group, o-, m- or p-cumenyl group, mesityl group, phenoxyphenyl group, (α, α-dimethylbenzene) phenyl group, (N, N′-dimethyl) aminophenyl group, (N, N′-diphenyl) aminophenyl group, pentarenyl group, indenyl group, naphthyl group, methylnaphthyl group, anthracenyl group, azulenyl group, heptaenyl group, acenaphthylrenyl group, phenanthrenyl group, fluorenyl group, anthraquinolyl group, methyl Anthryl, phenanthryl, triphenylene, pyreni Group, chrysenyl group, ethyl-chrycenyl group, picenyl group, ferrylenyl group, chloroferrylenyl group, pentaphenyl group, pentacenyl group, tetraphenylenyl group, hexaphenyl group, hexacenyl group, rubicenyl group, coronyl group, trinaphthylenyl A group, a heptaphenyl group, a heptacenyl group, a pyrantrenyl group, an obalenyl group, a carbazolyl group, and the like.
A _H1 and A _H1 ′ are preferably a phenyl group, a lower alkylphenyl group, a lower alkoxyphenyl group, a cyanophenyl group, a phenoxyphenyl group, a halophenyl group, a naphthyl group, a lower alkylnaphthyl group, a lower alkoxynaphthyl group, or a cyanonaphthyl group. Halonaphthyl group, fluorenyl group, carbazolyl group, lower alkylcarbazolyl group, biphenyl group, lower alkylbiphenyl group, lower alkoxybiphenyl group, thiophenyl group, indolyl group or pyridyl group. The number of carbon atoms of the lower alkyl and lower alkoxy is preferably in the range of 1-5.
More preferably, A _H1 and A _H1 ′ are monocyclic, bicyclic, tricyclic aryl groups selected from a fluorenyl group, a carbazolyl group, a phenyl group, a naphthyl group, a phenanthrenyl group, or an aromatic ring thereof having 1 carbon atom. -3, lower alkyl having 1 to 3 carbon atoms, lower alkoxy having 1 to 3 carbon atoms, cyano, phenoxy, phenyl, or an aryl group substituted with 1 to 3, preferably 1 halogen.

  The compound represented by the general formula (H-1) is preferably represented by the following general formula (H-2).

(In General Formula (H-2), R _H1 , R _H1 ′, R _H2 , R _H2 ′, R _H3 , and R _H3 ′ are each independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group. Represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a cyano group, or a substituted or unsubstituted amino group.
R _H4 and R _H4 ′ are each independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a cyano group, or a substituted group Alternatively, it represents an unsubstituted amino group. )

In general formula (H-2), preferred ranges of R _H1 , R _H1 ′, R _H2 , R _H2 ′, R _H3 , and R _H3 ′ are R _H1 and R _H1 ′ in general formula (H-1), respectively. , R _H2 , R _H2 ′, R _H3 , and R _H3 ′.

R _H4, and _{R H4} 'preferable range for _{R H1, R H1', R} H2, R H2 ', R H3, and _{R H3'} is the same as the preferred range of hydrogen atom, a fluorine atom, a substituted or An unsubstituted alkyl group (preferably an alkyl group having 1 to 30 carbon atoms, particularly preferably a methyl group or an ethyl group) or a cyano group is particularly preferred.

  Specific examples of the compound represented by the general formula (H-1) are shown below, but are not limited thereto.

The compound represented by the general formula (H-1) can be synthesized by the method described in JP-A-2006-151979.
After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.

In the light-emitting device of the present invention, the compound represented by the general formula (H-1) is contained in at least one organic layer between the light-emitting layer and the anode, but its use is not limited. It may be further contained in any layer. As the introduction layer of the compound represented by the general formula (H-1) according to the present invention, a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, a charge block It can be contained in any or a plurality of layers.
The organic layer between the light emitting layer containing the compound represented by the general formula (H-1) and the anode is more preferably a hole injection layer or a hole transport layer, and is a hole injection layer. Is more preferable.

[Organic electroluminescence device]
The device of the present invention will be described in detail.
The organic electroluminescence device of the present invention has a pair of electrodes comprising an anode and a cathode on a substrate, a light emitting layer between the electrodes, and an organic electroluminescence having at least one organic layer between the light emitting layer and the anode. An element comprising at least one compound represented by the general formula (1) in the light emitting layer and represented by the general formula (H-1) in at least one organic layer between the light emitting layer and the anode. Containing at least one compound.

In the organic electroluminescent element of the present invention, the light emitting layer is an organic layer, and further includes at least one organic layer between the light emitting layer and the anode, but may further have an organic layer.
In view of the properties of the light-emitting element, at least one of the anode and the cathode is preferably transparent or translucent.
FIG. 1 shows an example of the configuration of an organic electroluminescent device according to the present invention.
In the organic electroluminescent element 10 according to the present invention shown in FIG. 1, a light emitting layer 6 is sandwiched between an anode 3 and a cathode 9 on a support substrate 2. Specifically, a hole injection layer 4, a hole transport layer 5, a light emitting layer 6, a hole block layer 7, and an electron transport layer 8 are laminated in this order between the anode 3 and the cathode 9.

<Structure of organic layer>
There is no restriction | limiting in particular as a layer structure of the said organic layer, Although it can select suitably according to the use and objective of an organic electroluminescent element, It is preferable to form on the said transparent electrode or the said back electrode. . In this case, the organic layer is formed on the front surface or one surface of the transparent electrode or the back electrode.
There is no restriction | limiting in particular about the shape of a organic layer, a magnitude | size, thickness, etc., According to the objective, it can select suitably.

Specific examples of the layer configuration include the following, but the present invention is not limited to these configurations.
Anode / hole transport layer / light emitting layer / electron transport layer / cathode,
Anode / hole transport layer / light emitting layer / block layer / electron transport layer / cathode,
Anode / hole transport layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode,
Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode.
Anode / hole injection layer / hole transport layer / light emitting layer / block layer / electron transport layer / cathode,
Anode / hole injection layer / hole transport layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode.
The element configuration, the substrate, the cathode, and the anode of the organic electroluminescence element are described in detail in, for example, Japanese Patent Application Laid-Open No. 2008-270736, and the matters described in the publication can be applied to the present invention.

<Board>
The substrate used in the present invention is preferably a substrate that does not scatter or attenuate light emitted from the organic layer. 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.

<Anode>
The anode usually only needs to have a function as an electrode for supplying holes to the organic 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. As described above, the anode is usually provided as a transparent anode.

<Cathode>
The cathode usually has a function as an electrode for injecting electrons into the organic layer, and there is no particular limitation on the shape, structure, size, etc., and it is known depending on the use and purpose of the light-emitting element. The electrode material can be selected as appropriate.

  Regarding the substrate, anode, and cathode, the matters described in paragraphs [0070] to [0089] of JP-A-2008-270736 can be applied to the present invention.

<Organic layer>
The organic layer in the present invention will be described.

[Formation of organic layer]
In the organic electroluminescence device of the present invention, each organic layer is preferably formed by any one of a dry coating method such as a vapor deposition method and a sputtering method, a solution coating process such as a transfer method, a printing method, a spin coating method, and a bar coating method. Can be formed.

[Light emitting layer]
The light-emitting layer receives holes from the anode, the hole injection layer, or the hole transport layer when an electric field is applied, receives electrons from the cathode, the electron injection layer, or the electron transport layer, and recombines holes and electrons. It is a layer which has the function to provide and to emit light.

  The substrate, anode, cathode, organic layer, and light emitting layer are described in detail in, for example, Japanese Patent Application Laid-Open No. 2008-270736 and Japanese Patent Application Laid-Open No. 2007-266458, and the matters described in these documents can be applied to the present invention. . Furthermore, the light emitting layer may include a material that does not have charge transporting properties and does not emit light.

(Luminescent material)
As the light emitting material in the present invention, any of phosphorescent light emitting materials, fluorescent light emitting materials and the like can be used.
The light emitting layer in the present invention can contain two or more kinds of light emitting materials in order to improve the color purity and widen the light emission wavelength region. At least one of the light emitting materials is preferably a phosphorescent light emitting material.
The light emitting material in the present invention further satisfies the relationship of 1.2 eV>ΔIp> 0.2 eV and / or 1.2 eV>ΔEa> 0.2 eV with the host material. It is preferable from the viewpoint. Here, ΔIp means the difference in Ip value between the host material and the light emitting material, and ΔEa means the difference in Ea value between the host material and the light emitting material.
At least one of the light emitting materials is preferably a platinum complex material or an iridium complex material, and more preferably an iridium complex material.
The fluorescent light-emitting material and the phosphorescent light-emitting material are described in detail, for example, in paragraph numbers [0100] to [0164] of JP-A-2008-270736 and paragraph numbers [0088] to [0090] of JP-A-2007-266458, The matters described in these publications can be applied to the present invention.

  From the viewpoint of luminous efficiency and the like, a phosphorescent material is preferable. Examples of phosphorescent light-emitting materials that can be used in the present invention include US Pat. / 19373A2, JP 2001-247859, JP 2002-302671, JP 2002-117978, JP 2003-133074, JP 2002-235076, JP 2003-123982, JP 2002-170684, EP 12112757, JP 2002/27 -226495, JP 2002-234894, JP 2001-247859, JP 2001-298470, JP 2002-17367. , JP 2002-203678, JP 2002-203679, JP 2004-357799, JP 2006-256999, JP 2007-19462, JP 2007-84635, JP 2007-96259, and the like. Examples of such a light-emitting dopant include Ir complex, Pt complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu complex, Tb complex, among others. Gd complex, Dy complex, and Ce complex are mentioned. Particularly preferred is an Ir complex, a Pt complex, or a Re complex, among which an Ir complex or a Pt complex containing at least one coordination mode of a metal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond, and a metal-sulfur bond. Or Re complexes are preferred. Furthermore, from the viewpoints of luminous efficiency, driving durability, chromaticity and the like, an Ir complex and a Pt complex are particularly preferable, and an Ir complex is most preferable.

  The platinum complex is preferably a platinum complex represented by the following general formula (C-1).

(In the formula, Q ¹ , Q ² , Q ³ and Q ⁴ each independently represent a ligand coordinated to Pt. L ¹ , L ² and L ³ are each independently a single bond or a divalent linking group. Represents.)

General formula (C-1) is demonstrated. Q ¹ , Q ² , Q ³ and Q ⁴ each independently represent a ligand coordinated to Pt. At this time, the bond between Q ¹ , Q ² , Q ³ and Q ⁴ and Pt may be any of a covalent bond, an ionic bond, a coordinate bond, and the like. As an atom couple | bonded with Pt in Q < ¹ >, Q < ² >, Q < ³ > and Q < ⁴ >, a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a phosphorus atom are preferable, In Q < ¹ >, Q < ² >, Q < ³ > and Q < ⁴ > Of the atoms bonded to Pt, at least one is preferably a carbon atom, more preferably two are carbon atoms, particularly preferably two are carbon atoms and two are nitrogen atoms.
Q ¹ , Q ² , Q ³ and Q ⁴ bonded to Pt by a carbon atom may be an anionic ligand or a neutral ligand, and the anionic ligand is a vinyl ligand, Aromatic hydrocarbon ring ligand (eg benzene ligand, naphthalene ligand, anthracene ligand, phenanthrene ligand), heterocyclic ligand (eg furan ligand, thiophene ligand, pyridine) Ligand, pyrazine ligand, pyrimidine ligand, pyridazine ligand, triazine ligand, thiazole ligand, oxazole ligand, pyrrole ligand, imidazole ligand, pyrazole ligand, triazole And a condensed ring containing them (for example, quinoline ligand, benzothiazole ligand, etc.). A carbene ligand is mentioned as a neutral ligand.
Q ¹ , Q ² , Q ³ and Q ⁴ bonded to Pt with a nitrogen atom may be neutral ligands or anionic ligands, and as neutral ligands, nitrogen-containing aromatic hetero Ring ligand (pyridine ligand, pyrazine ligand, pyrimidine ligand, pyridazine ligand, triazine ligand, imidazole ligand, pyrazole ligand, triazole ligand, oxazole ligand, Examples include thiazole ligands and condensed rings containing them (for example, quinoline ligands, benzimidazole ligands), amine ligands, nitrile ligands, and imine ligands. Examples of anionic ligands include amino ligands, imino ligands, nitrogen-containing aromatic heterocyclic ligands (pyrrole ligands, imidazole ligands, triazole ligands and condensed rings containing them) (For example, indole ligand, benzimidazole ligand, etc.)).
Q ¹ , Q ² , Q ³ and Q ⁴ bonded to Pt with an oxygen atom may be neutral ligands or anionic ligands, and neutral ligands are ether ligands, Examples include ketone ligands, ester ligands, amide ligands, oxygen-containing heterocyclic ligands (furan ligands, oxazole ligands and condensed rings containing them (benzoxazole ligands, etc.)). It is done. Examples of the anionic ligand include an alkoxy ligand, an aryloxy ligand, a heteroaryloxy ligand, an acyloxy ligand, a silyloxy ligand, and the like.
Q ¹ , Q ² , Q ³ and Q ⁴ bonded to Pt with a sulfur atom may be neutral ligands or anionic ligands, and neutral ligands include thioether ligands, Examples include thioketone ligands, thioester ligands, thioamide ligands, sulfur-containing heterocyclic ligands (thiophene ligands, thiazole ligands and condensed rings containing them (such as benzothiazole ligands)). It is done. Examples of the anionic ligand include an alkyl mercapto ligand, an aryl mercapto ligand, and a heteroaryl mercapto ligand.
Q ¹ , Q ² , Q ³ and Q ⁴ bonded to Pt with a phosphorus atom may be neutral ligands or anionic ligands, and neutral ligands include phosphine ligands, Examples include phosphate ester ligands, phosphite ester ligands, and phosphorus-containing heterocyclic ligands (phosphinin ligands, etc.). Anionic ligands include phosphino ligands and phosphinyl ligands. And phosphoryl ligands.
The groups represented by Q ¹ , Q ² , Q ^3, and Q ⁴ may have a substituent, and those listed as the substituent group A can be appropriately applied as the substituent. Moreover, substituents may be connected to each other (when Q ³ and Q ⁴ are connected, a Pt complex of a cyclic tetradentate ligand is formed).

The group represented by Q ¹ , Q ² , Q ³ and Q ⁴ is preferably an aromatic hydrocarbon ring ligand bonded to Pt with a carbon atom, and an aromatic heterocyclic ligand bonded to Pt with a carbon atom. A nitrogen-containing aromatic heterocyclic ligand that binds to Pt with a nitrogen atom, an acyloxy ligand, an alkyloxy ligand, an aryloxy ligand, a heteroaryloxy ligand, a silyloxy ligand, and more Preferably, an aromatic hydrocarbon ring ligand bonded to Pt by a carbon atom, an aromatic heterocyclic ligand bonded to Pt by a carbon atom, a nitrogen-containing aromatic heterocyclic ligand bonded to Pt by a nitrogen atom , An acyloxy ligand, an aryloxy ligand, more preferably an aromatic hydrocarbon ring ligand bonded to Pt with a carbon atom, an aromatic heterocyclic ligand bonded to Pt with a carbon atom, a nitrogen atom Containing Pt Containing aromatic heterocyclic ligand, an acyloxy ligand.

L ¹ , L ² and L ³ represent a single bond or a divalent linking group. Examples of the divalent linking group represented by L ¹ , L ² and L ³ include alkylene groups (methylene, ethylene, propylene, etc.), arylene groups (phenylene, naphthalenediyl), heteroarylene groups (pyridinediyl, thiophenediyl, etc.) ), Imino group (—NR—) (such as phenylimino group), oxy group (—O—), thio group (—S—), phosphinidene group (—PR—) (such as phenylphosphinidene group), silylene group (-SiRR'-) (dimethylsilylene group, diphenylsilylene group, etc.), or a combination of these. Here, R and R ′ each independently include an alkyl group, an aryl group, and the like. These linking groups may further have a substituent.
From the viewpoint of the stability of the complex and the emission quantum yield, L ¹ , L ² and L ³ are preferably a single bond, an alkylene group, an arylene group, a heteroarylene group, an imino group, an oxy group, a thio group or a silylene group. More preferably a single bond, an alkylene group, an arylene group or an imino group, still more preferably a single bond, an alkylene group or an arylene group, still more preferably a single bond, a methylene group or a phenylene group, still more preferably. Single bond, disubstituted methylene group, more preferably single bond, dimethylmethylene group, diethylmethylene group, diisobutylmethylene group, dibenzylmethylene group, ethylmethylmethylene group, methylpropylmethylene group, isobutylmethylmethylene group, diphenyl Methylene group, methylphenylmethylene group, cyclohexanediyl group, A lopentanediyl group, a fluorenediyl group, and a fluoromethylmethylene group.
L ¹ is particularly preferably a dimethylmethylene group, a diphenylmethylene group, or a cyclohexanediyl group, and most preferably a dimethylmethylene group.
L ² and L ³ are most preferably a single bond.

  Of the platinum complexes represented by the general formula (C-1), a platinum complex represented by the following general formula (C-2) is more preferable.

(In the formula, L ²¹ represents a single bond or a divalent linking group. A ²¹ and A ²² each independently represents a carbon atom or a nitrogen atom. Z ²¹ and Z ²² each independently represent a nitrogen-containing aromatic heterocyclic ring. Z ²³ and Z ²⁴ each independently represent a benzene ring or an aromatic heterocycle.

General formula (C-2) is demonstrated. L ²¹ has the same meaning as ^{L 1} in the general formula (C-1), and the preferred ranges are also the same.

A ²¹ and A ²² each independently represent a carbon atom or a nitrogen atom. Of A ^21, A ^22, Preferably, at least one is a carbon atom, it A ^21, A ²² are both carbon atoms are preferred from the standpoint of emission quantum yield stability aspects and complexes of the complex .

Z ²¹ and Z ²² each independently represent a nitrogen-containing aromatic heterocycle. Examples of the nitrogen-containing aromatic heterocycle represented by Z ²¹ and Z ²² include a pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadiazole ring, Examples include thiadiazole rings. From the viewpoint of the stability of the complex, emission wavelength control and emission quantum yield, the ring represented by Z ²¹ and Z ²² is preferably a pyridine ring, a pyrazine ring, an imidazole ring or a pyrazole ring, more preferably a pyridine ring. , An imidazole ring and a pyrazole ring, more preferably a pyridine ring and a pyrazole ring, and particularly preferably a pyridine ring.

The nitrogen-containing aromatic heterocycle represented by Z ²¹ and Z ²² may have a substituent, the substituent group A as a substituent on a carbon atom, and the substituent on a nitrogen atom as The substituent group B can be applied. The substituent on the carbon atom is preferably an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, or a fluorine atom. The substituent is appropriately selected for controlling the emission wavelength and potential, but in the case of shortening the wavelength, an electron donating group, a fluorine atom, and an aromatic ring group are preferable. For example, an alkyl group, a dialkylamino group, an alkoxy group, A fluorine atom, an aryl group, an aromatic heterocyclic group and the like are selected. In the case of increasing the wavelength, an electron withdrawing group is preferable, and for example, a cyano group, a perfluoroalkyl group, or the like is selected. The substituent on the nitrogen atom is preferably an alkyl group, an aryl group, or an aromatic heterocyclic group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex. The substituents may be linked to form a condensed ring, and the formed ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazole. Ring, thiophene ring, furan ring and the like.

Z ²³ and Z ²⁴ each independently represent a benzene ring or an aromatic heterocycle. Examples of the nitrogen-containing aromatic heterocycle represented by Z ²³ and Z ²⁴ include a pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadi Examples include an azole ring, a thiadiazole ring, a thiophene ring, and a furan ring. From the viewpoint of stability of the complex, emission wavelength control and emission quantum yield, the ring represented by Z ²³ and Z ²⁴ is preferably a benzene ring, a pyridine ring, a pyrazine ring, an imidazole ring, a pyrazole ring, or a thiophene ring, More preferred are a benzene ring, a pyridine ring and a pyrazole ring, and still more preferred are a benzene ring and a pyridine ring.

The benzene ring and nitrogen-containing aromatic heterocycle represented by Z ²³ and Z ²⁴ may have a substituent. As the substituent on the carbon atom, the substituent group A is substituted on the nitrogen atom. The substituent group B can be applied as the group. The substituent on carbon is preferably an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, or a fluorine atom. The substituent is appropriately selected for controlling the emission wavelength and potential, but in the case of increasing the wavelength, an electron donating group and an aromatic ring group are preferable, for example, an alkyl group, a dialkylamino group, an alkoxy group, an aryl group, An aromatic heterocyclic group or the like is selected. In order to shorten the wavelength, an electron withdrawing group is preferable, and for example, a fluorine atom, a cyano group, a perfluoroalkyl group, and the like are selected. The substituent on the nitrogen atom is preferably an alkyl group, an aryl group, or an aromatic heterocyclic group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex. The substituents may be linked to form a condensed ring, and the formed ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazole. Ring, thiophene ring, furan ring and the like.

  Among the platinum complexes represented by the general formula (C-2), one of more preferable embodiments is a platinum complex represented by the following general formula (C-4).

(In General Formula (C-4), A ^{401 to} A ⁴¹⁴ each independently represent C—R or a nitrogen atom. R represents a hydrogen atom or a substituent. L ⁴¹ represents a single bond or a divalent linking group. To express.)

General formula (C-4) is demonstrated.
A ^{401 to} A ⁴¹⁴ each independently represent C—R or a nitrogen atom. R represents a hydrogen atom or a substituent.
As the substituent represented by R, those exemplified as the substituent group A can be applied.
A ^{401 to} A ⁴⁰⁶ are preferably C—R, and Rs may be connected to each other to form a ring. When A ^{401 to} A ⁴⁰⁶ are C—R, R in A ⁴⁰² and A ⁴⁰⁵ is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom, or a cyano group. More preferably a hydrogen atom, an amino group, an alkoxy group, an aryloxy group or a fluorine atom, and particularly preferably a hydrogen atom or a fluorine atom. R in A ⁴⁰¹ , A ⁴⁰³ , A ⁴⁰⁴ and A ⁴⁰⁶ is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom or a cyano group, more preferably a hydrogen atom or an amino group. Group, an alkoxy group, an aryloxy group and a fluorine atom, and particularly preferably a hydrogen atom.
L ⁴¹ has the same meaning as L ^{1 in} formula (C-1), and the preferred range is also the same.

As A ^{407 to} A ⁴¹⁴ , in each of A ^{407 to} A ⁴¹⁰ and A ^{411 to} A ⁴¹⁴ , the number of N (nitrogen atoms) is preferably 0 to 2, and more preferably 0 to 1. When shifting the emission wavelength to the short wavelength side, either A ⁴⁰⁸ or A ⁴¹² is preferably a nitrogen atom, and both A ⁴⁰⁸ and A ⁴¹² are more preferably nitrogen atoms.
In the case where A ^{407 to} A ⁴¹⁴ represent C—R, R in A ⁴⁰⁸ and A ⁴¹² is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom, A cyano group, more preferably a hydrogen atom, a perfluoroalkyl group, an alkyl group, an aryl group, a fluorine atom or a cyano group, and particularly preferably a hydrogen atom, a phenyl group, a perfluoroalkyl group or a cyano group. R of A ⁴⁰⁷ , A ⁴⁰⁹ , A ⁴¹¹ and A ⁴¹³ is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom or a cyano group, more preferably A hydrogen atom, a perfluoroalkyl group, a fluorine atom, and a cyano group are preferable, and a hydrogen atom, a phenyl group, and a fluorine atom are particularly preferable. R in A ⁴¹⁰ and A ⁴¹⁴ is preferably a hydrogen atom or a fluorine atom, and more preferably a hydrogen atom. When any of A ^{407 to} A ⁴⁰⁹ and A ^{411 to} A ⁴¹³ represents CR, Rs may be connected to each other to form a ring.

  Of the platinum complexes represented by the general formula (C-2), one of more preferable embodiments is a platinum complex represented by the following general formula (C-5).

(In General Formula (C-5), A ^{501 to} A ⁵¹² each independently represents C—R or a nitrogen atom, R represents a hydrogen atom or a substituent, and L ⁵¹ represents a single bond or a divalent linkage. Represents a group.)

General formula (C-5) is demonstrated. A ^{501 to} A ⁵⁰⁶ and L ⁵¹ have the same meanings as A ^{401 to} A ⁴⁰⁶ and L ⁴¹ in the general formula (C-4), and preferred ranges thereof are also the same.

A ⁵⁰⁷ , A ⁵⁰⁸ and A ⁵⁰⁹ and A ⁵¹⁰ , A ⁵¹¹ and A ⁵¹² each independently represent C—R or a nitrogen atom. R represents a hydrogen atom or a substituent. As the substituent represented by R, those exemplified as the substituent group A can be applied. When A ⁵⁰⁷ , A ⁵⁰⁸ and A ⁵⁰⁹ and A ⁵¹⁰ , A ⁵¹¹ and A ⁵¹² are C—R, R is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, Dialkylamino group, diarylamino group, alkyloxy group, cyano group, fluorine atom, more preferably hydrogen atom, alkyl group, perfluoroalkyl group, aryl group, dialkylamino group, cyano group, fluorine atom, more preferably A hydrogen atom, an alkyl group, a trifluoromethyl group, and a fluorine atom. If possible, the substituents may be linked to form a condensed ring structure. At least one of A ⁵⁰⁷ , A ⁵⁰⁸ and A ⁵⁰⁹ and A ⁵¹⁰ , A ⁵¹¹ and A ⁵¹² is preferably a nitrogen atom, and particularly preferably A ⁵¹⁰ or A ⁵⁰⁷ is a nitrogen atom.

  Among the platinum complexes represented by the general formula (C-1), another more preferable embodiment is a platinum complex represented by the following general formula (C-6).

(In the formula, L ⁶¹ represents a single bond or a divalent linking group. A ⁶¹ independently represents a carbon atom or a nitrogen atom. Z ⁶¹ and Z ⁶² each independently represent a nitrogen-containing aromatic heterocyclic ring. Z ⁶³ independently represents a benzene ring or an aromatic heterocyclic ring, and Y is an anionic acyclic ligand bonded to Pt.)

General formula (C-6) is demonstrated. L ⁶¹ has the same meaning as L ^{1 in} formula (C-1), and the preferred range is also the same.

A ⁶¹ represents a carbon atom or a nitrogen atom. In view of the stability of the complex and the light emission quantum yield of the complex, A ⁶¹ is preferably a carbon atom.

Z ⁶¹ and Z ⁶² are synonymous with Z ²¹ and Z ²² in the general formula (C-2), respectively, and preferred ranges thereof are also the same. Z ⁶³ has the same meaning as Z ²³ in formula (C-2), and the preferred range is also the same.

Y is an anionic acyclic ligand that binds to Pt. An acyclic ligand is one in which atoms bonded to Pt do not form a ring in the form of a ligand. As an atom couple | bonded with Pt in Y, a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom are preferable, a nitrogen atom and an oxygen atom are more preferable, and an oxygen atom is the most preferable.
A vinyl ligand is mentioned as Y couple | bonded with Pt by a carbon atom. Examples of Y bonded to Pt with a nitrogen atom include an amino ligand and an imino ligand. Examples of Y bonded to Pt with an oxygen atom include an alkoxy ligand, an aryloxy ligand, a heteroaryloxy ligand, an acyloxy ligand, a silyloxy ligand, a carboxyl ligand, a phosphate ligand, Examples thereof include sulfonic acid ligands. Examples of Y bonded to Pt with a sulfur atom include alkyl mercapto ligands, aryl mercapto ligands, heteroaryl mercapto ligands, thiocarboxylic acid ligands, and the like.
The ligand represented by Y may have a substituent, and those exemplified as the substituent group A can be appropriately applied as the substituent. Moreover, substituents may be connected to each other.

  The ligand represented by Y is preferably a ligand bonded to Pt with an oxygen atom, more preferably an acyloxy ligand, an alkyloxy ligand, an aryloxy ligand, a heteroaryloxy ligand. , A silyloxy ligand, and more preferably an acyloxy ligand.

  Of the platinum complexes represented by the general formula (C-6), one of more preferred embodiments is a platinum complex represented by the following general formula (C-7).

(In the formula, A ^{701 to} A ⁷¹⁰ each independently represents C—R or a nitrogen atom. R represents a hydrogen atom or a substituent. L ⁷¹ represents a single bond or a divalent linking group. Y represents An anionic acyclic ligand that binds to Pt.)

General formula (C-7) is demonstrated. L ⁷¹ has the same meaning as L ^{61 in} formula (C-6), and the preferred range is also the same. A ^{701 to} A ⁷¹⁰ have the same meanings as A ^{401 to} A ⁴¹⁰ in formula (C-4), and preferred ranges thereof are also the same. Y has the same meaning as Y in formula (C-6), and the preferred range is also the same.

  Specific examples of the platinum complex represented by the general formula (C-1) include [0143] to [0152], [0157] to [0158], and [0162] to [0168] of JP-A-2005-310733. The compounds described in JP-A-2006-256999, [0065] to [0083], the compounds described in JP-A-2006-93542, [0065] to [0090], JP-A-2007-73891 Nos. [0063] to [0071], No. 2007-324309, No. 0079 to [0083], No. 2006-93542 No. [0065] to [0090] The compounds described in JP-A-2007-96255, [0055] to [0071], JP-A-2006-313796 0043] include - [0046], platinum complexes exemplified other following can be mentioned.

Examples of the platinum complex compound represented by the general formula (C-1) include Journal of Organic Chemistry 53,786, (1988), G.S. R. Newkome et al. ), Page 789, method described in left line 53 to right line 7, line 790, method described in left line 18 to line 38, method 790, method described in right line 19 line to line 30 and The combination, Chemische Berichte 113, 2749 (1980), H.C. Lexy et al.), Page 2752, lines 26-35, and the like.
For example, a ligand or a dissociated product thereof and a metal compound are mixed with a solvent (for example, a halogen solvent, an alcohol solvent, an ether solvent, an ester solvent, a ketone solvent, a nitrile solvent, an amide solvent, a sulfone solvent, In the presence of a sulfoxide solvent, water, etc., or in the absence of a solvent, in the presence of a base (inorganic and organic bases such as sodium methoxide, t-butoxypotassium, triethylamine, potassium carbonate, etc.) Or in the absence of a base, at room temperature or below, or by heating (in addition to normal heating, a method of heating with a microwave is also effective).

  The content of the compound represented by the general formula (C-1) in the light emitting layer of the present invention is preferably 1 to 30% by mass, more preferably 3 to 25% by mass in the light emitting layer, More preferably, it is 20 mass%.

The iridium complex is preferably an iridium complex represented by the following general formula (T-1).
[Compound represented by formula (T-1)]
The compound represented by formula (T-1) will be described.

(In the general formula (T-1), R _T3 ′, R _T3 , R _T4 , R _T5 and R _T6 are each independently a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, A fluorovinyl group, —CO ₂ R _T , —C (O) R _T , —N (R _T ) ₂ , —NO ₂ , —OR _T , a halogen atom, an aryl group or a heteroaryl group, and further a substituent T You may have.
E represents a carbon atom or a nitrogen atom.
Q is a 5-membered or 6-membered aromatic heterocyclic ring or condensed aromatic heterocyclic ring containing one or more nitrogen atoms.
In the ring Q, the line connecting E and N is represented by a single line, but the bond type is not limited, and each may be a single bond or a double bond.
R _T3 , R _T4 , R _T5 and R _T6 may be any two adjacent to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or hetero It is aryl, and the condensed 4- to 7-membered ring may further have a substituent T.
R _T3 'and _{R T6 are, -C (R T) 2 -C} (R T) 2 -, - CR T = CR T -, - C (R T) 2 -, - O -, - NR T -, _{-O-C (R T) 2} -, - NR T -C (R T) 2 - and -N = CR _T - are connected by a connecting group selected from may form a ring, _{R T} is Each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group, or a heteroaryl group, and may further have a substituent T.
The substituents T are each independently a fluorine atom, -R ', -OR', -N (R ') ₂ , -SR', -C (O) R ', -C (O) OR', -C ( O) represents N (R ′) ₂ , —CN, —NO ₂ , —SO ₂ , —SOR ′, —SO ₂ R ′, or —SO ₃ R ′, and each R ′ independently represents a hydrogen atom, alkyl Represents a group, a perfluoroalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
(XY) represents a ligand. m represents an integer of 1 to 3, and n represents an integer of 0 to 2. m + n is 3. )

The alkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent T. The alkyl group represented by R _T3 ′, R _T3 , R _T4 , R _T5 , R _T6 is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms. Group, for example, methyl group, ethyl group, i-propyl group, cyclohexyl group, t-butyl group and the like.
The cycloalkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent T. The cycloalkyl group represented by R _T3 ′, R _T3 , R _T4 , R _T5 , and R _T6 is preferably a cycloalkyl group having 4 to 7 ring members, and more preferably a cycloalkyl group having 5 to 6 total carbon atoms. Examples of the alkyl group include a cyclopentyl group and a cyclohexyl group.
The alkenyl group represented by R _T3 ′, R _T3 , R _T4 , R _T5 and R _T6 is preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms. And vinyl, allyl, 1-propenyl, 1-isopropenyl, 1-butenyl, 2-butenyl, 3-pentenyl and the like.
The alkynyl group represented by R _T3 ′, R _T3 , R _T4 , R _T5 , R _T6 is preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms. Yes, for example, ethynyl, propargyl, 1-propynyl, 3-pentynyl and the like.

_Examples of the heteroalkyl group represented by R _T3 ′, R _T3 , R _T4 , R _T5 , and R _T6 include groups in which at least one carbon of the alkyl group is replaced with O, NR _T , or S.

Examples of the halogen atom represented by R _T3 ′, R _T3 , R _T4 , R _T5 , and R _T6 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom is preferable.

The aryl group represented by R _T3 ′, R _T3 , R _T4 , R _T5 , R _T6 is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, more preferably 6 to 6 carbon atoms. 20 aryl groups. Examples of the aryl group include a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, a terphenyl group, a fluorenyl group, a phenanthryl group, a pyrenyl group, a triphenylenyl group, and a tolyl group. Group, biphenyl group, anthryl group or terphenyl group is preferred, and phenyl group, fluorenyl group and naphthyl group are more preferred.

The heteroaryl group represented by R _T3 ′, R _T3 , R _T4 , R _T5 , R _T6 is preferably a heteroaryl group having 5 to 8 carbon atoms, more preferably a 5- or 6-membered substitution. Or an unsubstituted heteroaryl group, for example, pyridyl group, pyrazinyl group, pyridazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, cinnolinyl group, phthalazinyl group, quinoxalinyl group, pyrrolyl group, indolyl group , Furyl group, benzofuryl group, thienyl group, benzothienyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group, triazolyl group, oxazolyl group, benzoxazolyl group, thiazolyl group, benzothiazolyl group, isothiazolyl group, benzisothiazolyl group , Thiadiazolyl group, a Examples include a soxazolyl group, a benzisoxazolyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, an imidazolidinyl group, a thiazolinyl group, a sulfolanyl group, a carbazolyl group, a dibenzothryl group, a dibenzothienyl group, and a pyridoindolyl group. Preferred examples include pyridyl group, pyrimidinyl group, imidazolyl group, and thienyl group, and more preferred are pyridyl group and pyrimidinyl group.

R _T3 ′, R _T3 , R _T4 , R _T5 and R _T6 are preferably a hydrogen atom, alkyl group, cyano group, trifluoromethyl group, perfluoroalkyl group, dialkylamino group, fluorine atom, aryl group, heteroaryl group And more preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a fluorine atom or an aryl group, and still more preferably a hydrogen atom, an alkyl group or an aryl group. As the substituent T, an alkyl group, an alkoxy group, a fluorine atom, a cyano group, and a dialkylamino group are preferable, and a hydrogen atom is more preferable.

R _T3 , R _T4 , R _T5 and R _T6 may be any two adjacent to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or hetero It is aryl, and the condensed 4- to 7-membered ring may further have a substituent T. Further, the condensed 4- to 7-membered ring may be further condensed with a 4- to 7-membered ring. The definition and preferred range of the cycloalkyl, aryl and heteroaryl formed are the same as the cycloalkyl group, aryl group and heteroaryl group defined by R _T3 ′, R _T3 , R _T4 , R _T5 and R _T6 .

  Examples of the aromatic heterocyclic ring represented by ring Q include a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyrazole ring, a pyrrole ring, an imidazole ring, a triazole ring, an oxazole ring, an oxadiazole ring, a thiazole ring, a thiadiazole ring, and the like. . A pyridine ring, a pyrazine ring, and a pyrazole ring are preferable, and a pyridine ring or a pyrazole ring is more preferable.

  Examples of the condensed aromatic heterocyclic ring represented by ring Q include a quinoline ring, an isoquinoline ring, and a quinoxaline ring. Preferred are a quinoline ring and an isoquinoline ring, and more preferred is a quinoline ring.

  m is preferably 1 to 3, and more preferably 2 or 3. That is, n is preferably 0 or 1. It is preferable that the kind of ligand in a complex is comprised from 1 or 2 types, More preferably, it is 1 type. When introducing a reactive group into the complex molecule, it is also preferred that the ligand consists of two types from the viewpoint of ease of synthesis.

  The metal complex represented by the general formula (T-1) includes a ligand represented by the following general formula (T-1-A) in the general formula (T-1) or a tautomer thereof, and (X -Y) or a combination with a tautomer thereof, or all of the ligands of the metal complex are represented by the following general formula (T-1-A) Or a tautomer thereof.

(In general formula (T-1-A), R _T3 ′, R _T3 , R _T4 , R _T5 , R _T6 , E and Q are the same as R _T3 ′, R _T3 , R in general formula (T-1). ₍ It is synonymous with _T4 , R _T5 , R _T6 , E and Q. * represents the coordination position to iridium.)

  Further, as a so-called ligand used for forming a conventionally known metal complex, a known ligand (also referred to as a coordination compound) is used as a ligand represented by (XY) as necessary. You may do it.

  There are various known ligands used in conventionally known metal complexes. For example, “Photochemistry and Photophysics of Coordination Compounds” Springer-Verlag H. Published by Yersin, 1987, “Organometallic Chemistry-Fundamentals and Applications-” Liu Huabosha, Akio Yamamoto, published by 1982, etc. (for example, halogen ligands (preferably chlorine ligands), Nitrogen heteroaryl ligands (for example, bipyridyl, phenanthroline, etc.), diketone ligands (for example, acetylacetone, etc.) The ligand represented by (XY) is preferably a diketone or a picolinic acid. The derivative is most preferably acetylacetonate (acac) shown below from the viewpoint of obtaining stability of the complex and high luminous efficiency.

* Represents a coordination position to iridium.
Although the example of the ligand represented by (XY) is specifically mentioned below, this invention is not limited to these.

  In the example of the ligand represented by the above (XY), * represents a coordination position to iridium in the general formula (T-1). Rx, Ry and Rz each independently represents a hydrogen atom or a substituent. Examples of the substituent include a substituent selected from the substituent group A. Preferably, Rx and Rz are each independently an alkyl group, a perfluoroalkyl group, a fluorine atom or an aryl group, more preferably an alkyl group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, A fluorine atom and an optionally substituted phenyl group are most preferred, and a methyl group, an ethyl group, a trifluoromethyl group, a fluorine atom and a phenyl group are most preferred. Ry is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, a fluorine atom or an aryl group, more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an optionally substituted phenyl group. And most preferably a hydrogen atom or a methyl group. Since these ligands are considered not to be sites where electrons are transported in the device or where electrons are concentrated by excitation, Rx, Ry, and Rz may be any chemically stable substituent, and the effects of the present invention can be achieved. Also has no effect. Since complex synthesis is easy, (I-1), (I-4) and (I-5) are preferred, and (I-1) is most preferred. Complexes having these ligands can be synthesized in the same manner as in known synthesis examples by using corresponding ligand precursors. For example, it can synthesize | combine by the method shown below using commercially available difluoro acetylacetone similarly to the method of international publication 2009-073245 page 46.

  Moreover, the monoanionic ligand shown to general formula (I-15) can also be used as a ligand.

R _{T7 to} R _T10 in the general formula (I-15) have the same _{meanings as} R _{T3 to} R _T6 in the general formula (T-1), and preferred ranges thereof are also the same. R _T7 ′ to R _T10 ′ have the same meaning as R _T3 ′, and the preferred range is also the same as R _T3 ′. * Represents a coordination position to iridium.

  The compound represented by the general formula (T-1) is preferably a compound represented by the following general formula (T-2).

(In the general formula (T-2), R _T3 ′ to R _T6 ′ and R _{T3 to} R _T6 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, or trifluorovinyl. Represents a group, —CO ₂ R _T , —C (O) R _T , —N (R _T ) ₂ , —NO ₂ , —OR _T , a halogen atom, an aryl group or a heteroaryl group, and further has a substituent T. You may do it.
R _T3 , R _T4 , R _T5, and R _T6 may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring further has a substituent T. It may be.
R _T3 'and _{R T6 are, -C (R T) 2 -C} (R T) 2 -, - CR T = CR T -, - C (R T) 2 -, - O -, - NR T -, A ring may be formed by linking with a linking group selected from —O—C (R _T ) ₂ —, —NR _T —C (R _T ) ₂ —, and —N═CR _T —.
R _T each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group, or a heteroaryl group, and may further have a substituent T.
The substituents T are each independently a fluorine atom, -R ', -OR', -N (R ') ₂ , -SR', -C (O) R ', -C (O) OR', -C ( O) represents N (R ′) ₂ , —CN, —NO ₂ , —SO ₂ , —SOR ′, —SO ₂ R ′, or —SO ₃ R ′, and each R ′ independently represents a hydrogen atom, alkyl Represents a group, a perfluoroalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
(XY) represents a ligand. m represents an integer of 1 to 3, and n represents an integer of 0 to 2. m + n is 3. )

_{R T3} in the general formula _{(T-2) ', R} T3 ~R T6, (X-Y), the preferred range of m and n, _{R T3} in the general formula _{(T-1)', R} T3 ~R T6, This is the same as the preferred range of (XY), m and n.
R _T4 ′ is preferably a hydrogen atom, an alkyl group, an aryl group, or a fluorine atom, and more preferably a hydrogen atom.
R _T5 ′ and R _T6 ′ represent a hydrogen atom or are preferably bonded to each other to form a condensed 4- to 7-membered cyclic group, and the condensed 4- to 7-membered cyclic group includes cycloalkyl, cyclohetero More preferred is alkyl, aryl, or heteroaryl, and even more preferred is aryl.
As the substituent T in R _T4 ′ to R _T6 ′, an alkyl group, an alkoxy group, a fluorine atom, a cyano group, an alkylamino group, and a diarylamino group are preferable, and an alkyl group is more preferable.

One of preferable forms of the compound represented by the general formula (T-2) is as follows. In the general formula (T-2), R _T3 ′, R _T4 ′, R _T5 ′, R _T6 ′, R _T3 , R _T4 , R _T5 and R _T6 , any two adjacent groups are not bonded to each other to form a condensed ring.

  One of the preferable forms of the compound represented by the general formula (T-2) is a case represented by the following general formula (T-3).

_{R T3 '~R T6'} in the general formula _{(T3), R} T3 ~R _T6 is, _{R T3} in the general formula _{(T-2) '~R T6} ', have the same meaning as R T3 _{to R T6,} preferably The range is the same.
R _{T7 to} R _T10 have the same _meanings as R _{T3 to} R _T6 , and preferred ranges thereof are also the same. R _T7 ′ to R _T10 ′ have the same _meanings as R _T3 ′ to R _T6 ′, and preferred ranges thereof are also the same.

  Another preferable form of the compound represented by the general formula (T-2) is a compound represented by the following general formula (T-4).

R _T3 ′ to R _T6 ′, R _{T3 to} R _T6 , (XY), m and n in the general formula (T-4) are R _T3 ′ to R _T6 ′ and R in the general formula (T-2). _{T3 ~R T6, (X-Y} ), has the same meaning as m and n, the preferable range is also the same. Among R _T3 ′ to R _T6 ′ and R _{T3 to} R _T6 , it is particularly preferred that 0 to 2 are alkyl groups or phenyl groups and the rest are all hydrogen atoms, and R _T3 ′ to R _T6 ′ and R _{T3 to} R R More preferably, one or two of _T6 are alkyl groups and the rest are all hydrogen atoms.

  Another preferred embodiment of the compound represented by the general formula (T-2) is a compound represented by the following general formula (T-5).

R _T3 ′ to R _T7 ′, R _{T3 to} R _T6 , (XY), m and n in the general formula (T-5) are R _T3 ′ to R _T6 ′ and R in the general formula (T-2). _{T3 ~R T6, (X-Y} ), has the same meaning as m and n, preferred ones are also similar.

  Another preferable embodiment of the compound represented by the general formula (T-1) is a case represented by the following general formula (T-6).

In general formula (T-6), the definitions and preferred ranges of R _{1a to} R _1i are the same as those in R _{T3 to} R _T6 in general formula (T-1). In addition, it is particularly preferable that 0 to 2 of R _{1a to} R _1i are an alkyl group or an aryl group, and the rest are all hydrogen atoms. The definitions and preferred ranges of (X—Y), m, and n are the same as (XY), m, and n in the general formula (T-1).

  Another preferable embodiment of the compound represented by the general formula (T-1) is a case represented by the following general formula (TC-1).

(In the general formula (TC-1), R _T3 ′ to R _T5 ′ and R _{T3 to} R _T6 are each independently a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, or trifluorovinyl. Represents a group, —CO ₂ R _T , —C (O) R _T , —N (R _T ) ₂ , —NO ₂ , —OR _T , a halogen atom, an aryl group or a heteroaryl group, and further has a substituent T. You may do it.
R _T3 , R _T4 , R _T5, and R _T6 may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring further has a substituent T. It may be.
R _T3 ′, R _T4 ′, and R _T5 ′ may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring further has a substituent T. You may do it.
R _T3 'and _{R T6 are, -C (R T) 2 -C} (R T) 2 -, - CR T = CR T -, - C (R T) 2 -, - O -, - NR T -, A ring may be formed by linking with a linking group selected from —O—C (R _T ) ₂ —, —NR _T —C (R _T ) ₂ —, and —N═CR _T —.
R _T each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group, or a heteroaryl group, and may further have a substituent T.
The substituents T are each independently a fluorine atom, -R ', -OR', -N (R ') ₂ , -SR', -C (O) R ', -C (O) OR', -C ( O) represents N (R ′) ₂ , —CN, —NO ₂ , —SO ₂ , —SOR ′, —SO ₂ R ′, or —SO ₃ R ′, and each R ′ independently represents a hydrogen atom, alkyl Represents a group, a perfluoroalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
(XY) represents a ligand. m represents an integer of 1 to 3, and n represents an integer of 0 to 2. m + n is 3. )

_{R T3} in the general formula _{(TC-1) ', R} T3 ~R T6, (X-Y), the preferred range of m and n, _{R T3} in the general formula _{(T-1)', R} T3 ~R T6, This is the same as the preferred range of (XY), m and n.
R _T4 ′ is preferably a hydrogen atom, an alkyl group, or an aryl group, and more preferably a hydrogen atom or an aryl group. The aryl group is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and more preferably an aryl group having 6 to 20 carbon atoms. Examples of the aryl group include a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, a terphenyl group, a fluorenyl group, a phenanthryl group, a pyrenyl group, a triphenylenyl group, and a tolyl group. Group, biphenyl group, triphenylenyl group, anthryl group or terphenyl group is preferable, and phenyl group, biphenyl group, naphthyl group and triphenylenyl group are more preferable.

R _T5 ′ is preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom or an alkyl group. The alkyl group preferably has 1 to 10 carbon atoms, for example, methyl group, ethyl group, isopropyl group, t-butyl group, n-octyl group, n-decyl group, n-hexadecyl group, cyclopropyl group, cyclopentyl. Group, cyclohexyl group, neopentyl group, and the like, and a methyl group, an ethyl group, an isopropyl group, and a t-butyl group are preferable, and a methyl group is more preferable.

One of the preferable forms of the general formula (TC-1) is a case where any two adjacent R _T4 , R _T5 and R _T6 are bonded to each other to form a condensed ring. The ring is more preferably cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl. In particular, R _T4 and R _T5 are preferably bonded to each other to form a heteroaryl ring.

  In general formula (TC-1), m is preferably 3, and n is preferably 0.

  The general formula (TC-1) is preferably the following general formula (TC-2).

(In General Formula (TC-2), R _T3 ′ to R _T5 ′, R _T3 , R _T6 , and R _{TC1 to} R _TC4 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cyano group, Represents a perfluoroalkyl group, a trifluorovinyl group, —CO ₂ R _T , —C (O) R _T , —N (R _T ) ₂ , —NO ₂ , —OR _T , a halogen atom, an aryl group, or a heteroaryl group. Further, it may have a substituent T.
R _T3 ′, R _T4 ′, and R _T5 ′ may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring further has a substituent T. You may do it.
R _T3 'and _{R T6 are, -C (R T) 2 -C} (R T) 2 -, - CR T = CR T -, - C (R T) 2 -, - O -, - NR T -, A ring may be formed by linking with a linking group selected from —O—C (R _T ) ₂ —, —NR _T —C (R _T ) ₂ —, and —N═CR _T —.
R _T each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group, or a heteroaryl group, and may further have a substituent T.
The substituents T are each independently a fluorine atom, -R ', -OR', -N (R ') ₂ , -SR', -C (O) R ', -C (O) OR', -C ( O) represents N (R ′) ₂ , —CN, —NO ₂ , —SO ₂ , —SOR ′, —SO ₂ R ′, or —SO ₃ R ′, and each R ′ independently represents a hydrogen atom, alkyl Represents a group, a perfluoroalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
W represents a carbon atom, an oxygen atom, or a sulfur atom to which a hydrogen atom or a substituent T is bonded.
(XY) represents a ligand. m represents an integer of 1 to 3, and n represents an integer of 0 to 2. m + n is 3. )

In the general formula (TC-2), R _T3 ′ to R _T5 ′, R _T3 and R _T6 , (XY), m, and n are preferably in a range of R _T3 ′ to R _T5 in the general formula (TC-1). ', R _T3 and R _T6 , (XY), m and n are the same as the preferred ranges.
The preferable range of R _{TC1 to} R _{TC4 is the same as} the preferable range of R _T3 , preferably a hydrogen atom, an alkyl group, or an aryl group, and more preferably a hydrogen atom.
W is preferably a carbon atom having a substituent T. The substituent T is preferably an alkyl group, and the alkyl group is preferably a methyl group, an ethyl group, an isopropyl group, or a t-butyl group. More preferably, it is a methyl group.
The general formula (TC-1) is also described in Japanese Patent Application Laid-Open No. 2008-147353.

  Although the preferable specific example of a compound represented by general formula (T-1) is enumerated below, it is not limited to the following.

  The compound illustrated as a compound represented by the said general formula (T-1) is compoundable by the method of Unexamined-Japanese-Patent No. 2009-99783, the various method as described in US Patent 7279232, etc. After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.

  The compound represented by the general formula (T-1) is contained in the light emitting layer, but its use is not limited and may be further contained in any layer in the organic layer.

  As the iridium complex, in addition to the compound represented by the general formula (T-1), a compound represented by the following general formula (T-7) or a compound having carbene as a ligand can also be preferably used.

In the general formula (T-7), R _{T11 to} R _T17 have the same _{meanings as} R _{T3 to} R _T6 in the general formula (T-2), and preferred ranges thereof are also the same. Moreover, (XY), n, and m are synonymous with (XY), n, and m in general formula (T-2), and their preferable ranges are also the same.

  Although these preferable specific examples are enumerated below, it is not limited to the following.

  The light emitting material in the light emitting layer is contained in an amount of 0.1% by mass to 50% by mass with respect to the total mass of the compound generally forming the light emitting layer in the light emitting layer, but from the viewpoint of durability and external quantum efficiency. The content is preferably 1% by mass to 50% by mass, and more preferably 2% by mass to 40% by mass.

  Although the thickness of the light emitting layer is not particularly limited, it is usually preferably 2 nm to 500 nm, more preferably 3 nm to 200 nm, and more preferably 5 nm to 100 nm from the viewpoint of external quantum efficiency. More preferably.

The light emitting layer in the element of the present invention may have a mixed layer of 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 kind or two or more kinds. The host material is preferably a charge transport material. The host material may be one kind or two or more kinds, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed. Furthermore, the light emitting layer may include a material that does not have charge transporting properties and does not emit light.
The light emitting layer may be a single layer or a multilayer of two or more layers. In addition, each light emitting layer may emit light with different emission colors.

<Host material>
The host material used in the present invention is preferably a compound represented by the general formula (1).

As a host material used in the present invention, in addition to the compound represented by the general formula (1), the following compounds may be contained.
Examples of the host material include an electron transport material and a hole transport material, and a charge transport material is preferable. The host material may be one type or two or more types, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed.
For example, pyrrole, indole, carbazole (eg CBP (4,4′-di (9-carbazolyl) biphenyl), 3,3′-di (9-carbazolyl) biphenyl)), azaindole, azacarbazole, triazole, oxazole, Oxadiazole, pyrazole, imidazole, thiophene, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, arylamine, amino-substituted chalcone, styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatic tertiary amine compound, styrylamine compound , Porphyrin compounds, polysilane compounds, poly (N-vinylcarbazole), aniline copolymers, thiophene oligomers, conductive polymer oligomers such as polythiophene, organosilanes, carbon Pyridine, pyrimidine, triazine, imidazole, pyrazole, triazole, oxazole, oxadiazol, fluorenone, anthraquinodimethane, anthrone, diphenylquinone, thiopyran dioxide, carbodiimide, fluorenylidenemethane, distyrylpyrazine , Fluorine-substituted aromatic compounds, heterocyclic tetracarboxylic acid anhydrides such as naphthaleneperylene, metal complexes of phthalocyanine, 8-quinolinol derivatives, metal phthalocyanines, metal complexes having benzoxazole or benzothiazole as ligands Examples thereof include various metal complexes and derivatives thereof (which may have a substituent or a condensed ring).

In the light emitting layer of the present invention, the host material triplet lowest excitation energy (T ₁ energy) is preferably higher than the T ₁ energy of the phosphorescent light emitting material in terms of color purity, light emission efficiency, and driving durability.

  Further, the content of the host compound in the present invention is not particularly limited, but from the viewpoint of light emission efficiency and driving voltage, it is 15% by mass to 95% by mass with respect to the total compound mass forming the light emitting layer. Preferably there is.

(Charge transport layer)
The charge transport layer refers to a layer in which charge transfer occurs when a voltage is applied to the organic electroluminescent element. Specific examples include a hole injection layer, a hole transport layer, an electron block layer, a light emitting layer, a hole block layer, an electron transport layer, and an electron injection layer. A hole injection layer, a hole transport layer, an electron blocking layer, or a light emitting layer is preferable. If the charge transport layer formed by the coating method is a hole injection layer, a hole transport layer, an electron block layer, or a light emitting layer, it is possible to produce an organic electroluminescent element with low cost and high efficiency. The charge transport layer is more preferably a hole injection layer, a hole transport layer, or an electron block layer.

(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 hole injection layer and the hole transport layer are described in detail, for example, in JP-A-2008-270736 and JP-A-2007-266458, and the matters described in these publications can be applied to the present invention.
Moreover, in this invention, it is preferable to contain the compound represented by the said general formula (H-1) in a positive hole injection layer.
The following compounds can also be used as the hole injection material / hole transport material.

The hole injection layer preferably contains an electron accepting dopant. By containing an electron-accepting dopant in the hole injection layer, hole injection properties are improved, driving voltage is reduced, and efficiency is improved. The electron-accepting dopant may be any organic material or inorganic material as long as it can extract electrons from the doped material and generate radical cations. For example, tetracyanoquinodimethane ( TCNQ), tetrafluoro-tetracyanoquinodimethane _(F 4 -TCNQ), and molybdenum oxide.

  The electron-accepting dopant in the hole injection layer is preferably contained in an amount of 0.1% by mass to 50% by mass, and 0.1% by mass to 40% by mass with respect to the total compound mass forming the hole injection layer. % Content is more preferable, and 0.5% by mass to 30% by mass is more preferable.

(Electron injection layer, electron transport layer)
The electron injection layer and the electron transport layer are layers having a function of receiving electrons from the cathode or the cathode side and transporting them to the anode side. The electron injection material and the electron transport material used for these layers may be a low molecular compound or a high molecular compound.
The electron injection layer and the electron transport layer are described in detail, for example, in JP-A-2008-270736 and JP-A-2007-266458, and the matters described in these publications can be applied to the present invention.
The electron injection layer preferably contains an electron donating dopant. By including an electron donating dopant in the electron injection layer, the electron injection property is improved, the driving voltage is lowered, and the efficiency is improved. The electron donating dopant may be any organic material or inorganic material as long as it can give electrons to the doped material and generate radical anions. For example, tetrathiafulvalene (TTF) , Tetrathianaphthacene (TTT), lithium, cesium and the like.

  The electron donating dopant in the electron injection layer is preferably contained in an amount of 0.1% by mass to 50% by mass, and 0.1% by mass to 40% by mass with respect to the total mass of the compound forming the electron injection layer. It is more preferable that 0.5% by mass to 30% by mass is contained.

(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 layer adjacent to the light emitting layer on the cathode side.
As an example of the organic compound constituting the hole blocking layer, in addition to the compound represented by the general formula (1) in the present invention, aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate ( Aluminum complexes such as Aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate (abbreviated as BAlq)), triazole derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline ( Phenanthroline derivatives such as 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline (abbreviated as BCP)), triphenylene derivatives, carbazole derivatives, 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 blocking layer may have a single layer structure made of one or more of the materials described above, or may have a multilayer structure made of a plurality of layers having the same composition or different compositions.

(Electronic block 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 an organic layer adjacent to the light emitting layer on the anode side.
As an example of the organic 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 electron blocking layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.

(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.
Regarding the protective layer, the matters described in paragraph numbers [0169] to [0170] of JP-A-2008-270736 can be applied to the present invention.

(Sealing container)
The element of this invention may seal the whole element using a sealing container.
Regarding the sealing container, the matters described in paragraph No. [0171] of JP-A-2008-270736 can be applied to the present invention.
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, fluorine-based solvents such as perfluoroalkane, perfluoroamine, and perfluoroether, chlorine-based solvents, and silicone oils.

(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 methods described in each publication, Japanese Patent No. 2784615, US Pat. Nos. 5,828,429 and 6,023,308 can be applied.

The external quantum efficiency of the organic electroluminescent element of the present invention is preferably 5% or more, more preferably 7% or more. The value of the external quantum efficiency should be the maximum value of the external quantum efficiency when the device is driven at 20 ° C., or the value of the external quantum efficiency near 100 to 300 cd / m ² when the device is driven at 20 ° C. Can do.

  The internal quantum efficiency of the organic electroluminescence device of the present invention is preferably 30% or more, more preferably 50% or more, and further preferably 70% or more. The internal quantum efficiency of the device is calculated by dividing the external quantum efficiency by the light extraction efficiency. In a normal organic EL element, the light extraction efficiency is about 20%. However, the substrate shape, electrode shape, organic layer thickness, inorganic layer thickness, organic layer refractive index, inorganic layer refractive index, etc. By devising it, it is possible to increase the light extraction efficiency to 20% or more.

  The organic electroluminescent element of the present invention preferably has a maximum emission wavelength (maximum intensity wavelength of emission spectrum) of 350 nm to 700 nm, more preferably 350 nm to 600 nm, still more preferably 400 nm to 520 nm, particularly preferably. It is 400 nm or more and 465 nm or less.

(Use of light-emitting element of the present invention)
The light-emitting element of the present invention can be suitably used for light-emitting devices, pixels, display elements, displays, backlights, electrophotography, illumination light sources, recording light sources, exposure light sources, reading light sources, signs, signboards, interiors, optical communications, and the like. . In particular, it is preferably used for a device driven in a region having a high light emission luminance, such as a lighting device and a display device.

(Light emitting device)
Next, the light emitting device of the present invention will be described with reference to FIG.
The light emitting device of the present invention uses the organic electroluminescent element.
FIG. 2 is a cross-sectional view schematically showing an example of the light emitting device of the present invention.
The light-emitting device 20 of FIG. 2 is comprised by the board | substrate (support substrate) 2, the organic electroluminescent element 10, the sealing container 16, etc. FIG.

The organic electroluminescent device 10 is configured by sequentially laminating an anode (first electrode) 3, an organic layer 11, and a cathode (second electrode) 9 on a substrate 2. A protective layer 12 is laminated on the cathode 9, and a sealing container 16 is provided on the protective layer 12 with an adhesive layer 14 interposed therebetween. In addition, a part of each electrode 3 and 9, a partition, an insulating layer, etc. are abbreviate | omitted.
Here, as the adhesive layer 14, a photocurable adhesive such as an epoxy resin or a thermosetting adhesive can be used, and for example, a thermosetting adhesive sheet can also be used.

  The use of the light-emitting device of the present invention is not particularly limited, and for example, in addition to a lighting device, a display device such as a television, a personal computer, a mobile phone, and electronic paper can be used.

(Lighting device)
Next, an illumination device according to an embodiment of the present invention will be described with reference to FIG.
FIG. 3 is a cross-sectional view schematically showing an example of a lighting device according to an embodiment of the present invention.
As shown in FIG. 3, the illumination device 40 according to the embodiment of the present invention includes the organic EL element 10 and the light scattering member 30 described above. More specifically, the lighting device 40 is configured such that the substrate 2 of the organic EL element 10 and the light scattering member 30 are in contact with each other.
The light scattering member 30 is not particularly limited as long as it can scatter light. In FIG. 3, the light scattering member 30 is a member in which fine particles 32 are dispersed on a transparent substrate 31. As the transparent substrate 31, for example, a glass substrate can be preferably cited. As the fine particles 32, transparent resin fine particles can be preferably exemplified. As the glass substrate and the transparent resin fine particles, known ones can be used. In such an illuminating device 40, when light emitted from the organic electroluminescent element 10 enters the light incident surface 30A of the light scattering member 30, the incident light is scattered by the light scattering member 30, and the scattered light is scattered by the light emitting surface 30B. Is emitted as illumination light.

  EXAMPLES Hereinafter, although an Example demonstrates this invention further in detail, this invention is not limited to these.

The compounds represented by the general formula (1) used in the examples are WO03 / 080760 pamphlet, WO03 / 078541 pamphlet, WO05 / 085387 pamphlet, WO05 / 022962. No. pamphlet etc. was synthesized as a reference. For example, Compound (a-3) uses m-bromobenzaldehyde as a starting material and is disclosed in International Publication No. 05/085387 pamphlet [0074]-[0075] (page 45, line 11 to page 46, line 18). It can be synthesized by the method described.
The compound represented by the general formula (H-1) was synthesized with reference to JP-A-2006-151979.

  The organic materials used in this example were all purified by sublimation and analyzed by high performance liquid chromatography (Tosoh TSKgel ODS-100Z), and those having an absorption intensity area ratio of 254 nm of 99.9% or more were used. It was.

[Examples 1-30, Comparative Examples 1-20]
<Production of organic electroluminescence device>
A glass substrate (ITO film thickness is 120 nm) having an indium tin oxide (ITO) film having a thickness of 0.7 mm and a 2.5 cm square is placed in a cleaning container, ultrasonically cleaned in 2-propanol, and then UV-ozone for 30 minutes. Processed. On the transparent anode (ITO film), the following organic compound layers were sequentially deposited by a vacuum deposition method using a vacuum deposition apparatus (manufactured by Tokki, Small-ELVESS).
First layer (hole injection layer): materials shown in Table 1: film thickness 60 nm
Second layer: NPD: film thickness 30 nm
Third layer: CBP and Ir (ppy) ₃ (mass ratio 95: 5): film thickness 30 nm
Fourth layer (electron transport layer): materials shown in Table 1: film thickness 30 nm
On the fourth layer, BCP 1 nm, lithium fluoride 1 nm and metal aluminum 100 nm were deposited in this order to form a cathode.
This laminated body is put in a glove box substituted with nitrogen gas without being exposed to the atmosphere, and sealed with a glass sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.). Then, an organic electroluminescent element was obtained.

(Evaluation)
The produced organic electroluminescence device was evaluated for light emission efficiency at the time of low luminance and high luminance driving, and initial drop time of driving durability as follows.

<Measurement of luminous efficiency>
Using a source measure unit 2400 manufactured by KEITHLEY, a direct current voltage was applied to each element to emit light, and the luminance and emission spectrum were measured using a luminance meter SR-3 manufactured by Topcon. External quantum efficiency of luminance them based on the at 100 cd / ^{m 2,} and the brightness was calculated by the luminance conversion method, the external quantum efficiency at 15000 cd / ^{m 2.}

<Measurement of initial drop time of drive durability>
The element was driven at a constant current at an initial luminance of 15000 cd / m ^{2, and the time for the} luminance to reach 95% of the initial value (that is, the time for the luminance to drop by 5% from the initial value) was measured.
The results are shown as relative values with the initial fall time of Comparative Example 1 as 100.

[Example 31, Comparative Examples 21 to 23]
The element structure is glass substrate / ITO (120 nm) / HIL-1 (10 nm) / hole transport layer (80 nm) / BAlq + Ir-B (mass ratio 95: 5) (30 nm) / electron transport layer (30 nm) / BCP ( 1 nm) / LiF (1 nm) / Al (100 nm), and the organic electric field was changed in the same manner as in Example 1 except that the material of the hole transport layer and the material of the electron transport layer were changed as shown in Table 2 below. A light emitting element was manufactured.
Using a source measure unit 2400 manufactured by KEITHLEY, a direct current voltage was applied to each element to emit light, and the luminance and emission spectrum were measured using a luminance meter SR-3 manufactured by Topcon. Based on these, the external quantum efficiency at a luminance of 100 cd / m ² and the external quantum efficiency at a luminance of 3000 cd / m ² were calculated by a luminance conversion method.
“Initial drop time” is the time when the element is driven at a constant current at an initial luminance of 3000 cd / m ² and the luminance is 95% of the initial value (that is, the time when the luminance is reduced by 5% from the initial value). Shown as a relative value.
The results are shown in Table 2.

[Example 32, Comparative Examples 24-26]
The device configuration is glass substrate / ITO (120 nm) / hole injection layer (60 nm) / HIL-1 (10 nm) / NPD (20 nm) / Zn-1 + Ir-B (mass ratio 95: 5) (30 nm) / electron transport. Layer (30 nm) / Alq (1 nm) / LiF (1 nm) / Al (100 nm), except that the materials for the hole injection layer and the electron transport layer were changed as shown in Table 3 below. In the same manner as in Example 1, an organic electroluminescent element was produced.
Using a source measure unit 2400 manufactured by KEITHLEY, a direct current voltage was applied to each element to emit light, and the luminance and emission spectrum were measured using a luminance meter SR-3 manufactured by Topcon. Based on these, the external quantum efficiency at a luminance of 100 cd / m ² and the external quantum efficiency at a luminance of 3000 cd / m ² were calculated by a luminance conversion method.
“Initial drop time” is a time when the element is driven at a constant current at an initial luminance of 3000 cd / m ² and the luminance becomes 95% of the initial value (that is, the time when the luminance drops by 5% from the initial value). Shown as a relative value.
The results are shown in Table 3.

[Example 33, Comparative Examples 27 to 29]
The element structure is glass substrate / ITO (120 nm) / hole injection layer (60 nm) / HTL-A (30 nm) / a-3 + Ir-A (mass ratio 95: 5) (30 nm) / electron transport layer (30 nm) / It changed to Alq (1 nm) / LiF (1 nm) / Al (100 nm), and it carried out similarly to the said Example 1 except having changed the material of a positive hole injection layer and the material of an electron carrying layer as shown in following Table 4. An organic electroluminescent element was produced.
Using a source measure unit 2400 manufactured by KEITHLEY, a direct current voltage was applied to each element to emit light, and the luminance and emission spectrum were measured using a luminance meter SR-3 manufactured by Topcon. External quantum efficiency of luminance them based on the at 100 cd / ^{m 2,} and the brightness was calculated by the luminance conversion method, the external quantum efficiency at 15000 cd / ^{m 2.}
“Initial drop time” is the time when the element is driven at a constant current at an initial luminance of 15000 cd / m ² and the luminance becomes 95% of the initial value (that is, the time when the luminance drops by 5% from the initial value). Shown as a relative value.
The results are shown in Table 4.

[Example 34, Comparative Examples 30 to 32]
The device configuration is glass substrate / ITO (120 nm) / hole injection layer (60 nm) / NPD (30 nm) / mCP + Ir-C (mass ratio 85:15) (30 nm) / electron transport layer (30 nm) / Liq (1 nm) The organic electroluminescence device was prepared in the same manner as in Example 1 except that the material was changed to / Al (100 nm) and the material of the hole injection layer and the electron transport layer were changed as shown in Table 5 below.
Using a source measure unit 2400 manufactured by KEITHLEY, a direct current voltage was applied to each element to emit light, and the luminance and emission spectrum were measured using a luminance meter SR-3 manufactured by Topcon. Based on these, the external quantum efficiency at a luminance of 100 cd / m ² and the external quantum efficiency at a luminance of 2000 cd / m ² were calculated by a luminance conversion method.
“Initial drop time” is the time when the element is driven at a constant current at an initial luminance of 2000 cd / m ² and the luminance becomes 95% of the initial value (that is, the time when the luminance drops by 5% from the initial value). Shown as a relative value.
The results are shown in Table 5.

  From the results of Tables 1 to 5, it can be seen that the device of the example is suppressed from lowering the efficiency at the time of high luminance driving and has a long initial drop time compared to the device of the comparative example. Further, for example, when the material of the electron transport layer and the material of the hole injection layer in the present invention are used separately by comparison between Comparative Example 1 and Comparative Example 2 and by comparison between Comparative Example 1 and Comparative Example 11, respectively. It can be seen that the characteristic improvement width when the material for the electron transport layer and the material for the hole injection layer in the present invention are combined is higher than the characteristic improvement width.

  The compounds used in Examples and Comparative Examples are shown below.

DESCRIPTION OF SYMBOLS 2 ... Substrate 3 ... Anode 4 ... Hole injection layer 5 ... Hole transport layer 6 ... Light emitting layer 7 ... Hole block layer 8 ... Electron transport layer 9 ... -Cathode 10 ... Organic electroluminescent element 11 ... Organic layer 12 ... Protective layer 14 ... Adhesive layer 16 ... Sealing container 20 ... Light emitting device 30 ... Light scattering member 31 ..Transparent substrate 30A ... light incident surface 30B ... light exit surface 32 ... fine particles 40 ... illumination device

（一般式（１）中、Ｘ _３ 、Ｘ _４ 及びＸ _５ はそれぞれ独立に窒素原子又は水素原子が結合した炭素原子であり、Ｘ _３ 、Ｘ _４ 及びＸ _５ を含む環はピリジン又はピリミジンである。Ｌ’は、単結合又はベンゼン環を表す。Ｒ ^１ 〜Ｒ ^５ はそれぞれ独立にフッ素原子、メチル基、フェニル基、シアノ基、ピリジル基、ピリミジル基、シリル基、カルバゾリル基、又はｔｅｒｔ−ブチル基を表す。ｎ１〜ｎ５はそれぞれ独立に０又は１を表し、ｐ’は１又は２を表し、ｑ’は１を表す。）

（一般式（Ｈ−２）中、Ｒ _Ｈ１ 、Ｒ _Ｈ１ ’、Ｒ _Ｈ２ 、及びＲ _Ｈ２ ’は、それぞれ独立に、水素原子、フッ素原子、無置換のアルキル基、無置換のアリール基、無置換のピリジル基、又はシアノ基を表す。
Ｒ _Ｈ３ 、及びＲ _Ｈ３ ’は水素原子を表す。
Ｒ _Ｈ４ 、及びＲ _Ｈ４ ’は、それぞれ独立に、水素原子、フッ素原子、無置換のアルキル基、又は無置換のアリール基を表す。）
＜２＞
前記Ｒ _Ｈ１ 、Ｒ _Ｈ１ ’、Ｒ _Ｈ２ 、及びＲ _Ｈ２ ’が水素原子である、上記＜１＞に記載の有機電界発光素子。
＜３＞
前記Ｒ _Ｈ４ 、及びＲ _Ｈ４ ’が水素原子、フッ素原子、又は無置換のアルキル基である、上記＜１＞又は＜２＞に記載の有機電界発光素子。
＜４＞
前記発光層に燐光性発光材料を含有する、上記＜１＞〜＜３＞のいずれか１項に記載の有機電界発光素子。
＜５＞
前記燐光性発光材料が、イリジウム錯体である、上記＜４＞に記載の有機電界発光素子。
＜６＞
上記＜１＞〜＜５＞のいずれか１項に記載の有機電界発光素子を用いた発光装置。
＜７＞
上記＜１＞〜＜５＞のいずれか１項に記載の有機電界発光素子を用いた表示装置。
＜８＞
上記＜１＞〜＜５＞のいずれか１項に記載の有機電界発光素子を用いた照明装置。
なお、本発明は、上記＜１＞〜＜８＞に関するものであるが、参考のため、その他の事項（例えば下記〔１〕〜〔１３〕に記載の事項等）についても記載した。 That is, the present invention can be achieved by the following means.
<1>
On the substrate, a pair of electrodes consisting of an anode and a cathode, a light emitting layer between the electrodes, and at least one organic layer between the light emitting layer and the anode, between the light emitting layer and the cathode An organic electroluminescent device having at least one organic layer,
Containing at least one compound represented by the following general formula (1) in at least one organic layer between the light emitting layer and the cathode;
An organic electroluminescence device comprising at least one compound represented by the following general formula (H-2) in at least one organic layer between the light emitting layer and the anode.

(In general formula (1), X ₃ , X ₄ and X ₅ are each independently a carbon atom to which a nitrogen atom or a hydrogen atom is bonded, and the ring containing X ₃ , X ₄ and X ₅ is pyridine or pyrimidine. L ′ represents a single bond or a benzene ring, and R ^{1 to} R ⁵ each independently represents a fluorine atom, a methyl group, a phenyl group, a cyano group, a pyridyl group, a pyrimidyl group, a silyl group, a carbazolyl group, or tert-butyl. N1 to n5 each independently represents 0 or 1, p ′ represents 1 or 2, and q ′ represents 1.)

(In General Formula (H-2), R _H1 , R _H1 ′, R _H2 , and R _H2 ′ are each independently a hydrogen atom, a fluorine atom, an unsubstituted alkyl group, an unsubstituted aryl group, or an unsubstituted group. Represents a pyridyl group or a cyano group.
R _H3 and R _H3 ′ represent a hydrogen atom.
R _H4 and R _H4 ′ each independently represent a hydrogen atom, a fluorine atom, an unsubstituted alkyl group, or an unsubstituted aryl group. )
<2>
The organic electroluminescence device according to <1>, wherein R _H1 , R _H1 ′, R _H2 , and R _H2 ′ are hydrogen atoms.
<3>
The organic electroluminescence device according to <1> or <2>, wherein R _H4 and R _H4 ′ are a hydrogen atom, a fluorine atom, or an unsubstituted alkyl group.
<4>
The organic electroluminescent element according to any one of <1> to <3>, wherein the light emitting layer contains a phosphorescent light emitting material.
<5>
The organic electroluminescent element according to the above <4>, wherein the phosphorescent light emitting material is an iridium complex.
<6>
The light-emitting device using the organic electroluminescent element of any one of said <1>-<5>.
<7>
The display apparatus using the organic electroluminescent element of any one of said <1>-<5>.
<8>
The illuminating device using the organic electroluminescent element of any one of said <1>-<5>.
In addition, although this invention is related to said <1>-<8>, the other matter (For example, the matter of following [1]-[13] etc.) was also described for reference.

<Measurement of initial drop time of drive durability>
The element was driven at a constant current at an initial luminance of 15000 cd / m ^{2, and the time for the} luminance to reach 95% of the initial value (that is, the time for the luminance to drop by 5% from the initial value) was measured.
The results are shown as relative values with the initial fall time of Comparative Example 1 as 100.
In Examples 13 to 17 and Examples 22 to 24, “Example” is read as “Reference Example”.

Claims (13)

On the substrate, a pair of electrodes consisting of an anode and a cathode, a light emitting layer between the electrodes, and at least one organic layer between the light emitting layer and the anode, between the light emitting layer and the cathode An organic electroluminescent device having at least one organic layer,
Containing at least one compound represented by the following general formula (1) in at least one organic layer between the light emitting layer and the cathode;
An organic electroluminescence device comprising at least one compound represented by the following general formula (H-1) in at least one organic layer between the light emitting layer and the anode.

(In general formula (1), X ₃ , X ₄ and X ₅ are each independently a carbon atom to which a nitrogen atom or a hydrogen atom is bonded, and the ring containing X ₃ , X ₄ and X ₅ is pyridine or pyrimidine. L ′ represents a single bond or a benzene ring, and R ^{1 to} R ⁵ each independently represents a fluorine atom, a methyl group, a phenyl group, a cyano group, a pyridyl group, a pyrimidyl group, a silyl group, a carbazolyl group, or tert-butyl. N1 to n5 each independently represents 0 or 1, and p ′ and q ′ each independently represent 1 or 2.)

(In general formula (H-1), X represents a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group. .
R _H1 , R _H1 ′, R _H2 , R _H2 ′, R _H3 , and R _H3 ′ are each independently a hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted Alternatively, it represents an unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heterocyclic group, a hydroxy group, a cyano group, or a substituted or unsubstituted amino group. At least two of R _H1 , R _H2 and R _H3 may be bonded to each other to form a ring. At least two of R _H1 ′, R _H2 ′, and R _H3 ′ may be bonded to each other to form a ring.
A _H1 and A _H1 ′ are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted aromatic heterocyclic group. ) The organic electroluminescent element according to claim 1, wherein in the general formula (H-1), A _H1 and A _H1 ′ are substituted or unsubstituted aryl groups.   The organic electroluminescent element according to claim 1 or 2, wherein, in the general formula (H-1), X is an unsubstituted arylene group. The organic electroluminescence according to any one of claims 1 to 3, wherein in the general formula (H-1), _AH1 and _AH1 'are a substituted or unsubstituted phenyl group, biphenyl group, or anthryl group. element.   The organic electroluminescent element according to any one of claims 1 to 4, wherein, in the general formula (H-1), X is a phenylene group, a naphthylene group, or a biphenylene group. The organic electroluminescent element according to claim 1, wherein the general formula (H-1) is represented by the following general formula (H-2).

(In General Formula (H-2), R _H1 , R _H1 ′, R _H2 , R _H2 ′, R _H3 , and R _H3 ′ are each independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group. Represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a cyano group, or a substituted or unsubstituted amino group.
R _H4 and R _H4 ′ are each independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a cyano group, or a substituted group Alternatively, it represents an unsubstituted amino group. ) The organic electroluminescent element according to claim ₁ , wherein R _H1 , R _H1 ′, R _H2 , R _H2 ′, R _H3 , and R _H3 ′ are hydrogen atoms. The organic electroluminescence device according to claim 6 or 7, wherein R _H4 and R _H4 'are a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group, or a cyano group.   The organic electroluminescent element according to claim 1, wherein the light emitting layer contains a phosphorescent light emitting material.   The organic electroluminescent element according to claim 9, wherein the phosphorescent light-emitting material is an iridium complex.   The light-emitting device using the organic electroluminescent element of any one of Claims 1-10.   The display apparatus using the organic electroluminescent element of any one of Claims 1-10.   The illuminating device using the organic electroluminescent element of any one of Claims 1-10.

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