WO2012005364A1

WO2012005364A1 - Organic electroluminescent element

Info

Publication number: WO2012005364A1
Application number: PCT/JP2011/065719
Authority: WO
Inventors: 誠之林; 伊勢　俊大
Original assignee: 富士フイルム株式会社
Priority date: 2010-07-09
Filing date: 2011-07-08
Publication date: 2012-01-12
Also published as: KR20180018861A; KR20130097715A; JP4729643B1; KR101995080B1; JP2012019176A

Abstract

Disclosed is an organic electroluminescent element which is excellent with respect to luminous efficiency, driving voltage and durability and rarely undergoes the deterioration in efficiency during high-luminance driving, and in which the luminescent chromaticity of the element hardly depends on the thickness of a layer that is arranged between a light-emitting layer and a cathode and contains a compound having electron-transporting properties. Specifically disclosed is an organic electroluminescent element which comprises, on a substrate, a pair of electrodes composed of an anode and a cathode and a light-emitting layer arranged between the electrodes, and additionally comprises at least one organic layer arranged between the light-emitting layer and the cathode, wherein the light-emitting layer contains, for example, a compound (A-1), and the at last one organic layer arranged between the light-emitting layer and the cathode contains, for example, a compound (e-1).

Description

Organic electroluminescence device

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 can 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 Document 1 describes an organic electroluminescent element using an iridium complex as a phosphorescent material and a compound containing a carbazole structure as a host material in a light emitting layer.

In addition, for the purpose of improving the efficiency and durability of organic electroluminescent elements, compounds having electron transport properties have also been developed.
For example, Patent Document 2 describes an organic electroluminescence device in which an electron transport layer made of a specific compound containing an anthracene structure and a benzimidazole structure is provided between a light emitting layer containing a fluorescent material and a cathode.

In Patent Document 3, an iridium complex is used as a phosphorescent material in the light emitting layer, a compound containing a carbazole structure is used as a host material, and an anthracene structure and a benzimidazole structure are included between the light emitting layer and the cathode. An organic electroluminescent device provided with an electron transport layer made of a specific compound is described.

Patent Documents

4 and 5 also describe an organic electroluminescent device having a compound containing an anthracene structure and a benzimidazole structure.

Japanese Unexamined Patent Publication No. 2008-147353 Japanese Patent No. 4308663 International Publication No. 08/015949 Japanese National Table 2005-515233 International Publication No. 08/133383

For example, driving with high luminance of about 10,000 cd / m ² can be considered for lighting applications, etc., but according to the study by the present inventors, conventional organic electroluminescent elements have a higher luminance driving than a lower luminance driving. It was found that the efficiency drop (roll-off phenomenon) was remarkable.
Further, in the conventional organic electroluminescent device, since the electron transport property of the host material is low, light emission occurs near the interface between the light emitting layer and the electron transport layer, and the emission chromaticity changes greatly as the film thickness of the electron transport layer changes. It turns out that there is a problem.
In addition, there is a need for an element that has high luminous efficiency, low driving voltage, and high durability while solving the above problems.

In view of the above circumstances, an object of the present invention is a compound that is excellent in terms of light emission efficiency, drive voltage, and durability, has little decrease in efficiency during high luminance drive, and has an electron transport property between the light emitting layer and the cathode It is an object to provide an organic electroluminescence device in which the luminescence chromaticity of the device is less dependent on the film thickness of the layer containing the.

According to the study by the present inventors, the above-mentioned problem is caused by containing a specific compound containing a carbazole structure in the light emitting layer, and including a specific compound containing an anthracene structure and a benzimidazole structure in the cathode side layer from the light emitting layer. I found out that it could be solved.
That is, the present invention can be achieved by the following means.

[1]
An organic electroluminescent device having a pair of electrodes consisting of 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 cathode,
The light emitting layer contains at least one compound represented by the following general formula (1),
An organic electroluminescence device comprising at least one compound represented by the following general formula (E-1) in at least one organic layer between the light emitting layer and the cathode.

(In the general formula (1), R ₁ represents an alkyl group, an aryl group, or a silyl group, and may further have a substituent Z, provided that R ₁ represents a carbazolyl group or a perfluoroalkyl group. If no .R ₁ there are a plurality, the plurality of R ₁ each may be the same or different. the plurality of R ₁ may form an aryl ring which may have a substituent Z bonded to each other May be.
R ₂ to R ₅ each independently represents an alkyl group, an aryl group, a silyl group, a cyano group, or a fluorine atom, and may further have a substituent Z. When a plurality of R ₂ to R ₅ are present, the plurality of R ₂ to R ₅ may be the same as or different from each other.
The substituent Z represents an alkyl group, an alkenyl group, an aryl group, an aromatic heterocyclic group, an alkoxy group, a phenoxy group, a fluorine atom, a silyl group, an amino group, a cyano group, or a group formed by combining these, and a plurality of substituents Z may combine with each other to form an aryl ring.
n1 represents an integer of 0 to 5.
n2 to n5 each independently represents an integer of 0 to 4. )

(In General Formula (E-1), R _E1 and R _E2 each independently represent a hydrogen atom, an aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group. However, R _E1 and R _E2 are not simultaneously hydrogen atoms.
Ar represents a substituted or unsubstituted arylene group or a substituted or unsubstituted divalent aromatic heterocyclic group.
R _E3 represents a hydrogen atom, an aliphatic hydrocarbon, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group.
R _E4 represents a hydrogen atom, an aliphatic hydrocarbon, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group. )
[2]
The organic electroluminescent element according to the above [1], wherein the compound represented by the general formula (1) is represented by the following general formula (2).

(In General Formula (2), R ₆ and R ₇ each independently represents an alkyl group which may have a substituent Z, an aryl group which may have an alkyl group, a cyano group or a fluorine atom. When a plurality of R ₆ and R ₇ are present, the plurality of R ₆ and the plurality of R ₇ may be the same as or different from each other, and the plurality of R ₆ and the plurality of R ₇ are bonded to each other. An aryl ring which may have a substituent Z may be formed.
n6 and n7 each independently represents an integer of 0 to 5.
R ₈ to R ₁₁ are each independently a hydrogen atom, an alkyl group optionally having substituent Z, an aryl group optionally having alkyl group, or a silyl group optionally having substituent Z Represents a cyano group or a fluorine atom.
The substituent Z represents an alkyl group, an alkenyl group, an aryl group, an aromatic heterocyclic group, an alkoxy group, a phenoxy group, a fluorine atom, a silyl group, an amino group, a cyano group, or a group formed by combining these, and a plurality of substituents Z may combine with each other to form an aryl ring. )
[3]
The organic electroluminescent element according to the above [1] or [2], wherein R _E4 in the general formula (E-1) is an unsubstituted aryl group.
[4]
The organic electroluminescence device according to any one of [1] to [3] above, wherein, in the general formula (E-1), Ar is an unsubstituted arylene group.
[5]
The organic electroluminescent element according to any one of the above [1] to [4], wherein R _E4 in the general formula (E-1) is a phenyl group.
[6]
The organic electroluminescence device according to any one of [1] to [5] above, wherein, in the general formula (E-1), Ar is a phenylene group.
[7]
The organic electroluminescence according to any one of the above [1] to [6], wherein the general formula (E-1) is represented by the following general formula (E-2) or the following general formula (E-3): element.

(In General Formulas (E-2) and (E-3), R _E1 and R _E2 are each independently a hydrogen atom, an aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted group. However, R _E1 and R _E2 are not simultaneously hydrogen atoms.
R _E3 represents a hydrogen atom, an aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group. )
[8]
8. The organic electroluminescence device according to any one of [1] to [7], wherein R _E3 is a hydrogen atom.
[9]
The organic electroluminescence device according to any one of [1] to [8], wherein R _E1 and R _E2 are each independently a naphthyl group.
[10]
The organic electroluminescence device according to any one of [1] to [9], wherein the light emitting layer contains a phosphorescent light emitting material.
[11]
The organic electroluminescence device according to [10], wherein the phosphorescent light-emitting material is a compound represented by the following general formula (T-1).

(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, Represents 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; 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.
Each substituent T 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. )
[12]
Any one of [1] to [11] above, wherein at least one of the light emitting layer and the other organic layer existing between the anode and the cathode is formed by a solution coating process. Organic electroluminescent element.
[13]
A light emitting device using the organic electroluminescent element according to any one of [1] to [12].
[14]
A display device using the organic electroluminescent element according to any one of [1] to [12].
[15]
An illumination device using the organic electroluminescent element according to any one of [1] to [12].
[16]
An organic electroluminescent device having a pair of electrodes consisting of 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 cathode,
The light emitting layer contains at least one compound represented by the following general formula (1),
The light emitting layer contains a phosphorescent light emitting material represented by the following general formula (T-1),
An organic electroluminescence device comprising at least one compound represented by the following general formula (E-1) in at least one organic layer between the light emitting layer and the cathode.

(In General Formula (1), R ₁ represents an alkyl group or an aryl group, and may further have a substituent Z. However, R ₁ does not represent a carbazolyl group or a perfluoroalkyl group. _{If 1} there are a plurality, the plurality of R ₁ each may be the same or different. the plurality of R ₁ may be formed an aryl ring which may have a substituent Z bonded to each other Good.
R ₂ to R ₅ each independently represents an alkyl group, an aryl group, a silyl group, a cyano group, or a fluorine atom, and may further have a substituent Z. When a plurality of R ₂ to R ₅ are present, the plurality of R ₂ to R ₅ may be the same as or different from each other.
The substituent Z represents an alkyl group, an aryl group, or a fluorine atom.
n1 represents an integer of 1 to 4.
n2 to n5 each independently represents an integer of 0 to 4. )

(In General Formula (E-1), R _E1 and R _E2 each independently represent an unsubstituted aryl group or an unsubstituted pyridyl group.
Ar represents an unsubstituted arylene group or an unsubstituted divalent pyridyl group.
R _E3 represents a hydrogen atom or an unsubstituted aryl group.
R _E4 represents an unsubstituted aryl group or an unsubstituted pyridyl group. )

(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, Represents 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; 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.
Each substituent T 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. )
[17]
The organic electroluminescence device according to [16], wherein the compound represented by the general formula (1) is represented by the following general formula (2).

(In the general formula (2), are each _{R 6} and _{R 7} independently represent an alkyl group, if .R ₆ and _{R 7} representing an aryl group, or a fluorine atom is present in plural, a plurality of _{R 6} and a plurality of R ₇ may be the same or different, and the plurality of R ₆ and the plurality of R ₇ may be bonded to each other to form an aryl ring which may have a substituent Z.
n6 and n7 each independently represents an integer of 0 to 2.
R ₈ to R ₁₁ are each independently a hydrogen atom, an alkyl group optionally having substituent Z, an aryl group optionally having alkyl group, or a silyl group optionally having substituent Z Represents a cyano group or a fluorine atom.
The substituent Z represents an alkyl group, an aryl group, or a fluorine atom. )
[18]
The organic electroluminescence device according to [16] or [17] above, wherein in formula (E-1), R _E4 is an unsubstituted aryl group.
[19]
The organic electroluminescence device according to any one of the above [16] to [18], wherein, in the general formula (E-1), Ar is an unsubstituted arylene group.
[20]
The organic electroluminescence device according to any one of [16] to [19] above, wherein, in the general formula (E-1), R _E4 is a phenyl group.
[21]
The organic electroluminescence device according to any one of [16] to [20] above, wherein in the general formula (E-1), Ar is a phenylene group.
[22]
The organic electroluminescence according to any one of [16] to [21], wherein the general formula (E-1) is represented by the following general formula (E-2) or the following general formula (E-3): element.

(In the general formulas (E-2) and (E-3), R _E1 and R _E2 each independently represents an unsubstituted aryl group or an unsubstituted pyridyl group.
R _E3 represents a hydrogen atom or an unsubstituted aryl group. )
[23]
The organic electroluminescence device according to any one of [16] to [22], wherein R _E3 is a hydrogen atom.
[24]
The organic electroluminescence device according to any one of [16] to [23], wherein R _E1 and R _E2 are each independently a naphthyl group.
[25]
Any one of [16] to [24] above, wherein at least one of the light emitting layer and the other organic layer existing between the anode and the cathode is formed by a solution coating process. Organic electroluminescent element.
[26]
A light emitting device using the organic electroluminescent element according to any one of [16] to [25].
[27]
[16] A display device using the organic electroluminescent element as described in any one of [16] to [25].
[28]
An illumination device using the organic electroluminescent element according to any one of [16] to [25].

According to the present invention, a film of a layer including a compound having an electron transporting property between a light emitting layer and a cathode, which is excellent in terms of luminous efficiency, driving voltage, and durability, has a small decrease in efficiency when driven at high luminance. It is possible to provide an organic electroluminescence device in which the emission chromaticity of the device is less dependent on the thickness.

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.

In the explanation of general formula (1) and general formula (E-1), the hydrogen atom also includes isotopes (deuterium atoms, etc.), and the atoms constituting the substituents also include the isotopes. .

In the present invention, the substituent group A, the substituent group B, and the substituent Z 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, 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 alkoxy groups (preferably Has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms, and examples thereof include methoxy, ethoxy, butoxy, 2-ethylhexyloxy, and the like. Preferably, it has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and 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, particularly preferably 1 to 12 carbon atoms). For example, pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, etc.), an acyl group (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). , Ethoxycarbonyl, etc.), aryloxycarbonyl group ( The number of carbon atoms is preferably 7 to 30, more preferably 7 to 20, and particularly preferably 7 to 12, and examples thereof include phenyloxycarbonyl. ), 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, benzoyloxy, etc.), 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 alkoxycarbonylamino groups (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.), an aryloxycarbonylamino group (preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, for example phenyloxycarbonyl And sulfonylamino groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonylamino). ), A sulfamoyl group (preferably 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.), carbamoyl groups (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, such as methylthio, ethylthio, etc.), 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 of 1 to 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include 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, 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 phenyl phosphoric 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 having 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). A aryloxy 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.), alkenyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as 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 such as propargyl , 3-pentynyl, etc.), aryl groups (preferably having 6 to 30 carbon atoms, more preferably 6 to 0, particularly preferably 6 to 12 carbon atoms, including, for example, 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, an oxygen atom, a sulfur atom, a phosphorus atom, a silicon atom, a selenium atom, or a 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.

(Substituent Z)
Represents an alkyl group, an alkenyl group, an aryl group, an aromatic heterocyclic group, an alkoxy group, a phenoxy group, a fluorine atom, a silyl group, an amino group, a cyano group or a combination thereof, and a plurality of substituents Z are bonded to each other Thus, an aryl ring may be formed.
As the substituent Z, an alkyl group, an aryl group, a fluorine atom, or a cyano group is preferable, and an alkyl group, an aryl group, or a fluorine atom is more preferable.

The alkyl group represented by the substituent Z is preferably an alkyl group having 1 to 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 Group, isobutyl group, t-butyl group, n-butyl group, cyclopropyl group, and the like. A methyl group, an ethyl group, an isobutyl group, or a t-butyl group is preferable, and a methyl group is more preferable.
The alkenyl group represented by the substituent Z is preferably an alkenyl group having 2 to 8 carbon atoms, more preferably an alkenyl group having 2 to 6 carbon atoms, such as a vinyl group, an n-propenyl group, an isopropenyl group, Examples thereof include an isobutenyl group, an n-butenyl group, and the like, and a vinyl group, an n-propenyl group, an isobutenyl group, or an n-butenyl group is preferable, and a vinyl group is more preferable.
The aryl group represented by the substituent Z is preferably an aryl group having 6 to 18 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. For example, a phenyl group, a biphenyl group, a naphthyl group, a tolyl group, a xylyl group and the like can be mentioned. Of these, a phenyl group and a biphenyl group are preferable, and a phenyl group is more preferable.

The aromatic heterocyclic group represented by the substituent Z is preferably an aromatic heterocyclic group having 4 to 12 carbon atoms, and examples thereof include a pyridyl group, a furyl group, and a thienyl group, and a pyridyl group or a furyl group is preferable. A pyridyl group is more preferable.
The alkoxy group represented by the substituent Z is preferably an alkoxy group having 1 to 8 carbon atoms, more preferably an alkoxy group having 1 to 4 carbon atoms, such as a methoxy group, an ethoxy group, an n-propoxy group, A propoxy group, an isobutoxy group, a t-butoxy group, an n-butoxy group, a cyclopropyloxy group, and the like can be given. A methoxy group, an ethoxy group, an isobutoxy group, or a t-butoxy group is preferable, and a methoxy group is more preferable.
Examples of the silyl group and amino group represented by the substituent Z include those similar to the silyl group and amino group in the substituent group A described above.
Examples of the aryl ring formed by bonding a plurality of substituents Z to each other include a benzene ring and a naphthalene ring, and a benzene ring is preferable.

The organic electroluminescent device of the present invention comprises a substrate having a pair of electrodes consisting of an anode and a cathode, a light emitting layer between the electrodes, and an organic layer having at least one organic layer between the light emitting layer and the cathode. An electroluminescent device comprising:
Containing at least one compound represented by the general formula (1) in the light emitting layer;
At least one compound represented by formula (E-1) is contained in at least one organic layer between the light emitting layer and the cathode.

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

The alkyl group represented by R ₁ may have a substituent. In the case of having a substituent, examples of the substituent include the aforementioned substituent Z, and the substituent Z is preferably a fluorine atom. However, the alkyl group represented by R ₁ does not become a perfluoroalkyl group. The alkyl group represented by R ₁ is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and still more preferably an alkyl group having 1 to 4 carbon atoms. . For example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, n-pentyl group, isopentyl group, 2-methylpentyl group, neopentyl group, n-hexyl group, 4-methylpentyl group, 3-methylpentyl group, 2-methylpentyl group, 3,3-dimethylbutyl group, 2,2-dimethylbutyl group, 1,1-dimethylbutyl group, 1,2 -Dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group and the like, and among these, methyl group, isopropyl group, t-butyl group, or neopentyl group are preferable, and methyl group or t A -butyl group is more preferred, and a t-butyl group is still more preferred.

The aryl group represented by R ₁ may be condensed or may have a substituent. In the case of having a substituent, examples of the substituent include the above-described substituent Z. The substituent Z is preferably an alkyl group, an aryl group, a fluorine atom or a cyano group which may be substituted with a fluorine atom. Groups are more preferred. The aryl group represented by R ₁ is preferably an aryl group having 6 to 30 carbon atoms, and more preferably an aryl group having 6 to 18 carbon atoms. The aryl group having 6 to 18 carbon atoms is preferably an alkyl group optionally having a fluorine atom having 1 to 6 carbon atoms, a fluorine atom or a cyano group, and optionally having 6 to 18 carbon atoms. And more preferably an aryl group having 6 to 18 carbon atoms which may have an alkyl group having 1 to 4 carbon atoms. For example, phenyl group, dimethylphenyl group, biphenyl group, terphenyl group, naphthyl group, methylnaphthyl group, t-butylnaphthyl group, anthranyl group, phenanthryl group, chrysenyl group, cyanophenyl group, trifluoromethylphenyl group, fluoride A phenyl group, etc., among which a phenyl group, a dimethylphenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a methylnaphthyl group, or a t-butylnaphthyl group is preferable, and a phenyl group, a biphenyl group, a naphthyl group, or A terphenyl group is more preferred.

The silyl group represented by R ₁ may have a substituent. In the case of having a substituent, examples of the substituent include the above-described substituent Z, and the substituent Z is preferably an alkyl group or a phenyl group, and more preferably a phenyl group. The silyl group represented by R ₁ is preferably a silyl group having 0 to 18 carbon atoms, and more preferably a silyl group having 3 to 18 carbon atoms. The silyl group having 3 to 18 carbon atoms is preferably a silyl group having 3 to 18 carbon atoms substituted with an alkyl group having 1 to 6 carbon atoms or a phenyl group, and all three hydrogen atoms of the silyl group are carbon atoms. It is more preferably substituted with any one of an alkyl group of 1 to 6 and a phenyl group, and further preferably substituted with a phenyl group. For example, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, diethylisopropylsilyl group, dimethylphenylsilyl group, diphenylmethylsilyl group, triphenylsilyl group, and the like. Group or triphenylsilyl group is preferable, and triphenylsilyl group is more preferable.

If R ₁ there are a plurality, the plurality of R ₁ may each be the same or different. Moreover, several R < ₁ > may couple | bond together and may form the aryl ring which may have the above-mentioned substituent Z. As the substituent Z, an alkyl group or an aryl group is preferable, and an alkyl group is more preferable.
Aryl ring plurality of R ₁ is formed by bonding with, including the carbon atom to which R ₁ of said plurality of substitution, preferably an aryl ring having 6 to 30 carbon atoms, more preferably having 6 to 14 carbon atoms An aryl ring. The ring to be formed is preferably any one of a benzene ring, a naphthalene ring and a phenanthrene ring, more preferably a benzene ring or a phenanthrene ring, and further preferably a benzene ring. In addition, a plurality of rings formed by a plurality of R ₁ may exist, for example, a plurality of R ₁ are bonded to each other to form two benzene rings, together with a benzene ring substituted by the plurality of R ₁ A phenanthrene ring may be formed.

R ₁ is preferably an alkyl group, an aryl group optionally having an alkyl group, and a silyl group substituted with an alkyl group or a phenyl group, from the viewpoint of charge transport ability and charge stability. More preferably an aryl group having 6 to 18 carbon atoms which may have an alkyl group having 1 to 6 carbon atoms, and still more preferably an alkyl group having an alkyl group having 1 to 4 carbon atoms. 6 to 18 aryl groups.
Among these, R ₁ is preferably a methyl group, a t-butyl group, a neopentyl group, an unsubstituted phenyl group, a cyano group, a phenyl group substituted by a fluorine atom or a trifluoromethyl group, a biphenyl group, a terphenyl group. A benzene ring or a phenanthrene ring formed by bonding an unsubstituted naphthyl group, a naphthyl group substituted by a methyl group or a t-butyl group, a triphenylsilyl group, a plurality of alkyl groups or an aryl group, respectively, An unsubstituted phenyl group, a biphenyl group, a naphthyl group, or a terphenyl group is more preferable, and an unsubstituted phenyl group, an unsubstituted biphenyl group, or an unsubstituted naphthyl group is more preferable.

N1 is preferably an integer of 0 to 4, more preferably an integer of 0 to 3, and still more preferably an integer of 0 to 2.

Specific examples and preferred examples of the aryl group and silyl group represented by R ₂ to R ₅ are the same as the specific examples and preferred examples of the aryl group and silyl group represented by R ₁ .
Examples of the alkyl group represented by R ₂ to R ₅ include perfluoroalkyl groups such as a trifluoromethyl group in addition to the examples of the alkyl group represented by R ₁ . Of these, a methyl group, a trifluoromethyl group, an isopropyl group, a t-butyl group, or a neopentyl group is preferable, a methyl group or a t-butyl group is more preferable, and a t-butyl group is still more preferable.

R ₂ to R ₅ are each independently preferably any of a silyl group substituted with an alkyl group, an aryl group, an alkyl group or a phenyl group, a cyano group, and a fluorine atom, from the viewpoint of charge transportability and charge stability. More preferably, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 18 carbon atoms, an alkyl group having 1 to 6 carbon atoms, or a silyl group having 3 to 18 carbon atoms substituted with a phenyl group, cyano Or a fluorine atom, and more preferably an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkyl group having 1 to 6 carbon atoms, or a carbon number 3 substituted with a phenyl group One of -18 silyl group, cyano group, and fluorine atom.
Among them, R ₂ to R ₅ are preferably each independently methyl group, isopropyl group, t-butyl group, neopentyl group, trifluoromethyl group, phenyl group, dimethylphenyl group, trimethylsilyl group, triphenylsilyl group, fluorine Any of an atom and a cyano group, more preferably a t-butyl group, a phenyl group, a trimethylsilyl group, a triphenylsilyl group, and a cyano group, still more preferably a t-butyl group, a phenyl group, It is either a triphenylsilyl group or a cyano group.

N2 to n5 are each independently preferably an integer of 0 to 2, and more preferably 0 or 1. When a substituent is introduced into the carbazole skeleton, the 3-position and the 6-position of the carbazole skeleton are reaction active positions. From the viewpoint of ease of synthesis and improvement in chemical stability, the substituent may be introduced at this position. preferable.

More preferably, the compound represented by the general formula (1) is represented by the following general formula (2).

(In General Formula (2), R ₆ and R ₇ each independently represents an alkyl group which may have a substituent Z, an aryl group which may have an alkyl group, a cyano group or a fluorine atom. When a plurality of R ₆ and R ₇ are present, the plurality of R ₆ and the plurality of R ₇ may be the same as or different from each other, and the plurality of R ₆ and the plurality of R ₇ are bonded to each other. An aryl ring which may have a substituent Z may be formed.
n6 and n7 each independently represents an integer of 0 to 5.
R ₈ to R ₁₁ are each independently a hydrogen atom, an alkyl group optionally having substituent Z, an aryl group optionally having alkyl group, or a silyl group optionally having substituent Z Represents a cyano group or a fluorine atom.
The substituent Z represents an alkyl group, an alkenyl group, an aryl group, an aromatic heterocyclic group, an alkoxy group, a phenoxy group, a fluorine atom, a silyl group, an amino group, a cyano group, or a group formed by combining these, and a plurality of substituents Z may combine with each other to form an aryl ring. )

The alkyl group represented by R ₆ and R ₇ may have a substituent. In the case of having a substituent, examples of the substituent include the aforementioned substituent Z, and the substituent Z is preferably a fluorine atom.
The alkyl group represented by R ₆ and R ₇ is preferably an alkyl group having 1 to 6 carbon atoms, and more preferably an alkyl group having 1 to 4 carbon atoms. Specific examples and preferred examples of the alkyl group represented by R ₆ and R ₇ are the same as the specific examples and preferred examples of the alkyl group represented by R ₂ to R ₅ in the general formula (1).

The alkyl group in the aryl group which may have an alkyl group represented by R ₆ and R ₇ is preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms. It is. Specific examples and preferred examples of the alkyl group are the same as the specific examples and preferred examples of the alkyl group represented by R ₂ to R ₅ in the general formula (1).
The aryl group in the aryl group which may have an alkyl group represented by R ₆ and R ₇ is preferably an aryl group having 6 to 18 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms. It is. For example, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthranyl group, a phenanthryl group, a chrysenyl group, etc., among which a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group are preferable, a phenyl group, A biphenyl group or a terphenyl group is more preferable.
The aryl group that may have an alkyl group represented by R ₆ and R ₇ is preferably an unsubstituted aryl group.
Examples of the aryl group represented by R ₆ and R ₇ which may have an alkyl group include a phenyl group, a dimethylphenyl group, a t-butylphenyl group, a biphenyl group, a terphenyl group, a naphthyl group, and a methyl group. A naphthyl group, a t-butyl naphthyl group, an anthranyl group, a phenanthryl group, a chrysenyl group, and the like can be given. A phenyl group, a t-butylphenyl group, or a biphenyl group is preferable, and a phenyl group is more preferable.

When a plurality of R ₆ and R ₇ are present, the plurality of R ₆ and the plurality of R ₇ may be the same as or different from each other. A plurality of R ₆ and a plurality of R ₇ may be bonded to each other to form an aryl ring which may have the aforementioned substituent Z. As the substituent Z, an alkyl group or an aryl group is preferable, and an alkyl group is more preferable.
The aryl ring formed by bonding a plurality of R ₆ and a plurality of R ₇ to each other includes a carbon atom substituted by each of the plurality of R ₆ and the plurality of R ₇ , and preferably has 6 to 30 carbon atoms. More preferred is an aryl ring having 6 to 14 carbon atoms, and still more preferred is an aryl ring having 6 to 14 carbon atoms which may have an alkyl group having 1 to 4 carbon atoms. The ring to be formed is preferably any of a benzene ring, a naphthalene ring and a phenanthrene ring, which may have an alkyl group having 1 to 4 carbon atoms, and has an alkyl group having 1 to 4 carbon atoms. An benzene ring which may be substituted is more preferable, and examples thereof include a benzene ring and a benzene ring substituted with a t-butyl group. A plurality of rings formed by a plurality of R ₆ or a plurality of R ₇ may exist, for example, a plurality of R ₆ or a plurality of R ₇ are bonded to each other to form two benzene rings, A phenanthrene ring may be formed together with a plurality of R ₆ or the benzene ring substituted by the plurality of R ₇ .

R ₆ and R ₇ are preferably an alkyl group having 1 to 6 carbon atoms and an alkyl group having 1 to 6 carbon atoms, preferably 6 to 18 carbon atoms, from the viewpoint of charge transport ability and charge stability. Any of aryl groups, cyano groups and fluorine atoms, more preferably an alkyl group having 1 to 4 carbon atoms and an aryl group having 6 to 12 carbon atoms which may have an alkyl group having 1 to 4 carbon atoms. , Either a cyano group or a fluorine atom. From the viewpoint of charge transportability and charge stability, it is also preferable that R ₆ and R ₇ each independently represent an alkyl group or an aryl group that may have an alkyl group.
Among them, R ₆ and R ₇ are preferably each independently, preferably a methyl group, a trifluoromethyl group, a t-butyl group, an unsubstituted phenyl group, a phenyl group substituted by a t-butyl group, a biphenyl group, a cyano group. An unsubstituted benzene ring formed by bonding a group, a fluorine atom and a plurality of alkyl groups to each other, or a benzene ring substituted with a t-butyl group, more preferably a methyl group or trifluoromethyl An unsubstituted benzene ring formed by bonding a group, an unsubstituted phenyl group, a cyano group, a fluorine atom, and a plurality of alkyl groups to each other, or a benzene ring substituted with a t-butyl group, Most preferably, it is an unsubstituted phenyl group.

N6 and n7 are each independently preferably an integer of 0 to 4, more preferably an integer of 0 to 2, and even more preferably 0 or 1.

The alkyl group represented by R ₈ to R ₁₁ may have a substituent. In the case of having a substituent, examples of the substituent include the aforementioned substituent Z, and the substituent Z is preferably a fluorine atom.
The alkyl group represented by R ₈ to R ₁₁ is preferably an alkyl group having 1 to 6 carbon atoms, and more preferably an alkyl group having 1 to 4 carbon atoms. Specific examples and preferred examples of the alkyl group represented by R ₈ to R ₁₁ are the same as the specific examples and preferred examples of the alkyl group represented by R ₂ to R ₅ in the general formula (1).

The aryl group optionally having an alkyl group represented by R ₈ to R ₁₁ is preferably an aryl group having 6 to 18 carbon atoms which may have an alkyl group having 1 to 6 carbon atoms. And more preferably an aryl group having 6 to 12 carbon atoms which may have an alkyl group having 1 to 4 carbon atoms.
Specific examples and preferred examples of the aryl group optionally having an alkyl group represented by R ₈ to R ₁₁ may have an alkyl group represented by the aforementioned R ₆ and R _7. This is the same as the specific examples and preferred examples of the aryl group.

The silyl group represented by R ₈ to R ₁₁ may have a substituent. In the case of having a substituent, examples of the substituent include the above-described substituent Z, and the substituent Z is preferably an alkyl group or a phenyl group, and more preferably a phenyl group. The silyl group represented by R ₈ to R ₁₁ is preferably a silyl group having 3 to 18 carbon atoms. Specific examples and preferred examples of the silyl group having 3 to 18 carbon atoms represented by R ₈ to R ₁₁ are The same as the specific examples and preferred examples of the silyl group having 3 to 18 carbon atoms in the silyl group represented by R ₁ in the general formula (1).

R ₈ to R ₁₁ are each independently preferably substituted with a hydrogen atom, an alkyl group, an aryl group optionally having an alkyl group, an alkyl group or a phenyl group from the viewpoint of charge transportability and charge stability. A silyl group, a cyano group, or a fluorine atom, more preferably a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. Any one of 18 aryl groups, alkyl groups having 1 to 6 carbon atoms, or silyl groups having 3 to 18 carbon atoms substituted with phenyl groups, cyano groups, and fluorine atoms, and more preferably hydrogen atoms, 1 carbon atoms. An alkyl group having 4 to 4 carbon atoms, an aryl group having 6 to 12 carbon atoms which may have an alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 6 carbon atoms, or a phenyl group with 3 to 3 carbon atoms 8 silyl group, is either cyano group, and a fluorine atom.
Among them, R ₈ to R ₁₁ are preferably each independently a hydrogen atom, methyl group, isopropyl group, t-butyl group, neopentyl group, trifluoromethyl group, phenyl group, dimethylphenyl group, trimethylsilyl group, triphenylsilyl group. Group, a fluorine atom, and a cyano group, more preferably a hydrogen atom, a t-butyl group, a phenyl group, a trimethylsilyl group, a triphenylsilyl group, and a cyano group, and more preferably a hydrogen atom. , A t-butyl group, a phenyl group, a triphenylsilyl group, and a cyano group.

The compound represented by the general formula (1) or (2) is most preferably composed of only a carbon atom, a hydrogen atom and a nitrogen atom.

The glass transition temperature (Tg) of the compound represented by the general formula (1) or (2) 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. More preferably, it is 400 degrees C or less.

When the general formula (1) or (2) has a hydrogen atom, an isotope (such as a 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 an isotope may be used.
Although the specific example of a compound represented by general formula (1) or (2) below is illustrated below, this invention is not limited to these.

The compounds exemplified as the compounds represented by the general formula (1) or (2) can be synthesized with reference to International Publication No. 2004/074399 pamphlet and the like. For example, compound (A-1) can be synthesized by the method described in WO 2004/074399, paragraph 52, line 22 to paragraph 54, line 15.

In the present invention, the compound represented by the general formula (1) or (2) is contained in the light emitting layer, but its use is not limited, and it is further contained in any layer in the organic layer. Also good. As the introduction layer of the compound represented by the general formula (1) or (2), 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 layer Either can be mentioned.
The compound represented by the general formula (1) or (2) is preferably included in an amount of 50 to 99.9% by mass, more preferably 50 to 99% by mass, with respect to the total mass of the light emitting layer. It is more preferable to include 98% by mass. When the compound represented by the general formula (1) or (2) is further contained in a layer other than 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 layer. % Is more preferable.

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

(In General Formula (E-1), R _E1 and R _E2 each independently represent a hydrogen atom, an aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group. However, R _E1 and R _E2 are not simultaneously hydrogen atoms.
Ar represents a substituted or unsubstituted arylene group or a substituted or unsubstituted divalent aromatic heterocyclic group.
R _E3 represents a hydrogen atom, an aliphatic hydrocarbon, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group.
R _E4 represents a hydrogen atom, an aliphatic hydrocarbon, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group. )

In the organic electroluminescent device of the present invention, the compound represented by the general formula (E-1) is contained in at least one organic layer between the cathode 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 is because the light emitting layer contains the compound represented by the general formula (1), and at least one organic layer between the light emitting layer and the cathode contains the compound represented by the general formula (E-1). Thus, the electron affinity between the compound represented by the general formula (E-1) and the compound represented by the general formula (1) is in an optimum range, and the electron transport property of the electron transport layer from a low voltage is improved, This is presumably because a large amount of electrons can be transported to the light emitting layer.
Further, it was found that the dependency of the emission chromaticity on the electron transport layer thickness was suppressed in the device of the present invention. Although this cannot be predicted from conventional knowledge, the light emitting layer contains the compound represented by the general formula (1), and the organic layer between the light emitting layer and the cathode has the general formula (E-1). By containing the represented compound, electrons can sufficiently enter the light emitting layer and the light emission distribution is widened, so that the above effect is presumed.

In the general formula (E-1), R _E1 and R _E2 each independently represent a hydrogen atom, an aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group. To express.

When R _E1 and R _E2 represent an aliphatic hydrocarbon group, the aliphatic hydrocarbon group is preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms, and an alkyl group (preferably having 1 to 10 carbon atoms). For example, a methyl group, an ethyl group, an isopropyl group, a t-butyl group, an n-octyl group, an n-decyl group, an n-hexadecyl group, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, and a neopentyl group). An alkenyl group (preferably having 2 to 10 carbon atoms, such as vinyl, allyl, 2-butenyl, 3-pentenyl, etc.) or an alkynyl group (preferably having 2 to 10 carbon atoms such as propargyl, 3 -Pentynyl, etc.) is more preferred, and alkyl groups are more preferred, methyl groups, ethyl groups, isopropyl , Particularly preferably a t- butyl group, or cyclohexyl group.

When R _E1 and R _E2 represent a substituted or unsubstituted aryl group, the aryl group is preferably an aryl having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms. It is a group. 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 preferable, phenyl group, naphthyl group, biphenyl group, or anthryl group is more preferable, and naphthyl group is most preferable. The reason why the naphthyl group is preferable is considered to be that an appropriate interaction between molecules can be generated, whereby a reduction in driving voltage and a stable film quality can be obtained.
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 Preferred is an alkyl group having 1 to 6 carbon atoms, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an isobutyl group, a t-butyl group, an n-butyl group, and a cyclopropyl group. 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, or an aromatic heterocyclic group (preferably an aromatic heterocyclic group having 4 to 12 carbon atoms, such as a pyridyl group, a furyl group, and a thienyl group, and a pyridyl group is more preferable). It is.

When R _E1 and R _E2 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 carbon atoms. It is an aromatic heterocyclic group of 2 to 12. 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. A pyridyl group is more preferred.
When the aromatic heterocyclic group has a substituent, examples of the substituent are the same as those of the substituent that may be present when R _E1 and R _E2 are an aryl group, and the preferred range.

R _E1 and R _E2 are preferably a substituted or unsubstituted aryl group, and more preferably an unsubstituted aryl group from the viewpoint of obtaining an appropriate interaction between molecules. Specific examples and preferred ranges when R _E1 and R _E2 are aryl groups are as described above.

R _E1 and R _E2 may be the same or different from each other, but are preferably the same from the viewpoint of synthesis. However, R _E1 and R _E2 are not simultaneously hydrogen atoms.

In general formula (E-1), Ar represents a substituted or unsubstituted arylene group or a substituted or unsubstituted divalent aromatic heterocyclic group.

When Ar 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 or a naphthylene group is more preferred, and a phenylene group is most preferred.
When the arylene group has a substituent, examples of the substituent are the same as those of the substituent that may be present in the case where R _E1 and R _E2 are an aryl group.

When Ar represents a substituted or unsubstituted divalent aromatic heterocyclic group, the divalent aromatic heterocyclic group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably Is a divalent aromatic heterocyclic group having 2 to 12 carbon atoms. Examples of the divalent aromatic heterocyclic group include a divalent azole group, a divalent diazole group, a divalent triazole group, a divalent oxazole group, a divalent thiazole group, a divalent pyridyl group, A bivalent furyl group, a bivalent thienyl group, etc. are mentioned, A bivalent azole group, a bivalent diazole group, and a bivalent pyridyl group are preferable, and a bivalent pyridyl group (pyridylene group) is more preferable.
In the case where the divalent aromatic heterocyclic group has a substituent, examples of the substituent are the same as those of the substituent that R _E1 and R _E2 may have in the case of an aryl group, and specific examples and preferred ranges thereof. is there.

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

In General Formula (E-1), R _E3 represents a hydrogen atom, an aliphatic hydrocarbon, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group.

When R _E3 represents an aliphatic hydrocarbon group, the aliphatic hydrocarbon group preferably has 1 to 20 carbon atoms and is preferably an alkyl group (preferably having 1 to 10 carbon atoms, such as a 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, etc.), alkenyl group (preferably having a carbon number of 2 to 10 such as vinyl, allyl, 2-butenyl, 3-pentenyl, and the like, or an alkynyl group (preferably having 2 to 10 carbon atoms, such as propargyl, 3-pentynyl, etc.). More preferably, it is an alkyl group, more preferably a methyl group, an ethyl group, an isopropyl group, a t-butyl group, or a cyclohexyl group. Particularly preferred is a xyl group.

When R _E3 represents a substituted or unsubstituted aryl group, the aryl group is preferably an aryl 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 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, and a triphenylenyl group, and a phenyl group, a naphthyl group, a biphenyl group, or the like. An anthryl group is preferable, and a phenyl 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 Preferred is an alkyl group having 1 to 6 carbon atoms, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an isobutyl group, a t-butyl group, an n-butyl group, and a cyclopropyl group. 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, alkoxy group, or aromatic heterocyclic group (preferably an aromatic heterocyclic group having 2 to 12 carbon atoms, such as azole group, diazole group, triazole group, oxazole group, thiazole group, pyridyl group, furyl group) A thienyl group, an azole group, a diazole group, and a pyridyl group are preferable, and a benzoimidazolyl group is particularly preferable.
Further, these substituents may further have a substituent if possible, and examples of the further substituent include a substituent selected from the substituent group A, preferably an alkyl group, an aryl group. , Or an aromatic heterocyclic group, and specific examples and preferred ranges thereof are the same as the specific examples and preferred ranges of the substituent when R _E3 represents a substituted aryl group.
When R _E3 represents an aryl group having a substituent, the substituents may be bonded to each other to form a ring, and examples of the ring include an aliphatic hydrocarbon ring, an aromatic ring, and an aromatic heterocycle. An aromatic ring is preferable, and a benzene ring, a fluorene ring, an anthracene ring, a naphthyl ring, or a ring having a combination thereof, and the like, a fluorene ring, an anthracene ring, or a ring having a combination thereof are included. Is preferred.

When R _E3 represents 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 2 to 2 carbon atoms. 12 aromatic heterocyclic groups. 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. Particularly preferred is a benzimidazolyl group.
When the aromatic heterocyclic 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 an alkyl group having 1 to 6 carbon atoms, such as methyl group, ethyl group, n-propyl group, isopropyl group, isobutyl group, t-butyl group, n-butyl group, cyclopropyl group and the like. A methyl 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). For example, a phenyl group, a biphenyl group, a fluorenyl group, a naphthyl group, and the like. A phenyl group or a biphenyl group is preferable, and a phenyl group is more preferable.), A halogen A child (preferably a fluorine atom), a cyano group, an alkoxy group, or an aromatic heterocyclic group (preferably an aromatic heterocyclic group having 2 to 12 carbon atoms, such as a pyridyl group, a furyl group, and a thienyl group). And a pyridyl group is more preferable. Among these, an aryl group is particularly preferable.

R _E3 is preferably a hydrogen atom or a substituted or unsubstituted aryl group, and more preferably a hydrogen atom from the viewpoint of obtaining an appropriate interaction between molecules.

In General Formula (E-1), R _E4 represents a hydrogen atom, an aliphatic hydrocarbon, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group.

When R _E4 represents an aliphatic hydrocarbon group, the aliphatic hydrocarbon group preferably has 1 to 12 carbon atoms and is preferably an alkyl group (preferably having 1 to 10 carbon atoms, such as a methyl group, an ethyl group, isopropyl Group, t-butyl group, n-octyl group, n-decyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, neopentyl group, etc.), alkenyl group (preferably having 2 to 10 carbon atoms, for example, Vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), or alkynyl groups (preferably having 2 to 10 carbon atoms, such as propargyl, 3-pentynyl, etc.) are more preferred. More preferably, it is a methyl group, an ethyl group, an isopropyl group, a t-butyl group, or a cyclohexyl group. Particularly preferred.

When R _E4 represents a substituted or unsubstituted aryl group, the aryl group is preferably an aryl 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 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. A phenyl group, a naphthyl group, a biphenyl group, or An anthryl group is preferable, a phenyl group or a naphthyl group is more preferable, and a phenyl group is still more preferable.
When the aryl group has a substituent, examples of the substituent are the same as those of the substituent that may be present when R _E1 and R _E2 are an aryl group.

When R _E4 represents 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, particularly preferably 2 to 2 carbon atoms. 12 aromatic heterocyclic groups. 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. A pyridyl group is more preferred.
When the aromatic heterocyclic group has a substituent, examples of the substituent are the same as those of the substituent that may be present when R _E1 and R _E2 are an aryl group, and the preferred range.

R _E4 is preferably a substituted or unsubstituted aryl group, and more preferably an unsubstituted aryl group, from the viewpoint of obtaining an appropriate interaction between molecules. Specific examples and preferred ranges in the case where R _E4 is an aryl group are as described above.

The compound represented by the general formula (E-1) is preferably represented by the following general formula (E-2) or the following general formula (E-3).

(In General Formulas (E-2) and (E-3), R _E1 and R _E2 are each independently a hydrogen atom, an aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted group. However, R _E1 and R _E2 are not simultaneously hydrogen atoms.
R _E3 represents a hydrogen atom, an aliphatic hydrocarbon, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group. )

In general formulas (E-2) and (E-3), R _E1 , R _E2 , and R _E3 are respectively synonymous with R _E1 , R _E2 , and R _E3 in general formula (E-1), and are preferable. The range is the same.

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

Of the above specific examples, (e-1) to (e-10) are more preferred, (e-1) to (e-4), and (e-6) to (e-10) are more preferred, Particularly preferred are e-3), (e-4) and (e-8).

The compound represented by the general formula (E-1) can be synthesized by the method described in Japanese Patent No. 4308663.
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 (E-1) is contained in at least one organic layer between the light emitting layer and the cathode, but its application is not limited. It may be further contained in any layer. As the introduction layer of the compound represented by the general formula (E-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 (E-1) and the cathode is more preferably a charge blocking layer or an electron transporting layer, and further preferably an electron transporting layer. .

[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 consisting of 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 cathode. An element comprising at least one compound represented by the general formula (1) in the light emitting layer and represented by the general formula (E-1) in at least one organic layer between the light emitting layer and the cathode. 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 cathode, 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 For Device Configuration of Organic Electroluminescent Device, Substrate, Cathode and Anode For example, it is described in detail in 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 paragraph numbers [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. In the element of the present invention, at least one of the light emitting layer, the organic layer between the light emitting layer and the cathode, and the other organic layer existing between the anode and the cathode is formed by a solution coating process. It is preferable.

[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 broaden the light emission wavelength region. At least one of the light emitting materials is preferably a phosphorescent light emitting material.
The light emitting material of 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 in paragraph numbers [0100] to [0164] of JP-A-2008-270736 and paragraph numbers [0088] to [0090] of JP-A-2007-266458, for example. The matters described in these publications can be applied to the present invention.

From the viewpoint of luminous efficiency, a phosphorescent material is preferable. Examples of phosphorescent light-emitting materials that can be used in the present invention include US Pat. / 19373A2, JP-A No. 2001-247859, JP-A No. 2002-302671, JP-A No. 2002-117978, JP-A No. 2003-133074, JP-A No. 2002-1235076, JP-A No. 2003-123984, JP-A No. 2002-170684, EP No. 121157, JP-A No. 2002-2000 -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 the light-emitting dopant include Ir complex, Pt complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu complex, and Tb complex. 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.)

The general formula (C-1) will be described. 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, and 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 etc.), 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 bonded 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 thereof. 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 represents a benzene ring or an aromatic heterocycle.

The general formula (C-2) will be described. L ²¹ has the same meaning as L ^{1 in} formula (C-1), and the preferred range is 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, and the substituent group A is a substituent on a carbon atom, and the substituent on a nitrogen atom is 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. Further, when the wavelength is increased, an electron withdrawing group is preferable, and for example, 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.

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 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. Preferred substituents on carbon are alkyl groups, perfluoroalkyl groups, aryl groups, aromatic heterocyclic groups, dialkylamino groups, diarylamino groups, alkoxy groups, cyano groups, and fluorine atoms. 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. For shortening 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.

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

(In the general formula (C-4), A ⁴⁰¹ to A ⁴¹⁴ each independently represents 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.)

The general formula (C-4) will be described.
A ⁴⁰¹ to A ⁴¹⁴ each independently represents 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.
When 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 in 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 Of these, 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 the more preferred embodiments is a platinum complex represented by the following general formula (C-5).

(In the 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.)

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

A ⁵⁰⁷ , A ⁵⁰⁸ and A ⁵⁰⁹ and A ⁵¹⁰ , A ⁵¹¹ and A ⁵¹² and 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 ^CR , 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 , Hydrogen atom, alkyl group, trifluoromethyl group, fluorine atom. Further, when possible, 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 heterocycle, and Y is an anionic acyclic ligand bonded to Pt.)

The general formula (C-6) will be described. 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, and thiocarboxylic acid ligands.
The ligand represented by Y 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.

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).

(Wherein 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.)

The general formula (C-7) will be described. 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 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] in Japanese Patent Publication No. JP-A-2007-324309, Nos. [0079] to [0083] in Japanese Unexamined Patent Publication No. 2007-324309, No. [0065] to [0090] in Japanese Unexamined Patent Publication No. 2006-93542 Compounds described in JP-A-2007-96255, compounds described in [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 column 53 to right column 7, line 790, method described in left column 18 to 38, method 790, method described in right column 19 to 30 and The combination, Chemische Berichte 113, 2749 (1980), H.C. Lexy et al.), Page 2752, lines 26 to 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 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, Represents 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; 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. The condensed 4- to 7-membered ring may be further condensed, and the further condensed ring may 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. Two _RTs may be bonded to each other to form a ring.
Each substituent T 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, and examples of the group that may be substituted include the substituent T described above. The alkyl group represented by R _T3 ′, R _T3 , R _T4 , R _T5 and R _T6 is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms. Groups such as a methyl group, an ethyl group, an i-propyl group, a cyclohexyl group, and a t-butyl group.
The cycloalkyl group may have a substituent, 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 preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. Examples thereof include 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 a group having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. 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 and 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 preferable, and phenyl group, fluorenyl group and naphthyl group are more preferable.

The heteroaryl group represented by R _T3 ′, R _T3 , R _T4 , R _T5 , and R _T6 is preferably a heteroaryl group having 5 to 8 carbon atoms, more preferably a 5- or 6-membered substituent. 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. 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 heterocycle 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 and a pyrazole ring are more preferable.

Examples of the condensed aromatic heterocycle 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 the 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 the 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 ligand (also referred to as a coordination compound) well known by those skilled in the art is optionally used as a ligand represented by (XY). 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. Included in ligands (eg, halogen ligands (preferably chlorine ligands), etc., published in 1987, published by Yersin, “Organometallic Chemistry-Fundamentals and Applications-” 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.
Specific examples of the ligand represented by (XY) are given below, but the present invention is not limited thereto.

In the example of the ligand represented by the above (XY), * represents the 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 not considered 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. (I-1), (I-4) and (I-5) are preferred because complex synthesis is easy, 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, in the same manner as described in International Publication No. 2009-073245, page 46, it can be synthesized by the following method using commercially available difluoroacetylacetone.

In addition, a monoanionic ligand represented by the general formula (I-15) can also be used as the ligand.

R _T7 to R _T10 in general formula (I-15) have the same _{meanings as} R _T3 to R _T6 in general formula (T-1), and the preferred ranges 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 are each independently a hydrogen atom, alkyl group, alkenyl group, alkynyl group, —CN, perfluoroalkyl group, trifluorovinyl. Group, —CO ₂ R _T , —C (O) R _T , —N (R _T ) ₂ , —NO ₂ , —OR _T , a fluorine atom, an aryl group or a heteroaryl group, and further having a substituent T You may do it.
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 further has a substituent Z 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.
Each substituent T 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 R _T3 ′, R _T4 ′, R _T5 ′, R _T6 ′, R _T3 , R _{T4 in} the general formula (T-2). , R _T5 and R _T6 , any two adjacent groups are not bonded to each other to form a condensed ring.

One preferred form 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 _~ 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 are also the same. R _T7 ′ to R _T10 ′ have the same _meanings as R _T3 ′ to R _T6 ′, and preferred ranges are also the same.

Another preferred embodiment 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). It is synonymous with _T3 to R _T6 , (XY), m and n, and the preferred 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 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 to R _{T6 have the same meanings} as (XY), m and n, and the preferred ones are also the same.

Another preferred 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). Further, it is particularly preferable that 0 to 2 of R _1a to R _1i are alkyl groups or aryl groups and the rest are all hydrogen atoms. The definitions and preferred ranges of (XY), m, and n are the same as (XY), m, and n in formula (T-1).

Another preferred 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 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, or 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, and further having a substituent T You may do it.
R _T3 , R _T4 , R _T5 and R _T6 may be combined with 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 'are} two arbitrary adjacent but may form a fused 4-7 membered ring bonded to each other, the condensed 4-7 membered ring may further have a substituent group 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.
Each substituent T 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 ′, R _T3 to R _T6 , (XY), m and n in the general formula (TC-1) are preferably in the ranges R _T3 ′, R _T3 to R _T6 in the general formula (T-1), 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, preferably methyl group, ethyl group, isopropyl group and t-butyl group, more preferably methyl group.

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 the 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 the 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 'are} two arbitrary adjacent but may form a fused 4-7 membered ring bonded to each other, the condensed 4-7 membered ring may further have a substituent group 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.
Each substituent T 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 preferably have 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 preferred range of R _TC1 to R _{TC4 is the same as} the preferred 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, and 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.

Preferred specific examples of the compound represented by the general formula (T-1) are listed below, but are not limited thereto.

The compounds exemplified as the compound represented by the general formula (T-1) can be synthesized by the method described in JP2009-99783A or various methods described in US Pat. No. 7,279,232. 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 a 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. (XY), n, and m have the same meanings as (XY), n, and m in formula (T-2), and the preferred ranges are also the same.

These preferred specific examples are listed below, but are not limited to the following.

The light emitting material in the light emitting layer is generally contained in the light emitting layer in an amount of 0.1% by mass to 50% by mass with respect to the total mass of the compound forming the light emitting layer. 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.

The thickness of the light emitting layer is not particularly limited, but is usually preferably 2 nm to 500 nm, and 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.
Further, 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 anhydrides such as naphthaleneperylene, metal complexes of phthalocyanine and 8-quinolinol derivatives, metal phthalocyanines, metal complexes having benzoxazole and benzothiazol 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 is 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 blocking layer, or a light emitting layer, it is possible to manufacture 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.
The thickness of the hole transport 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 thickness of the hole injection layer is preferably from 0.1 nm to 200 nm, more preferably from 0.5 nm to 100 nm, and even more preferably from 1 nm to 100 nm.
The following compounds can also be preferably used as the hole injection 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 lowered, 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), tetrafluorotetracyanoquinodimethane (F ₄ -TCNQ), molybdenum oxide, and the like.

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 preferably 0.1% by mass to 40% by mass with respect to the total mass of the compound 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 thickness of the electron transport 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 thickness of the electron injection layer is preferably from 0.1 nm to 200 nm, more preferably from 0.2 nm to 100 nm, and even more preferably from 0.5 nm to 50 nm.
In the device of the present invention, the electron transport layer preferably contains a compound represented by the general formula (E-1).
The electron injection layer preferably contains an electron donating dopant. By containing 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 preferably 0.1% by mass to 40% by mass with respect to the total mass of the compound forming the electron injection layer. More preferably, the content is 0.5 to 30% by mass.

By incorporating an electron-accepting dopant in the hole-injecting layer and an electron-donating dopant in the electron-injecting layer, it is generally possible to promote charge injection from the electrode and lower the driving voltage. If the charge balance in the light source is lost, the light emission position may change, and the light emission efficiency, drive durability, and various changes during high-intensity driving may be promoted. The device of the present invention has a small charge trap in the light emitting layer adjacent layer / light emitting layer interface on the cathode side and a small charge trap in the light emitting layer or the light emitting layer adjacent layer on the cathode side. Because of the good balance between the electron mobility of the adjacent light emitting layer on the side, the hole mobility and the electron mobility of the light emitting layer, etc. By including an electron-accepting dopant in the hole-injecting layer and an electron-donating dopant in the electron-injecting layer, the driving voltage can be reduced without deteriorating efficiency, durability, various changes during high-intensity driving, etc. it can.

(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.
Examples of the organic compound constituting the hole blocking layer include 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 ( And phenanthroline derivatives such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (abbreviated as BCP)), triphenylene derivatives, and carbazole derivatives.
The triphenylene derivatives are described in, for example, International Publication No. 05/013388, International Publication No. 06/130598, and International Publication No. 09/021107. The triphenylene derivative is preferably a compound represented by the following general formula (Tp-1).

(In the general formula (Tp-1), R ¹² to R ²³ are each independently a hydrogen atom, an alkyl group or an alkyl group, a phenyl group optionally substituted with a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, Represents a fluorenyl group, a naphthyl group, or a triphenylenyl group, provided that R ¹² to R ²³ are not all hydrogen atoms.)

Examples of the alkyl group represented by R ¹² to R ²³ include methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, n-octyl group, n-decyl group, n-hexadecyl group, and cyclopropyl. A methyl group, an ethyl group, an isopropyl group, a t-butyl group, and a cyclohexyl group, and more preferably a methyl group, an ethyl group, or a t-butyl group.

R ¹² to R ²³ are preferably an alkyl group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group (these are further an alkyl group, a phenyl group, a fluorenyl group). More preferably a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, which may be substituted with a group, a naphthyl group, or a triphenylenyl group.
The thickness of the hole blocking layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100 nm.
The hole 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.
As for the protective layer, the matters described in JP-A-2008-270736, paragraphs [0169] to [0170] 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 [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-5-290080, JP-A-7-134558, JP-A-8-234585, 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 shape of the substrate, the shape of the electrode, the thickness of the organic layer, the thickness of the inorganic layer, the refractive index of the organic layer, the refractive index of the inorganic layer, 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, it can be a display device such as a television, a personal computer, a mobile phone, and electronic paper in addition to a lighting device.

(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.

Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited thereto.

The compound represented by the general formula (1) used in the examples was synthesized with reference to International Publication No. 2004/074399 pamphlet and the like. For example, compound (1) can be synthesized by the method described in International Publication No. 2004/074399, page 52, line 22 to page 54, line 15.
The compound represented by the general formula (E-1) was synthesized with reference to Japanese Patent No. 4308663.

The organic materials used in this example were all purified by sublimation and analyzed by high performance liquid chromatography (Tosoh TSKgel ODS-100Z). Purity of 99.9 was obtained unless the absorption intensity area ratio was 254 nm. % Or more was used.

[Example 1]
<Production of organic electroluminescence device>
A glass substrate (ITO film thickness is 100 nm) having an indium tin oxide (ITO) film with a thickness of 0.7 mm and a 2.5 cm square is placed in a cleaning container, subjected to ultrasonic cleaning in 2-propanol, and then UV-ozone for 30 minutes. Processed. The following layers were deposited on this glass substrate by a vacuum deposition method using a vacuum deposition apparatus (Small-ELVESS, manufactured by Tokki Co., Ltd.). In addition, all the vacuum evaporation methods in a following example and a comparative example are performed on the same conditions, and a vapor deposition rate is 0.2 nm / sec unless there is particular notice. The deposition rate was measured using a quartz resonator. The pressure is 1 × 10 ⁻⁴ Pa or less. The thickness of each layer below was measured using a quartz resonator.
On the anode (ITO), HIL-1 (purity 97%) was formed as a hole injection layer by vacuum deposition so as to have a thickness of 10 nm.
Next, N, N′-dinaphthyl-N, N′-diphenyl- [1,1′-biphenyl] -4,4′-diamine (NPD) is formed as a hole transport layer on the hole injection layer. It was formed by vacuum deposition so as to be 30 nm.
Next, a light emitting layer containing 85:15 by mass ratio of the compound (A-1) (host material) and the light emitting material Ir-A (guest) on the hole transport layer so as to have a thickness of 30 nm. A film was formed by vacuum deposition.
Next, a hole blocking layer was formed on the light emitting layer by vacuum deposition of HBL-A to a thickness of 10 nm.
Next, e-4 was deposited as an electron transport layer on the hole blocking layer by vacuum deposition so as to have a thickness of 30 nm.
Next, LiF was deposited as an electron injection layer on the electron transport layer by vacuum deposition so that the thickness was 1 nm.
Next, a patterned mask (a mask having a light emitting area of 2 mm × 2 mm) was set as a cathode, and metal aluminum was vacuum deposited to a thickness of 100 nm to form a film.
The laminate produced as described above was placed in a glove box substituted with argon gas, and sealed with a glass sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.). Thus, the organic electroluminescent element of Example 1 was produced.
In addition, in order to measure the amount of change in chromaticity depending on the thickness of the electron transport layer, an element manufactured in the same manner as described above except that the electron transport layer was thickened by 10 nm and the same as the above except that the electron transport layer was thinned by 10 nm. A device manufactured as described above was also manufactured.

(Evaluation)
The organic electroluminescence device of Example 1 produced was evaluated for light emission efficiency, drive voltage, durability, and chromaticity as follows. Roll-off (decrease in efficiency during high-intensity drive) and electron transport layer thickness of about 10 nm The amount of change in chromaticity x was calculated.

<Measurement of luminous efficiency and driving voltage>
The emission luminance of the organic electroluminescence device driven at a constant current density (10 mA / cm ² ) was measured with a spectral radiance meter (SR-3, manufactured by Topcon Corporation), and the external quantum efficiency (%) was determined.
The voltage at that time was measured and used as the drive voltage (V).
In Table 1, the external quantum efficiency and driving voltage of Comparative Example 3 are set to 100 in Table 1, the external quantum efficiency and driving voltage of Comparative Example 11 are set to 100 in Table 2, and the external quantum efficiency of Comparative Example 17 is set to Table 3 in Table 3. In Table 4, the external quantum efficiency and the driving voltage of Comparative Example 24 are set to 100, and are shown as relative values.
<Measurement of durability>
Luminance 1,000 cd / ^m while maintaining the current density at ^second organic electroluminescent device of the continuous light emission is allowed time until the luminance 500 cd / ^{m 2} to (h) was calculated as the durability.
In Table 1, the durability of Comparative Example 3 is set to 100, in Table 2, the durability of Comparative Example 11 is set to 100, in Table 3, the durability of Comparative Example 17 is set to 100, and in Table 4, the durability is compared. The durability of Example 24 was taken as 100, and is shown as a relative value.

<Calculation of roll-off>
In the light emission efficiency at a luminance of 1,000 cd / ^{m 2,} it was evaluated rolloff value obtained by dividing the emission efficiency at a luminance 10,000cd / ^{m 2.} It can be said that roll-off is suppressed as the value increases. The luminous efficiency was measured in the same manner as described above.

<Measurement of chromaticity>
A DC constant voltage was applied to the organic electroluminescence device of Example 1 to emit light using a source measure unit type 2400 manufactured by Toyo Technica. The obtained emission spectrum was measured with an emission spectrum measurement system (ELS1500) manufactured by Shimadzu Corporation, and an x value was calculated from the obtained spectrum using a CIE color system. The x value is a value at a current density of 10 mA / cm ² .

<Calculation of change amount of chromaticity x per 10 nm of electron transport layer thickness>
The amount of change in chromaticity x per 10 nm of the electron transport layer (film thickness on the x-axis and chromaticity on the y-axis) from the chromaticity x measured for three elements having different electron transport layer thicknesses by the least square method. (slope per x-axis of 10 nm) was calculated.

[Examples 2 to 31, and 33, and Comparative Examples 1 to 27 and 29]
An element was prepared and evaluated in the same manner as in Example 1 except that the element configuration, the thickness of each layer, the compound used in each layer, and the content thereof were changed as shown in Tables 1 to 4 below. In Tables 1 to 4, the guest content of the light emitting layer is mass% with respect to the total mass of the light emitting layer.
[Example 32 and Comparative Example 28]
On the surface of the glass substrate having the washed indium tin oxide (ITO) film, an aqueous solution of poly (3,4-ethylenedioxythiophene) -poly (styrenesulfonic acid (PEDOT / PSS) (manufactured by Bayer) at 3000 to 4000 rpm. The device of Example 32 was prepared and evaluated in the same manner as Example 22 except that the hole injection layer was formed by spin coating at a rotational speed of approximately, removing the film other than the light emitting region and then baking at 200 ° C. Further, a device of Comparative Example 28 was fabricated and evaluated in the same manner as in Example 32 except that the host material of the light emitting layer was changed to mCP.

[Comparative Example 30]
The device of Comparative Example 30 was prepared and evaluated in the same manner as in Example 1 except that the device configuration, the thickness of each layer, the compound used in each layer, and the content thereof were changed as shown in Table 5 below. The results are shown in Table 5 below.

From Table 5, the element of Comparative Example 30 is significantly inferior to the element of Example 1 in suppressing reduction in efficiency (roll-off) during high-intensity driving and in suppressing the dependence of chromaticity on the electron transport layer thickness. I understand.

It can be seen from the results in Tables 1 to 5 that roll-off of the device of the example is suppressed and that the chromaticity is less dependent on the electron transport layer thickness than the device of the comparative example.

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

Although the present invention has been described in detail and with reference to specific embodiments, it will be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the invention.
This application is based on a Japanese patent application (Japanese Patent Application No. 2010-157356) filed on Jul. 9, 2010, the contents of which are incorporated herein by reference.

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

Claims

An organic electroluminescent device having a pair of electrodes consisting of 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 cathode,
The light emitting layer contains at least one compound represented by the following general formula (1),
An organic electroluminescence device comprising at least one compound represented by the following general formula (E-1) in at least one organic layer between the light emitting layer and the cathode.

(In the general formula (1), R 1 represents an alkyl group, an aryl group, or a silyl group, and may further have a substituent Z, provided that R 1 represents a carbazolyl group or a perfluoroalkyl group. If no .R 1 there are a plurality, the plurality of R 1 each may be the same or different. the plurality of R 1 may form an aryl ring which may have a substituent Z bonded to each other May be.
R 2 to R 5 each independently represents an alkyl group, an aryl group, a silyl group, a cyano group, or a fluorine atom, and may further have a substituent Z. When a plurality of R 2 to R 5 are present, the plurality of R 2 to R 5 may be the same as or different from each other.
The substituent Z represents an alkyl group, an alkenyl group, an aryl group, an aromatic heterocyclic group, an alkoxy group, a phenoxy group, a fluorine atom, a silyl group, an amino group, a cyano group, or a group formed by combining these, and a plurality of substituents Z may combine with each other to form an aryl ring.
n1 represents an integer of 0 to 5.
n2 to n5 each independently represents an integer of 0 to 4. )

(In General Formula (E-1), R E1 and R E2 each independently represent a hydrogen atom, an aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group. However, R E1 and R E2 are not simultaneously hydrogen atoms.
Ar represents a substituted or unsubstituted arylene group or a substituted or unsubstituted divalent aromatic heterocyclic group.
R E3 represents a hydrogen atom, an aliphatic hydrocarbon, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group.
R E4 represents a hydrogen atom, an aliphatic hydrocarbon, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group. )
The organic electroluminescent element according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (2).

(In General Formula (2), R 6 and R 7 each independently represents an alkyl group which may have a substituent Z, an aryl group which may have an alkyl group, a cyano group or a fluorine atom. When a plurality of R 6 and R 7 are present, the plurality of R 6 and the plurality of R 7 may be the same as or different from each other, and the plurality of R 6 and the plurality of R 7 are bonded to each other. An aryl ring which may have a substituent Z may be formed.
n6 and n7 each independently represents an integer of 0 to 5.
R 8 to R 11 are each independently a hydrogen atom, an alkyl group optionally having substituent Z, an aryl group optionally having alkyl group, or a silyl group optionally having substituent Z Represents a cyano group or a fluorine atom.
The substituent Z represents an alkyl group, an alkenyl group, an aryl group, an aromatic heterocyclic group, an alkoxy group, a phenoxy group, a fluorine atom, a silyl group, an amino group, a cyano group, or a group formed by combining these, and a plurality of substituents Z may combine with each other to form an aryl ring. )
The organic electroluminescent device according to claim 1 or 2, wherein R E4 in the general formula (E-1) is an unsubstituted aryl group.
The organic electroluminescent element according to any one of claims 1 to 3, wherein, in the general formula (E-1), Ar is an unsubstituted arylene group.
The organic electroluminescence device according to any one of claims 1 to 4, wherein R E4 in the general formula (E-1) is a phenyl group.
6. The organic electroluminescent element according to claim 1, wherein Ar is a phenylene group in the general formula (E-1).
The organic electroluminescent element according to any one of claims 1 to 6, wherein the general formula (E-1) is represented by the following general formula (E-2) or the following general formula (E-3).

(In General Formulas (E-2) and (E-3), R E1 and R E2 are each independently a hydrogen atom, an aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted group. However, R E1 and R E2 are not simultaneously hydrogen atoms.
R E3 represents a hydrogen atom, an aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group. )
The organic electroluminescence device according to any one of claims 1 to 7, wherein R E3 is a hydrogen atom.
The organic electroluminescence device according to any one of claims 1 to 8, wherein R E1 and R E2 are each independently a naphthyl group.
10. 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 10, wherein the phosphorescent light-emitting material is a compound represented by the following general formula (T-1).

(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, Represents 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; 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.
Each substituent T 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 organic electric field according to any one of claims 1 to 11, wherein at least one of the light-emitting layer and another organic layer existing between the anode and the cathode is formed by a solution coating process. Light emitting element.
A light emitting device using the organic electroluminescent element according to any one of claims 1 to 12.
A display device using the organic electroluminescent element according to any one of claims 1 to 12.
An illumination device using the organic electroluminescent element according to any one of claims 1 to 12.