KR101995080B1 - Organic electroluminescent element - Google Patents

Abstract

It is an object of the present invention to provide a light emitting device which is superior in terms of luminous efficiency, driving voltage and durability, has less deterioration in efficiency at the time of driving with high luminance and has a film thickness of a layer containing a compound having electron- Which is difficult to depend on the emission chromaticity of the organic EL device. An organic electroluminescent device having a pair of electrodes made of a positive electrode and a negative electrode and a light emitting layer between the electrodes and having at least one organic layer between the light emitting layer and the negative electrode on a substrate, A-1), and at least one organic layer between the light-emitting layer and the cathode includes, for example, (e-1) shown below.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent device,

The present invention relates to an organic electroluminescent device.

BACKGROUND ART [0002] Organic electroluminescent devices (hereinafter also referred to as " devices ", also referred to as " organic EL devices ") have been actively researched and developed in that high- The organic electroluminescent device has an organic layer between a pair of electrodes, and the electrons injected from the cathode and the holes injected from the anode are recombined in the organic layer, and the generated exciton energy is used for light emission.

In recent years, by using a phosphorescent material, the efficiency of the device has been increased. In addition, a doped device using a light emitting layer doped with a light emitting material into a host material is widely used.

For example, Patent Document 1 describes an organic electroluminescent device using an iridium complex as a phosphorescent material and a compound containing a carbazole structure as a host material in a light emitting layer.

Further, for the purpose of improving the efficiency and durability of an organic electroluminescent device, a compound having an electron transporting property has been developed.

For example, Patent Document 2 discloses an organic electroluminescent device in which an electron transport layer comprising a specific compound including an anthracene structure and a benzimidazole structure is formed between a light emitting layer containing a fluorescent light emitting material and a cathode.

Patent Document 3 discloses a light-emitting layer in which an iridium complex is used as a phosphorescent light-emitting material, 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- An electron transport layer made of a specific compound is formed.

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

Japanese Laid-Open Patent Publication No. 2008-147353 Japanese Patent Publication No. 4308663 WO 08/015949 Japanese Unexamined Patent Publication No. 2005-515233 WO 08/133483

For example, in a lighting application, driving at a high luminance of about 10,000 cd / m 2 is considered. According to the study of the inventors of the present invention, in a conventional organic electroluminescent device, (Roll-off phenomenon) was remarkable.

In addition, in the conventional organic electroluminescent device, since the host material has low electron transporting property, light emission occurs near the interface between the light emitting layer and the electron transporting layer, and the emission chromaticity is largely changed when the thickness of the electron transporting layer is changed. I could.

In addition, there is a demand for a device having a high luminous efficiency, a low driving voltage, and high durability while solving the above problems.

It is an object of the present invention to provide an organic electroluminescent device which is excellent in terms of luminous efficiency, driving voltage and durability, has a small decrease in efficiency at the time of high-luminance driving, And to provide an organic electroluminescent device in which the film thickness of the layer hardly depends on the emission chromaticity of the device.

According to the study by the present inventors, it is possible to solve the above problems by containing a specific compound containing a carbazole structure in a light emitting layer and containing a specific compound containing an anthracene structure and a benzimidazole structure in a layer on the cathode side of the light emitting layer I found out.

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

[One]

An organic electroluminescent device having a pair of electrodes composed of an anode and a cathode and a light emitting layer between the electrodes and having at least one organic layer between the light emitting layer and the cathode,

Wherein the light emitting layer contains at least one compound represented by the following general formula (1)

And at least one compound represented by the following formula (E-1) is contained in at least one organic layer between the light emitting layer and the cathode.

[Chemical Formula 1]

(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. However, R ₁ does not represent a carbazolyl group or a perfluoroalkyl group. when R ₁ is a plurality is present, a plurality of R ₁ is, each may be the same or different; a plurality of R ₁ is in addition, the aryl ring may be formed which may have the substituents Z bonded to each other.

R ₂ to R ₅ Each independently represent an alkyl group, an aryl group, a silyl group, a cyano group or a fluorine atom, and may further have a substituent Z. R ₂ to R ₅ A plurality of R < _{2 >} to a plurality of R < ₅ > May be the same or different.

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 substituents Z, .

n1 represents an integer of 0 to 5;

and n2 to n5 each independently represent an integer of 0 to 4.)

(2)

(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. However, R _E1 and R _E2 Is not a hydrogen atom at the same time.

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 device according to [1], wherein the compound represented by the general formula (1) is represented by the following general formula (2).

(3)

(In the general formula (2), R ₆ and R ₇ Each independently represent 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. R ₆ and R ₇ A plurality of R < ₆ > and a plurality of R < ₇ > May be the same or different. Also 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 a substituent Z.

n6 and n7 each independently represent an integer of 0 to 5;

R ₈ to R ₁₁ Each independently represent a hydrogen atom, an alkyl group which may have a substituent Z, an aryl group which may have an alkyl group, a silyl group which may have a substituent Z, 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 substituents Z, May be formed.

[3]

In the general formula (E-1), R _E4 The organic electroluminescent device according to the above [1] or [2], wherein the substituent is an unsubstituted aryl group.

[4]

The organic electroluminescent device according to any one of [1] to [3], wherein in the general formula (E-1), Ar is an unsubstituted arylene group.

[5]

In the general formula (E-1), R _E4 The organic electroluminescent device according to any one of the above [1] to [4], wherein the organic group is a phenyl group.

[6]

The organic electroluminescent device according to any one of [1] to [5], wherein in the general formula (E-1), Ar is a phenylene group.

[7]

The organic electroluminescent device according to any one of the above items [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)

[Chemical Formula 4]

(In the formulas (E-2) and (E-3), 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 Is not a hydrogen atom at the same time.

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]

The R _E3 (1) to (7), wherein R < 1 > is a hydrogen atom.

[9]

The R _E1 and R _E2 The organic electroluminescent device according to any one of the above [1] to [8], wherein each of R 1 and R 2 is independently a naphthyl group.

[10]

The organic electroluminescent device according to any one of the above items [1] to [9], wherein the light emitting layer contains a phosphorescent light emitting material.

[11]

The organic electroluminescent device according to the above [10], wherein the phosphorescent light emitting material is a compound represented by the following formula (T-1).

[Chemical Formula 5]

(In the general formula (T-1), R _T3 ', R _T3 , R _T4 , R _T5 and R _T6 They are each independently a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cyano group, a vinyl group to a perfluoroalkyl group, _{trifluoromethyl, -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 may further have a substituent T.

E represents a carbon atom or a nitrogen atom.

Q is a 5- or 6-membered aromatic heterocyclic ring or condensed aromatic heterocyclic ring containing at least one nitrogen.

In the ring Q, a line connecting E and N is represented by one line, and may be a single bond or a double bond, regardless of the bonding species.

R _T3 , R _T4 , R _T5 and R _T6 May be bonded to each other to form a condensed 4- to 7-membered ring. The condensed 4- to 7-membered ring may be cycloalkyl, aryl or heteroaryl, and the condensed 4- to 7-membered ring may further have a substituent T.

R _T3 'and R _{T6 Is, -C (R T) 2 -C} (R T) 2 -, -CR T = CR T -, -C (R T) 2 -, -O-, -NR T -, -OC (R T) ₂ -, -NR _T -C (R _T ) ₂ - and -N = CR _T -, and R _T Each independently represent 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 is independently selected from the group consisting of a fluorine atom, -R ', -OR', -N (R ') ₂ , -SR', -C (O) _{) N (R ') 2,} -CN, -NO 2, -SO 2, -SOR', -SO 2 R represents a ', or -SO ₃ R', R 'are, each independently, a hydrogen atom, an alkyl group, A perfluoroalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

(X-Y) 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]

The organic electroluminescent device according to any one of [1] to [11], 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.

[13]

A light emitting device using the organic electroluminescent device according to any one of [1] to [12].

[14]

A display device using the organic electroluminescent device according to any one of [1] to [12].

[15]

An illumination device using the organic electroluminescent device according to any one of [1] to [12].

[16]

An organic electroluminescent device having a pair of electrodes composed of an anode and a cathode and a light emitting layer between the electrodes and having at least one organic layer between the light emitting layer and the cathode,

Wherein the light emitting layer contains at least one compound represented by the following general formula (1)

A phosphorescent light-emitting material represented by the following general formula (T-1) is contained in the light-emitting layer,

And at least one compound represented by the following formula (E-1) is contained in at least one organic layer between the light emitting layer and the cathode.

[Chemical Formula 6]

(Formula (1) of, R ₁ represents an alkyl group, or an aryl group, or may have a substituent Z further. However, there is no case where R ₁ represents an alkyl group as a carbazolyl group, or a perfluoroalkyl group. The R ₁ When there are a plurality of R _{1 s} , the plurality of R _{1 s} may be the same or different. The plurality of R _{1 s} may combine with each other to form an aryl ring which may have a substituent Z.

R ₂ to R ₅ Each independently represent an alkyl group, an aryl group, a silyl group, a cyano group or a fluorine atom, and may further have a substituent Z. R ₂ to R ₅ A plurality of R < _{2 >} to a plurality of R < ₅ > May be the same or different.

The substituent Z represents an alkyl group, an aryl group, or a fluorine atom.

n1 represents an integer of 1 to 4;

and n2 to n5 each independently represents an integer of 0 to 4.)

(7)

(In the 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.)

[Chemical Formula 8]

(In the general formula (T-1), R _T3 ', R _T3 , R _T4 , R _T5 and R _T6 They are each independently a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cyano group, a vinyl group to a perfluoroalkyl group, _{trifluoromethyl, -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 may further have a substituent T.

E represents a carbon atom or a nitrogen atom.

Q is a 5- or 6-membered aromatic heterocyclic ring or condensed aromatic heterocyclic ring containing at least one nitrogen.

In the ring Q, a line connecting E and N is represented by one line, and may be a single bond or a double bond, regardless of the bonding species.

R _T3 , R _T4 , R _T5 and R _T6 may be bonded to each other to form a condensed 4- to 7-membered ring, the condensed 4- to 7-membered ring is cycloalkyl, aryl or heteroaryl, The condensed 4- to 7-membered ring may further have a substituent T.

R _T3 'and R _{T6 Is, -C (R T) 2 -C} (R T) 2 -, -CR T = CR T -, -C (R T) 2 -, -O-, -NR T -, -OC (R T) ₂ -, -NR _T -C (R _T ) ₂ - and -N = CR _T -, and R _T Each independently represent 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 is independently selected from the group consisting of a fluorine atom, -R ', -OR', -N (R ') ₂ , -SR', -C (O) _{) N (R ') 2,} -CN, -NO 2, -SO 2, -SOR', -SO 2 R represents a ', or -SO ₃ R', R 'are, each independently, a hydrogen atom, an alkyl group, A perfluoroalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

(X-Y) 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 electroluminescent device according to [16], wherein the compound represented by the general formula (1) is represented by the following general formula (2).

[Chemical Formula 9]

(In the general formula (2), R ₆ and R ₇ Each independently represent an alkyl group, an aryl group or a fluorine atom. R ₆ and R ₇ A plurality of R < ₆ > and a plurality of R < ₇ > May be the same or different. Also 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 a substituent Z.

n6 and n7 each independently represent an integer of 0 to 2;

R ₈ to R ₁₁ each independently represent a hydrogen atom, an alkyl group which may have a substituent Z, an aryl group which may have an alkyl group, a silyl group which may have a substituent Z, a cyano group or a fluorine atom.

Substituent Z represents an alkyl group, an aryl group, or a fluorine atom.)

[18]

In the general formula (E-1), R _E4 The organic electroluminescent device according to the above [16] or [17], wherein the substituent is an unsubstituted aryl group.

[19]

The organic electroluminescent device according to any one of the above items [16] to [18], wherein in the general formula (E-1), Ar is an unsubstituted arylene group.

[20]

In the general formula (E-1), R _E4 The organic electroluminescent device according to any one of the above [16] to [19], wherein the organic group is a phenyl group.

[21]

The organic electroluminescent device according to any one of the above items [16] to [20], wherein in the general formula (E-1), Ar is a phenylene group.

[22]

The organic electroluminescent device according to any one of items [16] to [21], wherein the general formula (E-1) is represented by the following formula (E-2) or the following formula (E-3)

[Chemical formula 10]

(In the formulas (E-2) and (E-3), R _E1 and R _E2 Each independently represent an unsubstituted aryl group or an unsubstituted pyridyl group.

R _E3 Represents a hydrogen atom or an unsubstituted aryl group.

[23]

The R _E3 Is an oxygen atom or a sulfur atom, and R < 2 > is a hydrogen atom.

[24]

The R _E1 and R _E2 Is an naphthyl group, and each of R < 1 > and R < 2 > independently represents a naphthyl group.

[25]

The organic electroluminescent device according to any one of the above items [16] to [24], 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.

[26]

A light emitting device using the organic electroluminescent device according to any one of the above [16] to [25].

[27]

A display device using the organic electroluminescent device described in any one of the above [16] to [25].

[28]

An illumination device using the organic electroluminescent device according to any one of [16] to [25].

According to the present invention, it is possible to provide a light emitting device which is excellent in terms of luminous efficiency, driving voltage and durability, has a small decrease in efficiency at the time of high-luminance driving and has a film thickness of a layer containing a compound having electron- It is possible to provide an organic electroluminescent device in which the emission chromaticity is hardly dependent.

1 is a schematic view showing an example of the configuration of an organic electroluminescence device according to the present invention.
2 is a schematic view showing an example of a light-emitting device related to the present invention.
3 is a schematic view showing an example of a lighting apparatus according to the present invention.
4 is a compound included in the organic electroluminescent device according to the present invention.

The hydrogen atom in the description of the general formula (1) and the general formula (E-1) also includes a isotope (deuterium atom and the like), and the atom constituting the substituent also includes the isotope.

In the present invention, substituent group A, substituent group B, and substituent Z are defined as follows.

(Substituent group A)

(Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, t-butyl, n- (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably a carbon number < RTI ID = 0.0 > (Preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl and 3-pentenyl) (Preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as propargyl and 3-pentynyl), an aryl group For example, phenyl, 4-methylphenyl, 2,6-dimethylphenyl, etc., (Preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, (Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, and examples include divalent amino groups such as dibenzylamino, diphenylamino and ditolylamino), alkoxy groups (Preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably methoxy, ethoxy, butoxy, 2-ethylhexyloxy and the like) (Preferably having 1 to 30 carbon atoms, more preferably 1 to 30 carbon atoms, more preferably 1 to 10 carbon atoms, To 20, particularly preferably 1 to 12 carbon atoms, and examples include (Preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 carbon atoms), and examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, (Preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably a carbon number < RTI ID = 0.0 > (Preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, and examples thereof include methoxycarbonyl and ethoxycarbonyl), aryloxycarbonyl groups (Preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms), an acyloxy group (preferably having 1 to 10 carbon atoms and having 7 to 12 carbon atoms such as phenyloxycarbonyl) For example, acetoxy, benz (Preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms, such as acetylamino, benzoylamino and the like) , An alkoxycarbonylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino) , An aryloxycarbonylamino group (preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, and particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonylamino) Sulfonylamino group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino, benzenesulfonylamino and the like) (Preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 12 carbon atoms, for example, sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, (Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as carbamoyl, methyl (meth) acrylate, (Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 20 carbon atoms), an alkylthio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, (Preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and most preferably 1 to 12 carbon atoms, and examples thereof include methylthio and ethylthio) For example, phenylthio, etc.), (Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimidazolylthio, 2-benzoxa (Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as, for example, (Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as methanesulfinyl, benzenesulfonyl, tosyl, etc.) (Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as ureido, methylureido, phenyl Ureido, etc.), a phosphoric acid amide group (Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as diethylphosphoric acid amide and phenylphosphoric acid amide) A mercapto group, a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxyl group, a sulfino group, a hydrazino group, , A heterocyclic group (including an aromatic heterocyclic ring, preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, An atom, a selenium atom and a tellurium atom, and specific examples thereof include pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl, Zolyl, Wherein R is selected from the group consisting of pyridyl, quinolyl, furyl, thienyl, selenophenyl, teruranophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, benzoimidazolyl, benzothiazolyl, A silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, such as a benzoyl group, an azepinyl group, and a silyl group) (Preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, and particularly preferably 3 to 24 carbon atoms, such as trimethylsilyl, triphenylsilyl and the like), a silyloxy group Silyloxy, triphenylsilyloxy and the like), and a phosphoryl group (for example, a diphenylphosphoryl group, a dimethylphosphoryl group and the like). These substituents may be further substituted, and examples of the additional substituent include groups selected from Substituent Group A described above.

(Substituent group B)

(Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, t-butyl, n- , an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms) such as methyl, ethyl, propyl, isopropyl, (Preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 20 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl and 3-pentenyl) (Preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably a carbon number < RTI ID = 0.0 > 6 to 12, and examples thereof include phenyl, p-methylphenyl, naphthyl, anthranyl, etc. Preferably 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom (for example, an oxygen atom, a sulfur atom), a cyano group, a heterocyclic group (including an aromatic heterocyclic ring) And examples thereof include an atom, a phosphorus atom, a silicon atom, a selenium atom and a tellurium atom. Specific examples thereof include pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, Wherein the substituent is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, alkenyl, alkynyl, alkynyl, alkynyl, isoheteroaryl, A thiazolyl group, a benzothiazolyl group, a carbazolyl group, an azepinyl group, and a silyl group). These substituents may be further substituted. As the additional substituent, there may be mentioned a group selected from the above substituent group B. The substituent group substituted by a substituent group may be further substituted, and as the additional substituent group, there may be mentioned a group selected from Substituent Group B described above. The substituent group substituted with a substituent group may be further substituted, and examples of the substituent group include groups selected from Substituent Group B described above.

(Substituent Z)

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 substituents. Even when plural substituents Z are bonded to each other to form an aryl ring do.

The substituent Z is preferably an alkyl group, an aryl group, a fluorine atom or a cyano group, and more preferably an alkyl group, an aryl group or a fluorine atom.

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, such as methyl group, ethyl group, n-propyl group, isopropyl group, butyl group, cyclopropyl group and the like, and 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, 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, 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 are exemplified, and 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, Dissociation 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 methoxy group, ethoxy group, n-propoxy group, A methoxy group, an ethoxy group, an isobutoxy group or a t-butoxy group is preferable, and a methoxy group is more preferably a methoxy group. desirable.

Examples of the silyl group and the amino group represented by the substituent Z include the same silyl group and amino group as 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.

An organic electroluminescent device of the present invention is an organic electroluminescent device having a pair of electrodes composed of an anode and a cathode and a light emitting layer between the electrodes and having at least one organic layer between the light emitting layer and the cathode, ,

And at least one compound represented by the general formula (1) is contained in the light emitting layer,

And 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.

(11)

(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. However, R ₁ does not represent a carbazolyl group or a perfluoroalkyl group. when R ₁ is a plurality is present, a plurality of R ₁ is, each may be the same or different; a plurality of R ₁ is in addition, the aryl ring may be formed which may have the substituents Z bonded to each other.

R ₂ to R ₅ Each independently represent an alkyl group, an aryl group, a silyl group, a cyano group or a fluorine atom, and may further have a substituent Z. R ₂ to R ₅ A plurality of R < _{2 >} to a plurality of R < ₅ > May be the same or different.

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 substituents Z, .

n1 represents an integer of 0 to 5;

and n2 to n5 each independently represents an integer of 0 to 4.)

The alkyl group represented by R ₁ may have a substituent. As the substituent in the case of having a substituent, the above-mentioned substituent Z can be mentioned, and the substituent Z is preferably a fluorine atom. Provided that the alkyl group represented by R < ₁ &_gt; is not 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, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec- Methylbutyl, 3-methylpentyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl, 1,1-dimethylbutyl , A 1,2-dimethylbutyl group, a 1,3-dimethylbutyl group and a 2,3-dimethylbutyl group. Of these, a methyl 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 more preferable.

The aryl group represented by R ₁ may be an axial ring or may have a substituent. As the substituent in the case of having a substituent, the above-mentioned substituent Z can be mentioned, and as the substituent Z, an alkyl group, an aryl group, a fluorine atom or a cyano group which may be substituted with a fluorine atom is preferable, and an alkyl group is more preferable. The aryl group represented by R ₁ is preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 18 carbon atoms. The aryl group having 6 to 18 carbon atoms is preferably an aryl group having 6 to 18 carbon atoms which may have an alkyl group, a fluorine atom or a cyano group which may be substituted with a fluorine atom having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms Or an aryl group having 6 to 18 carbon atoms which may have an alkyl group of 1 to 18 carbon atoms. For example, a phenyl group, a dimethylphenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a methylnaphthyl group, a t-butylnaphthyl group, an anthranyl group, a phenanthryl group, a klycenyl group, a cyanophenyl group, a trifluoromethylphenyl group, Among them, 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, desirable.

The silyl group represented by R ₁ may have a substituent. As the substituent in the case of having a substituent, the above-mentioned substituent Z can be mentioned, and as the substituent Z, an alkyl group or a phenyl group is preferable, and a phenyl group is more preferable. The silyl group represented by R ₁ is preferably a silyl group having 0 to 18 carbon atoms, more preferably a silyl group having 3 to 18 carbon atoms. The silyl group having 3 to 18 carbon atoms is preferably an alkyl group having 1 to 6 carbon atoms or a silyl group having 3 to 18 carbon atoms substituted with a phenyl group and all three hydrogen atoms of the silyl group are substituted with an alkyl group having 1 to 6 carbon atoms and a More preferably substituted with any one of them, and more preferably substituted with a phenyl group. Examples thereof include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a diethylisopropylsilyl group, a dimethylphenylsilyl group, a diphenylmethylsilyl group, and a triphenylsilyl group. , A trimethylsilyl group, a dimethylphenylsilyl group or a triphenylsilyl group is preferable, and a triphenylsilyl group is more preferable.

If R ₁ is present a plurality, and the plurality of R ₁ may be the same or different in each occurrence. The plurality of R ₁ may combine with each other to form an aryl ring which may have the substituent Z described above. As the substituent Z, an alkyl group or an aryl group is preferable, and an alkyl group is more preferable.

An aryl ring with a plurality of R ₁ which is formed by binding to each other, including the plurality of the carbon atom to which R ₁ is substituted, preferably an aryl ring having 6 to 30 carbon atoms, more preferably an aryl having 6 to 14 It is a ring. The ring to be formed is preferably a benzene ring, a naphthalene ring or a phenanthrene ring, more preferably a benzene ring or a phenanthrene ring, further preferably a benzene ring. Further, the ring formed by a plurality of R ₁ may be the plurality is present, for example, a plurality of R ₁ are each bonded to form a two benzene rings to each other, together with the benzene ring to which the two substituted plurality of R ₁ , A phenanthrene ring may be formed.

R ₁ is preferably an alkyl group, an aryl group which may have an alkyl group, and a silyl group substituted by an alkyl group or a phenyl group, more preferably from 1 to 6 carbon atoms, from the viewpoints 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 4 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.

Among them, 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 substituted or unsubstituted naphthyl group, a substituted or unsubstituted naphthyl group, a triphenylsilyl group, a plurality of alkyl or aryl groups, and more preferably an unsubstituted phenyl group, A biphenyl group, a naphthyl group, or a terphenyl group, more preferably an unsubstituted phenyl group, an unsubstituted biphenyl group, or an unsubstituted naphthyl group.

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 preferable 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 a perfluoroalkyl group such as a trifluoromethyl group in addition to the examples of the alkyl group represented by R ₁ . Among them, a methyl group, a trifluoromethyl group, an isopropyl group, a t-butyl group, or a neopentyl group is preferable, and a methyl group or a t-butyl group is more preferable, and a t-butyl group is more preferable.

R ₂ to R ₅ Is preferably a silyl group, a cyano group or a fluorine atom substituted with an alkyl group, an aryl group, an alkyl group or a phenyl group, more preferably from 1 to 10 carbon atoms, An alkyl group having 6 to 18 carbon atoms, an aryl group having 6 to 18 carbon atoms, an alkyl group having 1 to 6 carbon atoms, a silyl group having 3 to 18 carbon atoms substituted with a phenyl group, a cyano group, and a fluorine atom, An aryl group having 6 to 12 carbon atoms, a silyl group having 3 to 18 carbon atoms substituted with an alkyl group having 1 to 6 carbon atoms or a phenyl group, a cyano group, and a fluorine atom.

Among them, R ₂ to R ₅ Are each independently preferably a group selected from the group consisting of a methyl group, an isopropyl group, a t-butyl group, a neopentyl group, a trifluoromethyl group, a phenyl group, a dimethylphenyl group, a trimethylsilyl group, a triphenylsilyl group, a fluorine atom and a cyano group More preferably a t-butyl group, a phenyl group, a triphenylsilyl group, or a cyano group, more preferably a t-butyl group, a phenyl group, a trimethylsilyl group, a triphenylsilyl group or a cyano group. will be.

n2 to n5 are each independently preferably an integer of 0 to 2, more preferably 0 or 1. When a substituent is introduced into the carbazole skeleton, the 3-position and 6-position of the carbazole skeleton are in the reaction active position, and it is preferable to introduce a substituent at this position in view of ease of synthesis and improvement of chemical stability.

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

[Chemical Formula 12]

(In the general formula (2), R ₆ and R ₇ Each independently represent 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. R ₆ and R ₇ A plurality of R < ₆ > and a plurality of R < ₇ > May be the same or different. Also 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 a substituent Z.

n6 and n7 each independently represent an integer of 0 to 5;

R ₈ to R ₁₁ Each independently represent a hydrogen atom, an alkyl group which may have a substituent Z, an aryl group which may have an alkyl group, a silyl group which may have a substituent Z, 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 substituents Z, May be formed.

The alkyl group represented by R ₆ and R ₇ may have a substituent. As the substituent in the case of having a substituent, the above-mentioned substituent Z can be mentioned, 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, 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 represented by R ₆ and R ₇ in the aryl group which may have an alkyl group 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 preferable 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 represented by R ₆ and R ₇ in the aryl group which may have an alkyl group is preferably an aryl group having 6 to 18 carbon atoms and more preferably an aryl group having 6 to 12 carbon atoms. Among them, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group is preferable, and a phenyl group, a naphthyl group, a naphthyl group, an anthranyl group, A biphenyl group, or a terphenyl group is more preferable.

The aryl group represented by R ₆ and R ₇ , which may have an alkyl group, is preferably an unsubstituted aryl group.

Examples of the aryl group which may have an alkyl group represented by R ₆ and R ₇ include a phenyl group, a dimethylphenyl group, a t-butylphenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a methylnaphthyl group, An anthranyl group, a phenanthryl group, and a chrysenyl group, and a phenyl group, a t-butylphenyl group, or a biphenyl group is preferable, and a phenyl group is more preferable.

R ₆ and R ₇ A plurality of R < ₆ > and a plurality of R < ₇ > May be the same or different. Also a plurality of R ₆ and a plurality of R ₇ May combine with each other to form an aryl ring which may have the substituent Z described above. As the substituent Z, an alkyl group or an aryl group is preferable, and an alkyl group is more preferable.

A plurality of R ₆ and a plurality of R ₇ , The aryl ring formed by combining with each other includes a carbon atom substituted for each of the plurality of R ₆ and the plurality of R ₇ s, and is preferably an aryl ring having 6 to 30 carbon atoms, An aryl ring having 6 to 14 carbon atoms, more preferably 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 a benzene ring, a naphthalene ring or a phenanthrene ring which may have an alkyl group having 1 to 4 carbon atoms, more preferably a benzene ring which may have an alkyl group having 1 to 4 carbon atoms, For example, a benzene ring, a benzene ring substituted with a t-butyl group, and the like. Further, a plurality of rings formed by a plurality of R ₆ or a plurality of R ₇ may be present, and for example, a plurality of R ₆ or a plurality of R ₇ Are bonded to each other to form two benzene rings, and the plurality of R ₆ or the plurality of R ₇ Together with the substituted benzene ring, may form a phenanthrene ring.

R ₆ and R ₇ Is preferably an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 18 carbon atoms which may have an alkyl group having 1 to 6 carbon atoms, a cyano group, or a fluorine atom, from the viewpoints of charge transport ability and stability against electric charges , More preferably an alkyl group having 1 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, a cyano group and a fluorine atom. In view of the stability of the charge transport ability and charge, R ₆ and R ₇ Each independently represent an alkyl group or an aryl group which may have an alkyl group.

Among them, R ₆ and R ₇ Each independently represent a phenyl group, a biphenyl group, a cyano group, a fluorine atom, and a plurality of alkyl groups substituted by a methyl group, a trifluoromethyl group, a t-butyl group, an unsubstituted phenyl group, a t- An unsubstituted benzene ring formed by combining with each other or a benzene ring substituted by a t-butyl group, more preferably a methyl group, a trifluoromethyl group, an unsubstituted phenyl group, a cyano group, a fluorine atom, and a plurality of alkyl groups An unsubstituted benzene ring formed by combining with each other, or a benzene ring substituted by a t-butyl group, and most preferably 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 still more preferably 0 or 1.

The alkyl group represented by R ₈ to R ₁₁ may have a substituent. As the substituent in the case of having a substituent, the above-mentioned substituent Z can be mentioned, 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, 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 which may have 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, more preferably an alkyl group having 1 to 4 carbon atoms Or an aryl group having 6 to 12 carbon atoms which may be substituted.

Specific examples and preferable examples of the aryl group which may have an alkyl group represented by R ₈ to R ₁₁ are the same as the specific examples and preferable examples of the aryl group which may have an alkyl group represented by R ₆ and R ₇ described above .

The silyl group represented by R ₈ to R ₁₁ may have a substituent. As the substituent in the case of having a substituent, there can be mentioned the above-mentioned substituent Z, and the substituent Z is preferably an alkyl group or a phenyl group, 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, and specific examples and preferred examples of the silyl group having 3 to 18 carbon atoms represented by R ₈ to R ₁₁ are those represented by the general formula (1) Is 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 >.

R ₈ to R ₁₁ Is preferably a hydrogen atom, an alkyl group, an aryl group which may have an alkyl group, a silyl group substituted by an alkyl group or a phenyl group, a cyano group, or a fluorine atom, each of which is substituted with an alkyl group or a phenyl group, from the viewpoints of charge transport ability and charge stability. More preferably a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 18 carbon atoms which may have an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms or an alkyl group having 3 to 18 carbon atoms More preferably a hydrogen atom, an alkyl group having 1 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 aryl group having 1 to 6 carbon atoms A silyl group having 3 to 18 carbon atoms substituted with an alkyl group or a phenyl group, a cyano group, and a fluorine atom.

Among them, R ₈ to R ₁₁ Each independently preferably represents a hydrogen atom, a methyl group, an isopropyl group, a t-butyl group, a neopentyl group, a trifluoromethyl group, a phenyl group, a dimethylphenyl group, a trimethylsilyl group, a triphenylsilyl group, And more preferably a hydrogen atom, a t-butyl group, a phenyl group, a trialkylsilyl group, a triethylsilyl group, a tri A phenylsilyl group, and a cyano group.

The compound represented by the general formula (1) or (2) is most preferably composed only of 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 占 폚 or higher and 400 占 폚 or lower, more preferably 100 占 폚 or higher and 400 占 폚 or lower, still more preferably 120 占 폚 or higher and 400 占 폚 or lower Do.

When the general formula (1) or (2) has a hydrogen atom, it also includes a isotope (deuterium atom, etc.). In this case, all of the hydrogen atoms in the compound may be substituted with isotopes, or a mixture of compounds in which some of them are included.

Specific examples of the compounds represented by the general formula (1) or (2) are illustrated below, but the present invention is not limited thereto.

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

The compound exemplified as the compound represented by the general formula (1) or (2) can be synthesized by referring to the pamphlet of International Publication No. 2004/074399. For example, the compound (A-1) can be synthesized by the method described in International Patent Publication No. 2004/074399, page 52, line 22 to page 54, line 15.

In the present invention, the compound represented by the general formula (1) or (2) is contained in the luminescent layer, but its use is not limited, and may be further contained in any layer in the organic layer. Examples of the introduction layer of the compound represented by the general formula (1) or (2) include a light emitting layer, a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron injecting layer, an exciton blocking layer and a charge blocking layer.

The compound represented by the general formula (1) or (2) is preferably contained in an amount of 50 to 99.9 mass%, more preferably 50 to 99 mass%, and more preferably 60 to 98 mass% More preferable. When the compound represented by the general formula (1) or (2) is further contained in a layer other than the light-emitting layer, the compound is preferably contained in an amount of 70 to 100 mass%, more preferably 85 to 100 mass% Is more preferable.

[Compound represented by the formula (E-1)] [

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

[Chemical Formula 16]

(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. However, R _E1 and R _E2 Is not a hydrogen atom at the same time.

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 the other layer.

In the device of the present invention, it was found that the reduction in efficiency at the time of high-luminance driving was suppressed. This is because the compound represented by the general formula (1) is contained in the light emitting layer and 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, And the electron affinity of the compound represented by the general formula (1) is in the optimum range, and the electron transporting property of the electron transporting layer from the low voltage is improved, so that it is possible to transport electrons in a large amount to the light emitting layer.

It was also found that the dependency of the emission chromaticity on the thickness of the electron transporting layer was suppressed in the device of the present invention. This is unpredictable from the conventional knowledge. However, the compound represented by the general formula (1) is contained in the light emitting layer and the compound represented by the general formula (E-1) is contained in the organic layer between the light emitting layer and the cathode, It is presumed that the above effect can be obtained because electrons are sufficiently contained and the light emission distribution is diffused.

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.

R _E1 and R _E2 The aliphatic hydrocarbon group is preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms, more preferably an alkyl group (preferably having 1 to 10 carbon atoms, such as a methyl group, an ethyl group, an isopropyl group, a t-butyl group , an alkenyl group (preferably having a carbon number of 2 to 10, more preferably a carbon number of 2 to 10), an alkenyl group (preferably an alkenyl group having 1 to 10 carbon atoms, For example, 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 More preferably an alkyl group, and particularly preferably a methyl group, an ethyl group, an isopropyl group, a t-butyl group, or a cyclohexyl group.

R _E1 and R _E2 Is 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 phenyl, naphthyl, biphenyl, anthryl, terphenyl, fluorenyl, phenanthryl, pyrenyl, and triphenylenyl. A biphenyl group, an anthryl group, or a terphenyl group is preferable, and a phenyl group, a naphthyl group, a biphenyl group, or an anthryl group is more preferable, and a naphthyl group is most preferable. The reason why the naphthyl group is preferable is considered to be that it can produce a proper interaction between molecules, whereby a low 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 above-mentioned substituent group A, preferably an alkyl group (preferably an alkyl group having 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms An ethyl group, an isopropyl group, an isobutyl group, a t-butyl group, an n-butyl group and a cyclopropyl group. Examples of the alkyl group include a methyl group, (Preferably 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 such as a phenyl group, a biphenyl group, a fluorenyl group (Preferably a fluorine atom), a cyano group, an alkoxy group, or an aromatic heterocyclic group (preferably having a carbon number of 4 to 12, more preferably a carbon number of 4 to 12), a naphthyl group, Aromatic hetero Rigi is, for example, there may be mentioned such as a pyridyl group, a furyl group, a thienyl group, it is more groups pyridyl. A).

R _E1 and R _E2 Is a substituted or unsubstituted aromatic heterocyclic group, the aromatic heterocyclic group is preferably an aromatic heterocyclic group having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably an aromatic heterocyclic group having 2 to 12 carbon atoms to be. Examples of the aromatic heterocyclic group include an azole group, a diazo 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 diazo group and a pyridyl group are preferable And a pyridyl group is more preferable.

When the aromatic heterocyclic group has a substituent, examples of the substituent include R _E1 and R _E2 Is the same as the specific examples and preferable range of the substituent which may be taken in the case of an aryl group.

R _E1 and R _E2 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. R _E1 and R _E2 Is an aryl group, the specific examples and preferred ranges thereof are the same as described above.

R _E1 and R _E2 May be the same or different from each other, and the same is preferable from the viewpoint of synthesis. However, R _E1 and R _E2 Is not a hydrogen atom at the same time.

In the 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 and a triphenylenylene group , A phenylene group, a naphthylene group, a biphenylene group, or an anthrylene group is preferable, a phenylene group and a naphthylene group are more preferable, and a phenylene group is most preferable.

When the arylene group has a substituent, examples of the substituent include R _E1 and R _E2 Is the same as the specific examples and preferable range of the substituent which may be taken in the case of 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 2 to 12 carbon atoms ≪ / RTI > bivalent aromatic heterocyclic group. The divalent aromatic heterocyclic group includes, for example, a divalent aryl group, a divalent diazo group, a divalent triazole group, a divalent oxazole group, a divalent thiazole group, a divalent pyridyl group, a divalent furyl group, A thienyl group and the like. A divalent alkoxyl group, a divalent diazo group and a divalent pyridyl group are preferable, and a divalent pyridyl group (pyridyl group) is more preferable.

When the divalent aromatic heterocyclic group has a substituent, examples of the substituent include R _E1 and R _E2 Is the same as the specific examples and preferable range of the substituent which may be taken in the case of an aryl group.

Ar is preferably a substituted or unsubstituted arylene group, and more preferably an unsubstituted arylene group. Specific examples and preferable ranges of the case where Ar is an arylene group are as described above.

In the 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.

R _E3 The aliphatic hydrocarbon group is preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms, more preferably an alkyl group (preferably having 1 to 10 carbon atoms, such as a methyl group, an ethyl group, an isopropyl group, a t-butyl group, (Preferably having 2 to 10 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, (Preferably having 2 to 10 carbon atoms, such as propargyl, 3-pentynyl, etc.), or an alkynyl group , More preferably an alkyl group, and particularly preferably a methyl group, an ethyl group, an isopropyl group, a t-butyl group, or a cyclohexyl group.

R _E3 When the aryl group is 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 phenyl, naphthyl, biphenyl, anthryl, terphenyl, fluorenyl, phenanthryl, pyrenyl, and triphenylenyl. A biphenyl group, or 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 above-mentioned substituent group A, preferably an alkyl group (preferably an alkyl group having 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms An ethyl group, an isopropyl group, an isobutyl group, a t-butyl group, an n-butyl group and a cyclopropyl group. Examples of the alkyl group include a methyl group, (Preferably 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 such as a phenyl group, a biphenyl group, a fluorenyl group (Preferably a fluorine atom), a cyano group, an alkoxy group, or an aromatic heterocyclic group (preferably having 2 to 12 carbon atoms, more preferably 2 to 12 carbon atoms) Aromatic hetero And examples thereof include an azole group, a diazo 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 diazo group and a pyridyl group are preferable, Is a benzimidazolyl group).

These substituents may further have a substituent, if possible. The additional substituent may be a substituent selected from the above-mentioned substituent group A, preferably an alkyl group, an aryl group or an aromatic heterocyclic group, Examples and preferred ranges include the above R _E3 Is the same as the specific examples and preferable range of the substituent when the substituted aryl group is represented.

R _E3 The substituent may be bonded to each other to form a ring. Examples of the ring include an aliphatic hydrocarbon ring, an aromatic ring and an aromatic heterocyclic ring. An aromatic ring is preferable, and a benzene ring, An anthracene ring, a naphthyl ring, or a ring having a structure composed of a combination of these rings, and a ring of a structure formed by a fluorene ring, an anthracene ring, or a combination thereof is preferable.

R _E3 When the substituted or unsubstituted aromatic heterocyclic group is the substituted or unsubstituted aromatic heterocyclic group, the aromatic heterocyclic group is preferably an aromatic heterocyclic group having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 12 carbon atoms to be. Examples of the aromatic heterocyclic group include an azole group, a diazo 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 diazo group and a pyridyl group are preferable And particularly preferably a benzoimidazolyl group.

When the aromatic heterocyclic group has a substituent, examples of the substituent include substituents selected from the above-mentioned 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 8 carbon atoms, An isopropyl group, an isobutyl group, a t-butyl group, an n-butyl group and a cyclopropyl group. Examples of the alkyl group include methyl, ethyl, isobutyl An aryl group (preferably an aryl group having 6 to 18 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, such as a phenyl group, a biphenyl group, a fluorine group, or a t-butyl group) (Preferably a fluorine atom), a cyano group, an alkoxy group, or an aromatic heterocyclic group (for example, a phenyl group, a naphthyl group and the like, preferably a phenyl group or a biphenyl group, wind Preferably an aromatic heterocyclic group having 2 to 12 carbon atoms, and examples thereof include a pyridyl group, a furyl group, and a thienyl group, and a pyridyl group is more preferable). Among them, an aryl group is particularly preferable.

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

In the 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.

R _E4 (Preferably having 1 to 10 carbon atoms, for example, a methyl group, an ethyl group, an isopropyl group, a t-butyl group, a n-butyl group, or a n-propyl group), the aliphatic hydrocarbon group preferably has 1 to 12 carbon atoms, An alkenyl group (preferably having 2 to 10 carbon atoms such as vinyl, allyl, n-propyl, isopropyl, n-butyl, 2-butenyl, 3-pentenyl and the like) or an alkynyl group (preferably having 2 to 10 carbon atoms, such as propargyl and 3-pentynyl) More preferably an alkyl group, and particularly preferably a methyl group, an ethyl group, an isopropyl group, a t-butyl group or a cyclohexyl group.

R _E4 Is 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 phenyl, naphthyl, biphenyl, anthryl, terphenyl, fluorenyl, phenanthryl, pyrenyl, and triphenylenyl. A biphenyl group, or an anthryl group is preferable, a phenyl group or a naphthyl group is more preferable, and a phenyl group is more preferable.

When the aryl group has a substituent, examples of the substituent include R _E1 and R _E2 Is the same as the specific examples and preferable range of the substituent which may be taken in the case of an aryl group.

R _E4 Is a substituted or unsubstituted aromatic heterocyclic group, the aromatic heterocyclic group is preferably an aromatic heterocyclic group having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably an aromatic heterocyclic group having 2 to 12 carbon atoms to be. Examples of the aromatic heterocyclic group include an azole group, a diazo 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 diazo group and a pyridyl group are preferable And a pyridyl group is more preferable.

When the aromatic heterocyclic group has a substituent, examples of the substituent include R _E1 and R _E2 Is the same as the specific examples and preferable range of the substituent which may be taken in the case of an aryl group.

R _E4 Is preferably a substituted or unsubstituted aryl group, more preferably an unsubstituted aryl group, from the viewpoint of obtaining an appropriate interaction between molecules. R _E4 Is an aryl group, the specific examples and preferred ranges thereof are the same as described above.

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

[Chemical Formula 17]

(In the formulas (E-2) and (E-3), 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 Is not a hydrogen atom at the same time.

R _E3 Represents a hydrogen atom, an aliphatic hydrocarbon, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group.

In the general formulas (E-2) and (E-3), R _E1 , R _E2 , and R _E3 R _E1 , R _E2 and R _{E3 in the} general formula (E-1) And the preferred range is the same.

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

[Chemical Formula 18]

[Chemical Formula 19]

[Chemical Formula 20]

[Chemical Formula 21]

(E-1) to (e-10) are more preferable, and (e-1) to (e-4) and (e- (e-3), (e-4) and (e-8) are particularly preferable.

The compound represented by the general formula (E-1) can be synthesized by the method described in Patent Publication No. 4308663. [

After the synthesis, it is preferable to carry out purification by column chromatography, recrystallization and the like, and then purify by sublimation purification. By the sublimation purification, it is possible not only to separate organic impurities, but also to effectively remove inorganic salts and residual solvents.

In the light-emitting element 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, and its use is not limited. do. As the introduction layer of the compound represented by the general formula (E-1) related to the present invention, any one of the light-emitting layer, the hole injection layer, the hole transport layer, the electron transport layer, the electron injection layer, the exciton block layer, can do.

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, more preferably an electron transporting layer.

[Organic electroluminescent device]

The device of the present invention will be described in detail.

The organic electroluminescent device of the present invention is an organic electroluminescent device having a pair of electrodes composed of an anode and a cathode and a light emitting layer between the electrodes and having at least one organic layer between the light emitting layer and the cathode on the substrate, At least one compound represented by the above general formula (1) and at least one organic layer between the light emitting layer and the cathode contains at least one compound represented by the above general formula (E-1).

In the organic electroluminescent device 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, and may further include an organic layer.

It is preferable that at least one of the anode and the cathode is transparent or semitransparent in nature of the light emitting element.

Fig. 1 shows an example of the structure of an organic electroluminescent device related to the present invention.

The organic electroluminescent device 10 according to the present invention shown in Fig. 1 has a light emitting layer 6 sandwiched between a positive electrode 3 and a negative electrode 9 on a support substrate 2. Specifically, a hole injecting layer 4, a hole transporting layer 5, a light emitting layer 6, a hole blocking layer 7, and an electron transporting layer 8 are formed in this order between the anode 3 and the cathode 9 Respectively.

≪ Configuration of organic layer &

The layer structure of the organic layer is not particularly limited and may be appropriately selected depending on the application and purpose of the organic electroluminescent device, and is preferably formed on the transparent electrode or on the back electrode. In this case, the organic layer is formed on the entire surface or one surface of the transparent electrode or the back electrode.

The shape, size, and thickness of the organic layer are not particularly limited and may be appropriately selected according to the purpose.

Specific layer configurations are as follows, but the present invention is not limited to these configurations.

· Anode / hole transporting layer / light emitting layer / electron transporting layer / cathode

· Anode / hole transporting layer / light emitting layer / block layer / electron transporting layer / cathode

Anode / hole transporting layer / light emitting layer / block layer / electron transporting layer / electron injection layer / cathode

Anode / hole injecting layer / hole transporting layer / light emitting layer / electron transporting layer / electron injecting layer / cathode

· Anode / hole injecting layer / hole transporting layer / light emitting layer / block layer / electron transporting layer / cathode

Anode / hole injection layer / hole transporting layer / light emitting layer / block layer / electron transporting layer / electron injection layer / cathode

The structure of the organic electroluminescent device, the substrate, the cathode and the anode are described in detail in, for example, Japanese Patent Application Laid-Open No. 2008-270736, and the matters described in the publication can be applied to the present invention.

<Substrate>

The substrate used in the present invention is preferably a substrate that does not scatter or attenuate light generated in 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 processability.

<Anode>

The anode usually has a function as an electrode for supplying holes to the organic layer, and the shape, structure, size, and the like of the anode are not particularly limited and can be appropriately selected from known electrode materials depending on the use and purpose of the light-emitting element . As described above, the anode is usually provided as a transparent anode.

<Cathode>

The shape of the cathode is not particularly limited as long as it has a function as an electrode for injecting electrons into the organic layer. The shape, structure, size, etc. of the cathode are suitably selected from known electrode materials depending on the use and purpose of the light- .

As for the substrate, the positive electrode and the negative electrode, the matters described in paragraphs [0070] to [0089] of Japanese Laid-Open Patent Application No. 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 electroluminescent device of the present invention, each organic layer is preferably formed by any one of a solution film forming process such as a dry film forming method such as a vapor deposition method and a sputtering method, a transfer method, a printing method, a spin coat method, and a bar coat method . In the device of the present invention, it is preferable that at least one of a light emitting layer, an organic layer between the light emitting layer and the cathode, and another organic layer existing between the anode and the cathode is formed by a solution coating process.

[Light Emitting Layer]

The light emitting layer is a layer having a function of accepting holes from an anode, a hole injecting layer, or a hole transporting layer when receiving an electric field, receiving electrons from a cathode, an electron injecting layer, or an electron transporting layer and providing a field for recombination of holes and electrons to emit light to be.

The substrate, the anode, the cathode, the organic layer, and the light-emitting layer are described in detail in, for example, JP-A-2008-270736 and JP-A-2007-266458, and the matters described in these publications can be applied to the present invention . The light emitting layer may contain a material which does not have charge transportability and does not emit light.

(Luminescent material)

As the light-emitting material in the present invention, any of a phosphorescent light-emitting material and a fluorescent light-emitting material can be used.

The light emitting layer in the present invention may contain two or more kinds of light emitting materials in order to improve color purity or to widen the light emitting wavelength range. At least one of the light emitting materials is preferably a phosphorescent material.

The light emitting material in the present invention preferably satisfies the relationship of 1.2 eV> ΔIp> 0.2 eV and / or 1.2 eV> ΔEa> 0.2 eV with respect to the host material in view of drive durability Do. Here,? Ip represents the difference between the Ip values of the host material and the light emitting material, and? Ea represents the difference between the host material and the Ea value of 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 material and the phosphorescent material are described in, for example, paragraphs [0100] to [0164] of JP-A No. 2008-270736 and paragraphs [0088] to [0090] of JP-A No. 2007-266458 And the matters described in these publications can be applied to the present invention.

From the viewpoint of light emission efficiency and the like, a phosphorescent material is preferable. Examples of the phosphorescent material which can be used in the present invention include those described in US 6303238B1, US6097147, WO00 / 57676, WO00 / 70655, WO01 / 08230, WO01 / 39234A2, WO01 / 41512A1, WO02 / 02714A2, WO02 / 15645A1, WO02 / 44189A1 , WO05 / 19373A2, JP-A-2001-247859, JP-A-2002-302671, JP-A-2002-117978, JP-A-2003-133074, JP-A-2002-235076, JP- -123982, JP-A-2002-170684, EP1211257, JP-A-2002-226495, JP-A-2002-234894, JP-A-2001-247859, JP-A-2001-298470, JP- -173674, JP-A-2002-203678, JP-A-2002-203679, JP-A-2004-357791, JP-A 2006-256999, JP-A 2007-19462, JP-A 2007-84635 , Japanese Unexamined Patent Application Publication No. 2007-96259, etc. Among them, preferred examples of the luminescent dopant include Ir complex, Pt complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu complex, Tb complex , Gd complexes, Dy complexes, and Ce complexes. Particularly preferred are Ir complexes, Pt complexes or Re complexes, among which Ir complexes containing at least one of a metal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond and a metal- Complex, or a Re complex is preferable. From the viewpoints of luminous efficiency, drive durability and chromaticity, Ir complexes and Pt complexes are particularly preferable, and Ir complexes are most preferable.

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

[Chemical Formula 22]

(Wherein Q ¹ , Q ² , Q ³ and Q ⁴ Independently represent a ligand coordinated to Pt. L ¹ , L ² and L ³ Each independently represent a single bond or a divalent linking group.

The general formula (C-1) will be described. Q ¹ , Q ² , Q ³ and Q ⁴ Independently represent a ligand coordinated to Pt. At this time, Q ¹ , Q ² , Q ³ and Q ⁴ And Pt may be covalent bond, ionic bond, coordination bond, or the like. Q ¹ , Q ² , Q ³ and Q ⁴ Q ¹ , Q ² , Q ³ and Q ⁴ are preferably a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom and a phosphorus atom, , At least one of the atoms bonding to Pt in Pt is preferably a carbon atom, more preferably two carbon atoms, and particularly preferably two carbon atoms and two nitrogen atoms.

As Q ¹ , Q ² , Q ³ and Q ⁴ bonded to Pt by a carbon atom, an anionic ligand or a neutral ligand may be used. As an anionic ligand, a vinyl ligand, an aromatic hydrocarbon ring ligand (for example, a benzene ligand, naphthalene A thiophene ligand, a pyridine ligand, a pyrazine ligand, a pyrimidine ligand, a pyridazine ligand, a triazine ligand, a thiazole ligand, an oxazole ligand, an imidazole ligand, an anthracene ligand, a phenanthrene ligand, , Pyrrole ligands, imidazole ligands, pyrazole ligands, triazole ligands, and cyclic rings containing them (e.g., quinoline ligands, benzothiazole ligands, etc.). The neutral ligand is a carbenic ligand.

Q ¹ , Q ² , Q ³ and Q ⁴ bonded to the nitrogen atom Pt may be a neutral ligand or an anionic ligand. As the neutral ligand, a nitrogen-containing aromatic heterocyclic ligand (pyridine ligand, pyrazine ligand, pyrimidine ligand , Pyrazine ligands, triazine ligands, imidazole ligands, pyrazole ligands, triazole ligands, oxazole ligands, thiazole ligands, and cyclic rings including them (for example, quinoline ligands, benzimidazole ligands, etc.) Amine ligands, nitrile ligands, and immune ligands. Examples of the anion ligand include amino ligands, imino ligands, nitrogen nitrogen aromatic heterocyclic ligands (pyrrole ligands, imidazole ligands, triazole ligands, and cyclic rings containing them (for example, indole ligands, benzimidazole ligands, etc.) ).

Q ¹ , Q ² , Q ³ and Q ⁴ bonded to Pt as an oxygen atom may be a neutral ligand or an anionic ligand. Examples of the neutral ligand include an ether ligand, a ketone ligand, an ester ligand, an amide ligand, Ligands (furan ligands, oxazole ligands, and cyclic rings containing them (benzooxazole ligands, etc.)). Examples of the anion 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 the sulfur atom Pt may be a neutral ligand or an anionic ligand. Examples of the neutral ligand include a thioether ligand, a thioketone ligand, a thioester ligand, a thioamide ligand, A sulfo heterocyclic ligand (a thiophene ligand, a thiazole ligand, and a cyclic ring compound including them (benzothiazole ligand, etc.)). Examples of an anionic ligand include an alkyl mercapto ligand, an aryl mercapto ligand, a heteroaryl mercapto ligand, and the like.

Q ¹ , Q ² , Q ³ and Q ⁴ bonded to the phosphorus atom Pt may be a neutral ligand or an anionic ligand. Examples of the neutral ligand include a phosphine ligand, a phosphate ester ligand, a phosphorous ester ligand, (Phosphine ligand, etc.). Examples of the anionic ligand include a phosphino ligand, a phosphinyl ligand, a phosphoryl ligand, and the like.

The group represented by Q ¹ , Q ² , Q ³ and Q ⁴ may have a substituent, and the substituent group as the above substituent group A can be suitably used. And the substituents may be connected to each other (Q ³ and Q ⁴ Is connected, it becomes a Pt complex of a cyclic quadrivalent ligand).

As the group represented by Q ¹ , Q ² , Q ³ and Q ⁴ , an aromatic hydrocarbon ring ligand which is bonded to Pt by a carbon atom, an aromatic heterocyclic ligand which is bonded to Pt by a carbon atom, a nitrogen heteroaromatic ligand which binds to Pt by a nitrogen atom A heteroaryloxy ligand, a silyloxy ligand, more preferably an aromatic hydrocarbon ring ligand which is bonded to Pt by a carbon atom, an aromatic heterocyclic ring which is bonded to Pt by a carbon atom, a heteroaryloxy ligand, an acyloxy ligand, an alkyloxy ligand, an aryloxy ligand, a heteroaryloxy ligand, A nitrogen-containing aromatic heterocyclic ligand, an acyloxy ligand, an aryloxy ligand which is bonded to the nitrogen atom Pt, more preferably an aromatic hydrocarbon ring ligand which binds to Pt by a carbon atom, an aromatic heterocyclic ligand which binds to Pt by a carbon atom, A nitrogen-containing aromatic group bonded to Pt through a nitrogen atom Interrogating ring ligand, an acyloxy ligand.

L ¹ , L ² and L ³ Represents a single bond or a divalent linking group. Examples of the divalent linking group represented by L ¹ , L ² and L ³ include an alkylene group (methylene, ethylene, propylene), an arylene group (phenylene, naphthalenediyl), a heteroarylene group (pyridinediyl, (-NR-) (phenylimino group, etc.), an oxy group (-O-), a thio group (-S-), a phosphinoid group (-PR-) (phenylphosphinylidene group etc.), a silylene group (-SiRR '-) (dimethyl silylene group, diphenyl silylene group, etc.), or a combination thereof. Here, examples of R and R 'include, independently of each other, an alkyl group, an aryl group and the like. These linking groups may further have a substituent.

As L ¹ , L ² and L ³ , a monovalent bond, an alkylene group, an arylene group, a heteroarylene group, an imino group, an oxy group, a thio group and a silylene group are preferable as L ¹ , L ² and L ³ from the viewpoints of the stability of the complex and the yield of light- More preferably a single bond, an alkylene group or an arylene group, more preferably a single bond, a methylene group or a phenylene group, more preferably a single bond, an alkylene group, an arylene group or an imino group, , And a disubstituted methylene group, and more preferably a single bond, a dimethylmethylene group, a diethylmethylene group, a diisobutylmethylene group, a dibenzylmethylene group, an ethylmethylmethylene group, a methylpropylmethylene group, an isobutylmethylmethylene group , A diphenylmethylene group, a methylphenylmethylene group, a cyclohexanediyl group, a cyclopentanediyl 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.

Among the platinum complexes represented by the general formula (C-1), platinum complexes represented by the following general formula (C-2) are more preferable.

(23)

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

The general formula (C-2) will be described. L ²¹ is synonymous with L ¹ in the general formula (C-1), and the preferable range thereof is also the same.

A ²¹ and A ²² each independently represent a carbon atom or a nitrogen atom. At least one of A ²¹ and A ²² is preferably a carbon atom, and all of A ²¹ and A ²² are carbon atoms from the viewpoints of the stability of the complex and the yield of light emission of the complex.

Z ²¹ and Z ²² each independently represent a nitrogen-containing aromatic heterocyclic ring. Examples of the nitrogen-containing heteroaromatic ring represented by Z ²¹ and Z ²² include pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadiazole A thiadiazole ring, and the like. The ring represented by Z ²¹ and Z ²² is preferably a pyridine ring, a pyrazine ring, an imidazole ring, or a pyrazole ring in view of the stability of the complex, the control of the emission wavelength, and the quantum yield of light emission. More preferably, 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 heterocyclic ring represented by Z ²¹ and Z ²² may have a substituent. As the substituent on the carbon atom, the above-mentioned substituent group A and the substituent on the nitrogen atom, the above-mentioned 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 suitably selected for the control of the emission wavelength or the electric potential. In the case of shortening the wavelength, the electron donating group, the fluorine atom and the aromatic ring group are preferable. Examples thereof include an alkyl group, a dialkylamino group, an alkoxy group, a fluorine atom, A heterocyclic group and the like are selected. In the case of long wavelengths, an electron attracting 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 from the viewpoint of stability of the complex, an alkyl group or an aryl group is preferable. The substituents may be connected to each other to form a condensed ring. Examples of the ring to be formed include benzene ring, pyridine ring, pyrazine ring, pyridazine ring, pyrimidine ring, imidazole ring, oxazole ring, thiazole ring, , Thiophene ring, furan ring and the like.

Z ²³ , Z ²⁴ Each independently represent a benzene ring or an aromatic heterocyclic ring. Examples of the nitrogen-containing heteroaromatic ring represented by Z ²³ and Z ²⁴ include a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, an imidazole ring, a pyrazole ring, an oxazole ring, a thiazole ring, A ring, an oxadiazole ring, a thiadiazole ring, a thiophene ring, a furan ring, and the like. 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 in view of stability of a complex, control of an emission wavelength, Preferably a benzene ring, a pyridine ring or a pyrazole ring, more preferably a benzene ring or a pyridine ring.

The benzene ring and nitrogen-containing aromatic heterocyclic ring represented by Z ²³ and Z ²⁴ may have a substituent. As the substituent on the carbon atom, the above-mentioned substituent group A may be used. As the substituent on the nitrogen atom, the above-mentioned substituent group B may be applied. The substituent on the carbon is preferably an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group or a fluorine atom. The substituent is suitably selected for control of the emission wavelength or the electric potential. In the case of long wavelength conversion, the electron donating group and the aromatic ring group are preferable. For example, an alkyl group, a dialkylamino group, an alkoxy group, an aryl group, an aromatic heterocyclic group, do. In the case of shortening the wavelength, an electron-attracting 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 from the viewpoint of stability of the complex, an alkyl group or an aryl group is preferable. The substituents may be connected to each other to form a condensed ring. Examples of the ring to be formed include benzene ring, pyridine ring, pyrazine ring, pyridazine ring, pyrimidine ring, imidazole ring, oxazole ring, thiazole ring, , Thiophene ring, furan ring and the like.

Among 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).

&Lt; EMI ID =

(In the formula (C-4), A ⁴⁰¹ to A ⁴¹⁴ each independently represent a CR or a nitrogen atom, R represents a hydrogen atom or a substituent, and L ⁴¹ represents a single bond or a divalent linking group.

The general formula (C-4) will be described.

A ⁴⁰¹ to A ⁴¹⁴ each independently represent a CR or a nitrogen atom. R represents a hydrogen atom or a substituent.

As the substituent represented by R, the substituent group A described above can be applied.

A ⁴⁰¹ to A ⁴⁰⁶ are preferably CR and R may be connected to each other to form a ring. When A ⁴⁰¹ to A ⁴⁰⁶ are CR, R of 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, A hydrogen atom, an amino group, an alkoxy group, an aryloxy group and a fluorine atom, particularly preferably a hydrogen atom or a fluorine atom. The R of 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, An alkoxy group, an aryloxy group, a fluorine atom, and particularly preferably a hydrogen atom.

L ⁴¹ is synonymous with L ¹ in the general formula (C-1), and the preferable range thereof is also the same.

As A ⁴⁰⁷ to A ⁴¹⁴ , the number of N (nitrogen atom) is preferably 0 to 2, more preferably 0 to 1, in each of A ⁴⁰⁷ to A ⁴¹⁰ and A ⁴¹¹ to A ⁴¹⁴ . When shifting the emission wavelength of the short wavelength side, A ⁴⁰⁸ and A ⁴¹² of which is preferably a nitrogen atom, the A ⁴⁰⁸ and A ⁴¹² are both more preferably a nitrogen atom.

When A ⁴⁰⁷ to A ⁴¹⁴ represent CR, R of 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, 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. The 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, A perfluoroalkyl group, a fluorine atom and a cyano group, and particularly preferably a hydrogen atom, a phenyl group or a fluorine atom. R of 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, R may be connected to each other to form a ring.

Among the platinum complexes represented by the general formula (C-2), one more preferred embodiment is a platinum complex represented by the following general formula (C-5).

(25)

(In the general formula (C-5), A ⁵⁰¹ to A ⁵¹² each independently represent a CR or a nitrogen atom, R represents a hydrogen atom or a substituent, and L ⁵¹ represents a single bond or a divalent linking group.

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

A ⁵⁰⁷ , A ⁵⁰⁸ and A ⁵⁰⁹ and A ⁵¹⁰ , A ⁵¹¹ and A ⁵¹² , and each independently represent a CR or nitrogen atom. R represents a hydrogen atom or a substituent. As the substituent represented by R, the substituent group A described above 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, a dialkylamino group, More preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, a dialkylamino group, a cyano group, a fluorine atom, more preferably a hydrogen atom , An alkyl group, a trifluoromethyl group, and a fluorine atom. When possible, substituents may be connected to each other to form a 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, more preferably A ⁵¹⁰ or A ⁵⁰⁷ is a nitrogen atom.

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

(26)

(Wherein 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 each independently represent a benzene ring or an aromatic heterocyclic ring. Y is an anionic non-ligand ligand which binds to Pt.)

The general formula (C-6) will be described. L ⁶¹ is synonymous with L ¹ in the general formula (C-1), and the preferable range is also the same.

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

Z ⁶¹ , Z ⁶² Are respectively represented by Z ²¹ and Z ^{22 in the} above general formula (C-2) And the preferred scope is the same. Z ⁶³ is synonymous with Z ²³ in the general formula (C-2), and the preferable range thereof is also the same.

Y is an anionic acyclic ligand which binds to Pt. The non-recrystallizable ligand means that the atoms bonded to Pt do not form a ring in the state of a ligand. The atom bonded to Pt in Y is preferably a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, more preferably a nitrogen atom or an oxygen atom, and most preferably an oxygen atom.

As Y bonded to Pt through a carbon atom, a vinyl ligand can be mentioned. As Y bonded to the nitrogen atom Pt, an amino ligand or an imino ligand can be exemplified. Examples of Y bonded to Pt through an oxygen atom include an alkoxy ligand, an aryloxy ligand, a heteroaryloxy ligand, an acyloxy ligand, a silyloxy ligand, a carboxyl ligand, a phosphoric acid ligand, and a sulfonic acid ligand. Examples of Y bonded to Pt in the sulfur atom include an alkyl mercapto ligand, an aryl mercapto ligand, a heteroaryl mercapto ligand, and a thiocarboxylic acid ligand.

The ligand represented by Y may have a substituent. As the substituent, the above-mentioned substituent group A may suitably be used. The substituents may be connected to each other.

The ligand represented by Y is preferably a ligand which is bonded to Pt by an oxygen atom, more preferably an acyloxy ligand, an alkyloxy ligand, an aryloxy ligand, a heteroaryloxy ligand, or a silyloxy ligand, more preferably an acyloxy ligand to be.

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

(27)

(Wherein A ⁷⁰¹ to A ⁷¹⁰ each independently represent a CR 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 a It is a non-repeating ligand of Onion.)

The general formula (C-7) will be described. L ⁷¹ is synonymous with L ⁶¹ in the above general formula (C-6), and the preferable range thereof is also the same. A ⁷⁰¹ to A ⁷¹⁰ are synonymous with A ⁴⁰¹ to A ⁴¹⁰ in the general formula (C-4), and preferable ranges are also the same. Y agrees with Y in the formula (C-6), and the preferable range thereof is also the same.

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

(28)

[Chemical Formula 29]

(30)

Platinum complex compounds represented by the general formula (C-1) can be prepared, for example, in Journal of Organic Chemistry 53, 786, (1988), G.R. Method described in Newkome et al., Page 789, left column 53 to right column 7, method 790, method described in left column 18 to 38, method 790, right column 19 to 30, Berichte 113, 2749 (1980), H. Lexy et al.), Page 2752, lines 26 to 35, and the like.

For example, the ligand or its dissociation product and a metal compound are dissolved in a solvent (for example, a halogen-based solvent, an alcohol-based solvent, an ether-based solvent, an ester-based solvent, a ketone-based solvent, a nitrile- (Various inorganic and organic bases such as sodium methoxide, t-butoxy potassium, and the like) in the presence of a base, in the presence of a solvent, in the presence of a solvent, , Triethylamine, potassium carbonate, etc.), or in the presence of a base, at room temperature or below, or by heating (a method of heating by microwave in addition to ordinary heating is also effective).

The content of the compound represented by the general formula (C-1) in the light emitting layer of the present invention is preferably 1 to 30 mass%, more preferably 3 to 25 mass%, and more preferably 5 to 20 mass% More preferable.

The iridium complex is preferably an iridium complex represented by the following formula (T-1).

[Compound represented by formula (T-1)

The compound represented by the general formula (T-1) is explained.

(31)

Wherein R _T3 ', R _T3 , R _T4 , R _T5 and R _T6 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, a tri vinyl group _{fluoro, -CO 2 R T, -C (} O) R T, -N (R T) 2, -NO 2, -OR T, represents a halogen atom, an aryl group or a heteroaryl group, the substituent further T .

E represents a carbon atom or a nitrogen atom.

Q is a 5- or 6-membered aromatic heterocyclic ring or condensed aromatic heterocyclic ring containing at least one nitrogen.

In the ring Q, a line connecting E and N is represented by one line, and may be a single bond or a double bond, regardless of the bonding species.

R _T3 , R _T4 , R _T5 and R _T6 May be bonded to each other to form a condensed 4- to 7-membered ring. The condensed 4- to 7-membered ring may be cycloalkyl, aryl or heteroaryl, and the condensed 4- to 7-membered ring may further have a substituent T. Further, the condensed 4- to 7-membered ring may be further axially linked, and the additional ring may have substituent T.

R _T3 'and R _{T6 Is, -C (R T) 2 -C} (R T) 2 -, -CR T = CR T -, -C (R T) 2 -, -O-, -NR T -, -OC (R T) ₂ -, -NR _T -C (R _T ) ₂ - and -N = CR _T -, and R _T Each independently represent 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. In addition, two R _T May be combined with each other to form a ring.

Each substituent T is independently selected from the group consisting of a fluorine atom, -R ', -OR', -N (R ') ₂ , -SR', -C (O) _{) N (R ') 2,} -CN, -NO 2, -SO 2, -SOR', -SO 2 R represents a ', or -SO ₃ R', R 'are, each independently, a hydrogen atom, an alkyl group, A perfluoroalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

(X-Y) 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 which 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 in total, more preferably an alkyl group having 1 to 6 carbon atoms in total, For example, 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 which may be substituted include the substituent T described above. 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 atoms, more preferably a cycloalkyl group having 5 to 6 total carbon atoms, For example, a cyclopentyl group, a cyclohexyl group and the like.

The alkenyl group represented by R _T3 ', R _T3 , R _T4 , R _T5 and R _T6 is preferably an alkenyl group having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, 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 and R _T6 preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, Propynyl, propynyl, 1-propynyl, 3-pentynyl and the like.

The heteroalkyl group represented by R _T3 ', R _T3 , R _T4 , R _T5 , and R _T6 includes a group in which at least one carbon of the alkyl group is substituted 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 preferably a fluorine atom.

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 an aryl group having 6 to 20 carbon atoms to be. Examples of the aryl group include phenyl, naphthyl, biphenyl, anthryl, terphenyl, fluorenyl, phenanthryl, pyrenyl, triphenylenyl, tolyl, A fluorenyl group, a naphthyl group, a biphenyl group, an anthryl group, or a terphenyl group is preferable, and a phenyl group, a fluorenyl group, and a 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 substituted or unsubstituted 5 or 6 atom And examples thereof include a pyridyl group, a pyrazinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a cinnolinyl group, A thiazolyl group, a thiazolyl group, an oxazolyl group, a benzothiazolyl group, a benzothiazolyl group, an imidazolyl group, a benzimidazolyl group, a triazolyl group, an oxazolyl group, a benzothiazolyl group, A thiazolyl group, a thiazolyl group, a benzothiazolyl group, an isothiazolyl group, a benzisothiazolyl group, a thiadiazolyl group, an isoxazolyl group, a benzisoxazolyl group, a pyrrolidinyl group, a piperidinyl group, An imidazolidinyl group, a thiazolinyl group, a sulfolanyl group, a carbazolyl group, Benzo furyl, dibenzo-thienyl group, a group turn-pyrido degrees, and the like. Preferable examples thereof include a pyridyl group, a pyrimidinyl group, an imidazolyl group and a thienyl group, and more preferably a pyridyl group and a pyrimidinyl group.

R _T3 ', R _T3 , R _T4 , R _T5 and R _T6 are preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a perfluoroalkyl group, a dialkylamino group, a fluorine atom, More preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a fluorine atom or an aryl group, 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 bonded to each other to form a condensed 4- to 7-membered ring, the condensed 4- to 7-membered ring is cycloalkyl, aryl or heteroaryl, The condensed 4- to 7-membered ring may further have a substituent T. The definitions and preferable ranges of the cycloalkyl, aryl and heteroaryl to be formed are the same as those of the cycloalkyl group, aryl group and heteroaryl group defined by R _T3 ', R _T3 , R _T4 , R _T5 and R _T6 .

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

Examples of the condensed aromatic heterocyclic ring represented by ring Q include a quinoline ring, an isoquinoline ring, and a quinoxaline ring. Is preferably a quinoline ring or an isoquinoline ring, more preferably a quinoline ring.

m is preferably 1 to 3, more preferably 2 or 3. That is, n is preferably 0 or 1. The kind of the ligand in the complex is preferably one or two kinds, more preferably one kind. When a reactive group is introduced into the complex molecule, it is preferable that the ligand is composed of two kinds in view of ease of synthesis.

The metal complex represented by the general formula (T-1) is obtained by reacting a ligand represented by the following general formula (T-1-A) or a tautomer thereof in the general formula (T-1) with a ligand represented by (XY) Or all of the ligands of the metal complex may be composed only of a ligand represented by the following general formula (T-1-A) or a tautomer thereof.

(32)

(General formula (T-1-A) _{of, R T3 ', R T3,} R T4, R T5, R T6, E and Q, R _T3 in the general formula (T-1)', R T3, R _T4 , R _T5 , R _T6 , E and Q. * represents the coordination position for iridium.

The ligand may also be a known ligand (also referred to as a coordination compound) used as a ligand, which is used in the formation of a conventionally known metal complex, as a ligand (X-Y), if necessary.

As ligands used in conventionally known metal complexes, there are various known ligands. For example, &quot; Photochemistry and Photophysics of Coordination Compounds &quot; published by H. Yersin, Springer-Verlag, (For example, a halogen ligand (preferably a chlorine ligand), a nitrogen nitrogen heteroaryl ligand (for example, bipyridyl, phenanthroline, etc.) described in the publication of Akio Yamamoto, , A diketone ligand (e.g., acetylacetone), etc. As the ligand represented by (XY), a diketone or a picolinic acid derivative is preferable. From the standpoint of stability of the complex and high luminescence efficiency, And most preferably acetylacetonate (acac) shown in FIG.

(33)

* Indicates the coordination position with respect to iridium.

Hereinafter, examples of ligands represented by (X-Y) are specifically described, but the present invention is not limited thereto.

(34)

In the examples of the ligand represented by the formula (X-Y), * represents a coordination position with respect to iridium in the formula (T-1). Rx, Ry and Rz each independently represent a hydrogen atom or a substituent. Examples of the substituent include a substituent selected from the above-mentioned substituent group A. Preferably, each of Rx and Rz independently represents 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 , A phenyl group which may be substituted, and most preferably a methyl group, an ethyl group, a trifluoromethyl group, a fluorine atom and a phenyl group. 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 a phenyl group which may be substituted, An atom, or a methyl group. Rx, Ry, and Rz are chemically stable substituents, and do not affect the effect of the present invention, since these ligands are considered to be regions where electrons are not transported or carried by charge in the device. (I-1), (I-4), and (I-5), and most preferably (I-1). The complexes having these ligands can be synthesized in the same manner as the known synthesis examples by using the corresponding ligand precursors. For example, the method described in International Publication No. 2009-073245, page 46, can be synthesized by the following method using commercially available difluoroacetylacetone.

(35)

As the ligand, a monoanionic ligand represented by the general formula (I15) may also be used.

(36)

R _T7 to R _{T10 in the} general formula (I-15) Is the same as R _T3 to R _{T6 in the} general formula (T-1), and the preferable range is also the same. R _T7 'to R _T10 ' are synonymous with R _T3 ', and the preferred range is also the same as R _T3 '. * Indicates the coordination position with respect to iridium.

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

(37)

(In the general formula (T-2), R _T3 'to R _T6 ' and R _T3 to R _T6 They are each independently a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, -CN, a vinyl group to a perfluoroalkyl group, _{trifluoromethyl, -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 may further have a substituent T.

R _T3 , R _T4 , R _T5 and R _T6 Two arbitrary adjacent two of them may combine with each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring may further have a substituent Z.

R _T3 'and R _{T6 Is, -C (R T) 2 -C} (R T) 2 -, -CR T = CR T -, -C (R T) 2 -, -O-, -NR T -, -OC (R T) ₂ -, -NR _T -C (R _T ) ₂ - and -N = CR _T -, to form a ring.

R _T Each independently represent 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 is independently selected from the group consisting of a fluorine atom, -R ', -OR', -N (R ') ₂ , -SR', -C (O) _{) N (R ') 2,} -CN, -NO 2, -SO 2, -SOR', -SO 2 R represents a ', or -SO ₃ R', R 'are, each independently, a hydrogen atom, an alkyl group, A perfluoroalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

(X-Y) 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 formula _{(T-2) R T3 '} , R T3 ~ R T6, (XY), the preferable range of m and n is, R _T3 in the general formula (T-1)', R T3 ~ R _T6 , (XY), m and n.

R _T4 'is preferably a hydrogen atom, an alkyl group, an aryl group or a fluorine atom, more preferably a hydrogen atom.

R _T5 'and R _T6 ' each represent a hydrogen atom, or combine with each other to form a condensed 4- to 7-membered cyclic group, and the condensed 4- to 7-membered cyclic group is preferably a cycloalkyl, cycloheteroalkyl, aryl , Or heteroaryl, and more preferably 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 preferred form of the represented by the above-mentioned formula (T-2) compound, R _T3 ', R _T4' in the general formula _{(T-2), R T5} ', R T6', R T3, R T4, R _T5 and R _T6 are adjacent to each other are not bonded to each other to form a condensed ring.

One preferred form of the compound represented by the formula (T-2) is a case represented by the following formula (T-3).

(38)

R _T3 'to R _T6 ', R _T3 to R _{T6 in the} general formula (T-3) R _T3 'to R _T6 ', R _T3 to R _{T6 in the} general formula (T-2) And the preferred range is the same.

R _T7 ~ R _T10 Are in agreement with R _T3 to R _T6, and the preferable range is also the same. R _T7 'to R _T10 ' are in agreement with R _T3 'to R _T6 ', and the preferred ranges are also the same.

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

[Chemical Formula 39]

In formula _{(T-4) R T3 '} ~ R T6', R T3 ~ R T6, R T3 '~ R T6' in the (XY), m and n have the general formula (T-2) , R _T3 to R _T6 , (XY), m and n, and the preferred ranges are also the same. Of R _T3 'to R _T6 ' and R _T3 to R _T6 , it is particularly preferable that 0 to 2 are alkyl or phenyl groups and all others are hydrogen atoms. Among R _T3 'to R _T6 ' and R _T3 to R _T6 , It is more preferable that one or two of them are an alkyl group and all others are hydrogen atoms.

Another preferable form of the compound represented by the above general formula (T-2) is a compound represented by the following general formula (T-5).

(40)

In formula _{(T-5) R T3 '} ~ R T7', R T3 ~ R T6, R T3 '~ R T6' in the (XY), m and n have the general formula (T-2) , R _T3 to R _T6 , (XY), m and n, and preferred ones are also the same.

Another preferred form of the compound represented by formula (T-1) is a case represented by the following formula (T-6).

(41)

In the general formula (T-6), the definitions and preferable ranges of R _1a to R _1i are the same as those in R _T3 to R _T6 in the general formula (T-1). It is particularly preferable that 0 to 2 of R _1a to R _1i are an alkyl group or an aryl group, and all others are hydrogen atoms. (XY), m and n are the same as (XY), m and n in the general formula (T-1).

Another preferred form of the compound represented by the formula (T-1) is a case represented by the following formula (TC-1).

(42)

(In the general formula (TC-1), R _T3 'to R _T5 ' and R _T3 to R _T6 They are each independently a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cyano group, a vinyl group to a perfluoroalkyl group, _{trifluoromethyl, -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 may further have a substituent T.

R _T3 , R _T4 , R _T5 and R _T6 Any two adjacent ones may combine with each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring may further have a substituent T.

R _T3 ', R _T4 ' and R _T5 'may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring may further have a substituent T.

R _T3 'and R _{T6 Is, -C (R T) 2 -C} (R T) 2 -, -CR T = CR T -, -C (R T) 2 -, -O-, -NR T -, -OC (R T) ₂ -, -NR _T -C (R _T ) ₂ - and -N = CR _T -, to form a ring.

R _T Each independently represent 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 is independently selected from the group consisting of a fluorine atom, -R ', -OR', -N (R ') ₂ , -SR', -C (O) _{) N (R ') 2,} -CN, -NO 2, -SO 2, -SOR', -SO 2 R represents a ', or -SO ₃ R', R 'are, each independently, a hydrogen atom, an alkyl group, A perfluoroalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

(X-Y) represents a ligand. m represents an integer of 1 to 3, and n represents an integer of 0 to 2. m + n is 3.)

A preferable range of R _T3 ', R _T3 to R _T6 , (XY), m and n in the general formula (TC-1) is R _T3 ', R _T3 to R _T6 , (XY), m and n.

R _T4 'is preferably a hydrogen atom, an alkyl group or an aryl group, 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, more preferably an aryl group having 6 to 20 carbon atoms. Examples of the aryl group include phenyl, naphthyl, biphenyl, anthryl, terphenyl, fluorenyl, phenanthryl, pyrenyl, triphenylenyl, tolyl, A biphenyl group, a triphenylenyl group, an anthryl group, or a terphenyl group is preferable, and a phenyl group, a biphenyl group, a naphthyl group and a 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 is preferably an alkyl group having from 1 to 10 carbon atoms, and examples thereof include a methyl group, an ethyl group, an isopropyl group, a t-butyl group, an n-octyl group, a n-decyl group, a n-hexadecyl group, A methyl group, an ethyl group, an isopropyl group, and a t-butyl group are more preferable, and a methyl group is more preferable.

One preferred form of the above general formula (TC-1) is a case where any two adjacent R _T4 , R _T5 and R _T6 bond to each other to form a condensed ring. The ring is more preferably a cycloalkyl, a cycloheteroalkyl, an aryl, or a heteroaryl. In particular, R _T4 , R _T5 Are 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 formula (TC-1) is preferably the following formula (TC-2).

(43)

(In the formula (TC-2), R _T3 'to R _T5 ', R _T3 , R _T6 , and R _TC1 to R _TC4 A perfluoroalkyl group, a trifluorovinyl group, -CO ₂ R _T , -C (O) R _T , -N (R _T ) 2, ₂ , -NO ₂ , -OR _T , a halogen atom, an aryl group or a heteroaryl group, and may further have a substituent T.

R _T3 ', R _T4 ' and R _T5 'may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring may further have a substituent T.

R _T3 'and R _{T6 Is, -C (R T) 2 -C} (R T) 2 -, -CR T = CR T -, -C (R T) 2 -, -O-, -NR T -, -OC (R T) ₂ -, -NR _T -C (R _T ) ₂ - and -N = CR _T -, to form a ring.

R _T Each independently represent 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 is independently selected from the group consisting of a fluorine atom, -R ', -OR', -N (R ') ₂ , -SR', -C (O) _{) N (R ') 2,} -CN, -NO 2, -SO 2, -SOR', -SO 2 R represents a ', or -SO ₃ R', R 'are, each independently, a hydrogen atom, an alkyl group, A perfluoroalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

W represents a hydrogen atom or a carbon atom, an oxygen atom or a sulfur atom to which the substituent T is bonded.

(X-Y) 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 formula _{(TC-2) R T3 '} ~ R T5', R T3 and R _T6, (XY), the preferable range of m and n is, R _T3 'in the formula (TC-1) ~ R _T5 ', R _T3 and R _T6 , (XY), m and n.

The preferable range of R _TC1 to R _TC4 is the _{same as} the preferable range of R _T3 , and is preferably a hydrogen atom, an alkyl group, or an aryl group, 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 a methyl group.

The general formula (TC-1) is also described in JP-A-2008-147353.

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

(44)

[Chemical Formula 45]

(46)

(47)

The compound exemplified as the compound represented by the general formula (T-1) can be synthesized by various methods described in Japanese Patent Laid-Open Publication No. 2009-99783, and US Pat. No. 7279232. [ After the synthesis, it is preferable to carry out purification by column chromatography, recrystallization and the like, and then purify by sublimation purification. By the sublimation purification, it is possible not only to separate organic impurities, but also to effectively remove inorganic salts and residual solvents.

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

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

(48)

In the general formula (T-7), R_T11 ~ R_T17 (R-2) in the general formula (T-2)_T3 ~ R_T6 And the preferred range is the same. (X-Y), n, and m are synonymous with (X-Y), n, and m in the general formula (T-2), and preferable ranges are also the same.

Preferred examples of these are listed below, but the present invention is not limited thereto.

(49)

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

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

The light emitting layer in the element of the present invention may be 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 one dopant or two or more kinds of dopants may be used. The host material is preferably a charge transporting material. The host material may be one species or two or more species. For example, a mixture of a host material of electron transporting property and a host material of hole transporting property may be cited. The light emitting layer may contain a material which does not have charge transportability and does not emit light.

The light-emitting layer may be a single layer or a multilayer of two or more layers. Each of the light emitting layers may emit light of different colors.

<Host material>

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

In addition to the compound represented by the general formula (1), the host material used in the present invention may contain the following compounds.

The host material may be an electron transporting material and a hole transporting material, and is preferably a charge transporting material. The host material may be one species or two or more species. For example, a mixture of a host material of electron transporting property and a host material of hole transporting property may be cited.

(9,4-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, (N-vinylcarbazole), aniline-based copolymer, anthraquinone-based copolymer, anthraquinone-based compound, anthracene-based compound, A conductive polymer oligomer such as a thiophene oligomer or a polythiophene, an organic silane, a carbon film, a pyridine compound such as pyridine, pyrimidine, triazine, imidazole, pyrazole, triazole, oxazole, oxadiazole, fluorene, anthraquinodimethane , Anthrone, diphenylquinone, thiopyran dioxide, carbodiimide, fluorenylidenemethane, distyrylpyrazole , Fluorine-substituted aromatic compounds, heterocyclic tetracarboxylic acid anhydrides such as naphthalene perylene, metal complexes of phthalocyanine and 8-quinolinol derivatives, and metal complexes containing metal phthalocyanine, benzoxazole or benzothiazole as ligands Various metal complexes and derivatives thereof (which may have substituents or axial rings), and the like.

In the light emitting layer in the present invention, the host material triplet minimum excitation energy (T ₁ Energy) of the phosphorescent material is lower than the T ₁ Is higher than energy in terms of color purity, luminous efficiency and drive durability.

The content of the host compound in the present invention is not particularly limited, but is preferably 15% by mass or more and 95% by mass or less with respect to the total mass of the compound forming the light-emitting layer from the viewpoint of the light emitting efficiency and the drive voltage.

(Charge transport layer)

The charge transport layer refers to a layer in which charge transfer occurs when a voltage is applied to the organic electroluminescent element. Specifically, a hole injecting layer, a hole transporting layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, or an electron injecting layer can be given. Preferably, it is a hole injection layer, a hole transporting layer, an electron blocking layer or a light emitting layer. If the charge transporting layer formed by the coating method is a hole injecting layer, a hole transporting layer, an electron blocking layer, or a light emitting layer, it is possible to manufacture an organic electroluminescent device at a low cost and with high efficiency. The charge transporting layer is more preferably a hole injecting layer, a hole transporting layer, or an electron blocking layer.

(Hole injection layer, hole transport layer)

The hole injection layer and the hole transport layer are layers having a function of accepting 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 in, for example, 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 transporting layer is preferably from 1 nm to 500 nm, more preferably from 5 nm to 200 nm, and further preferably from 10 nm to 100 nm.

The thickness of the hole injection layer is preferably 0.1 nm to 200 nm, more preferably 0.5 nm to 100 nm, and further preferably 1 nm to 100 nm.

The following compounds can also be preferably used as the hole injecting material.

(50)

The hole injection layer preferably contains an electron-accepting dopant. By including an electron-accepting dopant in the hole injecting layer, the hole injecting property is improved, the driving voltage is lowered, and the efficiency is improved. The electron-accepting dopant may be any organic material or inorganic material as long as it can extract electrons from the material to be doped to generate radical cation, and examples thereof include tetracyanoquinodimethane (TCNQ), tetrafluoro (F ₄ -TCNQ), molybdenum oxide, and the like.

The electron-accepting dopant in the hole-injecting layer is preferably contained in an amount of 0.1% by mass to 50% by mass, more preferably 0.1% by mass to 40% by mass, more preferably 0.5% By mass to 30% by mass.

(Electron injection layer, electron transport layer)

The electron injection layer and the electron transport layer are layers having a function of accepting electrons from the cathode or the cathode side and transporting them to the anode side. The electron injecting material and the electron transporting material used in 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 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 publications can be applied to the present invention.

The thickness of the electron transporting layer is preferably from 1 nm to 500 nm, more preferably from 5 nm to 200 nm, and further preferably from 10 nm to 100 nm.

The thickness of the electron injection layer is preferably 0.1 nm to 200 nm, more preferably 0.2 nm to 100 nm, and still more preferably 0.5 nm to 50 nm.

In the device of the present invention, it is preferable that the electron transporting layer contains the compound represented by the above general formula (E-1).

The electron injecting layer preferably contains an electron donating dopant. Including an electron donating dopant in the electron injecting layer has the effect of improving the electron injecting property, lowering the driving voltage, and improving the efficiency. The electron donor dopant may be any of organic materials and inorganic materials as long as it is capable of imparting electrons to the material to be doped and generating radical anions. Examples of the electron donating dopant include tetrathiafulvalene (TTF), tetrathia Naphthacene (TTT), lithium, cesium and the like.

The electron donor dopant in the electron injecting layer is preferably contained in an amount of 0.1% by mass to 50% by mass, more preferably 0.1% by mass to 40% by mass, and more preferably 0.5% by mass with respect to the total mass of the compound forming the electron injecting layer By mass to 30% by mass.

By including an electron-accepting dopant in the hole-injecting layer and an electron-donating dopant in the electron-injecting layer, it is possible to promote the injection of charges from the electrodes in general and lower the driving voltage, The light emitting position is changed to lower the light emission efficiency, lower the driving durability, and promote various changes at the time of high luminance driving. The device of the present invention is less prone to charge accumulation in the device due to the charge injection barrier in the light emitting layer adjacent layer / light emitting layer interface on the cathode side and the charge trap in the adjacent layer of the light emitting layer on the light emitting layer or on the cathode side, The electron mobility of the adjacent layer, the hole mobility of the light emitting layer, and the electron mobility are good, the balance of the charge is hardly balanced against the change of the charge injection amount. Therefore, By including the electron donor dopant in the electron injecting layer, the driving voltage can be lowered without deteriorating the efficiency, durability, various changes during high luminance driving, and the like.

(Hole blocking layer)

The hole blocking layer is a layer having a function of preventing the holes transported from the anode side to the light emitting layer from escaping to the cathode side. In the present invention, a hole blocking layer can be formed as an organic layer adjacent to the light emitting layer and the cathode side.

Examples of the organic compound constituting the hole blocking layer include aluminum (III) bis (2-methyl-8-quinolinato) 4-phenyl phenolate (Aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate (abbreviated as BAlq)), triazole derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthrol Phenanthroline derivatives such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (abbreviated as BCP), triphenylene derivatives, carbazole derivatives and the like.

The triphenylene derivatives are described, for example, in WO 05/013388, WO 06/130598, WO 09/021107. The triphenylene derivative is preferably a compound represented by the following formula (Tp-1).

(51)

(In the general formula (Tp-1), R ¹² to R ²³ A phenyl group, a fluorenyl group, a naphthyl group or a triphenylenyl group which may be substituted with a hydrogen atom, an alkyl group or an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group or a triphenylenyl group. However, R ¹² to R ²³ Are not all hydrogen atoms.)

R ¹² to R ²³ Examples of the alkyl group represented by R 1 include a methyl group, an ethyl group, an isopropyl group, an n-butyl group, a t-butyl group, an n-octyl group, a n-decyl group, a n-hexadecyl group, a cyclopropyl group, , A cyclohexyl group and the like. Of these, a methyl group, an ethyl group, an isopropyl group, a t-butyl group and a cyclohexyl group are preferable, and a methyl group, an ethyl group or a t-butyl group is more preferable.

As R ¹² to R ²³ , 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 triphenylrenyl group (these are also 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 lower alkyl 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 be a single layer structure composed of one or more of the above-described materials, or a multi-layer structure composed of plural layers of 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 escaping to the anode side. In the present invention, an electron blocking layer can be formed as an organic layer adjacent to the light emitting layer and the anode side.

As examples of the organic compound constituting the electron blocking layer, any of the above-mentioned hole transporting materials 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 electronic block layer may be a single layer structure composed of one or more of the above-described materials, or a multi-layer structure composed of a plurality of layers of the same composition or different compositions.

(Protective layer)

In the present invention, the entire organic EL device may be protected by a protective layer.

The material contained in the protective layer may be any material having a function of suppressing entry of moisture, oxygen, or the like into the device to promote deterioration of the device.

As for the protective layer, the matters described in paragraphs [0169] to [0170] of Japanese Patent Application Laid-Open No. 2008-270736 can be applied to the present invention.

(Sealing container)

In the device of the present invention, the entire device may be sealed using an encapsulating container.

As for the sealing container, the matters described in the paragraph [0171] of Japanese Laid-Open Patent Publication No. 2008-270736 can be applied to the present invention.

In addition, a water absorbent or an inert liquid may be sealed in the space between the sealing container and the light emitting element. The water absorbent is not particularly limited and includes, for example, barium oxide, sodium oxide, potassium oxide, calcium oxide, sodium sulfate, calcium sulfate, magnesium sulfate, phosphorus pentoxide, calcium chloride, magnesium chloride, , 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.

(Driving)

In the organic electroluminescent device of the present invention, light emission can be obtained by applying a direct current (which may include an alternating current component if necessary) voltage (usually 2 to 15 volts) or a direct current between the anode and the cathode.

The driving method of the organic electroluminescent device of the present invention is described in JP-A-2-148687, JP-A-6-301355, JP-A-5-29080, JP- The driving methods described in the specification of each of Japanese Patent Application Laid-Open No. 134558, Japanese Patent Application Laid-Open Nos. 8-234685 and 8-241047, Japanese Patent No. 2784615, USP 5828429 and USP 6023308 have.

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

The internal quantum efficiency of the organic electroluminescent device of the present invention is preferably 30% or more, more preferably 50% or more, and still more 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 typical organic EL device, the light extraction efficiency is about 20%. However, by studying 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, To 20% or more.

The organic electroluminescent device of the present invention preferably has a maximum emission wavelength (maximum intensity wavelength of emission spectrum) of 350 nm or more and 700 nm or less, more preferably 350 nm or more and 600 nm or less, further preferably 400 nm or less Or more and 520 nm or less, particularly preferably 400 nm or more and 465 nm or less.

(Use of the Light-emitting Element of the Present Invention)

The light emitting device of the present invention can be suitably used for a light emitting device, a pixel, a display device, a display, a backlight, an electrophotographic light, an illumination light source, a recording light source, an exposure light source, a reading light source, a mark, a signboard, an interior or an optical communication. Particularly, it is preferably used for a device that is driven in a region where the light emission luminance is high, such as a lighting device or 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 is formed using the organic electroluminescent device.

2 is a cross-sectional view schematically showing an example of a light emitting device of the present invention.

2 is constituted by a substrate (support substrate) 2, an organic electroluminescence device 10, a sealing container 16, and the like.

The organic electroluminescent device 10 is constituted by sequentially stacking a positive electrode (first electrode) 3, an organic layer 11, and a negative electrode (second electrode) 9 on a substrate 2. An encapsulation container 16 is formed on the protective layer 12 with an adhesive layer 14 interposed therebetween. Further, a part of each of the electrodes 3 and 9, a partition wall, an insulating layer, and the like are omitted.

As the adhesive layer 14, a photocurable adhesive such as an epoxy resin or a thermosetting adhesive may be used. For example, a thermosetting adhesive sheet may be used.

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

(Lighting device)

Next, a lighting apparatus according to an embodiment of the present invention will be described with reference to Fig.

3 is a cross-sectional view schematically showing an example of a lighting apparatus 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 is provided with the above-described organic EL element 10 and the light scattering member 30. As shown in Fig. More specifically, the illumination 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 the fine particles 32 are dispersed on the transparent substrate 31. [ As the transparent substrate 31, for example, a glass substrate is preferably used. As the fine particles 32, transparent resin fine particles are preferably used. As the glass substrate and the transparent resin fine particles, all known ones can be used. When the light emitted from the organic electroluminescent element 10 is incident on the light incidence surface 30A of the light scattering member 30, the incident light is scattered by the light scattering member 30, And the scattered light is emitted from the light output surface 30B as illumination light.

Example

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 WO 2004/074399 pamphlet. For example, the compound (1) can be synthesized by the method described in International Patent 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 Patent Publication No. 4308663.

All of the organic materials used in this example were analyzed by high performance liquid chromatography (Toso TSKgel ODS-100Z) by sublimation purification and had an absorption intensity area ratio of 254 nm, and those having a purity of 99.9% or more Used.

[Example 1]

&Lt; Production of Organic Electroluminescent Device &gt;

A glass substrate (ITO film thickness: 100 nm) having an indium tin oxide (ITO) film with a thickness of 0.7 mm and a width of 2.5 cm was placed in a cleaning container, ultrasonically cleaned in 2-propanol and subjected to UV-ozone treatment for 30 minutes did. Each of the following layers was deposited on this glass substrate by a vacuum evaporation method using a vacuum deposition apparatus (Small-ELVESS, manufactured by Tokki Corporation). The vacuum deposition methods in the following examples and comparative examples are all performed under the same conditions, and the deposition rate is 0.2 nm / sec unless otherwise noted. The deposition rate was measured using a quartz oscillator. The pressure is 1 x ^10-4 Pa or less. The thickness of each of the following layers was measured using a quartz oscillator.

HIL-1 (purity: 97%) was vacuum-deposited on the anode (ITO) so as to have a thickness of 10 nm as a hole injection layer.

Next, N, N'-dinaphthyl-N, N'-diphenyl- [1,1'-biphenyl] -4,4'-diamine (NPD) was formed as a hole transport layer By vacuum deposition so as to have a thickness of 30 nm.

Next, a light-emitting layer containing 85: 15 mass ratio of compound (A-1) (host material) and Ir-A (guest) as a light emitting material was vacuum deposited on the hole transport layer so as to have a thickness of 30 nm .

Next, HBL-A was vacuum-deposited on the light-emitting layer so as to have a thickness of 10 nm to form a hole blocking layer.

Subsequently, a film was formed by vacuum evaporation of e-4 as an electron transporting layer so as to have a thickness of 30 nm on the hole blocking layer.

Next, LiF was deposited as an electron injecting layer on the electron transporting layer by vacuum evaporation to a thickness of 1 nm.

Next, a mask patterned as a cathode (a mask having a light emitting region of 2 mm x 2 mm) was provided, and a film was formed by vacuum evaporation of metal aluminum so as to have a thickness of 100 nm.

The laminate thus prepared was placed in a glove box substituted with argon gas, sealed with glass, and sealed with an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.). Thus, the organic electroluminescent device of Example 1 was produced.

In order to measure the amount of change in chromaticity due to the thickness of the electron transporting layer, the device manufactured in the same manner as above except that the thickness of the electron transporting layer was made 10 nm thick and the device manufactured in the same manner as described above except that the electron transporting layer was made thinner by 10 nm One device was also manufactured.

(evaluation)

The luminous efficiency, the drive voltage, the durability and the chromaticity of the manufactured organic electroluminescent device of Example 1 were evaluated as follows, and the roll-off (efficiency reduction in high-luminance driving) and the change amount of the chromaticity x per 10 nm Respectively.

<Measurement of luminous efficiency and driving voltage>

The emission luminance of the organic electroluminescent device driven at a constant current density (10 mA / cm 2) was measured with a spectral radiance luminance meter (SR-3, manufactured by Topcon), and the external quantum efficiency (%) was obtained.

The voltage at that time was measured to obtain the driving voltage (V).

The external quantum efficiency and driving voltage of Comparative Example 3 were set to 100, the external quantum efficiency and the driving voltage of Comparative Example 11 were set to 100 in Table 2, and the external quantum efficiency and the driving voltage in Comparative Example 11 were set to 100 The quantum efficiency and the driving voltage are set to 100, and in Table 4, the external quantum efficiency and the driving voltage of Comparative Example 24 are taken as 100 and expressed as relative values.

<Measurement of durability>

The time (h) until the luminance reached 500 cd / m &lt; 2 &gt; by continuously emitting the organic electroluminescent device while maintaining the current density at a luminance of 1,000 cd / m &lt; 2 &gt;

The durability of Comparative Example 3 was set to 100 in Table 1, the durability of Comparative Example 11 was set to 100 in Table 2, the durability of Comparative Example 17 was set to 100 in Table 3, The durability of Example 24 was taken as 100 and expressed as a relative value.

<Rolloff Calculation>

The roll-off was evaluated by the luminous efficiency at a luminance of 1,000 cd / m 2 divided by the luminous efficiency at a luminance of 10,000 cd / m 2. The larger the value, the more the rolloff is suppressed. The emission efficiency was measured in the same manner as described above.

&Lt; Measurement of chromaticity &

A direct current constant voltage was applied to the organic electroluminescent element of Example 1 using a source major unit Model 2400 manufactured by Toyotecnica to emit light. The obtained luminescence spectrum was measured by a luminescence spectrum measurement system (ELS 1500) manufactured by Shimadzu Corporation, and the x value was calculated from the obtained spectrum by using a CIE colorimetric system. The x value is a value at a current density of 10 mA / cm 2.

&Lt; Calculation of change amount of chromaticity x per 10 nm of thickness of electron transporting layer &gt;

The change amount of the chromaticity x per 10 nm of the electron transporting layer (the film thickness on the x-axis and the chromaticity on the y-axis when the chromaticity was taken on the y-axis) were measured from the chromaticity x measured for three devices having different electron transporting film thicknesses Tilt).

[Examples 2 to 31 and 33, and Comparative Examples 1 to 27 and 29]

A device was manufactured and evaluated in the same manner as in Example 1 except that the composition of the device, 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% by mass with respect to the total mass of the light emitting layer.

[Example 32 and Comparative Example 28]

(3,4-ethylenedioxythiophene) -poly (styrene sulfonic acid (PEDOT.PSS) aqueous solution (manufactured by Bayer)) of about 3000 to 4000 rpm on the surface of a glass substrate having an indium tin oxide (ITO) The device of Example 32 was produced and evaluated in the same manner as in Example 22 except that the hole injection layer was formed by baking at 200 캜 after removing the film other than the luminescent region by spin coating. Was changed to mCP, the device of Comparative Example 28 was produced and evaluated in the same manner as in Example 32. [

[Comparative Example 30]

A device of Comparative Example 30 was manufactured and evaluated in the same manner as in Example 1, except that the composition of the device, 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, it can be seen that the device of Comparative Example 30 greatly suppressed the reduction of efficiency (roll-off) at the time of high-luminance driving and suppressed the dependence of the chromaticity on the thickness of the electron transporting layer in the device of Example 1.

The results of Tables 1 to 5 show that, in the device of the embodiment, rolloff is suppressed and the dependency of the chromaticity on the electron transport layer film thickness is small for the device of the comparative example.

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

(52)

(53)

(54)

(55)

(56)

(57)

(58)

Industrial availability

According to the present invention, it is possible to provide a light emitting device which is excellent in terms of luminous efficiency, driving voltage and durability, has a small decrease in efficiency at the time of high-luminance driving and has a film thickness of a layer containing a compound having electron- It is possible to provide an organic electroluminescent device in which the emission chromaticity is hardly dependent.

While the invention has been described in detail and with reference to specific embodiments thereof, it is evident to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the invention.

The present application is based on Japanese Patent Application (Japanese Patent Application No. 2010-157356) filed on July 9, 2010, the content of which is incorporated herein by reference.

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 device
11: Organic layer
12: Protective layer
14: Adhesive layer
16: Encapsulation container
20: Light emitting device
30: light scattering member
31: transparent substrate
30A: light incidence surface
30B: light emitting surface
32: particulate
40: Lighting device

Claims (15)

An organic electroluminescent device having a pair of electrodes composed of an anode and a cathode and a light emitting layer between the electrodes and having at least one organic layer between the light emitting layer and the cathode,
Wherein the light emitting layer contains at least one compound represented by the following general formula (1)
An organic electroluminescent element comprising at least one compound represented by the following formula (E-1) in at least one organic layer between the light emitting layer and the cathode:

Here, 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 does not represent a carbazolyl group or a perfluoroalkyl group , if R ₁ is present a plurality, the plurality of R ₁ is, each may be the same or different, a plurality of R ₁ is in addition, it is possible to form an aryl ring which may have a substituent Z combine with each other,
R ₂ to R ₅ each independently represent 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, ₂ to R &lt; ₅ &gt; may be the same or different,
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 substituents Z, Lt; / RTI &gt;
n1 represents an integer of 0 to 5,
n2 to n5 each independently represents an integer of 0 to 4;

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, R _E1 and R _E2 are not hydrogen atoms at the same time,
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 method according to claim 1,
Wherein the compound represented by the general formula (1) is represented by the following general formula (2)

In the general formula (2), R ₆ and R ₇ each independently represent 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, R ₆ and R ₇ each represent When a plurality is present, the plurality of R ₆ and the 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 You can,
n6 and n7 each independently represent an integer of 0 to 5,
R ₈ to R ₁₁ each independently represent a hydrogen atom, an alkyl group which may have a substituent Z, an aryl group which may have an alkyl group, a silyl group which may have a substituent Z, 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 substituents Z, Can be formed. The method according to claim 1,
In the general formula (E-1), R _E4 is an unsubstituted aryl group. The method according to claim 1,
In the general formula (E-1), Ar is an unsubstituted arylene group. The method according to claim 1,
In the general formula (E-1), R _E4 is a phenyl group. The method according to claim 1,
In the general formula (E-1), Ar is a phenylene group. The method according to claim 1,
An organic electroluminescent element represented by the following formula (E-1) is represented by the following formula (E-2) or the following formula (E-3)

In the formulas (E-2) and (E-3), R _E1 and R _E2 each independently represent a hydrogen atom, an aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, Aromatic heterocyclic group, provided that 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 method according to claim 1,
And R _E3 is a hydrogen atom. The method according to claim 1,
_Wherein R _E1 and R _E2 are each independently a naphthyl group. The method according to claim 1,
Wherein the light emitting layer contains a phosphorescent light emitting material. 11. The method of claim 10,
Wherein the phosphorescent light emitting material is a compound represented by the following general formula (T-1):

In the formula (T-1), R _T3 ', R _T3 , R _T4 , R _T5 and R _T6 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, vinyl _{trifluoromethyl, -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, the substituent further T, &lt; / RTI &gt;
E represents a carbon atom or a nitrogen atom,
Q is a 5- or 6-membered aromatic heterocyclic ring or condensed aromatic heterocyclic ring containing one or more nitrogen atoms,
In the ring Q, a line connecting E and N is represented by a single line, which may be a single bond or a double bond,
R _T3 , R _T4 , R _T5 and R _T6 may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or heteroaryl , The condensed 4- to 7-membered ring may further have a substituent T,
R _T3 'and _T6 is _{R, -C (R T) 2 -C} (R T) 2 -, -CR T = CR T -, -C (R T) 2 -, -O-, -NR T -, -OC (R _T ) ₂ -, -NR _T -C (R _T ) ₂ - and -N = CR _T -, and R _T is independently selected from the group consisting of hydrogen 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 is independently selected from the group consisting of a fluorine atom, -R ', -OR', -N (R ') ₂ , -SR', -C (O) _{) N (R ') 2,} -CN, -NO 2, -SO 2, -SOR', -SO 2 R represents a ', or -SO ₃ R', R 'are, each independently, a hydrogen atom, an alkyl 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 is an integer of 1 to 3, n is an integer of 0 to 2, and m + n is 3. The method according to claim 1,
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. A light-emitting device using the organic electroluminescent device according to any one of claims 1 to 12. A display device using the organic electroluminescent device according to any one of claims 1 to 12. An illumination device using the organic electroluminescent device according to any one of claims 1 to 12.

Images