JP2015096526A - Organic electroluminescent element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To produce a red phosphorescent material that emits light with excellent color and has easy sublimation and evaporation.SOLUTION: A compound represented by the general formula (10) and a compound represented by the general formula (11) are reacted, where A represents an aromatic heterocycle including nitrogen atoms, B represents an aromatic ring or an aromatic heterocycle, and Rto Reach represent an alkyl group, an aryl group, or the like with at least one thereof including a fluorine atom.)

Description

  The present invention relates to an organic electroluminescent device (hereinafter, also referred to as “organic EL device”, “light emitting device” or “device”) that can emit light by converting electric energy into light, and in particular, emission characteristics and durability. The present invention relates to an organic electroluminescent device having excellent resistance.

  Today, research and development on various display elements (organic light-emitting elements) using organic light-emitting materials is active, and among them, organic EL elements can obtain high-luminance light emission at a low voltage and attract attention as promising display elements. ing.

  In recent years, the use of phosphorescent light emitting materials has led to higher device efficiency. Known phosphorescent materials include iridium complexes and platinum complexes (see, for example, Patent Documents 1 and 2).

  Further, it is known that the iridium complex phosphorescent material having a hexafluoroacetylacetonate ligand has a significantly lower emission intensity than that having an acetylacetonato ligand (Patent Literature). (See 3 etc.).

  As a red phosphorescent material, an iridium complex having a quinoline ring or an isoquinoline ring as a partial structure of the ligand is disclosed, but further improvement is required regarding the color as red and the thermal behavior of the material. Yes.

US Pat. No. 6,303,238 International Publication No. 00/57676 Pamphlet US Patent Publication 2002/0034656

An object of the present invention is to provide a red phosphorescent material that emits light with a good color and is easy to sublimate and deposit. Another object of the present invention is to provide an organic electroluminescent device having excellent light emission characteristics by using the phosphorescent material.
Another object of the present invention is to provide a composition and a light emitting layer useful for an organic electroluminescent device. Another object of the present invention is to provide a light emitting device and a lighting device including an organic electroluminescent element.

  This object has been achieved by the following means.

[1]
An organometallic complex represented by the general formula (1).

(In General Formula (1), A represents an aromatic heterocyclic ring containing a nitrogen atom, B represents an aromatic ring or an aromatic heterocyclic ring. For at least one pair of A and B, A represents a quinoline ring or an isoquinoline ring. And B represents a naphthalene ring, A and B may each have a substituent and may be further condensed, and R ¹ and R ³ each independently represents an alkyl group, an aryl group, or hetero Represents an aryl group, R ² represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, or a halogen atom, and at least one of at least one of R ¹ , R ² , and R ³ Containing fluorine atoms.)

[2]
The organometallic complex according to [1], wherein two A's are the same and two B's are the same.

[3]
The organometallic complex according to [1] or [2], wherein A is a quinoline ring.

[4]
The organometallic complex according to [1] or [2], wherein A is a 1-isoquinoline ring.

[5]
The organometallic complex according to [1] or [2], wherein A is a 3-isoquinoline ring.

[6]
The number of fluorine atoms contained in the R ¹ , R ² , and R ³ is [1] to [6], and the organometallic according to any one of [1] to [5] Complex.

[7]
Said R < ² > is a hydrogen atom, The organometallic complex as described in any one of [1]-[6] characterized by the above-mentioned.

[8]
The organometallic complex according to any one of [1] to [7], wherein R ¹ is a trifluoromethyl group and R ³ is a methyl group.

[9]
[1] A light-emitting material for an organic electroluminescent element, which is the organometallic complex according to any one of [8].

[10]
An organic electroluminescent element having a pair of electrodes and at least one organic layer including a light emitting layer between the electrodes on a substrate, wherein one of the organic layers is for organic EL according to [9] An organic electroluminescent device comprising a luminescent material.

[11]
[10] A light emitting device using the organic electroluminescent element as described in [10].

[12]
[10] An illumination device using the organic electroluminescent element as described in [10].

[13]
[10] A display device using the organic electroluminescent element as described in [10].

  The present invention improves the color tone by shortening the emission wavelength by introducing a fluorine atom into the acetylacetonato ligand of the red phosphorescent iridium (III) complex having a maximum emission wavelength longer than 610 nm. In addition, improvement in sublimation purification suitability and vapor deposition suitability by lowering the sublimation temperature was realized.

It is the schematic which shows an example (1st Embodiment) of the layer structure of the organic electroluminescent element which concerns on this invention. It is the schematic which shows an example (2nd Embodiment) of the light-emitting device which concerns on this invention. It is the schematic which shows an example (3rd Embodiment) of the illuminating device which concerns on this invention.

  The present invention will be reported in detail below.

The organometallic complex of the present invention is represented by the following general formula (1).
The organometallic complex can be used for a phosphorescent material having a red emission color. The use of the phosphorescent material is not particularly limited, and for example, it is preferably used for an organic EL (electroluminescence) element.
Moreover, the use of the organic electroluminescent element of the present invention is not particularly limited. For example, in addition to a light emitting device and a lighting device, a display device such as a television, a personal computer, a mobile phone, and electronic paper can be used.

(In General Formula (1), A represents an aromatic heterocyclic ring containing a nitrogen atom, B represents an aromatic ring or an aromatic heterocyclic ring. For at least one pair of A and B, A represents a quinoline ring or an isoquinoline ring. And B represents a naphthalene ring, A and B may each have a substituent and may be further condensed, and R ¹ and R ³ each independently represents an alkyl group, an aryl group, or hetero Represents an aryl group, R ² represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, or a halogen atom, and at least one of at least one of R ¹ , R ² , and R ³ Containing fluorine atoms.)

The aromatic heterocyclic ring containing a nitrogen atom represented by A is preferably a quinoline ring, 1-isoquinoline ring or 3-isoquinoline ring, and particularly preferably a quinoline ring. This is to realize red light emission with good color.
The aromatic ring represented by B is preferably a naphthalene ring.
For at least one set of A and B, A represents a quinoline or isoquinoline ring, and B represents a naphthalene ring. Examples of the combination of A and B include a quinoline ring and a naphthalene ring, a 1-isoquinoline ring and a naphthalene ring, a 3-isoquinoline ring and a naphthalene ring, and a quinoline ring and a naphthalene ring are preferable.
A and B may each have a substituent and may further be condensed.

The alkyl group represented by R ¹ , R ² , and R ³ preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms. For example, methyl, ethyl, n -Propyl, iso-propyl, n-butyl, tert-butyl, n-octyl, n-nonyl, n-decyl, n-dodecyl, n-octadecyl, n-hexadecyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl , 1-adamantyl, trifluoromethyl and the like. In the present invention, the “carbon number” of a substituent such as an alkyl group includes the case where a substituent such as an alkyl group may be substituted by another substituent, and also includes the carbon number of the other substituent. Used in meaning.
The aryl group represented by R ¹ , R ² , and R ³ preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms, such as phenyl or o-methyl. Phenyl, m-methylphenyl, p-methylphenyl, 2,3-xylyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 3,4-xylyl, 3,5-xylyl, 3, Examples include 6-xylyl, 4,5-xylyl, 4,6-xylyl, p-cumenyl, mesityl, naphthyl, anthranyl, and the like.
R ¹ , R ² , and R ³ represent.
The heteroaryl group represented by R ¹ , R ² , and R ³ preferably has 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms. Examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom. Specific examples include imidazolyl, pyrazolyl, pyridyl, pyrazyl, pyrimidyl, triazinyl, quinolyl, isoquinolinyl, pyrrolyl, indolyl, furyl, thienyl, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl, azepinyl and the like.
Examples of the halogen atom represented by R ¹ , R ² , and R ³ include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
At least one of R ¹ , R ² , and R ³ contains at least one fluorine atom. The number of fluorine atoms contained in R ¹ , R ² , R ³ is preferably 1-6, and more preferably 3-6. This is because if the number of fluorine atoms is within the above range, the sublimation purification yield is improved and the color is improved.
More preferably, R ¹ is a trifluoromethyl group and R ³ is a methyl group. This is to achieve both the sublimation purification yield and the improvement in color.

  The organometallic complex represented by the general formula (1) is preferably an organometallic complex represented by the general formula (2).

(In general formula (1), A ′ represents a 2-quinolyl ring, 1-isoquinolyl ring or 3-isoquinolyl ring. B ′ represents a naphthyl skeleton represented by any one of the following general formulas (2) to (4). R ⁴ and R ⁵ each independently represent a substituent on A ′ and B ′, R ¹ , R ² and R ³ each independently represent a hydrogen atom or a substituent, R ¹ , R ² , (At least one or more of R ³ is a substituent containing one or more fluorine atoms. N and m each independently represents an integer of 0 to 6.)

A represents a 2-quinolyl ring, a 1-isoquinolyl ring or a 3-isoquinolyl ring, preferably a 1-isoquinolyl ring or a 2-quinolyl ring, and more preferably a 2-quinolyl ring.
B represents a naphthyl skeleton represented by any one of the general formulas (2) to (4). The skeleton is more preferably the general formula (2) or the general formula (3), and the most preferable case is the general formula (3). In the general formulas of the general formulas (2) to (4), * is a bonding position to B.

  M and n in General formula (1) represent the integer of 0-6 each independently.

  As m, the case of 0-3 is preferable, the case of 0-2 is more preferable, the case of 0-1 is further more preferable, and the case of 0 is the most preferable.

  n is preferably 0 to 3, more preferably 0 to 2, further preferably 0 to 1, and most preferably 0.

When m is 2 or more, R ⁴ may be the same or different. When n is 2 or more, R 5 may be the same or different. When m is 1 or more and n is 1 or more, R 4 And R5 may be the same or different.

  When m is 2 or more, R4 may be bonded to each other and condensed, or when n is 2 or more, R5 may be bonded to each other and condensed.

R ^4, Examples of the substituent represented by R ⁵ is not particularly limited, for example, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an amino group, an alkoxy group, an aryloxy group, a heterocyclic group, a hetero Ring oxy group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylthio group, hydroxy group, amino group, halogen atom, acyl group, acyloxy group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino Group, sulfamoyl group, carbamoyl group, alkylthio group, arylthio group, heteroarylthio group, sulfonyl group, sulfinyl group, ureido group, phosphoric acid amide group, mercapto group, halogen atom, cyano group, sulfo group, carboxyl group, nitro group , Dorokisamu acid group, a sulfino group, a hydrazino group, an imino group, a silyl group, and a silyloxy group.

  Here, as an alkyl group, Preferably it is C1-C30, More preferably, it is C1-C20, Most preferably, it is C1-C10, for example, methyl, ethyl, n-propyl, iso-propyl, n -Butyl, tert-butyl, n-octyl, n-nonyl, n-decyl, n-dodecyl, n-octadecyl, n-hexadecyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, 1-adamantyl, trifluoromethyl Etc. In the present invention, the “carbon number” of a substituent such as an alkyl group includes the case where a substituent such as an alkyl group may be substituted by another substituent, and also includes the carbon number of the other substituent. Used in meaning.

  Moreover, as an alkenyl group, Preferably it is C2-C30, More preferably, it is C2-C20, Most preferably, it is C2-C10, for example, vinyl, aryl, 1-propenyl, 1-isopropenyl, 1 -Butenyl, 2-butenyl, 3-pentenyl and the like can be mentioned.

  The alkynyl group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. Examples thereof include ethynyl, propargyl, 1-propynyl, and 3-pentynyl. It is done.

  Moreover, as an aryl group, Preferably it is C6-C30, More preferably, it is C6-C20, Most preferably, it is C6-C12, for example, phenyl, o-methylphenyl, m-methylphenyl, p- Methylphenyl, 2,3-xylyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 3,4-xylyl, 3,5-xylyl, 3,6-xylyl, 4,5-xylyl 4,6-xylyl, p-cumenyl, mesityl, naphthyl, anthranyl, and the like.

  Further, the heteroaryl group preferably has 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom, specifically, for example, imidazolyl and pyrazolyl. , Pyridyl, pyrazyl, pyrimidyl, triazinyl, quinolyl, isoquinolinyl, pyrrolyl, indolyl, furyl, thienyl, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl, azepinyl and the like.

  The amino group preferably has 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, and particularly preferably 0 to 10 carbon atoms. For example, amino, methylamino, dimethylamino, diethylamino, dibenzylamino, Examples include diphenylamino and ditolylamino.

  Moreover, as an alkoxy group, Preferably it is C1-C30, More preferably, it is C1-C20, Most preferably, it is C1-C10, for example, methoxy, an ethoxy, butoxy, 2-ethylhexyloxy etc. are mentioned. It is done.

  Moreover, as an aryloxy group, Preferably it is C6-C30, More preferably, it is C6-C20, Most preferably, it is C6-C12, for example, phenyloxy, 1-naphthyloxy, 2-naphthyloxy, etc. Is mentioned.

  Moreover, as a heterocyclic group, Preferably it is C1-C30, More preferably, it is C1-C20, Most preferably, it is C1-C12. As a hetero atom, a nitrogen atom, an oxygen atom, a sulfur atom is mentioned, for example. Specific examples include imidazolyl, pyridyl, quinolyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl group, azepinyl group and the like.

  Moreover, as a heterocyclic oxy group, Preferably it is C1-C30, More preferably, it is C1-C20, Most preferably, it is C1-C12, for example, pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy etc. are mentioned. .

  The acyl group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 12 carbon atoms, and examples thereof include acetyl, benzoyl, formyl, and pivaloyl.

  Moreover, as an alkoxycarbonyl group, Preferably it is C2-C30, More preferably, it is C2-C20, Most preferably, it is C2-C12, for example, methoxycarbonyl, ethoxycarbonyl, etc. are mentioned.

  The aryloxycarbonyl group preferably has 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, and particularly preferably 7 to 12 carbon atoms, and examples thereof include phenyloxycarbonyl.

  Moreover, as an acyloxy group, Preferably it is C2-C30, More preferably, it is C2-C20, Most preferably, it is C2-C10, for example, acetoxy, benzoyloxy, etc. are mentioned.

  The acylamino group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms, and examples thereof include acetylamino and benzoylamino.

  Moreover, as an alkoxycarbonylamino group, Preferably it is C2-C30, More preferably, it is C2-C20, Most preferably, it is C2-C12, for example, methoxycarbonylamino etc. are mentioned.

  The aryloxycarbonylamino group preferably has 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, and particularly preferably 7 to 12 carbon atoms, and examples thereof include phenyloxycarbonylamino.

  Moreover, as a sulfonylamino group, Preferably it is C1-C30, More preferably, it is C1-C20, Most preferably, it is C1-C12, for example, methanesulfonylamino, benzenesulfonylamino, etc. are mentioned.

  The sulfamoyl group preferably has 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, and particularly preferably 0 to 12 carbon atoms. For example, sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamo Famoyl etc. are mentioned.

  The carbamoyl group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms. Examples thereof include carbamoyl, methylcarbamoyl, diethylcarbamoyl, and phenylcarbamoyl. .

  Moreover, as an alkylthio group, Preferably it is C1-C30, More preferably, it is C1-C20, Most preferably, it is C1-C12, for example, methylthio, ethylthio, etc. are mentioned.

  Moreover, as an arylthio group, Preferably it is C6-C30, More preferably, it is C6-C20, Most preferably, it is C6-C12, for example, phenylthio etc. are mentioned.

  The heterocyclic thio group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms. For example, pyridylthio, 2-benzimidazolylthio, 2-benz Examples include oxazolylthio and 2-benzthiazolylthio.

  The sulfonyl group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, and examples thereof include mesyl and tosyl.

  Moreover, as a sulfinyl group, Preferably it is C1-C30, More preferably, it is C1-C20, Most preferably, it is C1-C12, for example, methanesulfinyl, benzenesulfinyl, etc. are mentioned.

  Moreover, as a ureido group, Preferably it is C1-C30, More preferably, it is C1-C20, Most preferably, it is C1-C12, for example, ureido, methylureido, phenylureido etc. are mentioned.

  Moreover, as a phosphoric acid amide group, Preferably it is C1-C30, More preferably, it is C1-C20, Most preferably, it is C1-C12, for example, diethyl phosphoric acid amide, phenylphosphoric acid amide etc. are mentioned. It is done.

  Moreover, as a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom etc. are mentioned, for example.

  The silyl group preferably has 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, and particularly preferably 3 to 24 carbon atoms. For example, trimethylsilyl, triethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl , Tert-butyldiphenylsilyl, diphenylsilyl and the like.

  The silyloxy group preferably has 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, and particularly preferably 3 to 24 carbon atoms. For example, trimethylsilyloxy, triethylsilyloxy, triisopropylsilyloxy, tert- Examples thereof include butyldimethylsilyloxy, tert-butyldiphenylsilyloxy, diphenylsilyloxy and the like.

R ⁴ and R ⁵ are preferably an alkyl group, an aryl group, an alkenyl group, an alkoxy group, an acyl group, an amino group, a cyano group, a silyl group, or a halogen atom, and more preferably an alkyl group, an aryl group, an alkoxy group, An amino group and a halogen atom are particularly preferred, and an alkyl group, an aryl group, an alkoxy group and a halogen atom are particularly preferred, and an alkyl group and an aryl group are most preferred.

As the alkyl group for R ⁴ and R ⁵ , a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, and a tert-butyl group are preferable, a methyl group and an ethyl group are more preferable, and a methyl group Is particularly preferred.

^The aryl group of R 4, ^{R 5,} phenyl, o- methylphenyl group, m- methylphenyl group, p- methylphenyl group, a naphthyl group, anthranyl group, an imidazolyl group are preferable, phenyl group, o- A methylphenyl group, m-methylphenyl group, and p-methylphenyl group are more preferable, and a phenyl group is particularly preferable.

^As the alkenyl group of R 4, ^{R 5,} a vinyl group, an allyl group, a 1-propenyl group, 1-isopropenyl group, 1-butenyl, 2-butenyl, 3-pentenyl group are preferable, a vinyl group, An allyl group and 1-propenyl group are more preferable, and a vinyl group and an allyl group are particularly preferable.

As the alkoxy group of R ^4, R ^5, a methoxy group, an ethoxy group, a butoxy group are preferable, a methoxy group, more preferably an ethoxy group, a methoxy group is particularly preferred.

The acyl group of R ⁴ and R ⁵ is preferably an acetyl group, a benzoyl group, a formyl group, or a pivaloyl group, more preferably an acetyl group or a benzoyl group, and particularly preferably an acetyl group.

The amino group of R ⁴ and R ⁵ is preferably a dimethylamino group, a diethylamino group, or a diisopropylamino group, more preferably a dimethylamino group or a diethylamino group, and particularly preferably a dimethylamino group.

The amino group of R ⁴ and R ⁵ is preferably a methylamino group, a dimethylamino group, a diethylamino group or a diisopropylamino group, more preferably a dimethylamino group or a diethylamino group, and particularly preferably a dimethylamino group.

The silyl group of R ⁴ and R ⁵ is preferably a trimethylsilyl group, a triethylsilyl group, a triisopropylsilyl group, or a triphenylsilyl group, more preferably a trimethylsilyl group, a triethylsilyl group, or a triphenylsilyl group, and particularly preferably a trimethylsilyl group. preferable.

Further, R ^4, iodine atom as the halogen atom of R ^5, a bromine atom, a chlorine atom, preferably a fluorine atom, a chlorine atom, more preferably a fluorine atom, a fluorine atom is particularly preferred.

R ¹ containing a fluorine ^atom, R ^2, examples of the substituent of R ³ is not particularly limited, for example, fluorine atom, fluoroalkyl group, fluoroalkenyl group, fluoroalkyl group, include fluoroaryl group.

  Here, as a fluoroalkyl group, Preferably it is C1-C30, More preferably, it is C1-C20, Most preferably, it is C1-C10, for example, fluoromethyl, difluoromethyl, trifluoromethyl, 1- Fluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 1,2-difluoroethyl, 2,2-difluoroethyl, 1,1,2-trifluoroethyl, 1,2,2-trifluoroethyl, 2 , 2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, 1,2,2,2-tetrafluoroethyl, 1,1,2,2,2-pentafluoroethyl, 1-fluoro -1-propyl, 2-fluoro-1-propyl, 3-fluoro-1-propyl, 1,1-difluoro-1-propyl, 1,2-difluoro-1-pro 1,3-difluoro-1-propyl, 2,2-difluoro-1-propyl, 2,3-difluoro-1-propyl, 3,3-difluoro-1-propyl, 1,1,2-trifluoro -1-propyl, 1,1,3-trifluoro-1-propyl, 1,2,2-trifluoro-1-propyl, 1,2,3-trifluoro-1-propyl, 1,3,3- Trifluoro-1-propyl, 2,2,3-trifluoro-1-propyl, 2,3,3-trifluoro-1-propyl, 3,3,3-trifluoro-1-propyl, 1-fluoro- 2-propyl, 2-fluoro-2-propyl, 1,1-difluoro-2-propyl, 1,2-difluoro-2-propyl, 1,3-difluoro-2-propyl, 1,1,1-trifluoro 2-propyl, 1,1 2-trifluoro-2-propyl, 1,1,3-trifluoro-2-propyl, 1,2,3-trifluoro-2-propyl, 1-fluorocyclohexyl, 2-fluorocyclohexyl, 3-fluorocyclohexyl, 4-fluorocyclohexyl, 1,2-difluorocyclohexyl, 1,3-difluorocyclohexyl, 1,4-difluorocyclohexyl, 2,2-difluorocyclohexyl, 2,3-difluorocyclohexyl, 2,4-difluorocyclohexyl, 2,5 -Difluorocyclohexyl, 2,6-difluorocyclohexyl, 3,3-difluorocyclohexyl, 3,4-difluorocyclohexyl, 3,5-difluorocyclohexyl, 3,6-difluorocyclohexyl, 4.4-difluorocyclohexyl, 4,5-difluorocyclohexyl, 4,6-difluorocyclohexyl and the like can be mentioned.

  The fluoroalkenyl group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. For example, 1-fluorovinyl, 2-fluorovinyl, 1,2 -Difluorovinyl, 2,2-difluorovinyl, 1,2,2-trifluorovinyl, 1-fluoroallyl, 2-fluoroallyl, 3-fluoroallyl, 1,1-difluoroallyl, 1,2-difluoroallyl, 1,3-difluoroallyl, 2,3-difluoroallyl, 3,3-difluoroallyl, 1,1,2-trifluoroallyl, 1,1,3-trifluoroallyl, 1,2,3-trifluoroallyl 1,3,3-trifluoroallyl, 1-fluoro-1-propenyl, 2-fluoro-1-propenyl, 3-fluoro-1-propenyl, , 2-difluoro-1-propenyl, 1,3-difluoro-1-propenyl, 2,3-difluoro-1-propenyl, 3,3, -difluoro-1-propenyl, 1,2,3-trifluoro-1 -Propenyl, 3,3,3-trifluoro-1-propenyl, 1,2,3,3-tetrafluoro-1-propenyl, 1,3,3,3-tetrafluoro-1-propenyl, 2,3, 3,3-tetrafluoro-1-propenyl, 1,2,3,3,3-pentafluoro-1-propenyl, 1-fluoro-1-isopropenyl, 3-fluoro-1-isopropenyl, 1,3- Difluoro-1-isopropenyl, 3,3-difluoro-1-isopropenyl, 1,1,3-trifluoro-1-isopropenyl, 3,3,3-trifluoro-1-isopropenyl, 1,3,3-tetrafluoro-1-isopropenyl, 1,3,3,3-tetrafluoro-1-isopropenyl, 1,1,3,3,3-pentafluoro-1-isopropenyl, etc. Can be mentioned.

  In the present invention, the fluoroallyl group refers to a substituent in which one fluorine atom is bonded to any carbon of the allyl group. For example, a partial structure of the following general formula (5) is a 1-fluoroallyl group, a partial structure of the general formula (6) is a 2-fluoroallyl group, a partial structure of the general formula (7) is a 3-fluoroallyl group, and fluorine Those in which two atoms are introduced are called difluoroallyl groups, and those in which three atoms are introduced are called trifluoroallyl groups.

  In the present invention, the fluorovinyl group refers to a substituent in which one fluorine atom is bonded to any carbon of the vinyl group. For example, a partial structure of the following general formula (8) is a 1-fluoroallyl group, a partial structure of the general formula (9) is a 2-fluoroallyl group, and two fluorine atoms introduced are difluorovinyl groups, The introduced one is called a trifluorovinyl group.

  The fluoroalkynyl group preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, and particularly preferably 3 to 10 carbon atoms. For example, 1-fluoropropargyl, 3-fluoropropargyl, 1,1 -Difluoropropargyl, 1,3-difluoropropargyl, 1,1,3-trifluoropropargyl and the like can be mentioned.

  The fluoroaryl group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 10 carbon atoms. For example, 2-fluorophenyl, 3-fluorophenyl, 4-fluoro Phenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 3,6-difluorophenyl 2,3,4-trifluorophenyl, 2,3,5-trifluorophenyl, 2,3,6-trifluorophenyl, 2,4,5-trifluorophenyl, 2,4,6-trifluorophenyl 2,5,6-trifluorophenyl, 3,4,5-trifluorophenyl, 3,4,6-trifluorophenyl, , 5,6-trifluorophenyl, 2,3,4,5-tetrafluorophenyl, 2,3,4,6-tetrafluorophenyl, 2,3,5,6-tetrafluorophenyl, 2,3,4 , 5,6-pentafluorophenyl and the like.

The substituent for R ¹ , R ² and R ³ containing a fluorine atom is preferably a fluorine atom, a fluoroalkyl group, a fluoroalkenyl group, a fluoroalkynyl group or a fluoroaryl group, more preferably a fluorine atom or a fluoroalkyl group. , A fluoroalkenyl group and a fluoroaryl group, more preferably a fluorine atom, a fluoroalkyl group and a fluoroaryl group.

As the fluoroalkyl group for R ¹ , R ² , and R ^3, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 1,1-difluoroethyl group, 1,2-difluoroethyl group, 2,2-difluoroethyl group, 1,1,2-trifluoroethyl group, 1,2,2-trifluoroethyl group, 2,2,2-trifluoroethyl group More preferably, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 1,1,2-trifluoroethyl group, a 1,2,2-trifluoroethyl group, or a 2,2,2-trifluoroethyl group And particularly preferred are a fluoromethyl group, a difluoromethyl group, and a trifluoromethyl group.

The fluoroalkenyl group for R ¹ , R ² and R ³ is preferably 1-fluorovinyl, 2-fluorovinyl, 1,2-difluorovinyl, 2,2-difluorovinyl, 1,2,2-trifluorovinyl, 1 -Fluoroallyl, 2-fluoroallyl, 3-fluoroallyl, 1,1-difluoroallyl, 1,2-difluoroallyl, 1,3-difluoroallyl, 2,3-difluoroallyl, 3,3-difluoroallyl, , 1,2-trifluoroallyl, 1,1,3-trifluoroallyl, 1,2,3-trifluoroallyl, 1,3,3-trifluoroallyl, 1-fluoro-1-propenyl, 2-fluoro -1-propenyl, 3-fluoro-1-propenyl, 1,2-difluoro-1-propenyl, 1,3-difluoro-1-propenyl, 2, -Difluoro-1-propenyl, 3,3-difluoro-1-propenyl, 1,2,3-trifluoro-1-propenyl, 3,3,3-trifluoro-1-propenyl, more preferably 1- Fluorovinyl, 2-fluorovinyl, 1,2-difluorovinyl, 2,2-difluorovinyl, 1-fluoroallyl, 2-fluoroallyl, 3-fluoroallyl, 1,1-difluoroallyl, 1,2-difluoroallyl 1,3-difluoroallyl, 2,3-difluoroallyl, 3,3-difluoroallyl, 1-fluoro-1-propenyl, 2-fluoro-1-propenyl, 3-fluoro-1-propenyl, 1,2- Difluoro-1-propenyl, 1,3-difluoro-1-propenyl, 2,3-difluoro-1-propenyl, 3,3-difluor R-1-propenyl, more preferably 1-fluorovinyl, 2-fluorovinyl, 1-fluoroallyl, 2-fluoroallyl, 1-fluoro-1-propenyl, 2-fluoro-1-propenyl, 3-fluoro -1-propenyl, particularly preferably 1-fluorovinyl and 2-fluoroallyl.

The fluoroalkynyl group for R ¹ , R ² and R ³ is preferably 1-fluoropropargyl, 3-fluoropropargyl, 1,1-difluoropropargyl, 1,3-difluoropropargyl, 1,1,3-trifluoropropargyl. More preferred are 1-fluoropropargyl and 3-fluoropropargyl, and particularly preferred is 3-fluoropropargyl.

The fluoroaryl group for R ¹ , R ² and R ³ is preferably 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl. 2,6-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 3,6-difluorophenyl, 2,3,4-trifluorophenyl, 2,3,5-trifluorophenyl, 2, , 3,6-trifluorophenyl, 2,4,5-trifluorophenyl, 2,4,6-trifluorophenyl, 2,5,6-trifluorophenyl, 3,4,5-trifluorophenyl, 3, , 4,6-trifluorophenyl, 3,5,6-trifluorophenyl, more preferably 2-fluorophenyl, -Fluorophenyl, 4-fluorophenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl 3,6-difluorophenyl, more preferably -fluorophenyl, 3-fluorophenyl, and 4-fluorophenyl, and particularly preferably 4-fluorophenyl.

R ¹ containing no fluorine ^atom, R ^2, is not particularly limited as substituents of R ^3, for example, a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an amino group, an alkoxy group, an aryl Oxy group, heterocyclic group, heterocyclic oxy group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylthio group, hydroxy group, amino group, halogen atom, acyl group, acyloxy group, acylamino group, alkoxycarbonylamino group, Aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group, arylthio group, heteroarylthio group, sulfonyl group, sulfinyl group, ureido group, phosphoric acid amide group, mercapto group, halogen atom, cyano group, Sulfo , Carboxyl group, a nitro group, a hydroxamic acid group, sulfino group, a hydrazino group, an imino group, a silyl group, and a silyloxy group. The preferred range of the substituents represented by R1, R2, and R3 is the same as the substituents represented by R4 and R5.

R ¹ , R ² and R ³ not containing a fluorine atom are preferably a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an aryloxy group, an alkoxy group, a hydroxy group, an amino group, a heterocyclic group, A silyl group, more preferably a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an aryloxy group, an alkoxy group, and a silyl group, still more preferably a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, An alkoxy group and a silyl group are preferable, and a hydrogen atom, an alkyl group, and an aryl group are particularly preferable.

As the alkyl group for R ¹ , R ² , and R ³ , a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, and a tert-butyl group are preferable, and a methyl group, an ethyl group, and a tert-butyl group are preferable. A butyl group is more preferable, and a methyl group is particularly preferable.

Further, as the alkenyl group for R ¹ , R ² , and R ³ , a vinyl group, an allyl group, a 1-propenyl group, a 1-isopropenyl group, a 1-butenyl group, a 2-butenyl group, and a 3-pentenyl group are preferable. A vinyl group, an allyl group, and a 1-propenyl group are more preferable, and an allyl group is particularly preferable.

Moreover, as an alkynyl group of R < ¹ >, R < ² >, R < ³ >, a propargyl group and a butynyl group are preferable, and a propargyl group is more preferable.

Moreover, as an aryl group of R < ¹ >, R < ² >, R < ³ >, a phenyl group, o-methylphenyl group, m-methylphenyl group, p-methylphenyl group, naphthyl group, anthranyl group, and imidazolyl group are preferable, and a phenyl group O-methylphenyl group, m-methylphenyl group and p-methylphenyl group are more preferable, and phenyl group is particularly preferable.

^The aryl group of ^{R 1, R 2, R 3} , a phenyl group, 1-naphthyloxy group, preferably a 2-naphthyloxy group, a phenyl group is more preferable.

As the alkoxy group ^{R 1, R 2, R 3} , a methoxy group, an ethoxy group, a butoxy group, a propoxy group, preferably a 2-ethylhexyloxy group, a methoxy group, more preferably an ethoxy group, a methoxy group, especially preferable.

The amino group of R ¹ , R ² , and R ³ is preferably an amino group, a methylamino group, a dimethylamino group, a diethylamino group, a dibenzylamino group, a diphenylamino group, or a ditolylamino group, and an amino group or a methylamino group A dimethylamino group is more preferable, and a dimethylamino group is particularly preferable.

The heterocyclic groups of R ¹ , R ² and R ³ include imidazolyl group, pyridyl group, quinolyl group, furyl group, thienyl group, piperidyl group, morpholino group, benzoxazolyl group, benzimidazolyl group, and benzthiazolyl group. Carbazolyl group is preferable, imidazolyl group, pyridyl group, furyl group, benzoxazolyl group, benzimidazolyl group, benzthiazolyl group, carbazolyl group is more preferable, imidazolyl group, pyridyl group, furyl group, carbazolyl group is more preferable, imidazolyl group A group, pyridyl group and furyl group are particularly preferred.

The silyl group of R ¹ , R ² and R ³ is preferably a trimethylsilyl group, a triethylsilyl group, a triisopropylsilyl group, a tert-butyldimethylsilyl group, a tert-butyldiphenylsilyl group or a triphenylsilyl group. Group, triethylsilyl group and triphenylsilyl group are more preferable, trimethylsilyl group and triethylsilyl group are more preferable, and trimethylsilyl group is particularly preferable.

When R ¹ is a substituent containing a fluorine atom, the number of fluorine atoms on R ¹ is 1 to 10, preferably 1 to 6, and more preferably 1 to 3.

When R ² is a substituent containing a fluorine atom, the number of fluorine atoms on R ² is 1 to 10, preferably 1 to 6, and more preferably 1 to 3.

When R ³ is a substituent containing a fluorine atom, the number of fluorine atoms on R ³ is 1 to 10, preferably 1 to 6, and more preferably 1 to 3.

Among the substituents of R ¹ , R ² , and R ³ , at least one substituent includes at least one fluorine atom. The number of all fluorine atoms contained in the substituents of R ¹ , R ² and R ³ is 1 to 30, preferably 1 to 10, more preferably 1 to 6, still more preferably 1 to 5, 3 is particularly preferred and 1-2 is most preferred.

R ^{1, R} 2, as the combination of ^{R 3} is not particularly limited, for example, the combination shown in (10-1) to (10-44) in the table below 1,2.

The combination of R ¹ , R ² and R ³ is preferably a combination shown in (10-1) to (10-38) in Tables 1 and 2, and more preferably (10-1) to (10-26). The combination shown in (10-1) to (10-11) is more preferable.

  The compound of the present invention can be synthesized by various methods. For example, a ligand having ring A and ring B and a halogen ion coordinated to iridium is used as a raw material, and an acetylacetone derivative having at least one fluorine atom is allowed to act on the compound in the presence of a base. It can be obtained by carrying out an exchange reaction. As the reaction solvent for synthesizing the metal complex of the present invention, ether solvents, alcohol solvents, and halogen solvents are preferable, tetrahydrofuran, 2-ethoxyethanol, 2-methoxyethanol, 2-propanol, ethanol, dichloromethane, chloroform. Are more preferable, tetrahydrofuran, 2-ethoxyethanol, and chloroform are more preferable, and 2-ethoxyethanol is particularly preferable. The reaction temperature at the time of synthesis is preferably 0 ° C to 150 ° C, more preferably 25 ° C to 140 ° C, and in the case of a solvent having a temperature of 50 ° C to 120 ° C or a boiling point of less than 50 ° C, a range from 25 ° C to the boiling point of the solvent. Is more preferable, and when it is 60 ° C. to 100 ° C. or a boiling point of less than 60 ° C., a range from 25 ° C. to the boiling point of the solvent is particularly preferable. The reaction time for the synthesis is preferably 20 minutes to 24 hours, more preferably 30 minutes to 12 hours, still more preferably 40 minutes to 6 hours, and 1 hour to 4 hours. Some cases are particularly preferred. The base used in the synthesis may be either an organic base or an inorganic base, preferably a metal alkoxide or carbonate, more preferably sodium methoxide, sodium carbonate or potassium carbonate, and even more preferably sodium carbonate.

  Next, although the compound example of this invention is shown, this invention is not limited to this.

  An example of the partial structure L1 composed of A and B is shown below.

  An example of the structure L2 of the acetylacetonato ligand portion having a fluorine atom is shown below.

  As a specific example of the compound represented by the general formula (1), a combination of the partial structure L1 and the partial structure L2 is shown in the following table.

[Light emitting material for organic electroluminescence device]
The organometallic complex of the present invention can be used as a light emitting material for an organic electroluminescent element.
When the organometallic complex of the present invention is used as a light-emitting material for an organic electroluminescent device, it is preferable because an organic electroluminescent device having better suitability and color can be produced.

[Light-Emitting Layer Containing Light-Emitting Material for Organic Electroluminescent Device]
The present invention also relates to a light emitting layer containing the light emitting material for an organic electroluminescent element of the present invention. The light emitting layer of this invention can be used for an organic electroluminescent element.
The light emitting layer of the present invention preferably further contains at least one of a host material and a hydrocarbon material.
By using the organometallic complex represented by the general formula (1) of the present invention as a material for an organic electroluminescence device, an organic electroluminescence device having more excellent production suitability and color can be obtained. The content of the organic electroluminescent element material in the light emitting layer of the present invention is preferably 1 to 30% by mass, and more preferably 3 to 20% by mass in the light emitting layer.

[Composition Containing Light-Emitting Material for Organic Electroluminescent Device of the Present Invention]
The present invention also relates to a composition containing a compound represented by the light emitting material for an organic electroluminescent element of the present invention.
The content of the organic electroluminescent element material in the composition of the present invention is preferably 1 to 40% by mass, and more preferably 5 to 20% by mass.
Other components that may be contained in the composition of the present invention may be organic or inorganic, and as organic materials, materials described as host materials, fluorescent light-emitting materials, phosphorescent light-emitting materials, and hydrocarbon materials described later can be applied. The host material and the hydrocarbon material are preferable, and the host material and the compound represented by the general formula (VI) are more preferable.
The content of the host material in the composition of the present invention is preferably 50 to 95% by mass, and more preferably 70 to 90% by mass.
The composition of the present invention can form an organic layer of an organic electroluminescent element by a dry film forming method such as a vapor deposition method or a sputtering method, a transfer method, a printing method, or the like.

[Organic electroluminescence device]
The device of the present invention will be described in detail.
An organic electroluminescent element of the present invention is an organic electroluminescent element having a pair of electrodes and at least one organic layer including a light emitting layer between the electrodes on a substrate, and is formed on any one of the organic layers. The compound represented by General formula (1) is contained. It is preferable to further have a layer containing the compound represented by the general formula (1) between the light emitting layer and the cathode.

In the organic electroluminescent element of the present invention, the light-emitting layer and the layer containing the compound represented by the general formula (1) are organic layers, and may further have a plurality of organic layers.
In view of the properties of the light emitting element, at least one of the anode and the cathode is preferably transparent or translucent.
FIG. 1 shows an example of the configuration of an organic electroluminescent device according to the present invention. In the organic electroluminescent device 10 according to the present invention shown in FIG. 1, a light emitting layer 6 is sandwiched between an anode 4 and a cathode 9 on a support substrate 12. Specifically, the hole injection layer 4, the hole transport layer 5, the light emitting layer 6, the hole block layer 7, and the electron transport layer 8 are laminated in this order between the anode 4 and the cathode 9.

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

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

<Board>
The substrate used in the present invention is preferably a substrate that does not scatter or attenuate light emitted from the organic layer. In the case of an organic material, it is preferable that it is excellent in heat resistance, dimensional stability, solvent resistance, electrical insulation, and workability.
<Anode>
The anode usually only needs to have a function as an electrode for supplying holes to the organic layer, and there is no particular limitation on the shape, structure, size, etc., depending on the use and purpose of the light-emitting element, It can select suitably from well-known electrode materials. As described above, the anode is usually provided as a transparent anode.
<Cathode>
The cathode usually has a function as an electrode for injecting electrons into the organic layer, and there is no particular limitation on the shape, structure, size, etc., and it is known depending on the use and purpose of the light-emitting element. The electrode material can be selected as appropriate.

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

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

-Formation of organic layer-
In the organic electroluminescent element of the present invention, each organic layer can be suitably formed by any of a dry film forming method such as a vapor deposition method and a sputtering method, a transfer method, and a printing method.

(Light emitting layer)
<Light emitting material>
The light emitting material in the present invention is preferably a compound represented by the general formula (1).

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

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

The light emitting layer in the element of the present invention may be composed of only a light emitting material, or 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 the dopant may be one kind or two or more kinds. The host material is preferably a charge transport material. The host material may be one kind or two or more kinds, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed. Further, the light emitting layer may include a material that does not have charge transporting properties and does not emit light. As the light emitting layer in the element of the present invention, a material using a host material and a compound represented by the general formula (1) as the light emitting material is preferable.
The light emitting layer may be a single layer or a multilayer of two or more layers. When there are a plurality of light emitting layers, the compound represented by the general formula (1) may be contained in two or more light emitting layers. In addition, each light emitting layer may emit light with different emission colors.

<Host material>
The host material used in the present invention may contain the following compounds. For example, pyrrole, indole, carbazole, CBP (4,4′-di (9-carbazoyl) biphenyl), azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole, imidazole, thiophene, polyarylalkane, pyrazoline, Pyrazolone, phenylenediamine, arylamine, amino substituted chalcone, styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatic tertiary amine compound, styrylamine compound, porphyrin compound, polysilane compound, poly (N-vinylcarbazole) , Aniline copolymer, thiophene oligomer, conductive polymer oligomer such as polythiophene, organic silane, carbon film, pyridine, pyrimidine, triazine, imidazole, Razole, triazole, oxazole, oxadiazol, fluorenone, anthraquinodimethane, anthrone, diphenylquinone, thiopyran dioxide, carbodiimide, fluorenylidenemethane, distyrylpyrazine, fluorine-substituted aromatic compound, naphthaleneperylene Metal complexes of heterocyclic tetracarboxylic anhydrides such as phthalocyanines, 8-quinolinol derivatives, metal phthalocyanines, metal complexes having benzoxazole or benzothiazole as ligands, and their Derivatives (which may have a substituent or a condensed ring) can be exemplified.

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

  Further, the content of the host compound in the present invention is not particularly limited, but from the viewpoint of light emission efficiency and driving voltage, it is 15% by mass or more and 99% by mass or less with respect to the total compound mass forming the light emitting layer. Preferably there is.

(Fluorescent material)
Examples of fluorescent light-emitting materials that can be used in the present invention include, for example, benzoxazole derivatives, benzimidazole derivatives, benzothiazole derivatives, styrylbenzene derivatives, polyphenyl derivatives, diphenylbutadiene derivatives, tetraphenylbutadiene derivatives, naphthalimide derivatives, coumarin derivatives. , Condensed aromatic compounds, perinone derivatives, oxadiazole derivatives, oxazine derivatives, aldazine derivatives, pyralidine derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives, quinacridone derivatives, pyrrolopyridine derivatives, thiadiazolopyridine derivatives, cyclopentadiene derivatives, styryl Complexes of amine derivatives, diketopyrrolopyrrole derivatives, aromatic dimethylidin compounds, 8-quinolinol derivatives and pyromethene derivatives Various complexes represented, polythiophene, polyphenylene, polyphenylene vinylene polymer compounds include compounds such as organic silane derivatives.

(Phosphorescent material)
Examples of the phosphorescent material that can be used in the present invention include, in addition to the compound represented by the general formula (1), for example, US6303238B1, US6097147, WO00 / 57676, WO00 / 70655, WO01 / 08230, WO01 / 39234A2, WO01 / 41512A1, WO02 / 02714A2, WO02 / 15645A1, WO02 / 44189A1, WO05 / 19373A2, JP2001-247859, JP2002-302671, JP2002-117978, JP2003-133074, JP2002-235076, JP2003 123982, JP2002-170684, EP121257, JP2002-226495, JP2002-234894, JP2001247478, JP2001-29 470, JP 2002-173675, JP 2002-203678, JP 2002-203679, JP 2004-357799, JP 2006-256999, JP 2007-19462, JP 2007-84635, JP 2007-96259, etc. The phosphorescent light emitting compounds described in the above patent documents are mentioned. Among them, more preferable luminescent dopants include Ir complex, Pt complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex. Eu complex, Tb complex, Gd complex, Dy complex, and Ce complex. Particularly preferred is an Ir complex, a Pt complex, or a Re complex, among which an Ir complex or a Pt complex containing at least one coordination mode of a metal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond, and a metal-sulfur bond. Or Re complexes are preferred. Furthermore, from the viewpoints of luminous efficiency, driving durability, chromaticity, etc., an Ir complex, a Pt complex, or a Re complex containing a tridentate or higher polydentate ligand is particularly preferable.

  The content of the phosphorescent light emitting material is preferably in the range of 0.1% by mass to 50% by mass and more preferably in the range of 0.2% by mass to 50% by mass with respect to the total mass of the light emitting layer in the light emitting layer. More preferably, the range is 0.3% by mass or more and 40% by mass or less, and the most preferable range is 20% by mass or more and 30% by mass or less.

The content of the phosphorescent material (the compound represented by the general formula (1) and / or the phosphorescent material used in combination) that can be used in the present invention is 0.1% by mass or more based on the total mass of the light emitting layer. A range of 50% by mass or less is preferable, a range of 1% by mass or more and 40% by mass or less is more preferable, and a range of 5% by mass or more and 30% by mass or less is most preferable. In particular, in the range of 5% by mass or more and 30% by mass or less, the chromaticity of light emission of the organic electroluminescent element is less dependent on the addition concentration of the phosphorescent light emitting material.
The organic electroluminescent element of the present invention most preferably contains 5 to 30% by mass of at least one of the above light emitting materials (compound represented by the general formula (1)) with respect to the total mass of the light emitting layer.

The organic electroluminescent element preferably further contains a hydrocarbon compound, and more preferably contains a hydrocarbon compound in the light emitting layer.
The hydrocarbon compound is preferably a compound represented by the following general formula (VI).
By appropriately using the compound represented by the general formula (VI) together with the light emitting material, the interaction between the material molecules is appropriately controlled, and the energy gap interaction between adjacent molecules is made uniform to further increase the driving voltage. It can be reduced.
Further, the compound represented by the general formula (VI) used in the organic electroluminescence device is excellent in chemical stability, has little alteration such as decomposition of the material during device driving, and is caused by a decomposition product of the material. It is possible to prevent a decrease in the efficiency of the organic electroluminescence device and a decrease in the device life.
The compound represented by the general formula (VI) will be described.

In the general formula _{(VI), R 4, R} 6, R 8, R 10, X 4 ~X 15 each independently represent a hydrogen atom, an alkyl group or an aryl group.

The alkyl group represented by R ₄ , R ₆ , R ₈ , R ₁₀ , X _{4 to} X ₁₅ in the general formula (VI) may be substituted with an adamantane structure or an aryl structure, and has 1 to 70 carbon atoms. Is preferred, C 1-50 is more preferred, C 1-30 is more preferred, C 1-10 is even more preferred, C 1-6 is particularly preferred, and C 2-6 linear alkyl. The group is most preferred.

Examples of the alkyl group represented by R ₄ , R ₆ , R ₈ , R ₁₀ , X _{4 to} X ₁₅ in the general formula (VI) include an nC ₅₀ H ₁₀₁ group and an nC ₃₀ H ₆₁ group. 3- (3,5,7-triphenyladamantan-1-yl) propyl group (31 carbon atoms), trityl group (19 carbon atoms), 3- (adamantan-1-yl) propyl group (13 carbon atoms) , 9-decalyl group (10 carbon atoms), benzyl group (7 carbon atoms), cyclohexyl group (6 carbon atoms), n-hexyl group (6 carbon atoms), n-pentyl group (5 carbon atoms), n-butyl Examples include a group (4 carbon atoms), an n-propyl group (3 carbon atoms), a cyclopropyl group (3 carbon atoms), an ethyl group (2 carbon atoms), a methyl group (1 carbon atom), and the like.

The aryl group represented by R ₄ , R ₆ , R ₈ , R ₁₀ , X _{4 to} X ₁₅ in the general formula (VI) may be substituted with an adamantane structure or an alkyl structure, and has 6 to 30 carbon atoms. Is preferable, carbon number 6-20 is more preferable, carbon number 6-15 is still more preferable, carbon number 6-10 is especially preferable, and carbon number 6 is the most preferable.

Examples of the aryl group represented by R ₄ , R ₆ , R ₈ , R ₁₀ , X _{4 to} X ₁₅ in the general formula (VI) include, for example, a 1-pyrenyl group (16 carbon atoms), a 9-anthracenyl group ( Carbon number 14), 1-naphthyl group (carbon number 10), 2-naphthyl group (carbon number 10), pt-butylphenyl group (carbon number 10), 2-m-xylyl group (carbon number 8), 5-m-xylyl group (carbon number 8), o-tolyl group (carbon number 7), m-tolyl group (carbon number 7), p-tolyl group (carbon number 7), phenyl group (carbon number 6), etc. Is mentioned.

R ₄ , R ₆ , R ₈ and R ₁₀ in the general formula (VI) may be a hydrogen atom, an alkyl group or an aryl group, but the above-mentioned high glass transition temperature is preferable. From the viewpoint, at least one is preferably an aryl group, more preferably at least two are aryl groups, and particularly preferably 3 to 4 are aryl groups.

X _{4 to} X _{15 in} the general formula (VI) may be a hydrogen atom, an alkyl group, or an aryl group, but are preferably a hydrogen atom or an aryl group, Particularly preferred is an atom.

  The molecular weight of the compound represented by the general formula (VI) in the present invention is 2000 or less from the viewpoint of vapor deposition suitability and solubility since an organic electroluminescent device is prepared using a vacuum vapor deposition process or a solution coating process. Is preferable, 1200 or less is more preferable, and 1000 or less is particularly preferable. Further, from the viewpoint of vapor deposition suitability, if the molecular weight is too small, the vapor pressure becomes small, the change from the gas phase to the solid phase does not occur, and it is difficult to form an organic layer. Is more preferable, and 400 or more is particularly preferable.

The compound represented by the general formula (VI) is preferably solid at room temperature (25 ° C), more preferably solid at room temperature (25 ° C) to 40 ° C, and from room temperature (25 ° C). Particularly preferred is a solid in the range of 60 ° C.
When the compound represented by the general formula (VI) that does not form a solid at room temperature (25 ° C.) is used, a solid phase can be formed at room temperature by combining with other materials.

  The use of the compound represented by the general formula (VI) is not limited and may be contained in any layer in the organic layer. As the introduction layer of the compound represented by the general formula (VI) in the present invention, a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, and a charge block layer described later are used. Preferably, it is contained in one or more of the above, more preferably contained in one or more of the light emitting layer, hole injection layer, hole transport layer, electron transport layer, electron injection layer, and light emission. It is particularly preferred to be contained in any one or more of the layer, the hole injection layer and the hole transport layer, and most preferred to be contained in the light emitting layer.

When the compound represented by the general formula (VI) is used in the organic layer, the content of the compound represented by the general formula (VI) needs to be limited to an amount that does not suppress the charge transport property. Yes, the compound represented by the general formula (VI) is preferably contained in an amount of 0.1 to 70% by mass, more preferably 0.1 to 30% by mass, and 0.1 to 25% by mass. Is particularly preferred.
Moreover, when using the compound represented by general formula (VI) for a some organic layer, it is preferable to contain in said layer in each layer.

  The compound represented by the general formula (VI) may contain only one kind in any organic layer, and contains a combination of a plurality of compounds represented by the general formula (VI) in any ratio. You may do it.

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

The compound represented by the general formula (VI) can be synthesized by appropriately combining adamantane or a halogenated adamantane with an alkyl halide or an alkylmagnesium halide (Grignard reagent). For example, a halogenated adamantane and an alkyl halide can be coupled using indium (Reference 1). Alternatively, alkyl halides can be converted to alkyl copper reagents and coupled with aromatic Grignard reagents (Reference 2). Alkyl halides can also be coupled using an appropriate aryl boric acid and a palladium catalyst (Reference 3).
Reference 1: Tetrahedron Lett. 39, 1998, 9557-9558.
Reference 2: Tetrahedron Lett. 39, 1998, 2095-2096.
Reference 3: J.M. Am. Chem. Soc. 124, 2002, 13662-13663.

  An adamantane skeleton having an aryl group can be synthesized by appropriately combining adamantane or a halogenated adamantane with the corresponding arene or aryl halide.

  In the production methods shown above, when the defined substituents change under the conditions of a certain synthesis method or are inappropriate for carrying out the method, the functional groups are protected and deprotected (for example, , Protective Groups in Organic Synthesis, by TW Greene, John Wiley & Sons Inc. (1981), etc. ) And the like. Moreover, it is also possible to change the order of reaction steps such as introduction of substituents as necessary.

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

-Hole injection layer, hole transport layer-
The hole injection layer and the hole transport layer are layers having a function of receiving holes from the anode or the anode side and transporting them to the cathode side.
-Electron injection layer, electron transport layer-
The electron injection layer and the electron transport layer are layers having a function of receiving electrons from the cathode or the cathode side and transporting them to the anode side.
Regarding the hole injection layer, the hole transport layer, the electron injection layer, and the electron transport layer, the matters described in paragraph numbers [0165] to [0167] of JP-A-2008-270736 can be applied to the present invention. .

-Hole blocking layer-
The hole blocking layer is a layer having a function of preventing holes transported from the anode side to the light emitting layer from passing through to the cathode side. In the present invention, a hole blocking layer can be provided as an organic layer adjacent to the light emitting layer on the cathode side.
As an example of the organic compound constituting the hole blocking layer, aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate (Aluminum (III) bis (2-methyl-8-quinolinato) 4- aluminum complexes such as phenylphenolate (abbreviated as BAlq), triazole derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (2,9-Dimethyl-4,7-diphenyl-1,10-) phenanthroline derivatives such as phenanthroline (abbreviated as BCP)) and the like.
The thickness of the hole blocking layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and still more preferably 10 nm to 100 nm.
The hole blocking layer may have a single layer structure made of one or more of the materials described above, or may have a multilayer structure made of a plurality of layers having the same composition or different compositions.

-Electronic block layer-
The electron blocking layer is a layer having a function of preventing electrons transported from the cathode side to the light emitting layer from passing through to the anode side. In the present invention, an electron blocking layer can be provided as an organic layer adjacent to the light emitting layer on the anode side.
As an example of the organic compound constituting the electron blocking layer, for example, those mentioned as the hole transport material described above can be applied.
The thickness of the electron blocking layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100 nm.
The electron blocking layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.

<Protective layer>
In the present invention, the entire organic EL element may be protected by a protective layer.
Regarding the protective layer, the matters described in paragraph numbers [0169] to [0170] of JP-A-2008-270736 can be applied to the present invention.

<Sealing container>
The element of this invention may seal the whole element using a sealing container.
Regarding the sealing container, the matters described in paragraph No. [0171] of JP-A-2008-270736 can be applied to the present invention.

[Film formation method]
Furthermore, the present invention also relates to a film forming method for forming a film by sublimation by simultaneously heating a compound used in the same organic layer as the compound represented by the general formula (1).
In film formation, the compound represented by the general formula (1) and the compound used in the same organic layer are preferably mixed, and the composition of the present invention may be used. The content ratio of the compound used in the same organic layer as the compound represented by the general formula (1) is 1% to 45% of the compound used in the same organic layer with respect to the compound represented by the general formula (1). Preferably, it is 1% to 25%.
The heating temperature is preferably 200 ° C to 400 ° C, more preferably 250 ° C to 320 ° C.
The heating time is preferably 0.1 hours to 350 hours, more preferably 0.1 hours to 150 hours.
According to the film forming method of the present invention, there is an advantage that a light emitting layer film having high efficiency, high durability, and little color change at high temperature driving can be easily formed.

(Drive)
The organic electroluminescence device of the present invention emits light by applying a direct current (which may include an alternating current component as necessary) voltage (usually 2 to 15 volts) or a direct current between the anode and the cathode. Can be obtained.
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-A-7-134558, JP-A-8-234658, and JP-A-8-2441047. The driving methods described in each publication, Japanese Patent No. 2784615, US Pat. Nos. 5,828,429 and 6,023,308 can be applied.

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

The external quantum efficiency of the light emitting device of the present invention is preferably 20% or more and 30% or less. The value of the external quantum efficiency should be the maximum value of the external quantum efficiency when the device is driven at 20 ° C., or the value of the external quantum efficiency near 100 to 300 cd / m ² when the device is driven at 20 ° C. Can do.

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

The organic EL element in the present invention may have a resonator structure. For example, a multilayer mirror made of a plurality of laminated films having different refractive indexes, a transparent or translucent electrode, a light emitting layer, and a metal electrode are superimposed on a transparent substrate. The light generated in the light emitting layer resonates repeatedly with the multilayer mirror and the metal electrode as a reflection plate.
In another preferred embodiment, a transparent or translucent electrode and a metal electrode each function as a reflector on a transparent substrate, and light generated in the light emitting layer repeats reflection and resonates between them.
In order to form a resonant structure, the optical path length determined from the effective refractive index of the two reflectors and the refractive index and thickness of each layer between the reflectors is adjusted to an optimum value to obtain the desired resonant wavelength. Is done. The calculation formula in the case of the first embodiment is described in JP-A-9-180883. The calculation formula in the case of the second aspect is described in Japanese Patent Application Laid-Open No. 2004-127795.

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

Next, the light emitting device of the present invention will be described with reference to FIG.
The light emitting device of the present invention uses the organic electroluminescent element.
FIG. 2 is a cross-sectional view schematically showing an example of the light emitting device of the present invention.
The light emitting device 20 in FIG. 2 includes a transparent substrate (supporting substrate) 2, an organic electroluminescent element 10, a sealing container 11, and the like.

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

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

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

  Hereinafter, the present invention will be described in detail based on examples, but the embodiment of the present invention is not limited thereto.

Synthesis Example 1 [Synthesis of Metal Complex A]

After adding 2.0 g of compound (5), 90 ml of CH ₂ Cl ₂ and 1.38 ml of acetylacetone to a 300 ml three-necked flask, add 2.8 g of sodium methoxide 28% methanol solution and heat to reflux with stirring under a nitrogen atmosphere. did. After 2 hours, the reaction solution was cooled to room temperature, water and 2-propanol were added thereto, the mixture was stirred and then filtered, and the resulting crystals were washed with 2-propanol. After cooling to room temperature, the crystal taken out by filtration was washed with hexane and dried to obtain 0.55 g of red crystal metal complex A.

Synthesis Example 2 [Synthesis of Metal Complex B]

After adding 1.0 g of compound (5), 20.6 ml of 2-ethoxyethanol, 0.29 ml of 1,1,1,5,5,5-hexafluoro-2,4-pentanedione to a 100 ml three-necked flask, 719 mg of Na ₂ CO ₃ was added, and the mixture was heated to reflux with stirring under a nitrogen atmosphere. After 8 hours, the reaction solution was cooled to room temperature, and the crystal taken out by filtering this solution was washed with water, 2-propanol and hexane in this order to obtain 1.00 g of red crystals. The crystals were transferred to a 200 ml eggplant flask, and 100 ml of 2-propanol was added thereto, cooked and dried to obtain 0.88 g of red crystals. 0.65 g of this crystal was taken and subjected to short column purification with methylene chloride, and hexane was added to the resulting red solution. The resulting precipitated product was filtered off and dried to obtain 0.46 g of red-brown crystalline metal complex B.

Synthesis Example 3 [Synthesis of Metal Complex C]

After adding 300 mg of compound (5), 6 ml of 2-ethoxyethanol, and 0.17 ml of 1,1,1-trifluoro-2,4-pentanedione to a 100 ml three-necked flask, 215 mg of Na ₂ CO ₃ was added, and a nitrogen atmosphere Heated to reflux with stirring under. After 1.5 hours, the reaction solution was cooled to room temperature, 80 ml of water was added thereto, and the mixture was stirred for 20 minutes. The crystal taken out by filtering this liquid was washed with water, 2-propanol and hexane in this order and dried to obtain 0.22 g of metal complex C.

Synthesis Example 4 [Synthesis of Metal Complex D]

To a 100 ml three-necked flask, 0.8 g of compound (5), 33 ml of 2-ethoxyethanol and 0.58 g of Na ₂ CO ₃ were added, and 1,1,1-trifluoro-5,5-dimethyl-2,4-hexanedione After adding 0.17 ml, the mixture was heated to 50 ° C. with stirring under a nitrogen atmosphere. After 20 minutes, 0.3 ml of 1,1,1-trifluoro-5,5-dimethyl-2,4-hexanedione was further added and stirred for another hour, and then the reaction solution was cooled to room temperature. After adding 65 ml of water to the reaction liquid after cooling and stirring for 3 minutes, this liquid was filtered and the crystal taken out was washed with water, 2-propanol and hexane in this order, dried and the metal complex D was reduced to 0.00. 89 g was obtained.

[Evaluation of deposition suitability]
The temperature at which the weight of the metal complex was reduced to 90% by increasing the temperature by 2 ° C. per minute from 25 ° C. as measured by a differential thermobalance (TG / DTA) under vacuum (initial pressure 0.01 Pa) (T Table 5 shows the residual ratio of the metal complex when no change was observed in the weight loss.

  Metal complexes A to D of the present invention were used as light emitting materials. The structures of the light emitting materials A to D are shown below.

  From the above results, it was shown that the light emitting materials B to D of the present invention sublimate at a lower temperature and can be performed at a lower deposition temperature than the comparative light emitting material A.

[Evaluation of proper sublimation purification]
The synthesized light emitting materials A to D were subjected to sublimation purification under an argon atmosphere (pressure 0.07 Pa). Table 6 shows the percent ratio (sublimation purification yield) of the weight of crystals obtained after sublimation purification to the weight of crystals before sublimation purification.

  From the above results, it was shown that the luminescent materials B to D of the present invention can be purified by sublimation at a higher yield than the comparative luminescent material A, that is, have good sublimation purification suitability.

[Evaluation of luminous characteristics]
When a luminescent material and Compound A are co-deposited on a quartz substrate by a vacuum deposition method so as to have a mass ratio of 2:98, the excitation light of 310 nm is irradiated by an absolute PL quantum yield measuring apparatus manufactured by Hamamatsu Photonics. Table 7 shows the maximum maximum wavelength of the emission spectrum and the quantum yield.
The structure of Compound A is shown below.

  From the above results, it was shown that the light-emitting materials B to D of the present invention have a maximum emission wavelength close to 610 nm, which is preferable for the relative luminous efficiency of red than the comparative light-emitting material A. It has also been shown that the number of fluorine atoms contained in the acetylacetonato ligand is preferably 3 rather than 6 from the viewpoint of quantum yield.

[Evaluation of organic EL element characteristics]
(Production of organic EL element)
A glass substrate having an ITO film of 0.5 mm thickness and 2.5 cm square (manufactured by Geomatek Co., Ltd., surface resistance 10 Ω / □) is placed in a cleaning container, ultrasonically cleaned in 2-propanol, and then subjected to UV-ozone treatment for 30 minutes. Went. The following organic layers were sequentially deposited on the transparent anode (ITO film) by vacuum deposition.
First layer: Compound B: Film thickness 120 nm
Second layer: Compound C: film thickness 10 nm
Third layer: Compound D and luminescent material (mass ratio 85:15): film thickness 30 nm
Fourth layer: Compound D: Film thickness 40 nm
On top of this, 1.0 nm of lithium fluoride and 100 nm of metal aluminum were vapor-deposited in this order to form a cathode.
The obtained laminate is put into a glove box substituted with argon gas without being exposed to the atmosphere, and a stainless steel sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.) are used. Then, an organic EL element was produced.
The vapor deposition rate in the examples of the present invention is 0.2 nm / second unless otherwise specified. The deposition rate was measured using a crystal resonator film forming controller CRTM-9000 manufactured by ULVAC. The film thickness described below is also calculated from a calibration curve created based on the numerical value of CRTM-9000 and the film thickness measured with a Dektak stylus type film thickness meter.
The structures of compounds B, C, and D are shown below.

(Evaluation of organic EL elements)
When a voltage of 10 V was applied to the devices using the metal complexes A, C, and D, red light emission derived from each metal complex was emitted.

  The organic electroluminescent element using the organometallic complex of the present invention can be used for a light emitting device, a display device, and a lighting device. In the case of a light-emitting device, a display device, and a lighting device, the light-emitting element of the present invention can be advantageously used because it is designed to emit red light with excellent color.

DESCRIPTION OF SYMBOLS 2 ... Substrate 3 ... Anode 4 ... Hole injection layer 5 ... Hole transport layer 6 ... Light emitting layer 7 ... Hole block layer 8 ... Electron transport layer 9 ...・ Cathode 10: Organic electroluminescent device (organic EL device)
DESCRIPTION OF SYMBOLS 11 ... Organic layer 12 ... Protective layer 14 ... Adhesive layer 16 ... Sealing container 20 ... Light emitting device 30 ... Light scattering member 30A ... Light incident surface 30B ... Light Emitting surface 32... Fine particle 40.

Claims (12)

Production of an organometallic complex represented by the following general formula (1), comprising a step of reacting a compound represented by the following general formula (10) with a compound represented by the following general formula (11) Method.
(In General Formula (1), A represents an aromatic heterocyclic ring containing a nitrogen atom, B represents an aromatic ring or an aromatic heterocyclic ring. For at least one pair of A and B, A represents a quinoline ring or an isoquinoline ring. And B represents naphthalene, A and B may each have a substituent and may be further condensed, and R ¹ and R ³ each independently represents an alkyl group, an aryl group, or heteroaryl. R ² represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, or a halogen atom, and at least one of R ¹ , R ² , and R ³ is at least one or more. A fluorine atom, provided that when A is a 1-isoquinoline ring, R ² is a hydrogen atom, and ^one of R ¹ and R ³ is a trifluoromethyl group, the other of R ¹ and R ³ is a methyl group But 1- (Not a 3,6-dibromocarbazol-9-yl) decyl group.)
(A and B in the general formula (10) and R ¹ , R ² and R ³ in the general formula (11) are the same as those in A, B, R ¹ , R ² and R ^{3 in} the general formula (1). (X in general formula (10) represents a halogen atom.)   The method for producing an organometallic complex according to claim 1, wherein two A are the same and two B are the same.   The method for producing an organometallic complex according to claim 1, wherein A is a quinoline ring.   The method for producing an organometallic complex according to claim 1, wherein A is a 1-isoquinoline ring.   The method for producing an organometallic complex according to claim 1, wherein A is a 3-isoquinoline ring. The method for producing an organometallic complex according to claim 1 or 2, wherein the partial structure composed of A and B is a structure represented by any of the following formulas L1-1 to L1-9.
The number of fluorine atoms contained in the R ¹ , R ² , R ³ is 1-6,
The manufacturing method of the organometallic complex as described in any one of Claims 1-6. R < ² > is a hydrogen atom, The manufacturing method of the organometallic complex as described in any one of Claims 1-7 characterized by the above-mentioned. The method for producing an organometallic complex according to claim 1, wherein R ¹ is a trifluoromethyl group and R ³ is a methyl group. The method for producing an organometallic complex according to claim 1, wherein the compound represented by the general formula (11) has a structure represented by any of the following:
  The method for producing an organometallic complex according to any one of claims 1 to 10, wherein the reaction is performed in the presence of a base.   The organometallic complex according to any one of claims 1 to 10, wherein the reaction is performed in the presence of a solvent selected from the group consisting of an ether solvent, an alcohol solvent, and a halogen solvent. Manufacturing method.