WO2012014696A1

WO2012014696A1 - ORGANIC ELECTROLUMINESCENT ELEMENT AND COMPOUND HAVING p-DICYANOBENZENE STRUCTURE

Info

Publication number: WO2012014696A1
Application number: PCT/JP2011/066090
Authority: WO
Inventors: 渡辺　徹; 伊勢　俊大; 北村　哲; 玲武田; 康智米久田
Original assignee: 富士フイルム株式会社
Priority date: 2010-07-29
Filing date: 2011-07-14
Publication date: 2012-02-02
Also published as: JP2012033663A; JP5563399B2

Abstract

An organic electroluminescent element with significantly improved durability relative to conventional elements using charge transport materials, and a compound having a p-dicyanobenzene structure and a specific substituent. The organic electroluminescent element comprises, on a substrate, a pair of electrodes consisting of an anode and a cathode, and at least one organic layer including a light-emitting layer positioned between the electrodes, wherein at least one of the organic layers contains at least one kind of compound having a p-dicyanobenzene structure and a specific substituent.

Description

Organic electroluminescence device and compound having p-dicyanobenzene structure

The present invention relates to an organic electroluminescent device and a compound having a p-dicyanobenzene structure.

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

In recent years, the use of phosphorescent light emitting materials has led to higher efficiency of devices. Patent Document 1 discloses an element using a benzonitrile-based charge transport material having a substituent at the ortho position for further improving the light emission efficiency of the element and reducing the driving voltage.
In addition, Patent Document 2 discloses an element using a charge transport material in which two or more condensed polycyclic aromatic groups are substituted for phenylene in order to reduce the driving voltage of the element and improve luminance and durability.
However, devices using these conventional charge transport materials have low durability, and a significant improvement in durability is required.

Japanese Unexamined Patent Publication No. 2007-266598 Japanese Unexamined Patent Publication No. 2002-329580

Devices using conventional charge transport materials have low durability, and a significant improvement in durability has been demanded.
In response to this problem of devices using conventional charge transport materials, the present inventors have greatly improved durability by using a compound having a p-dicyanobenzene structure and a specific substituent. It has been found that an organic electroluminescent device is provided.

That is, an object of the present invention is to provide an organic electroluminescence device having greatly improved durability compared to a device using a conventional charge transport material.
Another object of the present invention is to provide a compound useful for the organic electroluminescence device described above, and a composition and a thin film containing the compound. Furthermore, another object of the present invention is to provide a light emitting device, a display device, and a lighting device including the organic electroluminescent element of the present invention.

According to the study by the present inventors, an organic electroluminescent device having significantly improved durability compared to conventional devices is provided by using a compound having a p-dicyanobenzene structure and a specific substituent. I found out that The compound is useful for producing an organic electroluminescent device having greatly improved durability.

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

[1]
An organic electroluminescent device comprising a substrate and a pair of electrodes comprising an anode and a cathode, and at least one organic layer including a light emitting layer between the electrodes, wherein at least one of the at least one organic layer An organic electroluminescent device comprising at least one compound represented by the following general formula (1).

In the general formula (1), R ¹¹ and R ¹⁵ each independently represent a hydrogen atom or an alkyl group, or R ¹¹ is bonded to R ¹² and R ¹⁵ is bonded to R ¹⁴ to form a substituent C A naphthalene ring, a phenanthrene ring, a triphenylene ring, or a fluorene ring, which may have
R ¹² , R ¹³ and R ¹⁴ are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, a cyano group, a phenyl group which may have a substituent C, or a naphthyl which may have a substituent C. A phenanthrenyl group which may have a group, a substituent C, a triphenylenyl group which may have a substituent C, or a fluorenyl group which may have a substituent C; R ¹² and R ¹³ , and R ¹³ and R ¹⁴ may be bonded to each other to form a naphthalene ring, a phenanthrene ring, a triphenylene ring, or a fluorene ring, which may have a substituent C.
n represents 1, 2 or 3.
When n is 2 or 3, the plurality of R ¹¹ to R ¹⁵ may be the same or different.
Substituent C is an alkyl group, cycloalkyl group, cyano group, phenyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, or fluorenyl group, and substituent C is a phenyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, or In the case of a fluorenyl group, these groups may further have the substituent C.
[2]
The organic electroluminescent element according to the above [1], wherein in the general formula (1), n is 2.
[3]
The organic electroluminescent element according to the above [1] or [2], wherein the compound represented by the general formula (1) is a compound represented by the following general formula (2).

In the general formula (2), R ²¹ , R ²⁵ , R ²⁶ and R ³⁰ each independently represent a hydrogen atom or an alkyl group, or R ²¹ represents R ²² , R ²⁵ represents R ²⁴ , R ²⁶ R ²⁷ and R ³⁰ are each bonded to R ²⁹ to form a naphthalene ring, phenanthrene ring, triphenylene ring or fluorene ring which may have a substituent C.
R ²² , R ²³ , R ²⁴ , R ²⁷ , R ²⁸ and R ²⁹ are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, a cyano group, a phenyl group optionally having substituent C, or a substituent. A naphthyl group optionally having C, a phenanthrenyl group optionally having a substituent C, a triphenylenyl group optionally having a substituent C, or a fluorenyl group optionally having a substituent C Represents. R ²² and R ²³ , R ²³ and R ²⁴ , R ²⁷ and R ²⁸ , and R ²⁸ and R ²⁹ may be bonded to each other and may have a substituent C, a naphthalene ring, a phenanthrene ring, a triphenylene ring Or you may form a fluorene ring.
Substituent C is an alkyl group, cycloalkyl group, cyano group, phenyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, or fluorenyl group, and substituent C is a phenyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, or In the case of a fluorenyl group, these groups may further have the substituent C.
[4]
In the above general formula (2), in the above [3], R ²¹ and R ²⁶ , R ²² and R ²⁷ , R ²³ and R ²⁸ , R ²⁴ and R ²⁹ , and R ²⁵ and R ³⁰ are the same. The organic electroluminescent element as described.
[5]
The organic electroluminescence device according to any one of [1] to [4], wherein the light emitting layer contains at least one phosphorescent material.
[6]
The organic electroluminescent element according to any one of [1] to [5] above, wherein the phosphorescent material is an iridium complex represented by the following general formula (E-1).

In general formula (E-1), Z ¹ and Z ² each independently represent a carbon atom or a nitrogen atom.
A ₁ represents an atomic group that forms a 5- or 6-membered heterocycle with Z ¹ and a nitrogen atom.
B ₁ represents an atomic group that forms a 5- or 6-membered ring with Z ² and a carbon atom.
(XY) represents a monoanionic bidentate ligand.
n _E1 represents an integer of 1 to 3.
[7]
The organic electroluminescence device according to any one of the above [1] to [6], wherein the compound represented by the general formula (1) or (2) is contained in the light emitting layer.
[8]
The organic electroluminescence according to any one of [1] to [7] above, wherein the compound represented by the general formula (1) or (2) is used in a layer between the light emitting layer and the cathode. element.
[9]
A light emitting device using the organic electroluminescent element as described in any one of [1] to [8] above.
[10]
A display device using the organic electroluminescent element according to any one of [1] to [8] above.
[11]
An illumination device using the organic electroluminescent element according to any one of [1] to [8] above.
[12]
A compound represented by the following general formula (1).

In the general formula (1), R ¹¹ and R ¹⁵ each independently represent a hydrogen atom or an alkyl group, or R ¹¹ is bonded to R ¹² and R ¹⁵ is bonded to R ¹⁴ to form a substituent C A naphthalene ring, a phenanthrene ring, a triphenylene ring, or a fluorene ring, which may have
R ¹² , R ¹³ and R ¹⁴ are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, a cyano group, a phenyl group which may have a substituent C, or a naphthyl which may have a substituent C. A phenanthrenyl group which may have a group, a substituent C, a triphenylenyl group which may have a substituent C, or a fluorenyl group which may have a substituent C; R ¹² and R ¹³ , and R ¹³ and R ¹⁴ may be bonded to each other to form a naphthalene ring, a phenanthrene ring, a triphenylene ring, or a fluorene ring, which may have a substituent C.
n represents 1, 2 or 3.
When n is 2 or 3, the plurality of R ¹¹ to R ¹⁵ may be the same or different.
Substituent C is an alkyl group, cycloalkyl group, cyano group, phenyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, or fluorenyl group, and substituent C is a phenyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, or In the case of a fluorenyl group, these groups may further have the substituent C.
[13]
The compound according to [12], wherein in the general formula (1), n is 2.
[14]
The compound according to [12] or [13], which is a compound represented by the following general formula (2).

In the general formula (2), R ²¹ , R ²⁵ , R ²⁶ and R ³⁰ each independently represent a hydrogen atom or an alkyl group, or R ²¹ represents R ²² , R ²⁵ represents R ²⁴ , R ²⁶ R ²⁷ and R ³⁰ are each bonded to R ²⁹ to form a naphthalene ring, phenanthrene ring, triphenylene ring or fluorene ring which may have a substituent C.
R ²² , R ²³ , R ²⁴ , R ²⁷ , R ²⁸ and R ²⁹ are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, a cyano group, a phenyl group optionally having substituent C, or a substituent. A naphthyl group optionally having C, a phenanthrenyl group optionally having a substituent C, a triphenylenyl group optionally having a substituent C, or a fluorenyl group optionally having a substituent C Represents. R ²² and R ²³ , R ²³ and R ²⁴ , R ²⁷ and R ²⁸ , and R ²⁸ and R ²⁹ may be bonded to each other and may have a substituent C, a naphthalene ring, a phenanthrene ring, a triphenylene ring Or you may form a fluorene ring.
Substituent C is an alkyl group, cycloalkyl group, cyano group, phenyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, or fluorenyl group, and substituent C is a phenyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, or In the case of a fluorenyl group, these groups may further have the substituent C.
[15]
In the above general formula (2), in the above [14], R ²¹ and R ²⁶ , R ²² and R ²⁷ , R ²³ and R ²⁸ , R ²⁴ and R ²⁹ , and R ²⁵ and R ³⁰ are the same. The described compound.
[16]
A composition comprising the compound represented by the general formula (1) or (2) according to any one of [12] to [15] above.
[17]
A thin film containing the compound represented by the general formula (1) or (2) according to any one of [12] to [15] above.

According to the present invention, it is possible to provide an organic electroluminescence device having significantly improved durability compared to a conventional device. In addition, according to the present invention, a compound useful for producing an organic electroluminescence device having greatly improved durability can be provided.

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

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

(Substituent group B)
An alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), alkenyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as vinyl , Allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as propargyl , 3-pentynyl, etc.), aryl groups (preferably having 6 to 30 carbon atoms, more preferably carbon 6 to 20, particularly preferably 6 to 12 carbon atoms, such as phenyl, p-methylphenyl, naphthyl, anthracenyl, etc.), cyano group, heterocyclic group (including aromatic heterocyclic group, 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, a sulfur atom, a phosphorus atom, a silicon atom, a selenium atom, and a tellurium atom. Is pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolid Le, benzoimida Ryl, benzothiazolyl, carbazolyl group, azepinyl group, silylyl group, etc.) These substituents may be further substituted, and examples of further substituents include groups selected from the substituent group B. Can do. Moreover, the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group B described above. Moreover, the substituent substituted by the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group B described above.

The organic electroluminescent element of the present invention is an organic electroluminescent element having a pair of electrodes comprising an anode and a cathode and at least one organic layer including a luminescent layer between the electrodes on a substrate, wherein the at least one layer At least one of the organic layers contains at least one compound represented by the following general formula (1).

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

In the general formula (1), R ¹¹ and R ¹⁵ each independently represent a hydrogen atom or an alkyl group, or R ¹¹ is bonded to R ¹² and R ¹⁵ is bonded to R ¹⁴ to form a substituent C A naphthalene ring, a phenanthrene ring, a triphenylene ring, or a fluorene ring, which may have
R ¹² , R ¹³ and R ¹⁴ are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, a cyano group, a phenyl group which may have a substituent C, or a naphthyl which may have a substituent C. A phenanthrenyl group which may have a group, a substituent C, a triphenylenyl group which may have a substituent C, or a fluorenyl group which may have a substituent C; R ¹² and R ¹³ , and R ¹³ and R ¹⁴ may be bonded to each other to form a naphthalene ring, a phenanthrene ring, a triphenylene ring, or a fluorene ring, which may have a substituent C.
n represents 1, 2 or 3.
When n is 2 or 3, the plurality of R ¹¹ to R ¹⁵ may be the same or different.
Substituent C is an alkyl group, cycloalkyl group, cyano group, phenyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, or fluorenyl group, and substituent C is a phenyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, or In the case of a fluorenyl group, these groups may further have the substituent C.

R ¹¹ and R ¹⁵ each independently represent a hydrogen atom or an alkyl group, or R ¹¹ may be bonded to R ¹² and R ¹⁵ may be bonded to R ¹⁴ and may have a substituent C. , A naphthalene ring, a phenanthrene ring, a triphenylene ring or a fluorene ring. Here, the naphthalene ring, phenanthrene ring, triphenylene ring or fluorene ring which may have the substituent C to be formed is a benzene ring substituted by R ¹¹ and R ¹⁵ , and R ¹² and R described later. ¹³ and R ¹³ and R ¹⁴ , when bonded to each other to form a ring, mean the entire structure including the ring formed by them.
The alkyl group represented by R ¹¹ and R ¹⁵ is a linear or branched alkyl group and has no substituent. The alkyl group represented by R ¹¹ and R ¹⁵ is preferably an alkyl group having 1 to 18 carbon atoms, more preferably an alkyl group having 1 to 12 carbon atoms, and still more preferably an alkyl group having 1 to 6 carbon atoms. Particularly preferably a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a t-butyl group, an i-butyl group, an n-pentyl group, a neopentyl group, a t-amyl group. , S-isoamyl group and n-hexyl group, and most preferably any of methyl group, i-propyl group, n-butyl group and t-butyl group.

R ¹¹ and R ¹⁵ each independently represent a hydrogen atom or an alkyl group, or R ¹¹ is bonded to R ¹² and R ¹⁵ is bonded to R ¹⁴ to be substituted with an unsubstituted naphthalene ring or a phenyl group. It is preferable to form a naphthylene ring, an unsubstituted phenanthrene ring, an unsubstituted triphenylene ring, an unsubstituted fluorene ring, or a fluorene ring substituted with a cyclohexyl group, and more preferably R ¹¹ and R ¹⁵ are each Independently, it represents a hydrogen atom, or R ¹¹ is bonded to R ¹² and R ¹⁵ is bonded to R ¹⁴ to form an unsubstituted phenanthrene ring.

R ¹² , R ¹³ and R ¹⁴ are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, a cyano group, a phenyl group which may have a substituent C, or a naphthyl which may have a substituent C. A phenanthrenyl group which may have a group, a substituent C, a triphenylenyl group which may have a substituent C, or a fluorenyl group which may have a substituent C; R ¹² and R ¹³ , and R ¹³ and R ¹⁴ may be bonded to each other to form a naphthalene ring, a phenanthrene ring, a triphenylene ring, or a fluorene ring, which may have a substituent C. Here, the naphthalene ring, phenanthrene ring, triphenylene ring or fluorene ring which may have the substituent C to be formed is a benzene ring substituted by R ¹² , R ¹³ and R ^14, and the aforementioned R ^{When 11} and R ¹² , and R ¹⁵ and R ¹⁴ are bonded to each other to form a ring, it means the entire structure including the ring formed by them.

The alkyl group represented by R ¹² , R ¹³ and R ¹⁴ is a linear or branched alkyl group and has no substituent. The alkyl group represented by R ¹² , R ¹³ and R ¹⁴ is preferably an alkyl group having 1 to 18 carbon atoms, more preferably an alkyl group having 1 to 12 carbon atoms, still more preferably 1 to 1 carbon atom. And particularly preferably a methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, t-butyl group, i-butyl group, n-pentyl group, neopentyl group, t One of -amyl group, s-isoamyl group and n-hexyl group, and most preferably one of methyl group, i-propyl group, n-butyl group and t-butyl group.

The cycloalkyl group represented by R ¹² , R ¹³ and R ¹⁴ has no substituent. The cycloalkyl group represented by R ¹² , R ¹³ and R ¹⁴ is preferably a cycloalkyl group having 3 to 20 carbon atoms, more preferably a cycloalkyl group having 5 to 15 carbon atoms, still more preferably a carbon atom. A cycloalkyl group having a number of 5 to 10, particularly preferably a cyclopentyl group or a cyclohexyl group.

R ¹² , R ¹³ and R ¹⁴ are preferably each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an unsubstituted phenyl group, a phenyl group having a phenyl group, a phenyl group having an alkyl group, or a phenyl having a cyano group. Group, phenyl group having phenanthrenyl group and cyano group, phenyl group having triphenylenyl group and cyano group, phenyl group having biphenyl group substituted by cyano group, phenyl group substituted by phenyl group and phenyl group having cyano group Represents an unsubstituted naphthyl group, an unsubstituted phenanthrenyl group, an unsubstituted triphenylenyl group, a fluorenyl group having an alkyl group, or a fluorenyl group having a terphenyl group substituted with a cyano group, or R ¹² and R ¹³ , And R ¹³ and R ¹⁴ , It has a substituted naphthalene ring, a naphthalene ring having a phenyl group, an unsubstituted phenanthrene ring, a phenanthrene ring having a phenyl group substituted with a cyano group and a phenyl group, an unsubstituted triphenylene ring, an unsubstituted fluorene ring, and an alkyl group A fluorene ring, a fluorene ring having a cycloalkyl group, or a fluorene ring having a phenyl group may be formed.
R ¹² , R ¹³ and R ¹⁴ are more preferably each independently a hydrogen atom, an alkyl group, an unsubstituted phenyl group, a phenyl group having a phenyl group, a phenyl group having a phenanthrenyl group and a cyano group, or an unsubstituted triphenylenyl. R ¹² and R ¹³ , and R ¹³ and R ¹⁴ may be bonded to each other to form an unsubstituted phenanthrene ring, an unsubstituted triphenylene ring, or a fluorene ring having an alkyl group. Good.

n represents 1, 2 or 3, and n is preferably 2 from the viewpoints of manufacturability and device durability. When n is 2, the substitution positions of the two substituents substituted into the p-dicyanobenzene structure included in the general formula (1) are the 2-position and 3-position, the 2-position and 5-position, or the 2-position and 6-position. However, the substitution positions are preferably the 2nd and 5th positions from the viewpoint of the availability of the raw material compounds and the improvement of the durability.
When n is 2, the two substituents substituted on the p-dicyanobenzene structure contained in the general formula (1) are preferably symmetrical.

Substituent C is an alkyl group, cycloalkyl group, cyano group, phenyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, or fluorenyl group, and substituent C is a phenyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, or In the case of a fluorenyl group, these groups may further have the substituent C. Specific examples and preferred ranges of the alkyl group and cycloalkyl group as the substituent C are the same as the specific examples and preferred ranges of the alkyl group and cycloalkyl group represented by the aforementioned R ¹² , R ¹³ and R ¹⁴ .
The substituent C is preferably an alkyl group, a cycloalkyl group, a cyano group, or a phenyl group, and more preferably an alkyl group, a cyano group, or a phenyl group.

The compound represented by the general formula (1) is preferably a compound represented by the following general formula (2) from the viewpoint of improving durability.

In the general formula (2), R ²¹ , R ²⁵ , R ²⁶ and R ³⁰ each independently represent a hydrogen atom or an alkyl group, or R ²¹ represents R ²² , R ²⁵ represents R ²⁴ , R ²⁶ R ²⁷ and R ³⁰ are each bonded to R ²⁹ to form a naphthalene ring, phenanthrene ring, triphenylene ring or fluorene ring which may have a substituent C.
R ²² , R ²³ , R ²⁴ , R ²⁷ , R ²⁸ and R ²⁹ are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, a cyano group, a phenyl group optionally having substituent C, or a substituent. A naphthyl group optionally having C, a phenanthrenyl group optionally having a substituent C, a triphenylenyl group optionally having a substituent C, or a fluorenyl group optionally having a substituent C Represents. R ²² and R ²³ , R ²³ and R ²⁴ , R ²⁷ and R ²⁸ , and R ²⁸ and R ²⁹ may be bonded to each other and may have a substituent C, a naphthalene ring, a phenanthrene ring, a triphenylene ring Or you may form a fluorene ring.
Substituent C is an alkyl group, cycloalkyl group, cyano group, phenyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, or fluorenyl group, and substituent C is a phenyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, or In the case of a fluorenyl group, these groups may further have the substituent C.

In the general formula (2), specific examples and preferred ranges of R ²¹ , R ²⁵ , R ²⁶ and R ³⁰ are the same as the specific examples and preferred ranges of R ¹¹ and R ¹⁵ in the general formula (1).
In the general formula (2), specific examples and preferred ranges of R ²² , R ²³ , R ²⁴ , R ²⁷ , R ²⁸ and R ²⁹ are the specific examples of R ¹² , R ¹³ and R ¹⁴ in the general formula (1). This is the same as the preferred range.

R ²¹ and R ²⁶ , R ²² and R ²⁷ , R ²³ and R ²⁸ , R ²⁴ and R ²⁹ , and R ²⁵ and R ³⁰ are the same from the viewpoint of availability of raw material compounds and ease of synthesis. It is preferable.

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

In the compound represented by the general formula (1) or (2), R ¹¹ and R ¹⁵ , or R ²¹ , R ²⁵ , R ²⁶ and R ³⁰ are a hydrogen atom or an alkyl group, or a specific condensation. It is limited to forming a hydrocarbon structure. When, for example, a phenyl group is substituted at the substitution position of these groups (that is, the ortho position of the benzene ring with respect to the p-dicyanobenzene structure), an orthoterphenyl structure containing the p-dicyanobenzene structure is formed. This orthoterphenyl structure tends to produce a cyclic structure having a low T ₁ component (T ₁ is the lowest excited triplet energy) by the progress of the electrocyclic reaction in an excited state, but there is only one orthoterphenyl structure. When formed, one orthoterphenyl structure does not have a substantial adverse effect on device performance. However, when a plurality of orthoterphenyl structures are formed, the tendency to form a cyclic structure that is a low T ₁ component becomes significant. The low T ₁ component acts as a quencher for the light emitting material and tends to cause a decrease in durability and external quantum efficiency. Therefore, an aryl group such as a phenyl group is suitable as a substituent at the ortho position of the benzene ring relative to the p-dicyanobenzene structure. is not.

Similarly, in the general formula (1) or (2), a compound outside the scope of the present invention in which n is 4 has a plurality of the above-described orthoterphenyl structures, and therefore has a tendency to form a cyclic structure that is a low T ₁ component. It becomes prominent and tends to cause a decrease in durability and external quantum efficiency. Therefore, in the compound represented by the general formula (1) or (2), it is effective from the viewpoint of improving the durability that n is 1, 2 or 3.

In general formula (1) or (2), if there are three or more cyano groups in the same benzene ring, the electron affinity becomes too large, and if the organic EL device emits light, it tends to cause a decrease in external quantum efficiency and an increase in driving voltage. Therefore, it is not preferable.

The molecular weight of the compound represented by the general formula (1) or (2) is usually 350 or more and 1500 or less, preferably 450 or more and 1200 or less, more preferably 500 or more and 1100 or less, and 600 or more and 1000 or less. More preferably. When the molecular weight is 450 or more, it is advantageous for forming a high-quality amorphous thin film, and when the molecular weight is 1200 or less, the solubility and sublimation property are improved, which is advantageous for improving the purity of the compound. *

The compound represented by the general formula (1) or (2) is preferably contained in the light emitting layer or the electron transporting layer because of its high electron affinity and excellent electron injection from the cathode side.

When the compound represented by the general formula (1) or (2) is used as a host material of a light emitting layer of an organic electroluminescence device or a charge transport material of a layer adjacent to the light emitting layer, an energy gap in a thin film state than the light emitting material (When the light-emitting material is a phosphorescent material, a minimum excited triplet (T ₁ ) energy in a thin film state) is advantageous in improving efficiency by preventing quenching of light emission. On the other hand, from the viewpoint of chemical stability of the compound, it is preferable that the energy gap and T ₁ energy are not too large.
The T ₁ energy in the film state of the compound represented by the general formula (1) or (2) is preferably 2.39 eV (55 kcal / mol) or more and 3.51 eV (80 kcal / mol) or less. More preferably, it is 52 eV (58 kcal / mol) or more and 3.25 eV (75 kcal / mol) or less, and further preferably 2.65 eV (61 kcal / mol) or more and 3.04 eV (70 kcal / mol) or less. In particular, when a phosphorescent light emitting material is used as the light emitting material, the T ₁ energy is preferably in the above range.

The T ₁ energy can be obtained from the short wavelength end of a phosphorescence emission spectrum of a thin film of material. For example, a material is deposited on a cleaned quartz glass substrate to a thickness of about 50 nm by vacuum deposition, and the phosphorescence emission spectrum of the thin film is measured at F-7000 Hitachi Spectrofluorimeter (Hitachi High Technologies) under liquid nitrogen temperature. Use to measure. The T ₁ energy can be obtained by converting the rising wavelength on the short wavelength side of the obtained emission spectrum into energy units.

The glass transition temperature (Tg) of the compound represented by the general formula (1) or (2) is 100 ° C. or more from the viewpoint of stably operating the organic electroluminescent device against heat generated during high temperature driving or during device driving. It is preferably 400 ° C. or lower, more preferably 120 ° C. or higher and 400 ° C. or lower, and still more preferably 140 ° C. or higher and 400 ° C. or lower.

When the purity of the compound represented by the general formula (1) or (2) is low, impurities work as a charge transport trap or promote the deterioration of the device. Therefore, in the general formula (1) or (2) The higher the purity of the represented compound, the better. The purity can be measured by, for example, high performance liquid chromatography (HPLC), and the area ratio of the compound represented by the general formula (1) or (2) when detected with a light absorption intensity of 254 nm is preferably 95.0% or more More preferably, it is 97.0% or more, particularly preferably 99.0% or more, and most preferably 99.9% or more.

As known in the carbazole-based material described in WO2008 / 117889, a part or all of the hydrogen atoms of the compound represented by the general formula (1) or (2) are substituted with deuterium atoms. The material is also preferably used as a charge transport material.

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

The compound exemplified as the compound represented by the general formula (1) or (2) can be synthesized with reference to a method described in, for example, JP-A-2007-266598, but is not limited thereto. After the synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.

In the present invention, the use of the compound represented by the general formula (1) or (2) 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 (1) or (2), contained in any one or more of the light emitting layer, the layer between the light emitting layer and the cathode, the layer between the light emitting layer and the anode Preferably, it is contained in one or more of the light emitting layer and the layer between the light emitting layer and the cathode, and more preferably contained in the light emitting layer or the layer between the light emitting layer and the cathode. Is particularly preferred. Specifically, the light-emitting layer, the hole injection layer, the hole transport layer, the electron transport layer, the electron injection layer, the exciton block layer, the charge block layer, or more preferably contained More preferably, it is contained in any one or a plurality of layers and electron transport layers, and particularly preferably contained in the light emitting layer or the electron transport layer.
When the compound represented by the general formula (1) or (2) is contained in the light emitting layer, the compound represented by the general formula (1) or (2) of the present invention is 0 with respect to the total mass of the light emitting layer. The content is preferably 1 to 99% by mass, more preferably 1 to 97% by mass, and still more preferably 10 to 96% by mass. When the compound represented by the general formula (1) or (2) is further contained in a layer other than the light emitting layer, it is preferably contained in an amount of 70 to 100% by mass with respect to the total mass of the layer other than the light emitting layer. More preferably, it is contained in an amount of 85 to 100% by mass.

[Charge Transport Material Represented by General Formula (1)]
The present invention also relates to a charge transport material represented by the general formula (1). The charge transport material represented by the general formula (1) is preferably a charge transport material represented by the general formula (2).
The compound represented by the general formula (1) or (2) and the charge transport material of the present invention are organic materials such as electrophotography, organic transistors, organic photoelectric conversion elements (energy conversion applications, sensor applications, etc.), organic electroluminescence elements, and the like. It can be preferably used for an electronic device, and is particularly preferably used for an organic electroluminescent device.
Among the possible structures of the charge transport material represented by the general formula (1) or (2), the preferred range is as described above.

[Composition containing compound represented by general formula (1) or (2)]
The present invention also relates to a composition comprising the compound represented by the general formula (1) or (2). In the composition of the present invention, the content of the compound represented by the general formula (1) or (2) is preferably 30 to 99% by mass with respect to the total solid content in the composition, preferably 50 to 97 More preferably, it is 70% by mass, and still more preferably 70-96% 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. A host material, a phosphorescent material, and a hydrocarbon material are preferable.
The composition of the present invention can form an organic layer of an organic electroluminescence device by a dry film forming method such as a vapor deposition method or a sputtering method, or a wet film forming method such as a transfer method or a printing method.

[Thin film containing compound represented by general formula (1) or (2)]
The present invention also relates to a thin film containing a compound represented by the general formula (1) or (2). The thin film of the present invention can be formed by using the composition of the present invention by a dry film forming method such as a vapor deposition method or a sputtering method, or a wet film forming method such as a transfer method or a printing method. The thickness of the thin film may be any thickness depending on the application, but is preferably 0.1 nm to 1 mm, more preferably 0.5 nm to 1 μm, still more preferably 1 nm to 200 nm, and particularly preferably 1 nm to 100 nm. is there.

[Organic electroluminescence device]
The organic electroluminescent element of the present invention will be described in detail.
The organic electroluminescent element of the present invention is an organic electroluminescent element having a pair of electrodes comprising an anode and a cathode and at least one organic layer including a luminescent layer between the electrodes on a substrate, wherein the at least one layer At least one of the organic layers contains at least one compound represented by the above general formula (1). In view of the properties of the light-emitting element, at least one of the pair of electrodes, the anode and the cathode, is preferably transparent or translucent.
Examples of the organic layer include a hole injection layer, a hole transport layer, a block layer (such as a hole block layer and an exciton block layer), and an electron transport layer in addition to the light emitting layer. A plurality of these organic layers may be provided, and when a plurality of layers are provided, they may be formed of the same material, or may be formed of different materials for each layer.
In FIG. 1, an example of a structure of the organic electroluminescent element which concerns on this invention is shown. The organic electroluminescent element 10 of FIG. 1 has an organic layer including a light emitting layer 6 between a pair of electrodes (anode 3 and cathode 9) on a substrate 2. As the organic layer, a hole injection layer 4, a hole transport layer 5, a light emitting layer 6, a hole block layer 7 and an electron transport layer 8 are laminated in this order from the anode side 3.

<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 formed on the said transparent electrode or the said semi-transparent electrode. preferable. In this case, the organic layer is formed on the front surface or one surface of the transparent electrode or the semitransparent 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 / electron transport layer / electron injection 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.

<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 of dry film forming methods such as vapor deposition and sputtering, and solution coating methods such as transfer, printing, spin coating, and bar coating. Can be formed. It is preferable that at least one of the organic layers is formed by a solution coating method.

(Light emitting layer)
The light emitting layer receives holes from the anode, hole injection layer or hole transport layer and receives electrons from the cathode, electron injection layer or electron transport layer when an electric field is applied, and provides a field for recombination of holes and electrons. And a layer having a function of emitting light. The light emitting layer in the organic electroluminescent element of the present invention contains at least one kind of fluorescent light emitting material or phosphorescent light emitting material, and preferably contains at least one kind of phosphorescent light emitting material from the viewpoint of improving the external quantum yield.

(Luminescent material)
In the present invention, in addition to at least one type of fluorescent light-emitting material or phosphorescent light-emitting material contained in the light-emitting layer, as the light-emitting material, a fluorescent light-emitting material or phosphorescence different from the fluorescent light-emitting material or phosphorescent light-emitting material contained in the light-emitting layer is used. A light emitting material can be used.
Details of these fluorescent materials and phosphorescent materials are described in, for example, paragraph numbers [0100] to [0164] of JP-A-2008-270736 and paragraph numbers [0088] to [0090] of JP-A-2007-266458. The matters described in these publications can be applied to the present invention.

Examples of phosphorescent light-emitting materials that can be used in the present invention include US Pat. / 19373A2, JP-A No. 2001-247859, JP-A No. 2002-302671, JP-A No. 2002-117978, JP-A No. 2003-133074, JP-A No. 2002-1235076, JP-A No. 2003-123684, JP-A No. 2002-170684, EP No. 121157, JP-A No. 2002 -226495, JP 2002-234894, JP 2001-247859, JP 2001-298470, JP 2002-17367 , JP-A-2002-203678, JP-A-2002-203679, JP-A-2004-357799, JP-A-2006-256999, JP-A-2007-19462, JP-A-2007-84635, JP-A-2007-96259, etc. Examples of such a light emitting material include Ir complex, Pt complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu complex, Tb complex, Gd. Examples include phosphorescent metal complex compounds such as complexes, Dy complexes, and Ce complexes. Particularly preferred is an Ir complex, a Pt complex, or a Re complex, among which an Ir complex or a Pt complex containing at least one coordination mode of a metal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond, and a metal-sulfur bond. Or Re complexes are preferred. Furthermore, from the viewpoints of luminous efficiency, driving durability, chromaticity and the like, an Ir complex and a Pt complex are particularly preferable, and an Ir complex is most preferable.
These phosphorescent metal complex compounds are preferably contained in the light emitting layer together with the compound represented by the general formula (1) or (2).

As the phosphorescent material contained in the light emitting layer in the present invention, an iridium complex represented by the following general formula (E-1) or a platinum complex represented by the following general formula (C-1) is used. It is preferable.

The general formula (E-1) will be described.

In general formula (E-1), Z ¹ and Z ² each independently represent a carbon atom or a nitrogen atom.
A ₁ represents an atomic group that forms a 5- or 6-membered heterocycle with Z ¹ and a nitrogen atom.
B ₁ represents an atomic group that forms a 5- or 6-membered ring with Z ² and a carbon atom.
(XY) represents a monoanionic bidentate ligand.
n _E1 represents an integer of 1 to 3.

n _E1 represents an integer of 1 to 3, preferably 2 or 3.
Z ¹ and Z ² each independently represent a carbon atom or a nitrogen atom. Z ¹ and Z ² are preferably carbon atoms.

A ₁ represents an atomic group that forms a 5- or 6-membered heterocycle with Z ¹ and a nitrogen atom. The 5- or 6-membered heterocycle containing A ₁ , Z ¹ and a nitrogen atom includes a pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadiazole Ring, thiadiazole ring and the like.
From the viewpoint of the stability of the complex, emission wavelength control, and emission quantum yield, the 5- or 6-membered heterocycle formed by A ₁ , Z ¹ and a nitrogen atom is preferably a pyridine ring, a pyrazine ring, an imidazole ring, or a pyrazole. A ring, more preferably a pyridine ring, an imidazole ring and a pyrazine ring, still more preferably a pyridine ring and an imidazole ring, and most preferably a pyridine ring.

The 5- or 6-membered heterocycle formed by the A ₁ , Z ¹ and the nitrogen atom may have a substituent, and as the substituent on the carbon atom, the substituent group A is on the nitrogen atom. The substituent group B can be applied as the substituent. Preferred substituents on carbon are alkyl groups, perfluoroalkyl groups, aryl groups, aromatic heterocyclic groups, dialkylamino groups, diarylamino groups, alkoxy groups, cyano groups, and fluorine atoms.

The substituent is appropriately selected for controlling the emission wavelength and potential, but in the case of shortening the wavelength, an electron donating group, a fluorine atom, and an aromatic ring group are preferable. For example, an alkyl group, a dialkylamino group, an alkoxy group, A fluorine atom, an aryl group, an aromatic heterocyclic group and the like are selected. In the case of increasing the wavelength, an electron withdrawing group is preferable, and for example, a cyano group, a perfluoroalkyl group, or the like is selected.

The substituent on nitrogen is preferably an alkyl group, an aryl group, or an aromatic heterocyclic group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex.
The substituents may be linked to form a condensed ring, and the formed ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazole. Ring, thiophene ring, furan ring and the like. These formed rings may have a substituent, and examples of the substituent include the substituent on the carbon atom and the substituent on the nitrogen atom.

B ₁ represents a 5- or 6-membered ring containing Z ² and a carbon atom. Examples of the 5- or 6-membered ring formed by B ₁ , Z ² and a carbon atom include a benzene ring, 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, Examples include a triazole ring, an oxadiazole ring, a thiadiazole ring, a thiophene ring, and a furan ring.
From the viewpoint of the stability of the complex, emission wavelength control and emission quantum yield, the benzene ring, pyridine ring, pyrazine ring, imidazole ring, pyrazole is preferable as the 5- or 6-membered ring formed by B ₁ , Z ² and carbon atom. A ring and a thiophene ring, more preferably a benzene ring, a pyridine ring and a pyrazole ring, and still more preferably a benzene ring and a pyridine ring.

The 5- or 6-membered ring formed of B ₁ , Z ² and a carbon atom may have a substituent, and the substituent group A is a substituent on a nitrogen atom as the substituent on the carbon atom. As the above, the substituent group B can be applied. Preferred substituents on carbon are alkyl groups, perfluoroalkyl groups, aryl groups, aromatic heterocyclic groups, dialkylamino groups, diarylamino groups, alkoxy groups, cyano groups, and fluorine atoms.

The substituent is appropriately selected for controlling the emission wavelength and potential, but in the case of increasing the wavelength, an electron donating group and an aromatic ring group are preferable, for example, an alkyl group, a dialkylamino group, an alkoxy group, an aryl group, An aromatic heterocyclic group or the like is selected. In order to shorten the wavelength, an electron withdrawing group is preferable, and for example, a fluorine atom, a cyano group, a perfluoroalkyl group, and the like are selected.

The substituent on nitrogen is preferably an alkyl group, an aryl group, or an aromatic heterocyclic group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex. The substituents may be linked to form a condensed ring, and the formed ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazole. Ring, thiophene ring, furan ring and the like. These formed rings may have a substituent, and examples of the substituent include the substituent on the carbon atom and the substituent on the nitrogen atom.
In addition, a 5- or 6-membered heterocyclic substituent formed by A ₁ , Z ¹ and a nitrogen atom and a 5- or 6-membered substituent formed by B ₁ , Z ² and a carbon atom are linked. Then, the same condensed ring as described above may be formed.

Examples of the ligand represented by (XY) include various known ligands used in conventionally known metal complexes. For example, “Photochemistry and Photophysics of Coordination Compounds” Springer-Verlag H. Published by Yersin in 1987, “Organometallic Chemistry-Fundamentals and Applications-” The ligands described in Akio Yamamoto's book published by Akio Yamamoto in 1982, etc. (for example, halogen ligands (preferably chlorine ligands), Nitrogen heteroaryl ligands (for example, bipyridyl, phenanthroline, etc.), diketone ligands (for example, acetylacetone, etc.) can be mentioned.
The ligands represented by (XY) are preferably the following general formulas (l-1) to (1-14), but the present invention is not limited to these.

* Represents the coordination position to iridium in the general formula (E-1). Rx, Ry and Rz each independently represents a hydrogen atom or a substituent.

When Rx, Ry, and Rz represent a substituent, examples of the substituent include a substituent selected from the substituent group A. Preferably, Rx and Rz are each independently an alkyl group, a perfluoroalkyl group, a fluorine atom or an aryl group, more preferably an alkyl group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, A fluorine atom and an optionally substituted phenyl group are most preferred, and a methyl group, an ethyl group, a trifluoromethyl group, a fluorine atom and a phenyl group are most preferred. Ry is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, a fluorine atom or an aryl group, more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an optionally substituted phenyl group. And most preferably a hydrogen atom or a methyl group. Since these ligands are considered not to be sites where electrons are transported in the device or where electrons are concentrated by excitation, Rx, Ry, and Rz may be any chemically stable substituent, and the effects of the present invention can be achieved. Also has no effect. Since complex synthesis is easy, (I-1), (I-4) and (I-5) are preferred, and (I-1) is most preferred. Complexes having these ligands can be synthesized in the same manner as in known synthesis examples by using corresponding ligand precursors. For example, in the same manner as described in International Publication No. 2009-073245, page 46, it can be synthesized by the following method using commercially available difluoroacetylacetone.
The ligand represented by (XY) is preferably a diketone or a picolinic acid derivative, and is acetylacetonate (acac) shown below from the viewpoint of obtaining stability of the complex and high luminous efficiency. Most preferred.

* Represents the coordination position to iridium.

A preferred embodiment of the Ir complex represented by the general formula (E-1) is an Ir complex represented by the general formula (E-2).

In general formula (E-2), A ^E1 to A ^E8 each independently represent a nitrogen atom or C—R ^E.
R ^E represents a hydrogen atom or a substituent.
(XY) represents a monoanionic bidentate ligand.
n _E2 represents an integer of 1 to 3.

A ^E1 to A ^E8 each independently represents a nitrogen atom or C—R ^E. R ^E represents a hydrogen atom or a substituent, and R ^E may be connected to each other to form a ring. Examples of the ring formed include the same ring as the condensed ring described in the general formula (E-1). Examples of the substituent represented by R ^E, we are the same as those mentioned above substituent group A.
Preferred as A ^E1 ~ ^{A E4} is ^{C-R ^E,} if A E1 ^{~ A E4} is ^{C-R ^E,} preferably a hydrogen atom ^{R E} of ^{A E3,} alkyl group, aryl group, amino group, An alkoxy group, an aryloxy group, a fluorine atom, or a cyano group, more preferably a hydrogen atom, an alkyl group, an amino group, an alkoxy group, an aryloxy group, or a fluorine atom, and particularly preferably a hydrogen atom or a fluorine atom. And R ^E of A ^E1 , A ^E2 and A ^E4 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 alkyl group, an amino group, an alkoxy group, an aryloxy group, or a fluorine atom, particularly preferably a hydrogen atom.

A ^E5 to A ^E8 are preferably C—R ^E , and when A ^E5 to A ^E8 are C—R ^E , R ^E is preferably a hydrogen atom, alkyl group, perfluoroalkyl group, aryl group, aromatic A heterocyclic group, a dialkylamino group, a diarylamino group, an alkyloxy group, a cyano group, or a fluorine atom, more preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, a dialkylamino group, a cyano group, Or a fluorine atom, and more preferably a hydrogen atom, an alkyl group, a trifluoromethyl group, or a fluorine atom. If possible, the substituents may be linked to form a condensed ring structure. When the emission wavelength is shifted to the short wavelength side, A ^E6 is preferably a nitrogen atom.
(X-Y), and _{n E2} of the general formula in (E1) (X-Y) , and has the same meaning as _{n E1} preferable ranges are also the same.

A more preferred form of the compound represented by the general formula (E-2) is a compound represented by the following general formula (E-3).

In general formula (E-3), R ^T1 , R ^T2 , R ^T3 , R ^T4 , R ^T5 , R ^T6 and R ^T7 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, —CN, a perfluoroalkyl group, a trifluorovinyl group, —CO ₂ R, —C (O) R, —NR ₂ , —NO ₂ , —OR, a halogen atom, an aryl group or a heteroaryl group, and further a substituent Z may be included. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
A represents CR ′ or a nitrogen atom, and R ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, —CN, a perfluoroalkyl group, a trifluorovinyl group, —CO ₂ R, —C (O ) R, —NR ₂ , —NO ₂ , —OR, a halogen atom, an aryl group or a heteroaryl group, which may further have a substituent Z. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
R ^T1 to R ^T7 and R ′ 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 Z. Among these, a case where a ring is condensed with R ^T1 and R ^T7 , or R ^T5 and R ^T6 to form a benzene ring is preferable, and a case where a ring is condensed with R ^T5 and R ^T6 to form a benzene ring is particularly preferable.
The substituents Z are each independently a halogen atom, —R ″, —OR ″, —N (R ″) ₂ , —SR ″, —C (O) R ″, —C (O) OR ″, —C ( O) represents N (R ″) ₂ , —CN, —NO ₂ , —SO ₂ , —SOR ″, —SO ₂ R ″, or —SO ₃ R ″, and each R ″ independently represents a hydrogen atom, alkyl Represents a group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
(XY) represents a monoanionic bidentate ligand. n _E3 represents an integer of 1 to 3.

The alkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent Z. The alkyl group represented by R ^T1 to R ^T7 and R ′ 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, such as methyl Group, ethyl group, i-propyl group, cyclohexyl group, t-butyl group and the like.
The cycloalkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent Z. The cycloalkyl group represented by R ^T1 to R ^T7 and R ′ is preferably a cycloalkyl group having 4 to 7 ring members, more preferably a cycloalkyl group having 5 to 6 carbon atoms in total, A cyclopentyl group, a cyclohexyl group, etc. are mentioned.
The alkenyl group represented by R ^T1 to R ^T7 and R ′ preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. For example, vinyl, allyl, Examples include 1-propenyl, 1-isopropenyl, 1-butenyl, 2-butenyl, 3-pentenyl and the like.
The alkynyl group represented by R ^T1 to R ^T7 and R ′ preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. For example, ethynyl, propargyl , 1-propynyl, 3-pentynyl and the like.

Examples of the perfluoroalkyl group represented by R ^T1 to R ^T7 and R ′ include those in which all the hydrogen atoms of the aforementioned alkyl group are replaced with fluorine atoms.

The aryl group represented by R ^T1 to R ^T7 and R ′ is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, such as a phenyl group, a tolyl group, or a naphthyl group.

The heteroaryl group represented by R ^T1 to R ^T7 and R ′ is preferably a heteroaryl group having 5 to 8 carbon atoms, more preferably a 5- or 6-membered substituted or unsubstituted heteroaryl group. Groups such as pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, cinnolinyl, phthalazinyl, quinoxalinyl, pyrrolyl, indolyl, furyl, benzofuryl , Thienyl group, benzothienyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group, triazolyl group, oxazolyl group, benzoxazolyl group, thiazolyl group, benzothiazolyl group, isothiazolyl group, benzisothiazolyl group, thiadiazolyl group, isoxazolyl group , Lens benzisoxazolyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, an imidazolidinyl group, a thiazolinyl group, a sulfolanyl group, a carbazolyl group, a dibenzofuryl group, dibenzothienyl group, such as 7 pyrido-indolyl group. Preferred examples include pyridyl group, pyrimidinyl group, imidazolyl group, and thienyl group, and more preferred are pyridyl group and pyrimidinyl group.

R ^T1 to R ^T7 and R ′ are preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a perfluoroalkyl group, a dialkylamino group, a fluoro group, an aryl group or a heteroaryl group, more preferably A hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a fluoro group, and an aryl group are preferable, and a hydrogen atom, an alkyl group, and an aryl group are more preferable. As the substituent Z, an alkyl group, an alkoxy group, a fluoro group, a cyano group, and a dialkylamino group are preferable, and a hydrogen atom is more preferable.

Any two of R ^T1 to R ^T7 and R ′ 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 Z. The definition and preferred range of cycloalkyl, aryl, and heteroaryl formed are the same as the cycloalkyl group, aryl group, and heteroaryl group defined by R ^T1 to R ^T7 and R ′.
Further, it is particularly preferable that A represents CR ′, and among R ^T1 to R ^T7 and R ′, 0 to 2 are alkyl groups or phenyl groups, and the rest are all hydrogen atoms, and R ^T1 to R ^T7 , And R ′ are particularly preferably a case where 0 to 2 are alkyl groups and the rest are all hydrogen atoms.

n _E3 is preferably 2 or 3. The type of ligand in the complex is preferably composed of 1 to 2 types, more preferably 1 type. When introducing a reactive group into the complex molecule, it is also preferred that the ligand consists of two types from the viewpoint of ease of synthesis.
(XY) has the same meaning as (XY) in formula (E-1), and the preferred range is also the same.

One preferred form of the compound represented by the general formula (E-3) is a compound represented by the following general formula (E-4).

R ^T1 to R ^T4 , A, (XY) and n _E4 in the general formula (E-4) are R ^T1 to R ^T4 , A, (XY) and n _{E3 in the} general formula (E-3). The preferred range is also the same. R ₁ ′ to R ₅ ′ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, cyano group, perfluoroalkyl group, trifluorovinyl group, —CO ₂ R, —C (O) R , —NR ₂ , —NO ₂ , —OR, a halogen atom, an aryl group or a heteroaryl group, and optionally having a substituent Z. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
Any _{one of} R ₁ ′ to R ₅ ′ 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 Z.
Z is independently a halogen atom, —R ″, —OR ″, —N (R ″) ₂ , —SR ″, —C (O) R ″, —C (O) OR ″, —C (O) _{_{_{N (R ") 2, -CN}}} , -NO 2, -SO 2, -SOR", - SO 2 R ", or _-SO 3 R" represents, R "are each independently a hydrogen atom, an alkyl group, A perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group is represented.
Further, preferred ranges for R ₁ ′ to R ₅ ′ are the same as R ^T1 to R ^T7 and R ′ in formula (E-3). Particularly preferably, A represents CR ′, and 0 to 2 of R ^T1 to R ^T4 , R ′, and R ₁ ′ to R ₅ ′ are alkyl groups or phenyl groups, and the rest are all hydrogen atoms. , R ^T1 to R ^T4 , R ′, and R ₁ ′ to R ₅ ′ are more preferably a case where 0 to 2 are alkyl groups and the rest are all hydrogen atoms.

Another preferred embodiment of the compound represented by the general formula (E-3) is a compound represented by the following general formula (E-5).

R ^T2 to R ^T6 , A, (XY) and n _E5 in the general formula (E-5) are R ^T2 to R ^T6 , A, (XY) and n _{E3 in the} general formula (E-3). The preferred range is also the same. R ₆ ′ to R ₈ ′ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, cyano group, perfluoroalkyl group, trifluorovinyl group, —CO ₂ R, —C (O) R , —NR ₂ , —NO ₂ , —OR, a halogen atom, an aryl group or a heteroaryl group, and optionally having a substituent Z. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
R ^T5 , R ^T6 , R ₆ ′ to R ₈ ′ may be combined with each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or It is a heteroaryl, and the condensed 4- to 7-membered ring may further have a substituent Z.
Z is independently a halogen atom, —R ″, —OR ″, —N (R ″) ₂ , —SR ″, —C (O) R ″, —C (O) OR ″, —C (O) _{_{_{N (R ") 2, -CN}}} , -NO 2, -SO 2, -SOR", - SO 2 R ", or _-SO 3 R" represents, R "are each independently a hydrogen atom, an alkyl group, A perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group is represented.
In addition, preferred ranges for R ₆ ′ to R ₈ ′ are the same as R ^T1 to R ^T7 and R ′ in formula (E-3). Particularly preferably, A represents CR ′, and among R ^T2 to R ^T6 , R ′, and R ₆ ′ to R ₈ ′, 0 to 2 are alkyl groups or phenyl groups, and the rest are all hydrogen atoms. , R ^T2 to R ^T6 , R ′, and R ₆ ′ to R ₈ ′ are more preferably a case where 0 to 2 are alkyl groups and the rest are all hydrogen atoms.

When the phosphorescent material represented by the general formula (E-4) or (E-5) is used, the compound represented by the general formula (1) is preferably contained in the light emitting layer or the electron transporting layer.

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

In general formula (E-6), R _1a to R _1k each independently represent a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, cyano group, perfluoroalkyl group, trifluorovinyl group, —CO ₂ R, —C (O) R, —NR ₂ , —NO ₂ , —OR, a halogen atom, an aryl group, or a heteroaryl group, which may further have a substituent Z. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
Any two of R _1a to R _1k 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 7-membered ring may further have a substituent Z.
Z is independently a halogen atom, —R ″, —OR ″, —N (R ″) ₂ , —SR ″, —C (O) R ″, —C (O) OR ″, —C (O) _{_{_{N (R ") 2, -CN}}} , -NO 2, -SO 2, -SOR", - SO 2 R ", or _-SO 3 R" represents, R "are each independently a hydrogen atom, an alkyl group, A perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group is represented.
(XY) represents a monoanionic bidentate ligand.
n _E6 represents an integer of 1 to 3.

In the general formula (E-6), preferred ranges of R _1a to R _1k are the same as those in R ^T1 to R ^T7 and R ′ in the general formula (E-3). Further, it is particularly preferred that 0 to 2 of R _1a to R _1k are alkyl groups or phenyl groups and the rest are all hydrogen atoms, and 0 to 2 of R _1a to R _1k are alkyl groups and the rest are all hydrogen atoms. More preferably, it is an atom.
The case where R _1j and R _1k are linked to form a single bond is particularly preferable.
The preferred range of (XY) and n _E6 is the same as (XY) and n _E3 in general formula (E-3).

A more preferable form of the compound represented by the general formula (E-6) is a case represented by the following general formula (E-7).

In general formula (E-7), R _1a to R _1i are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, cyano group, perfluoroalkyl group, trifluorovinyl group, —CO ₂ R, —C (O) R, —NR ₂ , —NO ₂ , —OR, a halogen atom, an aryl group, or a heteroaryl group, which may further have a substituent Z. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
Any one of R _1a to R _1i may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is a cycloalkyl group, an aryl group, or a heteroaryl group; The condensed 4- to 7-membered ring may further have a substituent Z.
Z is independently a halogen atom, —R ″, —OR ″, —N (R ″) ₂ , —SR ″, —C (O) R ″, —C (O) OR ″, —C (O) _{_{_{N (R ") 2, -CN}}} , -NO 2, -SO 2, -SOR", - SO 2 R ", or _-SO 3 R" represents, R "are each independently a hydrogen atom, an alkyl group, A perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group is represented.
(XY) represents a monoanionic bidentate ligand.
n _E7 represents an integer of 1 to 3.

In the formula _(E-7), definition and preferable ranges of R 1a _{~ R 1i} are the same as _R 1a _{~ R 1i} in the formula (E-6). Further, it is particularly preferable that 0 to 2 of R _1a to R _1i are alkyl groups or aryl groups and the rest are all hydrogen atoms. The definitions and preferred ranges of (XY) and n _E7 are the same as (XY) and n _E3 in general formula (E-3).

When the phosphorescent material represented by the general formula (E-6) or (E-7) is used, the compound represented by the general formula (1) is preferably contained in the light emitting layer or the electron transport layer.

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

The compounds exemplified as the compound represented by the general formula (E-1) can be synthesized by the method described in JP2009-99783A, various methods described in US Pat. No. 7,279,232 and the like. After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.

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

The compound represented by the general formula (E-1) in the light emitting layer is generally contained in the light emitting layer in an amount of 0.1% by mass to 50% by mass with respect to the total mass of the compound forming the light emitting layer. From the viewpoint of durability and external quantum efficiency, the content is preferably 1% by mass to 50% by mass, and more preferably 2% by mass to 40% by mass.

The platinum complex that can be used as the phosphorescent material is preferably a platinum complex represented by the following general formula (C-1).

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

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

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

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

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

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

The general formula (C-2) will be described. L ²¹ has the same meaning as L ^{1 in} formula (C-1), and the preferred range is also the same.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

The general formula (C-6) will be described. L ⁶¹ has the same meaning as L ^{1 in} formula (C-1), and the preferred range is also the same.

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

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

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

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

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

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

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

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

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

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

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

The light emitting layer in the element of the present invention may be composed of only a light emitting material, or may be a mixed layer of a host material and a light emitting material. There may be one kind of luminescent material, or two or more kinds. The host material is preferably a charge transport material. The host material may be one type or two or more types, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed. Furthermore, the light emitting layer may contain a material that does not have charge transporting properties and does not emit light.
Further, the light emitting layer may be a single layer or a multilayer of two or more layers, and each layer may contain the same light emitting material or host material, or each layer may contain a different material. When there are a plurality of light emitting layers, each of the light emitting layers may emit light with different emission colors.

(Host material)
The host material is a compound mainly responsible for charge injection and transport in the light emitting layer, and itself is a compound that does not substantially emit light. Here, “substantially does not emit light” means that the amount of light emitted from the compound that does not substantially emit light is preferably 5% or less, more preferably 3% or less of the total amount of light emitted from the entire device. Preferably it says 1% or less.
As the host material, a compound represented by the general formula (1) or (2) can be used.

Examples of other host materials that can be used in the present invention include the following compounds.
Pyrrole, indole, carbazole, azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole, imidazole, furan, benzofuran, dibenzofuran, thiophene, benzothiophene, dibenzothiophene, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, aryl Amine, amino-substituted chalcone, styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatic tertiary amine compound, styrylamine compound, porphyrin compound, polysilane compound, poly (N-vinylcarbazole), aniline copolymer , Conductive polymer oligomer such as thiophene oligomer, polythiophene, organosilane, carbon film, pyridine, pyrimidine, triazine, Midazole, pyrazole, triazole, oxazole, oxadiazol, fluorenone, anthraquinodimethane, anthrone, diphenylquinone, thiopyran dioxide, carbodiimide, fluorenylidenemethane, distyrylpyrazine, fluorine-substituted aromatic compound, Various metal complexes typified by metal complexes of heterocyclic tetracarboxylic anhydrides such as naphthalene and perylene, metal complexes of phthalocyanine and 8-quinolinol derivatives, metal phthalocyanine, benzoxazole and benzothiazole And derivatives thereof (which may have a substituent or a condensed ring).

In the present invention, the host material that can be used in combination may be a hole transporting host material or an electron transporting host material.
In the present invention, the light emitting layer preferably contains a host material. The host material is preferably a compound represented by the general formula (1) or (2), or a compound represented by the following general formula (4-1) or (4-2).
In the present invention, when the compound represented by the general formula (1) or (2) is contained in the organic layer (preferably the electron transport layer) between the light emitting layer and the cathode, the light emitting layer has the general formula (4-1). Or at least one of the compounds represented by (4-2).

In the present invention, when the compound represented by the general formula (4-1) or (4-2) is contained in the light emitting layer, the compound represented by the general formula (4-1) or (4-2) is The light emitting layer preferably contains 30 to 100% by mass, more preferably 40 to 100% by mass, and particularly preferably 50 to 100% by mass. In addition, when the compound represented by the general formula (4-1) or (4-2) is used in a plurality of organic layers, it is preferable that each layer contains the above-mentioned range.

The compound represented by the general formula (4-1) or (4-2) may contain only one kind in any organic layer, and a plurality of general formulas (4-1) or (4) The compound represented by -2) may be contained in combination at any ratio.

(In the general formulas (4-1) and (4-2), d and e each represent an integer of 0 to 3, at least one of which is 1 or more, f represents an integer of 1 to 4. R ′ ₈ is Each independently represents a substituent, and when d, e and f are 2 or more, R ′ ₈ may be different or the same, and at least one of R ′ ₈ is represented by the following general formula (5). Represents a carbazole group.)

(In general formula (5), R ′ ₉ each independently represents a substituent. G represents an integer of 0 to 8.)

R ′ ₈ independently represents a substituent, specifically, a halogen atom, an alkoxy group, a cyano group, a nitro group, an alkyl group, an aryl group, a heterocyclic group, or a substituent represented by the general formula (5) It is. When R ′ ₈ does not represent the general formula (5), it is preferably an alkyl group having 10 or less carbon atoms, a substituted or unsubstituted aryl group having 10 or less carbon atoms, and more preferably an alkyl group having 6 or less carbon atoms. It is.

R ′ ₉ each independently represents a substituent, specifically a halogen atom, an alkoxy group, a cyano group, a nitro group, an alkyl group, an aryl group, or a heterocyclic group, preferably an alkyl group having 10 or less carbon atoms, A substituted or unsubstituted aryl group having 10 or less carbon atoms, more preferably an alkyl group having 6 or less carbon atoms.
g represents an integer of 0 to 8 and is preferably 0 to 4 from the viewpoint of not shielding too much the carbazole skeleton responsible for charge transport. From the viewpoint of ease of synthesis, when carbazole has a substituent, those having a substituent so as to be symmetric with respect to the nitrogen atom are preferable.

In general formula (4-1), the sum of d and e is preferably 2 or more from the viewpoint of maintaining the charge transport ability. Further, R ′ ₈ is preferably substituted with meta for the other benzene ring. The reason for this is that in ortho substitution, the steric hindrance between adjacent substituents is large, so that the bond is easily cleaved, and the durability is lowered. In addition, in para substitution, the molecular shape approaches a rigid rod shape and is easily crystallized, so that element degradation is likely to occur under high temperature conditions. Specifically, a compound represented by the following structure is preferable. R of structure shown below _'9 and g, R in the formula (5)' is synonymous with ₉ and g.

In the general formula (4-2), f is preferably 2 or more from the viewpoint of maintaining the charge transport ability. When f is 2 or 3, it is preferable that R ′ ₈ is substituted with meta from the same viewpoint. Specifically, a compound represented by the following structure is preferable. R in the structure shown below _'9 and g, R in the formula (5)' is synonymous with ₉ and g.

When the general formulas (4-1) and (4-2) have a hydrogen atom, an isotope of hydrogen (such as a deuterium atom) is also included. In this case, all hydrogen atoms in the compound may be replaced with hydrogen isotopes, or a mixture in which a part is a compound containing hydrogen isotopes may be used. Preferably, R ′ ₉ in the general formula (5) is substituted with deuterium, and the following structures are particularly preferable.

In addition, the atoms constituting the substituents also include their isotopes.

The compounds represented by the general formulas (4-1) and (4-2) can be synthesized by combining various known synthesis methods. Most commonly, carbazole compounds are synthesized by dehydroaromatization after the Athercorp rearrangement reaction of a condensate of an aryl hydrazine and a cyclohexane derivative (LF Tieze, by Th. Eicher, translated by Takano, Ogasawara, Precision organic synthesis, page 339 (published by Nankodo). Regarding the coupling reaction of the obtained carbazole compound and halogenated aryl compound using a palladium catalyst, Tetrahedron Letters 39: 617 (1998), 39: 2367 (1998) and 40: 6393 (1999) and the like. The reaction temperature and reaction time are not particularly limited, and the conditions described in the above literature can be applied. Some compounds such as mCP that are commercially available can be suitably used.

In the present invention, the compounds represented by the general formulas (4-1) and (4-2) preferably form a thin layer by a vacuum deposition process, but a wet process such as solution coating is also preferably used. I can do it. The molecular weight of the compound is preferably 2000 or less, more preferably 1200 or less, and particularly preferably 800 or less from the viewpoints of deposition suitability and solubility. Also, 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. Particularly preferred.

The general formulas (4-1) and (4-2) are preferably the following structures or compounds in which one or more hydrogen atoms are substituted with deuterium atoms. R in the structure shown below _'8, the formula (4-1) and (4-2) R' in the same meaning as _8, R _'9 is R in the formula (5)' and ₉ It is synonymous.

Specific examples of the compounds represented by the general formulas (4-1) and (4-2) in the present invention are illustrated below, but the present invention is not limited to these.

In the light emitting layer, the triplet lowest excitation energy (T ₁ energy) of the host material is preferably higher than the T ₁ energy of the phosphorescent light emitting material in terms of color purity, light emission efficiency, and driving durability. It is preferable _{T 1} is greater 0.1eV higher than the _{T 1} of the phosphorescent material of the host material, more preferably at least 0.2eV higher, and further preferably more than 0.3eV large.
T ₁ of the host material is a large T ₁ is obtained from the phosphorescent material to the host material for thereby quench T ₁ is less than the light emission of the phosphorescent material. Even if the T _{1 of} the host material is larger than the phosphorescent light emitting material, if the difference in T ₁ between the two is small, the reverse energy transfer from the phosphorescent light emitting material to the host material occurs in part, resulting in a decrease in efficiency and durability. Cause. Therefore, there is a demand for a host material having a sufficiently large T ₁ and high chemical stability and carrier injection / transport properties.

Further, the content of the host compound in the present invention is not particularly limited, but from the viewpoint of light emission efficiency and driving voltage, it is 15% by mass to 95% by mass with respect to the total compound mass forming the light emitting layer. Preferably there is. When the light emitting layer contains a plurality of types of host compounds including the compound represented by the general formula (1) or (2), the compound represented by the general formula (1) or (2) is 50 mass in the total host compounds. % Or more and 99% by mass or less is preferable.

[Compound represented by formula (M-1)]
In the organic electroluminescent element of the present invention, the pair of electrodes preferably includes an anode, and preferably includes at least one organic layer between the light emitting layer and the anode, and the organic layer includes at least one general formula shown below. The compound represented by (M-1) is preferably contained.

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

In General Formula (M-1), Ar ₁ and Ar ₂ are each independently one or more selected from alkyl, aryl, heteroaryl, arylamino, alkylamino, morpholino, thiomorpholino, N, O, and S It represents a 5- or 6-membered heterocycloalkyl or cycloalkyl containing a hetero atom, and may further have a substituent Z. Ar ₁ and Ar ₂ may be bonded to each other by a single bond, alkylene, or alkenylene (with or without a condensed ring) to form a condensed 5- to 9-membered ring.
Ar ₃ represents alkyl, aryl, heteroaryl, or arylamino, and may further have a substituent Z.
Z is independently a halogen atom, —R ″, —OR ″, —N (R ″) ₂ , —SR ″, —C (O) R ″, —C (O) OR ″, —C (O) _{_{_{N (R ") 2, -CN}}} , -NO 2, -SO 2, -SOR", - SO 2 R ", or _-SO 3 R" represents, R "are each independently a hydrogen atom, an alkyl group, A perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group is represented.
p is an integer of 1 to 4, and when p is 2 or more, Ar ₁ and Ar ₂ may be the same or different.

Another preferred embodiment of the compound represented by the general formula (M-1) is a case represented by the following general formula (M-2).

In general formula (M-2), R ^M1 represents an alkyl group, an aryl group, or a heteroaryl group.
R ^M2 to R ^M23 each independently represent a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, an amino group, a silyl group, a cyano group, a nitro group, or a fluorine atom.

In general formula (M-2), R ^M1 represents an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). Which may have the aforementioned substituent Z. R ^M1 is preferably an aryl group or a heteroaryl group, and more preferably an aryl group. Preferred substituents when the aryl group of R ^M1 has a substituent include an alkyl group, a halogen atom, a cyano group, an aryl group, and an alkoxy group, and an alkyl group, a halogen atom, a cyano group, and an aryl group are more preferable. An alkyl group, a cyano group, or an aryl group is more preferable. The aryl group of R ^M1 is preferably a phenyl group that may have a substituent Z, and more preferably a phenyl group that may have an alkyl group or a cyano group.

R ^M2 to R ^M23 are each independently a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), a heteroaryl group (preferably having 4 to 12 carbon atoms), Alkoxy group (preferably having 1 to 8 carbon atoms), aryloxy group (preferably having 6 to 30 carbon atoms), amino group (preferably having 0 to 24 carbon atoms), silyl group (preferably having 0 to 18 carbon atoms), cyano Represents a group, a nitro group, or a fluorine atom, and these may have the aforementioned substituent Z.

R ^M2 , R ^M7 , R ^M8 , R ^M15 , R ^M16 and R ^M23 are preferably a hydrogen atom or an alkyl group or an aryl group which may have a substituent Z, more preferably a hydrogen atom. .
R ^M4 , R ^M5 , R ^M11 , R ^M12 , R ^M19, and R ^M20 are preferably a hydrogen atom, an alkyl or aryl group optionally having substituent Z, or a fluorine atom, more preferably a hydrogen atom. Is an atom.
R ^M3 , R ^M6 , R ^M9 , R ^M14 , R ^M17 and R ^M22 are preferably a hydrogen atom, an alkyl or aryl group optionally having substituent Z, a fluorine atom, or a cyano group, and more A hydrogen atom or an alkyl group which may have a substituent Z is preferable, and a hydrogen atom is more preferable.
R ^M10 , R ^M13 , R ^M18 and R ^M21 are preferably a hydrogen atom, an alkyl group optionally having a substituent Z, an aryl group, a heteroaryl group or an amino group, a nitro group, a fluorine atom, or a cyano group More preferably a hydrogen atom, an alkyl or aryl group optionally having a substituent Z, a nitro group, a fluorine atom, or a cyano group, still more preferably a hydrogen atom or a substituent Z. It is an alkyl group that may be present. When the alkyl group has a substituent, the substituent is preferably a fluorine atom, and the alkyl group which may have the substituent Z preferably has 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms. is there.

Another preferred embodiment of the compound represented by the general formula (M-1) is a case represented by the following general formula (M-3).

In the general formula (M-3), R ^S1 to R ^S5 are each independently an alkyl group, cycloalkyl group, alkenyl group, alkynyl group, —CN, perfluoroalkyl group, trifluorovinyl group, —CO ₂ R, —C (O) represents R, —NR ₂ , —NO ₂ , —OR, a halogen atom, an aryl group or a heteroaryl group, and may further have a substituent Z. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group. When a plurality of R ^S1 to R ^S5 are present, they may be bonded to each other to form a ring, and may further have a substituent Z.
a represents an integer of 0 to 4, and when a plurality of R ^S1 are present, they may be the same or different and may be bonded to each other to form a ring. b to e each independently represent an integer of 0 to 5, and when there are a plurality of R ^S2 to R ^S5 , they may be the same or different, and any two may combine to form a ring. Good.
q is an integer of 1 to 5, and when q is 2 or more, a plurality of R ^S1 may be the same or different, and may be bonded to each other to form a ring.

The alkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent Z. The alkyl group represented by R ^S1 to R ^S5 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, such as a methyl group or an ethyl group. , I-propyl group, cyclohexyl group, t-butyl group and the like.
The cycloalkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent Z. The cycloalkyl group represented by R ^S1 to R ^S5 is preferably a cycloalkyl group having 4 to 7 ring members, more preferably a cycloalkyl group having 5 to 6 carbon atoms in total, such as a cyclopentyl group and cyclohexyl group. Groups and the like.
The alkenyl group represented by R ^S1 to R ^S5 preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. For example, vinyl, allyl, 1-propenyl, Examples include 1-isopropenyl, 1-butenyl, 2-butenyl, 3-pentenyl and the like.
The alkynyl group represented by R ^S1 to R ^S5 preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. For example, ethynyl, propargyl, 1-propynyl , 3-pentynyl and the like.

^Examples of the perfluoroalkyl group represented by R ^S1 to R ^S5 include those in which all hydrogen atoms of the aforementioned alkyl group are replaced with fluorine atoms.

The aryl group represented by R ^S1 to R ^S5 is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, such as a phenyl group, a tolyl group, a biphenyl group, and a terphenyl group.

The heteroaryl group represented by R ^S1 to R ^S5 is preferably a heteroaryl group having 5 to 8 carbon atoms, more preferably a 5- or 6-membered substituted or unsubstituted heteroaryl group, For example, pyridyl group, pyrazinyl group, pyridazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, cinnolinyl group, phthalazinyl group, quinoxalinyl group, pyrrolyl group, indolyl group, furyl group, benzofuryl group, thienyl group, Benzothienyl, pyrazolyl, imidazolyl, benzimidazolyl, triazolyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, isothiazolyl, benzisothiazolyl, thiadiazolyl, isoxazolyl, benziso Kisazoriru group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, an imidazolidinyl group, a thiazolinyl group, a sulfolanyl group, a carbazolyl group, a dibenzofuryl group, dibenzothienyl group, a pyrido-indolyl group. Preferred examples include pyridyl group, pyrimidinyl group, imidazolyl group, and thienyl group, and more preferred are pyridyl group and pyrimidinyl group.

R ^S1 to R ^S5 are preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a perfluoroalkyl group, a dialkylamino group, a fluoro group, an aryl group, or a heteroaryl group, more preferably a hydrogen atom or an alkyl group. Group, cyano group, trifluoromethyl group, fluoro group and aryl group, more preferably a hydrogen atom, an alkyl group and an aryl group. As the substituent Z, an alkyl group, an alkoxy group, a fluoro group, a cyano group, and a dialkylamino group are preferable, and a hydrogen atom and an alkyl group are more preferable.

Any one of R ^S1 to R ^S5 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 7-membered ring may further have a substituent Z. The definition and preferred range of cycloalkyl, aryl, and heteroaryl formed are the same as the cycloalkyl group, aryl group, and heteroaryl group defined by R ^S1 to R ^S5 .

When the compound represented by the general formula (M-1) is used in the hole transport layer, the compound represented by the general formula (M-1) is preferably contained in an amount of 50 to 100% by mass, The content is preferably 100% by mass, and particularly preferably 95 to 100% by mass.
In addition, when the compound represented by the general formula (M-1) is used in a plurality of organic layers, it is preferable that each layer contains the above-mentioned range.

The compound represented by the general formula (M-1) may contain only one kind in any organic layer, and the compound represented by the plurality of general formulas (M-1) You may contain in combination.

The thickness of the hole transport layer containing the compound represented by the general formula (M-1) is preferably 1 nm to 500 nm, more preferably 3 nm to 200 nm, and more preferably 5 nm to 100 nm. Further preferred. The hole transport layer is preferably provided in contact with the light emitting layer.
The hole transport layer may have a single layer structure composed of one or more of the materials described above, or a multilayer structure composed of a plurality of layers having the same composition or different compositions.

The lowest excited triplet (T ₁ ) energy in the film state of the compound represented by the general formula (M-1) is preferably 2.52 eV (58 kcal / mol) or more and 3.47 eV (80 kcal / mol) or less. It is more preferably 2.60 eV (60 kcal / mol) or more and 3.25 eV (75 kcal / mol) or less, and further preferably 2.69 eV (62 kcal / mol) or more and 3.04 eV (70 kcal / mol) or less.

The hydrogen atom constituting the general formula (M-1) includes hydrogen isotopes (such as deuterium atoms). In this case, all hydrogen atoms in the compound may be replaced with hydrogen isotopes, or a mixture in which a part is a compound containing hydrogen isotopes may be used.

The compound represented by the general formula (M-1) can be synthesized by combining various known synthesis methods. Most commonly, carbazole compounds are synthesized by dehydroaromatization after the Athercorp rearrangement reaction of a condensate of an aryl hydrazine and a cyclohexane derivative (LF Tieze, by Th. Eicher, translated by Takano, Ogasawara, Precision organic synthesis, page 339 (published by Nankodo). Regarding the coupling reaction of the obtained carbazole compound and halogenated aryl compound using a palladium catalyst, Tetrahedron Letters 39: 617 (1998), 39: 2367 (1998) and 40: 6393 (1999) and the like. The reaction temperature and reaction time are not particularly limited, and the conditions described in the above literature can be applied.

The compound represented by the general formula (M-1) of the present invention is preferably formed into a thin layer by a vacuum deposition process, but a wet process such as solution coating can also be suitably used. The molecular weight of the compound is preferably 2000 or less, more preferably 1200 or less, and particularly preferably 800 or less from the viewpoints of deposition suitability and solubility. Also, 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. Particularly preferred. *

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

[Aromatic hydrocarbon compounds]
In the organic electroluminescent element of the present invention, the pair of electrodes preferably includes a cathode, and preferably includes at least one organic layer between the light emitting layer and the cathode, and the organic layer includes an aromatic hydrocarbon compound. It is preferable to do.
The aromatic hydrocarbon compound is more preferably contained in an organic layer adjacent to the light emitting layer between the light emitting layer and the cathode, but its use is not limited, and any of the organic layers may be further added. It may be contained. As the introduction layer of the aromatic hydrocarbon compound according to the present invention, any one or more of a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, and a charge block layer are used. It can contain.
The organic layer adjacent to the light emitting layer between the light emitting layer and the cathode and containing the aromatic hydrocarbon compound is preferably a charge blocking layer or an electron transporting layer, and more preferably an electron transporting layer.

The aromatic hydrocarbon compound preferably comprises only carbon atoms and hydrogen atoms from the viewpoint of ease of synthesis.
When the aromatic hydrocarbon compound is contained in a layer other than the light emitting layer, it is preferably contained in an amount of 70 to 100% by mass, more preferably 85 to 100% by mass. When the aromatic hydrocarbon compound is contained in the light emitting layer, it is preferably contained in an amount of 0.1 to 99% by weight, more preferably 1 to 95% by weight, based on the total weight of the light emitting layer. It is more preferable to include the mass%.
It is preferable to use a hydrocarbon compound having only a carbon atom and a hydrogen atom, a molecular weight in the range of 400 to 1200, and a condensed polycyclic skeleton having a total carbon number of 13 to 22. The condensed polycyclic skeleton having 13 to 22 carbon atoms is preferably any one of fluorene, anthracene, phenanthrene, tetracene, chrysene, pentacene, pyrene, perylene, and triphenylene. From the viewpoint of T ₁ , fluorene, triphenylene, phenanthrene. Is more preferable, and triphenylene is more preferable from the viewpoint of stability of the compound and charge injection / transport properties, and a compound represented by the general formula (Tp-1) is particularly preferable.

The hydrocarbon compound represented by the general formula (Tp-1) preferably has a molecular weight in the range of 400 to 1200, more preferably 400 to 1000, and still more preferably 400 to 800. If the molecular weight is 400 or more, a high-quality amorphous thin film can be formed, and if the molecular weight is 1200 or less, it is preferable in terms of solubility in a solvent, sublimation, and appropriate deposition.

The use of the hydrocarbon compound represented by the general formula (Tp-1) is not limited, and it may be further contained not only in the organic layer adjacent to the light emitting layer but also in any layer within the organic layer.

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

Examples of the alkyl group represented by R ¹² to R ²³ are substituted or unsubstituted, for example, methyl group, ethyl group, isopropyl group, n-butyl group, tert-butyl group, n-octyl group, n-decyl group, and an n-hexadecyl group, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, and the like, preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, and a cyclohexyl group, more preferably a methyl group, an ethyl group, or A tert-butyl group.

R ¹² to R ²³ are preferably an alkyl group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group (these are further an alkyl group, a phenyl group, a fluorenyl group). More preferably a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, which may be substituted with a group, a naphthyl group, or a triphenylenyl group.
A benzene ring that may be substituted with a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group (which may be further substituted with an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group); It is particularly preferred.

In the general formula (Tp-1), the total number of aryl rings is preferably 2 to 8, and preferably 3 to 5. By setting it as this range, a high-quality amorphous thin film can be formed, and solubility in a solvent, sublimation, and deposition suitability are improved.

R ¹² to R ²³ each independently preferably has a total carbon number of 20 to 50, more preferably a total carbon number of 20 to 36. By setting it as this range, a high-quality amorphous thin film can be formed, and solubility in a solvent, sublimation, and deposition suitability are improved.

In one embodiment of the present invention, the hydrocarbon compound represented by the general formula (Tp-1) is preferably a hydrocarbon compound represented by the following general formula (Tp-2).

(In the general formula (Tp-2), a plurality of Ar ¹ are the same, and a phenyl group, a fluorenyl group, a naphthyl group, which may be substituted with an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, Or represents a triphenylenyl group.)

An alkyl group and an alkyl group represented by Ar ¹ , a phenyl group, a fluorenyl group, a naphthyl group, or a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group that may be substituted with a triphenylenyl group include R ¹² to R ²³ . It is synonymous with what was mentioned, and a preferable thing is also the same.

In another embodiment of the present invention, the hydrocarbon compound represented by the general formula (Tp-1) is preferably a hydrocarbon compound represented by the following general formula (Tp-3).

(In General Formula (Tp-3), L represents an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a phenyl group, a fluorenyl group, a naphthyl group, a triphenylenyl group, which may be substituted with a triphenylenyl group, or a combination thereof. And n represents an integer of 1 to 6.)

The alkyl group, phenyl group, fluorenyl group, naphthyl group, or triphenylenyl group that forms the n-valent linking group represented by L has the same meaning as that described for R ¹² to R ²³ .
L is preferably an alkyl group or an n-valent linking group formed by combining a benzene ring, a fluorene ring, or a combination thereof, which may be substituted with a benzene ring.
Although the preferable specific example of L is given to the following, it is not limited to these. In the specific examples, it is bonded to the triphenylene ring by *.

N is preferably 1 to 5, and more preferably 1 to 4.

In another embodiment of the present invention, the hydrocarbon compound represented by the general formula (Tp-1) is preferably a hydrocarbon compound represented by the following general formula (Tp-4).

(In General Formula (Tp-4), Ar ² in the case where a plurality of Ar ² are present is the same, and Ar ² represents a group formed by substitution with an alkyl group, phenyl group, naphthyl group, or triphenylenyl group, or a combination thereof. , And q each independently represent 0 or 1, but p and q are not simultaneously 0. When p and q represent 0, Ar ² represents a hydrogen atom.)

Ar ² is preferably a group formed by combining an alkyl group having 1 to 4 carbon atoms, a phenyl group, a naphthyl group, or a triphenylenyl group, and more preferably a combination of a methyl group, a t-butyl group, a phenyl group, or a triphenylenyl group. It is a group consisting of
Ar ² is particularly preferably a benzene ring substituted with an alkyl group having 1 to 4 carbon atoms at the meta position, a phenyl group, a naphthyl group, a triphenylenyl group, or a combination thereof.

When the hydrocarbon compound according to the present invention is used as a host material of a light emitting layer of an organic electroluminescent device or a charge transport material of a layer adjacent to the light emitting layer, the energy gap in a thin film state than the light emitting material (the light emitting material is a phosphorescent light emitting material) In the case of ( ₂ ), when the lowest excited triplet (T ₁ ) energy in the thin film state is large, the emission is prevented from being quenched, which is advantageous for improving the efficiency. On the other hand, from the viewpoint of chemical stability of the compound, it is preferable that the energy gap and T ₁ energy are not too large. The T ₁ energy in the film state of the hydrocarbon compound represented by the general formula (Tp-1) is preferably 52 kcal / mol or more and 80 kcal / mol or less, and 55 kcal / mol or more and 68 kcal / mol or less. Is more preferable, and it is still more preferable that they are 58 kcal / mol or more and 63 kcal / mol or less. In particular, when a phosphorescent light emitting material is used as the light emitting material, the T ₁ energy is preferably in the above range.

The T ₁ energy can be obtained by a method similar to the method in the description of the general formula (1) described above.

The glass transition temperature (Tg) of the hydrocarbon compound according to the present invention is 80 ° C. or more and 400 ° C. or less from the viewpoint of stably operating the organic electroluminescence device against heat generated during high temperature driving or during device driving. Preferably, it is 100 degreeC or more and 400 degrees C or less, More preferably, it is 120 degreeC or more and 400 degrees C or less.

Hereinafter, specific examples of the hydrocarbon compound according to the present invention will be exemplified, but the present invention is not limited thereto.

The compounds exemplified as the hydrocarbon compounds according to the present invention include those described in International Publication No. 05/013388, International Publication No. 06/130598, International Publication No. 09/021107, US2009 / 0009065, International Publication No. 09 / It can be synthesized by the methods described in the 008311 pamphlet and the international publication 04/018587 pamphlet.
After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.

[Compound represented by formula (O-1)]
The light emitting device of the present invention preferably contains at least one organic layer between the light emitting layer and the cathode, and the organic layer contains at least one compound represented by the following general formula (O-1). This is preferable from the viewpoints of element efficiency and driving voltage. The general formula (O-1) will be described below.

(In the general formula ^{(O1), R O1} represents an alkyl group, an aryl group, or each independently ^.A O1 ^{~ A O4} representing the heteroaryl group, the ^{C-R A} or .R ^A representing the nitrogen atom Represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and a plurality of R ^A may be the same or different, and L ^O1 represents a divalent to hexavalent linking group comprising an aryl ring or a heteroaryl ring. N ^O1 represents an integer of 2 to 6.)

R ^O1 represents an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). It may have a substituent selected from group A. R ^O1 is preferably an aryl group or a heteroaryl group, more preferably an aryl group. As a preferable substituent when the aryl group of R ^O1 has a substituent, an alkyl group, an aryl group or a cyano group can be mentioned, an alkyl group or an aryl group is more preferable, and an aryl group is still more preferable. When the aryl group of R ^O1 has a plurality of substituents, the plurality of substituents may be bonded to each other to form a 5- or 6-membered ring. The aryl group of R ^O1 is preferably a phenyl group which may have a substituent selected from substituent group A, more preferably a phenyl group which may be substituted with an alkyl group or an aryl group, More preferred is an unsubstituted phenyl group or 2-phenylphenyl group.

A ^O1 to A ^O4 each independently represent C—R ^A or a nitrogen atom. Of A ^O1 to A ^O4 , 0 to 2 are preferably nitrogen atoms, and 0 or 1 is more preferably a nitrogen atom. Or all of ^A ^O1 ~ A ^O4 is ^{C-R A,} or ^{A O1} be a nitrogen ^atom, is preferably ^A O2 ^~ A ^O4 is ^{C-R ^A,} ^{A O1} be a nitrogen ^{atom, A O2} ~ More preferably, A ^O4 is C—R ^A , more preferably A ^O1 is a nitrogen atom, A ^O2 to A ^O4 are C—R ^A , and R ^A is all a hydrogen atom.

R ^A represents a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). It may have a substituent selected from the substituent group A. The plurality of ^RA may be the same or different. R ^A is preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.

L ^O1 represents a divalent to hexavalent linking group composed of an aryl ring (preferably having 6 to 30 carbon atoms) or a heteroaryl ring (preferably having 4 to 12 carbon atoms). L ^O1 is preferably an arylene group, heteroarylene group, aryltriyl group, or heteroaryltriyl group, more preferably a phenylene group, a biphenylene group, or a benzenetriyl group, still more preferably a biphenylene group, Or it is a benzenetriyl group. L ^O1 may have a substituent selected from the aforementioned substituent group A, and the alkyl group, aryl group, or cyano group is preferred as the substituent when it has a substituent. Specific examples of L ^O1 include the following.

n ^O1 represents an integer of 2 to 6, preferably an integer of 2 to 4, more preferably 2 or 3. n ^O1 is most preferably 3 from the viewpoint of device efficiency, and most preferably 2 from the viewpoint of device durability.
The compound represented by the general formula (O-1) is more preferably a compound represented by the following general formula (O-2).

(In the general formula (O-2), R ^O1 represents an alkyl group, an aryl group, or a heteroaryl group. R ^O2 to R ^O4 each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group. A ^O1 to A ^O4 each independently represent C—R ^A or a nitrogen atom, R ^A represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and a plurality of R ^A may be the same or different. May be.)

R ^O1 and ^{^A} O1 ^~ ^A ^O4, the general formula (O1) in the same meaning as ^{R O1} and ^{^A} O1 ^~ ^A ^O4 of, also the same preferable ranges thereof.
R ⁰² to R ⁰⁴ are each independently a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). These may have a substituent selected from the aforementioned substituent group A. R ⁰² to R ⁰⁴ are preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom or an aryl group, and most preferably a hydrogen atom.

The compound represented by the general formula (O-1) has a glass transition temperature (Tg) of 100 ° C. from the viewpoint of stable operation at high temperature storage, stable operation against high temperature driving, and heat generation during driving. It is preferably from ˜300 ° C., more preferably from 120 ° C. to 300 ° C., further preferably from 120 ° C. to 300 ° C., and still more preferably from 140 ° C. to 300 ° C.

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

The compound represented by the general formula (O-1) can be synthesized by the method described in JP-A No. 2001-335776. After synthesis, purification by column chromatography, recrystallization, reprecipitation, etc., followed by purification by sublimation is preferred. Not only can organic impurities be separated by sublimation purification, but inorganic salts, residual solvents, moisture, and the like can be effectively removed.

In the light emitting device of the present invention, the compound represented by the general formula (O-1) is contained in an organic layer between the light emitting layer and the cathode, but is contained in a layer on the cathode side adjacent to the light emitting layer. Is preferred.

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

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

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

The electron-accepting dopant in the hole injection layer is preferably contained in an amount of 0.01% by mass to 50% by mass, and preferably 0.1% by mass to 40% by mass with respect to the total mass of the compound forming the hole injection layer. %, More preferably 0.2% 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 receiving electrons from the cathode or the cathode side and transporting them to the anode side. The electron injection material and the electron transport material used for these layers may be a low molecular compound or a high molecular compound.
As the electron transport material, a compound represented by the general formula (1) or (2) of the present invention can be used. Other materials include pyridine derivatives, quinoline derivatives, pyrimidine derivatives, pyrazine derivatives, phthalazine derivatives, phenanthroline derivatives, triazine derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, fluorenone derivatives, anthraquinodimethane derivatives, Metal complexes of anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, naphthalene, perylene, and other aromatic ring tetracarboxylic anhydrides, phthalocyanine derivatives, 8-quinolinol derivatives And metal phthalocyanines, various metal complexes represented by metal complexes with benzoxazole and benzothiazole ligands, It is preferable that a layer containing a silane derivative, and the like.

The thicknesses of the electron injection layer and the electron transport layer are each preferably 500 nm or less from the viewpoint of lowering the driving voltage.
The thickness of the electron transport layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100 nm. The thickness of the electron injection layer is preferably from 0.1 nm to 200 nm, more preferably from 0.2 nm to 100 nm, and even more preferably from 0.5 nm to 50 nm.
The electron injection layer and the electron transport 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.

The electron injection layer preferably contains an electron donating dopant. By including an electron donating dopant in the electron injection layer, the electron injection property is improved, the driving voltage is lowered, and the efficiency is improved. The electron donating dopant may be any organic material or inorganic material as long as it can give electrons to the doped material and generate radical anions. For example, tetrathiafulvalene (TTF) And dithiaimidazole compounds such as tetrathianaphthacene (TTT) and bis- [1,3 diethyl-2-methyl-1,2-dihydrobenzimidazolyl], lithium, cesium and the like.

The electron donating dopant in the electron injection layer is preferably contained in an amount of 0.01% by mass to 50% by mass, and 0.1% by mass to 40% by mass with respect to the total mass of the compound forming the electron injection layer. More preferably, the content is 0.5 to 30% by mass.

(Hole blocking layer)
The hole blocking layer is a layer having a function of preventing holes transported from the anode side to the light emitting layer from passing through to the cathode side. In the present invention, a hole blocking layer can be provided as an organic layer adjacent to the light emitting layer on the cathode side.
Examples of organic compounds constituting the hole blocking layer include aluminum (III) bis (2-methyl-8-quinolinolato) 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 even more preferably 10 nm to 100 nm.
The hole 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.

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

(Protective layer)
In the present invention, the entire organic EL element may be protected by a protective layer.
As for the protective layer, the matters described in JP-A-2008-270736, paragraphs [0169] to [0170] can be applied to the present invention.

(Sealing container)
The element of this invention may seal the whole element using a sealing container.
Regarding the sealing container, the matters described in paragraph [0171] of JP-A-2008-270736 can be applied to the present invention.

(Drive)
The organic electroluminescence device of the present invention emits light by applying a direct current (which may include an alternating current component as necessary) voltage (usually 2 to 15 volts) or a direct current between the anode and the cathode. Obtainable.
The driving method of the organic electroluminescence device of the present invention is described in JP-A-2-148687, JP-A-6-301355, JP-A-5-290080, JP-A-7-134558, JP-A-8-234585, and JP-A-8-2441047. The driving methods described in each publication, Japanese Patent No. 2784615, US Pat. Nos. 5,828,429 and 6,023,308 can be applied.

The external quantum efficiency of the organic electroluminescent element of the present invention is preferably 7% or more, more preferably 10% or more, and further preferably 12% or more. The value of the external quantum efficiency should be the maximum value of the external quantum efficiency when the device is driven at 20 ° C., or the value of the external quantum efficiency around 300 to 400 cd / m ² when the device is driven at 20 ° C. Can do.

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

(Use of the element of the present invention)
The element of the present invention can be suitably used for a display element, a display, a backlight, electrophotography, an illumination light source, a recording light source, an exposure light source, a reading light source, a sign, a signboard, an interior, or optical communication. In particular, it is preferably used for a device driven in a region having a high light emission luminance, 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 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 (support substrate) 2, an organic electroluminescent element 10, a sealing container 16, 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 with an adhesive layer 14 interposed therebetween. In addition, a part of each

electrode

3 and 9, a partition, an insulating layer, etc. are abbreviate | omitted.
Here, as the adhesive layer 14, a photocurable adhesive such as an epoxy resin or a thermosetting adhesive can be used, and for example, a thermosetting adhesive sheet can also be used.

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

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

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

1. Synthesis Example (Synthesis Example 1) Synthesis of Compound 1

2,4-dichloroterephthalonitrile 1.97 g (10 mmol), 3-biphenylboronic acid 4.16 g (21 mmol), palladium acetate 0.22 g (1 mmol), triphenylphosphine 1.05 g (4 mmol), sodium carbonate 3. 18 g (30 mmol), 30 ml of toluene, and 15 ml of pure water were stirred at 100 ° C. for 6 hours under a nitrogen atmosphere. The reaction solution was allowed to cool to room temperature, ethyl acetate and pure water were added, and the deposited precipitate was collected by filtration. The obtained solid was recrystallized from tetrahydrofuran-isopropyl alcohol to obtain 1.88 g of Compound 1 (43% yield). By purifying the obtained crude product by sublimation, it was confirmed that the purity measured by HPLC was 99.93%.
¹ H NMR (400 MHz, inDMSO-d6); δ (ppm) = 8.47 (s, 2H), 8.01 (s, 2H), 7.87-7.67 (m, 10H), 7.53 (T, J = 7.6 Hz, 4H), 7.43 (t, J = 7.3 Hz, 2H).

(Synthesis Example 2) Synthesis of Compound 2 Compound 2 was synthesized in the same manner as in Synthesis Example 1 except that 3-biphenylboronic acid was replaced with 4-biphenylboronic acid in Synthesis Example 1.
¹ H NMR (400 MHz, inDMSO-d6); δ (ppm) = 8.36 (s, 2H), 7.92 (d, J = 8.4 Hz, 4H), 7.85-7.78 (m, 8H), 7.53 (t, J = 7.6 Hz, 4H), 7.44 (t, J = 7.2 Hz, 2H).

Synthesis Example 3 Synthesis of Compound 3 Compound 3 was synthesized in the same manner as in Synthesis Example 1 except that 3-biphenylboronic acid was replaced with 3- (3,5-diphenylphenyl) phenylboronic acid in Synthesis Example 1.
¹ H NMR (400 MHz, inDMSO-d6); δ (ppm) = 8.52 (s, 2H), 8.25 (s, 2H), 8.10-8.08 (m, 2H), 8.05 (S, 4H), 7.95 (s, 2H), 7.90 (d, J = 7.6 Hz, 8H), 7.80-7.72 (m, 4H), 7.53 (t, J = 7.6 Hz, 8H), 7.43 (t, J = 7.4 Hz, 4H).

(Synthesis Example 4) Synthesis of Compound 4 Compound 4 was synthesized in the same manner as in Synthesis Example 1 except that 3-biphenylboronic acid was replaced with 9-phenanthreneboronic acid in Synthesis Example 1.
¹ H NMR (400 MHz, inDMSO-d6); δ (ppm) = 9.04 (d, J = 8.4 Hz, 2H), 8.99 (d, J = 8.4 Hz, 2H), 8.50 ( s, 2H), 8.16-8.12 (m, 3H), 8.45 (s, 1H), 7.91-7.65 (m, 10H).

(Synthesis Example 5) Synthesis of Compound 5 Compound 5 was synthesized in the same manner as in Synthesis Example 1, except that 3-biphenylboronic acid was replaced with 2-triphenyleneboronic acid in Synthesis Example 1.
¹ H NMR (400 MHz, inDMSO-d6); δ (ppm) = 9.22 (s, 2H), 9.07 (d, J = 9.2 Hz, 2H), 9.03-9.00 (m, 2H), 8.98-8.93 (m, 2H), 8.92-8.87 (m, 4H), 8.69 (s, 2H), 8.8.12 (d, J = 8. 4 Hz, 2H), 7.83-7.76 (m, 8H).

Synthesis Example 6 Synthesis of Compound 6

9.85 g (50 mmol) of 2,4-dichloroterephthalonitrile, 11.1 g (50 mmol) of 9-phenanthreneboronic acid, 0.46 g (0.5 mmol) of tris (dibenzylideneacetone) dipalladium, 2-dicyclohexylphosphino- 0.82 g (2 mmol) of 2 ′, 6′-dimethoxybiphenyl (SPhos), 21.2 g (100 mmol) of potassium phosphate, 50 ml of dimethoxyethane, and 50 ml of pure water were stirred at 50 ° C. for 3 hours in a nitrogen atmosphere. The reaction solution was allowed to cool to room temperature, and the deposited precipitate was collected by filtration and washed with ethyl acetate, pure water, and ethanol. The obtained solid was further washed with ethyl acetate to obtain 9.1 g of Intermediate A (yield 54%).

Intermediate A 1.7 g (5 mmol), 1,4-phenylenediboronic acid 0.42 g (2.5 mmol), tris (dibenzylideneacetone) dipalladium 0.02 g (0.025 mmol), 2-dicyclohexylphosphino-2 0.04 g (0.1 mmol) of ', 6'-dimethoxybiphenyl (SPhos), 2.1 g (10 mmol) of potassium phosphate, 80 ml of tetrahydrofuran and 20 ml of pure water were stirred at 100 ° C. for 4 hours under a nitrogen atmosphere. The reaction solution was allowed to cool to room temperature, and then the deposited precipitate was collected by filtration and washed with tetrahydrofuran and pure water. The obtained solid was further washed with pure water and tetrahydrofuran to obtain 1.4 g of Compound 6 (yield 82%).
¹ H NMR (400 MHz, inDMSO-d6); δ (ppm) = 9.04 (d, J = 8.8 Hz, 2H), 8.98 (d, J = 8.8 Hz, 2H), 8.55 ( s, 2H), 8.47 (s, 2H), 8.13 (d, J = 7.4 Hz, 2H), 8.08 (s, 4H), 8.04 (s, 2H), 7.87 −7.60 (m, 10H).

Synthesis Example 7 Synthesis of Compound 7 Intermediate A 1.7 g (5 mmol), 4-p-terphenylboronic acid 1.4 g (5 mmol), tris (dibenzylideneacetone) dipalladium 0.02 g (0.025 mmol), 2-Dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl (SPhos) 0.04 g (0.1 mmol), potassium phosphate 2.1 g (10 mmol), tetrahydrofuran 80 ml, pure water 20 ml at 100 ° C. in a nitrogen atmosphere. Stir for 3 hours. The reaction solution was allowed to cool to room temperature, and then the deposited precipitate was collected by filtration and washed with tetrahydrofuran and pure water. The obtained solid was further washed with pure water and tetrahydrofuran to obtain 1.8 g of Compound 7 (yield 68%).
¹ H NMR (400 MHz, inDMSO-d6); δ (ppm) = 9.02 (d, J = 8.8 Hz, 1H), 8.97 (d, J = 8.0 Hz, 1H), 8.47 ( s, 1H), 8.41 (s, 1H), 8.11 (d, J = 6.6 Hz, 1H), 8.03-8.00 (m, 3H), 7.95-7.91 ( m, 4H), 7.86-7.74 (m, 7H), 7.68 (t, J = 7.8 Hz, 1H), 7.62 (d, J = 8.4 Hz, 1H), 7. 52 (t, J = 7.6 Hz, 2H), 7.41 (t, J = 7.5 Hz, 1H).

(Synthesis Example 8) Synthesis of Compound 8 In the same reaction as in Synthesis Example 6 and Synthesis Example 7, 9-phenanthreneboronic acid was converted to 4-tert-butylphenylboronic acid, and 4-p-terphenylboronic acid was converted to 2-triphenylene. Compound 8 was synthesized by changing to boronic acid.
¹ H NMR (400 MHz, inDMSO-d6); δ (ppm) = 9.16 (s, 1H), 9.02 (d, J = 8.8 Hz, 1H), 8.99-8.96 (m, 1H), 8.94-8.91 (m, 1H), 8.89-8.86 (m, 2H), 8.57 (s, 1H), 8.35 (s, 1H), 8.06 (D, J = 8.5 Hz, 1H), 7.82-7.75 (m, 4H), 7.70 (d, J = 8.4 Hz, 2H), 7.64 (d, J = 8. 4Hz, 2H).

Synthesis Example 9 Synthesis of Compound 9 Compound 9 was synthesized in the same manner as in Synthesis Example 7 except that 4-p-terphenylboronic acid was replaced with 2-triphenyleneboronic acid in Synthesis Example 7.
¹ H NMR (400 MHz, inDMSO-d6); δ (ppm) = 9.26 (s, 1H), 9.10-8.94 (m, 5H), 8.91-8.87 (m, 2H) , 8.71 (s, 1H), 8.47 (s, 1H), 8.17-8.13 (m, 2H), 8.05 (s, 1H), 7.87-7.63 (m , 9H).

(Synthesis Example 10) Synthesis of Compound 10 Compound 10 was synthesized in the same manner as in Synthesis Example 1, except that 3-biphenylboronic acid was replaced with 3- (2-triphenylenyl) phenylboronic acid in Synthesis Example 1.
¹ H NMR (400 MHz, inDMSO-d6); δ (ppm) = 9.19 (s, 2H), 9.09-9.05 (m, 2H), 8.97 (d, J = 9.2 Hz, 2H), 8.92-8.83 (m, 6H), 8.61 (s, 2H), 8.38 (s, 2H), 8.22-8.17 (m, 4H), 7.84 -7.72 (m, 12H).

(Synthesis Example 11) Synthesis of Compound 11 Compound 11 was synthesized in the same manner as in Synthesis Example 1 except that 3-biphenylboronic acid was replaced with 9,9-dimethylfluorene-2-boronic acid in Synthesis Example 1.
¹ H NMR (400 MHz, inDMSO-d6); δ (ppm) = 8.40 (s, 2H), 8.06 (d, J = 8.0 Hz, 2H), 7.97-7.94 (m, 4H), 7.73 (d, J = 8.0 Hz, 2H), 7.63-7.61 (m, 2H), 7.43-7.38 (m, 2H).

2. Element Evaluation The performance of each element of Examples and Comparative Examples described below was evaluated as follows.

(A) External quantum efficiency Using a source measure unit 2400 manufactured by Toyo Technica, a direct current voltage was applied to each element to emit light, and the luminance was measured using a luminance meter BM-8 manufactured by Topcon Corporation. The emission spectrum and emission wavelength were measured using a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics. Based on these, the external quantum efficiency at a luminance of around 1000 cd / m ² was calculated by the luminance conversion method. The higher the number, the better the efficiency.
(B) Drive voltage The drive voltage was the applied voltage when a DC voltage was applied to each element so that the luminance was 1000 cd / m ² . The driving voltage is preferably as small as possible.
(C) Device Durability An indication of drive durability is the time required to continue to emit light by applying a DC voltage so that the luminance shown in each example of device creation described below is obtained, and to reduce the luminance to a certain luminance. It was. The larger the number, the better the durability.

3. Element Preparation Example All materials used for element preparation were subjected to sublimation purification, and it was confirmed by high performance liquid chromatography (Tosoh TSKgel ODS-100Z) that the purity (absorption intensity area ratio at 254 nm) was 99.9% or more.
In addition, the parentheses written next to the headings of the following examples indicate the emission color and which material the compound of the present invention was used. Here, “ETL” means an electron transport material.

<Element creation example 1> (Red host)
A glass substrate having a thickness of 0.5 mm and a 2.5 cm square ITO film (manufactured by Geomat Co., Ltd., surface resistance 10 Ω / □) is placed in a cleaning container, subjected to ultrasonic cleaning in 2-propanol, and then subjected to UV-ozone treatment for 30 minutes. Went. The following organic compound layers were sequentially deposited on the transparent anode (ITO film) by vacuum deposition.
First layer: LG101: film thickness 10 nm
Second layer: NPD: film thickness 30 nm
Third layer: Compound 1 and RD-1 (mass ratio 90:10): film thickness 30 nm
Fourth layer: BAlq: film thickness 5 nm
Fifth layer: Alq: film thickness 45 nm
On this, 1 nm of lithium fluoride and 70 nm of metal aluminum were vapor-deposited in this order, and it was set as the cathode.
This is put in a glove box substituted with nitrogen gas without being exposed to the atmosphere, and sealed using a glass sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.). Thus, the device of Example 1 was obtained. Similarly, in place of the compound 1 used in the third layer of Example 1, by using the third layer material shown in Table 1 below and using the material shown in Table 1 as the material of the fourth layer, Devices of Examples 2 to 15 and Comparative Examples 1 to 5 were obtained. Durability shown in the tables, the luminance of each element and time taken until the 3000 cd / ^{m 2} to 2700cd / ^{m 2,} showing a device of Example 1 at 1 and a relative value.

In Table 1, since the element of Comparative Example 4 did not emit light, the efficiency, drive voltage and durability could not be evaluated correctly. While the element of Comparative Example 4 is not clear why not emit light, the T ₁ energy of the comparative compound 4 is presumed to smaller than the T ₁ energy of the luminescent material was quenched.

<Element creation example 2> (Red ETL)
A device was produced in the same manner as in Example 1 except that the layer configuration was changed to the following, and the device of Example 16 was obtained. Similarly, by using the material shown in Table 2 as the material of the fourth layer, devices of Examples 17 to 19 and Comparative Examples 6 and 7 were obtained. Efficiency, drive voltage, and durability were evaluated in the same manner as in Example 1. Durability was expressed as a relative value with the element of Example 16 as 1.
First layer: LG101: film thickness 10 nm
Second layer: NPD: film thickness 30 nm
Third layer: BAlq and RD-2 (mass ratio 95: 5): film thickness 30 nm
Fourth layer: Compound 1: thickness 5 nm
Fifth layer: Alq: film thickness 45 nm

<Element creation example 3> (Green host)
A device was produced in the same manner as in Example 1 except that the layer configuration was changed to the following, and the device of Example 20 was obtained. Similarly, the material shown in Table 3 was used as the material of the third layer of Example 20, and the fourth layer material shown in Table 3 below was used instead of Compound 1 used in the fourth layer. By using the material shown in Table 3 as the material of the layer, devices of Examples 21 to 24 and Comparative Examples 8 to 11 were obtained. The durability was expressed as a relative value with the time taken for the luminance of each element to reach from 5000 cd / m ² to 4500 cd / m ² , with the element of Example 20 taken as 1. The efficiency and driving voltage were evaluated in the same manner as in Example 1.
First layer: CuPc: film thickness 10 nm
Second layer: NPD: film thickness 25 nm
Third layer: NPD: film thickness 5 nm
Fourth layer: Compound 1 and GD-1 (mass ratio 90:10): film thickness 30 nm
5th layer: ET-3: 5 nm thickness
Sixth layer: Alq: film thickness 45 nm

In Table 3, since the device of Comparative Example 10 did not emit light, the efficiency, drive voltage and durability could not be evaluated correctly. While the element of Comparative Example 10 is not clear why not emit light, the T ₁ energy of the comparative compound 4 is presumed to smaller than the T ₁ energy of the luminescent material was quenched.

<Element creation example 4> (Green ETL)
A device was produced in the same manner as in Example 20 except that the layer configuration was changed to the following, and the device of Example 25 was obtained. Similarly, by using the material shown in Table 4 as the material of the fifth layer, devices of Examples 26 to 28 and Comparative Examples 12 and 13 were obtained. Efficiency, drive voltage, and durability were evaluated in the same manner as in Example 20. Durability was expressed as a relative value with the element of Example 25 as 1.
First layer: 2-TNATA and F ₄ -TCNQ (mass ratio 99.7: 0.3): film thickness 160 nm
Second layer: NPD: film thickness 5 nm
Third layer: HT-1: film thickness 3 nm
Fourth layer: mCBP and GD-2 (mass ratio 85:15): film thickness 30 nm
Fifth layer: Compound 1: film thickness 5 nm
Sixth layer: BCP and Li (mass ratio 99.4: 0.6): film thickness 25 nm

<Element creation example 5> (Blue ETL)
A device was produced in the same manner as in Example 1 except that the layer configuration was changed to the following, and the device of Example 29 was obtained. Similarly, by using the material shown in Table 5 as the material of the fourth layer, devices of Examples 30 to 33 and Comparative Examples 14 and 15 were obtained. The durability was expressed as a relative value with the time taken for the luminance of each element to reach from 1000 cd / m ² to 500 cd / m ² , with the element of Example 29 taken as 1. Efficiency and drive voltage were evaluated in the same manner as in Example 1.
First layer: CuPc: film thickness 10 nm
Second layer: TPAC: film thickness 30 nm
Third layer: mCBP and BD-1 (mass ratio 90:10): film thickness 30 nm
Fourth layer: Compound 1: thickness 5 nm
5th layer: ET-2: film thickness 25 nm

From the results of Tables 1 to 5, it can be seen that the durability of the device of the example using the compound of the present invention is significantly improved as compared with the device of the comparative example.

The structures of the compounds used in Examples and Comparative Examples are shown below.

Although the present invention has been described in detail and with reference to specific embodiments, it will be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the invention.
This application is based on a Japanese patent application filed on July 29, 2010 (Japanese Patent Application No. 2010-171229), the contents of which are incorporated herein by reference.

DESCRIPTION OF SYMBOLS 2 ... Substrate 3 ... Anode 4 ... Hole injection layer 5 ... Hole transport layer 6 ... Light emitting layer 7 ... Hole block layer 8 ... Electron transport layer 9 ...・ Cathode 10: Organic electroluminescent 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 Output surface 31 ... Transparent substrate 32 ... Fine particle 40 ... Illumination device

Claims

An organic electroluminescent device comprising a substrate and a pair of electrodes comprising an anode and a cathode, and at least one organic layer including a light emitting layer between the electrodes, wherein at least one of the at least one organic layer An organic electroluminescent device comprising at least one compound represented by the following general formula (1).

In the general formula (1), R 11 and R 15 each independently represent a hydrogen atom or an alkyl group, or R 11 is bonded to R 12 and R 15 is bonded to R 14 to form a substituent C A naphthalene ring, a phenanthrene ring, a triphenylene ring, or a fluorene ring, which may have
R 12 , R 13 and R 14 are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, a cyano group, a phenyl group which may have a substituent C, or a naphthyl which may have a substituent C. A phenanthrenyl group which may have a group, a substituent C, a triphenylenyl group which may have a substituent C, or a fluorenyl group which may have a substituent C; R 12 and R 13 , and R 13 and R 14 may be bonded to each other to form a naphthalene ring, a phenanthrene ring, a triphenylene ring, or a fluorene ring, which may have a substituent C.
n represents 1, 2 or 3.
When n is 2 or 3, the plurality of R 11 to R 15 may be the same or different.
Substituent C is an alkyl group, cycloalkyl group, cyano group, phenyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, or fluorenyl group, and substituent C is a phenyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, or In the case of a fluorenyl group, these groups may further have the substituent C.
The organic electroluminescent element according to claim 1, wherein n is 2 in the general formula (1).
The organic electroluminescence device according to claim 1 or 2, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (2).

In the general formula (2), R 21 , R 25 , R 26 and R 30 each independently represent a hydrogen atom or an alkyl group, or R 21 represents R 22 , R 25 represents R 24 , R 26 R 27 and R 30 are each bonded to R 29 to form a naphthalene ring, phenanthrene ring, triphenylene ring or fluorene ring which may have a substituent C.
R 22 , R 23 , R 24 , R 27 , R 28 and R 29 are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, a cyano group, a phenyl group optionally having substituent C, or a substituent. A naphthyl group optionally having C, a phenanthrenyl group optionally having a substituent C, a triphenylenyl group optionally having a substituent C, or a fluorenyl group optionally having a substituent C Represents. R 22 and R 23 , R 23 and R 24 , R 27 and R 28 , and R 28 and R 29 may be bonded to each other and may have a substituent C, a naphthalene ring, a phenanthrene ring, a triphenylene ring Or you may form a fluorene ring.
Substituent C is an alkyl group, cycloalkyl group, cyano group, phenyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, or fluorenyl group, and substituent C is a phenyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, or In the case of a fluorenyl group, these groups may further have the substituent C.
In the general formula (2), R 21 and R 26, R 22 and R 27, R 23 and R 28, R 24 and R 29, and R 25 and R 30, but is identical, respectively, according to claim 3 Organic electroluminescent element.
The organic electroluminescent element according to any one of claims 1 to 4, wherein the light emitting layer contains at least one phosphorescent material.
6. The organic electroluminescent element according to claim 1, wherein the phosphorescent material is an iridium complex represented by the following general formula (E-1).

In general formula (E-1), Z 1 and Z 2 each independently represent a carbon atom or a nitrogen atom.
A 1 represents an atomic group that forms a 5- or 6-membered heterocycle with Z 1 and a nitrogen atom.
B 1 represents an atomic group that forms a 5- or 6-membered ring with Z 2 and a carbon atom.
(XY) represents a monoanionic bidentate ligand.
n E1 represents an integer of 1 to 3.
The organic electroluminescence device according to any one of claims 1 to 6, wherein the compound represented by the general formula (1) or (2) is contained in the light emitting layer.
The organic electroluminescent element according to any one of claims 1 to 7, wherein the compound represented by the general formula (1) or (2) is used in a layer between the light emitting layer and the cathode.
A light emitting device using the organic electroluminescent element according to any one of claims 1 to 8.
A display device using the organic electroluminescent element according to any one of claims 1 to 8.
An illumination device using the organic electroluminescent element according to any one of claims 1 to 8.
A compound represented by the following general formula (1).

In the general formula (1), R 11 and R 15 each independently represent a hydrogen atom or an alkyl group, or R 11 is bonded to R 12 and R 15 is bonded to R 14 to form a substituent C A naphthalene ring, a phenanthrene ring, a triphenylene ring, or a fluorene ring, which may have
R 12 , R 13 and R 14 are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, a cyano group, a phenyl group which may have a substituent C, or a naphthyl which may have a substituent C. A phenanthrenyl group which may have a group, a substituent C, a triphenylenyl group which may have a substituent C, or a fluorenyl group which may have a substituent C; R 12 and R 13 , and R 13 and R 14 may be bonded to each other to form a naphthalene ring, a phenanthrene ring, a triphenylene ring, or a fluorene ring, which may have a substituent C.
n represents 1, 2 or 3.
When n is 2 or 3, the plurality of R 11 to R 15 may be the same or different.
Substituent C is an alkyl group, cycloalkyl group, cyano group, phenyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, or fluorenyl group, and substituent C is a phenyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, or In the case of a fluorenyl group, these groups may further have the substituent C.
The compound according to claim 12, wherein n is 2 in the general formula (1).
The compound of Claim 12 or 13 which is a compound represented by following General formula (2).

In the general formula (2), R 21 , R 25 , R 26 and R 30 each independently represent a hydrogen atom or an alkyl group, or R 21 represents R 22 , R 25 represents R 24 , R 26 R 27 and R 30 are each bonded to R 29 to form a naphthalene ring, phenanthrene ring, triphenylene ring or fluorene ring which may have a substituent C.
R 22 , R 23 , R 24 , R 27 , R 28 and R 29 are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, a cyano group, a phenyl group optionally having substituent C, or a substituent. A naphthyl group optionally having C, a phenanthrenyl group optionally having a substituent C, a triphenylenyl group optionally having a substituent C, or a fluorenyl group optionally having a substituent C Represents. R 22 and R 23 , R 23 and R 24 , R 27 and R 28 , and R 28 and R 29 may be bonded to each other and may have a substituent C, a naphthalene ring, a phenanthrene ring, a triphenylene ring Or you may form a fluorene ring.
Substituent C is an alkyl group, cycloalkyl group, cyano group, phenyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, or fluorenyl group, and substituent C is a phenyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, or In the case of a fluorenyl group, these groups may further have the substituent C.
In the general formula (2), R 21 and R 26, R 22 and R 27, R 23 and R 28, R 24 and R 29, and R 25 and R 30, but is identical, respectively, according to claim 14 Compound.
A composition containing the compound represented by the general formula (1) or (2) according to any one of claims 12 to 15.
A thin film containing the compound represented by the general formula (1) or (2) according to any one of claims 12 to 15.