JP6113136B2 - Organic electroluminescent device, and charge transport material and compound having m-kinkphenyl structure - Google Patents

Description

  The present invention relates to an organic electroluminescent device, and a charge transport material and compound having an m-kinkphenyl structure.

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

  In recent years, the use of phosphorescent light emitting materials has led to higher efficiency of devices. Patent Document 1 discloses the use of a benzonitrile-based charge transport material having a substituent at the ortho position for further improving the light emission efficiency of the device and reducing the driving voltage. Further, Patent Documents 2 to 4 describe organic electroluminescent elements using an aromatic compound having a specific structure as a charge transport material.

  In addition, as a compound having an m-kinkphenyl structure of the present invention, a molecular model calculated as a nonlinear optical material is described in Non-Patent Document 1, but there is no description of a synthesis example of an actual compound. There is no description or suggestion of applying the model compounds to charge transport materials or organic electroluminescent devices.

JP 2007-266598 A JP 2006-135160 A JP 2006-135184 A JP 2006-190718 A

J. et al. Am. Chem. Soc. , 1998, 120, 13517-13518

  As a result of studies by the present inventors, the conventional devices described in Patent Documents 1 to 4 have problems that the luminous efficiency decreases when stored at a high temperature, the chromaticity changes greatly, and the durability deteriorates. This has been newly clarified by the study by the present inventors, and an improvement has been demanded. In particular, there is a demand for an element whose characteristics do not change even after high-temperature storage, such as in-vehicle use. The devices using comparative compounds 1 to 11 shown in the examples to be described later, which have been reported so far, all have low efficiency and large chromaticity when driven after storage at 100 ° C. for 24 hours. There were problems such as changes and low durability. In order to solve these problems of the conventional device, the present inventors use the charge transport material having an m-kinkphenyl structure of the present invention to suppress the decrease in luminous efficiency after storage of the device at high temperature, and the chromaticity. It has been found that an organic electroluminescence device satisfying all of the suppression of change and the improvement of durability at a high level is provided.

That is, an object of the present invention is to provide an organic electroluminescent device that satisfies all of the suppression of a decrease in luminous efficiency after storage at high temperature of the device, the suppression of chromaticity change, and the improvement of durability at a high level. is there.
Another object of the present invention is to provide a compound and a charge transport material useful for the organic electroluminescence device described above. 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 of the present inventors, by using a charge transport material having a specific m-kinkphenyl structure, suppression of decrease in luminous efficiency after storage of the device at high temperature, suppression of chromaticity change, and improvement of durability It was found that an organic electroluminescent device satisfying all of the above conditions at a high level is provided.

That is, the present invention can be achieved by the following means.
[1] An organic electroluminescent device having a pair of electrodes consisting of an anode and a cathode and at least one organic layer including a light emitting layer between the electrodes on a substrate,
Organic electroluminescence comprising a compound having an m-kinkphenyl structure represented by the following general formula (1) in any one of the at least one organic layer: element.

In general formula (1), R ₁ represents an alkyl group or an aryl group. However, the aryl group represented by R ₁ does not have a condensed ring and may have an alkyl group or a cyano group. When R ₁ there are a plurality, the plurality of R ₁ may be the same or different.
m ₁ is the number of cyano groups substituted in the m-kinkphenyl structure in the general formula (1), and represents an integer of 0 or more and 10 or less.
n ₁ is the number of R ₁ substituted with the m-kinkphenyl structure in the general formula (1), and represents an integer of 0 or more and 22 or less. Here, m ₁ + n ₁ is an integer of 1 or more and 22 or less.
However, the compound represented by the general formula (1) does not have a benzene ring substituted with three or more cyano groups, has at least one cyano group substituted on the benzene ring, and It has a cyano group and R ₁ so that the sum of the number of benzene rings and the number of cyano groups substituted on the benzene ring is 9 or more and 20 or less.

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

In general formula (2), R ₂ represents an alkyl group or an aryl group. However, the aryl group represented by R ₂ does not have a condensed ring and may have an alkyl group or a cyano group. When R ₂ there are a plurality, the plurality of R ₂ may be the same or different.
m ₂ is the number of cyano groups substituted on the biphenyl-m-kinkphenyl structure in the general formula (2), and represents an integer of 0 to 14.
n ₂ is the general formula (2) is the number of _{R 2} substituted biphenyl -m- kink phenyl structure in an integer of 0 or more and 30 or less. _Here, m ₂ + _n 2 is 1 to 30 integer.
However, the compound represented by the general formula (2) does not have a benzene ring substituted with three or more cyano groups, has at least one cyano group substituted on the benzene ring, and It has a cyano group and R ₂ so that the sum of the number of benzene rings and the number of cyano groups substituted on the benzene ring is 9 or more and 20 or less.

[3] The organic electroluminescent element according to the above [1], wherein the compound represented by the general formula (1) is represented by the following general formula (3).

In general formula (3), R ₃ represents an alkyl group or an aryl group. However, the aryl group represented by R ₃ does not have a condensed ring and may have an alkyl group or a cyano group. When R ₃ there are a plurality, the plurality of R ₃ may be the same or different.
m ₃ is the number of cyano groups substituted on the diphenyl-m-kinkphenyl structure in the general formula (3), and represents an integer of 0 or more and 14 or less.
n ₃ is the general formula (3) is the number of _{R 3} substituted diphenyl -m- kink phenyl structure in an integer of 0 or more and 30 or less. Here, m ₃ + n ₃ is an integer of 1 or more and 30 or less.
However, the compound represented by the general formula (3) does not have a benzene ring substituted with 3 or more cyano groups, has at least one cyano group substituted on the benzene ring, and It has a cyano group and R ₃ so that the sum of the number of benzene rings and the number of cyano groups substituted on the benzene ring is 9 or more and 20 or less.

[4] The organic electroluminescent element according to any one of [1] to [3], 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.
[5] The organic electroluminescent element according to the above [4], wherein the iridium complex represented by the general formula (E-1) is represented by the following 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.
[6] The organic electroluminescent element according to the above [4], wherein the iridium complex represented by the general formula (E-1) is represented by the following general formula (E-6).

In General Formula (E-6), R _{1a to} R _1k 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 may be represented, 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.
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 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.
(X—Y) represents a monoanionic bidentate ligand.
n _E6 represents an integer of 1 to 3.

[7] An organic layer adjacent to the light emitting layer is provided between the light emitting layer and the cathode, and the organic layer contains a compound represented by any one of the general formulas (1) to (3). The organic electroluminescent element according to any one of [1] to [6] above.
[8] The organic electroluminescent element according to any one of [1] to [7], wherein the light emitting layer contains a compound represented by any one of the general formulas (1) to (3).
[9] The electron injection layer adjacent to the cathode between the pair of electrodes, the electron injection layer containing the compound represented by any one of the general formulas (1) to (3) [1] The organic electroluminescent element according to any one of [8].
[10] The organic electroluminescent element as described in [9] above, wherein the electron injection layer further contains an electron donating dopant.
[11] The organic electroluminescent element as described in any one of [1] to [10], wherein at least one organic layer between the pair of electrodes is formed by a solution coating method.
[12] A light emitting device using the organic electroluminescent element according to any one of [1] to [11].
[13] A display device using the organic electroluminescent element according to any one of [1] to [11].
[14] An illumination device using the organic electroluminescent element according to any one of [1] to [11].

[15] A charge transport material represented by the following general formula (1).

In general formula (1), R ₁ represents an alkyl group or an aryl group. However, the aryl group represented by R ₁ does not have a condensed ring and may have an alkyl group or a cyano group. When R ₁ there are a plurality, the plurality of R ₁ may be the same or different.
m ₁ is the number of cyano groups substituted in the m-kinkphenyl structure in the general formula (1), and represents an integer of 0 or more and 10 or less.
n ₁ is the number of R ₁ substituted with the m-kinkphenyl structure in the general formula (1), and represents an integer of 0 or more and 22 or less. Here, m ₁ + n ₁ is an integer of 1 or more and 22 or less.
However, the compound represented by the general formula (1) does not have a benzene ring substituted with three or more cyano groups, has at least one cyano group substituted on the benzene ring, and It has a cyano group and R ₁ so that the sum of the number of benzene rings and the number of cyano groups substituted on the benzene ring is 9 or more and 20 or less.

[16] The charge transport material according to [15], which is represented by the following general formula (2).

In general formula (2), R ₂ represents an alkyl group or an aryl group. However, the aryl group represented by R ₂ does not have a condensed ring and may have an alkyl group or a cyano group. When R ₂ there are a plurality, the plurality of R ₂ may be the same or different.
m ₂ is the number of cyano groups substituted on the biphenyl-m-kinkphenyl structure in the general formula (2), and represents an integer of 0 to 14.
n ₂ is the general formula (2) is the number of _{R 2} substituted biphenyl -m- kink phenyl structure in an integer of 0 or more and 30 or less. _Here, m ₂ + _n 2 is 1 to 30 integer.
However, the compound represented by the general formula (2) does not have a benzene ring substituted with three or more cyano groups, has at least one cyano group substituted on the benzene ring, and It has a cyano group and R ₂ so that the sum of the number of benzene rings and the number of cyano groups substituted on the benzene ring is 9 or more and 20 or less.

[17] The charge transport material according to [15], which is represented by the following general formula (3).

In general formula (3), R ₃ represents an alkyl group or an aryl group. However, the aryl group represented by R ₃ does not have a condensed ring and may have an alkyl group or a cyano group. When R ₃ there are a plurality, the plurality of R ₃ may be the same or different.
m ₃ is the number of cyano groups substituted on the diphenyl-m-kinkphenyl structure in the general formula (3), and represents an integer of 0 or more and 14 or less.
n ₃ is the general formula (3) is the number of _{R 3} substituted diphenyl -m- kink phenyl structure in an integer of 0 or more and 30 or less. Here, m ₃ + n ₃ is an integer of 1 or more and 30 or less.
However, the compound represented by the general formula (3) does not have a benzene ring substituted with 3 or more cyano groups, has at least one cyano group substituted on the benzene ring, and It has a cyano group and R ₃ so that the sum of the number of benzene rings and the number of cyano groups substituted on the benzene ring is 9 or more and 20 or less.

[18] A composition comprising the charge transport material according to any one of [15] to [17].
[19] A thin film containing the charge transport material according to any one of [15] to [17].

[20] A compound represented by the following general formula (1).

In general formula (1), R ₁ represents an alkyl group or an aryl group. However, the aryl group represented by R ₁ does not have a condensed ring and may have an alkyl group or a cyano group. When R ₁ there are a plurality, the plurality of R ₁ may be the same or different.
m ₁ is the number of cyano groups substituted in the m-kinkphenyl structure in the general formula (1), and represents an integer of 0 or more and 10 or less.
n ₁ is the number of R ₁ substituted with the m-kinkphenyl structure in the general formula (1), and represents an integer of 0 or more and 22 or less. Here, m ₁ + n ₁ is an integer of 1 or more and 22 or less.
However, the compound represented by the general formula (1) does not have a benzene ring substituted with three or more cyano groups, has at least one cyano group substituted on the benzene ring, and It has a cyano group and R ₁ so that the sum of the number of benzene rings and the number of cyano groups substituted on the benzene ring is 9 or more and 20 or less.

[21] The compound according to [20], which is represented by the following general formula (2).

In general formula (2), R ₂ represents an alkyl group or an aryl group. However, the aryl group represented by R ₂ does not have a condensed ring and may have an alkyl group or a cyano group. When R ₂ there are a plurality, the plurality of R ₂ may be the same or different.
m ₂ is the number of cyano groups substituted on the biphenyl-m-kinkphenyl structure in the general formula (2), and represents an integer of 0 to 14.
n ₂ is the general formula (2) is the number of _{R 2} substituted biphenyl -m- kink phenyl structure in an integer of 0 or more and 30 or less. _Here, m ₂ + _n 2 is 1 to 30 integer.
However, the compound represented by the general formula (2) does not have a benzene ring substituted with three or more cyano groups, has at least one cyano group substituted on the benzene ring, and It has a cyano group and R ₂ so that the sum of the number of benzene rings and the number of cyano groups substituted on the benzene ring is 9 or more and 20 or less.

[22] The compound according to [20], represented by the following general formula (3).

In general formula (3), R ₃ represents an alkyl group or an aryl group. However, the aryl group represented by R ₃ does not have a condensed ring and may have an alkyl group or a cyano group. When R ₃ there are a plurality, the plurality of R ₃ may be the same or different.
m ₃ is the number of cyano groups substituted on the diphenyl-m-kinkphenyl structure in the general formula (3), and represents an integer of 0 or more and 14 or less.
n ₃ is the general formula (3) is the number of _{R 3} substituted diphenyl -m- kink phenyl structure in an integer of 0 or more and 30 or less. Here, m ₃ + n ₃ is an integer of 1 or more and 30 or less.
However, the compound represented by the general formula (3) does not have a benzene ring substituted with 3 or more cyano groups, has at least one cyano group substituted on the benzene ring, and It has a cyano group and R ₃ so that the sum of the number of benzene rings and the number of cyano groups substituted on the benzene ring is 9 or more and 20 or less.

  ADVANTAGE OF THE INVENTION According to this invention, the organic electroluminescent element which satisfies all of suppression of the fall of the luminous efficiency after high temperature storage of an element, suppression of a chromaticity change, and improvement of durability can be provided at a high level.

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 description of the following general formulas (1) to (3), a hydrogen atom includes an isotope (deuterium atom and the like), and an atom constituting a substituent further includes the isotope.
In the present invention, when referred to as “substituent”, the substituent may be substituted. For example, the term “alkyl group” in the present invention includes an alkyl group substituted with a fluorine atom (for example, trifluoromethyl group) and an alkyl group substituted with an aryl group (for example, triphenylmethyl group). When the term “alkyl group having 1 to 6 carbon atoms” is used, it means that the number of carbon atoms is 1 to 6 as all groups including those substituted.

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

(Substituent group B)
An alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, for example vinyl , Allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as propargyl , 3-pentynyl, etc.), an aryl group (preferably having 6 to 30 carbon atoms, more preferably carbon 6 to 20, particularly preferably 6 to 12 carbon atoms, including, for example, phenyl, p-methylphenyl, naphthyl, anthranyl, 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, benzimidazo , Benzothiazolyl, carbazolyl group, azepinyl group, silylyl group, etc.) These substituents may be further substituted, and further substituents are groups selected from the substituent group B described above. Can be mentioned.

<Substituent Z '>
An alkyl group (preferably having 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, still more preferably 1 to 4 carbon atoms, such as methyl, ethyl, isopropyl, n-propyl, tert-butyl, isobutyl, n- Butyl, neopentyl, n-pentyl, n-hexyl, cyclopropyl, cyclopentyl, cyclohexyl and the like), an alkenyl group (preferably having 2 to 8 carbon atoms, more preferably 2 to 5 carbon atoms, such as vinyl) And aryl groups (having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, such as phenyl group, naphthyl group, anthracenyl group, tetracenyl group, pyrenyl group, perylenyl group, triphenylenyl group, and chrysenyl group). Heteroaryl group (preferably having 4 to 30 carbon atoms, more preferably carbon 4 to 20, for example, pyridine, pyrazine, pyrimidine, pyridazine, triazine, thiophene, furan, oxazole, thiazole, imidazole, pyrazole, triazole, oxadiazole, thiadiazole, etc.), alkoxy group (preferably having 1 carbon atom) To 8, more preferably 1 to 5 carbon atoms, such as a methoxy group, an ethoxy group, an n-propyloxy group, and an iso-propyloxy group), a phenoxy group, a halogen atom (preferably a fluorine atom), A silyl group (preferably having 4 to 30 carbon atoms, more preferably 4 to 20 carbon atoms, such as trimethylsilyl group, triethylsilyl group, triphenylsilyl group), amino group (preferably having 2 to 60 carbon atoms, More preferably, it has 2 to 40 carbon atoms, and dimethyl Amino group, a diethylamino group, and a diphenylamino group), a cyano group or a group formed by combining these groups, a plurality of substituents Z 'may form an aryl ring bonded to each other. Examples of the aryl ring formed by bonding a plurality of substituents Z ′ to each other include a phenyl ring and a pyridine ring, and a phenyl ring is preferable.

  The organic electroluminescent device of the present invention is an organic electroluminescent device having a pair of electrodes comprising an anode and a cathode and at least one organic layer including a light emitting layer between the electrodes on the substrate, wherein the light emitting layer And at least one of the at least one organic layer contains a compound having an m-kinkphenyl structure represented by the following general formula (1).

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

In general formula (1), R ₁ represents an alkyl group or an aryl group. However, the aryl group represented by R ₁ does not have a condensed ring and may have an alkyl group or a cyano group. When R ₁ there are a plurality, the plurality of R ₁ may be the same or different.
m ₁ is the number of cyano groups substituted in the m-kinkphenyl structure in the general formula (1), and represents an integer of 0 or more and 10 or less.
n ₁ is the number of R ₁ substituted with the m-kinkphenyl structure in the general formula (1), and represents an integer of 0 or more and 22 or less. Here, m ₁ + n ₁ is an integer of 1 or more and 22 or less.
However, the compound represented by the general formula (1) does not have a benzene ring substituted with three or more cyano groups, has at least one cyano group substituted on the benzene ring, and It has a cyano group and R ₁ so that the sum of the number of benzene rings and the number of cyano groups substituted on the benzene ring is 9 or more and 20 or less.

The alkyl group represented by R ₁ is a linear, branched, or cyclic alkyl group and does not have a substituent such as a fluorine atom or a cyano group. That is, the alkyl group represented by R ₁ is an unsubstituted alkyl group. The alkyl group represented by R ₁ 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. . The alkyl group represented by R ₁ is 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. Group, t-amyl group, s-isoamyl group, cyclopentyl group, n-hexyl group, and cyclohexyl group, and most preferably methyl group, i-propyl group, n-butyl group, and t-butyl group. One of them.

The aryl group represented by R ₁ is an aryl group having no condensed ring such as a benzene ring or an anthracene ring. The aryl group represented by R ₁ does not include a heteroaryl group containing a hetero atom such as a nitrogen atom, a sulfur atom, or an oxygen atom. That is, the aryl group represented by R ₁ does not have a heterocycle. The aryl group represented by R ₁ typically has one monocyclic aromatic hydrocarbon or a ring carbon atom of an aromatic hydrocarbon in which a plurality of monocyclic aromatic hydrocarbons are connected to each other by a single bond. From the above, it is a monovalent group formed by removing one hydrogen atom, preferably 1 to 5 aromatic rings, more preferably 1 to 3 aromatic rings. The aromatic ring contained in the aryl group represented by R ₁ is preferably a benzene ring. The aryl group represented by R ₁ may be substituted with the aforementioned alkyl group or cyano group. The aryl group represented by R ₁ is preferably a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, or a kinkphenyl group, which may be substituted with an alkyl group or a cyano group, and more preferably an alkyl group. A phenyl group, a biphenyl group, or a terphenyl group, which may be substituted with a group or a cyano group. When the aryl group represented by R ₁ includes a plurality of benzene rings, the plurality of benzene rings are preferably linked at the meta position (m-). The preferred range of the alkyl group that may be substituted on the aryl group represented by R ₁ is the same as the preferred range of the alkyl group represented by R ₁ described above.

m ₁ is the number of cyano groups substituted on the m-kinkphenyl structure in the general formula (1), that is, five benzene rings linked at the meta position shown as the structural formula in the general formula (1), Represents an integer of 0 to 10. The substitution referred to here means a state in which any one hydrogen atom on the five benzene rings is replaced by a cyano group, and the cyano group optionally substituted by the aryl group represented by R ₁ described above. Is not included in the number of m ₁ . Further, as will be described later, three or more cyano groups are not substituted on any one of the five benzene rings.
In the present invention, the cyano group substituted on m- kink phenyl structure of the general formula (1) in terms of charge-transporting property and chemical stability exists at least one (i.e., m ₁ is 1 to 10 preferably of an integer that) is, more preferably m ₁ is 1 to 5 integer, more preferably from 1 to 3 of an integer.

n ₁ is the number of R ₁ substituted with the m-kinkphenyl structure in the general formula (1), that is, five benzene rings linked at the meta position shown as the structural formula in the general formula (1), Represents an integer of 0 or more and 22 or less. n ₁ is preferably an integer of 1 to 5 and more preferably an integer of 1 to 3 from the viewpoint of charge transportability and chemical stability.

The compound represented by the general formula (1) has at least one cyano group substituted on the benzene ring. The cyano group referred to here is not particularly limited as long as it is substituted on the benzene ring, and may be one of the cyano groups counted by m ₁ or the benzene ring in the aryl group represented by R _1. A cyano group substituted with may be used. By having a chemically stable cyano group as an electron withdrawing group in the benzene ring, the movement of electrons when used as an electron transporting material becomes smoother.
When m ₁ is 0, the cyano group substituted on the benzene ring is included in R _1, and therefore m ₁ + n ₁ is an integer of 1 or more and 22 or less. m ₁ + n ₁ is preferably an integer of 2 to 8, more preferably an integer of 3 to 6.

  Further, the compound represented by the general formula (1) does not have a benzene ring substituted with 3 or more cyano groups. This is because if three or more cyano groups are substituted on one benzene ring, the chemical stability of the compound is remarkably lowered, and this is one of the causes of deterioration in performance when the device is stored at high temperature. That is, in the compound represented by the general formula (1), the number of cyano groups substituted on one benzene ring is 2 or less, and 0 or 1 is preferable from the viewpoint of chemical stability.

In the present invention, the sum of the number of benzene rings in the compound represented by the general formula (1) and the number of cyano groups substituted on the benzene ring is 9 or more and 20 or less. The compound represented by the general formula (1) has a cyano group and R ₁ so that the sum of the number of benzene rings and the number of cyano groups substituted on the benzene ring falls within the above range. The sum of the number of benzene rings and the number of cyano groups substituted on the benzene ring is preferably 9 or more and 17 or less, and more preferably 9 or more and 14 or less. By introducing a benzene ring or a cyano group into the compound, the heat resistance of the device when the compound is used in the device is improved. However, if the number of benzene rings or cyano groups is too large, sublimation property, vapor deposition film forming property, There is a tendency that the suitability for coating film formation decreases. By making the sum of the number of benzene rings and the number of cyano groups substituted on the benzene ring within the above range, both heat resistance and suitability for sublimation / film formation can be achieved.

The benzene ring in the compound represented by the general formula (1) is linked at the meta position (m-) from the viewpoint of the lowest excited triplet (T ₁ ) energy and chemical stability. It is particularly preferable that all benzene rings are linked at the meta position (m-).
The number of benzene rings in the compound represented by the general formula (1) is preferably 5 or more and 19 or less, more preferably 6 or more and 13 or less, and still more preferably 6 or more and 10 or less.
The number of cyano groups substituted on the benzene ring in the compound represented by the general formula (1) (that is, the sum of m ₁ and the number of cyano groups contained in R ₁ ) is 1 or more and 12 or less. Preferably, it is 1 or more and 7 or less, more preferably 1 or more and 5 or less.

  The compound represented by the general formula (1) is preferably a compound represented by the following general formula (2) from the viewpoint of charge transportability and chemical stability.

In general formula (2), R ₂ represents an alkyl group or an aryl group. However, the aryl group represented by R ₂ does not have a condensed ring and may have an alkyl group or a cyano group. When R ₂ there are a plurality, the plurality of R ₂ may be the same or different.
m ₂ is the number of cyano groups substituted on the biphenyl-m-kinkphenyl structure in the general formula (2), and represents an integer of 0 to 14.
n ₂ is the general formula (2) is the number of _{R 2} substituted biphenyl -m- kink phenyl structure in an integer of 0 or more and 30 or less. _Here, m ₂ + _n 2 is 1 to 30 integer.
However, the compound represented by the general formula (2) does not have a benzene ring substituted with three or more cyano groups, has at least one cyano group substituted on the benzene ring, and It has a cyano group and R ₂ so that the sum of the number of benzene rings and the number of cyano groups substituted on the benzene ring is 9 or more and 20 or less.

The alkyl group and aryl group represented by R ₂ have the same meanings as the alkyl group and aryl group represented by R ₁ described above, and their preferred ranges are also the same.

m ₂ is the number of cyano groups substituted on the biphenyl-m-kinkphenyl structure in the general formula (2), that is, the seven benzene rings linked at the meta position shown as the structural formula in the general formula (2). Yes, and represents an integer from 0 to 14. The substitution mentioned here refers to a state in which any one hydrogen atom on the seven benzene rings is replaced with a cyano group, and the benzene ring in the aryl group represented by R ₂ described above is substituted. The good cyano group is not included in the number of m ₂ . Further, for the same reason as described above, any one of the seven benzene rings is not substituted with three or more cyano groups.
In the present invention, from the viewpoint of charge transportability and chemical stability, at least one cyano group substituted on the biphenyl-m-kinkphenyl structure in the general formula (2) is present (that is, m ₂ is 1). It is preferably an integer of 14 or less, and more preferably m ₂ is an integer of 1 to 7, more preferably an integer of 1 to 5.

n ₂ is the number of R ₂ substituted in the biphenyl-m-kinkphenyl structure in the general formula (2), that is, the seven benzene rings linked at the meta position shown as the structural formula in the general formula (2). Yes, and represents an integer of 0 to 30. n ₂ is preferably an integer of 0 to 7, more preferably an integer of 0 to 4, from the viewpoints of charge transport properties and chemical stability.

The compound represented by the general formula (2) has at least one cyano group substituted on the benzene ring for the same reason as described above. The cyano group referred to here is not particularly limited as long as it is substituted on the benzene ring, and may be one of the cyano groups counted by m ₂ or the benzene ring in the aryl group represented by R _2. A cyano group substituted with may be used.
When m ₂ is 0, the cyano group substituted on the benzene ring is included in R _2, and therefore m ₂ + n ₂ is an integer of 1 or more and 30 or less. m ₂ + n ₂ is preferably an integer of 1 to 8, more preferably an integer of 1 to 5, and even more preferably an integer of 1 to 3.

  Further, the compound represented by the general formula (2) does not have a benzene ring substituted with three or more cyano groups for the same reason as described above. That is, in the compound represented by the general formula (2), the number of cyano groups substituted on one benzene ring is 2 or less, and 0 or 1 is preferable from the viewpoint of chemical stability.

In the present invention, the sum of the number of benzene rings in the compound represented by the general formula (2) and the number of cyano groups substituted on the benzene ring is 9 or more and 20 or less for the same reason as described above. The compound represented by the general formula (2) has a cyano group and R ₂ so that the sum of the number of benzene rings and the number of cyano groups substituted on the benzene ring falls within the above-mentioned range. A preferable range of the sum of the number of benzene rings and the number of cyano groups substituted on the benzene ring is the same as the range in the general formula (1).

In the compound represented by the general formula (2), the benzene ring is connected at the meta position (m-) from the viewpoint of the lowest excited triplet (T ₁ ) energy and chemical stability. It is particularly preferable that all benzene rings are linked at the meta position (m-).
The number of benzene rings in the compound represented by the general formula (2) is preferably 7 or more and 19 or less, more preferably 7 or more and 13 or less, and still more preferably 7 or more and 10 or less.
The number of cyano groups substituted on the benzene ring in the compound represented by the general formula (2) (that is, the sum of m ₂ and the number of cyano groups contained in R ₂ ) is 1 or more and 12 or less. Preferably, it is 1 or more and 7 or less, more preferably 1 or more and 5 or less.

  The compound represented by the general formula (1) is also preferably a compound represented by the following general formula (3) from the viewpoint of charge transportability and chemical stability.

In general formula (3), R ₃ represents an alkyl group or an aryl group. However, the aryl group represented by R ₃ does not have a condensed ring and may have an alkyl group or a cyano group. When R ₃ there are a plurality, the plurality of R ₃ may be the same or different.
m ₃ is the number of cyano groups substituted on the diphenyl-m-kinkphenyl structure in the general formula (3), and represents an integer of 0 or more and 14 or less.
n ₃ is the general formula (3) is the number of _{R 3} substituted diphenyl -m- kink phenyl structure in an integer of 0 or more and 30 or less. Here, m ₃ + n ₃ is an integer of 1 or more and 30 or less.
However, the compound represented by the general formula (3) does not have a benzene ring substituted with 3 or more cyano groups, has at least one cyano group substituted on the benzene ring, and It has a cyano group and R ₃ so that the sum of the number of benzene rings and the number of cyano groups substituted on the benzene ring is 9 or more and 20 or less.

The alkyl group and aryl group represented by R ₃ have the same meanings as the alkyl group and aryl group represented by R ₁ described above, and their preferred ranges are also the same.

m ₃ is the number of cyano groups substituted on the diphenyl-m-kinkphenyl structure in the general formula (3), that is, the seven benzene rings linked at the meta position shown as the structural formula in the general formula (3). Yes, and represents an integer from 0 to 14. The substitution mentioned here refers to a state in which any one hydrogen atom on the seven benzene rings is replaced with a cyano group, and the benzene ring in the aryl group represented by R ₃ described above is substituted. The good cyano group is not included in the number of m ₃ . Further, for the same reason as described above, any one of the seven benzene rings is not substituted with three or more cyano groups.
In the present invention, it is preferable that at least one cyano group substituted on the diphenyl-m-kinkphenyl structure in the general formula (3) is present (that is, m ₃ is an integer of 1 to 14), more preferably m ₃ is 1 or more and 7 or less an integer, more preferably 1 to 5 integer.

n ₃ is the number of R ₃ substituted in the diphenyl-m-kinkphenyl structure in the general formula (3), that is, seven benzene rings linked at the meta position shown as the structural formula in the general formula (3). Yes, and represents an integer from 0 to 30. n ₃ is preferably an integer of 0 or more and 7 or less, more preferably an integer of 0 or more and 4 or less, from the viewpoint of charge transportability and chemical stability.

The compound represented by the general formula (3) has at least one cyano group substituted on the benzene ring for the same reason as described above. The cyano group referred to here is not particularly limited as long as it is substituted on the benzene ring, and may be one of the cyano groups counted by m ₃ or the benzene ring in the aryl group represented by R _3. A cyano group substituted with may be used.
When m ₃ is 0, a cyano group substituted on the benzene ring is included in R _3, and therefore m ₃ + n ₃ is an integer of 1 or more and 30 or less. m ₃ + n ₃ is preferably an integer of 1 or more and 8 or less, more preferably an integer of 1 or more and 5 or less, and further preferably an integer of 1 or more and 3 or less.

  Further, the compound represented by the general formula (3) does not have a benzene ring substituted with 3 or more cyano groups for the same reason as described above. That is, in the compound represented by the general formula (3), the number of cyano groups substituted on one benzene ring is 2 or less, and 0 or 1 is preferable from the viewpoint of chemical stability.

In the present invention, the sum of the number of benzene rings in the compound represented by the general formula (3) and the number of cyano groups substituted on the benzene ring is 9 or more and 20 or less for the same reason as described above. The compound represented by the general formula (3) has a cyano group and R ₃ so that the sum of the number of benzene rings and the number of cyano groups substituted on the benzene ring falls within the above-mentioned range. A preferable range of the sum of the number of benzene rings and the number of cyano groups substituted on the benzene ring is the same as the range in the general formula (1).

The benzene ring in the compound represented by the general formula (3) is linked at the meta position (m-) from the viewpoint of the lowest excited triplet (T ₁ ) energy and chemical stability. It is particularly preferable that all benzene rings are linked at the meta position (m-).
The number of benzene rings in the compound represented by the general formula (3) is preferably 7 or more and 19 or less, more preferably 7 or more and 13 or less, and still more preferably 7 or more and 10 or less.
The number of cyano groups substituted on the benzene ring in the compound represented by the general formula (3) (that is, the sum of m ₃ and the number of cyano groups contained in R ₃ ) is 1 or more and 12 or less. Preferably, it is 1 or more and 7 or less, more preferably 1 or more and 5 or less.

  The compound represented by any one of the general formulas (1) to (3) is a compound composed of only a carbon atom, a hydrogen atom, and a nitrogen atom. Thereby, the durability is improved even after the element is stored at a high temperature.

  The molecular weight of the compound represented by any one of the general formulas (1) to (3) is usually 400 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 More preferably, it is 1000 or less. 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.

When the compound represented by any one of the general formulas (1) to (3) is used as a host material for a light emitting layer of an organic electroluminescent device or a charge transport material for a layer adjacent to the light emitting layer, it is in a thinner state than the light emitting material. When the energy gap (the light emitting material is a phosphorescent light emitting material) is large, the minimum excited triplet (T ₁ ) energy in a thin film state is large, which prevents the light emission from being quenched and 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 compound represented by any one of the general formulas (1) to (3) is preferably 2.39 eV (55 kcal / mol) or more and 3.51 eV (80 kcal / mol) or less. 2.52 eV (58 kcal / mol) to 3.25 eV (75 kcal / mol), more preferably 2.65 eV (61 kcal / mol) to 3.04 eV (70 kcal / mol). . 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 film 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) at 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 any one of the general formulas (1) to (3) is from the viewpoint of stably operating the organic electroluminescent device against heat generated during high temperature driving or during device driving. It is preferably 100 ° C. or higher and 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 any one of the general formulas (1) to (3) is low, impurities work as a charge transport trap or promote deterioration of the device. The higher the purity of the compound represented by any of 3), the better. The purity can be measured by, for example, high performance liquid chromatography (HPLC), and the area ratio of the compound represented by any one of the general formulas (1) to (3) when detected with a light absorption intensity of 254 nm is preferably 95. It is 0% or more, more preferably 97.0% or more, particularly preferably 99.0% or more, and most preferably 99.9% or more.

  As known from the carbazole-based material described in International Publication No. 2008/117889, some or all of the hydrogen atoms of the compound represented by any one of the general formulas (1) to (3) are deuterium atoms. The material substituted with can also be preferably used as a charge transport material.

  Specific examples of the compound represented by any one of the general formulas (1) to (3) are listed below, but the present invention is not limited thereto.

  The compounds exemplified as the compounds represented by any one of the above general formulas (1) to (3) can be synthesized, for example, by the method described in JP-A-2007-266598.

In the present invention, the compound represented by any one of the general formulas (1) to (3) is not limited in its use, and may be contained in any layer in the organic layer. As the introduction layer of the compound represented by any one of the general formulas (1) to (3), any one of a light emitting layer, a layer between the light emitting layer and the cathode, a layer between the light emitting layer and the anode, or It is preferably contained in a plurality of layers, and is contained in one or more of the light emitting layer, the hole injection layer, the hole transport layer, the electron transport layer, the electron injection layer, the exciton block layer, and the charge block layer. More preferably, it is more preferably contained in any one of the light emitting layer, the electron transport layer, and the electron injection layer.
In the present invention, in order to further suppress a change in chromaticity after high temperature driving, the compound represented by any one of the general formulas (1) to (3) is adjacent to the light emitting layer between the light emitting layer and the light emitting layer and the cathode. The organic layer (the cathode side layer adjacent to the light emitting layer) and the electron injection layer adjacent to the cathode on the light emitting layer side are preferably contained in the light emitting layer and the cathode side layer adjacent to the light emitting layer. More preferably, it is contained in any one of the above, and it is more preferred that it is contained in the light emitting layer. Further, the compound represented by any one of the general formulas (1) to (3) may be contained in both the light emitting layer and the cathode side layer adjacent to the light emitting layer.
When the compound represented by any one of the general formulas (1) to (3) is contained in the light emitting layer, the compound represented by any one of the general formulas (1) to (3) of the present invention is the light emitting layer. It is preferable to contain 0.1-99 mass% with respect to the total mass, It is more preferable to include 1-97 mass%, It is still more preferable to include 10-96 mass%. When the compound represented by any one of the general formulas (1) to (3) is further contained in a layer other than the light emitting layer, it is 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. It is more preferable that 85-100 mass% is contained.

[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) or (3).

[Use of compound represented by general formula (1) and charge transport material of the present invention]
The compound represented by the general formula (1) and the charge transport material of the present invention are preferably used for organic electronic elements such as electrophotography, organic transistors, organic photoelectric conversion elements (energy conversion applications, sensor applications, etc.), and organic electroluminescence elements. It can be used and is particularly preferably used for an organic electroluminescent device.

[Composition containing the charge transport material of the present invention]
The present invention also relates to a composition comprising the charge transport material. In the composition of the present invention, the content of the compound represented by any one of the general formulas (1) to (3) is preferably 30 to 99% by mass with respect to the total solid content in the composition, More preferably, it is 50-97 mass%, and it is still more preferable that it is 70-96 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. Preferably, a host material, a phosphorescent material, or a hydrocarbon material is used.
The composition of the present invention can form an organic layer of an organic electroluminescent element by a dry film forming method such as a vapor deposition method or a sputtering method, or a wet film forming method such as a transfer method or a printing method.

[Thin Film Containing Charge Transport Material of the Present Invention]
The present invention also relates to a thin film containing a charge transport material represented by any one of the general formulas (1) to (3). 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 device of the present invention is an organic electroluminescent device having a pair of electrodes comprising an anode and a cathode and at least one organic layer including a light emitting layer between the electrodes on the substrate, wherein the light emitting layer And at least one of the at least one organic layer contains a compound represented by any one of the general formulas (1) to (3) of the present invention. 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 on the transparent electrode or the translucent 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 phosphorescent material.

(Luminescent material)
In the present invention, in addition to at least one phosphorescent light-emitting material contained in the light-emitting layer, a fluorescent light-emitting material or a phosphorescent light-emitting material different from the phosphorescent light-emitting material contained in the light-emitting layer can be used as the light-emitting material.
Details of these fluorescent light-emitting materials and phosphorescent light-emitting 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 2001-247859, JP 2002-302671, JP 2002-117978, JP 2003-133074, JP 2002-235076, JP 2003-123982, JP 2002-170684, EP 121157, JP -226495, JP 2002-234894, JP 2001-247859, JP 2001-298470, JP 2002-17367. , JP 2002-203678, JP 2002-203679, JP 2004-357799, JP 2006-256999, JP 2007-19462, JP 2007-84635, JP 2007-96259, and the like. Examples of such a light emitting 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 together with the compound represented by any one of the general formulas (1) to (3) in the light emitting layer.

  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.

  General formula (E-1) is demonstrated.

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, and is 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. Examples of the 5- or 6-membered heterocycle containing A ₁ , Z ¹ and a nitrogen atom include 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 A ₁ , Z ¹ and a nitrogen atom may have a substituent. 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. The substituent on carbon is preferably an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, or a fluorine atom.

  The substituent is appropriately selected for controlling the emission wavelength and potential, but in the case of 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 complex stability, emission wavelength control, and emission quantum yield, a 5- or 6-membered ring formed of B ₁ , Z ² and a carbon atom is preferably a benzene ring, a pyridine ring, a pyrazine ring, an imidazole ring, or a pyrazole. 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 by 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. The substituent on carbon is preferably an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, or a fluorine atom.

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

The substituent on 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.

(XY) represents a bidentate monoanionic ligand. Examples of bidentate monoanionic ligands are described on pages 89-90 of Lamansky et al., WO 02/15645.
The bidentate monoanionic ligand represented by (XY) is preferably a bidentate monoanionic ligand represented by the following general formula (L-1).

In General Formula (L-1), R ^L1 and R ^L2 each independently represent an alkyl group, an aryl group, or a heteroaryl group.
R ^L3 represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group.

The alkyl group represented by R ^{L1 to} R ^L3 may have a substituent, and may be saturated or unsaturated. Examples of the substituent in the case of having a substituent include the above-described substituent Z ′, and preferred substituent Z ′ includes a phenyl group, an aromatic heterocyclic group, a fluorine atom, a silyl group, an amino group, a cyano group, or these. And a phenyl group, a fluorine atom, and a cyano group are more preferable. The alkyl group represented by R ^{L1 to} R ^L3 is preferably an alkyl group having 1 to 8 carbon atoms, and more preferably an alkyl group having 1 to 5 carbon atoms.

The aryl group represented by R ^{L1 to} R ^L3 may be condensed or may have a substituent. In the case of having a substituent, examples of the substituent include the above-described substituent Z ′, and the substituent Z ′ is preferably an alkyl group or an aryl group, and more preferably an alkyl group. The aryl group represented by R ^{L1 to} R ^L3 is preferably an aryl group having 6 to 30 carbon atoms, and more preferably an aryl group having 6 to 18 carbon atoms.

The heteroaryl group represented by R ^{L1 to} R ^L3 may be condensed or may have a substituent. In the case of having a substituent, examples of the substituent include the above-described substituent Z ′, and the substituent Z ′ is preferably an alkyl group or an aryl group, and more preferably an alkyl group. The heteroaryl group represented by R ^{L1 to} R ^L3 is preferably a C 4-12 heteroaryl group, and more preferably a C 4-10 heteroaryl group.

R ^L1 and R ^L2 are preferably an alkyl group or an aryl group, more preferably an alkyl group or a phenyl group, and particularly preferably an alkyl group.
The alkyl group represented by R ^L1 and R ^L2 is preferably an alkyl group having 1 to 8 carbon atoms in total, more preferably an alkyl group having 1 to 5 carbon atoms in total, such as a methyl group or an ethyl group. N-propyl group, iso-propyl group, iso-butyl group, t-butyl group, n-butyl group, cyclohexyl group and the like, and methyl group, ethyl group, iso-butyl group, or t-butyl group A methyl group is preferable, and a methyl group is particularly preferable.

R ^L3 is preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom.

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

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 represent 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 condensed rings 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.
A ^E1 is preferably a to A ^E4 is ^{C-R E,} if A E1 ^{to 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 in 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, an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic group 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. In the case where 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 preferable 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 are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, -CN, perfluoroalkyl group, trifluorovinyl _{group, -CO 2 R, -C (O} ) R, -NR 2, -NO 2, -OR, halogen atom, an aryl group or a heteroaryl group, 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.
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.
(X—Y) 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, and 3-pentenyl.
The alkynyl group represented by R ^{T1 to} R ^T7 and R ′ is preferably 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 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 one 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 ′.
In addition, A represents CR ′, and among R ^{T1 to} R ^T7 and R ′, 0 to 2 are particularly preferably an alkyl group or a phenyl group and the rest are all hydrogen atoms, and R ^{T1 to} R ^T7 , And R ′ are particularly preferably 0 to 2 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, and 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) is synonymous with (XY) in general formula (E-1), and its preferable range is also the same.

  One of the preferable forms 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, (X—Y) and n _E4 in General Formula (E-4) are R ^{T1 to} R ^T4 , A, (XY) and n _{E3 in} General Formula (E-3). The preferred range is also the same. R ₁ ′ to R ₅ ′ 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 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 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.
Moreover, the preferable range in R < ₁ >'-R< ₅ >' is the same as R ^{< T1} > -R <^T7> , R 'in general formula (E-3). Further, it is particularly preferable that A represents CR ′, and among R ^{T1 to} R ^T4 , R ′, and R ₁ ′ to R ₅ ′, 0 to 2 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 preferable form 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, (X—Y) and n _E5 in General Formula (E-5) are R ^{T2 to} R ^T6 , A, (XY) and n _{E3 in} 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, —CN, 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 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 ^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 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.
Moreover, the preferable range in R < ₆ >'-R< ₈ >' is the same as R ^{< T1} > -R <^T7> , R 'in general formula (E-3). Further, it is particularly preferable that 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.

  Another preferable 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, 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 may be represented, 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.
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. Of these, the case where R _1j and R _1k are linked to form a single bond is particularly preferred.
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.
(X—Y) 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). Also, it is particularly preferable 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. More preferably, it is an atom.
The preferable range of (XY) and _nE6 is the same as that of (XY) and _nE3 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 the formula _(E-7), definition and preferable ranges of R 1a _{to R 1i} are the same as _R 1a _{to R 1i} in the formula (E-6). In addition, it is particularly preferable that 0 to 2 of R _{1a to} R _1i are an alkyl group or an aryl group, and the rest are all hydrogen atoms. The definitions and preferred ranges of (X—Y) and n _E7 are the same as (X—Y) and n _E3 in general formula (E-3).

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

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

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

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

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

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

  Next, general formula (C-1) will be described.

(In General Formula (C-1), 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 Represents a single bond or a divalent linking group.)

General formula (C-1) is demonstrated.
Q ¹ , Q ² , Q ³ and Q ⁴ each independently represent a ligand coordinated to Pt. At this time, the bond between Q ¹ , Q ² , Q ³ and Q ⁴ and Pt may be any of a covalent bond, an ionic bond, a coordinate bond, and the like. As an atom couple | bonded with Pt in Q < ¹ >, Q < ² >, Q < ³ > and Q < ⁴ >, a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a phosphorus atom are preferable, 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, and particularly preferably two are carbon atoms and two are nitrogen atoms.

Q ¹ , Q ² , Q ³ and Q ⁴ bonded to Pt by a carbon atom may be an anionic ligand or a neutral ligand, and the anionic ligand is a vinyl ligand, Aromatic hydrocarbon ring ligand (eg benzene ligand, naphthalene ligand, anthracene ligand, phenanthrene ligand), heterocyclic ligand (eg furan ligand, thiophene ligand, pyridine) Ligand, pyrazine ligand, pyrimidine ligand, pyridazine ligand, triazine ligand, thiazole ligand, oxazole ligand, pyrrole ligand, imidazole ligand, pyrazole ligand, triazole And a condensed ring containing them (for example, quinoline ligand, benzothiazole ligand, etc.). A carbene ligand is mentioned as a neutral ligand.

Q ¹ , Q ² , Q ³ and Q ⁴ bonded to Pt with a nitrogen atom may be neutral ligands or anionic ligands, and as neutral ligands, nitrogen-containing aromatic hetero Ring ligand (pyridine ligand, pyrazine ligand, pyrimidine ligand, pyridazine ligand, triazine ligand, imidazole ligand, pyrazole ligand, triazole ligand, oxazole ligand, Examples include thiazole ligands and condensed rings containing them (for example, quinoline ligands, benzimidazole ligands), amine ligands, nitrile ligands, and imine ligands. Examples of anionic ligands include amino ligands, imino ligands, nitrogen-containing aromatic heterocyclic ligands (pyrrole ligands, imidazole ligands, triazole ligands and condensed rings containing them) (For example, indole ligand, benzimidazole ligand, etc.)).

Q ¹ , Q ² , Q ³ and Q ⁴ bonded to Pt with an oxygen atom may be neutral ligands or anionic ligands, and neutral ligands are ether ligands, Examples include ketone ligands, ester ligands, amide ligands, oxygen-containing heterocyclic ligands (furan ligands, oxazole ligands and condensed rings containing them (benzoxazole ligands, etc.)). It is done. Examples of the anionic ligand include an alkoxy ligand, an aryloxy ligand, a heteroaryloxy ligand, an acyloxy ligand, a silyloxy ligand, and the like.

Q ¹ , Q ² , Q ³ and Q ⁴ bonded to Pt with a sulfur atom may be neutral ligands or anionic ligands, and neutral ligands include thioether ligands, Examples include thioketone ligands, thioester ligands, thioamide ligands, sulfur-containing heterocyclic ligands (thiophene ligands, thiazole ligands and condensed rings containing them (such as benzothiazole ligands)). It is done. Examples of the anionic ligand include an alkyl mercapto ligand, an aryl mercapto ligand, and a heteroaryl mercapto ligand.

Q ¹ , Q ² , Q ³ and Q ⁴ bonded to Pt with a phosphorus atom may be neutral ligands or anionic ligands, and neutral ligands include phosphine ligands, Examples include phosphate ester ligands, phosphite ester ligands, and phosphorus-containing heterocyclic ligands (phosphinin ligands, etc.). Anionic ligands include phosphino ligands and phosphinyl ligands. And phosphoryl ligands.

The groups represented by Q ¹ , Q ² , Q ^3, and Q ⁴ may have a substituent, and those listed as the substituent group A can be appropriately applied as the substituent. Moreover, substituents may be connected to each other (when Q ³ and Q ⁴ are connected, a Pt complex of a cyclic tetradentate ligand is formed).

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

L ¹ , L ² and L ³ represent a single bond or a divalent linking group. Examples of the divalent linking group represented by L ¹ , L ² and L ³ include alkylene groups (methylene, ethylene, propylene, etc.), arylene groups (phenylene, naphthalenediyl), heteroarylene groups (pyridinediyl, thiophenediyl, etc.) ), Imino group (—NR _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, examples of R _L and R _L ′ include an alkyl group and an aryl group. These linking groups may further have a substituent. As the substituent, those exemplified as the substituent group A can be appropriately applied.
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, particularly preferably a single bond, a dimethylmethylene group, a diphenylmethylene group, and a cyclohexanediyl group.

  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 General Formula (C-2), L ²¹ represents a single bond or a divalent linking group. A ²¹ and A ²² each independently represent a carbon atom or a nitrogen atom. Z ²¹ and Z ²² each independently represent a nitrogen-containing aromatic heterocycle. Z ²³ and Z ²⁴ each independently represent a benzene ring or an aromatic heterocycle.

General formula (C-2) is demonstrated.
L ²¹ has the same meaning as L ^{1 in} 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, the substituent group A as a substituent on a carbon atom, and the substituent on a nitrogen atom as The substituent group B can be applied. The substituent on carbon is preferably an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, or a halogen atom. The substituent is appropriately selected for controlling the emission wavelength and potential, but in the case of shortening the wavelength, an electron donating group, a fluorine atom, and an aromatic ring group are preferable. For example, an alkyl group, a dialkylamino group, an alkoxy group, A fluorine atom, an aryl group, an aromatic heterocyclic group and the like are selected. In the case of increasing the wavelength, an electron withdrawing group is preferable, and for example, a cyano group, a perfluoroalkyl group, or the like is selected. The substituent on the nitrogen atom is preferably an alkyl group, an aryl group, or an aromatic heterocyclic group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex. The substituents may be linked to form a condensed ring, and the formed ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazole. Ring, thiophene ring, furan ring and the like.

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

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

  Of the platinum complexes represented by the general formula (C-2), one of the more preferable embodiments is a platinum complex represented by the following general formula (C-3).

In General Formula (C-3), A ^{301 to} A ³¹³ each independently represent C—R or a nitrogen atom. R represents a hydrogen atom or a substituent. L ³¹ represents a single bond or a divalent linking group.

General formula (C-3) is demonstrated.
L ³¹ has the same meaning as L ²¹ in formula (C-2), and the preferred range is also the same.
A ^{301 to} A ³⁰⁶ each independently represent C—R or a nitrogen atom. R represents a hydrogen atom or a substituent. As the substituent represented by R, those exemplified as the substituent group A can be applied. A ^{301 to} A ³⁰⁶ are preferably C—R, and Rs may be connected to each other to form a ring. When A ^{301 to} A ³⁰⁶ are C—R, R in A ³⁰² and A ³⁰⁵ 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, particularly preferably a hydrogen atom or a fluorine atom, and R as A ³⁰¹ , A ³⁰³ , A ³⁰⁴ , or A ³⁰⁶ is preferably a hydrogen atom. , Alkyl group, aryl group, amino group, alkoxy group, aryloxy group, fluorine atom, cyano group, more preferably hydrogen atom, amino group, alkoxy group, aryloxy group, fluorine atom, particularly preferably hydrogen atom. It is.
A ³⁰⁷ , A ³⁰⁸ , A ³⁰⁹ and A ³¹⁰ 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 ³⁰⁷ , A ³⁰⁸ , A ³⁰⁹ and A ³¹⁰ are C—R, R is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, a diarylamino Group, alkyloxy group, cyano group, halogen atom, more preferably hydrogen atom, alkyl group, perfluoroalkyl group, aryl group, dialkylamino group, cyano group, fluorine atom, more preferably hydrogen atom, alkyl group. , A trifluoromethyl group and a fluorine atom. If possible, the substituents may be linked to form a condensed ring structure. When shifting the emission wavelength to the short wavelength side, A ³⁰⁸ is preferably a nitrogen atom.

When A ^{307 to} A ³¹⁰ are selected as described above, the 6-membered ring formed from two carbon atoms and A ³⁰⁷ , A ³⁰⁸ , A ³⁰⁹ and A ³¹⁰ includes a pyridine ring, a pyrazine ring, a pyrimidine ring, and a pyridazine ring. And a triazine ring, more preferably a pyridine ring, a pyrazine ring, a pyrimidine ring and a pyridazine ring, and particularly preferably a pyridine ring. When the 6-membered ring is a pyridine ring, a pyrazine ring, a pyrimidine ring, or a pyridazine ring (particularly preferably a pyridine ring), a hydrogen atom present at a position where a metal-carbon bond is formed as compared with a benzene ring. Since the acidity is improved, a metal complex is more easily formed, which is advantageous.

A ³¹¹ , A ³¹² and A ³¹³ 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 ³¹¹ , A ³¹² and A ³¹³ are C—R, R is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, a diarylamino group, an alkyl An oxy group, a cyano group, and a halogen atom, more preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, a dialkylamino group, a cyano group, and a fluorine atom, and more preferably a hydrogen atom, an alkyl group, and trifluoro A methyl group and a fluorine atom. If possible, the substituents may be linked to form a condensed ring structure.
^{Examples of} the 5-membered ring formed by A ³¹¹ , A ³¹² and A ³¹³ and one nitrogen atom and one carbon atom include a pyrrole ring, a pyrazole ring, an imidazole ring, a furan ring, and a thiophene ring, and more preferable. Is a pyrrole ring, a pyrazole ring or an imidazole ring, more preferably a pyrrole ring or a pyrazole ring. Since the 5-membered ring is a pyrrole ring, a pyrazole ring, or an imidazole ring (more preferably, a pyrrole ring or a pyrazole ring), it is advantageous because the stability of the metal complex is improved.

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

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

General formula (C-4) is demonstrated.
A ^{401 to} A ⁴¹⁴ each independently represent C—R or a nitrogen atom. R represents a hydrogen atom or a substituent. A ^{401 to} A ⁴⁰⁶ and L ⁴¹ have the same meanings as A ^{301 to} A ³⁰⁶ and L ³¹ in the general formula (C-3), and preferred ranges thereof are also the same.

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

  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-5).

In General Formula (C-5), L ⁵¹ represents a single bond or a divalent linking group. A ⁵¹ each independently represents a carbon atom or a nitrogen atom. Z ⁵¹ and Z ⁵² each independently represent a nitrogen-containing aromatic heterocycle. Z ⁵³ each independently represents a benzene ring or an aromatic heterocycle. Y is an anionic acyclic ligand that binds to Pt.

General formula (C-5) is demonstrated.
L ⁵¹ has the same meaning as ^{L 1} in the general formula (C-1), and the preferred ranges are also the same.

A ⁵¹ 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 ⁵¹ is preferably a carbon atom.

Z ⁵¹ and Z ⁵² are respectively synonymous with Z ²¹ and Z ²² in the general formula (C-2), and preferred ranges thereof are also the same. Z ⁵³ has the same meaning as Z ²³ in formula (C-2), and the preferred range is also the same.

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

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

  Of the platinum complexes represented by the general formula (C-5), one of more preferred embodiments is a platinum complex represented by the following general formula (C-6).

In General Formula (C-6), A ^{601 to} A ⁶¹⁰ each independently represent C—R or a nitrogen atom. R represents a hydrogen atom or a substituent. L ⁶¹ represents a single bond or a divalent linking group. Y is an anionic acyclic ligand that binds to Pt.

General formula (C-6) is demonstrated.
L ⁶¹ has the same meaning as L ^{51 in} formula (C-5), and the preferred range is also the same. A ⁶⁰¹ to A ⁶¹⁰ is formula (C-3) have the same meanings as ^A 301 ^{to A 310} in the preferred ranges are also the same. Y has the same meaning as that in formula (C-5), and the preferred range is also the same.

  Specific examples of the platinum complex represented by the general formula (C-1) include paragraph numbers [0143] to [0152], [0157] to [0158] and [0162] to [0162] to [0162] of JP-A-2005-310733. 0168], compounds described in paragraphs [0065] to [0083] of JP 2006-256999 A, compounds described in paragraphs [0065] to [0090] of JP 2006-93542 A , Compounds described in paragraphs [0063] to [0071] of JP-A-2007-73891, compounds described in paragraphs [0079] to [0083] of JP-A-2007-324309, and JP-A-2006-93542 Compounds described in paragraph numbers [0065] to [0090] of Japanese Patent Publication No. 2007-96255, paragraph numbers [0055] to [00] of Japanese Patent Laid-Open No. 2007-96255 The compound according to 1] include [0043] to [0046] of JP 2006-313796. More specifically, although the platinum complex illustrated below is mentioned, this invention is not limited to these.

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

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

(Host material)
The host material is a compound mainly responsible for charge injection and transport in the light-emitting layer, and is a compound that itself 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 any one of the general formulas (1) to (3) of the present invention 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, thiophene, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, arylamine, amino-substituted chalcone, styrylanthracene, fluorenone, hydrazone , Stilbene, silazane, aromatic tertiary amine compounds, styrylamine compounds, porphyrin compounds, polysilane compounds, poly (N-vinylcarbazole), aniline copolymers, thiophene oligomers, polythiophene and other conductive polymer oligomers , Organic silane, carbon film, pyridine, pyrimidine, triazine, imidazole, pyrazole, triazole, oxazole, oxadiazol, full Lenone, anthraquinodimethane, anthrone, diphenylquinone, thiopyran dioxide, carbodiimide, fluorenylidenemethane, distyrylpyrazine, fluorine-substituted aromatic compounds, heterocyclic tetracarboxylic anhydrides such as naphthaleneperylene, phthalocyanine, 8- Various metal complexes represented by metal complexes of quinolinol derivatives, metal phthalocyanines, benzoxazoles and benzothiazoles as ligands, and derivatives thereof (may have substituents or condensed rings) And the like.

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, but a hole transporting host material can be used.
In the present invention, the light emitting layer preferably contains a host material. The host material is preferably a compound represented by the following general formula (4-1) or (4-2).
In the present invention, it is more preferable that the light emitting layer contains at least one compound represented by the general formula (4-1) or (4-2).

  In the present invention, when the compound represented by formula (4-1) or (4-2) is contained in the light emitting layer, the compound represented by formula (4-1) or (4-2) is It is preferable that 30-100 mass% is contained in a light emitting layer, it is preferable that 40-100 mass% is contained, and it is especially preferable that 50-100 mass% is contained. Moreover, when using the compound represented by general formula (4-1) or (4-2) for a some organic layer, it is preferable to contain in said layer in each layer.

  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 General Formulas (4-1) and (4-2), d and e each represent an integer of 0 to 3, and at least one 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 the general formula (5), .g representing the substituent R _'9 are each independently an integer of 0-8.)

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 excessively shielding 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 the 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.

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.

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.

  Furthermore, the atom which comprises a substituent represents that the isotope is also included.

  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.

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 _'9, R in the formula (5)' is synonymous with _9.

  Specific examples of the compounds represented by 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 any one of the general formulas (1) to (3), the compound represented by any one of the general formulas (1) to (3) is It is preferable that it is 50 to 99 mass% in all the host compounds.

[Compound represented by formula (M-1)]
In the organic electroluminescent element of the present invention, it is preferable that the pair of electrodes include an anode, and at least one organic layer is included between the light emitting layer and the anode, and at least one of the following general formulas ( It is preferable to contain the compound represented by M-1).

The compound represented by the general formula (M-1) is more preferably contained in the organic layer adjacent to the light emitting layer between the light emitting layer and the anode, but the use thereof is not limited, and the 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, which contains 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 preferable embodiment of the compound represented by the general formula (M-1) is a case represented by the following general formula (M-3).

In general formula (M-3), R ^{S1 to} R ^S5 are each independently 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. 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 each of a plurality of R ^{S2 to} R ^S5 is present, they may be the same or different, and any two may be bonded 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 or 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, 1-isopropenyl, 1-butenyl, 2-butenyl, 3-pentenyl and the like can be mentioned.
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 the 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.
Moreover, when using the compound represented by general formula (M-1) for a some organic layer, it is preferable to contain in said layer in each layer.

  The compound represented by the general formula (M-1) may contain only one kind in any one of the organic layers, and the compound represented by the plurality of general formulas (M-1) may be added at any ratio. 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 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 above-described materials, or may have 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 a hydrogen isotope (such as a deuterium atom). 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 preferably forms 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 formula (M-1) are shown below, but the present invention is not limited to these.

[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, and more preferably 85 to 100% by mass. When the aromatic hydrocarbon compound is contained in the light emitting layer, it is preferably included in an amount of 0.1 to 99% by mass, more preferably 1 to 95% by mass, and more preferably 10 to 95%, based on the total mass of the light emitting layer. It is more preferable to include the mass%.
It is preferable to use a hydrocarbon compound consisting of only carbon atoms and hydrogen atoms, having a molecular weight in the range of 400 to 1200, and having a condensed polycyclic skeleton having a total carbon number of 13 to 22. Examples of the condensed polycyclic skeleton carbon atoms in total 13 to 22, fluorene fluorene, anthracene, phenanthrene, tetracene, chrysene, pentacene, pyrene, perylene, is preferably one of triphenylene, in view of T _1, triphenylene, phenanthrene Are 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 the hydrocarbon compound may be further contained in any layer within the organic layer as well as the organic layer adjacent to the light emitting layer.

(In 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 which may be substituted with a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, Represents a fluorenyl group, a naphthyl group, or a triphenylenyl group, provided that R ^{12 to} R ²³ are not all hydrogen atoms.)

Examples of the alkyl group represented by R ^{12 to} R ²³ include a substituted or unsubstituted, for example, methyl group, ethyl group, isopropyl group, n-butyl group, tert-butyl group, n-octyl group, n-decyl group, n-hexadecyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group and the like can be mentioned, preferably methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, more preferably methyl group, 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, and 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.

  The total number of aryl rings in the general formula (Tp-1) 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, and 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 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.)

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

  In another aspect 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 optionally substituted with a triphenylenyl group, a fluorenyl group, a naphthyl group, 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 thereof is 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 at the meta position with an alkyl group having 1 to 4 carbon atoms, 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 generation during high temperature driving or during device driving. The temperature is preferably 100 ° C. or higher and 400 ° C. or lower, more preferably 120 ° C. or higher and 400 ° C. or lower.

  Although the specific example of the hydrocarbon compound concerning this invention is illustrated below, this invention is not limited to these.

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 includes at least one organic layer between the light emitting layer and the cathode, and contains at least one compound represented by the following general formula (O-1) in the organic layer. Is preferable from the viewpoints of element efficiency and driving voltage. Below, general formula (O-1) is demonstrated.

In (formula ^{(O1), R O1} represents an alkyl group, an aryl group, or ^.A O1 ^{to A O4} representing the heteroaryl group each independently may .R ^A representing a ^{C-R A} or a 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, 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 a carbon number of 1 to 8), an aryl group (preferably having a carbon number of 6 to 30), or a heteroaryl group (preferably having a carbon number of 4 to 12). Z ′ may be included. 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 Z ′, more preferably a phenyl group which may be substituted with an alkyl group or an aryl group, and still more preferably unsubstituted. A phenyl group or a 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. It is preferable that all of A ^{O1 to} A ^O4 are C—R ^A or A ^O1 is a nitrogen atom and A ^{O2 to} A ^O4 are C—R ^A , A ^O1 is a nitrogen atom, and A ^O2 to More preferably, A ^O4 is C—R ^A , 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 Z ′. 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 the above-described substituent Z ′, and when it has a substituent, the substituent is preferably an alkyl group, an aryl group, or a cyano group. Specific examples of L ^O1 include the following.

^nO1 represents an integer of 2 to 6, preferably an integer of 2 to 4, and 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 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 represents 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 are the same or different. May be.)

R ^O1 and ^A O1 ^{to A O4,} the general formula (O1) in a same meaning as ^{R O1} and ^A O1 ^{to 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). Which may have the aforementioned substituent Z ′. 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 stability at high temperature storage, stable operation against high temperature driving, and heat generation during driving. It is preferably ˜300 ° C., more preferably 120 ° C. to 300 ° C., still more preferably 120 ° C. to 300 ° C., and still more preferably 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 the organic layer between the light emitting layer and the cathode, but is contained in the cathode side layer adjacent to the light emitting layer. Is preferred.

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

(Hole injection layer, hole transport layer)
The hole injection layer and the hole transport layer are layers having a function of receiving holes from the anode or the anode side and transporting them to the cathode side.
Regarding the hole injection layer and the hole transport layer, the matters described in paragraph numbers [0165] to [0167] 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 reduced, and efficiency is improved. The electron-accepting dopant may be any organic material or inorganic material as long as it can extract electrons from the doped material and generate radical cations, for example, tetracyanoquinodimethane. (TCNQ), 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 0.1% by mass to 40% by mass with respect to the total compound mass forming the hole injection layer. % Content is more preferable, and 0.2% by mass to 30% by mass is more preferable.

(Electron injection layer, electron transport layer)
The electron injection layer and the electron transport layer are layers having a function of receiving electrons from the cathode or the cathode side and transporting them to the anode side. The electron injection material and the electron transport material used for these layers may be a low molecular compound or a high molecular compound.
As the electron transport material, a compound represented by any one of the general formulas (1) to (3) 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, etc., aromatic 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 still more preferably 10 nm to 100 nm. In addition, the thickness of the electron injection layer is preferably 0.1 nm to 200 nm, more preferably 0.2 nm to 100 nm, and still more preferably 0.5 nm to 50 nm.
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) , Dithiimidazole 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, based on the total mass of the compound forming the electron injection layer. It is more preferable that 0.5% by mass to 30% by mass is contained.

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

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

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

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

(Drive)
The organic electroluminescence device of the present invention emits light by applying a direct current (which may include an alternating current component as necessary) voltage (usually 2 to 15 volts) or a direct current between the anode and the cathode. Can be obtained.
The driving method of the organic electroluminescence device of the present invention is described in JP-A-2-148687, JP-A-6-301355, JP-A-5-29080, JP-A-7-134558, JP-A-8-234658, and JP-A-8-2441047. The driving methods described in each publication, Japanese Patent No. 2784615, US Pat. Nos. 5,828,429 and 6,023,308 can be applied.

The external quantum efficiency of the organic electroluminescent element of the present invention is preferably 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 and a display device.

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

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

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

(Lighting device)
Next, 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.

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

1. Synthesis Example (Synthesis Example 1) Synthesis of Compound 3

3,5-dibromobenzonitrile 10.0 g (38.3 mmol), phenylboronic acid 4.6 g (38.3 mmol), palladium acetate 0.22 g (1.0 mmol), triphenylphosphine 0.91 g (4.0 mmol) Sodium carbonate 10.6 g (100 mmol), 1,2-dimethoxyethane (DME) 200 mL, and pure water 200 mL were mixed and heated to reflux under a nitrogen atmosphere for 4 hours. After cooling the reaction solution to room temperature, the precipitated solid was filtered and washed successively with pure water, ethanol and hexane. The obtained solid was washed with ethanol and dried to obtain 6.42 g (24.9 mmol) of synthetic intermediate A (yield 65%).
Synthetic intermediate A 6.40 g (24.8 mmol), bis (pinacolato) diboron 7.57 g (29.8 mmol), [1,1′-bis (diphenylphosphino) ferrocene] palladium (II) dichloride dichloromethane complex (1: 1) 0.61 g (0.74 mmol), 7.30 g (74.4 mmol) of potassium acetate and 100 mL of dimethylacetamide (DMAc) were mixed and mixed at 70 ° C. for 4 hours under a nitrogen atmosphere. The reaction liquid cooled to room temperature was added to ice water, the precipitated solid was filtered, and washed successively with pure water, ethanol, and hexane. The obtained solid was washed with ethanol and dried to obtain 5.58 g (18.3 mmol) of synthetic intermediate B (yield 74%).
Synthetic intermediate B5.00 g (16.4 mmol), 1,3,5-tribromobenzene 1.64 gg (5.21 mmol), tris (dibenzylideneacetone) dipalladium (0) 0.36 g (0.39 mmol), 2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl (SPhos) 0.64 g (1.56 mmol), tripotassium phosphate 6.64 g (31.3 mmol), benzonitrile 50 mL, pure water 25 mL were mixed, The mixture was stirred at 120 ° C. for 6 hours under a nitrogen atmosphere. The reaction solution was allowed to cool to room temperature, ethyl acetate was added to extract the organic layer, and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure to obtain a benzonitrile solution, ethanol was added, and the deposited precipitate was collected by filtration. The obtained solid was recrystallized from toluene to obtain 2.26 g (3.70 mmol) of Compound 3 (yield 71%).
¹ H NMR (400 MHz, in DMSO-d6); δ (ppm) = 8.52-8.51 (m, 6H), 8.36 (s, 3H), 8.20 (s, 3H), 7. 91 (d, J = 7.2 Hz, 6H), 7.56-7.45 (m, 9H). MS (MALDI-TOF): m / z = 610.2 ([M + H] ^< +>).

(Synthesis Examples 2 to 11) Synthesis of Compounds 1, 2, 4 to 11 Compounds 1, 2, 4 to 11 were synthesized according to the scheme shown below. Reaction conditions and purification operations are the same as in Synthesis Example 1.

The measurement results of ¹ H NMR and / or MS (MALDI-TOF) of the synthesized compounds ¹ , 2, ⁴ to 11 are described below.
Compound 1
¹ H NMR (400 MHz, in DMSO-d6); δ (ppm) = 8.37 (s, 2H), 8.19 (s, 2H), 8.09 (s, 4H), 8.04 (s, 2H), 7.98 (s, 1H), 7.93-7.87 (m, 12H), 7.56-7.37 (m, 18H). MS (MALDI-TOF): m / z = 788.3 ([M + H] ^< +>).
Compound 2
¹ H NMR (400 MHz, in DMSO-d6); δ (ppm) = 8.15 (s, 3H), 7.93 (t, J = 7.7 Hz, 3H), 7.82 (d, J = 7.7 Hz, 3H), 7.72-7.65 (m, 9H), 7.58-7.48 (m, 9H). MS (MALDI-TOF): m / z = 610.2 ([M + H] ^< +>).

Compound 4
¹ H NMR (400 MHz, in DMSO-d6); δ (ppm) = 8.51 (s, 4H), 8.36 (s, 1H), 8.33 (d, J = 8.4 Hz, 4H), 8.19-8.18 (m, 4H), 8.15 (s, 2H), 8.00-7.98 (m, 2H), 7.89 (d, J = 8.4 Hz, 4H), 7.74-7.71 (m, 4H), 7.69-7.66 (m, 1H). MS (MALDI-TOF): m / z = 635.2 ([M + H] ^< +>).
Compound 5
MS (MALDI-TOF): m / z = 661.3 ([M + H] ^< +>).
Compound 6
MS (MALDI-TOF): m / z = 938.3 ([M + H] ^< +>).
Compound 7
MS (MALDI-TOF): m / z = 720.4 ([M + H] ^< +>).
Compound 8
MS (MALDI-TOF): m / z = 641.3 ([M + H] ^< +>).
Compound 9
MS (MALDI-TOF): m / z = 691.3 ([M + H] ^< +>).
Compound 10
MS (MALDI-TOF): m / z = 612.2 ([M + H] ^< +>).
Compound 11
¹ H NMR (400 MHz, in DMSO-d6); δ (ppm) = 8.35 (s, 3H), 8.23-8.16 (m, 9H), 7.9 (d, J = 7.6 Hz) , 3H), 7.86 (d, J = 7.6 Hz, 3H), 7.81 (d, J = 7.6 Hz, 3H), 7.72-7.64 (m, 6H). MS (MALDI-TOF): m / z = 610.2 ([M + H] ^< +>).

  Compounds 1 to 11 synthesized as described above and used in Examples are shown below together with Comparative Compounds 1 to 11 used in Examples.

2. Element fabrication and evaluation All materials used for element fabrication were purified by sublimation, 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 higher. . In addition, since the comparative compound 10 and the comparative compound 11 had undergone thermal decomposition prior to sublimation, film formation by sublimation purification or vacuum deposition was impossible. Further, the solubility in a solvent was extremely low, and it was impossible to form a coating film under the conditions of Example 9.
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 use as an electron transport material, and “EIL” means use as an electron injection material.

(Example 1) (Green ETL, EIL)
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, ultrasonically cleaned in 2-propanol, and then subjected to UV-ozone treatment for 30 minutes. Went. The following organic layers were sequentially deposited on the transparent anode (ITO film) by vacuum deposition.
First layer: GD-1: film thickness 10 nm
Second layer: NPD: film thickness 25 nm
Third layer: HT-1: film thickness 3 nm
Fourth layer: mCBP and GD-1 (mass ratio 90:10): film thickness 30 nm
Fifth layer: Comparative compound 1: film thickness 5 nm
Sixth layer: Alq: film thickness 45 nm
On top of this, 0.1 nm of lithium fluoride and 100 nm of metallic aluminum were vapor-deposited in this order to form a cathode.
This is put in a glove box substituted with nitrogen gas without being exposed to the atmosphere, and sealed with a glass sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.). Thus, a comparative element 1-1 was obtained. Similarly, by using the material shown in Table 1 instead of the comparative compound 1 as the material of the fifth layer and using the material shown in Table 1 as the material of the sixth layer, the elements 1-1 to 1- 10 and Comparative elements 1-2 to 1-9 were obtained. Table 1 shows the results of evaluating these elements by the following methods from the viewpoints of efficiency, driving voltage, efficiency change after high temperature storage, chromaticity change after high temperature storage, and durability after high temperature storage.

(A) 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) Driving voltage Each element is caused to emit light by applying a DC voltage so that the luminance becomes 1000 cd / m ² . The applied voltage at this time was used as an index for driving voltage evaluation. The driving voltage is preferably as small as possible.
(C) Change in efficiency after high-temperature storage Each element is stored in a thermostat at 100 ° C. for 24 hours, and then light is emitted by applying a DC voltage so that the luminance becomes 1000 cd / m ² at room temperature. The external quantum efficiency η ₁₀₀ at this time was compared with the external quantum efficiency η _RT when light was emitted at room temperature, and the ratio between the two (η ₁₀₀ / η _RT ) was used as an index of the efficiency change during high-luminance driving. A larger value is more preferable.
(D) Change in chromaticity after high-temperature storage Each element is stored in a thermostat at 100 ° C. for 24 hours, and then light is emitted by applying a DC voltage so that the luminance becomes 1000 cd / m ² at room temperature. The chromaticity (x, y) at this time is compared with the chromaticity (x, y) when light is emitted at room temperature, and the difference between the x value and y value is expressed in the form of (Δx, Δy). It was used as an index of chromaticity change during high brightness driving. Smaller values of Δx and Δy are preferable.
(E) Durability after high-temperature storage Each element was stored in a constant temperature bath at 100 ° C. for 24 hours, and then the device was made to emit light by applying a DC voltage so that the luminance was 5000 cd / m ² at room temperature, and the luminance was 4000 cd. The time required to reach / m ² was used as an index of durability. In Tables 1 to 9 described below, the elements shown at the top of each table (that is, the elements 1-1, 2-1, 3-1, 4-1, 5-1, 6-1, 7- 1, 8-1 and 9-1) are described as relative values when the durability is 100. The larger the number, the better the durability.

  In Tables 1 to 9, the symbols “<” and “>” in the evaluation of chromaticity change and durability after high temperature storage mean inequality signs, for example “<0.005” in chromaticity change after high temperature storage. Means that the change in chromaticity was less than 0.005.

(Example 2) (Green ETL)
A device was fabricated in the same manner as in Example 1 except that the layer configuration was changed to the one shown below, and the results of performing the same evaluation as in Example 1 for the items described in Table 2 are shown in Table 2.
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-2: film thickness 3 nm
Fourth layer: H-1 and GD-2 (mass ratio 85:15): film thickness 30 nm
Fifth layer: Materials listed in Table 2: Film thickness 5 nm
Sixth layer: BCP and Li (mass ratio 99.4: 0.6): film thickness 25 nm

(Example 3) (Blue ETL)
A device was fabricated in the same manner as in Example 1 except that the layer configuration was changed to the one shown below, and the results of the same evaluation as in Example 1 for the items shown in Table 3 are shown in Table 3.
First layer: CuPc: film thickness 10 nm
Second layer: TPAC: film thickness 30 nm
Third layer: H-2 and BD-1 (mass ratio 90:10): film thickness 30 nm
Fourth layer: Materials described in Table 3: Film thickness 5 nm
5th layer: ET-2: film thickness 25 nm

(Example 4) (Blue ETL)
A device was fabricated in the same manner as in Example 1 except that the layer configuration was changed to the one shown below, and the results of the same evaluation as in Example 1 for the items shown in Table 4 are shown in Table 4.
First layer: 2-TNATA and F ₄ -TCNQ (mass ratio 99.7: 0.3): film thickness 120 nm
Second layer: NPD: film thickness 7 nm
Third layer: HT-1: film thickness 3 nm
Fourth layer: H-3 and BD-2 (mass ratio 85:15): film thickness 30 nm
Fifth layer: Materials listed in Table 4: Film thickness 5 nm
Sixth layer: BAlq: film thickness 25 nm

(Example 5) (Red ETL, EIL)
Table 5 shows the results of fabricating the device in the same manner as in Example 1 except that the layer configuration was changed to the following, and performing the same evaluation as in Example 1.
First layer: TCTA: film thickness 30 nm
Second layer: DTASi: film thickness 12 nm
Third layer: H-4 and RD-1 (mass ratio 90:10): film thickness 30 nm
Fourth layer: Materials described in Table 5: Film thickness 5 nm
Fifth layer: Materials listed in Table 5: Film thickness 50 nm

  Since the charge transport material of the present invention is excellent in electron injection and transport properties, stability to excitons and electrons, and heat resistance, when used as an electron transport material, high efficiency, low voltage, and efficiency after high-temperature storage, It was found that an element excellent in chromaticity and durability can be obtained.

Example 6 (Green Host, ETL)
A device was produced in the same manner as in Example 1 except that the layer configuration was changed to the one shown below, and the results of evaluating the items described in Table 6 by the same method as in Example 1 are shown in Table 6.
First layer: CuPc: film thickness 10 nm
Second layer: NPD: film thickness 25 nm
Third layer: Materials listed in Table 6: Film thickness 5 nm
Fourth layer: Host material described in Table 6 and GD-3 (mass ratio 90:10): film thickness 30 nm
Fifth layer: Materials listed in Table 6: Film thickness 5 nm
Sixth layer: ET-3: film thickness 40 nm

(Example 7) (Light blue host, ETL)
A device was produced in the same manner as in Example 1 except that the layer configuration was changed to the one shown below, and the results of evaluating the items described in Table 7 by the same method as in Example 1 are shown in Table 7.
First layer: LG101: film thickness 10 nm
Second layer: NPD: film thickness 115 nm
Third layer: Materials described in Table 7: Film thickness 5 nm
Fourth layer: Host material and Firpic (mass ratio 90:10) described in Table 7: Film thickness 30 nm
Fifth layer: Materials listed in Table 7: Film thickness 5 nm
Sixth layer: ET-1: film thickness 25 nm

Example 8 (Red host, ETL)
A device was fabricated in the same manner as in Example 1 except that the layer configuration was changed to the one shown below, and the results of evaluating the items described in Table 8 by the same method as in Example 1 are shown in Table 8.
First layer: LG101: film thickness 10 nm
Second layer: NPD: film thickness 27 nm
Third layer: Materials listed in Table 8: Film thickness 5 nm
Fourth layer: Host material described in Table 8 and RD-2 (mass ratio 93: 7): film thickness 30 nm
Fifth layer: Materials listed in Table 8: Film thickness 5 nm
Sixth layer: ET-4: film thickness 49 nm
7th layer: BCP: 1 nm

  Since the charge transport material of the present invention is excellent in electron injection and transport properties, exciton and electron stability, and heat resistance, it is highly efficient when used as a host material, and efficiency, chromaticity and durability after storage at high temperatures. A device excellent in the above can be obtained.

Example 9 (Coating, green 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, ultrasonically cleaned in 2-propanol, and then subjected to UV-ozone treatment for 30 minutes. Went. On this transparent anode (ITO film), PEDOT (poly (3,4-ethylenedioxythiophene)) / PSS (polystyrene sulfonic acid) aqueous solution (BaytronP (standard product)) was spin-coated (4000 rpm, 60 seconds), 120 A hole transporting buffer layer was formed by drying at a temperature of 10 ° C. for 10 minutes.
Next, a toluene solution containing 1% by mass of Compound 1 and 0.05% by mass of GD-1 as a host material was spin-coated (2000 rpm, 60 seconds) on the previous buffer layer to form a light emitting layer.
On this light emitting layer, ET-3 was vapor-deposited by 50 nm by a vacuum vapor deposition method to make an electron transport layer, and further, lithium fluoride 0.1 nm and metal aluminum 100 nm were vapor-deposited in this order to make a cathode.
This product is put in a glove box substituted with nitrogen gas without being exposed to the atmosphere, and sealed with a glass sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.). Thus, an organic electroluminescent element 9-1 was obtained. Moreover, except having changed the host material which comprises a light emitting layer into the material of Table 9, it carried out similarly and obtained the elements 9-2 to 9-4 and the comparative elements 9-1 to 9-3. Table 9 shows the results of evaluating the items described in Table 9 by the same method as in Example 1.

  As described above, it has been found that the charge transport material of the present invention can provide a film having a good film quality even when formed by a wet film forming method, and an element having a good performance can be obtained.

  From the results of Tables 1 to 9, the device of the present invention using the compound represented by any one of the general formulas (1) to (3) of the present invention is more efficient after high-temperature storage than the device of the comparative example. It can be seen that the change in color and the change in chromaticity are small and the durability after high temperature storage is excellent.

In the case of a light emitting device, a display device, and a lighting device, it is necessary to instantaneously emit light with high brightness through a high current density in each pixel portion, and the light emitting element of the present invention is designed to increase the light emission efficiency in such a case. Therefore, it can be used advantageously.
Further, the element of the present invention is excellent in luminous efficiency and durability even when used in a high temperature environment such as in-vehicle use, and is suitable for a light emitting device, a display device, and a lighting device.

  The structures of compounds other than the aforementioned compounds 1 to 11 and comparative compounds 1 to 11 used in Examples 1 to 9 are shown below.

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

Claims (22)

An organic electroluminescent device having a pair of electrodes consisting of an anode and a cathode on a substrate, and at least one organic layer including a light emitting layer between the electrodes,
Organic electroluminescence comprising a compound having an m-kinkphenyl structure represented by the following general formula (1) in any one of the at least one organic layer: element.
In the general formula (1), R ₁ represents an aryl group substituted on the central benzene ring of the general formula (1), and the R ₁ has an alkyl group.
m ₁ is the number of cyano groups substituted in the m-kinkphenyl structure in the general formula (1), and represents an integer of 3 or more and 10 or less.
n ₁ represents an integer of 1.
However, the compound represented by the general formula (1) does not have a benzene ring substituted with 3 or more cyano groups, has at least one cyano group substituted on the benzene ring, and It has a cyano group and R ₁ so that the sum of the number of benzene rings and the number of cyano groups substituted on the benzene ring is 9 or more and 16 or less. The organic electroluminescent element according to claim 1, wherein R ₁ is a phenyl group. The organic electroluminescent device according to claim 1, wherein the compound represented by the general formula (1) is the following compound 10.
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 electroluminescent element according to claim 4, wherein the iridium complex represented by the general formula (E-1) is represented by the following 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. The organic electroluminescent element according to claim 4, wherein the iridium complex represented by the general formula (E-1) is represented by the following general formula (E-6).
In General Formula (E-6), R _{1a to} R _1k 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 may be represented, 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.
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 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.
(X—Y) represents a monoanionic bidentate ligand.
n _E6 represents an integer of 1 to 3.   It has an organic layer adjacent to the said light emitting layer between the said light emitting layer and a cathode, This organic layer contains the compound represented by the said General formula (1), It is any one of Claims 1-6 The organic electroluminescent element according to item.   The organic electroluminescent element as described in any one of Claims 1-7 in which the said light emitting layer contains the compound represented by the said General formula (1).   The electron injection layer adjacent to the cathode is provided between the pair of electrodes, and the electron injection layer contains the compound represented by the general formula (1). The organic electroluminescent element as described.   The organic electroluminescent element according to claim 9, wherein the electron injection layer further contains an electron donating dopant.   The organic electroluminescent element according to claim 1, wherein at least one of the organic layers between the pair of electrodes is formed by a solution coating method.   The light-emitting device using the organic electroluminescent element as described in any one of Claims 1-11.   The display apparatus using the organic electroluminescent element as described in any one of Claims 1-11.   The illuminating device using the organic electroluminescent element as described in any one of Claims 1-11. A charge transport material represented by the following general formula (1).
In the general formula (1), R ₁ represents an aryl group substituted on the central benzene ring of the general formula (1), and the R ₁ has an alkyl group.
m ₁ is the number of cyano groups substituted in the m-kinkphenyl structure in the general formula (1), and represents an integer of 3 or more and 10 or less.
n ₁ represents an integer of 1.
However, the compound represented by the general formula (1) does not have a benzene ring substituted with 3 or more cyano groups, has at least one cyano group substituted on the benzene ring, and It has a cyano group and R ₁ so that the sum of the number of benzene rings and the number of cyano groups substituted on the benzene ring is 9 or more and 16 or less. The charge transport material according to claim 15, wherein R ₁ is a phenyl group. The charge transport material according to claim 15, wherein the compound represented by the general formula (1) is the following compound 10.
  The composition containing the charge transport material as described in any one of Claims 15-17.   A thin film comprising the charge transport material according to any one of claims 15 to 17. A compound represented by the following general formula (1).
In the general formula (1), R ₁ represents an aryl group substituted on the central benzene ring of the general formula (1), and the R ₁ has an alkyl group.
m ₁ is the number of cyano groups substituted in the m-kinkphenyl structure in the general formula (1), and represents an integer of 3 or more and 10 or less.
n ₁ represents an integer of 1.
However, the compound represented by the general formula (1) does not have a benzene ring substituted with 3 or more cyano groups, has at least one cyano group substituted on the benzene ring, and It has a cyano group and R ₁ so that the sum of the number of benzene rings and the number of cyano groups substituted on the benzene ring is 9 or more and 16 or less. A compound according to claim 20 R ₁ is a phenyl group. 21. The compound according to claim 20, wherein the compound represented by the general formula (1) is the following compound 10.