JP2012089810A - Organic electroluminescent element and charge transport material - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an organic electroluminescent element which has excellent luminous efficiency, excellent durability, and a low driving voltage with small voltage increase over time.SOLUTION: The organic electroluminescent element has, on a substrate, a pair of electrodes consisting of an anode and a cathode, and one or more organic layers including a light-emitting layer between the electrodes. At least one of the organic layers contains a specific triphenylene compound (for example, one of compounds shown as follows).

Description

  The present invention relates to an organic electroluminescent device and a charge transport material.

  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 materials such as iridium complexes and platinum complexes has led to higher efficiency of devices. In addition, a doped element using a light emitting layer in which a light emitting material is doped in a host material is widely used.
Development of the charge transport material contained in the host material used for a light emitting layer and other organic layers is also performed actively.
For example, Patent Document 1 describes a triphenylene compound having a substituent at a meta position with respect to the triphenylene of a benzene ring substituted with triphenylene, such as a compound represented by ref-1.

  Patent Document 2 discloses two triphenylene structures such as a triphenylene compound having two or more substituents such as a compound represented by ref-2 below and a compound represented by ref-3 below. Compounds having the above are described.

International Publication No. 09/021107 US Patent Application Publication No. 2006/0280965

  However, according to the study by the present inventors, the organic electroluminescence device using the compound having a triphenylene structure described in Patent Documents 1 and 2 requires further improvement from the viewpoint of driving voltage, and device driving. It has been found that there is a problem that the increase in voltage (voltage increase with time) is remarkable.

An object of the present invention is to provide an organic electroluminescence device having excellent luminous efficiency and durability, a low driving voltage, and a small increase in voltage with time.
Another object of the present invention is to provide a charge transport material that can be used for an organic electroluminescence device having excellent luminous efficiency and durability, low driving voltage, and small increase in time-dependent voltage.

According to the study by the present inventors, a compound having a structure in which a triphenylene skeleton and a phenyl group are linked by a phenylene group at the para position as shown in the following general formula (1) (a biphenyl group only at a specific position of the triphenylene skeleton). And a compound having at least one specific substituent in at least one of the phenyl group and the phenylene group.
That is, the present invention can be achieved by the following means.

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

(In General Formula (1), R _A and R _B each independently represents an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, a fluorine atom, or a group formed by combining these. represents an integer of 0 to 4, q is an integer of 0-5. However, p + q is when one or more of an integer .R _a and _{R B} there are a plurality, the plurality of _{R a} and _{R B,} respectively it is the same or different and bonded to each other is .2 or more R _B may, together with the benzene ring B, a fluorene ring, may form a naphthalene ring, or phenanthrene ring, the fluorene ring, a naphthalene ring, or phenanthrene ring May have an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, a fluorine atom, or a group formed by a combination thereof. R _B do not form a condensed ring and benzene ring A.)
[2]
The organic electroluminescence device according to [1], wherein R _A and R _B are each independently represented by the following group (Arx).

(In the group (Arx), Ara to Ard each independently represents a ring selected from a benzene ring, a naphthalene ring, a fluorene ring, and a phenanthrene ring. Na, nb, and nc each independently represent 0 or 1, and nd represents 1 represents a single bond when na, nb and nc are 0. Ara to Ard each independently represents an alkyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, a silyl group, or fluorine. The alkyl group, the phenyl group, the naphthyl group, the fluorenyl group, the phenanthryl group, or the silyl group, which may be substituted with an atom, is further substituted with an alkyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, a silyl group, or It may be substituted with a fluorine atom, and * is a bond to benzene ring A or benzene ring B in formula (1). Representing the site.)
[3]
The organic electroluminescent element according to the above [1] or [2], wherein the compound represented by the general formula (1) has a molecular weight of 400 or more and 1000 or less.
[4]
The organic electroluminescent element according to any one of the above [1] to [3], wherein the light emitting layer contains at least one phosphorescent material.
[5]
The organic electroluminescent element according to the above [4], wherein the phosphorescent material is 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. )
[6]
The organic electroluminescent element according to the above [5], wherein the phosphorescent material 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 represents 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. )
[7]
The organic electroluminescent element according to the above [5], wherein the phosphorescent material 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 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, a trifluorovinyl group, or —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 is independently. Represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
Any two of R _{1a to} R _1k may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl, or heteroaryl; The -7 membered ring may further have a substituent Z.
Z is independently a halogen atom, -R ", -OR", -N (R ") ₂ , -SR", -C (O) R ", -C (O) OR", -C (O) _{N (R ") 2, -CN} , -NO 2, -SO 2, -SOR", - SO 2 R ", or _-SO 3 R" represents, R "are each independently a hydrogen atom, an alkyl group, A perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group is represented.
(X—Y) represents a monoanionic bidentate ligand.
n _E6 represents an integer of 1 to 3. )
[8]
The organic electroluminescent element according to any one of the above [1] to [7], wherein the light emitting layer contains the compound represented by the general formula (1).
[9]
[1] to [7], wherein the compound represented by the general formula (1) is contained in an organic layer between the light emitting layer and the cathode and adjacent to the light emitting layer. Organic electroluminescent device.
[10]
The light-emitting device containing the organic electroluminescent element of any one of said [1]-[9].
[11]
The display apparatus containing the organic electroluminescent element of any one of said [1]-[9].
[12]
The illuminating device containing the organic electroluminescent element of any one of said [1]-[9].
[13]
A charge transport material represented by the following general formula (1).

(In General Formula (1), R _A and R _B each independently represents an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, a fluorine atom, or a group formed by combining these. represents an integer of 0 to 4, q is an integer of 0-5. However, p + q is when one or more of an integer .R _a and _{R B} there are a plurality, the plurality of _{R a} and _{R B,} respectively it is the same or different and bonded to each other is .2 or more R _B may, together with the benzene ring B, a fluorene ring, may form a naphthalene ring, or phenanthrene ring, the fluorene ring, a naphthalene ring, or phenanthrene ring May have an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, a fluorine atom, or a group formed by a combination thereof. R _B do not form a condensed ring and benzene ring A.)

According to the present invention, it is possible to provide an organic electroluminescence device having excellent luminous efficiency and durability, a low driving voltage, and a small voltage rise with time.
In addition, according to the present invention, a charge transport material that can be used for an organic electroluminescent device having excellent luminous efficiency and durability, low driving voltage, and small increase in voltage with time can be provided.

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

In the present invention, the substituent groups A and B are defined as follows.
(Substituent group A)
An alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, t-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 6 to 6 carbon atoms). 0, 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 to 20 carbon atoms). 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, and more. Preferably it is C1-C20, Most preferably, it is C1-C10, for example, a methoxy, an ethoxy, butoxy, 2-ethylhexyloxy etc. are mentioned), an aryloxy group (preferably C6-C30, More preferably it has 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, for example phenyl And 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 having a carbon number) 7-30, More preferably, it is C7-20, Most preferably, it is C7-12, for example, phenyloxycarbonyl etc. are mentioned. ), 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. Moreover, the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above. Moreover, the substituent substituted by the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above.

(Substituent group B)
An alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, t-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 6 to 6 carbon atoms). 0, particularly preferably 6 to 12 carbon atoms, including phenyl, p-methylphenyl, naphthyl, anthranyl, etc.), cyano group, heterocyclic group (including aromatic heterocyclic group, preferably carbon The hetero atom is, for example, a nitrogen atom, oxygen atom, sulfur atom, phosphorus atom, silicon atom, selenium atom, tellurium atom, specifically pyridyl. , Pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, Benzimidazolyl, Nzothiazolyl, carbazolyl group, azepinyl group, silylyl group, etc.) These substituents may be further substituted, and examples of the further substituents include groups selected from the above-mentioned substituent group B. . Moreover, the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group B described above. Moreover, the substituent substituted by the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group B described above.

  The organic electroluminescent device of the present invention is 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 the substrate, the organic layer Of these, at least one layer contains a compound represented by the following general formula (1).

(In General Formula (1), R _A and R _B each independently represents an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, a fluorine atom, or a group formed by combining these. represents an integer of 0 to 4, q is an integer of 0-5. However, p + q is when one or more of an integer .R _a and _{R B} there are a plurality, the plurality of _{R a} and _{R B,} respectively it is the same or different and bonded to each other is .2 or more R _B may, together with the benzene ring B, a fluorene ring, may form a naphthalene ring, or phenanthrene ring, the fluorene ring, a naphthalene ring, or phenanthrene ring May have an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, a fluorine atom, or a group formed by a combination thereof. R _B do not form a condensed ring and benzene ring A.)

The host material of the light emitting layer or the charge transport material of the organic layer between the light emitting layer and the cathode and adjacent to the light emitting layer has an energy gap in a thin film state than the light emitting material (if the light emitting material is a phosphorescent light emitting material, a thin film When the lowest excited triplet (T ₁ ) energy in the state is large, quenching of light emission can be suppressed, which is advantageous for improving 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.
According to the study by the present inventors, as in the compound represented by the general formula (1), a compound having a structure in which a triphenylene skeleton and a phenyl group are linked by a phenylene group at the para position (only at a specific position of the triphenylene skeleton). In addition, a compound having a structure having a biphenyl group as a substituent is π compared to a compound having a structure in which a triphenylene skeleton and a phenyl group are linked at the meta position by a phenylene group (such as Comparative Compound 1 in Comparative Examples described later). Since the conjugated system widens, it is considered that the energy gap is appropriately reduced and charges are easily injected.
In general formula (1), at least one of benzene ring A and benzene ring B has at least one substituent as an alkyl group, phenyl group, fluorenyl group, naphthyl group, phenanthryl group, silyl group, fluorine. It has been found that a material excellent in heat resistance, efficiency, and element durability can be obtained when it has atoms or a group formed by combining these. In particular, even when a phenyl group, a fluorenyl group, a naphthyl group, or a phenanthryl group is used as a substituent, it is considered that the energy gap has an appropriate size and the T ₁ energy also has an appropriate size.
Further, it was found that, as the further substituent, the phenanthrene ring has a low ionization potential, so that the driving voltage is lowered, whereas the triphenylene ring has a high ionization potential, so that the driving voltage is increased.
The T ₁ energy in the film state of the compound represented by the general formula (1) is preferably 2.39 eV (55 kcal / mol) or more and 3.47 eV (80 kcal / mol) or less and preferably 2.49 eV (57. 5 kcal / mol) to 3.25 eV (75 kcal / mol) is more preferable, and 2.60 eV (60 kcal / mol) to 3.04 eV (70 kcal / mol) is more preferable. 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.

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

(In General Formula (1), R _A and R _B each independently represents an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, a fluorine atom, or a group formed by combining these. represents an integer of 0 to 4, q is an integer of 0-5. However, p + q is when one or more of an integer .R _a and _{R B} there are a plurality, the plurality of _{R a} and _{R B,} respectively it is the same or different and bonded to each other is .2 or more R _B may, together with the benzene ring B, a fluorene ring, may form a naphthalene ring, or phenanthrene ring, the fluorene ring, a naphthalene ring, or phenanthrene ring May have an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, a fluorine atom, or a group formed by a combination thereof. R _B do not form a condensed ring and benzene ring A.)

  When the general formula (1) has a hydrogen atom, an isotope (such as deuterium atom) is also included. In this case, all hydrogen atoms in the compound may be replaced with isotopes, or a mixture in which a part is a compound containing isotopes may be used.

In General Formula (1), R _A and R _B each independently represent an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, a fluorine atom, or a group formed by combining these.

When R _A and R _B represent an alkyl group, the alkyl group is preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, from the viewpoint of charge transportability. is there. For example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl group, 1,1-dimethylpropyl Group, 2-methylpentyl group, n-hexyl group, cyclohexyl group, 4-methylpentyl group, 3-methylpentyl group, 2-methylpentyl group, 3,3-dimethylbutyl group, 2,2-dimethylbutyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, etc. are mentioned, methyl group, ethyl group, n-propyl group, isopropyl group , N-butyl group, isobutyl group, sec-butyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl group, or 1,1-dimethyl Propyl group is preferred, methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, neopentyl group, or 1,1-dimethylpropyl group is more preferred, and methyl group or t-butyl group is still more preferred. .

When _RA represents an alkyl group, if a bulky group is used as the alkyl group, twisting between the benzene ring A and the triphenylene ring or between the benzene ring A and the benzene ring B increases, and charge transportability and durability are increased. Among the above, a methyl group is particularly preferable because of the lowering of the amount.

If R _B represents an alkyl group, the alkyl group, for the reason that a high chemical stability is absent proton chemical highly reactive benzylic position, especially t- butyl group Among the above are preferred.

R _A and R _B are each independently a fluorine atom, substituted or unsubstituted alkyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted It may be a phenanthryl group or a substituted or unsubstituted silyl group.
In the substituted or unsubstituted alkyl group, the substituent is a fluorine atom, a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, or a silyl group. If possible, these further include a fluorine atom, a phenyl group, a fluorenyl group. , A naphthyl group, a phenanthryl group, or a silyl group.
If R _B is to represent a substituted or unsubstituted alkyl group, examples of the substituent group is preferably a substituted or unsubstituted phenyl group, or a fluorine atom, more preferably, unsubstituted phenyl group, or a fluorine atom It is.
If R _B is to represent a substituted or unsubstituted phenyl group, the substituent group is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted silyl group, or a fluorine An atom, more preferably a substituted or unsubstituted alkyl group (preferably a perfluoroalkyl group as the substituted alkyl group), an unsubstituted phenyl group, a silyl group substituted by an alkyl group, a silyl substituted by a phenyl group A group or a fluorine atom, and the preferred range of the alkyl group is the same as in the case where R _A and R _B represent an alkyl group.
R _B is a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted naphthyl group, or Preferred substituents when representing a substituted or unsubstituted phenanthryl group substituents when the R _B represents a substituted phenyl group This is the same as the preferred range.
If R _B is to represent a substituted or unsubstituted silyl group, the substituent group is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, more preferably an unsubstituted alkyl group Or an unsubstituted phenyl group. The preferred range of the alkyl group is the same as in the case where R _A and R _B represent an alkyl group.

R _A and R _B may each independently be an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, or a group formed by combining fluorine atoms. As a combination, any number of groups selected from these may be combined, and the same group may be combined. Among the above, the group in the case of combining two is, for example, a group in which a fluorine atom is substituted on an alkyl group, a group in which a fluorine atom is substituted on a phenyl group, a group in which an alkyl group is substituted on a phenyl group, or a silyl group Groups substituted with alkyl groups, groups substituted with phenyl groups on silyl groups, groups substituted with phenyl groups on phenyl groups (biphenyl groups), groups substituted with alkyl groups on fluorenyl groups, groups substituted with phenyl groups on fluorenyl groups Etc.
The number of groups to be combined is preferably 2 to 8 and more preferably from the viewpoints of charge transportability, solubility in solvents, sublimation and vapor deposition, thermal stability of the film state, energy gap, T1 energy, and the like. Is 2-6, more preferably 2-4.
In addition, the range of the preferable alkyl group in the case of combining an alkyl group is the same as the above.

Moreover, one of the preferable embodiments as R _A and R _B is a case represented by the following group (Arx).

  (In the group (Arx), Ara to Ard each independently represents a ring selected from a benzene ring, a naphthalene ring, a fluorene ring, and a phenanthrene ring. Na, nb, and nc each independently represent 0 or 1, and nd represents 1 represents a single bond when na, nb and nc are 0. Ara to Ard each independently represents an alkyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, a silyl group, or fluorine. The alkyl group, the phenyl group, the naphthyl group, the fluorenyl group, the phenanthryl group, or the silyl group, which may be substituted with an atom, is further substituted with an alkyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, a silyl group, or It may be substituted with a fluorine atom, and * is a bond to benzene ring A or benzene ring B in formula (1). Representing the site.)

In the group (Arx), Ara to Ard are preferably a benzene ring or a naphthalene ring, and more preferably a benzene ring from the viewpoint of T1 and charge transportability.
The preferred range of the alkyl group in the group (Arx) is the same as described above.
Among na, nb, and nc, one or two is preferably 1, and one is more preferably 1.
Ara to Ard may each independently be substituted with an alkyl group, phenyl group, naphthyl group, fluorenyl group, phenanthryl group, silyl group, or fluorine atom, and the alkyl group, phenyl group, naphthyl group, fluorenyl group, phenanthryl The group or silyl group may be further substituted with an alkyl group, phenyl group, naphthyl group, fluorenyl group, phenanthryl group, silyl group, or fluorine atom. When Ara to Ard each independently represent a phenyl group, naphthyl group, fluorenyl group, or phenanthryl group, an alkyl group, phenyl group, naphthyl group, fluorenyl group, phenanthryl group, silyl group, or fluorine atom that further substitutes Ara to Ard Is preferably substituted at the meta or para position from the viewpoint of charge transportability and durability.

If R _A and R _B there are a plurality, or different in each of the plurality of R _A and R _B identical.

Two or more R _B may be bonded to each other to form a fluorene ring, a naphthalene ring, or a phenanthrene ring together with the benzene ring B in the general formula (1). Further, the formed fluorene ring, naphthalene ring, or phenanthrene ring may have an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, a fluorine atom, or a group formed by combining these. . Specific examples and preferred ranges of the alkyl group and the group formed in combination are the same as described above.
In particular, when two or more R _B are bonded to each other to form a fluorene ring together with the benzene ring B in the general formula (1), the group containing the benzene ring B in the general formula (1) is as follows: From the viewpoint of heat resistance, it is preferably a group having a structure (spirobifluorene ring structure) in which another fluorene ring is bonded to the 9-position of the fluorene ring at the 9-position.

  In the above structural formula, * represents a bonding position with the benzene ring A in the general formula (1).

However, R _B do not form a condensed ring and the benzene ring A in the general formula (1). When the R _B and the benzene ring A forms a condensed ring, conjugation too are energy gap becomes too small spread, it is not preferable to lower the luminous efficiency of the device.
For the same reason, a plurality of R _A are not bonded to each other to form a condensed ring with the benzene ring A or the benzene ring B.

R _A is preferably an alkyl group, a phenyl group, a silyl group substituted with an alkyl group, a silyl group substituted with a phenyl group, a fluorine atom, or a fluoroalkyl group. An alkyl group, a dimethylphenyl group, a trimethylsilyl group, or trifluoromethyl is preferred. Group is more preferable, and an alkyl group is still more preferable. The preferred range of the alkyl group is as described above, and the methyl group is most preferred.

The R _B, a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, a fluorenyl group in which the alkyl group is substituted or unsubstituted naphthyl group, a naphthyl group which phenyl group is substituted, unsubstituted phenanthryl group, a substituted Or an unsubstituted silyl group, a condensed ring to form a substituted or unsubstituted fluorene ring, a condensed ring to form a substituted or unsubstituted naphthalene ring, a condensed ring to form a substituted or unsubstituted phenanthrene ring, and these The preferred range of the substituent is as described above.
The R _B, t-butyl group, a biphenyl group, 9,9-dimethyl fluorenyl group, a triphenylsilyl group, a phenanthryl group, a naphthyl group, a terphenyl group, trifluorophenyl group, 3,5-diphenyl phenyl Are more preferable, and a biphenyl group, a 9,9-dimethylfluorenyl group, a phenanthryl group, a naphthyl group, a terphenyl group, and a 3,5-diphenylphenyl group are still more preferable.

R _B is, in view of charge transport property and durability, it is preferably substituted in the meta or para position of the benzene ring A in the formula (1).

In general formula (1), p represents an integer of 0 to 4, and q represents an integer of 0 to 5. However, p + q is an integer of 1 or more.
p is a benzene ring A and triphenylene ring by introduction of substituents R _A, not too large twisting between the benzene ring A with a benzene ring B, and the reason of excellent charge transporting property and durability, 0-3 An integer is preferable, and an integer of 0 to 2 is more preferable.
q is preferably an integer of 0 to 5, more preferably an integer of 0 to 4, more preferably an integer of 0 to 2, and an integer of 1 to 2 from the viewpoint of charge transport properties and thermal stability of the film state. Particularly preferred.
p + q is an integer of 1 or more from the viewpoint of heat resistance, efficiency, and element durability.

  The compound represented by the general formula (1) preferably has no substituent other than the substituent consisting of the benzene ring A in the triphenylene ring part from the viewpoint of ease of synthesis and high purity. A compound having 1 to 5 substituents consisting of substituent group A in addition to the substituent consisting of benzene ring A is considered to have substantially the same performance. From the viewpoint of driving voltage and durability, as a substituent other than the substituent consisting of the benzene ring A, an alkyl group having 1 to 6 carbon atoms (more preferably a methyl group or a t-butyl group), or 6 to 24 carbon atoms. Aryl group (more preferably phenyl group, biphenyl group, terphenyl group, fluorenyl group, phenanthrenyl group), heteroaryl group having 2 to 30 carbon atoms (more preferably pyridyl group, pyrimidyl group, triazyl group), silyl group (more A dimethylsilyl group, a diphenylsilyl group), a cyano group, a fluorine atom, a substituent identical to the substituent consisting of the benzene ring A, or a combination of these is preferred, and a substituent consisting of the benzene ring A The number of substituents other than 1 to 2 is more preferable.

  As known for the carbazole-based material described in WO2008 / 117889, a material in which part or all of the hydrogen atoms in the material of the present invention are substituted with deuterium atoms can also be preferably used as the charge transport material.

  The molecular weight of the compound represented by the general formula (1) is preferably 400 or more and 1000 or less, more preferably 450 or more and 900 or less, and more preferably 500 or more and 800 or less. If the molecular weight is 400 or more, a high-quality amorphous thin film can be formed, and if the molecular weight is 1000 or less, it is preferable in terms of solubility in a solvent, sublimation, and appropriate deposition.

When a blue phosphorescent light emitting material having a large T ₁ energy is used as the light emitting material of the organic electroluminescent element, the compound represented by the general formula (1) is preferably contained in the light emitting layer or the electron transport layer.
If the T ₁ energy as a light emitting material for an organic electroluminescent device is small green phosphorescent material than the blue phosphorescent material, or using a red phosphorescent material, a compound represented by the general formula (1) is contained in the light emitting layer It is preferred that

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 a vacuum deposition method, and the phosphorescence emission spectrum of the thin film is F-7000 Hitachi Spectrofluorimeter (Hitachi High-Technologies) under liquid nitrogen temperature. Use to measure. The T ₁ energy can be obtained by converting the rising wavelength on the short wavelength side of the obtained emission spectrum into energy units.

  The glass transition temperature (Tg) of the compound represented by the general formula (1) is 80 ° C. or higher and 400 ° C. or lower from the viewpoint of stably operating the organic electroluminescent device against heat generated during high temperature driving or driving the device. Preferably, the temperature is 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 a compound represented by General formula (1) below is illustrated, this invention is not limited to these.

The compound represented by the general formula (1) can be synthesized by combining known reactions such as a Suzuki coupling reaction. Moreover, it is compoundable by the method as described in international publication 05/013388 pamphlet, international publication 06/130598 pamphlet, international publication 09/021107 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.

The compound represented by the general formula (1) may be contained in any organic layer between the cathode and the anode of the organic electroluminescence device. The compound represented by the general formula (1) is preferably contained in the light emitting layer, or between the light emitting layer and the cathode and in the organic layer adjacent to the light emitting layer.
Examples of the organic layer that may contain the compound represented by the general formula (1) include 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. (A hole blocking layer, an electron blocking layer, etc.) can be mentioned, preferably a light emitting layer, an exciton blocking layer, a charge blocking layer, an electron transporting layer, or an electron injection layer, more preferably a light emitting layer. A layer, an exciton blocking layer, a charge blocking layer, or an electron transporting layer, more preferably a light emitting layer or a charge blocking layer.

When the compound represented by the general formula (1) is contained in the light emitting layer, the compound is preferably contained in an amount of 0.1 to 99% by mass and preferably 1 to 95% by mass with respect to the total mass of the light emitting layer. More preferably, it is more preferably 10 to 95% by mass.
When the compound represented by the general formula (1) is contained in an organic layer other than the light emitting layer, it is preferably contained in an amount of 70 to 100% by mass, and 85 to 100% by mass, based on the total mass of the organic layer. More preferably.

[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 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.
The preferred range of the charge transport material represented by the general formula (1) is as described above.

[Composition Containing Compound Represented by General Formula (1)]
The present invention also relates to a composition comprising a compound represented by the general formula (1). In the composition, the content of the compound represented by the general formula (1) is preferably 30 to 99% by mass, and preferably 50 to 97% by mass with respect to the total solid content in the composition. More preferably, it is 70 to 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 can form an organic layer of an organic electroluminescent device by a dry film forming method such as a vapor deposition method or a sputtering method, or a wet film forming method such as a transfer method or a printing method.

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

[Organic electroluminescence device]
The organic electroluminescent element of the present invention will be described in detail.
The organic electroluminescent element of the present invention is an organic electroluminescent element having a pair of electrodes comprising an anode and a cathode and at least one organic layer including a luminescent layer between the electrodes on a substrate, wherein the at least one layer In at least one of the organic layers, the compound represented by the general formula (1) of the present invention is included. 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 the organic electroluminescent element of the present invention, the light emitting layer preferably contains at least one phosphorescent material.
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 / hole 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 / hole 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 preferably contains at least one phosphorescent material.

(Luminescent material)
As the light emitting material in the present invention, any of phosphorescent light emitting materials, fluorescent light emitting materials and the like can be used.
The light emitting layer in the present invention can contain two or more kinds of light emitting materials in order to improve the color purity and widen the light emission wavelength region. At least one of the light emitting materials is preferably a phosphorescent light emitting 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 12112757, JP 2002/27 -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.

  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 ring substituent formed by B ₁ , Z ² and a carbon atom are linked. Then, the same condensed ring as described above may be formed.

  Examples of the ligand represented by (XY) include various known ligands used in conventionally known metal complexes. For example, “Photochemistry and Photophysics of Coordination Compounds” Springer-Verlag H. Published by Yersin, 1987, “Organometallic Chemistry-Fundamentals and Applications-” Liu Huabosha, Akio Yamamoto, published by 1982, etc. (for example, halogen ligands (preferably chlorine ligands), Nitrogen heteroaryl ligands (for example, bipyridyl, phenanthroline, etc.), diketone ligands (for example, acetylacetone, etc.) The ligand represented by (XY) is preferably a diketone or a picolinic acid. The derivative is most preferably acetylacetonate (acac) shown below from the viewpoint of obtaining stability of the complex and high luminous efficiency.

* Represents a coordination position to iridium.
As the ligand represented by (X—Y), the following general formulas (l-1) to (1-14) are preferable, but the present invention is not limited thereto.

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

  When Rx, Ry, and Rz represent a substituent, examples of the substituent include a substituent selected from the substituent group A. Preferably, Rx and Rz are each independently an alkyl group, a perfluoroalkyl group, a fluorine atom or an aryl group, more preferably an alkyl group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, A fluorine atom and an optionally substituted phenyl group are most preferred, and a methyl group, an ethyl group, a trifluoromethyl group, a fluorine atom and a phenyl group are most preferred. Ry is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, a fluorine atom or an aryl group, more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an optionally substituted phenyl group. And most preferably a hydrogen atom or a methyl group. Since these ligands are considered not to be sites where electrons are transported in the device or where electrons are concentrated by excitation, Rx, Ry, and Rz may be any chemically stable substituent, and the effects of the present invention can be achieved. Also has no effect.

  Moreover, it is also preferable to use the monoanionic ligand shown to general formula (I-15) as an auxiliary ligand.

R ^{I1 to} R ^I4 in the general formula (I-15) represent a substituent selected from the substituent group A, and B represents CR or a nitrogen atom. R represents a substituent selected from the substituent group A. R ^{I5 to} R ^I7 are each independently 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, halogen atom, an aryl group or a heteroaryl group, may further have a substituent a. 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. * Represents a coordination position to iridium in the general formula (E-1).
Any one of R ^I1 , R ^I5 , R ^I6 and R ^I7 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 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.
The preferred range of R ^{I1 to} R ^{I7 is the same as} the preferred range of R ^{T1 to} R ^T7 in general formula (E-3) described later. B is preferably CR, R is preferably an aryl group, more preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms (for example, a phenyl group, a tolyl group, a naphthyl group, etc.), particularly A phenyl group is preferred.

  (X-Y) is more preferably (I-1), (I-4), or (I-15), and particularly preferably (I-1) or (I-15). Complexes having these ligands can be synthesized in the same manner as in known synthesis examples by using corresponding ligand precursors. For example, it can synthesize | combine by the method shown below using commercially available difluoro acetylacetone similarly to the method of international publication 2009-073245 page 46.

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

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

A ^{E1 to} A ^E8 each independently 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.
The substituents Z are each independently a halogen atom, -R ", -OR", -N (R ") ₂ , -SR", -C (O) R ", -C (O) OR", -C ( O) represents N (R ″) ₂ , —CN, —NO ₂ , —SO ₂ , —SOR ″, —SO ₂ R ″, or —SO ₃ R ″, and each R ″ independently represents a hydrogen atom, alkyl Represents a group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
(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. Examples thereof include a cyclopentyl group and a cyclohexyl group, and a methyl group is particularly preferable.
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, for example, a phenyl group, a tolyl group, a naphthyl group, and the like. A phenyl group is particularly preferred.

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 a case where 0 to 2 are alkyl groups and the rest are all hydrogen atoms, and among R ^{T1 to} R ^T7 and R ′, 0 to 2 are methyl groups and the rest are all hydrogen atoms. Most preferred is an atom.

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 ′ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, cyano group, perfluoroalkyl group, trifluorovinyl group, —CO ₂ R, —C (O) R. , —NR ₂ , —NO ₂ , —OR, a halogen atom, an aryl group or a heteroaryl group, and 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, cyano group, perfluoroalkyl group, trifluorovinyl group, —CO ₂ R, —C (O) R. , —NR ₂ , —NO ₂ , —OR, a halogen atom, an aryl group or a heteroaryl group, and 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.

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

  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, a cyano group, a perfluoroalkyl group, a trifluorovinyl group, or —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.
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 case where R _1j and R _1k are linked to form a single bond is particularly preferable.
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 General Formula (E-7), R _{1a to} R _1i each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, a trifluorovinyl group, or —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 one 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 a cycloalkyl group, an aryl group, or a heteroaryl group; The condensed 4- to 7-membered ring may further have a substituent Z.
Z is independently a halogen atom, -R ", -OR", -N (R ") ₂ , -SR", -C (O) R ", -C (O) OR", -C (O) _{N (R ") 2, -CN} , -NO 2, -SO 2, -SOR", - SO 2 R ", or _-SO 3 R" represents, R "are each independently a hydrogen atom, an alkyl group, A perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group is represented.
(X—Y) represents a monoanionic bidentate ligand.
n _E7 represents an integer of 1 to 3.

In the formula _(E-7), definition and preferable ranges of R 1a _{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).

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

  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.

  Although it is preferable that the compound represented by general formula (E-1) is contained in a light emitting layer, the use is not limited and may further be 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 generally forming the light emitting layer in the light emitting layer. From the viewpoint of durability and external quantum efficiency, it is preferably contained in an amount of 1% by mass to 50% by mass, more preferably 2% by mass to 40% by mass.

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

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

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, In Q < ¹ >, Q < ² >, Q < ³ > and Q < ⁴ > Of the atoms bonded to Pt, at least one is preferably a carbon atom, more preferably two are carbon atoms, particularly preferably two are carbon atoms and two are nitrogen atoms.
Q ¹ , Q ² , Q ³ and Q ⁴ bonded to Pt by a carbon atom may be an anionic ligand or a neutral ligand, and the anionic ligand is a vinyl ligand, Aromatic hydrocarbon ring ligand (eg benzene ligand, naphthalene ligand, anthracene ligand, phenanthrene ligand), 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—) (such as phenylimino group), oxy group (—O—), thio group (—S—), phosphinidene group (—PR—) (such as phenylphosphinidene group), silylene group (-SiRR'-) (dimethylsilylene group, diphenylsilylene group, etc.), or a combination of these. Here, R and R ′ each independently include an alkyl group, an aryl group, and the like. These linking groups may further have a substituent.
From the viewpoint of the stability of the complex and the emission quantum yield, L ¹ , L ² and L ³ are preferably a single bond, an alkylene group, an arylene group, a heteroarylene group, an imino group, an oxy group, a thio group or a silylene group. More preferably a single bond, an alkylene group, an arylene group or an imino group, still more preferably a single bond, an alkylene group or an arylene group, still more preferably a single bond, a methylene group or a phenylene group, still more preferably. Single bond, disubstituted methylene group, more preferably single bond, dimethylmethylene group, diethylmethylene group, diisobutylmethylene group, dibenzylmethylene group, ethylmethylmethylene group, methylpropylmethylene group, isobutylmethylmethylene group, diphenyl Methylene group, methylphenylmethylene group, cyclohexanediyl group, A lopentanediyl group, a fluorenediyl group, and a fluoromethylmethylene group.
L ¹ is particularly preferably a dimethylmethylene group, a diphenylmethylene group, or a cyclohexanediyl group, and most preferably a dimethylmethylene group.
L ² and L ³ are most preferably a single bond.

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

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

General formula (C-2) is demonstrated. L ²¹ has the same meaning as ^{L 1} in the general formula (C-1), and the preferred ranges are 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 the carbon atom is preferably an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, or a fluorine atom. The substituent is appropriately selected for controlling the emission wavelength and potential, but in the case of shortening the wavelength, an electron donating group, a fluorine atom, and an aromatic ring group are preferable. For example, an alkyl group, a dialkylamino group, an alkoxy group, A fluorine atom, an aryl group, an aromatic heterocyclic group and the like are selected. 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 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 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.

  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. To express.)

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

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

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

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

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

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

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

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

General formula (C-6) is demonstrated. L ⁶¹ has the same meaning as L ^{1 in} formula (C-1), and the preferred range is also the same.

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

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

Y is an anionic acyclic ligand that binds to Pt. An acyclic ligand is one in which atoms bonded to Pt do not form a ring in the form of a ligand. As an atom couple | bonded with Pt in Y, a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom are preferable, a nitrogen atom and an oxygen atom are more preferable, and an oxygen atom is the most preferable.
A vinyl ligand is mentioned as Y couple | bonded with Pt by a carbon atom. Examples of Y bonded to Pt with a nitrogen atom include an amino ligand and an imino ligand. Examples of Y bonded to Pt with an oxygen atom include an alkoxy ligand, an aryloxy ligand, a heteroaryloxy ligand, an acyloxy ligand, a silyloxy ligand, a carboxyl ligand, a phosphate ligand, Examples thereof include sulfonic acid ligands. Examples of Y bonded to Pt with a sulfur atom include alkyl mercapto ligands, aryl mercapto ligands, heteroaryl mercapto ligands, 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-6), one of more preferred embodiments is a platinum complex represented by the following general formula (C-7).

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

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

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

Examples of the platinum complex compound represented by the general formula (C-1) include Journal of Organic Chemistry 53,786, (1988), G.S. R. Newkome et al. ), Page 789, method described in left 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%.

The type of the fluorescent material is not particularly limited. For example, benzoxazole, benzimidazole, benzothiazole, styrylbenzene, polyphenyl, diphenylbutadiene, tetraphenylbutadiene, naphthalimide, coumarin, pyran, perinone, oxa Diazole, aldazine, pyralidine, cyclopentadiene, bisstyrylanthracene, quinacridone, pyrrolopyridine, thiadiazolopyridine, cyclopentadiene, styrylamine, condensed polycyclic aromatic compounds (anthracene, phenanthroline, pyrene, perylene, rubrene, pentacene, etc. ), 8-quinolinol metal complexes, various metal complexes represented by pyromethene complexes and rare earth complexes, polythiophene, polyphenylene, polyphenylene vinylene and other poly complexes Over compounds, organic silane, and may be derivatives of these.
Specific examples of the fluorescent material are shown below, but the present invention is not limited to these.

  The content of the fluorescent light emitting material in the light emitting layer of the present invention is preferably 1 to 30% by mass in the light emitting layer, more preferably 1 to 20% by mass, and still more preferably 1 to 10% by mass. .

  The thickness of the light emitting layer is not particularly limited, but is usually preferably 2 nm to 500 nm, and more preferably 5 nm to 200 nm, and more preferably 10 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 contain a material that does not have charge transporting properties and does not emit light.
Further, the light emitting layer may be a single layer or a multilayer of two or more layers, and each layer may contain the same light emitting material or host material, or each layer may contain a different material. When there are a plurality of light emitting layers, each of the light emitting layers may emit light with different emission colors.

(Host material)
The host material is a compound mainly responsible for charge injection and transport in the light emitting layer, and itself is a compound that does not substantially emit light. Here, “substantially does not emit light” means that the amount of light emitted from the compound that does not substantially emit light is preferably 5% or less, more preferably 3% or less of the total amount of light emitted from the entire device. Preferably it says 1% or less.
As the host material, a compound represented by the general formula (1) 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, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, aryl Amine, amino-substituted chalcone, styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatic tertiary amine compound, styrylamine compound, porphyrin compound, condensed aromatic hydrocarbon compound (fluorene, naphthalene, phenanthrene, triphenylene, etc.) , Polysilane compound, poly (N-vinylcarbazole), aniline copolymer, thiophene oligomer, polythiophene Conductive polymer oligomer, organic silane, carbon film, pyridine, pyrimidine, triazine, imidazole, pyrazole, triazole, oxazole, oxadiazol, fluorenone, anthraquinodimethane, anthrone, diphenylquinone, thiopyrandi Oxides, carbodiimides, fluorenylidenemethane, distyrylpyrazine, fluorine-substituted aromatic compounds, heterocyclic tetracarboxylic anhydrides such as naphthaleneperylene, phthalocyanines, metal complexes of 8-quinolinol derivatives, metal phthalocyanines, benzoxazoles, Examples thereof include various metal complexes represented by metal complexes having benzothiazol as a ligand and derivatives thereof (which may have a substituent or a condensed ring).
Of these, carbazole, dibenzothiophene, dibenzofuran, arylamine, fused aromatic hydrocarbon compounds, and metal complexes are particularly preferable.

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

  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. R _'8 is, R in the general formula (4-1) and (4-2)' is synonymous with _8.

  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 the general formula (1), the compound represented by the general formula (1) is 50% by mass or more and 99% by mass or less in all the host compounds. It is preferable.

  In addition to the light emitting material and the host material, the light emitting layer may contain additives such as a charge trapping agent, an alignment control agent, and an intermolecular interaction modifier. Any additive may be used, but a hydrocarbon compound is preferred.

[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.

[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, and L ^O1 represents a divalent to hexavalent linking group composed of 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). It may have a substituent selected from group A. R ^O1 is preferably an aryl group or a heteroaryl group, more preferably an aryl group. As a preferable substituent when the aryl group of R ^O1 has a substituent, an alkyl group, an aryl group or a cyano group can be mentioned, an alkyl group or an aryl group is more preferable, and an aryl group is still more preferable. When the aryl group of R ^O1 has a plurality of substituents, the plurality of substituents may be bonded to each other to form a 5- or 6-membered ring. The aryl group of R ^O1 is preferably a phenyl group which may have a substituent selected from substituent group A, more preferably a phenyl group which may be substituted with an alkyl group or an aryl group, More preferred is an unsubstituted phenyl group or 2-phenylphenyl group.

A ^{O1 to} A ^O4 each independently represent C—R ^A or a nitrogen atom. Of A ^{O1 to} A ^O4 , 0 to 2 are preferably nitrogen atoms, and 0 or 1 is more preferably a nitrogen atom. 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 selected from the substituent group A. The plurality of ^RA may be the same or different. R ^A is preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.

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

^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 the 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). These may have a substituent selected from the aforementioned substituent group A.
R ^{02 to} R ⁰⁴ are preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom or an aryl group, and most preferably a hydrogen atom.

  The compound represented by the general formula (O-1) has a glass transition temperature (Tg) of 100 ° C. from the viewpoint of 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.
It is preferable that 70-100 mass% is contained with respect to the total mass of the organic layer to add, and it is more preferable that the compound represented by general formula (O-1) is contained 85-100 mass%.

  The light emitting device of the present invention preferably contains at least one organic layer between the light emitting layer and the cathode, and the organic layer contains at least one compound represented by the following general formula (P). From the viewpoint of efficiency and driving voltage. Below, general formula (P) is demonstrated.

(In General Formula (P), R ^P represents an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). It represents, they represent an integer of good .nP have a substituent selected from the above-described substituent group a 1 to 10, if R ^P is plural, they may be the same or different. At least one of R ^P is a substituent represented by the following general formulas (P-1) to (P-3).

(In the general formulas (P-1) to (P-3), R ^{P1 to} R ^P3 and R ′ ^{P1 to} R ′ ^P3 are an alkyl group (preferably having 1 to 8 carbon atoms) and an aryl group (preferably having a carbon number). 6-30) or a heteroaryl group (preferably having 4 to 12 carbon atoms), which may have a substituent selected from the aforementioned substituent group A. n ^P1 and n ^P2 are 0 to It represents an integer of 4, and when R ^{P1 to} R ^P3 and R ′ ^{P1 to} R ′ ^P3 are plural, they may be the same or different, and L ^{P1 to} L ^P3 are a single bond, an aryl ring or a heteroaryl ring. Represents one of divalent linking groups consisting of: * represents a bonding position with the anthracene ring of the general formula (P)))

As R ^{P, (P-1)} preferred substituents other than the substituent represented by ~ (P-3) is an aryl group, more preferably a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group And more preferably a naphthyl group.
R ^{P1 to} R ^P3 and R ′ ^{P1 to} R ′ ^P3 are preferably either aryl groups or heteroaryl groups, more preferably aryl groups, still more preferably phenyl groups, biphenyl groups, terphenyl groups, It is either a naphthyl group, most preferably a phenyl group.
L ^{P1 to} L ^P3 are preferably any of a single bond and a divalent linking group comprising an aryl ring, more preferably a single bond, phenylene, biphenylene, terphenylene, or naphthylene, and even more preferably It is either a single bond, phenylene, or naphthylene.

  Although the specific example of a compound represented by general formula (P) is shown below, this invention is not limited to these.

  The compound represented by the general formula (P) can be synthesized by the method described in WO2003 / 060956, WO2004 / 080975 and the like. 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 formula (P) is contained in an organic layer between the light emitting layer and the cathode, but is preferably contained in a layer adjacent to the cathode.
It is preferable that 70-100 mass% is contained with respect to the total mass of the organic layer to add, and, as for the compound represented by general formula (P), it is more preferable that 85-100 mass% is contained.

(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), tetrafluoro-tetracyanoquinodimethane _(F 4 -TCNQ), and molybdenum oxide.

  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 an electron transport material, the compound represented by General formula (1) of this 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 3 nm to 100 nm, and still more preferably 5 nm to 50 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 3 nm to 100 nm, and still more preferably 5 nm to 50 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. Obtainable.
The driving method of the organic electroluminescence device of the present invention is described in JP-A-2-148687, JP-A-6-301355, JP-A-5-29080, 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 substrate shape, electrode shape, organic layer thickness, inorganic layer thickness, organic layer refractive index, inorganic layer refractive index, 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 in FIG. 2 includes a transparent substrate (support substrate) 2, an organic electroluminescent element 10, a sealing container 16, and the like.

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

  The use of the light-emitting device of the present invention is not particularly limited, and for example, 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 1

4,4,5,5-tetramethyl-2- (triphenylene-2-yl) -1,3,2-dioxaborane 1.77 g (5.00 mmol), 4-bromo-4′-t-butylbiphenyl 59 g (5.50 mmol), tris (dibenzylideneacetone) dipalladium (Pd ₂ (dba) ₃ ) 229 mg (0.25 mmol), 2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl (SPhos) 410 mg (1 0.000 mmol), 3.18 g (15.0 mmol) of potassium phosphate, 30 mL of 1,2-dimethoxyethane (DME), and 15 mL of pure water were mixed and heated to reflux for 10 hours in a nitrogen atmosphere. After adding 200 mL of toluene to the reaction solution and cooling to room temperature, the solid content was separated by Celite filtration. After the organic layer was extracted by liquid separation, the solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent: toluene). Furthermore, 1.30g of compound 1 was obtained by recrystallizing with toluene / ethanol (4: 1) (yield 60%).
NMR data of Compound 1
¹ H NMR (400 MHz, in DMSO-d6); δ (ppm) = 9.10 (s, 1H), 9.06-9.03 (m, 1H), 8.93 (d, 1H), 8. 87-8.82 (m, 3H), 8.12-8.07 (m, 3H), 7.85 (d, 2H), 7.78-7.70 (m, 6H), 7.54 ( d, 2H), 1.35 (s, 9H) ppm. MS (MALDI-TOF): m / z = 437.2 ([M + H] ^< +>).

Synthesis Example 2 Synthesis of Compound 2

4,4,5,5-tetramethyl-2- (triphenylene-2-yl) -1,3,2-dioxaborane 7.08 g (20.0 mmol), p-bromoiodobenzene 22.6 g (80.0 mmol) , Palladium acetate (Pd (OAc) ₂ ) 135 mg (0.60 mmol), triphenylphosphine (PPh ₃ ) 629 mg (2.40 mmol), sodium carbonate 4.24 g (40.0 mmol), DME 100 mL, pure water 50 mL were mixed. The mixture was heated to reflux for 6 hours under a nitrogen atmosphere. After the reaction solution was cooled to room temperature, the solid content was filtered and washed successively with pure water, ethanol, and hexane. This solid was washed with ethanol to obtain 6.15 g of synthetic intermediate 1 (yield 80%).
Synthesis intermediate 1 3.60 g (9.39 mmol), bis (pinacolato) diboron 3.58 g (14.1 mmol), [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride dichloromethane complex (1: 1 ) (PdCl ₂ (dppf) ₂ ) 229 mg (0.28 mmol), potassium acetate (AcOK) 2.77 g (28.2 mmol), dimethyl sulfoxide (DMSO) 80 mL are mixed and stirred at 70 ° C. for 3 hours under nitrogen atmosphere. did. The reaction solution was poured into ice water, the precipitated solid was filtered, and washed successively with pure water and methanol. Thereafter, the product was purified by silica gel chromatography (developing solvent toluene: hexane = 1: 1) to obtain 1.30 g of synthetic intermediate 2 (32%).
Synthetic Intermediate 2 1.46 g (3.50 mmol), Synthetic Intermediate 3 1.66 g (3.85 mmol), Tris (dibenzylideneacetone) dipalladium 96 mg (0.11 mmol), SPhos 172 mg (0.42 mmol), phosphorus 1.49 g (7.00 mmol) of potassium acid, 15 mL of DME, and 7 mL of pure water were mixed and heated to reflux for 7 hours in a nitrogen atmosphere. After the reaction solution was cooled to room temperature, the solid content was filtered and washed successively with pure water, ethanol, and hexane. Thereafter, 700 mg of Compound 2 was obtained by washing with ethanol and toluene sequentially (40%).
NMR data of Compound 2
¹ H NMR (400 MHz, in DMSO-d6); δ (ppm) = 9.14 (s, 1H), 9.10-9.06 (m, 1H), 8.95 (d, 1H), 8. 89-8.84 (m, 3H), 8.18-8.05 (m, 12H), 7.85 (d, 4H), 7.80-7.75 (m, 8H), 7.52 ( t, 4H), 7.41 (t, 2H) ppm. MS (MALDI-TOF): m / z = 485.3 ([M + H] ^< +>).

(Synthesis Example 3) Synthesis of Compound 5

Synthesis intermediate 1 2.50 g (6.54 mmol), synthesis intermediate 4 2.74 g (7.2 mmol), tris (dibenzylideneacetone) dipalladium 180 mg (0.20 mmol), SPhos 540 mg (1.31 mmol), phosphorus 2.78 g (13.1 mmol) of potassium acid, 30 mL of DME, and 15 mL of pure water were mixed and heated to reflux for 6 hours under a nitrogen atmosphere. After the reaction solution was cooled to room temperature, the solid content was filtered and washed successively with pure water, ethanol, and hexane. Then, 1.4 g of compound 5 was obtained by washing with ethanol and toluene sequentially (39%).
NMR data of compound 5
¹ H NMR (400 MHz, in DMSO-d6); δ (ppm) = 8.96 (s, 1H), 8.83-8.68 (m, 7H), 8.06-7.85 (m, 9H) ), 7.77 (s, 1H), 7.74-7.57 (m, 10H) ppm. MS (MALDI-TOF): m / z = 557.2 ([M + H] ^< +>).

Synthesis Example 4 Synthesis of Compound 7

3,5-diphenylphenylboronic acid 27.4 g (100 mmol), 3-bromoiodobenzene 3.11 g (110 mmol), palladium acetate 1.12 g (5.0 mmol), triphenylphosphine 5.24 g (20.0 mmol), 27.6 g (200 mmol) of potassium carbonate, 100 mL of toluene, 20 mL of ethanol, and 40 mL of pure water were mixed and heated to reflux in a nitrogen atmosphere for 9 hours. Saturated saline was added to the reaction solution, and the organic layer was extracted. The organic layer was concentrated under reduced pressure and purified by silica gel column chromatography (developing solvent hexane / ethyl acetate (4: 1)) to obtain 38.1 g of synthetic intermediate 5 (yield 99%).
Synthesis intermediate 5 19.3 g (50.0 mmol), bis (pinacolato) diboron 15.2 g (60.0 mmol), [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride dichloromethane complex (1: 1) 1.25 g (1.5 mmol), 10.78 g (110 mmol) of potassium acetate, and 150 mL of DMSO were mixed and stirred at 70 ° C. for 8 hours under a nitrogen atmosphere. The reaction solution was poured into 300 mL of ice-cooled pure water, and the precipitated solid was filtered. This solid was purified by silica gel column chromatography (hexane / ethyl acetate (50: 1 → 20: 1 → 10: 1)), dissolved in toluene, and crystallized by adding hexane. 18.6g of body 6 was obtained (yield 86%).
Synthetic intermediate 6 4.32 g (10.0 mmol), 2-bromo-5-iodotoluene 3.27 g (11.0 mmol), palladium acetate 112 mg (0.5 mmol), triphenylphosphine 525 mg (2.0 mmol), carbonic acid 2.76 g (20.0 mmol) of potassium, 10 mL of toluene, 2 mL of ethanol, and 4 mL of pure water were mixed and heated to reflux for 11 hours in a nitrogen atmosphere. After the reaction, the organic layer was extracted by liquid separation, and then 1.5 g of synthetic intermediate 7 was obtained by silica gel column chromatography (developing solvent: hexane / ethyl acetate (in the order of 100: 1, 50: 1, 10: 1)). Obtained (yield 32%).
Synthetic intermediate 7 1.43 g (3.0 mmol), 4,4,5,5-tetramethyl-2- (triphenylene-2-yl) -1,3,2-dioxaborane 1.06 g (3.0 mmol), 34 mg (0.15 mmol) of palladium acetate, 157 mg (0.60 mmol) of triphenylphosphine, 954 mg (9.0 mmol) of sodium carbonate, 30 mL of tetrahydrofuran (THF), and 10 mL of pure water were mixed and heated under a nitrogen atmosphere for 7.5 hours. Refluxed. After the reaction, hexane was added and the precipitate was filtered. The solid was purified by silica gel column chromatography (developing solvent: toluene / hexane (2: 3)), dispersed in ethanol, filtered, and washed with ethanol to obtain 1.35 g of compound 7 (yield) 72%).
NMR data of Compound 7
¹ H NMR (400 MHz, in DMSO-d6); δ (ppm) = 8.91-8.84 (m, 5H), 8.79 (s, 1H), 8.18 (s, 1H), 8. 02 (d, 2H), 7.93-7.64 (m, 15H), 7.57-7.52 (m, 5H), 7.44 (t, 2H), 2.48 (s, 3H) ppm. MS (MALDI-TOF): m / z = 623.3 ([M + H] ^< +>).

(Synthesis of Compounds 3, 4, 6, 8, 9, and 10)

Compound 3 is synthetic intermediate 3 as synthetic intermediate 8, compound 4 is synthetic intermediate 3 as synthetic intermediate 9, compound 6 is synthetic intermediate 3 as synthetic intermediate 10, and compound 9 is synthetic intermediate 3. Compound 10 was synthesized in the same manner as in Synthesis Example 2 except that Compound 10 was changed to Synthesis Intermediate 13 and Synthesis Intermediate 13 was changed to Synthesis Intermediate 13.
Compound 8 was synthesized in the same manner as in Synthesis Example 1 except that 4-bromo-4′-t-butylbiphenyl was changed to synthetic intermediate 11.

(Synthesis Example 5) Synthesis of Compound 12

4-biphenylboronic acid 7.92 g (40.0 mmol), 3,3′-dibromo-1,1′-biphenyl 24.96 g (80.0 mmol), palladium acetate (Pd (OAc) ₂ ) 449 mg (2.0 mmol) ), 2.10 g (8.0 mmol) of triphenylphosphine (PPh ₃ ), 8.48 g (80.0 mmol) of sodium carbonate, 150 mL of toluene, and 75 mL of water were mixed and heated to reflux for 8 hours under a nitrogen atmosphere. The reaction solution was cooled to room temperature, the organic layer was extracted by liquid separation, and then the origin component was removed by silica gel column chromatography (developing solvent: toluene). The solvent was distilled off under reduced pressure, washed with ethanol, heated and refluxed with 200 mL of toluene, and the solid matter precipitated at room temperature was separated by filtration. The obtained solution was concentrated, crystallized with hexane, and washed with hexane to obtain 8.82 g of synthetic intermediate 14 (yield 57%).

6.16 g (16.0 mmol) of synthetic intermediate 14, 4.88 g (19.2 mmol) of bis (pinacolato) diboron, [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride dichloromethane complex (1: 1 ) (PdCl ₂ (dppf)) 392 mg (0.48 mmol), potassium acetate (AcOK) 3.61 g (36.8 mmol), and dimethyl sulfoxide (DMSO) 100 mL were mixed and stirred at 70 ° C. for 4 hours under a nitrogen atmosphere. . After returning the reaction solution to room temperature, the solid content was filtered through Celite, the resulting solution was separated, and the organic layer was extracted. The organic layer was concentrated under reduced pressure and purified by silica gel chromatography (developing solvent: toluene) to obtain 3.77 g of synthetic intermediate 15 (yield 54%).
4,4,5,5-tetramethyl-2- (triphenylene-2-yl) -1,3,2-dioxaborane 7.08 g (20.0 mmol), 5-bromo-2-iodotoluene 11.88 g (40 0.0 mmol), tris (dibenzylideneacetone) dipalladium 549 mg (0.60 mmol), 2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl 985 mg (2.40 mmol), potassium phosphate 8.49 g (40.0 mmol) ), Toluene (80 mL) and water (40 mL) were mixed and heated to reflux for 5 hours under a nitrogen atmosphere. After returning the reaction solution to room temperature, the organic layer was extracted by liquid separation. The organic layer was concentrated under reduced pressure and purified by silica gel chromatography (developing solvent: toluene: hexane 1: 5) to obtain 5.06 g of synthetic intermediate 16 (yield 64%).

2.38 g (6.0 mmol) of the synthetic intermediate 16, 2.72 g (6.3 mmol) of the synthetic intermediate 15, 165 mg (0.18 mmol) of tris (dibenzylideneacetone) dipalladium, 2-dicyclohexylphosphino-2 296 mg (0.72 mmol) of ', 6'-dimethoxybiphenyl, 2.55 g (12.0 mmol) of potassium phosphate, 40 mL of toluene and 20 mL of water were mixed and heated to reflux for 3 hours under a nitrogen atmosphere. The solid content in the reaction solution was filtered through Celite, the organic layer was extracted by liquid separation, and the origin component was further removed by silica gel chromatography (developing solvent: toluene). The obtained solution was concentrated under reduced pressure and recrystallized three times with toluene / hexane (2: 1) to obtain 3.15 g of Compound 12 (yield 84%).
¹ H NMR (400 MHz, in DMSO-d6); δ (ppm) = 8.91-8.84 (m, 5H), 8.80 (s, 1H), 8.10 (d, 2H), 7. 93 (d, 2H), 7.84-7.71 (m, 15H), 7.66-7.62 (m, 2H), 7.56 (d, 1H), 7.51 (t, 2H) , 7.40 (t, 1H), 2.48 (s, 3H) ppm.

(Synthesis of Compounds 11 and 13-18)

Compound 11 was the same as Synthesis Example 2 except that synthetic intermediate 3 was changed to synthetic intermediate 14.
Compound 13 was synthesized in the same manner as in Synthesis Example 5 except that 5-bromo-2-iodotoluene was changed to 2-bromo-5-iodotoluene, and compound 14 was changed to synthesis intermediate 15 and synthesis intermediate 17. .
Compound 15 is synthetic intermediate 3 as synthetic intermediate 18, compound 16 is synthetic intermediate 2 as synthetic intermediate 19, synthetic intermediate 3 is as synthetic intermediate 18, and compound 17 is synthetic intermediate 3 as synthetic intermediate. 20 was synthesized in the same manner as in Synthesis Example 2 except that each was changed to 20.
Compound 18 was synthesized in the same manner as in Synthesis Example 5 except that synthetic intermediate 15 was changed to synthetic intermediate 21.

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. .

Example 1
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 compound layers were sequentially deposited on the transparent anode (ITO film) by vacuum deposition.
First layer: LG101: film thickness 10 nm
Second layer: NPD: film thickness 32 nm
Third layer: host material described in Table 1 and RD-1 (mass ratio 93: 7): film thickness 30 nm
Fourth layer: Material described in Table 1 (HBL material): film thickness 5 nm
Fifth layer: ET-1: film thickness 50 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.
The obtained laminate is put in a glove box substituted with nitrogen gas without being exposed to the atmosphere, and a glass sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.) are used. Then, elements 1-1 to 1-13 and comparative elements 1-1 to 1-5 were obtained. Table 1 shows the results of evaluating these elements from the viewpoint of efficiency, drive voltage, durability, and drive voltage increase by the following methods.

(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.
In Table 1, the value of the comparison element 1-1, in Table 2, the value of the comparison element 2-1, in Table 3, the value of the comparison element 3-1, and in Table 4, the value of the comparison element 4-1. In Table 5, the value of the comparison element 5-1, the value of the comparison element 6-1 in Table 6, and the value of the comparison element 7-1 in Table 7 are 10, respectively. Indicated. 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. In Table 1, the value of the comparison element 1-1, in Table 2, the value of the comparison element 2-1, in Table 3, the value of the comparison element 3-1, and in Table 4, the value of the comparison element 4-1. In Table 5, the value of the comparison element 5-1, the value of the comparison element 6-1 in Table 6, and the value of the comparison element 7-1 in Table 7 are 10, respectively. Indicated. The driving voltage is preferably as small as possible.

(C) a durable each element brightness continues to emit light by applying a DC voltage to be 5000 cd / ^{m 2,} luminance is used as an index of durability time taken until 4000 cd / ^{m 2.} In Table 1, the value of the comparison element 1-1, in Table 2, the value of the comparison element 2-1, in Table 3, the value of the comparison element 3-1, and in Table 4, the value of the comparison element 4-1. In Table 5, the value of the comparison element 5-1, the value of the comparison element 6-1 in Table 6, and the value of the comparison element 7-1 in Table 7 are 10, respectively. Indicated. The larger the number, the better the durability.

(D) drive voltage increase measured at the start of (c) the difference between the voltage value V of the (5000cd / ^{m 2),} the voltage value V of the durability evaluation at the end ^{(4000cd / m 2) '(} V'-V) ( The unit: V) was used as an index of drive voltage increase.

(Example 2)
Table 2 shows the results obtained by 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: BAlq and RD-2 (mass ratio 90:10): film thickness 30 nm
Fourth layer: Material described in Table 2 (HBL material): film thickness 5 nm
5th layer: ET-2: film thickness 50 nm

(Example 3)
Table 3 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: GD-1: film thickness 10 nm
Second layer: NPD: film thickness 30 nm
Third layer: Host material described in Table 3 and GD-1 (mass ratio 90:10): film thickness 30 nm
Fourth layer: ET-3: Film thickness 45 nm

Example 4
Table 4 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: 2-TNATA and F ₄ -TCNQ (mass ratio 99.7: 0.3): film thickness 160 nm
Second layer: NPD: film thickness 5 nm
Third layer: HT-1: film thickness 3 nm
Fourth layer: H-1 and GD-2 (mass ratio 85:15): film thickness 30 nm
Fifth layer: material described in Table 4 (HBL material): film thickness 5 nm
Sixth layer: BCP and Li (mass ratio 99.4: 0.6): film thickness 25 nm

(Example 5)
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: LG101: film thickness 10 nm
Second layer: NPD: film thickness 115 nm
Third layer: TPAC: film thickness 5 nm
Fourth layer: Host material and Firepic listed in Table 5 (mass ratio 90:10): film thickness 30 nm
5th layer: ET-4: film thickness 5 nm
6th layer: ET-1: film thickness 25 nm

(Example 6)
Table 6 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: 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-2: film thickness 3 nm
Fourth layer: H-2 and BD-1 (mass ratio 85:15): film thickness 30 nm
Fifth layer: material described in Table 6 (HBL material): film thickness 5 nm
Sixth layer: Alq: film thickness 25 nm

(Example 7)
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 By drying at a temperature of 10 ° C. for 10 minutes, a hole injecting and transporting layer having a thickness of about 50 nm was formed.
Next, a toluene solution containing 1% by mass of the host material described in Table 7 and 0.05% by mass of GD-1 was spin-coated (1000 rpm, 60 seconds) on the previous buffer layer, and the film thickness was about 50 nm. The light emitting layer was formed.
An ET-2 film having a thickness of about 45 nm was formed on this light emitting layer by a vacuum deposition method to form an electron injecting and transporting layer.
This laminated body 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.). Then, organic electroluminescent elements 7-1 to 7-5 and comparative elements 7-1 to 7-3 were obtained. Table 7 shows the results of evaluation similar to Example 1 performed on these elements.

From the above results, the device using the compound represented by the general formula (1) of the present invention has high issue efficiency, low driving voltage, excellent durability, and little voltage increase during driving.
On the other hand, a compound having a triphenylenyl group, a pyrenyl group, or an anthryl group as a substituent in the structure of the general formula (1) as in the comparative compound 3, 4, or 5 is effective when used in a device. In terms of voltage and voltage increase with time, it was inferior. This is because the compound having a triphenylenyl group, a pyrenyl group, or an anthryl group as a substituent in the structure of the general formula (1) has a too low π-conjugated system, and the T1 energy becomes too small, resulting in a decrease in efficiency. it is conceivable that.
Further, like Comparative Compounds 2 and 6, compounds having substituents at a plurality of positions in the triphenylene skeleton were inferior in device durability and voltage rise with time. In particular, when the triphenylene skeleton has a substituent containing two benzene rings at the ortho position, the decrease in durability was remarkable.

  The compounds used in Examples and Comparative Examples 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 element 11 ... Organic layer 12 ... Protective layer 14 ... Adhesive layer 16 ... Sealing container 20 ... Light emitting device 30 ... Light scattering member 31 ..Transparent substrate 30A ... light incident surface 30B ... light exit surface 32 ... fine particles 40 ... illumination device

Claims (13)

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

(In General Formula (1), R _A and R _B each independently represents an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, a fluorine atom, or a group formed by combining these. represents an integer of 0 to 4, q is an integer of 0-5. However, p + q is when one or more of an integer .R _a and _{R B} there are a plurality, the plurality of _{R a} and _{R B,} respectively it is the same or different and bonded to each other is .2 or more R _B may, together with the benzene ring B, a fluorene ring, may form a naphthalene ring, or phenanthrene ring, the fluorene ring, a naphthalene ring, or phenanthrene ring May have an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, a fluorine atom, or a group formed by a combination thereof. R _B do not form a condensed ring and benzene ring A.) The organic electroluminescent element according to claim 1, wherein R _A and R _B are each independently represented by the following group (Arx).

(In the group (Arx), Ara to Ard each independently represents a ring selected from a benzene ring, a naphthalene ring, a fluorene ring, and a phenanthrene ring. Na, nb, and nc each independently represent 0 or 1, and nd represents 1 represents a single bond when na, nb and nc are 0. Ara to Ard each independently represents an alkyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, a silyl group, or fluorine. The alkyl group, the phenyl group, the naphthyl group, the fluorenyl group, the phenanthryl group, or the silyl group, which may be substituted with an atom, is further substituted with an alkyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, a silyl group, or It may be substituted with a fluorine atom, and * is a bond to benzene ring A or benzene ring B in formula (1). Representing the site.)   The organic electroluminescent element of Claim 1 or 2 whose molecular weight of the compound represented by the said General formula (1) is 400-1000.   The organic electroluminescent element according to claim 1, wherein the light emitting layer contains at least one phosphorescent material. The organic electroluminescent element according to claim 4, wherein the phosphorescent material is 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 5, wherein the phosphorescent material 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 represents 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 5, wherein the phosphorescent material 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 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, a trifluorovinyl group, or —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 is independently. Represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
Any two of R _{1a to} R _1k may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl, or heteroaryl; The -7 membered ring may further have a substituent Z.
Z is independently a halogen atom, -R ", -OR", -N (R ") ₂ , -SR", -C (O) R ", -C (O) OR", -C (O) _{N (R ") 2, -CN} , -NO 2, -SO 2, -SOR", - SO 2 R ", or _-SO 3 R" represents, R "are each independently a hydrogen atom, an alkyl group, A perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group is represented.
(X—Y) represents a monoanionic bidentate ligand.
n _E6 represents an integer of 1 to 3. )   The organic electroluminescent element of any one of Claims 1-7 which contains the compound represented by the said General formula (1) in a light emitting layer.   The organic electroluminescence according to any one of claims 1 to 7, wherein the compound represented by the general formula (1) is contained in an organic layer between the light emitting layer and the cathode and adjacent to the light emitting layer. element.   The light-emitting device containing the organic electroluminescent element of any one of Claims 1-9.   The display apparatus containing the organic electroluminescent element of any one of Claims 1-9.   The illuminating device containing the organic electroluminescent element of any one of Claims 1-9. A charge transport material represented by the following general formula (1).

(In General Formula (1), R _A and R _B each independently represents an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, a fluorine atom, or a group formed by combining these. represents an integer of 0 to 4, q is an integer of 0-5. However, p + q is when one or more of an integer .R _a and _{R B} there are a plurality, the plurality of _{R a} and _{R B,} respectively it is the same or different and bonded to each other is .2 or more R _B may, together with the benzene ring B, a fluorene ring, may form a naphthalene ring, or phenanthrene ring, the fluorene ring, a naphthalene ring, or phenanthrene ring May have an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, a fluorine atom, or a group formed by a combination thereof. R _B do not form a condensed ring and benzene ring A.)

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