KR20130095740A - Organic electroluminescent element and charge transport material - Google Patents

Abstract

Provided is an organic electroluminescent element having excellent luminous efficiency and durability, further having a low driving voltage and a small rise in voltage over time. An organic electroluminescent device having a pair of electrodes comprising an anode and a cathode on a substrate, and at least one organic layer including a light emitting layer between the electrodes, wherein at least one of the organic layers has a specific triphenylene compound ( For example, the organic electroluminescent element containing any one of the following compounds.

Description

Organic electroluminescent device and charge transport material {ORGANIC ELECTROLUMINESCENT ELEMENT AND CHARGE TRANSPORT MATERIAL}

The present invention relates to organic electroluminescent devices and charge transport materials.

Organic electroluminescent elements (hereinafter also referred to as "elements" and "organic EL elements") have been actively researched and developed in that high-luminescence emission is obtained by low voltage driving. An organic electroluminescent element has an organic layer between a pair of electrodes, the electron injected from the cathode and the hole injected from the anode recombine in an organic layer, and use the energy of the excitons produced | generated for light emission.

In recent years, the use of phosphorescent materials, such as an iridium complex and a platinum complex, has advanced the efficiency of an element. Moreover, the dope type element which uses the light emitting layer which doped the light emitting material in the host material is employ | adopted widely.

Development of charge transport materials contained in host materials and other organic layers used in light emitting layers is also being actively carried out.

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 the compound represented by the following ref-1.

[Formula 1]

In addition, Patent Literature 2 describes a compound having two or more triphenylene structures, such as a triphenylene compound having two or more substituents, such as a compound represented by the following ref-2, and a compound represented by the following ref-3. It is.

(2)

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

However, according to the studies by the present inventors, the organic electroluminescent device using the compound having the triphenylene structures described in Patent Documents 1 and 2 requires further improvement in terms of driving voltage and voltage rise during driving of the device (time It has been found that there is a problem that the progressive voltage rise) is remarkable.

SUMMARY OF THE INVENTION An object of the present invention is to provide an organic electroluminescent device having excellent luminous efficiency and durability, further having a low driving voltage and a small rise in voltage over time.

Further, another object of the present invention is to provide a charge transport material which can be provided to an organic electroluminescent device having excellent luminous efficiency and durability, further having a low driving voltage and a small increase in voltage over time.

According to the studies of the present inventors, a compound having a structure in which a triphenylene skeleton and a phenyl group are linked at a para position with a phenylene group as in the following general formula (1) (having a biphenyl group as a substituent only at a specific position of the triphenylene skeleton) As a compound of a structure), it was found that the above problems can be solved by a compound having at least one specific substituent on at least one of the phenyl group and the phenylene group.

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

[One]

An organic electroluminescent device having a pair of electrodes consisting of an anode and a cathode on a substrate, and at least one organic layer including a light emitting layer between the electrodes, wherein at least one of the organic layers is represented by the following general formula (1): An organic electroluminescent element containing the compound shown.

(3)

(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 them. P is 0 ~ represents the four integer, q is an integer of 0 to 5. However, p + q is 1 is an integer equal to or greater than. R, if _a and R _B with a plurality exist, _B a plurality of R _a and R are different may be the same respectively may be 2 or more and R _B are linked to each other, and form a fluorene ring, naphthalene ring, or phenanthrene ring together with the benzene ring B, the fluorene ring, naphthalene ring or phenanthrene ring is an alkyl group, a phenyl group Or a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, a fluorine atom, or a group formed by a combination thereof, provided that R _B does not form a condensation with the benzene ring A).

[2]

The organic electroluminescent device according to the above [1], wherein R _A and R _B are each independently represented by the following group (Arx).

[Formula 4]

(In the group (Arx), Ara to Ard each independently represent a ring selected from benzene ring, naphthalene ring, fluorene ring and phenanthrene ring. Na, nb and nc each independently represent 0 or 1, nd represents 1. When na, nb and nc are 0, Ara to Arc represent a single bond, and Ara to Ard each independently represent an alkyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, a silyl group, Or a fluorine atom, and the alkyl group, phenyl group, naphthyl group, fluorenyl group, phenanthryl group, or silyl group may further be an alkyl group, phenyl group, naphthyl group, fluorenyl group, phenanthryl group, silyl group, or fluorine atom. May be substituted with * represents a binding site to benzene ring A or benzene ring B of the general formula (1).

[3]

The organic electroluminescent element as described in said [1] or [2] whose molecular weight of the compound represented by the said General formula (1) is 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 device according to the above [4], wherein the phosphorescent material is represented by the following General Formula (E-1).

[Chemical Formula 5]

(In General Formula (E-1), Z ¹ and Z ² each independently represent a carbon atom or a nitrogen atom.

A ₁ represents a group of atoms that together with Z ¹ and a nitrogen atom form a heterocyclic ring of 5 or 6 atoms.

B ₁ represents an atomic group which forms a 5 or 6 membered ring together with Z ² and a carbon atom.

(X-Y) represents a monoanionic bidentate ligand.

n _E1 represents an integer of 1 to 3)

[6]

The organic electroluminescent element as described in said [5] whose phosphorescent material represented by said general formula (E-1) is represented with the following general formula (E-2).

[Formula 6]

(In Formula (E-2), A ^E1 to A ^E8 each independently represent a nitrogen atom or CR ^E.

R ^E represents a hydrogen atom or a substituent.

(X-Y) represents a monoanionic bidentate ligand.

n _E2 represents an integer of 1 to 3)

[7]

The organic electroluminescent element as described in said [5] whose phosphorescent material represented by said general formula (E-1) is represented with the following general formula (E-6).

[Formula 7]

(In General Formula (E-6), R _1a to R _1k are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, a trifluorovinyl group, and -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. R each 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 a cycloalkane, an aromatic hydrocarbon or an aromatic heterocycle, and the condensed 4 to 7 membered ring May further have a substituent Z.

Z are each 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 '', and R '' Each 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.

(X-Y) represents a monoanionic bidentate ligand.

n _E6 represents an integer of 1 to 3)

[8]

The organic electroluminescent element as described in any one of said [1]-[7] which contains the compound represented by the said General formula (1) in a light emitting layer.

[9]

The organic electroluminescent element as described in any one of said [1]-[7] which contains the compound represented by the said General formula (1) in the organic layer adjacent to a light emitting layer between a light emitting layer and a cathode.

[10]

The light-emitting device containing the organic electroluminescent element in any one of said [1]-[9].

[11]

The display apparatus containing the organic electroluminescent element in any one of said [1]-[9].

[12]

The illuminating device containing the organic electroluminescent element in any one of said [1]-[9].

[13]

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

[Formula 8]

(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 them. P is 0 ~ represents the four integer, q is an integer of 0 to 5. However, p + q is 1 is an integer equal to or greater than. R, if _a and R _B with a plurality exist, _B a plurality of R _a and R are different may be the same respectively may be 2 or more R _B are bonded to each other, together with the benzene ring B, fluorene, and form a ring, a naphthalene ring, or a phenanthrene ring, and fluorene ring, naphthalene ring or phenanthrene ring is an alkyl group, It may have a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, a fluorine atom, or a group formed by combining them, provided that R _B does not form a condensation with the benzene ring A).

According to the present invention, it is possible to provide an organic electroluminescent element which has excellent luminous efficiency and durability, further has a low driving voltage and a small rise in voltage over time.

Moreover, according to this invention, the charge transport material which can be provided to the organic electroluminescent element which has the outstanding luminous efficiency and durability, and also has low drive voltage and small voltage rise over time can be provided.

1 is a schematic diagram showing an example of the configuration of an organic electroluminescent device according to the present invention.
2 is a schematic view showing an example of a light emitting device related to the present invention.
3 is a schematic view showing an example of a lighting apparatus according to the present invention.

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

(Substituent group A)

Alkyl group (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C10, For example, methyl, ethyl, isopropyl, t-butyl, n-octyl, n-decyl , n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), alkenyl group (preferably C2-C30, more preferably C2-C20, Especially preferably, it is C2-C10 For example, vinyl, allyl, 2-butenyl, 3-pentenyl, etc. are mentioned, Alkynyl group (preferably C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2 It is -10, for example, propargyl, 3-pentynyl, etc., an aryl group (preferably C6-C30, More preferably, it is C6-C20, Especially preferably, it is C6-C12 For example, phenyl, p-methylphenyl, naphthyl, anthranyl, etc. are mentioned. ), An amino group (preferably 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, for example, amino, methylamino, dimethylamino, diethylamino, dibenzylamino, Diphenylamino, ditolylamino, etc.), an alkoxy group (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C10, For example, methoxy, Ethoxy, butoxy, 2-ethylhexyloxy, etc.), an aryloxy group (preferably C6-C30, More preferably, it is C6-C20, Especially preferably, it is C6-C12, For example, phenyloxy, 1-naphthyloxy, 2-naphthyloxy, etc. are mentioned, heterocyclic oxy group (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, C1-C12, for example, pyridyl jade Ci, pyrazyloxy, pyrimidyloxy, quinolyloxy, etc.), an acyl group (preferably C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2-C12, For example, acetyl, benzoyl, formyl, pivaloyl, etc.), an alkoxycarbonyl group (preferably C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2-C12, For example, methoxycarbonyl, ethoxycarbonyl, etc. are mentioned, aryloxycarbonyl group (preferably C7-30, More preferably, it is C7-20, Especially preferably, it is C7-12, For example, phenyloxycarbonyl etc. are mentioned, Acyloxy group (preferably C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2-C10, For example, acetoxy , Benzoyloxy and the like Acylamino group (preferably C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2-C10, For example, acetylamino, benzoylamino etc. are mentioned), Alkoxy Carbonylamino group (preferably C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2-C12, For example, methoxycarbonylamino etc. are mentioned), Aryloxycarbonyl Amino group (preferably C7-30, More preferably, it is C7-20, Especially preferably, it is C7-12, For example, a phenyloxycarbonylamino etc. are mentioned), A sulfonylamino group (Preferably Is C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, methanesulfonylamino, benzenesulfonylamino etc. are mentioned), Sulphamo Group (preferably C0-30, More preferably, it is C0-20, Especially preferably, it is C0-12, For example, sulfamoyl, methyl sulfamoyl, dimethyl sulfamoyl, phenyl sulfamoyl, etc. are mentioned. Carbamoyl group (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, carbamoyl, methylcarbamoyl, diethylcarba Moyl, phenylcarbamoyl, etc.), an alkylthio group (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, methylthio, Ethylthio, etc.), an arylthio group (preferably C6-C30, More preferably, it is C6-C20, Especially preferably, it is C6-C12, For example, phenylthio etc. are mentioned. ), Heterocyclic thio group (bar Preferably they are C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2 -Benzthiazolylthio etc.), a sulfonyl group (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, mesyl, tosyl, etc. are mentioned. The sulfinyl group (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, methane sulfinyl, benzene sulfinyl, etc. are mentioned. ), A ureido group (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, ureido, methylureido, phenylureido, etc. are mentioned. ), Phosphate amide group (preferably 1 carbon -30, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, a diethyl phosphate amide, a phenyl phosphate amide, etc. are mentioned, A hydroxyl group, a mercapto group, and a halogen atom (For example, 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 (aromatic hetero A ring group is also included, Preferably it is C1-C30, More preferably, it is C1-C12, As a hetero atom, For example, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, a silicon atom, a selenium atom, a tellurium atom Specifically, pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, quinolyl, furyl, Thienyl, Selenofe , Telophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzooxazolyl, benzoimidazolyl, benzothiazolyl, carbazolyl group, azepinyl group, silolyl group, etc. The silyl group (preferably C3-C40, More preferably, it is C3-C30, Especially preferably, it is C3-C24, For example, a trimethylsilyl, triphenylsilyl, etc. are mentioned. ), Silyloxy group (preferably C3-C40, More preferably, it is C3-C30, Especially preferably, it is C3-C24, For example, trimethylsilyloxy, a triphenyl silyloxy, etc. are mentioned). And a phosphoryl group (for example, diphenylphosphoryl group, dimethylphosphoryl group, etc. may be mentioned). These substituents may be further substituted, and examples of the additional substituent include groups selected from Substituent Group A described above. In addition, the substituent substituted by the substituent may be substituted further and can mention group selected from the substituent group A demonstrated above as further substituent. In addition, the substituent substituted by the substituent substituted by the substituent may be substituted again and the group selected from the substituent group A demonstrated above as a further substituent is mentioned.

(Substituent group B)

Alkyl group (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C10, For example, methyl, ethyl, isopropyl, t-butyl, n-octyl, n-decyl , n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), alkenyl group (preferably C2-C30, more preferably C2-C20, Especially preferably, it is C2-C10 For example, vinyl, allyl, 2-butenyl, 3-pentenyl, etc. are mentioned, Alkynyl group (preferably C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2 It is -10, for example, propargyl, 3-pentynyl, etc., an aryl group (preferably C6-C30, More preferably, it is C6-C20, Especially preferably, it is C6-C12 For example, phenyl, p-methylphenyl, naphthyl, anthranyl, etc. are mentioned. ), A cyano group and a heterocyclic group (including aromatic heterocyclic groups, preferably 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and as a hetero atom, for example, a nitrogen atom, an oxygen atom, a 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, benzoimidazolyl, Benzothiazolyl, carbazolyl group, azepinyl group, silolyl group, etc.) are mentioned. These substituents may be further substituted, and examples of the additional substituent include groups selected from Substituent Group B above. In addition, the substituent substituted by the substituent may be substituted further and can mention group selected from the substituent group B demonstrated above as further substituent. In addition, the substituent substituted by the substituent substituted by the substituent may be substituted again and the group selected from the substituent group B demonstrated above as a further substituent is mentioned.

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 a substrate, wherein at least one of the organic layers is present. It contains the compound represented by following General formula (1).

[Chemical Formula 9]

(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 them. P is 0 ~ represents the four integer, q is an integer of 0 to 5. However, p + q is 1 is an integer equal to or greater than. R, if _a and R _B with a plurality exist, _B a plurality of R _a and R are different may be the same respectively may be 2 or more R _B are bonded to each other, together with the benzene ring B, fluorene, and form a ring, a naphthalene ring, or a phenanthrene ring, and fluorene ring, naphthalene ring or phenanthrene ring is an alkyl group, It may have a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, a fluorine atom, or a group formed by combining them, provided that R _B does not form a condensation with the benzene ring A).

The charge transport material of the host material of the light emitting layer or the organic layer between the light emitting layer and the cathode and adjacent to the light emitting layer has an energy gap in a thinner state than the light emitting material (when the light emitting material is a phosphorescent light emitting material, the lowest triplet excitation in the thin film state). If the term (T ₁ ) energy) is large, light emission can be suppressed from being quenched, which is advantageous for improving efficiency.

On the other hand, from the viewpoint of chemical stability of the compound, the energy gap and the T ₁ energy are preferably not too large.

According to the studies of the present inventors, a compound having a structure in which a triphenylene skeleton and a phenyl group are linked at a para position with a phenylene group as in the compound represented by the general formula (1) (a biphenyl group is substituted only at a specific position of the triphenylene skeleton) Compound of the structure which has, as a (pi) conjugated system is expanded compared with the compound (the comparative compound 1 in the comparative example mentioned later) which has the structure which connected the triphenylene frame | skeleton and the phenyl group by the phenylene group in meta position, It is thought that the energy gap is moderately small and charges are easy to be injected.

In formula (1), at least one of benzene ring A and benzene ring B is an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, a fluorine atom, or at least one substituent. When it has a group which combines these, it turned out that the material excellent in heat resistance, efficiency, and element durability is obtained. In particular, even in the case of having a phenyl group, a fluorenyl group, a naphthyl group, or a phenanthryl group as a substituent, the energy gap has an appropriate size, and the T ₁ energy is also considered to be an appropriate size.

In addition, in the case of having a phenanthryl group as the substituent, the phenanthrene ring can lower the driving voltage of the device because of its small ionization potential, but in the case of having a triphenylenyl group as the substituent (Comparative Compound 3 in Comparative Example described later) The triphenylene ring has a large ionization potential, and therefore, it has been found that the driving voltage of the device increases.

In the film state of the compound represented by formula ₍₁₎ T 1 energy, 2.39 eV (55 ㎉ / ㏖ ) more than 3.47 eV (80 ㎉ / ㏖) or less is preferred, and, 2.49 eV (57.5 ㎉ / ㏖ ) over 3.25 It is more preferable that it is eV (75 dl / mol) or less, and it is still more preferable that it is 2.60 eV (60 dl / mol) or more and 3.04 eV (70 dl / mol) or less. In particular, in the case of using a phosphorescent light emitting material as the light emitting material, it is preferable that the T ₁ energy falls within the above range.

[Compound represented by the general formula (1)

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

[Formula 10]

(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 them. P is 0 ~ represents the four integer, q is an integer of 0 to 5. However, p + q is 1 is an integer equal to or greater than. R, if _a and R _B with a plurality exist, _B a plurality of R _a and R are different may be the same respectively may be 2 or more R _B are bonded to each other, together with the benzene ring B, fluorene, and form a ring, a naphthalene ring, or a phenanthrene ring, and fluorene ring, naphthalene ring or phenanthrene ring is an alkyl group, It may have a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, a fluorine atom, or a group formed by combining them, provided that R _B does not form a condensation with the benzene ring A).

When General formula (1) has a hydrogen atom, an isotope (deuterium atom etc.) is also included. In this case, all the hydrogen atoms in the compound may be substituted with isotopes, or a mixture may be a compound in which a part contains isotopes.

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 them.

When R _A and R _B represent an alkyl group, from the viewpoint of charge transportability, the alkyl group is preferably an alkyl group having 1 to 6 carbon atoms, and more preferably an alkyl group having 1 to 4 carbon atoms. 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-dimethylpropyl group are preferable, and methyl group , An ethyl group, isopropyl group, n-butyl group, t-butyl group, neopentyl group, or 1,1-dimethylpropyl group is more preferable, and a methyl group or t-butyl group is more preferable.

In the case where R _A represents an alkyl group, when the bulky group is used as the alkyl group, the torsion between the benzene ring A and the triphenylene ring, or the benzene ring A and the benzene ring B increases, and the charge transportability and durability decrease. Among these, a methyl group is particularly preferable.

When R <_B> represents an alkyl group, t-butyl group is especially preferable among the above because the alkyl group does not have the proton of the chemically reactive benzyl position, and chemical stability is high.

R _A and R _B are each independently a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenane A trilyl group or a substituted or unsubstituted silyl group may be sufficient.

In the substituted or unsubstituted alkyl group, substituents include fluorine atom, phenyl group, fluorenyl group, naphthyl group, phenanthryl group, or silyl group, and if possible, these are further fluorine atom, phenyl group, fluorenyl group, naphthyl group, It may be substituted by the phenanthryl group or the silyl group.

When R _B represents a substituted or unsubstituted alkyl group, the substituent is preferably a substituted or unsubstituted phenyl group or a fluorine atom, and more preferably an unsubstituted phenyl group or a fluorine atom.

When R _B represents a substituted or unsubstituted phenyl group, the substituent is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted silyl group, or a fluorine atom, and more preferably. Preferably it is a substituted or unsubstituted alkyl group (preferably a perfluoroalkyl group as the substituted alkyl group), an unsubstituted phenyl group, the silyl group substituted by the alkyl group, the silyl group substituted by the phenyl group, or a fluorine atom, and this alkyl group As a preferable range of, it is the same as the case where said R _<A> , R <_B> represents an alkyl group.

Preferred substituents when R _B represents a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted phenanthryl group include a preferred range of a substituent when R _B represents a substituted phenyl group. same.

When R _B represents a substituted or unsubstituted silyl group, the substituent is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, and more preferably an unsubstituted alkyl group or an unsubstituted phenyl group. . As a preferable range of this alkyl group, it is the same as the case where said R _<A> , R <_B> represents an alkyl group.

R _A and R _B may each independently be an contribution formed by combining an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, or a fluorine atom. As a combination, you may combine some group selected from these, and may combine the same group. As a group in the case of combining two of the above, for example, a group in which a fluorine atom is substituted by an alkyl group, a group in which a fluorine atom is substituted by a phenyl group, a group in which an alkyl group is substituted by a phenyl group, a group in which an alkyl group is substituted by a silyl group, a phenyl group by a silyl group And a group in which a substituted phenyl group is substituted with a phenyl group (biphenyl group), a group in which an alkyl group is substituted with a fluorenyl group, a group in which a phenyl group is substituted with a fluorenyl group, and the like.

The number of groups to be combined is preferably 2 to 8, more preferably 2 from the viewpoints of charge transportability, solubility in solvents, sublimation and deposition titration, thermal stability of film state, energy gap, T ₁ energy and the like. It is -6 pieces, More preferably, it is 2-4 pieces.

In addition, the range of the preferable alkyl group in the case of combining an alkyl group is the same as the above.

In addition, one of the aspects preferable as R _<A> , R <_B> is a case represented by the following group (Arx).

[Formula 11]

(In the group (Arx), Ara to Ard each independently represent a ring selected from benzene ring, naphthalene ring, fluorene ring and phenanthrene ring. Na, nb and nc each independently represent 0 or 1, nd represents 1. When na, nb and nc are 0, Ara to Arc represent a single bond, and Ara to Ard each independently represent an alkyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, a silyl group, Or a fluorine atom, and the alkyl group, phenyl group, naphthyl group, fluorenyl group, phenanthryl group, or silyl group may further be an alkyl group, phenyl group, naphthyl group, fluorenyl group, phenanthryl group, silyl group, or fluorine atom. May be substituted with * represents a binding site to benzene ring A or benzene ring B of the general formula (1).

In group (Arx), it is preferable that it is a benzene ring or naphthalene ring from a viewpoint of T <_1> and charge transport property, and, as for Ara-Ard, it is more preferable that it is a benzene ring.

As a preferable range of the alkyl group in group (Arx), it is same as the above.

It is preferable that 1-2 of na, nb, and nc is 1, and it is more preferable that one is one.

Ara to Ard may be each independently substituted with an alkyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, a silyl group, or a fluorine atom, and the alkyl group, phenyl group, naphthyl group, fluorenyl group, phenanthryl group, or The silyl group may be further substituted with an alkyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, a silyl group, or a fluorine atom. When Ara to Ard each independently represents 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 further substituted with Ara to Ard It is preferable that an atom is substituted by a meta position or a para position from a charge transport property or durability viewpoint.

When two or more R _<A> and R <_B> exist, some R _<A> and R <_B> may be same or different, respectively.

Two or more R _{B 's} 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 General Formula (1). 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 them. About the alkyl group and the group formed in combination, a specific example and a preferable range are the same as the above.

In particular, the 2 or more R _B are linked to each other, in the case of forming the fluorene ring together with the benzene ring B in the general formula (1), indicating to groups containing a benzene ring B in the general formula (1), as Similarly, it is preferable from the viewpoint of heat resistance that it is a group of the structure (spirobifluorene ring structure) which the other fluorene ring couple | bonded at 9 position of the fluorene ring at 9 position.

[Chemical Formula 12]

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

However, R _B does not form a condensation with the benzene ring A in General formula (1). When R _B and the benzene ring A forms a chukhwan, is over-conjugated-up is the energy gap is too small, it is not preferable since the light emitting efficiency of the device decreases.

For the same reason, a plurality of R _{A 's} are bonded to each other and do not form a condensation ring with benzene ring A or 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, more preferably an alkyl group, a dimethylphenyl group, trimethylsilyl group, or trifluoromethyl group, Alkyl groups are more preferred. The preferable range of this alkyl group is as above-mentioned, and a methyl group is the most preferable.

R _B is a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, a fluorenyl group substituted with an alkyl group, an unsubstituted naphthyl group, a naphthyl group substituted with a phenyl group, an unsubstituted phenanthryl group, a substituted or unsubstituted group The silyl group is condensed to form a substituted or unsubstituted fluorene ring, and is condensed to form a substituted or unsubstituted naphthalene ring, and to be substituted to form a substituted or unsubstituted phenanthrene ring, and preferred ranges of these substituents are as described above. same.

R- _B is more preferably a t-butyl group, a biphenyl group, a 9,9-dimethylfluorenyl group, a triphenylsilyl group, a phenanthryl group, a naphthyl group, a terphenyl group, a trifluorophenyl group, or a 3,5-diphenylphenyl group. And a biphenyl group, 9,9-dimethylfluorenyl group, phenanthryl group, naphthyl group, terphenyl group, and 3,5-diphenylphenyl group are more preferable.

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

In general formula (1), p represents the integer of 0-4, q represents the integer of 0-5. However, p + q is an integer of 1 or more.

p is preferably an integer of 0 to 3 because the torsion between the benzene ring A and the triphenylene ring, the benzene ring A and the benzene ring B is not too large due to the introduction of the substituent R _A , and the charge transport property and durability are excellent. And the integer of 0-2 is more preferable.

From the viewpoint of charge transport characteristics and thermal stability of the film state, q is preferably an integer of 0 to 5, more preferably an integer of 0 to 4, still more preferably an integer of 0 to 2, and an integer of 1 to 2 Particularly preferred.

p + q is an integer of 1 or more from a viewpoint of heat resistance, efficiency, and element durability.

The compound represented by the general formula (1) preferably has no substituent in the triphenylene ring other than the substituent consisting of the benzene ring A from the viewpoint of the ease of synthesis and high purity, but in addition to the substituent consisting of the benzene ring A It is thought that the compound which has 1-5 substituents which consist of group A has a substantially equivalent performance. From the viewpoint of driving voltage and durability, examples of the substituents other than the substituent consisting of the benzene ring A include an alkyl group having 1 to 6 carbon atoms (more preferably a methyl group and a t-butyl group) and an aryl group having 6 to 24 carbon atoms (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 preferably dimethylsilyl Group, diphenylsilyl group), a cyano group, a fluorine atom, the same substituent as the substituent consisting of the benzene ring A, and any combination of these groups are preferable, and the number of substituents other than the substituent which consists of benzene ring A is 1 2 is more preferable.

As is known as the carbazole-based material described in WO 2008/117889, a material in which part or all of the hydrogen atoms of the material of the present invention is substituted with deuterium atoms can also preferably be used as the charge transport material.

It is preferable that the molecular weight of the compound represented by General formula (1) is 400 or more and 1000 or less, It is more preferable that it is 450 or more and 900 or less, It is more preferable that it is 500 or more and 800 or less. If the molecular weight is 400 or more, a good amorphous thin film can be formed. If the molecular weight is 1000 or less, it is preferable in view of solubility in solvents, sublimation, and deposition titration.

In the case of using a blue phosphorescent light emitting material having a large T ₁ energy as the light emitting material of the organic electroluminescent device, the compound represented by the general formula (1) is preferably contained in the light emitting layer or the electron transporting layer.

If the T ₁ energy as a light emitting material of an organic EL device uses a small green phosphorescent light-emitting material or a red phosphorescent light emitting material than the blue phosphorescent light emitting material, a compound represented by the general formula (1) is preferably contained in the light-emitting layer .

T ₁ energy can be obtained from the short wavelength end by measuring the phosphorescence emission spectrum of the thin film of the material. For example, on the cleaned quartz glass substrate, a material is formed into a film thickness of about 50 nm by the vacuum vapor deposition method, and the phosphorescence emission spectrum of a thin film is F-7000 Hitachi spectrophotometer (Hitachi High Technologies) under liquid nitrogen temperature. Measure with). 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.

From the viewpoint of stably operating the organic electroluminescent device at a high temperature during driving or at the time of driving the device, the glass transition temperature (Tg) of the compound represented by the general formula (1) is preferably 80 ° C or more and 400 ° C or less, and 100 ° C or more. It is more preferable that it is 400 degrees C or less, and it is still more preferable that they are 120 degreeC or more and 400 degrees C or less.

Although the specific example of a compound represented by General formula (1) below is illustrated, this invention is not limited to these.

[Chemical Formula 13]

[Formula 14]

[Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

The compound represented by the said General formula (1) can be synthesize | combined well-known reactions, such as a Suzuki coupling reaction. Moreover, it can synthesize | combine by the method as described in international publication 05/013388 brochure, international publication 06/130598 brochure, and international publication 09/021107 brochure.

After synthesis, purification by column chromatography, recrystallization or the like is preferably followed by purification by sublimation purification. By the sublimation purification, it is possible not only to separate organic impurities, but also to effectively remove inorganic salts and residual solvents.

The compound represented by General formula (1) may be contained in any organic layer between the cathode and the anode of an organic electroluminescent element. It is preferable that the compound represented by General formula (1) is contained in the light emitting layer or the organic layer between a light emitting layer and a cathode, and adjacent to a light emitting layer.

As an organic layer which may contain the compound represented by General formula (1), 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 layer (hole block layer, an electron block layer, etc.) etc. These may be mentioned, Preferably it is any of a light emitting layer, an exciton block layer, a charge block layer, an electron carrying layer, an electron injection layer, More preferably, it is a light emitting layer, an exciton block layer, a charge block layer, or an electron carrying layer, More preferably, Is a light emitting layer or a charge block layer.

When the compound represented by the general formula (1) is contained in the light emitting layer, it is preferable to contain 0.1 to 99 mass% with respect to the total mass of the light emitting layer, more preferably 1 to 95 mass%, more preferably 10 to 95 mass% It is more preferable to contain.

When the compound represented by General formula (1) is contained in organic layers other than a light emitting layer, it is preferable to contain 70-100 mass% with respect to the total mass of the organic layer, and it is more preferable to contain 85-100 mass%.

[Charge Transport Material Represented by General Formula (1)]

The present invention also relates to a charge transport material represented by the general formula (1).

The compound and charge transport material represented by the general formula (1) of the present invention can be suitably used for organic electronic devices such as electrophotographic, organic transistors, organic photoelectric conversion devices (energy conversion applications, sensor applications, etc.) and organic electroluminescent devices. It is possible to use it for an organic electroluminescent element, and it is especially preferable.

The range with preferable charge transport material represented by General formula (1) is as above-mentioned.

[Composition containing a compound represented by General Formula (1)]

This invention relates also to the composition containing the compound represented by General formula (1). In this composition, it is preferable that content of the compound represented by General formula (1) is 30-99 mass% with respect to the total solid in a composition, It is more preferable that it is 50-97 mass%, It is 70-96 mass% More preferred. As another component which may be contained in the composition of this invention, an organic substance may be sufficient and an inorganic substance may be sufficient, As the organic substance, the material illustrated as a host material mentioned below, a fluorescent light emitting material, a phosphorescent light emitting material, and a hydrocarbon material can be applied. And, preferably, a host material, a phosphorescent material and a hydrocarbon material.

The composition can form the organic layer of an organic electroluminescent element by dry film forming methods, such as a vapor deposition method and a sputtering method, and a wet film forming method, such as a transfer method and a printing method.

[Thin Film Containing Compound Represented by General Formula (1)]

This invention relates also to the thin film containing the compound represented by General formula (1). The thin film can be formed by a wet film forming method such as a dry film forming method such as a vapor deposition method or a sputtering method, a transfer method, or a printing method using the composition. The film thickness of the thin film may be any thickness depending on the application, 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.

[Organic electroluminescent device]

The organic electroluminescent element of this invention is demonstrated in detail.

An organic electroluminescent element of the present invention is an organic electroluminescent element having a pair of electrodes consisting of an anode and a cathode on a substrate, and at least one organic layer including a light emitting layer between the electrodes, wherein the organic electroluminescent element comprises At least 1 layer of an organic layer contains the compound represented by General formula (1) of this invention. It is preferable that at least one of the positive electrode and the negative electrode, which are a pair of electrodes, is transparent or semitransparent in nature of the light emitting element.

Examples of the organic layer include a hole injection layer, a hole transport layer, a block layer (hole block layer, exciton block layer, etc.), an electron transport layer, etc. in addition to the light emitting layer. Two or more layers of these organic layers may be formed, respectively, and when forming two or more layers, they may be formed with the same material, and may be formed with a different material for every layer.

It is preferable that the organic electroluminescent element of this invention contains at least 1 sort (s) of phosphorescence light emitting material in the said light emitting layer.

Fig. 1 shows an example of the structure of an organic electroluminescence device according to the present invention. The organic electroluminescent element 10 of FIG. 1 has on the board | substrate 2 the organic layer containing the light emitting layer 6 between a pair of electrode (anode 3 and cathode 9). A hole injecting layer 4, a hole transporting layer 5, a light emitting layer 6, a hole blocking layer 7 and an electron transporting layer 8 are laminated in this order from the side of the anode 3 as an organic layer.

<Organization of Organic Layer>

There is no restriction | limiting in particular as a laminated constitution of the said organic layer, Although it can select suitably according to the use and the objective of an organic electroluminescent element, What is formed on the said transparent electrode or the said semi-transparent electrode is preferable. In this case, the organic layer is formed on the front surface or one surface of the transparent electrode or the translucent electrode.

There is no restriction | limiting in particular about the shape, size, thickness, etc. of an organic layer, According to the objective, it can select suitably.

Although the following is mentioned as a specific laminated constitution, This invention is not limited to these constitutions.

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

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

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

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

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

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

The element structure of the organic electroluminescent element, the board | substrate, a cathode, and an anode are described in detail in Unexamined-Japanese-Patent No. 2008-270736, for example, and the matter of the publication can be applied to this invention.

<Substrate>

As a board | substrate used by this invention, it is preferable that it is a board | substrate which does not scatter or attenuate the light emitted from an organic layer. In the case of an organic material, it is preferable that it is excellent in heat resistance, dimensional stability, solvent resistance, electrical insulation, and processability.

<Anode>

The anode usually has a function as an electrode for supplying holes to the organic layer, and the shape, structure, size, and the like thereof are not particularly limited, and can be appropriately selected from known electrode materials according to the use and purpose of the light emitting device. As mentioned above, the anode is usually formed as a transparent anode.

<Cathode>

The cathode may have a function as an electrode which injects electrons into an organic layer normally, and there is no restriction | limiting in particular about the shape, a structure, a size, etc. According to the use and the objective of a light emitting element, it can select suitably from well-known electrode materials.

<Organic layer>

The organic layer in this invention is demonstrated.

(Formation of Organic Layer)

In the organic electroluminescent device of the present invention, each organic layer can be preferably formed by any one of dry coating methods such as vapor deposition and sputtering, solution coating such as transfer, printing, spin coating, and bar coating. have. It is preferable that at least 1 layer of an organic layer is formed by the solution coating method.

(Light emitting layer)

The light emitting layer has a function of receiving holes from an anode, a hole injection layer or a hole transporting layer when receiving an electric field, and receiving electrons from a cathode, an electron injection layer or an electron transporting layer to provide a hole and electron recombination site and emit light. to be. The light emitting layer in the organic electroluminescent device of the present invention preferably contains at least one phosphorescent material.

(Luminescent material)

As the light emitting material in the present invention, both phosphorescent light emitting materials, fluorescent light emitting materials and the like can be used.

The light emitting layer in this invention can contain two or more types of light emitting materials in order to improve color purity and to enlarge an emission wavelength area | 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, as the light emitting material, a phosphorescent light emitting material different from the phosphorescent light emitting material contained in the light emitting layer can be used.

For these fluorescent light emitting materials and phosphorescent light emitting materials, for example, paragraphs [0100] to [0164] of JP 2008-270736 A and paragraphs [0088] to [0090] of JP 2007-266458 The matters described in detail and described in these publications can be applied to the present invention.

Phosphorescent light emitting materials that can be used in the present invention include, for example, US 6303238B1, US 6097147, WO 00/57676, WO 00/70655, WO 01/08230, WO 01 / 39234A2, WO 01 / 41512A1, WO 02 / 02714A2, WO 02 / 15645A1, WO 02 / 44189A1, WO 05 / 19373A2, JP 2001-247859, JP 2002-302671, JP 2002-117978, JP 2003-133074, Japan JP 2002-235076, JP 2003-123982, JP 2002-170684, EP 1211257, JP 2002-226495, JP 2002-234894, JP 2001-247859, JP 2001-298470, JP 2002-173674, JP 2002-203678, JP 2002-203679, JP 2004-357791, JP 2006-256999, JP Patent documents such as Japanese Patent Application Publication No. 2007-19462, Japanese Patent Application Publication No. 2007-84635, Japanese Patent Application Publication No. 2007-96259 The phosphorescent compound described in the above may be mentioned, and among these, more preferable light emitting materials include Ir complex, Pt complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu complex, And phosphorescent metal complex compounds such as Tb complexes, Gd complexes, Dy complexes, and Ce complexes. Particularly preferred are Ir complexes, Pt complexes or Re complexes, among which Ir complexes containing at least one of a metal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond and a metal- Complex, or a Re complex is preferable. Moreover, Ir complex and Pt complex are especially preferable from a viewpoint of luminous efficiency, drive durability, chromaticity, etc., and Ir complex is the most preferable.

It is preferable to use the iridium complex represented by general formula (E-1) shown below, or the platinum complex represented by the following general formula (C-1) as a phosphorescence emitting material contained in the light emitting layer in this invention. .

General formula (E-1) is demonstrated.

[Chemical Formula 18]

In General Formula (E-1), Z ¹ and Z ² each independently represent a carbon atom or a nitrogen atom.

A ₁ represents a group of atoms that together with Z ¹ and a nitrogen atom form a heterocyclic ring of 5 or 6 atoms.

B ₁ represents an atomic group which forms a 5 or 6 membered ring together with Z ² and a carbon atom.

(X-Y) represents a monoanionic bidentate ligand.

_nE1 represents the integer of 1-3.

n _E1 represents the integer of 1-3, Preferably it is 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 a group of atoms that together with Z ¹ and a nitrogen atom form a heterocyclic ring of 5 or 6 atoms. Examples of the 5 or 6 membered heterocycle containing A ₁ , Z ¹ and a nitrogen atom include pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, Triazole ring, an oxadiazole ring, a thiadiazole ring, etc. are mentioned.

In view of stability of the complex, emission wavelength control and emission quantum yield, a 5 or 6 membered hetero ring formed of A ₁ , Z ¹ and a nitrogen atom is preferably a pyridine ring, a pyrazine ring, an imidazole ring, a pyrazole ring More preferably, they are a pyridine ring, an imidazole ring, and a pyrazine ring, More preferably, they are a pyridine ring, an imidazole ring, Most preferably, they are a pyridine ring.

The 5 or 6 membered hetero ring formed by A ₁ , Z ¹ and a nitrogen atom may have a substituent, and the substituent group A may be applied as a substituent on a carbon atom, and the substituent group B may be applied as a substituent on a nitrogen atom. Can be. As a substituent on carbon, Preferably, they are 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, and a fluorine atom.

Substituents are appropriately selected for the control of the emission wavelength or potential, but in the case of shortening, an electron donating group, a fluorine atom, an aromatic ring group is preferable, and an alkyl group, a dialkylamino group, an alkoxy group, a fluorine atom, an aryl group, an aromatic Heterocyclic groups and the like. Moreover, when making it long-wavelength, an electron withdrawing group is preferable, for example, a cyano group, a perfluoroalkyl group, etc. are selected.

As a substituent on nitrogen, Preferably, they are an alkyl group, an aryl group, and an aromatic heterocyclic group, and an alkyl group and an aryl group are preferable from a viewpoint of stability of a complex.

The substituents may be connected to each other to form a condensed ring, and as the ring formed, a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, a pyrazole And ring, thiophene ring, and furango ring. The ring formed may have a substituent and the substituent on the carbon atom mentioned above and the substituent on a nitrogen atom are mentioned as a substituent.

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 of B ₁ , Z ² and carbon atoms include benzene ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, Thiazole ring, triazole ring, oxadiazole ring, thiadiazole ring, thiophene ring, furan ring and the like.

As a 5 or 6 membered ring formed from B ₁ , Z ² and carbon atoms in terms of stability of the complex, emission wavelength control and emission quantum yield, preferably, a benzene ring, a pyridine ring, a pyrazine ring, an imidazole ring, a pyrazole ring And thiophene ring, More preferably, they are a benzene ring, a pyridine ring, a pyrazole ring, More preferably, they are a benzene ring and a pyridine ring.

The 5 or 6 membered ring formed of said B <_1> , Z <^2> and a carbon atom may have a substituent, The said substituent group B is applicable as a substituent on a carbon atom, and the said substituent group B is applicable as a substituent on a nitrogen atom. . As a substituent on carbon, Preferably, they are 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, and a fluorine atom.

Substituents are appropriately selected for controlling the emission wavelength or potential, but in the case of making a long wavelength, an electron donating group and an aromatic ring group are preferable, and for example, an alkyl group, a dialkylamino group, an alkoxy group, an aryl group, an aromatic heterocyclic group, or the like is selected. do. In addition, when shortening, an electron withdrawing group is preferable, for example, a fluorine atom, a cyano group, a perfluoroalkyl group, etc. are selected.

As a substituent on nitrogen, Preferably, they are an alkyl group, an aryl group, and an aromatic heterocyclic group, and an alkyl group and an aryl group are preferable from a viewpoint of stability of a complex. The substituents may be connected to each other to form a condensed ring, and as the ring formed, a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, a pyrazole And ring, thiophene ring, and furango ring. The ring formed may have a substituent and the substituent on the carbon atom mentioned above and the substituent on a nitrogen atom are mentioned as a substituent.

In addition, a substituent of a 5 or 6 membered heterocyclic ring formed of A ₁ , Z ¹ and a nitrogen atom and a substituent of a 5 or 6 membered ring formed of B ₁ , Z ² and a carbon atom are connected to each other, the same condensed ring as described above May be formed.

As the ligand represented by (XY), there are various known ligands used in conventionally known metal complexes. For example, `` Photochemistry and Photophysics of Coordination Compounds '' by Springer-Verlag, H.Yersin, published in 1987, "Organic Metal Chemistry-Foundations and Applications-Shokabo Publishing Co., Ltd. Yamamoto Akio Published in 1982, etc. Ligands (e.g., halogen ligands (preferably chlorine ligands), nitrogen-containing heteroaryl ligands (e.g., bipyridyl, phenan) And diketone ligands (for example, acetylacetone, etc.) As the ligand represented by (XY), diketones or picolinic acid derivatives are preferable, and stability of complexes and high luminous efficiency are shown. It is most preferable that it is acetylacetonate (acac) shown below from the viewpoint which is obtained.

[Chemical Formula 19]

* Indicates a coordination position relative to iridium.

As a ligand represented by (X-Y), the following general formulas (I-1) to (I-14) are preferable, but the present invention is not limited to these.

[Chemical Formula 20]

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

When Rx, Ry, and Rz represent a substituent, the substituent selected from the said substituent group A is mentioned. Preferably, Rx and Rz are each independently an alkyl group, a perfluoroalkyl group, a fluorine atom or an aryl group, and more preferably an alkyl group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, or a fluorine atom And a phenyl group which may be substituted, and most preferably, they are a methyl group, an ethyl group, a trifluoromethyl group, a fluorine atom, and a phenyl group. Ry is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, a fluorine atom, or an aryl group, more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group which may be substituted, and most preferably hydrogen It is either an atom or a methyl group. Since these ligands are not considered to be sites where electrons are concentrated by the charge transport or excitation in the device, Rx, Ry, and Rz may be chemically stable substituents, and do not affect the effect of the present invention.

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

[Chemical Formula 21]

R ^I1 to R ^I4 in General Formula (I-15) represent a substituent selected from Substituent Group A, and B represents CR or a nitrogen atom. R represents a substituent selected from substituent group A. R ^I5 to R ^I7 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, -CN, a perfluoroalkyl group, a trifluorovinyl group, -CO ₂ R, -C (O) R,- NR _2, -NO _2, -OR, halogen atom, an aryl group or a heteroaryl group, and may have a substituent a. R each 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 with respect to iridium in general formula (E-1).

Any two 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 condensation 4 The 7-membered ring may further have a substituent Z.

Z are each 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 '', and R '' Each 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.

The preferable ranges of R ^I1 to R ^I7 are the same as the preferable ranges of R ^T1 to R ^T7 in General Formula (E-3) described later. Preferably it is CR, It is CR, Preferably it is an aryl group, More preferably, it is a C6-C30 substituted or unsubstituted aryl group (for example, a phenyl group, a tolyl group, a naphthyl group, etc.), Especially Preferably it is a phenyl group.

As (X-Y), More preferably, they are (I-1), (I-4), (I-15), Especially preferably, they are (I-1) and (I-15). Complexes having these ligands can be synthesized in the same manner as known synthesis examples by using the corresponding ligand precursor. For example, it can synthesize | combine by the method shown below using difluoroacetyl acetone commercially similarly to the method of international publication 2009-073245.

A preferable aspect of the Ir complex represented by General Formula (E-1) is an Ir complex represented by General Formula (E-2).

[Chemical Formula 22]

In General Formula (E-2), A ^E1 to A ^E8 each independently represent a nitrogen atom or CR ^E.

R ^E represents a hydrogen atom or a substituent.

(X-Y) represents a monoanionic bidentate ligand.

_nE2 represents the integer of 1-3.

A ^E1 to A ^E8 each independently represent a nitrogen atom or CR ^E. R ^E represents a hydrogen atom or a substituent, and R ^E may be connected to each other to form a ring. As a ring formed, the thing similar to the condensed ring mentioned in general formula (E-1) mentioned above is mentioned. As a substituent represented by R <^E> , what was illustrated as said substituent group A is applicable.

When A ^E1 to A ^E4 are preferably CR ^E , and when A ^E1 to A ^E4 are CR ^E , preferably R ^E of A ^E3 is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, or 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, A ^E1 , A ^E2 and R ^E of 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, and more preferably a hydrogen atom, an alkyl group, an amino group, an alkoxy group or an aryl octane. It is a time period or a fluorine atom, Especially preferably, it is a hydrogen atom.

A and ^E5 ~ A ^E8 preferably CR ^E a, A ^E5 ~ A ^E8 is CR in case of ^E, preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group as R ^E, D It is an alkylamino group, a diarylamino group, an alkyloxy group, a cyano group, or a fluorine atom, More preferably, it is a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, a dialkylamino group, a cyano group, or a fluorine atom, More preferably Preferably it is a hydrogen atom, an alkyl group, a trifluoromethyl group, or a fluorine atom. If possible, substituents may be linked to each other to form a condensed structure. When shifting the emission wavelength toward the short wavelength side, it is preferable that A ^E6 is a nitrogen atom.

(XY) and n _E2 are synonymous with (XY) and n _E1 in general formula (E-1), and its preferable range is also the same.

The more preferable aspect of the compound represented by said general formula (E-2) is a compound represented with the following general formula (E-3).

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In general formula (E-3), R ^T1 , R ^T2 , R ^T3 , R ^T4 , R ^T5 , R ^T6 and R ^T7 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, -CN, A perfluoroalkyl group, a trifluorovinyl group, -CO ₂ R, -C (O) R, -NR ₂ , -NO ₂ , -OR, a halogen atom, an aryl group or a heteroaryl group, and further a substituent Z You may have it. R each 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, and may further have a substituent Z. R each 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 ^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 a cycloalkane, an aromatic hydrocarbon or an aromatic heterocycle, and the condensation 4 The 7-membered ring may further have a substituent Z. Among them, a case that is chukhwan by R ^T1 and R ^{T7, T5,} or R and R ^T6 form a benzene ring are preferred, and are chukhwan by R and R ^{T5 T6} is particularly preferable in the case of forming a benzene ring.

Substituents Z are each 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'', and R''Each 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.

(XY) represents a monoanionic bidentate ligand. _nE3 represents the integer of 1-3.

Examples of the alkyl group which may have a substituent, may be saturated or unsaturated, and may be substituted, the substituent Z described above. 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, and more preferably an alkyl group having 1 to 6 carbon atoms in total, for example, a methyl group, an ethyl group, or i- A propyl group, a cyclohexyl group, t-butyl group, etc. are mentioned.

The cycloalkyl group may have a substituent, may be saturated or unsaturated, or may be substituted with the substituent Z described above. The cycloalkyl group represented by R ^T1 to R ^T7 and R 'is preferably a cycloalkyl group having 4 to 7 ring atoms, more preferably a cycloalkyl group having 5 to 6 carbon atoms, for example, a cyclopentyl group, Cyclohexyl group etc. are mentioned, A methyl group is especially preferable.

The alkenyl group represented by R ^T1 to R ^T7 and R 'is preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, for example vinyl, allyl, 1-. Propenyl, 1-isopropenyl, 1-butenyl, 2-butenyl, 3-pentenyl and the like.

As an alkynyl group represented by R <^T1> -R <^T7> and R ', Preferably it is C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2-C10, 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 substituted 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, and a phenyl group is particularly preferable. .

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 substituted or unsubstituted heteroaryl group having 5 or 6 atoms, for example, Dill 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 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, benzisooxazolyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, imidazolidinyl group, thia Zolinyl group, sulfolanyl group, carbazolyl group, dibenzofuryl group, di Crude thienyl group, and the like based degrees turned 7 flutes. Preferable examples are pyridyl group, pyrimidinyl group, imidazolyl group and thienyl group, and more preferably 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, and a heteroaryl group, more preferably. Is a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a fluoro group, an aryl group, More preferably, they are 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 is more preferable.

Any two of R ^T1 to R ^T7 and R 'may be bonded to each other to form a condensed 4 to 7 membered ring, and the condensed 4 to 7 membered ring is a cycloalkane, an aromatic hydrocarbon or an aromatic heterocycle, and the condensation 4 to The 7-membered ring may further have a substituent Z. The definition and preferable ranges of the cycloalkane, aromatic hydrocarbon, and aromatic heterocyclic ring to be formed are cycloalkane, aromatic hydrocarbon, and aromatic compound in which one hydrogen atom is added to the cycloalkyl group, aryl group, and heteroaryl group in R ^T1 to R ^T7 and R '. Heterocycle can be mentioned.

In addition, A is CR 'with represents a, R ^T1 ~ R ^T7 and R' of from 0 to two are each an alkyl group or a phenyl group, are particularly preferred if the remainder is a hydrogen atom, R ^T1 ~ R ^T7 and R ', 0 - and the two are alkyl groups, and the other is all preferable, and particularly, R ^T1-T7 R and R 'of 0-2 dogs methyl group a hydrogen atom is most preferred if the remainder is a hydrogen atom.

It is preferable that n _E3 is 2 or 3. It is preferable that the kind of ligand in a complex is comprised from 1-2 types, More preferably, it is one type. When introducing a reactive group into a complex molecule, it is also preferable that a ligand consists of two types from a viewpoint of the ease of synthesis.

(X-Y) is synonymous with (X-Y) in General formula (E-1), and its preferable range is also the same.

One of the preferable forms of the compound represented by said general formula (E-3) is a compound represented with the following general formula (E-4).

&Lt; EMI ID =

R ^T1 to R ^T4 , A, (XY) and n _E4 in General Formula (E-4) are R ^T1 to R ^T4 , A, (XY) and n _{E3 in} General Formula (E-3). It is synonymous with and a preferable range is also the same. R ₁ 'to R ₅ ' are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, a trifluorovinyl group, -CO ₂ R, -C (O) R , -NR ₂ , -NO ₂ , -OR, a halogen atom, an aryl group or a heteroaryl group, may further have a substituent Z. R each 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 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 a cycloalkane, an aromatic hydrocarbon or an aromatic heterocycle, and the condensed 4 to 7 The atomic ring may further have a substituent Z.

Z are each 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 '', and R '' Each 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.

In addition, the preferable range in R <_1> -R <_5>'is the same as that of R <^T1> -R <^T7> , R' in general formula (E-3). In addition, A is, together with represents a, R ^T1 ~ R ^T4, R, CR, and R ₁ '~ R _5' from 0 to two are each an alkyl group or a phenyl group is particularly preferred if the remainder is a hydrogen atom, and R ^T1 ~ R ^T4, R ', and R _1' ~ R ₅ 'of 0-2 dogs alkyl group is more preferred if the remainder is a hydrogen atom.

Another preferable form of the compound represented by said general formula (E-3) is a compound represented with the following general formula (E-5).

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In the formula ^{(E5) R T2 ~ R T6} , A, (XY) n and _E5 are, ^T2 ~ R in the formula ^{(E3) R T6, A,} (XY) n and _E3 It is synonymous with, and a preferable range is also the same. R ₆ 'to R ₈ ' are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, a trifluorovinyl group, -CO ₂ R, -C (O) R , -NR ₂ , -NO ₂ , -OR, a halogen atom, an aryl group or a heteroaryl group, may further have a substituent Z. R each 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 ^T5 , R ^T6 and R ₆ 'to R ₈ ' 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 cycloalkane, an aromatic hydrocarbon or an aromatic heterocycle. The condensed 4 to 7 membered ring may further have a substituent Z.

Z are each 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 '', and R '' Each 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.

In addition, the preferable range in R <_6>'-R<_8>' is the same as that of R <^T1> -R <^T7> , R 'in general formula (E-3). In addition, A is, together with represents a, R ^T2 ~ R ^T6, R, CR, and R ₆ '~ R _8' of 0 to two are each an alkyl group or a phenyl group is particularly preferred if the remainder is a hydrogen atom, and R ^T2 ~ R ^T6, R ', and R _6' ~ R ₈ 'of 0-2 dogs alkyl group is more preferred if the remainder is a hydrogen atom.

When using the phosphorescent light emitting material represented by general formula (E-4) or (E-5), it is preferable that the compound represented by general formula (1) is contained in a light emitting layer or a hole block layer, and it is contained in a light emitting layer More preferred.

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

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In General Formula (E-6), R _1a to R _1k are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, a trifluorovinyl group, and -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. R each 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 a cycloalkane, an aromatic hydrocarbon or an aromatic heterocycle, and the condensed 4 to 7 membered ring May further have a substituent Z.

Z are each 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 '', and R '' Each 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.

(X-Y) represents a monoanionic bidentate ligand.

_nE6 represents the integer of 1-3.

In general formula (E-6), the preferable range of R <_1a> -R <_1k> is the same as that of R <^T1> -R <^T7> , R 'in general formula (E-3). Moreover, especially when 0-2 of R <_1a> -R <_1k> is an alkyl group or a phenyl group, and all remainder are hydrogen atoms, it is especially preferable when 0-2 of R <_1a> -R <_1k> are alkyl groups, and all others are hydrogen atoms. .

It is especially preferable when _R1j and _R1k are connected to form a single bond.

Preferable ranges of (XY) and n _E6 are the same as (XY) and n _E3 in General formula (E-3).

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

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In General Formula (E-7), R _1a to R _1i are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, a trifluorovinyl group, and -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. R each 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 a cycloalkane, an aromatic hydrocarbon or an aromatic heterocycle, and the condensed 4 to 7 membered ring May further have a substituent Z.

Z are each 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 '', and R '' Each 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.

(X-Y) represents a monoanionic bidentate ligand.

_nE7 represents the integer of 1-3.

In the general formula (E-7), defined and preferred ranges of R _1a ~ R _1i is the same as R _1a ~ R _1i in the formula (E-6). Moreover, especially when 0-2 of R <_1a> -R <_1i> are an alkyl group or an aryl group, and all remainder are hydrogen atoms, it is especially preferable.

The definition and the preferred range of (XY) and n _E7 are the same as those of (XY) and n _E3 in General Formula (E-3).

When using the phosphorescence emitting material represented by general formula (E-6) or (E-7), it is preferable that the compound represented by general formula (1) is contained in a light emitting layer or a hole block layer.

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

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[Formula 29]

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The compound illustrated as a compound represented by said general formula (E-1) can be synthesize | combined by the method of Unexamined-Japanese-Patent No. 2009-99783, the various methods of US Pat. After synthesis, purification by column chromatography, recrystallization or the like is preferably followed by purification by sublimation purification. By the sublimation purification, it is possible not only to separate organic impurities, but also to effectively remove inorganic salts and residual solvents.

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 be further contained in any layer in an organic layer.

Although the compound represented by general formula (E-1) in a light emitting layer is contained 0.1 mass%-50 mass% with respect to the mass of all the compounds which form a light emitting layer generally in a light emitting layer, 1 mass%-50 from a viewpoint of durability and an external quantum efficiency. It is preferable to contain mass%, and it is more preferable to contain 2 mass%-40 mass%.

As a platinum complex which can be used as a phosphorescence emitting material, Preferably it is a platinum complex represented by following General formula (C-1).

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(Wherein, Q ¹ , Q ² , Q ³ and Q ⁴ each independently represent a ligand that coordinates to Pt. L ¹ , L ² and L ³ each independently represent a single bond or a divalent linking group)

General formula (C-1) is demonstrated. Q ¹ , Q ² , Q ³ and Q ⁴ each independently represent a ligand that coordinates to Pt. At this time, any one of Q ¹ , Q ² , Q ^3, and Q ⁴ and Pt may be a covalent bond, an ionic bond, a coordination bond, or the like. As an atom which couple | bonds with Pt in Q <^1> , Q <^2> , Q <^3> and Q <^4> , a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a phosphorus atom are preferable, and it couple | bonds with Pt in Q <^1> , Q <^2> , Q <^3> and Q <^4> . It is preferable that at least 1 is a carbon atom, it is more preferable that 2 is a carbon atom, it is especially preferable that 2 is a carbon atom and 2 is a nitrogen atom among the atoms to make.

As Q ¹ , Q ² , Q ³ and Q ^{4, which} are carbon atoms and bonded to Pt, they may be anionic ligands or neutral ligands. Anionic ligands may be vinyl ligands or aromatic hydrocarbon ring ligands (e.g., benzene Ligands, naphthalene ligands, anthracene ligands, phenanthrene ligands, etc., heterocyclic ligands (e.g. furan ligands, thiophene ligands, pyridine ligands, pyrazine ligands, pyrimidine ligands, pyridazine ligands, triazine ligands, thiazole ligands, Oxazole ligands, pyrrole ligands, imidazole ligands, pyrazole ligands, triazole ligands and condensates containing them (for example, quinoline ligands, benzothiazole ligands, etc.). Neutral ligands include carbene ligands.

As the nitrogen atom and Q ¹ , Q ² , Q ³ and Q ⁴ bonded to Pt, it may be a neutral ligand or an anionic ligand, and the neutral ligand may be a nitrogen-containing aromatic heterocyclic ligand (pyridine ligand, pyrazine ligand, Pyrimidine ligands, pyridazine ligands, triazine ligands, imidazole ligands, pyrazole ligands, triazole ligands, oxazole ligands, thiazole ligands and condensates containing them (e.g. quinoline ligands, benzoimidazole ligands, etc.) ), An amine ligand, a nitrile ligand, and an imine ligand. Anionic ligands include amino ligands, imino ligands, nitrogen-containing aromatic heterocyclic ligands (pyrrole ligands, imidazole ligands, triazole ligands and condensers containing them (e.g. indole ligands, benzimidazole ligands, etc.) ).

Q ¹ , Q ² , Q ^3, and Q ^{4, which} are oxygen atoms and may bind to Pt, may be neutral or anionic ligands, and neutral ligands may include ether ligands, ketone ligands, ester ligands, amide ligands, An oxygen heterocyclic ligand (furan ligand, an oxazole ligand, and a condensate containing them (benzoxazole ligand etc.)) are mentioned. Examples of the anionic ligands include alkoxy ligands, aryloxy ligands, heteroaryloxy ligands, acyloxy ligands, silyloxy ligands, and the like.

As Q ¹ , Q ² , Q ^3, and Q ⁴ bonded to Pt as a sulfur atom, they may be neutral ligands or anionic ligands, and as neutral ligands, thioether ligands, thioketone ligands, thioester ligands, and thio Amide ligands, sulfur-containing heterocyclic ligands (thiophene ligands, thiazole ligands and condensates containing them (benzothiazole ligands, etc.)). Examples of the anionic ligands include alkyl mercapto ligands, aryl mercapto ligands, heteroaryl mercapto ligands, and the like.

As Q ¹ , Q ² , Q ³ and Q ^{4 which} are phosphorus atoms and which are bonded to Pt, they may be neutral ligands or anionic ligands, and the neutral ligands may be phosphine ligands, phosphate ester ligands, phosphite ester ligands, and phosphorus phosphorus. Heterocyclic ligands (phosphinine ligand etc.) are mentioned, As anionic ligand, a phosphino ligand, a phosphinyl ligand, a phosphoryl ligand, etc. are mentioned.

The group represented by Q <^1> , Q <^2> , Q <^3> and Q <^4> may have a substituent, and what was illustrated as said substituent group A as a substituent is applicable suitably. Substituents may also be connected (when Q <^3> and Q <^4> are connected, it becomes a Pt complex of a cyclic 4 left ligand).

The group represented by Q ¹ , Q ² , Q ³ and Q ⁴ is preferably an aromatic hydrocarbon ring ligand which is a carbon atom and is bonded to Pt, an aromatic heterocyclic ligand which is a carbon atom and is bonded to Pt, and is a nitrogen atom and is bonded to Pt Nitrogen-containing aromatic heterocyclic ligands, acyloxy ligands, alkyloxy ligands, aryloxy ligands, heteroaryloxy ligands, silyloxy ligands, more preferably aromatic hydrocarbon ring ligands that are carbon atoms and bind to Pt, carbon atoms, and An aromatic heterocyclic ligand to be bonded, a nitrogen atom and a nitrogen-containing aromatic heterocyclic ligand to be bonded to Pt, an acyloxy ligand, an aryloxy ligand, more preferably an aromatic hydrocarbon ring ligand to be bonded to Pt, a carbon atom and Pt Aromatic heterocyclic ligand bound to, nitrogen atom, bound to Pt Nitrogen aromatic heterocyclic ligands and acyloxy ligands.

L ¹ , L ² and L ³ represent a single bond or a divalent linking group. As the divalent linking group represented by L ¹ , L ^2, and L ³ , an alkylene group (methylene, ethylene, propylene, etc.), an arylene group (phenylene, naphthalenediyl), a heteroarylene group (pyridindiyl, thiophendiyl, etc.), or already Nogi (-NR-) (phenylimino group, etc.), oxy group (-O-), thiogi (-S-), phosphinidene group (-PR-) (phenylphosphinidene group, etc.), silylene group (-SiRR '-) (Dimethylsilylene group, diphenylsilylene group, etc.) or the combination thereof is mentioned. Here, as R and R ', an alkyl group, an aryl group, etc. are respectively independently mentioned. These linking groups may also have a substituent.

From the viewpoint of the stability of the complex and the luminescence 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, a silylene group, and more. Preferably they are a single bond, an alkylene group, an arylene group, and an imino group, More preferably, they are a single bond, an alkylene group, an arylene group, More preferably, they are a single bond, a methylene group, a phenylene group, More preferably, a single bond And a di-substituted methylene group, more preferably a single bond, a dimethyl methylene group, a diethyl methylene group, a diisobutyl methylene group, a dibenzyl methylene group, an ethyl methylene methylene group, a methyl propyl methylene group, an isobutyl methylene methylene group , Diphenylmethylene group, methylphenylmethylene group, cyclohexanediyl group, cyclopentanediyl group, fluorenediyl group, and fluoromethylene methylene group.

L ¹ is particularly preferably a dimethylmethylene group, a diphenylmethylene group or a cyclohexanediyl group, and most preferably a dimethylmethylene group.

Most preferably, it is a single bond as L <^2> and L <^3> .

Among the platinum complexes represented by General Formula (C-1), more preferably, they are platinum complexes represented by the following General Formula (C-2).

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

General formula (C-2) is demonstrated. L <^21> is synonymous with L <^1> in the said general formula (C-1), and its preferable range is also the same.

A ²¹ and A ²² each independently represent a carbon atom or a nitrogen atom. At least one of A ²¹ and A ²² is preferably a carbon atom, and A ²¹ and A ²² are preferably both carbon atoms from the viewpoint of the stability of the complex and the light emission quantum yield 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, a pyrimidine ring, a pyrazine ring, a triazine ring, an imidazole ring, a pyrazole ring, an oxazole ring, a thiazole ring, a triazole ring, and an oxiadia. Sol rings, thiadiazole rings, and the like. From the viewpoint of stability of the complex, emission wavelength control and emission quantum yield, the ring represented by Z ²¹ , Z ²² is preferably a pyridine ring, a pyrazine ring, an imidazole ring, a pyrazole ring, and more preferably a pyridine ring, It is an imidazole ring and a pyrazole ring, More preferably, it is a pyridine ring and a pyrazole ring, Especially preferably, it is a pyridine ring.

The nitrogen-containing aromatic heterocycle represented by Z ²¹ and Z ²² may have a substituent, and the substituent group B may be applied as the substituent group A as a substituent on a carbon atom and the substituent group B as a substituent on a nitrogen atom. As a substituent on a carbon atom, Preferably, they are 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, and a fluorine atom. Substituents are appropriately selected for the control of the emission wavelength or potential, but in the case of shortening, an electron donating group, a fluorine atom, an aromatic ring group is preferable, and an alkyl group, a dialkylamino group, an alkoxy group, a fluorine atom, an aryl group, an aromatic Heterocyclic groups and the like. Moreover, when making it long-wavelength, an electron withdrawing group is preferable, for example, a cyano group, a perfluoroalkyl group, etc. are selected. As a substituent on a nitrogen atom, Preferably, they are an alkyl group, an aryl group, and an aromatic heterocyclic group, and an alkyl group and an aryl group are preferable from a stability viewpoint of a complex. The substituents may be connected to each other to form a condensed ring, and the ring formed may include a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, a pyrazole ring , Thiophene ring, furango ring and the like.

Z ²³ and Z ²⁴ each independently represent a benzene ring or an aromatic hetero ring. Examples of the nitrogen-containing aromatic heterocycle represented by Z ²³ and Z ²⁴ include pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring and triazole. A ring, an oxadiazole ring, a thiadiazole ring, a thiophene ring, a furango ring, etc. are mentioned. As a ring represented by Z ²³ and Z ²⁴ from the viewpoint of stability of the complex, emission wavelength control and emission quantum yield, preferably, a benzene ring, a pyridine ring, a pyrazine ring, an imidazole ring, a pyrazole ring or a thiophene ring Preferably they are a benzene ring, a pyridine ring and a pyrazole ring, More preferably, they are a benzene ring and a pyridine ring.

The benzene ring and the nitrogen-containing aromatic heterocycle represented by Z ²³ and Z ²⁴ may have a substituent, and the substituent group B may be applied to the substituent group A as a substituent on a carbon atom and the substituent group B as a substituent on a nitrogen atom. . As a substituent on carbon, Preferably, they are 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, and a fluorine atom. Substituents are appropriately selected for controlling the emission wavelength or potential, but in the case of making a long wavelength, an electron donating group and an aromatic ring group are preferable, and for example, an alkyl group, a dialkylamino group, an alkoxy group, an aryl group, an aromatic heterocyclic group, or the like is selected. do. In addition, when shortening, an electron withdrawing group is preferable, for example, a fluorine atom, a cyano group, a perfluoroalkyl group, etc. are selected. As a substituent on a nitrogen atom, Preferably, they are an alkyl group, an aryl group, and an aromatic heterocyclic group, and an alkyl group and an aryl group are preferable from a stability viewpoint of a complex. The substituents may be connected to each other to form a condensed ring, and the ring formed may include a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, a pyrazole ring , Thiophene ring, furango ring and the like.

One of the more preferable aspects among the platinum complexes represented by general formula (C-2) is a platinum complex represented by the following general formula (C-4).

(33)

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

General formula (C-4) is demonstrated.

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

As a substituent represented by R, the thing illustrated as said substituent group A is applicable.

It is preferably CR as A ⁴⁰¹ to A ⁴⁰⁶ , and R may be connected to each other to form a ring. In the case where A ⁴⁰¹ to A ⁴⁰⁶ are CR, R ⁴⁰² and A ⁴⁰⁵ are preferably hydrogen atoms, alkyl groups, aryl groups, amino groups, alkoxy groups, aryloxy groups, fluorine atoms, and cyano groups, and more preferably. It is a hydrogen atom, an amino group, an alkoxy group, an aryloxy group, and a fluorine atom, Especially preferably, they are a hydrogen atom and a fluorine atom. R of A ⁴⁰¹ , A ⁴⁰³ , A ⁴⁰⁴ , 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, a cyano group, and more preferably a hydrogen atom, an amino group, It is an alkoxy group, an aryloxy group, and a fluorine atom, Especially preferably, it is a hydrogen atom.

L ⁴¹ has the same meaning as L ¹ in General Formula (C-1), and the preferred range thereof is also the same.

As A ⁴⁰⁷ -A ^{414, in} each of A ⁴⁰⁷ -A ⁴¹⁰ and A ⁴¹¹ -A ⁴¹⁴ , the number of N (nitrogen atoms) is preferably 0 to 2, and more preferably 0 to 1. In the case where the emission wavelength is shifted to the shorter wavelength side, either A ⁴⁰⁸ or A ⁴¹² is preferably a nitrogen atom, and more preferably A ⁴⁰⁸ and A ⁴¹² are a nitrogen atom together.

When A ⁴⁰⁷ to A ⁴¹⁴ represent CR, R ⁴⁰⁸ and R ⁴¹² are preferably hydrogen atoms, alkyl groups, perfluoroalkyl groups, aryl groups, amino groups, alkoxy groups, aryloxy groups, fluorine atoms, and cyano groups. More preferably, they are a hydrogen atom, a perfluoroalkyl group, an alkyl group, an aryl group, a fluorine atom, and a cyano group, Especially preferably, they are a hydrogen atom, a phenyl group, a perfluoroalkyl group, and 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, and more preferably It is a hydrogen atom, a perfluoroalkyl group, a fluorine atom, and a cyano group, Especially preferably, they are a hydrogen atom, a phenyl group, and a fluorine atom. R of A ⁴¹⁰ and A ⁴¹⁴ is preferably a hydrogen atom or a fluorine atom, and more preferably a hydrogen atom. When any of A ⁴⁰⁷ to A ⁴⁰⁹ and A ⁴¹¹ to A ⁴¹³ represents CR, R may be connected to each other to form a ring.

Among the platinum complexes represented by General Formula (C-2), one of more preferred embodiments is a platinum complex represented by the following General Formula (C-5).

(34)

(In General Formula (C-5), A ⁵⁰¹ to A ⁵¹² each independently represent CR or a nitrogen atom. R represents a hydrogen atom or a substituent. L ⁵¹ represents a single bond or a divalent linking 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 the preferred range thereof is also the same.

A ⁵⁰⁷ , A ⁵⁰⁸ and A ⁵⁰⁹ and A ⁵¹⁰ , A ⁵¹¹ and A ⁵¹² each independently represent a CR or nitrogen atom. R represents a hydrogen atom or a substituent. As a substituent represented by R, the thing illustrated as said substituent group A is applicable. When A ⁵⁰⁷ , A ⁵⁰⁸ and A ⁵⁰⁹ and A ⁵¹⁰ , A ⁵¹¹ and A ⁵¹² are CR, R is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, It is a diarylamino group, an alkyloxy group, a cyano group, and a fluorine atom, More preferably, a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, a dialkylamino group, a cyano group, a fluorine atom, More preferably, a hydrogen atom and an alkyl group , Trifluoromethyl group and fluorine atom. If possible, substituents may be linked to each other to form a condensed 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, particularly preferably A ⁵¹⁰ or A ⁵⁰⁷ is a nitrogen atom.

Among the platinum complexes represented by General Formula (C-1), another more preferred embodiment is a platinum complex represented by the following General Formula (C-6).

(35)

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

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

A ⁶¹ represents a carbon atom or a nitrogen atom. It is preferable that A ⁶¹ is a carbon atom from a viewpoint of the stability of a complex, and the light emission quantum yield of a complex.

Z <^61> , Z <^62> is synonymous with Z <^21> and Z <^{22> in the} said general formula (C-2), respectively, and its preferable range is also the same. Z ⁶³ has the same meaning as Z ²³ in General Formula (C-2), and the preferred range thereof is also the same.

Y is an anionic acyclic ligand that binds to Pt. Acyclic ligands are those in which atoms bonded to Pt do not form a ring in the ligand state. 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.

Y as a carbon atom and bonded to Pt includes a vinyl ligand. As a nitrogen atom and Y couple | bonded with Pt, an amino ligand and an imino ligand are mentioned. Examples of Y bonded to Pt as an oxygen atom include alkoxy ligands, aryloxy ligands, heteroaryloxy ligands, acyloxy ligands, silyloxy ligands, carboxyl ligands, phosphoric acid ligands, sulfonic acid ligands and the like. Examples of Y bonded to Pt as a sulfur atom include alkyl mercapto ligands, aryl mercapto ligands, heteroaryl mercapto ligands, and thiocarboxylic acid ligands.

The ligand represented by Y may have a substituent and the thing illustrated as said substituent group A can be suitably applied as a substituent. Substituents may also be connected.

The ligand represented by Y is preferably an oxygen atom and a ligand that binds to Pt, more preferably an acyloxy ligand, an alkyloxy ligand, an aryloxy ligand, a heteroaryloxy ligand and a silyloxy ligand, still more preferably an acyloxy I'm a traitor.

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

(36)

(Wherein, A ⁷⁰¹ to A ⁷¹⁰ each independently represent CR or a nitrogen atom. R represents a hydrogen atom or a substituent. L ⁷¹ represents a single bond or a divalent linking group. Y represents an anionic bond to Pt. Acyclic ligand)

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

As a platinum complex represented by general formula (C-1), the compound as described in [0143]-[0152], [0157]-[0158], [0162]-[0168] of Unexamined-Japanese-Patent No. 2005-310733 specifically, , The compounds described in [0065] to [0083] of JP 2006-256999 A, the compounds described in [0065] to [0090] of JP 2006-93542 A, and the compounds of JP 2007-73891 A The compound described in [0071], The compound described in [0079] to [0083] of JP 2007-324309, The compound described in [0065] to [0090] of JP 2006-93542, JP The compound described in 2007-96255 [0055]-[0071], and [0043]-[0046] of Unexamined-Japanese-Patent No. 2006-313796 are mentioned, The platinum complex illustrated below is mentioned.

[Formula 37]

(38)

[Chemical Formula 39]

The platinum complex compound represented by General Formula (C-1) is, for example, the method described in page 789, left column 53 to right column 7, of Journal of Organic Chemistry 53, 786, (1988), GR Newkome et al. Page 790, left column 18-38, method 790, page 19-30, and combinations thereof, Chemische Berichte 113, 2749 (1980), H. Lexy et al.), Page 2752, line 26- It can synthesize | combine by various methods, such as the method of row 35.

For example, the ligand, or the dissociation agent and the metal compound thereof may be 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, and a sulfone type). Solvents, sulfoxide solvents, water, etc.) or in the absence of a solvent, in the presence of a base (inorganic, various organic bases such as sodium methoxide, t-butoxy potassium, triethyl Amine, potassium carbonate, and the like), or in the absence of a base, can be obtained at room temperature or lower, or by heating (a method of heating by microwave in addition to normal heating is also effective).

It is preferable that content of the compound represented by general formula (C-1) in the light emitting layer of this invention is 1-30 mass% in a light emitting layer, It is more preferable that it is 3-25 mass%, It is 5-20 mass% More preferred.

Although the kind of said fluorescent light emitting material is not specifically limited, For example, benzoxazole, benzoimidazole, benzothiazole, styrylbenzene, polyphenyl, diphenylbutadiene, tetraphenylbutadiene, naphthalimide, coumarin, Pyran, perinone, oxadiazole, aldazine, pyralizine, cyclopentadiene, bisstyrylanthracene, quinacridone, pyrrolopyridine, thiadiazolopyridine, cyclopentadiene, styrylamine, condensed polycyclic aromatic Compounds (such as anthracene, phenanthroline, pyrene, perylene, rubrene, or pentacene), metal complexes of 8-quinolinol, various metal complexes represented by pyrimethene complexes or rare earth complexes, polythiophenes, polyphenyls Polymer compounds such as ylene and polyphenylenevinylene, organic silanes, and derivatives thereof.

Although the specific example of a fluorescent light emitting material is shown below, this invention is not limited to these.

[Formula 40]

(41)

(42)

(43)

(44)

[Chemical Formula 45]

(46)

It is preferable that content of the fluorescent luminescent material in the light emitting layer of this invention is 1-30 mass% in a light emitting layer, It is more preferable that it is 1-20 mass%, It is further more preferable that it is 1-10 mass%.

Although the thickness of a light emitting layer is not specifically limited, Usually, it is preferable that it is 2 nm-500 nm, Especially, it is more preferable that it is 5 nm-200 nm from a viewpoint of external quantum efficiency, It is still more preferable that it is 10 nm-100 nm. Do.

The light emitting layer in the element of this invention may be comprised only by the light emitting material, and may be the structure made into the mixed layer of a host material and a light emitting material. The kind of light emitting material may be 1 type, or 2 or more types may be sufficient as it. The host material is preferably a charge transporting material. The host material may be one kind or two or more kinds, and for example, a structure in which a host material having electron transporting property and a host material having hole transporting property are mixed. Moreover, the light emitting layer may contain a material which does not have charge transportability and which does not emit light.

The light emitting layer may be one layer or a multilayer of two or more layers, each layer may contain the same light emitting material or host material, or may contain different materials for each layer. When there are a plurality of light-emitting layers, each light-emitting layer may emit light of a different color.

(Host material)

The host material is a compound mainly responsible for the injection and transport of electric charges in the light emitting layer, and the compound itself does not substantially emit light. Here, the term "not substantially emitting light" means that the amount of emitted light from the compound that does not substantially emit light is preferably 5% or less of the total amount of light emitted from the entire device, more preferably 3% or less, and still more preferably 1 It means that it is% or less.

As a host material, the compound represented by General formula (1) can be used.

As another host material which can be used for this invention, the following compounds are mentioned, for example.

Pyrrole, indole, carbazole, azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole, imidazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran , Polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, arylamine, amino substituted chalcone, styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatic tertiary amine compound, styrylamine compound, Porphyrin compounds, cyclic aromatic hydrocarbon compounds (fluorene, naphthalene, phenanthrene, triphenylene, etc.), polysilane compounds, poly (N-vinylcarbazole), aniline copolymers, thiophene oligomers, polythiophenes, etc. Conductive polymer oligomer, organosilane, carbon film, pyridine, pyrimidine, triazine, imidazole, pyrazole, triazole, oxazole, oxadiazole, fluorenone, anthraquinomimethane, anthrone, diphenylquinone, Thiopyran dioxide, car Heterocyclic tetracarboxylic anhydrides such as bodyimide, fluorenylidenemethane, distyrylpyrazine, fluorine-substituted aromatic compounds, naphthaleneperylene, metal complexes of phthalocyanine, 8-quinolinol derivatives, metalphthalocyanine, benzoxazole, Various metal complexes and derivatives thereof (which may have a substituent or a condensation) etc. which are represented by the metal complex which makes benzothiazole a ligand are mentioned.

Among these, carbazole, dibenzothiophene, dibenzofuran, arylamine, a cyclic aromatic hydrocarbon compound and a metal complex 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 this invention, it is preferable that the said light emitting layer contains a host material. It is preferable that the said host material is a compound represented by General formula (1), or a compound represented by following General formula (4-1) or (4-2).

In this invention, when the compound represented by General formula (1) is contained in the organic layer (preferably a hole block layer) between a light emitting layer and a cathode, it is represented by General formula (4-1) or (4-2) in a light emitting layer. It is preferable to contain at least 1 or more of a compound.

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

The compound represented by general formula (4-1) or (4-2) may contain only one type in any organic layer, and the compound represented by some general formula (4-1) or (4-2) arbitrary It may contain in combination in ratio.

[Formula 47]

(In the general formula (4-1) and (4-2), d, e represents an integer of 0 to 3, and at least one is 1. F represents an integer of 1 ~ 4. R _'8 are each independently represents a substituent group, "may be the ₈ are different from each other are the same. in addition, R 'd, e, R not less than f 2, at least one of the ₈ shows a carbazole group represented by the following general formula (5) )

(48)

(In General formula (5), R ' ₉ represents a substituent each independently. G represents the integer of 0-8.)

R ' ₈ each independently represents a substituent, and is a substituent represented by a halogen atom, an alkoxy group, a cyano group, a nitro group, an alkyl group, an aryl group, a heterocyclic group, or general formula (5). When R ' ₈ does not represent General formula (5), Preferably it is a C10 or less alkyl group, a C10 or less substituted or unsubstituted aryl group, More preferably, it is a C6 or less alkyl group.

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, a heterocyclic group, preferably an alkyl group having 10 or less carbon atoms, or a substituent having 10 or less carbon atoms. Or an unsubstituted aryl group, More preferably, it is a C6 or less alkyl group.

g represents the integer of 0-8, and 0-4 are preferable from a viewpoint which does not shield too much the carbazole skeleton which is responsible for charge transport. In addition, from the viewpoint of ease of synthesis, when the carbazole has a substituent, it is preferable to have a substituent so as to be symmetrical with respect to the nitrogen atom.

In general formula (4-1), it is preferable that the sum of d and e is two or more from a viewpoint of maintaining charge transport ability. Further, it is preferable that R _'8 are substituted in the meta with respect to the other benzene ring. As a reason for this, in ortho substitution, since the steric hindrance of neighboring substituents is large, bonds tend to be cleaved and durability becomes low. Further, in para substitution, the molecular shape is closer to a rigid rod, and thus crystallization is easy, so that device deterioration at high temperature conditions is likely to occur. It is preferable that it is a compound specifically, represented by the following structure.

(49)

In general formula (4-2), it is preferable that f is 2 or more from a viewpoint of maintaining charge transport ability. When f is 2 or 3, it is preferable from the same viewpoint that R ' ₈ is mutually substituted by meta. It is preferable that it is a compound specifically, represented by the following structure.

(50)

When General Formula (4-1) and (4-2) have a hydrogen atom, the isotope of hydrogen (deuterium atom etc.) is also included. In this case, all the hydrogen atoms in the compound may be substituted with a hydrogen isotope, or a mixture may be a compound in which a part contains a hydrogen isotope. Preferably, R ' ₉ in General formula (5) is substituted by deuterium, Especially preferably, the following structures are mentioned.

(51)

In addition, the atom which comprises a substituent shows 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, the carbazole compound is synthesized by dehydrogenation after azakov potential reaction of a condensate of arylhydrazine and cyclohexane derivatives (LF Tieze, Th. Eicher, Takano, Ogasawara Translation, Precision Organic Synthesis). , P. 339 (published by Nankodo). In addition, regarding the coupling reaction using the palladium catalyst of the obtained carbazole compound and the halogenated aryl compound, tetrahedron Letters 39 vol. 617 (1998), 39 vol. 2367 (1998) and The method described in the 40 volume 6393 (1999) etc. is mentioned. There is no limitation in particular about reaction temperature and reaction time, The conditions described in the said document can be applied. In addition, some compounds, such as mCP, can use a commercially available thing preferably.

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 wet processes such as solution coating can also be preferably used. The molecular weight of the compound is preferably 2,000 or less, more preferably 1,200 or less, and particularly preferably 800 or less, from the viewpoints of suitability for deposition and solubility. In addition, from the viewpoint of vapor deposition aptitude, if the molecular weight is too small, the vapor pressure becomes small, a change from the gas phase to the solid phase does not occur, and it becomes difficult to form an organic layer. Therefore, 250 or more is preferable, and 300 or more is particularly preferable.

It is preferable that general formula (4-1) and (4-2) are the structure shown below, or the compound whose hydrogen atom substituted by 1 or more deuterium atom. R in the structure shown below, wherein R ₉ in the formula (5) 'are as defined _9. R _'8 is R in the formula (4-1) and (4-2) "means the same as _8.

(52)

Although the specific example of the compound represented by General formula (4-1) and (4-2) in this invention below is illustrated, this invention is not limited to these.

(53)

[Formula 54]

(55)

(56)

(57)

(58)

In the light emitting layer, it is preferable that the triplet minimum excitation energy (T ₁ energy) of the host material is higher than the T ₁ energy of the phosphorescent light emitting material in terms of color purity, luminous efficiency, and driving durability. T ₁ of the host material is 0.1 eV or more larger is preferable, or more preferably 0.2 eV greater than that, and at least 0.3 eV greater than the T ₁ of the phosphorescent light emitting material is more preferable.

Because dumping by T ₁ of the host material is a luminescent quenching is less than the T ₁ of the phosphorescent light emitting material has a host material is greater than T ₁ is required phosphorescent material. In addition, even when T ₁ of the host material is larger than the phosphorescent light-emitting material, in the case of both T ₁ difference is small, because occur reverse transfer of energy to the host material in the part, the phosphorescent light emitting material, causing decreased efficiency degradation or durability . Accordingly, a host material having a sufficiently large T ₁ and high chemical stability and carrier injection and transportability is desired.

In addition, although content of the host compound in this invention is not specifically limited, It is preferable that it is 15 mass% or more and 95 mass% or less with respect to the mass of the whole compound which forms a light emitting layer from a viewpoint of luminous efficiency and a drive voltage. When the luminescent layer contains plural kinds of host compounds containing the compound represented by the general formula (1), the compound represented by the general formula (1) is preferably 50 mass% or more and 99 mass% or less in all the host compounds.

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 array control agent, and an intermolecular interaction regulator. Although what kind of thing may be sufficient as an additive, it is preferable that it is a hydrocarbon water compound.

[Compound represented by formula (M-1)] [

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

Although the compound represented by general formula (M-1) is more preferable to be contained in the organic layer adjacent to the light emitting layer between a light emitting layer and an anode, the use is not limited and may be contained in any layer in an organic layer further. As an introduction layer of the compound represented by general formula (M-1) which concerns on this invention, any of a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, a charge block layer, It may contain.

As for the organic layer adjacent to the light emitting layer between a light emitting layer and an anode which the compound represented by general formula (M-1) contains, it is more preferable that it is a hole transport layer.

[Chemical Formula 59]

In formula (M-1), Ar ₁ and Ar ₂ are each independently selected from alkyl, aryl, heteroaryl, arylamino, alkylamino, morpholino, thiomorpholino, N, O, and S The 5 or 6 membered heterocycloalkyl or cycloalkyl containing the above hetero atom may be shown, and may have a substituent Z further. 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, arylamino, and may further have a substituent Z.

Z are each 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 '', and R '' Each 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.

p is an integer of _1-4, and when p is 2 or more, Ar <_1> and Ar <_2> may respectively be same or different.

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

(60)

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 C1-C8), an aryl group (preferably C6-C30), or heteroaryl group (preferably C4-C12). These may have the substituent Z mentioned above. R ^M1 is preferably an aryl group or a heteroaryl group, more preferably an aryl group. The preferable substituent when the aryl group of R ^M1 has a substituent includes an alkyl group, a halogen atom, a cyano group, an aryl group and an alkoxy group, more preferably an alkyl group, a halogen atom, a cyano group or an aryl group, An anion group, or an aryl group is more preferable. The aryl group of R ^M1 is preferably a phenyl group which may have a substituent Z, and more preferably a phenyl group which may have an alkyl group or a cyano group.

R ^M2 to R ^M23 each independently represent 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), and alkoxy Group (preferably C1-8), aryloxy group (preferably C6-C30), amino group (preferably C0-24), silyl group (preferably C0-18), cyano group, A nitro group or a fluorine atom may be shown and these may have the substituent Z mentioned above.

R ^M2 , R ^M7 , R ^M8 , R ^M15 , R ^M16 and R ^M23 are preferably an alkyl group or an aryl group which may have a hydrogen atom or a substituent Z, and 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 group or an aryl group which may have a substituent Z, or a fluorine atom, and more preferably a hydrogen atom.

R ^M3 , R ^M6 , R ^M9 , R ^M14 , R ^M17, and R ^M22 are preferably a hydrogen atom, an alkyl group which may have a substituent Z or an aryl group, a fluorine atom, or a cyano group, and more preferably a hydrogen atom Or an alkyl group which may have a substituent Z, more preferably a hydrogen atom.

R ^M10 , R ^M13 , R ^M18 and R ^M21 are preferably a hydrogen atom, an alkyl group which may have 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 Is an alkyl group or aryl group which may have a hydrogen atom, the substituent Z, a nitro group, a fluorine atom, or a cyano group, More preferably, it is an alkyl group which may have a hydrogen atom or the substituent Z. As a substituent in the case where an alkyl group has a substituent, a fluorine atom is preferable, Carbon number of the alkyl group which may have a substituent Z becomes like this. Preferably it is 1-6, More preferably, it is 1-4.

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

(61)

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, represents a halogen atom, an aryl group or a heteroaryl group, Z may have a substituent further. R each 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 there exist some R <^S1> -R <^S5> , they may combine with each other, may form the ring, and may have a substituent Z further.

a represents the integer of 0-4, and when some R <^S1> exists, they may be same or different, and may mutually combine and form a ring. b-e respectively independently represent the integer of 0-5, and when some R <^S2> -R <^S5> respectively exists, they may be same or different, and arbitrary two may combine and form a ring.

q is an integer of 1-5, when q is 2 or more, some R <^S1> may be same or different, and may combine with each other and may form the ring.

The alkyl group may have a substituent, may be saturated or unsaturated, and the group mentioned above may be mentioned. The alkyl group represented by R ^S1 to R ^S5 is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, for example, a methyl group, an ethyl group, an i-propyl group, Cyclohexyl group, t-butyl group, etc. are mentioned.

The cycloalkyl group may have a substituent, may be saturated or unsaturated, and the above-mentioned substituent Z may be mentioned as a group which may be substituted. The cycloalkyl group represented by R ^S1 to R ^S5 is preferably a cycloalkyl group having 4 to 7 ring atoms, more preferably a cycloalkyl group having 5 to 6 carbon atoms, for example, a cyclopentyl group and a cyclohexyl group Etc. can be mentioned.

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, etc. are mentioned.

As an alkynyl group represented by R <^S1> -R <^S5> , Preferably it is C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2-C10, 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 groups are substituted 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, for example, a phenyl group, tolyl group, biphenyl group, terphenyl group, and the like.

The heteroaryl group represented by R ^S1 to R ^S5 is preferably a heteroaryl group having 5 to 8 carbon atoms, more preferably a substituted or unsubstituted heteroaryl group having 5 or 6 atoms, for example a pyridyl group, Pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, cinnaolinyl, phthalazinyl, quinoxalinyl, pyrrolyl, indolyl, fu Aryl group, benzofuryl group, 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, isooxazolyl group, benzisooxazolyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, imidazolidinyl group, thiazolinyl group , Sulfolanyl group, carbazolyl group, dibenzofuryl group, dibenzo On it may be mentioned groups, such as group turn-pyrido [deg. Preferable examples are pyridyl group, pyrimidinyl group, imidazolyl group and thienyl group, and more preferably, 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, a heteroaryl group, and more preferably a hydrogen atom , An alkyl group, a cyano group, a trifluoromethyl group, a fluoro group, and an aryl group, and more preferably a hydrogen atom, an alkyl group, or 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 two of R ^S1 to R ^S5 may be bonded to each other to form a condensed 4 to 7 membered ring, the condensed 4 to 7 membered ring is cycloalkyl, aryl or heteroaryl, and the condensed 4 to 7 membered ring is further added. May have a substituent Z. The definitions and preferred ranges of the cycloalkyl, aryl and heteroaryl formed are the same as the cycloalkyl group, aryl group and heteroaryl group defined in R ^S1 to R ^S5 .

When using the compound represented by general formula (M-1) in a positive hole transport layer, it is preferable that 50-100 mass% of compounds represented by general formula (M-1) are contained, and 80-100 mass% is preferable. And it is especially preferable to contain 95-100 mass%.

In addition, when using the compound represented by general formula (M-1) for several organic layers, it is preferable to contain in the said range in each layer.

The compound represented by general formula (M-1) may contain only one type in any organic layer, and may contain the compound represented by some general formula (M-1) in combination at arbitrary ratios.

As thickness of the positive hole transport layer containing the compound represented by general formula (M-1), it is preferable that it is 1 nm-500 nm, It is more preferable that it is 3 nm-200 nm, It is still more preferable that it is 5 nm-100 nm. . In addition, the hole transport layer is preferably formed in contact with the light emitting layer.

The hole transport layer may be a single layer structure composed of one or two or more kinds of the above-described materials, or may be a multilayer structure composed of a plurality of layers of the same composition or different compositions.

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

The hydrogen atom which comprises general formula (M-1) also contains the isotope of hydrogen (deuterium atom etc.). In this case, all the hydrogen atoms in the compound may be substituted with a hydrogen isotope, or a mixture may be a compound in which a part contains a hydrogen isotope.

The compound represented by general formula (M-1) can be synthesize | combined combining various well-known synthesis methods. Most commonly, the carbazole compound is synthesized by dehydrogenation after azakov potential reaction of a condensate of arylhydrazine and cyclohexane derivatives (LF Tieze, Th. Eicher, Takano, Ogasawara Translation, Precision Organic Synthesis). , P. 339 (published by Nankodo). In addition, regarding the coupling reaction using the palladium catalyst of the obtained carbazole compound and the halogenated aryl compound, Tetrahedron Letters 39 vol. 617 (1998), 39 vol. 2367 (1998) and 40 vol. The method described in page 6393 (1999) etc. is mentioned. It does not specifically limit about reaction temperature and reaction time, The conditions described in the said document can be applied.

Although it is preferable to form a thin layer by the vacuum vapor deposition process, the compound represented by general formula (M-1) of this invention can also use wet processes, such as solution coating, suitably. The molecular weight of the compound is preferably 2,000 or less, more preferably 1,200 or less, and particularly preferably 800 or less, from the viewpoints of suitability for deposition and solubility. In addition, from the viewpoint of vapor deposition aptitude, if the molecular weight is too small, the vapor pressure becomes small, a change from the gas phase to the solid phase does not occur, and it becomes difficult to form an organic layer. Therefore, 250 or more is preferable, and 300 or more is particularly preferable.

Although the specific example of a compound represented by general formula (M-1) is shown below, this invention is not limited to these.

[Formula 62]

(63)

&Lt; EMI ID =

(65)

[Formula 66]

[Compound represented by the general formula (O-1)] [

It is preferable that the light emitting element of this invention contains an organic layer of at least 1 layer between a light emitting layer and a cathode, and it is the efficiency and the drive | operation that an organic layer contains at least 1 type of compound represented by following General formula (O-1). It is preferable from a voltage point of view.

General formula (O-1) is demonstrated below.

(67)

(In General Formula (O-1), R ^O1 represents an alkyl group, an aryl group, or a heteroaryl group. A ^O1 to A ^O4 each independently represent CR ^A or a nitrogen atom. R ^A represents a hydrogen atom, an alkyl group, or an aryl. Group or heteroaryl group, and a plurality of R ^{A 's} may be the same as or different from each other, L ^O1 represents a divalent to hexavalent linking group consisting 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 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), and these are selected from the substituent group A described above You may have a substituent to become. R ^O1 is preferably an aryl group or a heteroaryl group, more preferably an aryl group. In the case where the aryl group of R ^O1 has a substituent, preferable substituents include an alkyl group, an aryl group or a cyano group, more preferably an alkyl group or an aryl group, and still more preferably an aryl group. When the aryl group of R ^O1 has plural substituents, the plural 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 an alkyl group or a phenyl group which may be substituted with an aryl group, still more preferably an unsubstituted phenyl group or 2-phenylphenyl group. to be.

A ^O1 to A ^O4 each independently represent a CR ^A or a nitrogen atom. A ^O1 ~ A 0 ~ 2 ^O4 of the dog preferably a nitrogen atom, and more preferably 0 or one is the nitrogen atom. It is more preferred that all of A ^O1 to A ^O4 are CR ^A or A ^O1 is a nitrogen atom, A ^O2 to A ^O4 are CR ^A , A ^O1 is a nitrogen atom, and A ^O2 to A ^O4 are CR ^A It is more preferable that A ^O1 is a nitrogen atom, A ^O2 to A ^O4 are CR ^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), and these groups of substituents described above You may have a substituent selected from A. In addition, some R ^<A> may be the same and may differ. R ^A is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom.

L ^O1 represents a divalent to hexavalent linking group consisting of an aryl ring (preferably having 6 to 30 carbon atoms) or a heteroaryl ring (preferably having 4 to 12 carbon atoms). As L ⁰¹ , it is preferably an arylene group, a heteroarylene group, an aryltriyl group or a heteroaryltriyl group, more preferably a phenylene group, a biphenylene group or a benzenetriyl group, more preferably a biphenylene group, Or a benzenetriyl group. L ^O1 may have a substituent selected from the substituent group A described above, and the substituent in the case of having a substituent is preferably an alkyl group, an aryl group, or a cyano group. The following are mentioned as a specific example of L <^O1> .

(68)

n ^O1 represents an integer of 2 to 6, preferably an integer of 2 to 4, more preferably 2 or 3. n ^O1 is most preferably 3 from the viewpoint of device efficiency, and most preferably 2 from the viewpoint of durability of the device.

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

[Formula 69]

(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 represent a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group. A ^O1 -A ^O4 each independently represents CR ^A or a nitrogen atom, R ^A represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and a plurality of R ^A may be the same or different)

And R A and ^{O1 O1} ~ ^O4 A is the formula (O1) the same as defined in R and A ^{O1 O1} ~ ^O4 A, also the same even their preferred range.

R ^O2 to R ^O4 each independently represent 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) They may have a substituent selected from the substituent group A mentioned above. R ^O2 to R ^O4 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) is a glass transition temperature (Tg) is from 100 to 300 ℃ from the viewpoint of operating stably with respect to stability at high temperature storage, heat generation during driving at high temperature. It is preferable that it is 120 degreeC-300 degreeC, It is more preferable that it is 120 degreeC-300 degreeC, It is still more preferable that it is 140 degreeC-300 degreeC.

Although the specific example of a compound represented by general formula (O-1) is shown below, this invention is not limited to these.

(70)

(71)

The compound represented by the said general formula (O-1) can be synthesize | combined by the method of Unexamined-Japanese-Patent No. 2001-335776. After the synthesis, it is preferable to perform purification by column chromatography, recrystallization, reprecipitation or the like, and then purification by sublimation purification. It is possible not only to separate the organic impurities by the sublimation purification but also to effectively remove inorganic salts, residual solvents, water and the like.

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 preferably contained in the layer on the cathode side adjacent to the light emitting layer.

The compound represented by formula (O-1) is preferably contained in an amount of 70 to 100 mass%, more preferably 85 to 100 mass%, based on the total mass of the organic layer to be added.

It is preferable that the light emitting element of this invention contains at least 1 layer of organic layer between a light emitting layer and a cathode, and containing at least 1 type of compound represented by the following general formula (P) in the organic layer of the efficiency and drive voltage of an element It is preferable from a viewpoint. General formula (P) is demonstrated below.

(72)

(In general formula (P), ^RP represents an alkyl group (preferably C1-C8), an aryl group (preferably C6-C30), or heteroaryl group (preferably C4-C12), which are optionally the aforementioned substituents have a substituent selected from the group a. nP is the case of an integer of 1 ~ 10, R ^P is a plurality, they may be the same or different. R ^P and at least one is to the general It is a substituent represented by Formula (P-1)-(P-3).

(73)

(In General Formulas (P-1) to (P-3), R ^P1 to R ^P3 and R ' ^P1 to R' ^P3 each represent an alkyl group (preferably having 1 to 8 carbon atoms) and an aryl group (preferably having 6 carbon atoms). To 30) or a heteroaryl group (preferably having 4 to 12 carbon atoms), and these may have a substituent selected from the substituent group A described above.n ^P1 and n ^P2 represent an integer of 0 to 4 and R If ^{P1 ~ R P3, R 'P1} ~ R' P3 is a plurality, they may be the same or different. L ^P1 ~ L ^P3 represents any of a divalent linking group consisting of a single bond, an aryl ring or heteroaryl ring * Indicates the bonding position with the anthracene ring of formula (P)))

Preferred substituents other than the substituents represented by (P-1) to (P-3) as R ^P are aryl groups, more preferably a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group, more preferably a naphthyl group to be.

R ^P1 to R ^P3 and R ' ^P1 to R' ^P3 are preferably any of an aryl group and a heteroaryl group, more preferably an aryl group, still more preferably a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group. Either one is most preferably a phenyl group.

L ^P1 to L ^P3 are preferably any of a divalent linking group consisting of a single bond and an aryl ring, more preferably any of a single bond, phenylene, biphenylene, terphenylene, naphthylene, and more preferably. Is any of a single bond, phenylene and naphthylene.

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

&Lt; EMI ID =

(75)

The compound represented by the said general formula (P) can be synthesize | combined by the method as described in WO2003 / 060956, WO 2004/080975, etc. After the synthesis, it is preferable to perform purification by column chromatography, recrystallization, reprecipitation or the like, and then purification by sublimation purification. It is possible not only to separate the organic impurities by the sublimation purification but also to effectively remove inorganic salts, residual solvents, water and the like.

In the light emitting device of the present invention, the compound represented by the general formula (P) is contained in the organic layer between the light emitting layer and the cathode, but is preferably contained in a layer adjacent to the cathode.

It is preferable to contain 70-100 mass% 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 to contain 85-100 mass%.

(Charge transport layer)

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

As for the hole injection layer and the hole transport layer, the matters described in paragraphs [0165] to [0167] of JP2008-270736A can be applied to the present invention.

The hole injection layer preferably contains an electron accepting dopant. By incorporating the electron-accepting dopant in the hole injection layer, the hole injection property is improved, the driving voltage is lowered, and the efficiency is improved. The electron-accepting dopant may be any of an organic material and an inorganic material as long as it is a material capable of extracting electrons from the material to be doped to generate radical cations. For example, tetracyanoquinomimethane (TCNQ) or tetrafluor Rotetracyanoquinomethane (F ₄ -TCNQ), molybdenum oxide, and the like.

It is preferable to contain 0.01 mass%-50 mass% with respect to the mass of the whole compound which forms a hole injection layer, and, as for the electron accepting dopant in a hole injection layer, it is more preferable that 0.1 mass%-40 mass% are contained, 0.2 mass% It is more preferable to contain-30 mass%.

(Electron injection layer, electron transport layer)

The electron injection layer and the electron transport layer are layers having a function of receiving electrons from the cathode or cathode side and transporting them to the anode side. The electron injecting material and electron transporting material used in 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. As other materials, pyridine derivative, quinoline derivative, pyrimidine derivative, pyrazine derivative, phthalazine derivative, phenanthroline derivative, triazine derivative, triazole derivative, oxazole derivative, oxadiazole derivative, imidazole derivative, Aromatic ring tetra, such as fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide derivatives, fluorenylidene methane derivatives, distyrylpyrazine derivatives, naphthalenes, and perylenes Metal complexes of carboxylic anhydrides, phthalocyanine derivatives and 8-quinolinol derivatives, metal complexes represented by metal phthalocyanines, metal complexes containing benzoxazole or benzothiazole, organic silane derivatives represented by silol, and the like. It is preferable that it is a layer containing.

It is preferable that the thickness of an electron injection layer and an electron carrying layer is 500 nm or less from a viewpoint of lowering a drive voltage, respectively.

As thickness of an electron carrying layer, it is preferable that it is 1 nm-500 nm, It is more preferable that it is 5 nm-200 nm, It is further more preferable that it is 10 nm-100 nm. Moreover, as thickness of an electron injection layer, it is preferable that it is 0.1 nm-200 nm, It is more preferable that it is 0.2 nm-100 nm, It is further more preferable that it is 0.5 nm-50 nm.

The electron injection layer and the electron transport layer may have a single layer structure composed of one or two or more kinds of the above-described materials, or may have a multilayer structure composed of a plurality of layers of the same composition or different compositions.

The electron injecting layer preferably contains an electron donating dopant. By containing an electron donating dopant in an electron injection layer, there exists an effect that an electron injection property improves, a drive voltage falls, efficiency improves, etc. The electron donating dopant may be any of an organic material and an inorganic material as long as it can supply electrons to the doped material and generate radical anions. For example, tetrathiafulvalene (TTF) and tetrathianaphtha. And dihydroimidazole compounds such as sen (TTT) and bis- [1,3diethyl-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, more preferably 0.1% by mass to 40% by mass, and more preferably 0.5% by mass, based on the total mass of the compound forming the electron injection layer. It is more preferable to contain 30% by mass.

(Hole blocking layer)

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

Examples of the organic compound constituting the hole block layer include 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- And phenanthroline derivatives such as 1,10-phenanthroline (abbreviated as BCP).

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 be a single layer structure composed of one or more of the above-described materials, or a multilayer structure composed of plural layers of the same composition or different composition.

(Electronic block layer)

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

As an example of the organic compound which comprises an electron block layer, what was illustrated as the above-mentioned hole transport material is applicable, for example.

As thickness of an electron blocking layer, it is preferable that it is 1 nm-500 nm, It is more preferable that it is 3 nm-100 nm, It is still more preferable that it is 5 nm-50 nm.

The electron blocking layer may be a single layer structure composed of one or more of the above-described materials, or a multilayer structure composed of plural layers of the same composition or different compositions.

(Protective layer)

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

About a protective layer, the matter of Paragraph No. [0169]-[0170] of Unexamined-Japanese-Patent No. 2008-270736 can be applied to this invention.

(Bag container)

The element of this invention may seal the whole element using a sealing container.

About the sealing container, the matter described in Paragraph No. [0171] of Unexamined-Japanese-Patent No. 2008-270736 can be applied to this invention.

(Driving)

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

The driving method of the organic electroluminescent device of the present invention is disclosed in Japanese Laid-Open Patent Publication Nos. 2-148687, 6-301355, 5-29080, 7-134558, 8-234685, 8- 241047, Japanese Patent No. 2784615, U.S. Patent Nos. 5828429 and 6023308, and the like can be applied.

As external quantum efficiency of the organic electroluminescent element of this invention, 7% or more is preferable, 10% or more is more preferable, 12% or more is more preferable. The numerical value of external quantum efficiency can use the maximum value of the external quantum efficiency at the time of driving an element at 20 degreeC, or the value of the external quantum efficiency in the vicinity of 300-400 mW / m <2> when driving an element at 20 degreeC.

The internal quantum efficiency of the organic electroluminescent device of the present invention is preferably 30% or more, more preferably 50% or more, and still more preferably 70% or more. The internal quantum efficiency of the device is calculated by dividing the external quantum efficiency by the light extraction efficiency. In a typical organic EL device, the light extraction efficiency is about 20%. However, by studying the shape of the substrate, the shape of the electrode, the thickness of the organic layer, the thickness of the inorganic layer, the refractive index of the organic layer, To 20% or more.

(Use of the device of the present invention)

The element of the present invention can be suitably used for a display element, a display, a backlight, an electrophotographic, an illumination light source, a recording light source, an exposure light source, a read light source, a sign, a signboard, an interior, or an optical communication. In particular, it is used suitably for the device driven in the area | region where light emission brightness is high, such as an illumination 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 is made using the organic electroluminescent element.

2 is a cross-sectional view schematically showing an example of the light emitting device of the present invention. The light emitting device 20 of FIG. 2 is comprised by the transparent substrate (support substrate) 2, the organic electroluminescent element 10, the sealing container 16, etc. As shown in FIG.

The organic electroluminescent element 10 is configured by sequentially stacking an anode (first electrode) 3, an organic layer 11, and a cathode (second electrode) 9 on a substrate 2. Moreover, the protective layer 12 is laminated | stacked on the cathode 9, and the sealing container 16 is formed on the protective layer 12 via the adhesive layer 14. As shown in FIG. Further, a part of each of the electrodes 3 and 9, a partition wall, an insulating layer, and the like are omitted.

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

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

(Lighting device)

Next, the lighting apparatus of this invention is demonstrated with reference to FIG.

3 is a cross-sectional view schematically showing an example of the lighting apparatus of the present invention. As shown in FIG. 3, the lighting device 40 of the present invention includes the organic EL element 10 and the light scattering member 30 described above. More specifically, the lighting apparatus 40 is comprised so that the board | substrate 2 of the organic electroluminescent element 10 and the light-scattering member 30 may contact.

The light scattering member 30 is not particularly limited as long as it can scatter light, but in FIG. 3, the light scattering member 30 is a member in which the fine particles 32 are dispersed in the transparent substrate 31. As the transparent substrate 31, a glass substrate can be illustrated preferably, for example. As the microparticles | fine-particles 32, transparent resin microparticles | fine-particles can be illustrated preferably. As a glass substrate and transparent resin microparticles | fine-particles, a well-known thing can all be used. When the light emission from the organic electroluminescent element 10 is incident on the light incident surface 30A of the scattering member 30, the lighting device 40 scatters the incident light by the light scattering member 30 to generate scattered light. It emits as illumination light from the light output surface 30B.

Example

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

1. Synthetic Example

(Synthesis Example 1) Synthesis of Compound 1

[Formula 76]

4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -1,3,2-dioxaborane 1.77 g (5.00 mmol), 4-bromo-4'-t- Butylbiphenyl 1.59 g (5.50 mmol), tris (dibenzylideneacetone) dipalladium (Pd ₂ (dba) ₃ ) 229 mg (0.25 mmol), 2-dicyclohexylphosphino-2 ', 6'- Dimethoxybiphenyl (SPhos) 410 mg (1.00 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 for 10 hours under a nitrogen atmosphere. Heated to reflux. 200 ml of toluene was added to the reaction liquid, and after cooling to room temperature, solid content was isolate | separated by Celite filtration. After extracting the organic layer 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 compounds 1 were obtained by recrystallization with toluene / ethanol (4: 1) (yield 60%).

NMR data of Compound 1

Synthesis Example 2 Synthesis of Compound 2

[Formula 77]

4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -1,3,2-dioxaborane 7.08 g (20.0 mmol), 22.6 g (80.0 p-bromoiobenzene) 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, 50 ml of pure waters were mixed and heated to reflux for 6 hours under a nitrogen atmosphere. After cooling the reaction solution to room temperature, the solid was filtered and washed sequentially with pure water, ethanol and hexane. 6.15g of synthetic intermediate 1 was obtained by falling and wash | cleaning this solid by ethanol (yield 80%).

3.60 g (9.39 mmol) of synthetic intermediate 1, 3.58 g (14.1 mmol) of bis (pinacolato) diboron, [1,1'-bis (diphenylphosphino) ferrocene] palladium dichloridedichloromethane complex ( 1: 1) (PdCl ₂ (dppf) ₂ ) 229 mg (0.28 mmol), potassium acetate (AcOK) 2.77 g (28.2 mmol), and 80 ml of dimethyl sulfoxide (DMSO) were mixed, and it was 70 degreeC under nitrogen atmosphere. Stirred for 3 hours. The reaction solution was poured into ice water, and the precipitated solid was filtered and washed sequentially with pure water and methanol. Thereafter, the residue was purified by silica gel chromatography (developing solvent toluene: hexane = 1: 1) to obtain 1.30 g of the synthetic intermediate 2 (32%).

1.46 g (3.50 mmol) of the synthetic intermediate 2, 1.66 g (3.85 mmol) of the synthetic intermediate 3, 96 mg (0.11 mmol) tris (dibenzylideneacetone) dipalladium, 172 mg (0.42 mmol) of SPhos, 1.49 g (7.00 mmol) of potassium phosphate, 15 mL of DME, and 7 mL of pure water were mixed and heated to reflux for 7 hours under a nitrogen atmosphere. After cooling the reaction solution to room temperature, the solid was filtered and washed sequentially with pure water, ethanol and hexane. Thereafter, 700 mg of Compound 2 was obtained by dropwise washing with ethanol and toluene (40%).

NMR data of Compound 2

Synthesis Example 3 Synthesis of Compound 5

(78)

2.50 g (6.54 mmol) of the synthetic intermediate 1, 2.74 g (7.2 mmol) of the synthetic intermediate 4, 180 mg (0.20 mmol) tris (dibenzylideneacetone) dipalladium, 540 mg (1.31 mmol), SPhos, 2.78 g (13.1 mmol) of potassium phosphate, 30 ml of DME, and 15 ml of pure water were mixed and heated to reflux for 6 hours under a nitrogen atmosphere. After cooling the reaction solution to room temperature, the solid was filtered and washed sequentially with pure water, ethanol and hexane. Thereafter, 1.4 g of Compound 5 was obtained by dropwise washing with ethanol and toluene (39%).

NMR data of Compound 5

Synthesis Example 4 Synthesis of Compound 7

(79)

27.4 g (100 mmol) of 3,5-diphenylphenylboronic acid, 3.11 g (110 mmol) of 3-bromoiobenzene, 1.12 g (5.0 mmol) of palladium acetate, 5.24 g (20.0 m) of triphenylphosphine Mol), 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 for 9 hours under a nitrogen atmosphere. Saturated saline was added to the reaction solution, and the organic layer was extracted. The organic layer was concentrated under reduced pressure, and then purified by silica gel column chromatography (developing solvent hexane / ethyl acetate (4: 1)) to obtain 38.1 g of a synthetic intermediate 5 (yield 99%).

19.3 g (50.0 mmol) of synthetic intermediate 5, 15.2 g (60.0 mmol) of bis (pinacolato) diboron, [1,1'-bis (diphenylphosphino) ferrocene] palladium dichloridedichloromethane 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 it stirred at 70 degreeC under nitrogen atmosphere for 8 hours. The reaction solution was poured into 300 ml of ice-cold pure water, and the precipitated solid was filtered. The solid was purified by silica gel column chromatography (hexane / ethyl acetate (50: 1 → 20: 1 → 10: 1)), dissolved with toluene, crystallized by adding hexane, and synthesized. 18.6 g of intermediates 6 were obtained (yield 86%).

4.32 g (10.0 mmol) of the synthetic intermediate 6, 3.27 g (11.0 mmol) of 2-bromo-5-iodinetoluene, 112 mg (0.5 mmol) of palladium acetate, 525 mg (2.0 mmol) of triphenylphosphine , 2.76 g (20.0 mmol) of potassium carbonate, 10 ml of toluene, 2 ml of ethanol, and 4 ml of pure water were mixed and heated to reflux for 11 hours under a nitrogen atmosphere. After the reaction, the organic layer was extracted by separation, and then 1.5 g of a synthetic intermediate 7 was obtained by silica gel column chromatography (developing solvent: hexane / ethyl acetate (100: 1, 50: 1, 10: 1)). Yield 32%).

1.43 g (3.0 mmol) of synthetic intermediate 7, 1.06 g (3.0 mmol) of 4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -1,3,2-dioxaborane ), Palladium acetate 34 mg (0.15 mmol), triphenylphosphine 157 mg (0.60 mmol), sodium carbonate 954 mg (9.0 mmol), 30 ml of tetrahydrofuran (THF), and 10 ml of pure water were mixed to obtain nitrogen. It was heated to reflux for 7.5 hours under the atmosphere. After the reaction, hexane was added, and the precipitate was filtered off. This 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

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

(80)

Compound 3 is synthetic intermediate 3 to synthetic intermediate 8, compound 4 to synthetic intermediate 3 to synthetic intermediate 9, compound 6 to synthetic intermediate 3 to synthetic intermediate 10, compound 9 to synthetic intermediate 3 to synthetic intermediate 12, compound 10 Silver was synthesized in the same manner as in Synthesis Example 2 except that the synthetic intermediate 3 was changed to the synthetic intermediate 13, respectively.

Compound 8 was synthesized in the same manner as in Synthesis Example 1 except for changing 4-bromo-4'-t-butylbiphenyl to synthetic intermediate 11.

Synthesis Example 5 Synthesis of Compound 12

[Formula 81]

7.92 g (40.0 mmol) of 4-biphenylboronic acid, 24.96 g (80.0 mmol) of 3,3'-dibromo-1,1'-biphenyl, 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 and refluxed under a nitrogen atmosphere for 8 hours. The reaction solution was cooled to room temperature, the organic layer was extracted by liquid separation, and the origin component was removed by silica gel column chromatography (developing solvent: toluene). The solvent was distilled off under reduced pressure, washed with ethanol, and then heated to reflux with 200 ml of toluene, and the solid content precipitated at room temperature was filtered off. The obtained solution was concentrated, crystallized with hexane, and washed with hexane to obtain 8.82 g of the 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 dichloridedichloromethane complex ( 1: 1) (PdCl ₂ (dppf)) 392 mg (0.48 mmol), 3.61 g (36.8 mmol) of potassium acetate (AcOK) and 100 ml of dimethyl sulfoxide (DMSO) were mixed and mixed at 70 ° C under a nitrogen atmosphere. Stir for 4 hours. After returning a reaction liquid to room temperature, solid content was filtered through Celite, the obtained solution was liquid-separated, and the organic layer was extracted. The organic layer was concentrated under reduced pressure, and then 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- (triphenylen-2-yl) -1,3,2-dioxaborane 7.08 g (20.0 mmol), 5-bromo-2-iodotoluene 11.88 g (40.0 mmol), tris (dibenzylideneacetone) dipalladium 549 mg (0.60 mmol), 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl 985 mg (2.40 mmol), 8.49 g (40.0 mmol) of potassium phosphate, 80 ml of toluene, and 40 ml of water were mixed and heated to reflux for 5 hours under a nitrogen atmosphere. After returning a reaction liquid to room temperature, the organic layer was extracted by liquid separation. The organic layer was concentrated under reduced pressure, and then purified by silica gel chromatography (developing solvent: toluene: hexane 1: 5) to obtain 5.06 g of a 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 it heated and refluxed under nitrogen atmosphere for 3 hours. After the solid content in the reaction liquid was filtered through Celite, the organic layer was extracted by liquid separation, and the origin component was removed by silica gel chromatography (developing solvent: toluene). The obtained solution was concentrated under reduced pressure, and 3.15 g of compounds 12 were obtained by recrystallizing three times with toluene / hexane (2: 1) (yield 84%).

NMR data of Compound 12

(Synthesis of Compounds 11 and 13 to 18)

(82)

Compound 11 was the same as in 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 for changing 5-bromo-2-iod toluene to 2-bromo-5-iod toluene and compound 14 to synthetic intermediate 15, respectively.

Compound 15 synthesized except for changing synthetic intermediate 3 to synthetic intermediate 18, compound 16 to synthetic intermediate 2 to synthetic intermediate 19, synthetic intermediate 3 to synthetic intermediate 18, and compound 17 to synthetic intermediate 3 to synthetic intermediate 20, respectively. It synthesize | combined in the same manner as Example 2.

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. Device manufacturing and evaluation

All the materials used for element production were subjected to sublimation purification, and it was confirmed by high-performance liquid chromatography (TOSO-TSKgel ODS-100Z) that the purity (absorption intensity area ratio of 254 nm) was 99.9% or more.

(Example 1)

A glass substrate having an ITO film of 0.5 mm in thickness and 2.5 cm in width (Geomatec Co., Ltd., surface resistance 10 Ω / □ (Ω / sq.)) Was placed in a washing container, ultrasonically cleaned in 2-propanol, and then 30 minutes. UV-ozone treatment was performed. The following organic compound layers were sequentially deposited on this transparent anode (ITO film) by vacuum deposition.

Layer 1: LG101: film thickness 10 nm

Second layer: NPD: film thickness 32 nm

Third layer: host material and RD-1 (mass ratio 93: 7) described in Table 1: film thickness 30 nm

Fourth layer: Materials described in Table 1 (HBL materials): film thickness 5 nm

Fifth layer: ET-1: film thickness 50 nm

On this, 0.1 nm of lithium fluoride and 100 nm of metallic aluminum were deposited in this order to form a cathode.

The obtained laminated body was put into the glove box substituted with nitrogen gas, without contacting air | atmosphere, and it sealed using the glass sealing can and the ultraviolet curing adhesive agent (XNR5516HV, Nagase Chiba Corporation make), and the element 1-1. -1-13 and comparative elements 1-1-1-5 were obtained. Table 1 shows the results of evaluating these devices in terms of efficiency, drive voltage, durability, and drive voltage rise in the following manner.

(a) efficiency

A DC voltage was applied to each element to emit light using a Toyo Technica source measure unit 2400, and the luminance thereof was measured using a luminance meter BM-8 manufactured by Topcon Corporation. The emission spectrum and emission wavelength were measured using the Hamamatsu Photonics spectrum analyzer PMA-11. Based on these, the external quantum efficiency whose luminance is about 1000 mW / m <2> was computed by the brightness conversion method. In Table 1, the value of the comparative element 1-1, Table 2, the value of the comparative element 2-1, Table 3, the value of the comparative element 3-1, and Table 4 the value of the comparative element 4-1. In Table 5, the value of the comparative element 5-1 is shown in Table 5, the value of the comparative element 6-1 is shown in Table 6, and the value of the comparative element 7-1 is 10 in Table 7, respectively. . The greater the number, the better.

(b) Driving voltage

Each element is made to emit light by applying a DC voltage such that the luminance is 1000 mW / m 2. The applied voltage at this time was taken as an index of the evaluation of the driving voltage. In Table 1, the value of the comparative element 1-1, Table 2, the value of the comparative element 2-1, Table 3, the value of the comparative element 3-1, and Table 4 the value of the comparative element 4-1. In Table 5, the value of the comparative element 5-1 is shown in Table 5, the value of the comparative element 6-1 is shown in Table 6, and the value of the comparative element 7-1 is 10 in Table 7, respectively. . The smaller the number is, the more preferable the driving voltage is.

(c) durability

Each element was continued to emit light by applying a DC voltage so that the luminance became 5000 mW / m 2, and the time required until the luminance became 4000 mW / m 2 was used as an index of durability. In Table 1, the value of the comparative element 1-1, Table 2, the value of the comparative element 2-1, Table 3, the value of the comparative element 3-1, and Table 4 the value of the comparative element 4-1. In Table 5, the value of the comparative element 5-1 is shown in Table 5, the value of the comparative element 6-1 is shown in Table 6, and the value of the comparative element 7-1 is 10 in Table 7, respectively. . Durability is so preferable that a number is large.

(d) Drive voltage rise

(c) the difference (V'-V) (unit: V) between the voltage value V at the start of measurement (5000 mW / m 2) and the voltage value V 'at the end of the endurance evaluation (4000 mW / m 2); It was taken as an index.

(Example 2)

Except having changed the layer structure to what is shown below, the element was manufactured like Example 1, and the result of having evaluated similarly to Example 1 is shown in Table 2.

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

Fifth layer: ET-2: film thickness 50 nm

(Example 3)

Except having changed the layer structure to what is shown below, the element was manufactured like Example 1, and the result of having evaluated similarly to Example 1 is shown in Table 3.

First layer: GD-1: film thickness 10 nm

Second layer: NPD: film thickness 30 nm

Third layer: host material and GD-1 (mass ratio 90:10) described in Table 3: film thickness 30 nm

Fourth layer: ET-3: film thickness 45 nm

(Example 4)

Except having changed the layer structure to what is shown below, the element was manufactured like Example 1, and the result of having evaluated similarly to Example 1 is shown in Table 4. FIG.

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)

Except having changed the layer structure to what is shown below, the element was manufactured like Example 1, and the result of having evaluated similarly to Example 1 is shown in Table 5. FIG.

Layer 1: LG101: film thickness 10 nm

Second layer: NPD: film thickness 115 nm

Third layer: TPAC: film thickness 5 nm

Fourth layer: host material and Firpic (mass ratio 90:10) described in Table 5: film thickness 30 nm

5th layer: ET-4: film thickness 5nm

Sixth layer: ET-1: film thickness 25 nm

(Example 6)

Except having changed the layer structure to what is shown below, the element was manufactured like Example 1, and the result of having evaluated similarly to Example 1 is shown in Table 6. FIG.

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 width of 2.5 cm (TOO film) (manufactured by Geotech Co., Ltd., surface resistance of 10 Ω / □) was placed in a washing container, ultrasonically cleaned in 2-propanol, and then subjected to UV-ozone treatment for 30 minutes. It was. PEDOT (poly (3,4-ethylenedioxythiophene)) / PSS (polystyrenesulfonic acid) aqueous solution (BaytronP (standard product)) was spin-coated (4000 rpm, 60 seconds) on this transparent anode (ITO film), and 120 degreeC By drying for 10 minutes at, a hole injection transport layer having a film thickness of about 50 nm was formed.

Subsequently, 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 above-described buffer layer (hole injection transport layer) to obtain a film thickness of about 50 A light emitting layer of nm was formed.

ET-2 having a film thickness of about 45 nm was deposited on the light emitting layer by a vacuum deposition method to form an electron injection transport layer, and 0.1 nm of lithium fluoride and 100 nm of metal aluminum were deposited in this order to form a cathode.

The laminate was placed in a glove box substituted with nitrogen gas, without being brought into contact with the atmosphere, and sealed using a glass can and a UV-curable adhesive (XNR5516HV, manufactured by Nagase Chiba Co., Ltd.). -1 to 7-5 and Comparative elements 7-1 to 7-3 were obtained. The result of having evaluated similarly to Example 1 about these elements is shown in Table 7.

From the above result, the element using the compound represented by General formula (1) of this invention has high issuance efficiency, low drive voltage, excellent durability, and little voltage rise at the time of drive.

On the other hand, the compound which has a triphenylenyl group, a pyrenyl group, or an anthryl group as a substituent further in the structure of General formula (1) like the comparative compound 3, 4, or 5 is an efficiency, a voltage, It was inferior in terms of voltage rise over time. This is because the compound having a triphenylenyl group, a pyrenyl group, or an anthryl group as a substituent in addition to the structure of the general formula (1) is considered to have an π-conjugated system that is excessively enlarged, so that the T ₁ energy is too small and the efficiency is lowered. do.

In addition, the compounds having substituents at plural positions of the triphenylene skeleton, as in Comparative Compounds 2 and 6, were inferior in durability of the device and increase in voltage over time. In particular, in the case of having a substituent containing two benzene rings at the ortho position with respect to the triphenylene skeleton, a decrease in durability was remarkable.

The compound used by the Example and the comparative example is shown below.

(83)

(84)

(85)

&Lt; EMI ID =

[Chemical Formula 87]

Industrial availability

According to the present invention, it is possible to provide an organic electroluminescent element which has excellent luminous efficiency and durability, further has a low driving voltage and a small rise in voltage over time.

Moreover, according to this invention, the charge transport material which can be provided to the organic electroluminescent element which has the outstanding luminous efficiency and durability, and also has low drive voltage and small voltage rise over time can be provided.

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

This application is incorporated by reference in Japanese Patent Application No. 2010-171230, filed Jul. 29, 2010, Japanese Patent Application No. 2010-212884, filed September 22, 2010, and Japan, filed Oct. 29, 2010. Based on a patent application (patent application 2010-244821), the content is taken in here as a reference.

2: substrate
3: anode
4: Hole injection layer
5: hole transport layer
6: light emitting layer
7: Hole block layer
8: Electron transport layer
9: cathode
10: Organic electroluminescent device
11: Organic layer
12: Protective layer
14: Adhesive layer
16: Encapsulation container
20: Light emitting device
30: light scattering member
31: transparent substrate
30A: Light incident surface
30B: light exit surface
32: particulate
40: Lighting device

Claims (13)

An organic electroluminescent device having, on a substrate, a pair of electrodes consisting of an anode and a cathode and at least one organic layer including a light emitting layer between the electrodes, the organic electroluminescent device represented by at least one of the organic layers represented by the following general formula (1): An organic electroluminescent element containing a compound.
[Formula 1]

(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 them. P is 0 ~ represents the four integer, q is an integer of 0 to 5. However, p + q is 1 is an integer equal to or greater than. R, if _a and R _B with a plurality exist, _B a plurality of R _a and R are different may be the same respectively may be 2 or more R _B are bonded to each other, together with the benzene ring B, fluorene, and form a ring, a naphthalene ring, or a phenanthrene ring, and fluorene ring, naphthalene ring or phenanthrene ring is an alkyl group, It may have a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, a fluorine atom, or a group formed by combining them, provided that R _B does not form a condensation with the benzene ring A). The method of claim 1,
The organic electroluminescent device according to which R _A and R _B are each independently represented by the following group (Arx).
(2)

(In the group (Arx), Ara to Ard each independently represent a ring selected from benzene ring, naphthalene ring, fluorene ring and phenanthrene ring. Na, nb and nc each independently represent 0 or 1, nd represents 1. When na, nb and nc are 0, Ara to Arc represent a single bond, and Ara to Ard each independently represent an alkyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, a silyl group, Or a fluorine atom, and the alkyl group, phenyl group, naphthyl group, fluorenyl group, phenanthryl group, or silyl group may further be an alkyl group, phenyl group, naphthyl group, fluorenyl group, phenanthryl group, silyl group, or fluorine atom. May be substituted with * represents a binding site to benzene ring A or benzene ring B of the general formula (1). 3. The method according to claim 1 or 2,
The organic electroluminescent element whose molecular weight of the compound represented by the said General formula (1) is 400 or more and 1000 or less. The method according to any one of claims 1 to 3,
An organic electroluminescent device comprising at least one phosphorescent light emitting material in the light emitting layer. 5. The method of claim 4,
An organic electroluminescent element, wherein the phosphorescent material is represented by the following general formula (E-1).
(3)

(In General Formula (E-1), Z ¹ and Z ² each independently represent a carbon atom or a nitrogen atom.
A ₁ represents a group of atoms that together with Z ¹ and a nitrogen atom form a heterocyclic ring of 5 or 6 atoms.
B ₁ represents an atomic group which forms a 5 or 6 membered ring together with Z ² and a carbon atom.
(XY) represents a monoanionic bidentate ligand.
n _E1 represents an integer of 1 to 3) The method of claim 5, wherein
The organic electroluminescent element in which the phosphorescence emitting material represented by said general formula (E-1) is represented with the following general formula (E-2).
[Chemical Formula 4]

(In Formula (E-2), A ^E1 to A ^E8 each independently represent a nitrogen atom or CR ^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 method of claim 5, wherein
The organic electroluminescent element in which the phosphorescence emitting material represented by said general formula (E-1) is represented with the following general formula (E-6).
[Chemical Formula 5]

(In General Formula (E-6), R _1a to R _1k are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, a trifluorovinyl group, and -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. R each 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 a cycloalkane, an aromatic hydrocarbon or an aromatic heterocycle, and the condensed 4 to 7 membered The ring may further have a substituent Z.
Z are each 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 '', and R '' Each 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.
(XY) represents a monoanionic bidentate ligand.
n _E6 represents an integer of 1 to 3) The method according to any one of claims 1 to 7,
The organic electroluminescent element containing the compound represented by the said General formula (1) in a light emitting layer. The method according to any one of claims 1 to 7,
The organic electroluminescent element which contains the compound represented by the said General formula (1) in the organic layer between a light emitting layer and a cathode, and adjacent to a light emitting layer. The light-emitting device containing the organic electroluminescent element in any one of Claims 1-9. The display device containing the organic electroluminescent element in 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).
[Chemical Formula 6]

(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 them. P is 0 ~ represents the four integer, q is an integer of 0 to 5. However, p + q is 1 is an integer equal to or greater than. R, if _a and R _B with a plurality exist, _B a plurality of R _a and R are different may be the same respectively may be 2 or more R _B are bonded to each other, together with the benzene ring B, fluorene, and form a ring, a naphthalene ring, or a phenanthrene ring, and fluorene ring, naphthalene ring or phenanthrene ring is an alkyl group, It may have a phenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a silyl group, a fluorine atom, or a group formed by combining them, provided that R _B does not form a condensation with the benzene ring A).

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