KR20130057476A - Organic electroluminescent element and charge transport material - Google Patents

Abstract

To provide an organic electroluminescent element having excellent luminous efficiency and durability, low driving voltage and excellent heat resistance. 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, the organic light emitting device having at least one of the organic layers, for example, An organic electroluminescent device comprising a compound having an aromatic 6-membered ring at a specific position in the phenylene skeleton and substituted with a sp ³ carbon-containing condensed ring group at a meta position relative to the triphenylene of the aromatic 6-membered ring.

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 light emission is obtained by low voltage driving. An organic electroluminescent element has an organic layer between a pair of electrodes, and uses the energy of the excitons produced | generated by recombination of the electron injected from the cathode and the hole injected from the anode in an organic layer.

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.

The development of the host material used for a light emitting layer and the charge transport material contained in another organic layer is also actively performed.

For example, Patent Document 1 describes a benzene ring substituted with triphenylene, such as a compound represented by the following ref-1, ref-2, and ref-3, with a benzene ring at a meta position relative to the triphenylene. The organic electroluminescent element containing the triphenylene compound which has a substituent which consists of is described.

[Formula 1]

In addition, Patent Document 2 describes an organic electroluminescent device containing a compound in which an fluorene ring is substituted with an anthracene ring substituted with triphenylene, such as the compound represented by the following ref-4.

[Formula 2]

Moreover, the patent documents 3-5 also describe the organic electroluminescent element containing the compound which has a triphenylene structure and a fluorene structure.

International Publication No. 09/021107 International Publication No. 09/066809 Japanese Unexamined Patent Publication No. 2004-43349 Japanese Unexamined Patent Publication No. 2004-83481 Japanese Unexamined Patent Publication No. 2009-114068

However, according to the examination of the present inventors, it turned out that the luminous efficiency after storing at the high temperature of the organic electroluminescent element using the compound which has the triphenylene structure of patent document 1 falls remarkably. In addition, triphenyl organic light emitting device using a compound having an alkylene structure described in Patent Document 2 to 5, the trend is the luminous efficiency after storage at a high temperature to be lowered is small, lowest here smaller the triplet (T ₁₎ Energy Therefore, it turned out that light emission is quenched and it becomes low efficiency especially when it uses for a phosphorescent element. For applications exposed to high temperatures, such as outdoor applications and automotive applications, organic electroluminescent devices that exhibit high efficiency even after high temperature storage are desired.

An object of the present invention is to provide an organic electroluminescent device having excellent luminous efficiency and durability, low driving voltage and excellent heat resistance.

Another object of the present invention is to provide a compound and a charge transport material which can be provided to an organic electroluminescent device having excellent luminous efficiency and durability, low driving voltage and excellent heat resistance.

According to the studies of the present inventors, the following general formula (1) and the like, triphenylamine having an aromatic 6-membered ring to a location of the alkylene skeleton, an sp ³ carbon atom in the meta position with respect to the triphenylene of the aromatic 6-membered ring Obtained by removing one hydrogen atom from a group having a condensed ring in which at least one ring selected from the group consisting of a 5- or 6-membered ring containing, an aromatic hydrocarbon ring consisting of only a single ring and an aromatic heterocyclic ring consisting of only a single ring is obtained It was found that the above problems can be solved by a compound in which a monovalent group (hereinafter also referred to as a "sp ³ carbon-containing condensed ring group") is substituted.

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 device containing a compound.

(3)

(In formula (1),

R _S1 represents a group represented by the following General Formula (S1).

[Formula 4]

X ¹ , X ² , X ³ , and X ⁴ each independently represent a carbon atom or a nitrogen atom.

L ¹ represents a linking group composed of at least one ring selected from the group consisting of a single bond or an aromatic hydrocarbon ring consisting of only a single ring and an aromatic hetero ring consisting of only a single ring. The linking group may have a substituent selected from the following substituent group W.

A ¹ is one hydrogen from a condensed ring in which a condensed ring is condensed by a 5- or 6-membered ring containing a sp ³ carbon atom, at least one ring selected from the group consisting of a monocyclic aromatic hydrocarbon ring and a monocyclic aromatic heterocyclic ring; The monovalent group obtained by removing an atom is shown. The monovalent group may have a substituent selected from the following substituent group W.

R _A , R _B , and R _C are each independently an alkyl group, a cycloalkyl group, an aryl group consisting of only a ^single ring, a heteroaryl group consisting only of a single ring, a cyano group, a halogen atom, a condensed ring group represented by A ¹ , and a combination thereof The group obtained is shown. When two or more R _<A> , R <_B> and R <_C> exist, they may mutually be same or different, but R _<A> and R <_B> do not become a group which has the same structure as R <_S1> together. a1 and b1 respectively independently represent the integer of 0-4. c1 represents the integer of 0-3.

R _D represents a substituent selected from the following substituent group W. When two or more R <_D> exists, they may mutually be same or different. d1 represents the integer of 0-4.

In X ¹ , X ² , X ³ , and X ⁴ , the carbon atom not bonded to R _D represents = CH—.

Substituent Group W: alkyl group, a cycloalkyl group, an aryl group containing only a single ring, a condensed ring group represented by a heteroaryl group, a silyl group, a cyano group, a fluorine atom, wherein A ¹ containing only a single ring, and which is obtained by a combination of these)

[2]

To the condensed ring in the above-mentioned A ¹ according to the above [1] represented by the general formula (A-1), (A -2), (A-3), (A-4), or (A-5) Organic electroluminescent device.

[Chemical Formula 5]

(In general formula (A-1), (A-2), (A-3), (A-4), and (A-5),

X ^a , X ^b , X ^c , X ^d , X ^e , X ^f , X ^g , and X ^h each independently represent C (Rb ₂₅ ) or a nitrogen atom.

Y ¹ , Y ² , Y ³ , Y ⁴ , and Y ⁵ are each independently C (Ra ₁₅ ) (Ra ₁₆ ), oxygen atom, sulfur atom, N (Ra ₁₇ ), Si (Ra ₁₈ ) (Ra ₁₉ ) , C = 0, P (= 0) (Rb ₂₆ ), or S (= 0) ₂ .

Ra ₁ to Ra ₁₉ each independently represent a hydrogen atom or a substituent selected from the following substituent group W ^A.

Rb ₁ to Rb ₂₆ each independently represent a hydrogen atom or a substituent selected from the following substituent group W.

Two neighboring ones of Ra ₁ to Ra ₁₉ and Rb ₁ to Rb _{26 may} combine to form a ring having an sp ³ carbon atom.

Substituent group W ^A : An aryl group which consists only of an alkyl group and a monocyclic ring, and the group which the substituent selected from the following substituent group W couple | bonded with these.

Substituent group W: an alkyl group, an aryl group consisting of only a ^single ring, a heteroaryl group consisting only of a single ring, a silyl group, a cyano group, a fluorine atom, a condensed ring group represented by the above-mentioned A ¹ , and a group obtained by combining them)

[3]

The organic electroluminescent device according to the above [1] or [2], wherein L ¹ is represented by the following General Formula (L-1).

[Formula 6]

(In general formula (L-1), X _L represents C (Rb ₂₇ ) or a nitrogen atom. R _L represents a substituent selected from the following substituent group W. When a plurality of R _L are present, they may be the same as each other. Rb ₂₇ represents a hydrogen atom or a substituent selected from the following substituent group W. When a plurality of Rb _{27 's} are present, they may be the same as or different from each other, L1 represents an integer of 0 to 4. L2 represents 0 The integer of-3. When L2 is 0, general formula (L-1) represents a single bond * represents a coupling site.

Substituent Group W: alkyl group, a cycloalkyl group, a condensed ring group represented by A ¹ in the aryl group consisting of only a single ring, a heteroaryl group, a silyl group, a cyano group, a fluorine atom containing only a single ring, the general formula (1), and these Group obtained by combining)

[4]

The organic electroluminescent element as described in any one of said [1]-[3] in which the compound represented by the said General formula (1) is represented by following General formula (2) or (3).

[Formula 7]

(In formula (2),

R _S2 represents a group represented by the following General Formula (S2).

[Formula 8]

R _A , R _B , and R _C each independently represent an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a cyano group, or a halogen atom. When two or more R _<A> , R <_B> and R <_C> exist, they may mutually be same or different, but R _<A> and R <_B> do not become a group which has the same structure as R <_S2> together. a1 and b1 respectively independently represent the integer of 0-4. c1 represents the integer of 0-3.

R _D represents a substituent selected from the following substituent group W. When two or more R <_D> exists, they may mutually be same or different. d1 represents the integer of 0-4.

R _L represents a substituent selected from the following substituent group W. When two or more R <_L> exists, they may mutually be same or different. L1 represents the integer of 0-4.

L2 represents the integer of 0-3.

Ra ₁ and Ra ₂ each independently represent a hydrogen atom or a substituent selected from the following substituent group W ^A. When two or more Ra <_1> and Ra <_2> exist, they may mutually be same or different.

R _b represents a substituent selected from the following substituent group W. When two or more R <_b> exists, they may mutually be same or different. b2 represents the integer of 0-4. b3 represents the integer of 0-3.

n2 represents 1 or 2.

_Two neighboring ones of Ra ₁ , Ra _2, and R _{b may be} bonded to form a ring having an sp ³ carbon atom.

Substituent group W ^A : An aryl group which consists only of an alkyl group and a monocyclic ring, and the group which the substituent selected from the following substituent group W couple | bonded with these.

Substituent Group W: alkyl group, a cycloalkyl group, an aryl group containing only a single ring, a condensed ring group represented by a heteroaryl group, a silyl group, a cyano group, a fluorine atom, wherein A ¹ containing only a single ring, and which is obtained by a combination of these)

[Chemical Formula 9]

(In formula (3),

R _S3 represents a group represented by the following General Formula (S3).

[Formula 10]

R _A , R _B , and R _C each independently represent an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a cyano group, or a halogen atom. When two or more R _<A> , R <_B> and R <_C> exist, they may mutually be same or different, but R _<A> and R <_B> do not become a group which has the same structure as R <_S3> together. a1 and b1 respectively independently represent the integer of 0-4. c1 represents the integer of 0-3.

R _D represents a substituent selected from the following substituent group W. When two or more R <_D> exists, they may mutually be same or different. d1 represents the integer of 0-4.

R _L represents a substituent selected from the following substituent group W. When two or more R <_L> exists, they may mutually be same or different. L1 represents the integer of 0-4.

L2 represents the integer of 0-3.

Ra represents a hydrogen atom or a substituent selected from the following substituent group W ^A. Ra may be mutually same or different.

R _b represents a substituent selected from the following substituent group W. When two or more R <_b> exists, they may mutually be same or different. b3 represents the integer of 0-3.

n3 represents 1 or 2.

Two neighboring ones of Ra and R _{b may} combine to form a ring having an sp ³ carbon atom.

Substituent Group W ^A : An alkyl group, an aryl group consisting of only a single ring, and a group having a substituent selected from the following substituent group W bonded thereto.

Substituent Group W: alkyl group, a cycloalkyl group, a condensed ring group represented by A ¹ in the aryl group consisting of only a single ring, a heteroaryl group, a silyl group, a cyano group, a fluorine atom containing only a single ring, the general formula (1), and these Group obtained by combining)

[5]

The organic electroluminescent element according to any one of the above [1] to [4], wherein the light emitting layer contains at least one phosphorescent material.

[6]

The organic electroluminescent device according to the above [5], wherein the phosphorescent material is represented by the following General Formula (E-1).

[Formula 11]

(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 which 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)

[7]

The organic electroluminescent element as described in said [6] whose phosphorescent material represented by said general formula (E-1) is represented with the following general formula (E-2).

[Chemical Formula 12]

(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.

n _E2 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 a hole block layer.

[10]

The organic electroluminescent element according to any one of the above [1] to [9], wherein at least one organic layer is formed by a solution coating method.

[11]

The organic electroluminescent element as described in any one of said [1]-[10] manufactured by forming into a film the organic layer containing the compound represented by the said General formula (1) by the solution coating method.

[12]

The light emitting device using the organic electroluminescent element in any one of said [1]-[11].

[13]

The display apparatus using the organic electroluminescent element in any one of said [1]-[11].

[14]

The illuminating device using the organic electroluminescent element in any one of said [1]-[11].

[15]

The charge transport material represented by the said General formula (1), (2), or (3) in any one of said [1]-[4].

[16]

The compound represented by the said General formula (1), (2) or (3) in any one of said [1]-[4].

According to the present invention, it is possible to provide an organic electroluminescent element having excellent luminous efficiency and durability, low driving voltage and excellent heat resistance.

Moreover, according to this invention, the compound and charge transport material which can be provided to the organic electroluminescent element which have the outstanding luminous efficiency, durability, low drive voltage, and excellent heat resistance 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)

(Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, t-butyl, n- , an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as methyl, ethyl, n-propyl, , An alkynyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 carbon atoms, such as vinyl, allyl, 2-butenyl and 3-pentenyl) (Preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms), an aryl group (preferably having 1 to 10 carbon atoms, such as propargyl and 3-pentynyl) For example, phenyl, p-methylphenyl, naphthyl, anthranyl, etc. ), 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 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 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, for example, phenyloxycarbonylamino, etc.), 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 Diary (preferably 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 12 carbon atoms, and examples thereof include sulfamoyl, methyl sulfamoyl, dimethyl sulfamoyl, and phenyl sulfamoyl). 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 ( Preferably it is C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, pyridylthio, 2-benzimizolylthio, 2-benzoxazolylthio, 2- Benzthiazolylthio, etc.), sulfonyl group (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, mesyl, tosyl, etc. are mentioned. Sulfinyl group (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, methanesulfinyl, benzenesulfinyl, etc. are mentioned). , 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 groups (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, 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 heterocyclic ring) It also contains carbon, 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, tier Neil, Sele Phenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, benzoimidazolyl, benzothiazolyl, carbazolyl group, azepinyl group, silolyl group Etc.), a silyl group (preferably C3-C40, More preferably, it is C3-C30, Especially preferably, it is C3-C24, For example, 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, triphenylsilyloxy, etc. are mentioned. ) And a phosphoryl group (for example, diphenylphosphoryl group, dimethylphosphoryl group, etc. may be mentioned). These substituents may further be substituted and the group selected from the substituent group A demonstrated above as a further substituent is mentioned. Moreover, 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. Moreover, the substituent substituted by 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.

(Substituent group B)

(Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, t-butyl, n- , an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as methyl, ethyl, n-propyl, , An alkynyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 carbon atoms, such as vinyl, allyl, 2-butenyl and 3-pentenyl) (Preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms), an aryl group (preferably having 1 to 10 carbon atoms, such as propargyl and 3-pentynyl) For example, phenyl, p-methylphenyl, naphthyl, anthranyl, etc. ), Cyano group, heterocyclic group (aromatic heterocyclic group is also included, and preferably has 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, isoxa Zolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzooxazolyl, benzoimidazolyl And benzothiazolyl, carbazolyl group, azepinyl group, silolyl group, etc.) These substituents may be further substituted, and the group selected from the said substituent group B is mentioned further as a substituent. Moreover, 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. Moreover, the substituent substituted by 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.

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 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 present. It contains the compound represented by following General formula (1).

[Chemical Formula 13]

(In formula (1),

R _S1 represents a group represented by the following General Formula (S1).

[Formula 14]

X ¹ , X ² , X ³ , and X ⁴ each independently represent a carbon atom or a nitrogen atom.

L ¹ represents a linking group composed of at least one ring selected from the group consisting of a single bond or an aromatic hydrocarbon ring consisting of only a single ring and an aromatic hetero ring consisting of only a single ring. The linking group may have a substituent selected from the following substituent group W.

A ¹ is one hydrogen from a condensed ring in which a condensed ring is condensed by a 5- or 6-membered ring containing a sp ³ carbon atom, at least one ring selected from the group consisting of a monocyclic aromatic hydrocarbon ring and a monocyclic aromatic heterocyclic ring; The monovalent group obtained by removing an atom is shown. The monovalent group may have a substituent selected from the following substituent group W.

R _A , R _B , and R _C are each independently an alkyl group, a cycloalkyl group, an aryl group consisting of only a ^single ring, a heteroaryl group consisting only of a single ring, a cyano group, a halogen atom, a condensed ring group represented by A ¹ , and a combination thereof The group obtained is shown. When two or more R _<A> , R <_B> and R <_C> exist, they may mutually be same or different, but R _<A> and R <_B> do not become a group which has the same structure as R <_S1> together. a1 and b1 respectively independently represent the integer of 0-4. c1 represents the integer of 0-3.

R _D represents a substituent selected from the following substituent group W. When two or more R <_D> exists, they may mutually be same or different. d1 represents the integer of 0-4.

In X ¹ , X ² , X ³ , and X ⁴ , the carbon atom not bonded to R _D represents = CH—.

Substituent Group W: alkyl group, a cycloalkyl group, an aryl group containing only a single ring, a condensed ring group represented by a heteroaryl group, a silyl group, a cyano group, a fluorine atom, wherein A ¹ containing only a single ring, and which is obtained by a combination of these)

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

Generally, it is known that the molecular weight of a compound increases, Tg rises, and heat resistance improves by introducing a condensed ring structure into the compound.

However, according to the studies by the present inventors, when a compound having a triphenylene skeleton is introduced as a substituent by introducing a condensed ring having an aromatic hydrocarbon ring such as a naphthalene ring, an anthracene ring, a quinoline ring or two or more aromatic hetero rings as a substituent, improved, but, T _1, and the energy is greatly reduced, especially in the device using the phosphorescent material was found to result in greater efficiency.

Further, the result of the present inventors conducted the intensive studies, as a compound represented by the general formula (1), the triphenylene skeleton and the sp ³ groups carbon-containing fused ring with an aromatic 6-membered ring compound having a structure connected in the meta-position is without lowering the T ₁ energy was found that to improve the heat resistance. This is thought to be because the? Conjugated system is broken at the sp ³ carbon atom of the sp ³ carbon-containing condensed ring group, so that the T ₁ energy does not decrease.

Therefore, by using the compound represented by General formula (1), the element excellent in all the viewpoints of efficiency, drive voltage, drive durability, and heat resistance can be obtained.

In a compound represented by the general formula (1), film state T ₁ energy, 2.39 eV (55 ㎉ / ㏖ ) more than 3.25 eV (75 ㎉ / ㏖) is preferably, 2.47 eV (57.0 ㎉ / ㏖ ) more than 3.04 or less It is more preferable that it is eV (70 dl / mol) or less, and it is still more preferable that it is 2.52 eV (58.0 dl / mol) or more and 2.82 eV (65 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 General formula (1) is demonstrated.

[Formula 15]

(In formula (1),

R _S1 represents a group represented by the following General Formula (S1))

[Chemical Formula 16]

X ¹ , X ² , X ³ , and X ⁴ each independently represent a carbon atom or a nitrogen atom.

L ¹ represents a linking group composed of at least one ring selected from the group consisting of a single bond or an aromatic hydrocarbon ring consisting of only a single ring and an aromatic hetero ring consisting of only a single ring. The linking group may have a substituent selected from the following substituent group W.

A ¹ is one hydrogen from a condensed ring in which a condensed ring is condensed by a 5- or 6-membered ring containing a sp ³ carbon atom, at least one ring selected from the group consisting of a monocyclic aromatic hydrocarbon ring and a monocyclic aromatic heterocyclic ring; The monovalent group obtained by removing an atom is shown. The monovalent group may have a substituent selected from the following substituent group W.

R _A , R _B , and R _C are each independently an alkyl group, a cycloalkyl group, an aryl group consisting of only a ^single ring, a heteroaryl group consisting only of a single ring, a cyano group, a halogen atom, a condensed ring group represented by A ¹ , and a combination thereof The group obtained is shown. When two or more R _<A> , R <_B> and R <_C> exist, they may mutually be same or different, but R _<A> and R <_B> do not become a group which has the same structure as R <_S1> together. a1 and b1 respectively independently represent the integer of 0-4. c1 represents the integer of 0-3.

R _D represents a substituent selected from the following substituent group W. When two or more R <_D> exists, they may mutually be same or different. d1 represents the integer of 0-4.

In X ¹ , X ² , X ³ , and X ⁴ , the carbon atom not bonded to R _D represents = CH—.

Substituent Group W: alkyl group, a cycloalkyl group, an aryl group containing only a single ring, a condensed ring group represented by a heteroaryl group, a silyl group, a cyano group, a fluorine atom, wherein A ¹ containing only a single ring, and which is obtained by a combination of these)

That is, the compound represented by General formula (1) can also be represented by following General formula (1) '.

[Chemical Formula 17]

In General Formula (1) ', X ¹ , X ² , X ³ , X ⁴ , R _A , R _B , R _C , a1, b1, c1, R _D , d1, L ¹ , A ¹ represents the above general formula ( It is synonymous with 1), and its preferable range is also the same.

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.

Substituent group W consists of an alkyl group, a cycloalkyl group, the aryl group consisting only of a monocyclic ring, the heteroaryl group consisting only of a monocyclic ring, a silyl group, the cyano group, the fluorine atom, the condensed ring group represented by A <^1> , and the group obtained by combining these.

As an alkyl group, Preferably it is C1-C10, More preferably, it is C1-C6, More preferably, it is a C1-C4 alkyl group. 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, n-propyl group, n-butyl group, or t-butyl group is more preferable.

As a cycloalkyl group, Preferably it is a C3-C10, More preferably, it is a C4-C6, More preferably, it is a C5-C6 cycloalkyl group. Cyclopentyl group and cyclohexyl group are preferable.

As an aryl group which consists only of a ring, a phenyl group is preferable.

As a heteroaryl group which consists only of a monocyclic ring, the heteroaryl group which consists only of nitrogen-containing or sulfur-containing monocyclic groups is preferable, a pyridyl group, a pyrazyl group, a pyrimidyl group, or a thiophenyl group is more preferable, and a pyridyl group is more preferable.

Specific examples and preferable range of the condensed ring group represented by A ¹ is the same as A ^1, which will be described later.

Examples of the group obtained by combining them include an alkyl group substituted with an aryl group, an aryl group substituted with an alkyl group, an alkyl group or a silyl group substituted with an aryl group (preferably trimethylsilyl group or triphenylsilyl group), and a fluoroalkyl group (preferably purple) A fluoroalkyl group, More preferably, a trifluoromethyl group), the group represented by the following general formula (Arx), etc. are mentioned.

[Chemical Formula 18]

(In General Formula (Arx), Ara to Ard each independently represent an aromatic hydrocarbon ring composed of only a single ring, an aromatic heterocyclic ring composed of only a single ring, or a condensed ring represented by A ^1. Na and nb each independently represent 0 or 1 represents nc and nd represents 1. When na and nb are 0, Ara and Arb represent a single bond Ara to Ard each independently represent an alkyl group, an aryl group consisting of only a single ring, and a heteroaryl group consisting of only a single ring , Silyl group, cyano group, fluorine atom, or condensed ring group represented by A ¹ may be substituted.

In general formula (Arx), as an aromatic hydrocarbon ring which consists only of a monocyclic ring, a benzene ring is preferable. As an aromatic heterocyclic ring which consists only of a ring, a nitrogen-containing aromatic heterocycle or a sulfur-containing aromatic heterocycle is preferable, and a nitrogen-containing aromatic heterocycle is more preferable. As a nitrogen-containing aromatic heterocycle, a pyridine ring, a pyrazine ring, a pyrimidine ring is preferable, and a pyridine ring is more preferable. As a sulfur-containing aromatic heterocycle, a thiophene ring is preferable. Specific examples and preferred ranges of the condensed ring represented by A ¹ are the same as those described later.

Preferable ranges of the alkyl group which may be substituted by Ara to Ard, the aryl group consisting of only a ^single ring, the heteroaryl group consisting only of a single ring, and the condensed ring group represented by A ¹ are the same as those mentioned above.

From the viewpoint of charge transportability and chemical stability, na and nb are preferably 0.

Formula (1) of, A ¹ is at least one ring selected from the group consisting of an aromatic heterocyclic ring composed of only an aromatic hydrocarbon ring and a single ring containing only 5 atom or 6 atom rings, a single ring containing a sp ³ carbon atoms condensed The monovalent group obtained by removing one hydrogen atom from the condensed ring thus obtained is shown. The monovalent group may have a substituent selected from the substituent group W.

When triphenylene is introduced as a substituent, a condensed ring of two or more aromatic hydrocarbon rings or aromatic hetero rings such as naphthalene ring, anthracene ring and quinoline ring is introduced as a substituent, but the heat resistance is improved, but the T ₁ energy is greatly reduced, Especially in the element using a phosphorescence emitting material, a big efficiency fall is caused. In contrast, A ¹ in General Formula (1) of the present invention is a group consisting of a 5-membered or 6-membered ring containing an sp ³ carbon atom, an aromatic hydrocarbon ring composed of only a single ring, and an aromatic heterocyclic ring composed of only a single ring. Since at least one ring selected is composed of a condensed ring condensed, it is thought that the? Conjugated system is broken at sp ³ carbon atoms, the T ₁ energy is not lowered and the heat resistance is also improved.

As a 5 or 6-membered ring containing sp ³ carbon atom in A ¹ , a saturated 5 or 6-membered ring is preferable, and a cyclopentane ring, a cyclohexane ring, or at least one hetero atom is contained. A saturated five-membered or six-membered ring is more preferable, a cyclopentane ring or a cyclohexane ring is more preferable, and a cyclopentane ring is particularly preferable.

As said hetero atom, an oxygen atom, a sulfur atom, a nitrogen atom, a silicon atom, or a phosphorus atom is preferable, an oxygen atom, a sulfur atom, or a nitrogen atom is more preferable, and an oxygen atom or a nitrogen atom is further more preferable.

As a saturated 5 or 6-membered ring containing a nitrogen atom, a piperidine ring, a piperazine ring, a pyrrolidine ring are preferable, a piperidine ring and a piperazine ring are more preferable, and a piperidine ring More preferred.

As a saturated 5 or 6-membered ring containing an oxygen atom, a tetrahydropyran ring, a dioxane ring, a tetrahydrofuran ring, a 1,3-dioxolane ring is preferable, and a dioxane ring, 1,3- Dioxolane rings are more preferred.

As a saturated 5 or 6-membered ring containing a sulfur atom, a 1, 4- dithiane ring and a tetrahydrothiophene ring are preferable, and a 1, 4- dithiane ring is more preferable.

Moreover, the 5-membered or 6-membered ring containing the sp ³ carbon atom in A ¹ may contain a carbonyl group, a sulfonyl group, or a phosphoric acid group.

When A <^1> contains the aromatic hydrocarbon ring which consists only of a single ring, a benzene ring is preferable as an aromatic hydrocarbon ring which consists only of that single ring.

When A <^1> contains the aromatic heterocyclic ring which consists only of a monocyclic ring, as an aromatic heterocyclic ring which consists only of this monocyclic ring, a nitrogen-containing aromatic heterocyclic ring or a sulfur-containing aromatic heterocyclic ring is preferable, and a nitrogen-containing aromatic heterocyclic ring is more preferable. As a nitrogen-containing aromatic heterocycle, a pyridine ring, a pyrazine ring, a pyrimidine ring, and a triazine ring are preferable, and a pyridine ring is more preferable. As a sulfur-containing aromatic heterocycle, a thiophene ring is preferable.

A condensed ring at the A ¹ is a ring represented by the following general formula (A-1), (A -2), (A-3), (A-4), or (A-5) are preferred.

[Chemical Formula 19]

(In general formula (A-1), (A-2), (A-3), (A-4), and (A-5),

X ^a , X ^b , X ^c , X ^d , X ^e , X ^f , X ^g , and X ^h each independently represent C (Rb ₂₅ ) or a nitrogen atom.

Y ¹ , Y ² , Y ³ , Y ⁴ , and Y ⁵ are each independently C (Ra ₁₅ ) (Ra ₁₆ ), oxygen atom, sulfur atom, N (Ra ₁₇ ), Si (Ra ₁₈ ) (Ra ₁₉ ) , C = 0, P (= 0) (Rb ₂₆ ), or S (= 0) ₂ .

Ra ₁ to Ra ₁₉ each independently represent a hydrogen atom or a substituent selected from the following substituent group W ^A.

Rb ₁ to Rb ₂₆ each independently represent a hydrogen atom or a substituent selected from the following substituent group W.

Two neighboring ones of Ra ₁ to Ra ₁₉ and Rb ₁ to Rb _{26 may} combine to form a ring having an sp ³ carbon atom.

Substituent group W ^A : An aryl group which consists only of an alkyl group and a monocyclic ring, and the group which the substituent selected from the following substituent group W couple | bonded with these.

Substituent Group W: alkyl group, a cycloalkyl group, an aryl group containing only a single ring, a condensed ring group represented by a heteroaryl group, a silyl group, a cyano group, a fluorine atom, wherein A ¹ containing only a single ring, and which is obtained by a combination of these)

In General Formula (A-1), Ra ₁ and Ra ₂ each independently represent a substituent selected from a hydrogen atom or a substituent group W ^A.

As Ra ₁ and Ra ₂ , an aryl group composed of only a hydrogen atom, an alkyl group, or a single ring is preferable, and an alkyl group is more preferable from the viewpoint of charge transportability and chemical stability. As an alkyl group, a C1-C10 alkyl group is preferable, A C1-C5 alkyl group is more preferable, A methyl group, an ethyl group, n-propyl group, or n-butyl group is more preferable, A methyl group is especially preferable. As an aryl group which consists only of a ring, a phenyl group is preferable.

Moreover, it is also preferable that Ra <_1> and Ra <_2> combine with each other, and the ring represented by general formula (A-1) forms a spirobifluorene ring.

In General Formula (A-1), Rb ₁ to Rb ₈ each independently represent a substituent selected from a hydrogen atom or a substituent group W.

Rb ₁ to Rb ₈ are preferably an aryl group consisting of only a hydrogen atom, an alkyl group, or a single ring from the viewpoint of charge transportability and chemical stability, more preferably a hydrogen atom or an alkyl group, and even more preferably a hydrogen atom. As an alkyl group, a C1-C10 alkyl group is preferable, A C1-C5 alkyl group is more preferable, A t-butyl group is further more preferable. As an aryl group which consists only of a ring, a phenyl group is preferable.

_Two neighboring ones of Ra ₁ , Ra ₂ and Rb ₁ to Rb _{8 may} combine to form a ring having an sp ³ carbon atom. As the ring, a cycloalkane ring is preferable, a cycloalkane ring having 3 to 10 carbon atoms is more preferable, and a cyclohexane ring is more preferable. In the case of forming a ring, it is preferable that Ra ₂ and Rb ₈ combine with each other to form a ring having an sp ³ carbon atom.

A condensed ring represented by formula (A-1) is, Ra _1, Ra ₂ and Rb ₁ ~ Rb least either one is the a hydrogen atoms of the _8, is removed dog any one of the hydrogen atoms A in the general formula (1) ^Binds to L ¹ as ¹ ; From the viewpoint of charge transportability and chemical stability, it is particularly preferable that Rb ₁ to Rb ₈ are hydrogen atoms, and any one of the hydrogen atoms is removed and bonded to L ¹ as A ¹ in General Formula (1).

In General Formula (A-2), Ra ₃ to Ra ₆ each independently represent a substituent selected from a hydrogen atom or a substituent group W ^A.

From the viewpoint of charge transportability and chemical stability, Ra ₃ to Ra ₆ are preferably an aryl group consisting of only a hydrogen atom, an alkyl group, or a single ring, and more preferably a hydrogen atom. The preferable range of the alkyl group and the aryl group which consists only of a monocyclic ring is the same as the preferable range when Ra <_1> and Ra <_2> is an alkyl group or the aryl group which consists only of a monocyclic ring.

In General Formula (A-2), Rb ₉ to Rb ₁₆ each independently represent a substituent selected from a hydrogen atom or a substituent group W.

Rb Rb ~ ₉ to ₁₆ in terms of charge-and chemical stability, the aryl group preferably containing only a hydrogen atom, an alkyl group, or a single ring, more preferably a hydrogen atom. A preferred range of the aryl group containing only the alkyl group, and a single ring is the same as the preferable range in the case an aryl group is Rb Rb ~ _{1 8} comprising only alkyl groups, or single ring.

Two neighboring ones of Ra ₃ to Ra ₆ and Rb ₉ to Rb _{16 may} combine to form a ring having an sp ³ carbon atom. As the ring, a cycloalkane ring is preferable, a cycloalkane ring having 3 to 10 carbon atoms is more preferable, and a cyclohexane ring is more preferable. In the case of forming a ring, it is preferable that Rb ₁₂ and Rb ₁₃ combine with each other to form a ring having an sp ³ carbon atom.

In the condensed ring represented by General Formula (A-2), at least one of Ra ₃ to Ra ₆ and Rb ₉ to Rb ₁₆ represents a hydrogen atom, any one of the hydrogen atoms is removed, and A ¹ in General Formula (1) As L ¹ . From the viewpoint of charge transportability and chemical stability, in particular, Rb ₉ to Rb ₁₆ are preferably hydrogen atoms, and any one of the hydrogen atoms is removed to be bonded to L ¹ as A ¹ in General Formula (1).

In General Formula (A-3), Y ¹ and Y ² are each independently C (Ra ₁₅ ) (Ra ₁₆ ), oxygen atom, sulfur atom, N (Ra ₁₇ ), Si (Ra ₁₈ ) (Ra ₁₉ ), C = O, P (= 0) (Rb ₂₆ ), or S (= 0) ₂ . Ra ₁₅ to Ra ₁₉ each independently represent a substituent selected from a hydrogen atom or a substituent group W ^A.

As Ra <_15> and Ra <_16> , the aryl group which consists only of a hydrogen atom, an alkyl group, or a monocyclic ring is preferable, and it is more preferable that it is a hydrogen atom. The preferable range of the alkyl group and the aryl group which consists only of a monocyclic ring is the same as the preferable range when Ra <_1> and Ra <_2> is an alkyl group or the aryl group which consists only of a monocyclic ring.

As Ra <_17> , the aryl group which consists only of a hydrogen atom, an alkyl group, or a monocyclic ring is preferable, and the aryl group which consists only of a hydrogen atom or a monocyclic ring is more preferable. The preferable range of the alkyl group and the aryl group which consists only of a monocyclic ring is the same as the preferable range when Ra <_1> and Ra <_2> is an alkyl group or the aryl group which consists only of a monocyclic ring.

As Ra ₁₈ and Ra ₁₉ , an aryl group consisting of only a hydrogen atom, an alkyl group, or a monocyclic ring is preferable, and more preferably an alkyl group or an aryl group consisting of only a single ring. The preferable range of the alkyl group and the aryl group which consists only of a monocyclic ring is the same as the preferable range when Ra <_1> and Ra <_2> is an alkyl group or the aryl group which consists only of a monocyclic ring.

As Rb ₂₆ , an aryl group consisting of only a hydrogen atom, an alkyl group, or a single ring is preferable, and an aryl group consisting of only a single ring is more preferable. The preferable range of the alkyl group and the aryl group which consists only of a monocyclic ring is the same as the preferable range when Ra <_1> and Ra <_2> is an alkyl group or the aryl group which consists only of a monocyclic ring.

Y ¹ and Y ² are each independently C (Ra ₁₅ ) (Ra ₁₆ ), oxygen atom, sulfur atom, N (Ra ₁₇ ), or Si (Ra ₁₈ ) (Ra ₁₉ ) in terms of charge transportability and chemical stability. Preferably represents C (Ra ₁₅ ) (Ra ₁₆ ), an oxygen atom, or N (Ra ₁₇ ), more preferably represents C (Ra ₁₅ ) (Ra ₁₆ ), or an oxygen atom, More preferably, C (Ra ₁₅ ) (Ra ₁₆ ).

In General Formula (A-3), Ra ₇ to Ra ₁₀ each independently represent a substituent selected from a hydrogen atom or a substituent group W ^A.

From the viewpoint of charge transportability and chemical stability, Ra ₇ to Ra ₁₀ are preferably an aryl group consisting of only a hydrogen atom, an alkyl group, or a single ring, and more preferably a hydrogen atom. The preferable range of the alkyl group and the aryl group which consists only of a monocyclic ring is the same as the preferable range when Ra <_1> and Ra <_2> is an alkyl group or the aryl group which consists only of a monocyclic ring.

In General Formula (A-3), X ^a , X ^b , X ^c , and X ^d each independently represent C (Rb ₂₅ ) or a nitrogen atom.

In view of charge transportability and chemical stability, when X ^a represents ^a nitrogen atom, X ^b , X ^c , and X ^d each independently represent C (Rb ₂₅ ) (Rb ₂₆ ), and X ^a , X ^b , more preferably indicate the X ^c, and X ^d each independently represent C (Rb ₂₅₎ to a preferred, and X ^a, X ^b, X ^c, and X ^d each independently represent C (Rb ₂₅₎ indicate .

Rb ₂₅ each independently represents a substituent selected from a hydrogen atom or a substituent group W.

As Rb ₂₅ , from the viewpoint of charge transportability and chemical stability, an aryl group consisting of only a hydrogen atom, an alkyl group, or a monocyclic ring is preferable, and a hydrogen atom is more preferable. A preferred range of the aryl group containing only the alkyl group, and a single ring is the same as the preferable range in the case an aryl group is Rb Rb ~ _{1 8} comprising only alkyl groups, or single ring.

Two neighboring ones of Ra ₇ to Ra ₁₀ , Ra ₁₅ to Ra ₁₉ , Rb _25, and Rb _{26 may} combine to form a ring having an sp ³ carbon atom. As the ring, a cycloalkane ring is preferable, a cycloalkane ring having 3 to 10 carbon atoms is more preferable, and a cyclohexane ring is more preferable. In the case of forming a ring, it is preferable that Ra ₁₅ in Y ² and Rb ₂₅ in X ^d combine with each other to form a ring having an sp ³ carbon atom.

In the condensed ring represented by General Formula (A-3), at least any one of Ra ₇ to Ra ₁₀ , Ra ₁₅ to Ra ₁₉ , Rb _25, and Rb ₂₆ represents a hydrogen atom, and any one of the hydrogen atoms is removed to form a general formula. It binds to L <^1> as A <^1> in (1). In view of charge transportability and chemical stability, it is particularly preferable that Rb ₂₅ or Rb ₂₆ is a hydrogen atom, and any one of the hydrogen atoms is removed and bonded to L ¹ as A ¹ in General Formula (1).

In General Formula (A-4), Y ³ and Y ⁴ are each independently C (Ra ₁₅ ) (Ra ₁₆ ), oxygen atom, sulfur atom, N (Ra ₁₇ ), Si (Ra ₁₈ ) (Ra ₁₉ ), C = O, P (= 0) (Rb ₂₆ ), or S (= 0) ₂ . Ra ₁₅ to Ra ₁₉ each independently represent a substituent selected from a hydrogen atom or a substituent group W ^A.

The preferable ranges of Ra ₁₅ to Ra ₁₉ and (Rb ₂₆ ) are the same as those in the general formula (A-3).

Preferable ranges of Y ³ and Y ⁴ are the same as those of Y ¹ and Y ² in General Formula (A-3).

In General Formula (A-4), Ra ₁₁ and Ra ₁₂ each independently represent a substituent selected from a hydrogen atom or a substituent group W ^A.

Preferable ranges of Ra ₁₁ and Ra ₁₂ are the same as those of Ra ₇ to Ra ₁₀ in General Formula (A-3).

In general formula (A-4), X ^e , X ^f , X ^g , and X ^h each independently represent C (Rb ₂₅ ) or a nitrogen atom.

The preferable range of Rb ₂₅ is the same as that in the said general formula (A-3).

Preferable ranges of X ^e , X ^f , X ^g , and X ^h are the same as those of X ^a , X ^b , X ^c , and X ^d in the general formula (A-3).

Two neighboring ones of Ra ₁₁ , Ra ₁₂ , Ra ₁₅ to Ra ₁₉ , Rb _25, and Rb _{26 may} combine to form a ring having an sp ³ carbon atom. As the ring, a cycloalkane ring is preferable, a cycloalkane ring having 3 to 10 carbon atoms is more preferable, and a cyclohexane ring is more preferable. In the case of forming a ring, Ra ₁₅ in Y ⁴ and Rb ₂₅ in X ^h It is preferred if the two combine to form a ring having sp ³ carbon atoms.

As for the condensed ring represented by general formula (A-4), at least any one of Ra ₁₁ , Ra ₁₂ , Ra ₁₅ to Ra ₁₉ , Rb _25, and Rb ₂₆ represents a hydrogen atom, and any one of the hydrogen atoms is removed to form a general formula. It binds to L <^1> as A <^1> in (1). In view of charge transportability and chemical stability, it is particularly preferable that Rb ₂₅ or Rb ₂₆ is a hydrogen atom, and any one of the hydrogen atoms is removed and bonded to L ¹ as A ¹ in General Formula (1).

In General Formula (A-5), Y ⁵ is C (Ra ₁₅ ) (Ra ₁₆ ), oxygen atom, sulfur atom, N (Ra ₁₇ ), Si (Ra ₁₈ ) (Ra ₁₉ ), C═O, P ( = O) (Rb ₂₆ ), or S (= O) ₂ . Ra ₁₅ to Ra ₁₉ each independently represent a substituent selected from a hydrogen atom or a substituent group W ^A.

The preferable ranges of Ra ₁₅ to Ra ₁₉ and (Rb ₂₆ ) are the same as those in the general formula (A-3).

Y ^{5 preferably} represents C (Ra ₁₅ ) (Ra ₁₆ ), an oxygen atom, or N (Ra ₁₇ ), more preferably C (Ra ₁₅ ) (Ra ₁₆ ), or N (Ra ₁₇ ). It is more preferable to represent N (Ra ₁₇ ).

In General Formula (A-5), Ra ₁₃ and Ra ₁₄ each independently represent a substituent selected from a hydrogen atom or a substituent group W ^A.

Preferable ranges of Ra ₁₃ and Ra ₁₄ are the same as those of Ra ₇ to Ra ₁₀ in General Formula (A-3).

In General Formula (A-5), Rb ₁₇ to Rb ₂₄ each independently represent a substituent selected from a hydrogen atom or a substituent group W.

The preferable ranges of Rb ₁₇ to Rb ₂₄ are the same as those of Rb ₁ to Rb _{8 in} General Formula (A-1).

Two neighboring ones of Ra ₁₃ to Ra ₁₉ and Rb ₁₇ to Rb _{26 may} combine to form a ring having an sp ³ carbon atom. As the ring, a cycloalkane ring is preferable, a cycloalkane ring having 3 to 10 carbon atoms is more preferable, and a cyclohexane ring is more preferable. In the case of forming a ring, it is preferable that Ra ₁₃ and Ra ₁₄ combine with each other to form a ring having an sp ³ carbon atom.

In the condensed ring represented by General Formula (A-5), at least any one of Ra ₁₃ to Ra ₁₉ and Rb ₁₇ to Rb ₂₆ represents a hydrogen atom, and any one of the hydrogen atoms is removed to remove A ¹ in General Formula (1). As L ¹ . From the viewpoint of charge transportability and chemical stability, it is particularly preferable that Ra ₁₇ is a hydrogen atom, and the hydrogen atom is removed to bond to L ¹ as A ¹ in General Formula (1). In addition, from the viewpoint of charge transportability and chemical stability, in particular, Rb ₁₇ to Rb ₂₄ are preferably hydrogen atoms, and any one of the hydrogen atoms is removed to be bonded to L ¹ as A ¹ in General Formula (1).

As a condensed ring in A <^1> , the ring represented by the said general formula (A-1) or (A-4) is especially preferable from a viewpoint of charge transport property and chemical stability.

It represents a specific example of the condensed ring in the examples below, not limited to those of the A ^1. In addition, the following specific example may have a substituent selected from the substituent group W as mentioned above.

[Chemical Formula 20]

In said structural formula, R represents a hydrogen atom, an alkyl group, or an aryl group. Preferable ranges of the alkyl group and the aryl group are the same as those of the substituent group W.

In General Formula (1), L ¹ represents a linking group composed of at least one ring selected from the group consisting of a single bond or an aromatic hydrocarbon ring consisting of only a single ring and an aromatic hetero ring consisting of only a single ring. As an aromatic hydrocarbon ring which consists only of the said ring, a benzene ring is preferable. As an aromatic heterocyclic ring which consists only of the said ring, a nitrogen-containing heterocyclic ring is preferable, A pyridine ring, a pyrazine ring, a pyrimidine ring, and a triazine ring are more preferable, and pyridine is more preferable.

L ¹ is preferably represented by the following General Formula (L-1).

[Chemical Formula 21]

(In General Formula (L-1), X _L represents C (Rb ₂₇ ) and a nitrogen atom. R _L represents a substituent selected from the following substituent group W. When a plurality of R _L are present, they may be the same or different. Rb ₂₇ represents a hydrogen atom or a substituent selected from the following substituent group W. When a plurality of Rb _{27 's} are present, they may be the same as or different from each other, L1 represents an integer of 0 to 4. L2 represents 0 to 3 When L2 is 0, general formula (L-1) represents a single bond * represents a binding site.

Substituent Group W: alkyl group, a cycloalkyl group, a condensed ring group represented by A ¹ in the aryl group consisting of only a single ring, a heteroaryl group, a silyl group, a cyano group, a fluorine atom containing only a single ring, the general formula (1), and these Group obtained by combining)

In General Formula (L-1), X _L represents C (Rb ₂₇ ) or a nitrogen atom, and C (Rb ₂₇ ) is preferable from the viewpoint of charge transportability and chemical stability.

Rb ₂₇ represents a hydrogen atom or a substituent selected from the following substituent group W. Rb ₂₇ is even if there are a plurality may be the same different from each other. As Rb ₂₇ , from the viewpoint of charge transportability and chemical stability, an aryl group consisting of only a hydrogen atom, an alkyl group, or a monocyclic ring is preferable, and a hydrogen atom is more preferable. A preferred range of the aryl group containing only the alkyl group, and a single ring is the same as the preferable range of the Rb Rb ~ _{1 8} are aryl groups composed of only an alkyl group, or monocyclic case.

In General Formula (L-1), R _L represents a substituent selected from a substituent group W.

From the viewpoint of charge transportability and chemical stability, R _L is preferably an alkyl group, an aryl group consisting of only a single ring, a silyl group, a condensed ring group represented by A ¹ , and a group obtained by combining them, and an alkyl group, an aryl group consisting of only a single ring, and A ^1. composed of only the condensed ring group is a substituted single ring represented by an aryl group, a condensed ring group represented by a silyl group, a ^{1-substituted} alkyl groups, and groups condensed rings and more preferably represented by a ¹ the alkyl group is optionally substituted, represents an alkyl group, or a ¹ More preferred is a phenyl group substituted with a condensed ring group.

In General Formula (L-1), L1 represents the integer of 0-4, From an viewpoint of charge transportability and chemical stability, the integer of 0-2 is preferable, 0 or 1 is more preferable, and 0 is still more preferable. .

In general formula (L-1), L2 represents the integer of 0-3, and the integer of 0-2 is preferable from a viewpoint of charge transportability and chemical stability.

L ¹ is preferably connected at the meta position or the para position in view of charge transportability, chemical stability, and T ₁ energy.

Although the specific example of L <^1> is shown below, it is not limited to these. In addition, R _L is abbreviate | omitted in the following specific example.

[Formula 22]

In General Formula (1), R _A , R _B , and R _C are each independently an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a cyano group, a halogen atom, and the condensation represented by A ¹ above. A cyclic group and group obtained by combining these are shown.

As an alkyl group, Preferably it is C1-C10, More preferably, it is a C1-C6, More preferably, it is a C1-C4 alkyl group, A methyl group, an ethyl group, n-propyl group, n-butyl group, or t- Butyl groups are preferred.

As a cycloalkyl group, Preferably it is a C3-C10, More preferably, it is a C4-6, C5 or 6 cycloalkyl group, A cyclopentyl group or a cyclohexyl group is preferable.

As an aryl group which consists only of a ring, a phenyl group is preferable.

As a heteroaryl group which consists only of a monocyclic ring, the heteroaryl group which consists only of nitrogen-containing or sulfur-containing monocyclic groups is preferable, a pyridyl group, a pyrazyl group, a pyrimidyl group, or a thiophenyl group is more preferable, and a pyridyl group is more preferable.

R _A , R _B , and R _C are preferably an aryl group consisting of only an alkyl group and a monocyclic ring, a silyl group, and a cyano group, more preferably an aryl group consisting of only an alkyl group and a monocyclic ring, and still more preferably an aryl consisting of only a single ring. Qi.

In General Formula (1), a1 and b1 respectively independently represent the integer of 0-4. In order for charge transport property and the synthesis | combination to be easy, the integer of 0-2 is preferable as a1 and b1, 0 or 1 is more preferable, and 0 is still more preferable.

In general formula (1), c1 represents the integer of 0-3. For reasons of easy charge transportability and synthesis, an integer of 0 to 2 is preferable, as c1, 0 or 1 is more preferable, and 0 is more preferable.

In General Formula (1), X ¹ , X ² , X ³ , and X ⁴ each independently represent a carbon atom or a nitrogen atom. From the viewpoint of chemical stability, X ² is preferably a carbon atom, and more preferably X ¹ , X ² , X ³ , and X ⁴ are all carbon atoms.

In General Formula (1), R _D represents a substituent selected from a substituent group W.

It is preferable that R <_D> is a group obtained by combining an alkyl group, an aryl group which consists only of a single ring, a silyl group, a cyano group, a fluorine atom, the condensed ring group represented by said A <^1> , and these.

When R <_D> represents an alkyl group, it is a C1-C6 alkyl group from a viewpoint of charge transport property as an alkyl group, More preferably, it is a C1-C4 alkyl group. 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, 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, or 2,3-dimethylbutyl group, etc. are mentioned, methyl group, ethyl group, n-propyl group, iso Propyl 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, methyl group, ethyl group, Isopropyl group, n-butyl group, or t-butyl group is more preferable, and a methyl group is still more preferable.

Moreover, as this alkyl group, the alkyl group substituted by the fluorine atom is preferable, A C1-C4 perfluoroalkyl group is more preferable, A trifluoromethyl group is further more preferable.

When R _D represents a cycloalkyl group, the cycloalkyl group is preferably a cycloalkyl group having 3 to 10 carbon atoms, more preferably 4 to 6 carbon atoms, still more preferably 5 to 6 carbon atoms, and a cyclopentyl group, or Cyclohexyl groups are preferred.

When R <_D> represents an aryl group which consists only of a single ring, a phenyl group is preferable as an aryl group which consists only of that single ring.

In addition, it is also preferable that R _D is a condensed ring group is a substituted phenyl group represented by A ^1. The preferable range of the condensed ring represented by A ¹ is the same as described above.

When R _D represents a heteroaryl group consisting of only a single ring, the heteroaryl group consisting of only a single ring is preferably a pyridyl group, a pyrazyl group, a pyrimidyl group, or a thiophenyl group, and more preferably a pyridyl group.

When R _D represents a silyl group, the silyl group is preferably a silyl group substituted with an alkyl group or a phenyl group, more preferably a silyl group substituted with an alkyl group or a phenyl group having 1 to 4 carbon atoms, and even more preferably a triphenylsilyl group.

If R _D represents a condensed ring represented by A ^1, the condensed ring groups represented by that A ¹ is condensed and cyclic groups are preferably represented by a A ^{1-substituted} alkyl groups, represented by the A ¹ group is substituted with a carbon number of 1 to 4 The condensed ring group is more preferable, and the condensed ring group represented by A ¹ in which the t-butyl group is substituted is more preferable. The preferable range of the condensed ring represented by A ¹ is the same as described above.

d1 represents the integer of 0-4, and since it is easy for charge transport property and synthesis | combination, the integer of 0-2 is preferable, 0 or 1 is more preferable, and 0 is still more preferable.

When d1 is 1, from the viewpoint of charge transportability and durability, R _D is preferably substituted with X ² .

The compound represented by the general formula (1) is preferably represented by the following general formula (2) or (3), and more preferably represented by the following general formula (2).

(23)

(In General Formula (2), R _S2 represents a group represented by the following General Formula (S2).

&Lt; EMI ID =

R _A , R _B , and R _C each independently represent an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a cyano group, or a halogen atom. When two or more R _<A> , R <_B> and R <_C> exist, they may mutually be same or different, but R _<A> and R <_B> do not become a group which has the same structure as R <_S2> together. a1 and b1 respectively independently represent the integer of 0-4. c1 represents the integer of 0-3.

R _D represents a substituent selected from the following substituent group W. When two or more R <_D> exists, they may mutually be same or different. d1 represents the integer of 0-4.

R _L represents a substituent selected from the following substituent group W. When two or more R <_L> exists, they may mutually be same or different. L1 represents the integer of 0-4.

L2 represents the integer of 0-3.

Ra ₁ and Ra ₂ each independently represent a hydrogen atom or a substituent selected from the following substituent group W ^A. When two or more Ra <_1> and Ra <_2> exist, they may mutually be same or different.

R _b represents a substituent selected from the following substituent group W. When two or more R <_b> exists, they may mutually be same or different. b2 represents the integer of 0-4. b3 represents the integer of 0-3.

n2 represents 1 or 2.

_Two neighboring ones of Ra ₁ , Ra _2, and R _{b may be} bonded to form a ring having an sp ³ carbon atom.

Substituent group W ^A : An aryl group which consists only of an alkyl group and a monocyclic ring, and the group which the substituent selected from the following substituent group W couple | bonded with these.

Substituent Group W: alkyl group, a cycloalkyl group, an aryl group containing only a single ring, a condensed ring group represented by a heteroaryl group, a silyl group, a cyano group, a fluorine atom, wherein A ¹ containing only a single ring, and which is obtained by a combination of these)

In General Formula (2), R _A , R _B , R _C , R _D , a1, b1, c1, d1, R _L , L1, Ra ₁ and Ra ₂ have the same meanings as described above, and are specific and preferred. The range is the same.

R _b has the same meaning as Rb ₅ to Rb ₈ in General Formula (A-1) described above, and specific examples and preferred ranges are also the same.

b2 represents the integer of 0-4, the integer of 0-2 is preferable, 0 or 1 is more preferable, and 0 is more preferable.

b3 represents the integer of 0-3, Preferably it is 0 or 1, More preferably, it is zero.

L2 is synonymous with L2 in the general formula (L-1) mentioned above, and its preferable range is also the same.

n2 is preferably 1;

The compound represented by General formula (2) can also be represented by following General formula (2) '.

(25)

(In General Formula (2) ', R _A , R _B , R _C , R _D , a1, b1, c1, d1, R _L , L1, L2, Ra ₁ , Ra ₂ , R _b , b2, b3, n2 Is the same meaning as General formula (2), and its preferable range is also the same.

(26)

(In General Formula (3), R _S3 represents a group represented by the following General Formula (S3).

(27)

R _A , R _B , and R _C each independently represent an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a cyano group, or a halogen atom. When two or more R _<A> , R <_B> and R <_C> exist, they may mutually be same or different, but R _<A> and R <_B> do not become a group which has the same structure as R <_S3> together. a1 and b1 respectively independently represent the integer of 0-4. c1 represents the integer of 0-3.

R _D represents a substituent selected from the following substituent group W. When two or more R <_D> exists, they may mutually be same or different. d1 represents the integer of 0-4.

R _L represents a substituent selected from the following substituent group W. When two or more R <_L> exists, they may mutually be same or different. L1 represents the integer of 0-4.

L2 represents the integer of 0-3.

Ra represents a hydrogen atom or a substituent selected from the following substituent group W ^A. Ra may be mutually same or different.

R _b represents a substituent selected from the following substituent group W. When two or more R <_b> exists, they may mutually be same or different. b3 represents the integer of 0-3.

n3 represents 1 or 2.

Two neighboring ones of Ra and R _{b may} combine to form a ring having an sp ³ carbon atom.

Substituent group W ^A : An aryl group which consists only of an alkyl group and a monocyclic ring, and the group which the substituent selected from the following substituent group W couple | bonded with these.

Substituent Group W: alkyl group, a cycloalkyl group, a condensed ring group represented by A ¹ in the aryl group consisting of only a single ring, a heteroaryl group, a silyl group, a cyano group, a fluorine atom containing only a single ring, the general formula (1), and these Group obtained by combining)

In General Formula (3), R _A , R _B , R _C , R _D , a1, b1, c1, d1, R _L , and L1 have the same meanings as described above, and specific examples and preferred ranges are also the same.

Ra is synonymous with Ra <_11> , Ra <_12> , Ra <_15> , and Ra <_16> in general formula (A-4) mentioned above, and its specific example and preferable range are also the same.

L2 is synonymous with L2 in the general formula (L-1) mentioned above, and its preferable range is also the same.

Specific examples and preferred ranges of R _b are the same as those of R b ₂₅ in General Formula (A-3).

b3 represents the integer of 0-3, Preferably it is 0 or 1, More preferably, it is zero.

n3 preferably represents 1;

The compound represented by General formula (3) can also be represented by following General formula (3) '.

(28)

In General Formula (3) ', R _A , R _B , R _C , R _D , a1, b1, c1, d1, R _L , L1, L2, Ra, n3, R _b , b3 are represented by General Formula (3) and It is synonymous and a preferable range is also the same.

It is preferable that the molecular weight of the compound represented by General formula (1) is 400 or more and 1200 or less, It is more preferable that it is 500 or more and 1000 or less, It is more preferable that it is 550 or more and 800 or less. If the molecular weight is 400 or more, a good amorphous thin film can be formed, and 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 a light emitting material of the organic electroluminescent device, the compound represented by the general formula (1) is preferably contained in the hole block layer.

In the case where a green phosphorescent material or a red phosphorescent light emitting material having a lower T ₁ energy than a blue phosphorescent material is used as the light emitting material of the organic electroluminescent device, the compound represented by the general formula (1) is contained in the light emitting layer or the hole block layer. It is preferable to be.

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, a material is deposited on the cleaned quartz glass substrate to a film thickness of about 50 nm by vacuum deposition, and the phosphorescence emission spectrum of the thin film is subjected to F-7000 Hitachi spectrophotometer (Hitachi High Technologies) under liquid nitrogen temperature. Measure using 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 operating the organic electroluminescent device stably with respect to heat generation during high temperature driving or 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) is shown below, it is not limited to these.

[Formula 29]

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The compound represented by the said General formula (1) is a method as described in Unexamined-Japanese-Patent No. 2004-43349, Unexamined-Japanese-Patent No. 2004-83481, US2006 / 0280965, WO2009 / 021107, Unexamined-Japanese-Patent No. 2009-114068, etc., In addition, it can synthesize | combine well-known reaction in combination.

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 which exists between a light emitting layer and a cathode, and adjoins 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 are 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, Preferably it is a light emitting layer or a hole block layer.

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

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 as an organic substance, and the material illustrated as a host material mentioned below, a fluorescent luminescent material, a phosphorescent luminescent material, and a hydrocarbon material can be applied as an organic substance, 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 above composition. The film thickness of the thin film may be any thickness depending on the application, but is preferably 0.1 nm to 1 mm, more preferably 0.5 nm to 1 μm, still more preferably 1 nm to 200 nm, and particularly preferably 1 Nm to 100 nm.

[Organic electroluminescent device]

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

An organic electroluminescent device of the present invention is 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 the organic layer of the at least one layer At least one of the layers contains a compound represented by the general formula (1) of the present invention. It is preferable that at least one of the anode and the cathode which are a pair of electrodes is transparent or translucent on the property of a light emitting element.

In addition to the light emitting layer, a hole injection layer, a hole transport layer, a block layer (hole block layer, exciton block layer, etc.), an electron transport layer, etc. are mentioned as an organic 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.

An example of a structure of the organic electroluminescent element which concerns on FIG. 1 at this invention is shown. The organic electroluminescent element 10 of FIG. 1 has an organic layer including the light emitting layer 6 between a pair of electrodes (anode 3 and the cathode 9) on the board | substrate 2. As the organic layer, the hole injection layer 4, the hole transport layer 5, the light emitting layer 6, the hole block layer 7 and the electron transport layer 8 are laminated in this order from the anode side 3.

<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 transport layer / light emitting layer / hole block layer / electron transport layer / cathode

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

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

Anode / hole 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

About the element structure of a organic electroluminescent element, a board | substrate, a cathode, and an anode, it is 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>

It is preferable that it is a board | substrate which does not scatter or attenuate the light emitted from an organic layer as a board | substrate used by this invention. 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, structure, 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, and it is more preferable that the layer containing the compound represented by the said General formula (1) 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 transport layer upon application of an electric field, receiving electrons from a cathode, an electron injection layer or an electron transport layer, and providing a place for recombination of holes and electrons to emit light. to be. It is preferable that the light emitting layer in the organic electroluminescent element of this invention contains at least 1 sort (s) of phosphorescent material.

(Luminescent 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, US6303238B1, US6097147, WO00 / 57676, WO00 / 70655, WO01 / 08230, WO01 / 39234A2, WO01 / 41512A1, WO02 / 02714A2, WO02 / 15645A1, WO02 / 44189A1, WO05 / 19373A2, JP 2001-247859, JP 2002-302671, JP 2002-117978, JP 2003-133074, JP 2002-235076, JP 2002-235076, JP 2003-123982, Japanese Laid-Open Patent Publication 2002-170684, EP1211257, Japanese Laid-Open Patent Publication 2002-226495, Japanese Laid-Open Patent Publication 2002-234894, Japanese Laid-Open Patent Publication 2001-247859, Japanese Laid-Open Patent Publication 2001-298470, Japanese Laid-Open Patent Publication 2002-173674, Japanese Laid-Open Patent Publication 2002-203678, Japanese Laid-Open Patent Publication 2002-203679, Japanese Laid-Open Patent Publication 2004-357791, Japanese Laid-Open Patent Publication 2006-256999, Japanese Laid-Open Patent Publication 2007-19462, Japanese Laid-Open Patent Publication 2007- It describes in patent documents, such as 84635 and Unexamined-Japanese-Patent No. 2007-96259. A phosphorescent compound etc. are mentioned, Especially, a more preferable luminescent material is Ir complex, Pt complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu complex, Tb complex. And phosphorescent metal complex compounds such as Gd complex, Dy complex, and Ce complex. Particularly preferred are Ir complexes, Pt complexes, or Re complexes, among which Ir complexes comprising at least one coordination mode of metal-carbon bonds, metal-nitrogen bonds, metal-oxygen bonds, metal-sulfur bonds, Pt Complexes or Re complexes are preferred. 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.

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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 which 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.

_nE1 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 which together with Z ¹ and a nitrogen atom form a heterocyclic ring of 5 or 6 atoms. Examples of the 5 or 6-membered heterocyclic ring containing A ₁ , Z ¹ and a nitrogen atom include a pyridine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, an imidazole ring, a pyrazole ring, , Triazole rings, oxadiazole rings, thiadiazole rings and the like.

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 nitrogen atoms, preferably a pyridine ring, a pyrazine ring, an imidazole ring, a pyrazole ring More preferably a pyridine ring, an imidazole ring, a pyrazine ring, more preferably a pyridine ring, an imidazole ring, and most preferably a pyridine ring.

The 5 or 6 membered hetero ring formed of 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. The substituent on the carbon is preferably an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, or a fluorine atom.

The substituent is appropriately selected for the control of the emission wavelength or the potential, but in the case of shortening, an electron donating group, a fluorine atom, an aromatic ring group is preferable, and an alkyl group, dialkylamino group, alkoxy group, fluorine atom, aryl group, aromatic Hetero ring groups and the like are selected. 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 stability point of a complex.

The substituents may be linked to each other to form a condensed ring. Examples of the ring formed 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 and a pyrazole. A ring, a thiophene ring, a furan ring, etc. are mentioned. 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 and 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 , 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. . The substituent on the carbon is preferably an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, or a fluorine atom.

The substituent is appropriately selected for controlling the emission wavelength or potential, but in the case of making the wavelength longer, an electron donating group and an aromatic ring group are preferable, for example, an alkyl group, a dialkylamino group, an alkoxy group, an aryl group, an aromatic heterocyclic group, or the like is selected. do. In the case of shortening the wavelength, an electron-attracting group is preferable, and for example, a fluorine atom, a cyano group, a perfluoroalkyl group and the like 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 stability point of a complex. The substituents may be linked to each other to form a condensed ring. Examples of the ring formed 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 and a pyrazole. A ring, a thiophene ring, a furan ring, etc. are mentioned. 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.

Moreover, the substituent of the 5 or 6-membered heterocyclic ring formed with said A <_1> , Z <^1> and a nitrogen atom, and the substituent of the 5 or 6-membered ring formed with said B <_1> , Z <^2> and a carbon atom are connected, and are the same condensed ring as mentioned 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, Chemistry-Fundamentals and Applications-by Shokabosa Yamamoto Akio, published in 1982, for example, ligands (e.g., halogen ligands (preferably chlorine ligands), nitrogen-containing heteroaryl ligands (e.g., bipyridyl, phenanthroline And diketone ligands (for example, acetylacetone, etc.) As the ligand represented by (XY), diketones or picolinic acid derivatives are preferable, from the viewpoint of obtaining stability of the complex and high luminous efficiency. Most preferably, it is acetylacetonate (acac) shown below.

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* Indicates a coordination position relative to iridium.

As a ligand represented by (X-Y), the following general formulas (l-1) to (l-15) are preferable, but the present invention is not limited thereto.

[Formula 34]

* 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. Since complex synthesis | combination is easy, Preferably they are (I-1), (I-4), (I-5), Most preferably, it is (I-1). Complexes having these ligands can be synthesized in the same manner as known synthesis examples by using corresponding ligand precursors. For example, it can synthesize | combine by the method shown below using the commercially available difluoroacetylacetone 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).

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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 , 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, particularly preferably a hydrogen atom or a fluorine atom, A ^E1 , A ^E2 and A R ^E of ^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, an aryloxy group Or a fluorine atom, and particularly preferably a hydrogen atom.

When A ^E5 to A ^E8 are preferably CR ^E , and when A ^E5 to A ^E8 are CR ^E , preferably as R ^E , a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, or di 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. When possible, substituents may be connected to each other to form a condensed ring 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 have the same meanings as (XY) and n _{E1 in the} formula (E-1), and their preferred ranges are 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, Perfluoroalkyl group, trifluorovinyl group, -CO ₂ R, -C (O) R, -N (R) ₂ , -NO ₂ , -OR, halogen atom, aryl group or heteroaryl group, and further You may 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.

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, -N (R) 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 cycloalkyl, aryl or heteroaryl, and the condensed 4 to 7 The atomic ring may further have a substituent Z. Among them, R ^T1 and R ^T7 , or R ^T5 and R ^T6 are preferably coordinated to form a benzene ring, and it is particularly preferable that a benzene ring is formed by being condensed with R ^T5 and R ^T6 .

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 ″ are each independently a hydrogen atom, an alkyl group, or a perhalo An alkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group, or a heteroaryl group is shown.

(XY) represents a monoanionic 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. As an alkyl group represented by R <^T1> -R <^T7> and R ', Preferably it is an alkyl group of 1-8 carbon atoms, More preferably, it is an alkyl group of 1-6 carbon atoms, For example, a methyl group, an ethyl group, i -Propyl group, 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. As a cycloalkyl group represented by R <^T1> -R <^T7> and R ', Preferably it is a cycloalkyl group of 4-7 ring atoms, More preferably, it is a cycloalkyl group of 5-6 carbon atoms, for example cyclophene Tyl group, cyclohexyl group, etc. are mentioned.

The alkenyl group represented by R ^T1 to R ^T7 and R 'preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. Examples of the alkenyl group include vinyl, allyl, 1-propenyl, 1-isopropenyl, 1-butenyl, 2-butenyl, 3-pentenyl and the like.

The alkynyl group represented by R ^T1 to R ^T7 and R 'preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. Examples of the alkynyl group include ethynyl, 1-propynyl, 3-pentynyl, and the like.

The perfluoroalkyl group represented by R ^T1 to R ^T7 and R 'includes those in which all the hydrogen atoms of the above-mentioned alkyl group are substituted with fluorine atoms.

As an aryl group represented by R <^T1> -R <^T7> and R ', Preferably, a C6-C30 substituted or unsubstituted aryl group, for example, a phenyl group, a tolyl group, a naphthyl group, etc. are mentioned.

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, For example, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, cinnolinyl, phthalazinyl, quinoxalinyl, pyrrolyl , Indolyl, furyl, benzofuryl, thienyl, benzothienyl, pyrazolyl, imidazolyl, benzimidazolyl, triazolyl, oxazolyl, benzoxazolyl, thiazolyl, Benzothiazolyl group, isothiazolyl group, benzisothiazolyl group, thiadiazolyl group, isooxazolyl group, benzisooxazolyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, imidazolididi Nyl group, thiazolinyl group, sulfolanyl group, carbazolyl group, dibenzofuryl group, Benzothienyl 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 cycloalkyl, aryl or heteroaryl, and the condensed 4 to 7 The atomic ring may further 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 ^T1 to R ^T7 and R '.

Particularly preferred are those wherein A represents CR ', 0 to 2 out of R ^T1 to R ^T7 and R' are an alkyl group or a phenyl group, and all others are hydrogen atoms, and R ^T1 to R ^T7 and Among R ', it is particularly preferable that 0 to 2 are alkyl groups, and all others are hydrogen atoms.

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).

[Formula 37]

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 , -N (R) 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 ₁ 'to R ₅ ' may be bonded to each other to form a condensed 4 to 7 membered ring, and the condensed 4 to 7 membered ring is cycloalkyl, aryl or heteroaryl, and the condensed 4 to 7 membered The ring may further have a substituent Z.

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 ″ are each independently a hydrogen atom, an alkyl group, or a perhalo An alkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group, or a heteroaryl group is shown.

Moreover, the preferable range in R <_1> -R <_5>'is the same as that of R <^T1> -R <^T7> , R' in general formula (E-3). Further, in A it is, together with represents a, R ^T1 ~ R ^T4, R, CR, and _{R 1 '~ R 5',} 0 ~ 2 dogs alkyl group or phenyl group, and the rest are all particularly preferably a hydrogen atom, More preferably, 0 to 2 are alkyl groups and all others are hydrogen atoms in R ^T1 to R ^T4 , R ', and R ₁ ' to R ₅ '.

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 , -N (R) 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 ^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 cycloalkyl, aryl or heteroaryl, The condensed 4-7 membered ring may further have a substituent Z.

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 ″ are each independently a hydrogen atom, an alkyl group, or a perhalo An alkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group, or a heteroaryl group is shown.

Moreover, the preferable range in R <_6>'-R<_8>' is the same as R <^T1> -R <^T7> , R 'in general formula (E-3). Moreover, especially when A represents CR ', 0-2 are R <^2> -R <^T6> , R', and R <_6> -R <_8>', are an alkyl group or a phenyl group, and all remainder are hydrogen atoms especially, It is more preferable that 0-2 are an alkyl group and all others are hydrogen atoms among R <^T2> -R <^T6> , R ', and R <_6> -R <_8>'.

When using the phosphorescent light emitting material represented by General Formula (E-4) or (E-5), the compound represented by General Formula (1) is preferably contained in the light emitting layer or the hole block layer, and more preferably contained in the light emitting layer. desirable.

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

[Chemical Formula 39]

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, -N (R) 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 _1a to R _1k 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.

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 ″ are each independently a hydrogen atom, an alkyl group, or a perhalo An alkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group, or a heteroaryl group is shown.

(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). In addition, R _1a ~ R _1k of 0 to two are each an alkyl group or phenyl group is particularly preferred if the remainder is a hydrogen atom, R _1a ~ R _1k of 0 to two are each the alkyl group and all the rest is a hydrogen atom More preferred.

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).

[Formula 40]

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, -N (R) 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 _1a to R _1k may be bonded to each other to form a condensed 4 to 7 membered ring, and the condensed 4 to 7 membered ring is a cycloalkyl group, an aryl group or a heteroaryl group, and the condensed 4 to 7 membered ring May further have a substituent Z.

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 ″ are each independently a hydrogen atom, an alkyl group, or a perhalo An alkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group, or a heteroaryl group is shown.

(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 are an alkyl group or an aryl group, and all remainder are hydrogen atoms in R <_1a> -R <_1i> .

The definition and the preferable range of (XY) and n _E7 are the same as (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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(42)

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The compound exemplified as the compound represented by the above general formula (E-1) can be synthesized by various methods described in JP-A-2009-99783, US Pat. No. 7279232, and the like. 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, Q ¹ , Q ² , Q ^3, and Q ⁴ may be any of covalent bonds, ionic bonds, coordination bonds, and the like. As an atom couple | bonded with Pt in Q <^1> , Q <^2> , Q <^3> and Q <^4> , a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a phosphorus atom are preferable, and Pt in Q <^1> , Q <^2> , Q <^3> and Q <^4> is preferable. It is preferable that at least 1 is a carbon atom among the atoms couple | bonded, 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.

As Q ¹ , Q ² , Q ³ and Q ^{4, which} are carbon atoms and are bonded to Pt, they may be anionic ligands or neutral ligands. Anionic ligands may be vinyl ligands or aromatic hydrocarbon ring ligands (eg 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.

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. Moreover, substituents may be connected (when Q3 and Q4 are connected, it will become a Pt complex of a cyclic tetradentate 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 hetero ring 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 Pt Aromatic heterocyclic ligand bound to the compound, nitrogen atom-containing aromatic heterocyclic ligand bound to Pt, acyloxy ligand, aryloxy ligand, more preferably aromatic hydrocarbon ring ligand bound to Pt, carbon atom Aromatic heterocyclic ligand which is bonded to Pt and is a nitrogen atom and is bonded to Pt Nitrogen-containing aromatic heterocyclic ligands and acyloxy ligands.

L ¹ , L ² and L ³ represent a single bond or a divalent linking group. Examples of the divalent linking groups represented by L ¹ , L ^2, and L ³ include an alkylene group (methylene, ethylene, propylene, and the like), an arylene group (phenylene, naphthalenediyl), a heteroarylene group (pyridindiyl, thiophendiyl, and the like), Imino group (-NR-) (phenylimino group, etc.), oxy group (-O-), thio group (-S-), phosphinidene group (-PR-) (phenylphosphinidene group, etc.), silylene group (- SiRR'-) (dimethylsilylene group, diphenylsilylene group, etc.), or what combined these is mentioned. Here, as R and R ', an alkyl group, an aryl group, etc. are respectively independently mentioned. These linking groups may further have a substituent.

In view 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).

[Chemical Formula 45]

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 hetero ring. Z ²³ and Z ²⁴ each independently represent a benzene ring or an aromatic hetero ring)

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 carbon atoms together from the viewpoint of the stability of the complex and the light emitting quantum yield of the complex.

Z ²¹ and Z ²² each independently represent a nitrogen-containing aromatic hetero ring. Examples of the nitrogen-containing aromatic hetero rings represented by Z ²¹ and Z ²² include pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring and oxa A diazole ring, a thiadiazole ring, and the like. From the viewpoint of the stability of the complex, the emission wavelength control and the 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, 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.

Z ²³ and Z ²⁴ each independently represent a benzene ring or an aromatic hetero ring. Examples of the nitrogen-containing aromatic hetero rings 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 tria A sol ring, an oxadiazole ring, a thiadiazole ring, a thiophene ring, a furan ring, etc. are mentioned. As a ring represented by Z ²³ , Z ²⁴ from the viewpoint of stability of the complex, emission wavelength control, and emission quantum yield, a benzene ring, a pyridine ring, a pyrazine ring, an imidazole ring, a pyrazole ring, a thiophene ring, and Preferably they are a benzene ring, a pyridine ring, a pyrazole ring, More preferably, they are a benzene ring and a pyridine 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-4).

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(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. When A ⁴⁰¹ to A ⁴⁰⁶ are CR, R ⁴⁰² and A ⁴⁰⁵ are preferably R, preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom, and a cyano group, 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, 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.

In each of the A ~ ⁴⁰⁷ A ⁴¹⁴ A ⁴⁰⁷ roneun A ~ ⁴¹⁰ and A ~ ^{411 414} A, the number of N (nitrogen atom) is in the range of 0 to 2 and more preferably is 0-1. 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.

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).

[Formula 47]

(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 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.

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).

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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 hetero ring. Z ⁶³ represents Each independently represents a benzene ring or an aromatic hetero ring, 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 and Z ⁶² have the same meanings as Z ²¹ and Z ^{22 in} General Formula (C-2), and the preferred ranges are 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. Moreover, substituents may 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).

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(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 General 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 the 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 as 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 further.

(50)

(51)

(52)

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 techniques, 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 solvents, in the presence of bases (inorganic, organic, various bases such as sodium methoxide, t-butoxy potassium, tri Ethylamine, potassium carbonate, and the like), or in the absence of a base, can be obtained by 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 thickness of a light emitting layer is not specifically limited, Usually, it is preferable that it is 2 nm-500 nm, Especially, from a viewpoint of an external quantum efficiency, it is more preferable that it is 5 nm-200 nm, It is more preferable that it is 10 nm-100 nm. desirable.

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 is a compound which does not substantially emit light. Here, the term "substantially does not emit light" means that the amount of light emitted from the compound that does not substantially emit light is preferably 5% or less 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 Conductive polymer oligomers, organic silanes, carbon films, pyridine, pyrimidine, triazine, imidazole, pyrazole, triazole, oxazole, oxadiazole, fluorenone, anthraquinodimethane, anthrone, diphenylquinone, etc. , Thiopyran dioxide, Heterocyclic tetracarboxylic anhydrides such as levodiimide, fluorenylidene methane, distyrylpyrazine, fluorine-substituted aromatic compounds, naphthalene perylene, metal complexes of metal phthalocyanine, phthalocyanine and 8-quinolinol derivatives, metal phthalocyanine and benzoxazole And various metal complexes represented by metal complexes having benzothiazole as a ligand, and derivatives thereof (may have a substituent or a condensation).

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 the light-emitting layer, the lowest triplet state of the host material of the film in the excitation energy (T ₁ energy) the T ₁ of the phosphorescent light-emitting material Is higher than energy in terms of color purity, luminous efficiency and drive durability. T ₁ of the host material is 0.1 eV or more greater than the T ₁ is preferably a phosphorescent light emitting material, and at least 0.2 eV and preferably greater than it, it is more preferably greater than 0.3 eV.

Because dumping by T ₁ in the film state 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 if the 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 from a portion, 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.

Moreover, 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 all the compounds which form a light emitting layer from a light emitting efficiency and a driving 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.

(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 an organic electroluminescent device having low cost and high efficiency. The charge transport layer is more preferably a hole injection layer, a hole transport layer or an electron block layer.

(Hole injection layer, hole transport layer)

The hole injection layer and the hole transport layer are layers having a function of receiving holes from the anode or the anode side and transporting them to the cathode side.

Regarding the hole injection layer and the hole transport layer, the matters described in 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 including an electron-accepting dopant in the hole injecting layer, the hole injecting 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 drawing electrons from the material to be doped to generate radical cations. For example, tetracyanoquinomimethane (TCNQ), tetra Fluorotetracyanoquinomethane (F ₄ -TCNQ), molybdenum oxide, and the like.

It is preferable to contain 0.01 mass%-50 mass% with respect to the mass of all the compounds which form 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 the 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, Benzoimidazole derivatives, imidazopyridine derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimide derivatives, fluorenylidene methane derivatives, distyrylpyrazine derivatives Metal complexes represented by metal complexes of aromatic ring tetracarboxylic anhydrides, phthalocyanine derivatives, 8-quinolinol derivatives such as phthalic acid, naphthalene, and perylene, metal phthalocyanine, benzoxazole or benzothiazole as ligands , Organosilane derivatives represented by silol, naphthalene, anthracene, phenanthrene, tripe Preferably selected from chukhwan hydrocarbon compounds, such as alkylene, pyrene, and more preferably from pyridine derivatives, benzo will imidazole derivatives, any of imidazopyridine derivatives, metal complexes, chukhwan hydrocarbon compound.

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 still 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. Including an electron donating dopant in the electron injecting layer has the effect of improving the electron injecting property, lowering the driving voltage, and improving the efficiency. The electron donor dopant may be any of organic materials and inorganic materials as long as electrons can be given to the doped material to generate radical anions. Examples of the electron donating dopant include tetrathiafulvalene (TTF), tetrathianaphtha Dihydroimidazole compounds such as tetra (TTT) and bis- [1,3 diethyl-2-methyl-1,2-dihydrobenzimidazolyl], lithium, cesium and the like.

It is preferable to contain 0.01 mass%-50 mass% with respect to the mass of the whole compound which forms an electron injection layer, and, as for the electron donating dopant in an electron injection layer, it is more preferable that 0.1 mass%-40 mass% are contained, and it is 0.5 mass 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 block layer is preferably 1 nm to 500 nm, more preferably 3 nm to 100 nm, still more preferably 5 nm to 50 nm.

The hole block 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 material used for the hole block layer is preferably higher than the T ₁ energy of the phosphorescent light emitting material in view of color purity, luminous efficiency and driving durability. To be larger in the film in the state of the material used for the hole blocking layer T ₁ is at least 0.1 eV greater than T ₁ is preferably a phosphorescent light emitting material, and at least 0.2 eV and preferably greater than it, more than 0.3 eV is more preferable.

(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.

The material used for the electron blocking layer is preferably higher than the T ₁ energy of the phosphorescent light emitting material in view of color purity, luminous efficiency and driving durability. Preferably T ₁ of the film in the state of the material used for the electron-blocking layer is more than 0.1 eV greater than the T ₁ of the phosphorescent light emitting material, and at least 0.2 eV and preferably greater than it, it is more preferably greater than 0.3 eV.

(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.

As for the sealing container, the matters described in the paragraph [0171] of Japanese Patent Laid-Open Publication No. 2008-270736 can be applied to the present invention.

(Driving)

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

As for the driving method of the organic electroluminescent element of the present invention, JP-A-2-148687, JP-A-6-301355, JP-A 5-29080, JP-A-7- 134558, Japanese Patent Application Laid-Open No. Hei 8-234685, Japanese Patent Application Laid-Open No. Hei 8-241047, the driving method described in each specification of Japanese Patent No. 2784615, US Patent 5828429, US Patent 6023308, etc. can be applied. have.

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. As the numerical value of the external quantum efficiency, the maximum value of the external quantum efficiency when the device is driven at 20 ° C, or the value of the external quantum efficiency at around 300 to 400 cd / m2 when the device is driven at 20 ° C can be used. .

It is preferable that the internal quantum efficiency of the organic electroluminescent element of this invention is 30% or more, 50% or more is more preferable, and 70% or more is more preferable. 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 this invention can be used suitably for a display element, a display, a backlight, an electrophotographic, an illumination light source, a recording light source, an exposure light source, a reading light source, a cover, a sign, interior, or 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 a light emitting device of the present invention. 2 is constituted by a transparent substrate (support substrate) 2, an organic electroluminescence element 10, a sealing container 16, and the like.

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 contact bonding 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.

Here, as the contact bonding layer 14, photocurable adhesives, such as an epoxy resin, and a thermosetting adhesive can be used, for example, a thermosetting adhesive sheet can also be used.

The use of the light emitting device of the present invention is not particularly limited. For example, the light emitting device can be 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 the present invention will be described with reference to Fig.

3 is a cross-sectional view schematically showing an example of a lighting apparatus of the present invention. As shown in Fig. 3, the illumination device 40 of the present invention includes the above-described organic EL element 10 and a light scattering member 30. [ 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. In Fig. 3, the light scattering member 30 is a member in which the fine particles 32 are dispersed on the transparent substrate 31. [ As the transparent substrate 31, for example, a glass substrate is preferably used. The fine particles 32 are preferably transparent resin fine particles. As the glass substrate and transparent resin fine particles, all known ones can 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, and the scattered light. Is emitted from the light exit surface 30B as illumination light.

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

(53)

9,9-dimethyl-2-fluoreneboronic acid 3.57 g (15.0 mmol), 3,3'-dibromo-1,1'-biphenyl 9.36 g (30.0 mmol), palladium acetate (Pd (OAc) ₂ ) 101 mg (0.45 mmol), triphenylphosphine (PPh ₃ ) 472 mg (1.80 mmol), sodium carbonate 3.18 g (30.0 mmol), toluene 65 mL and water 30 mL were mixed, under a nitrogen atmosphere. It was heated to reflux for time. After cooling the reaction liquid to room temperature, the organic layer was extracted by liquid separation and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the solvent was purified by silica gel column chromatography (developing solvent: toluene / hexane (1: 4)) to obtain 4.40 g of the synthetic intermediate 1 (yield 69%).

2.34 g (5.5 mmol) of synthetic intermediate 1, 2.05 g (5.78 mmol) of 4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -1,3,2-dioxaborane ), Tris (dibenzylideneacetone) dipalladium (Pd ₂ (dba) ₃ ) 151 mg (0.17 mmol), 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl (SPhos) 271 mg (0.66 mmol), 2.33 g (11.0 mmol) of potassium phosphate, 30 ml of 1,2-dimethoxyethane (DME) and 15 ml of water were mixed and heated to reflux for 7 hours under a nitrogen atmosphere. After cooling the reaction solution to room temperature, the precipitate was filtered and washed sequentially with pure water, ethanol and hexane. After drop-washing the obtained solid with 50 ml of ethanol, 2.50g of compound 1 was obtained by recrystallization with toluene / ethanol (2: 1) (yield 79%).

NMR data of Compound 1

Synthesis Example 2 Synthesis of Compound 2

[Formula 54]

4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -1,3,2-dioxaborane 7.08 g (20.0 mmol), m.bromoiobenzene 16.97 g (60.0 mmol), palladium acetate 135 mg (0.60 mmol), triphenylphosphine 629 mg (2.40 mmol), sodium carbonate 4.24 g (40.0 mmol), 1,2-dimethoxyethane 100 ml and water 50 ml It heated and refluxed for 7 hours in nitrogen atmosphere. After the reaction, water and ethyl acetate were added to extract the organic layer. The organic layer was concentrated under reduced pressure, and then the origin component was removed by silica gel column chromatography (developing solvent: toluene). The solid obtained by distilling off the solvent under reduced pressure was dissolved in a small amount of methylene chloride, and methanol was added to precipitate a solid. This solid was filtered and 7.33g of synthetic intermediate 2 was obtained by wash | cleaning sequentially with methanol and hexane (yield 96%).

7.20 g (18.8 mmol) of synthetic intermediate 2, 7.16 g (28.2 mmol) of bis (pinacolato) diboron, [1,1'-bis (diphenylphosphino) ferrocene] palladium dichloridedichloromethane complex ( 1: 1) (PdCl ₂ (dppf)) 461 mg (0.56 mmol), potassium acetate (AcOK) 5.54 g (56.4 mmol), and 80 ml of dimethyl sulfoxide (DMSO) were mixed, and it was made at 70 degreeC by nitrogen atmosphere. Stir for 4 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 origin component was removed by silica gel chromatography (developing solvent: toluene). After distilling off the solvent under reduced pressure, 5.73 g of the synthetic intermediate 3 was obtained by drop washing the obtained solid with ethanol (yield 71%).

1.72 g (4.0 mmol) of synthetic intermediate 3, 1.58 g (4.0 mmol) of 2-bromo-9,9'-spirobifluorene, 110 mg (0.12 mmol) of tris (dibenzylideneacetone) dipalladium , 1,97 mg (0.48 mmol) of 2-dicyclohexyl phosphino-2 ', 6'-dimethoxybiphenyl, 1.70 g (8.0 mmol) of potassium phosphate, 20 ml of toluene, and 10 ml of water were mixed, and it was nitrogen atmosphere. Under heating for 5 hours. Water and hexane were added to the reaction solution, and the solid was filtered and washed sequentially with pure water, ethanol and hexane. By recrystallizing the obtained solid twice with toluene / hexane (1: 2), 1.93g of compound 2 was obtained (yield 78%).

NMR data of Compound 2

Synthesis Example 3 Synthesis of Compound 7

(55)

4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -1,3,2-dioxaborane 7.08 g (20.0 mmol), 3,3'-dibromo-1 6.24 g (20.0 mmol), 1'-biphenyl, 225 mg (1.00 mmol) palladium acetate, 1.05 g (4.00 mmol) triphenylphosphine, 4.24 g (40.0 mmol) sodium carbonate, 220 ml toluene 110 mL was mixed and heated to reflux for 12 hours under a nitrogen atmosphere. After cooling the reaction solution to room temperature, the organic layer was extracted by liquid separation. The solvent was distilled off under reduced pressure, and then purified by silica gel column chromatography (developing solvent: toluene / hexane (1: 1)). The obtained solution was concentrated and 5.57 g of a synthetic intermediate 4 was obtained by drop washing the precipitated solid with ethanol (yield 51%).

5.46 g (10.0 mmol) of synthetic intermediate 4, 3.81 g (15.0 mmol) of bis (pinacolato) diboron, [1,1'-bis (diphenylphosphino) ferrocene] palladium dichloridedichloromethane complex ( 1: 1: 408 mg (0.50 mmol), 2.94 g (30.0 mmol) of potassium acetate, and 80 ml of dimethyl sulfoxide were mixed, and it stirred at 70 degreeC under nitrogen atmosphere for 5 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)). The obtained solution was concentrated, and 3.24 g of synthetic intermediate 5 was obtained by drop washing the precipitated solid with ethanol (yield 64%).

3.19 g (6.3 mmol) of the synthetic intermediate 5, 1.55 g (6.0 mmol) of 2-bromo-9,10-dihydrophenanthrene, 165 mg (0.18 mmol) of tris (dibenzylideneacetone) dipalladium, 296 mg (0.72 mmol) of 2-dicyclohexylphosphino-2 ', 6'- dimethoxybiphenyl, 2.55 g (12.0 mmol) of potassium phosphate, 35 ml of toluene, and 20 ml of water were mixed, It was heated to reflux for 5 hours. After cooling the reaction solution to room temperature, the organic layer was extracted by liquid separation. The solvent was distilled off under reduced pressure, and then purified by silica gel column chromatography (developing solvent: toluene / hexane (1: 1)). After distilling off the solvent under reduced pressure, 2.38 g of compound 7 was obtained by recrystallizing three times with toluene / hexane (1: 2) (yield 71%).

NMR data of Compound 7

The other compound was synthesize | combined with the following synthetic routes. Reaction conditions, a purification method, etc. comply with the synthesis examples 1-3.

(56)

(57)

(58)

[Chemical Formula 59]

(60)

(61)

[Formula 62]

(63)

&Lt; EMI ID =

(65)

[Formula 66]

(67)

2. Device manufacturing and evaluation

All of the materials used in the manufacture of the device 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 at 254 nm) was 99.9% or more.

(Example 1)

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

First layer: HAT-CN: 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 1: film thickness 30 nm

4th layer: HBL material described in Table 1: film thickness 5 nm

5th layer: Alq: film thickness 45 nm

Lithium fluoride 0.1 nm and metal aluminum 100 nm were vapor-deposited in this order on this, and it was set as the cathode.

The obtained laminated body was put into the glove box substituted by nitrogen gas, without contacting air | atmosphere, and it sealed using the glass sealing can and an ultraviolet curable adhesive (XNR5516HV, Nagase Chiba Co., Ltd.), and the elements 1-1 to 1 -7 and comparative elements 1-1 to 1-5 were obtained. Table 1 shows the results obtained by evaluating these devices in terms of efficiency, drive voltage, durability, and efficiency after high temperature storage. Moreover, in Comparative element 1-5, since the comparative compound 7 could not be formed into a film by the vacuum vapor deposition method, an element could not be manufactured.

(a) efficiency

A DC voltage was applied to each element using a source measure unit 2400 manufactured by Toyo Technica to emit light, and the luminance thereof was measured using a luminance meter BM-8 manufactured by Topcon Corporation. The emission spectrum and the emission wavelength were measured using a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics. Based on these, the external quantum efficiency whose luminance is about 1000 cd / m <2> was computed by the luminance conversion method. 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 cd / m 2. The applied voltage at this time was taken as an index of the evaluation of the driving voltage. The smaller the number is, the more preferable the driving voltage is.

(c) durability

Each element was made to emit light continuously by applying a DC voltage such that the luminance was 5000 cd / m 2, and the time required until the luminance was 4000 cd / m 2 was used as an index of durability. In Table 1, the value of element 1-1 is shown in Table 2, the value of element 2-1 is shown in Table 2, the value of element 3-1 is shown in Table 3, and the value of element 4-1 is shown in Table 4, Table 5 In Table 6, the value of the element 6-1 is shown in Table 6, and the value of the element 7-1 is 1.0 in Table 7, respectively, and was represented by the relative value in each table. Durability is so preferable that a number is large.

(d) Efficiency after high temperature storage (heat resistance)

After storing each element for 100 hours in a 100 degreeC thermostat, efficiency was measured by the method similar to (a). The larger the number, the better.

(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: 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: HBL material described in Table 2: Film thickness 10 nm

Sixth layer: ET-2: film thickness 20 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: CuPc: film thickness 10 nm

Second layer: NPD: film thickness 30 nm

Third layer: host material and RD-1 (mass ratio 95: 5) described in Table 3: film thickness 30 nm

Fourth layer: ET-3: film thickness 50 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: TCTA: film thickness 35 nm

Second layer: HT-2: film thickness 5 nm

Third layer: BAlq and RD-2 (mass ratio 90: 10): film thickness 30 nm

Fourth layer: HBL material described in Table 4: Film thickness 5 nm

Fifth layer: ET-4: film thickness 45 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.

First layer: HAT-CN: film thickness 10 nm

Second layer: NPD: film thickness 115 nm

Third layer: HT-3: film thickness 5 nm

4th layer: H-2 and Firpic (mass ratio 90:10): film thickness 30 nm

Fifth layer: HBL material described in Table 5: Film thickness 5 nm

Sixth layer: ET-5: 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-3: film thickness 3 nm

Fourth layer: H-3 and BD-1 (mass ratio 85:15): film thickness 30 nm

5th layer: HBL material described in Table 6: film thickness 5 nm

Sixth layer: BAlq: film thickness 25 nm

(Example 7)

A glass substrate having an ITO film having a thickness of 0.5 mm and a width of 2.5 cm (manufactured by Geomatec Co., Ltd., having a surface resistance of 10 Ω / □ (also referred to as Ω / sq.)) Was placed in a washing container and ultrasonically cleaned in 2-propanol, followed by 30 UV-ozone treatment was performed for a minute. 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 A light emitting layer of 50 nm was formed.

ET-4 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 100 nm of lithium fluoride and 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 sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Chiba Co., Ltd.). 1-7-3 and the comparative elements 7-1-7-7 were obtained.

From the above result, the element using the compound represented by General formula (1) of this invention is high in efficiency, low in drive voltage, excellent in durability, and high in efficiency after high temperature storage.

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

(68)

[Formula 69]

(70)

Industrial availability

According to the present invention, it is possible to provide an organic electroluminescent element having excellent luminous efficiency and durability, low driving voltage and excellent heat resistance.

Moreover, according to this invention, the compound and charge transport material which can be provided to the organic electroluminescent element which have the outstanding luminous efficiency, durability, low drive voltage, and excellent heat resistance can be provided.

Although this invention was detailed also demonstrated with reference to the specific embodiment, it is clear for those skilled in the art that various changes and correction can be added without deviating from the mind and range of this invention.

This application is based on the JP Patent application (patent application 2010-201488) of an application on September 8, 2010, The content is taken in here as a reference.

2 … Board
3…. anode
4 … Hole injection layer
5 ... Hole transport layer
6 ... The light-
7 ... Hole block layer
8 … Electron transport layer
9 ... cathode
10 ... Organic electroluminescent device
11 ... Organic layer
12 ... Protective layer
14. Adhesive layer
16. Sealing container
20 ... Light emitting device
30 ... Light scattering member
31 ... Transparent substrate
30A. Light incident surface
30B. Light emitting surface
32 ... Particulate
40 ... Lighting device

Claims (16)

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 a compound.
[Formula 1]

(In General Formula (1), R _S1 represents a group represented by the following General Formula (S1).
(2)

X ¹ , X ² , X ³ , and X ⁴ each independently represent a carbon atom or a nitrogen atom.
L ¹ represents a linking group composed of at least one ring selected from the group consisting of a single bond or an aromatic hydrocarbon ring consisting of only a single ring and an aromatic hetero ring consisting of only a single ring. The linking group may have a substituent selected from the following substituent group W.
A ¹ is one hydrogen from a condensed ring in which a condensed ring is condensed by a 5- or 6-membered ring containing a sp ³ carbon atom, at least one ring selected from the group consisting of a monocyclic aromatic hydrocarbon ring and a monocyclic aromatic heterocyclic ring; The monovalent group obtained by removing an atom is shown. The monovalent group may have a substituent selected from the following substituent group W.
R _A , R _B , and R _C are each independently an alkyl group, a cycloalkyl group, an aryl group consisting of only a ^single ring, a heteroaryl group consisting only of a single ring, a cyano group, a halogen atom, a condensed ring group represented by A ¹ , and a combination thereof The group obtained is shown. When two or more R _<A> , R <_B> and R <_C> exist, they may mutually be same or different, but R _<A> and R <_B> do not become a group which has the same structure as R <_S1> together. a1 and b1 respectively independently represent the integer of 0-4. c1 represents the integer of 0-3.
R _D represents a substituent selected from the following substituent group W. When two or more R <_D> exists, they may mutually be same or different. d1 represents the integer of 0-4.
In X ¹ , X ² , X ³ , and X ⁴ , the carbon atom not bonded to R _D represents = CH—.
Substituent Group W: alkyl group, a cycloalkyl group, an aryl group containing only a single ring, a condensed ring group represented by a heteroaryl group, a silyl group, a cyano group, a fluorine atom, wherein A ¹ containing only a single ring, and which is obtained by a combination of these) The method of claim 1,
Condensing the following general formula (A-1), (A -2), (A-3), (A-4), or (A-5) The organic electroluminescent device, indicated by the ring in the above-mentioned A ^1.
(3)

(In general formula (A-1), (A-2), (A-3), (A-4), and (A-5),
X ^a , X ^b , X ^c , X ^d , X ^e , X ^f , X ^g , and X ^h each independently represent C (Rb ₂₅ ) or a nitrogen atom.
Y ¹ , Y ² , Y ³ , Y ⁴ , and Y ⁵ are each independently C (Ra ₁₅ ) (Ra ₁₆ ), oxygen atom, sulfur atom, N (Ra ₁₇ ), Si (Ra ₁₈ ) (Ra ₁₉ ) , C = 0, P (= 0) (Rb ₂₆ ), or S (= 0) ₂ .
Ra ₁ to Ra ₁₉ each independently represent a hydrogen atom or a substituent selected from the following substituent group W ^A.
Rb ₁ to Rb ₂₆ each independently represent a hydrogen atom or a substituent selected from the following substituent group W.
Two neighboring ones of Ra ₁ to Ra ₁₉ and Rb ₁ to Rb _{26 may} combine to form a ring having an sp ³ carbon atom.
Substituent group W ^A : An aryl group which consists only of an alkyl group and a monocyclic ring, and the group which the substituent selected from the following substituent group W couple | bonded with these.
Substituent group W: an alkyl group, an aryl group consisting of only a ^single ring, a heteroaryl group consisting only of a single ring, a silyl group, a cyano group, a fluorine atom, a condensed ring group represented by the above-mentioned A ¹ , and a group obtained by combining them) 3. The method according to claim 1 or 2,
The organic electroluminescent element in which said L <^1> is represented with the following general formula (L-1).
[Chemical Formula 4]

(In general formula (L-1), X _L represents C (Rb ₂₇ ) or a nitrogen atom. R _L represents a substituent selected from the following substituent group W. When a plurality of R _L are present, they may be the same as each other. Rb ₂₇ represents a hydrogen atom or a substituent selected from the following substituent group W. When a plurality of Rb _{27 's} are present, they may be the same as or different from each other, L1 represents an integer of 0 to 4. L2 represents 0 The integer of-3. When L2 is 0, general formula (L-1) represents a single bond * represents a coupling site.
Substituent Group W: alkyl group, a cycloalkyl group, a condensed ring group represented by A ¹ in the aryl group consisting of only a single ring, a heteroaryl group, a silyl group, a cyano group, a fluorine atom containing only a single ring, the general formula (1), and these Group obtained by combining) The method according to any one of claims 1 to 3,
The organic electroluminescent element whose compound represented by the said General formula (1) is represented by following General formula (2) or (3).
[Chemical Formula 5]

(In General Formula (2), R _S2 represents a group represented by the following General Formula (S2).
[Chemical Formula 6]

R _A , R _B , and R _C each independently represent an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a cyano group, or a halogen atom. When two or more R _<A> , R <_B> and R <_C> exist, they may mutually be same or different, but R _<A> and R <_B> do not become a group which has the same structure as R <_S2> together. a1 and b1 respectively independently represent the integer of 0-4. c1 represents the integer of 0-3.
R _D represents a substituent selected from the following substituent group W. When two or more R <_D> exists, they may mutually be same or different. d1 represents the integer of 0-4.
R _L represents a substituent selected from the following substituent group W. When two or more R <_L> exists, they may mutually be same or different. L1 represents the integer of 0-4.
L2 represents the integer of 0-3.
Ra ₁ and Ra ₂ each independently represent a hydrogen atom or a substituent selected from the following substituent group W ^A. When two or more Ra <_1> and Ra <_2> exist, they may mutually be same or different.
R _b represents a substituent selected from the following substituent group W. When two or more R <_b> exists, they may mutually be same or different. b2 represents the integer of 0-4. b3 represents the integer of 0-3.
n2 represents 1 or 2.
_Two neighboring ones of Ra ₁ , Ra _2, and R _{b may be} bonded to form a ring having an sp ³ carbon atom.
Substituent group W ^A : An aryl group which consists only of an alkyl group and a monocyclic ring, and the group which the substituent selected from the following substituent group W couple | bonded with these.
Substituent Group W: alkyl group, a cycloalkyl group, an aryl group containing only a single ring, a condensed ring group represented by a heteroaryl group, a silyl group, a cyano group, a fluorine atom, wherein A ¹ containing only a single ring, and which is obtained by a combination of these)
(7)

(In General Formula (3), R _S3 represents a group represented by the following General Formula (S3).
[Chemical Formula 8]

R _A , R _B , and R _C each independently represent an alkyl group, a cycloalkyl group, an aryl group consisting of only a single ring, a heteroaryl group consisting of only a single ring, a cyano group, or a halogen atom. When two or more R _<A> , R <_B> and R <_C> exist, they may mutually be same or different, but R _<A> and R <_B> do not become a group which has the same structure as R <_S3> together. a1 and b1 respectively independently represent the integer of 0-4. c1 represents the integer of 0-3.
R _D represents a substituent selected from the following substituent group W. When two or more R <_D> exists, they may mutually be same or different. d1 represents the integer of 0-4.
R _L represents a substituent selected from the following substituent group W. When two or more R <_L> exists, they may mutually be same or different. L1 represents the integer of 0-4.
L2 represents the integer of 0-3.
Ra represents a hydrogen atom or a substituent selected from the following substituent group W ^A. Ra may be mutually same or different.
R _b represents a substituent selected from the following substituent group W. When two or more R <_b> exists, they may mutually be same or different. b3 represents the integer of 0-3.
n3 represents 1 or 2.
Two neighboring ones of Ra and R _{b may} combine to form a ring having an sp ³ carbon atom.
Substituent Group W ^A : An alkyl group, an aryl group consisting of only a single ring, and a group having a substituent selected from the following substituent group W bonded thereto.
Substituent Group W: alkyl group, a cycloalkyl group, a condensed ring group represented by A ¹ in the aryl group consisting of only a single ring, a heteroaryl group, a silyl group, a cyano group, a fluorine atom containing only a single ring, the general formula (1), and these Group obtained by combining) The method according to any one of claims 1 to 4,
An organic electroluminescent device comprising at least one phosphorescent light emitting material in the light emitting layer. The method of claim 5, wherein
An organic electroluminescent element, wherein the phosphorescent material is represented by the following general formula (E-1).
[Chemical Formula 9]

(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 which 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 ligand.
n _E1 represents an integer of 1 to 3) The method according to claim 6,
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).
[Formula 10]

(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.
(XY) represents a monoanionic ligand.
n _E2 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 containing the compound represented by the said General formula (1) in a hole block layer. 10. The method according to any one of claims 1 to 9,
An organic electroluminescent element, wherein at least one organic layer is formed by film formation by a solution coating method. 11. The method according to any one of claims 1 to 10,
The organic electroluminescent element by which the organic layer containing the compound represented by the said General formula (1) was formed into a film by the solution coating method. The light emitting device using the organic electroluminescent element as described in any one of Claims 1-11. The display apparatus using the organic electroluminescent element in any one of Claims 1-11. The illuminating device using the organic electroluminescent element of any one of Claims 1-11. The charge transport material represented by the said General formula (1), (2), or (3) in any one of Claims 1-4. The compound represented by the said General formula (1), (2), or (3) in any one of Claims 1-4.

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