JP5018138B2 - Luminescent material and organic electroluminescent device using the same - Google Patents

Description

  The present invention relates to a benzocarbazole compound, a light emitting layer material using the compound, and an organic electroluminescent device.

  The organic electroluminescent element is a self-luminous light emitting element and is expected as a light emitting element for display or illumination. 2. Description of the Related Art Conventionally, display devices using light emitting elements that emit electroluminescence have been studied variously because they can be reduced in power and thinned. Further, organic electroluminescent elements made of organic materials can be easily reduced in weight and size. Therefore, it has been actively studied.

  An organic electroluminescent element has a structure which consists of a pair of electrode which consists of an anode and a cathode, and the one layer or several layer which is arrange | positioned between the said pair of electrodes and contains an organic compound. The layer containing an organic compound includes a light-emitting layer and a charge transport / injection layer that transports or injects charges such as holes and electrons. Various organic materials have been developed as the organic compound. In particular, research and development of organic materials for the light emitting layer are actively conducted.

  The light emitting material of the organic electroluminescence device is classified into a fluorescent material using singlet excitons and a phosphorescent material using triplet states according to the light emission mechanism. Among the light emitting materials, improvement of the host material is particularly demanded. Until now, many anthracene derivatives have been used as fluorescent host materials (see, for example, Patent Document 1 and Non-Patent Document 1). As a phosphorescent host material, it is known to use 4,4-N, N′-dicarbazole-biphenyl (hereinafter abbreviated as CBP) (see, for example, Patent Document 2). However, a compound such as CBP has a symmetric molecular structure, and there is a concern that it may have high crystallinity. Patent Document 3, Patent Document 4 and Patent Document 5 propose an organic EL element using a carbazole derivative having an asymmetric structure. Further, Patent Document 6 and Non-Patent Document 2 disclose organic EL elements using a benzocarbazole derivative as a host material. However, there is a problem that the light emission efficiency is low and the light emission lifetime is short, and the improvement has been made. It was desired.

  In addition, Patent Document 7 discloses an example in which a benzocarbazole derivative is used as a hole transport material, but it is not used as a light emitting material.

International Publication No. 2004/018587 Pamphlet JP 2003-68466 A JP 2005-132820 A JP 2005-174917 A International Publication No. 2006/049013 Pamphlet International Publication No. 03/059014 Pamphlet Japanese Patent Laid-Open No. 11-144866 Applied Physics Letters, 80 (17), 3201 (2002) Thin Solid Films, 436, 264 (2003)

  However, an organic electroluminescent device having sufficient performance with respect to heat resistance, driving voltage, light emission efficiency, current efficiency, device lifetime, external quantum efficiency, and the like has not yet been obtained using the organic materials described above. Under such circumstances, it is hoped to develop an organic electroluminescent device having higher performance in terms of heat resistance, driving voltage, luminous efficiency, current efficiency, device lifetime, external quantum efficiency, and the like, that is, a compound capable of obtaining the device. It is rare.

  Also, in order to cope with the mass production of full-color flat panel displays, it is necessary to develop a host material that has high performance and can be used simultaneously with fluorescence and phosphorescence.

  As a result of intensive studies to solve the above problems, the present inventors have succeeded in producing a benzocarbazole compound represented by the following general formula (1). In addition, by arranging an organic electroluminescent device by arranging the layer containing this benzocarbazole compound between a pair of electrodes, organicity improved in driving voltage, luminous efficiency, current efficiency, device lifetime, external quantum efficiency, etc. The inventors have found that an electroluminescent element can be obtained and completed the present invention.

  That is, the present invention provides the following benzocarbazole compound and an organic electroluminescence device using the same.

[1] A benzocarbazole compound represented by the following general formula (1).
(Where
Ar is aryl which may be substituted;
A ¹ , A ² and R ^{1 to} R ⁸ are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl, and A ^At least one of ¹ and A ² is an optionally substituted aryl. )

[2] Ar is an optionally substituted aryl having 6 to 30 carbon atoms,
A ¹ , A ² and R ^{1 to} R ⁸ are each independently hydrogen, optionally substituted alkyl having 1 to 24 carbon atoms, optionally substituted cycloalkyl having 3 to 12 carbon atoms, or substituted. And optionally substituted aryl having 6 to 30 carbon atoms, at least one of A ¹ and A ² is optionally substituted aryl having 6 to 30 carbon atoms, and
The substituents in Ar, A ¹ , A ² and R ^{1 to} R ⁸ are each independently alkyl having 1 to 24 carbons, cycloalkyl having 3 to 12 carbons, or aryl having 6 to 30 carbons.
The benzocarbazole compound described in [1] above.

[3] Ar is an optionally substituted aryl having 6 to 24 carbon atoms,
A ¹ and A ² are each independently an optionally substituted aryl having 6 to 24 carbon atoms,
R ^{1 to} R ⁸ are each independently hydrogen, an optionally substituted alkyl having 1 to 12 carbon atoms, an optionally substituted cycloalkyl having 3 to 10 carbon atoms, or an optionally substituted carbon. A number 6 to 24 aryl, and
The substituents in Ar, A ¹ , A ² and R ^{1 to} R ⁸ are each independently alkyl having 1 to 12 carbons, cycloalkyl having 5 to 8 carbons or aryl having 6 to 18 carbons.
The benzocarbazole compound described in [1] above.

[4] Ar is an optionally substituted aryl having 6 to 18 carbon atoms,
A ¹ and A ² are each independently an optionally substituted aryl having 6 to 18 carbon atoms,
R ^{1 to} R ⁸ are each independently hydrogen, optionally substituted alkyl having 1 to 6 carbon atoms, optionally substituted cycloalkyl having 5 to 8 carbon atoms, or optionally substituted carbon. A number 6-18 aryl, and
The substituents for Ar, A ¹ , A ² and R ^{1 to} R ⁸ are each independently alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, or aryl having 6 to 12 carbon atoms,
The benzocarbazole compound described in [1] above.

[5] Ar is phenyl, biphenylyl, terphenylyl, naphthyl or phenanthryl;
A ¹ and A ² are each independently phenyl, biphenylyl, terphenylyl, naphthyl or phenanthryl, and
R ^{1 to} R ⁸ are each independently hydrogen, methyl, ethyl, propyl, cyclopentyl, cyclohexyl, phenyl, biphenylyl, terphenylyl, naphthyl, or phenanthryl.
The benzocarbazole compound described in [1] above.

[6] Ar is phenyl or naphthyl;
A ¹ and A ² are each independently phenyl, biphenylyl or naphthyl, and
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound described in [1] above.

[7] Ar is optionally substituted aryl having 6 to 24 carbon atoms,
A ¹ and A ² are one of hydrogen and the other is optionally substituted aryl having 6 to 24 carbon atoms,
R ^{1 to} R ⁸ are each independently hydrogen, an optionally substituted alkyl having 1 to 12 carbon atoms, an optionally substituted cycloalkyl having 3 to 10 carbon atoms, or an optionally substituted carbon. A number 6 to 24 aryl, and
The substituents in Ar, A ¹ , A ² and R ^{1 to} R ⁸ are each independently alkyl having 1 to 12 carbons, cycloalkyl having 5 to 8 carbons or aryl having 6 to 18 carbons.
The benzocarbazole compound described in [1] above.

[8] Ar is optionally substituted aryl having 6 to 18 carbon atoms,
A ¹ and A ² are one of hydrogen and the other is optionally substituted aryl having 6 to 24 carbon atoms,
R ^{1 to} R ⁸ are each independently hydrogen, optionally substituted alkyl having 1 to 6 carbon atoms, optionally substituted cycloalkyl having 5 to 8 carbon atoms, or optionally substituted carbon. A number 6-18 aryl, and
The substituents for Ar, A ¹ , A ² and R ^{1 to} R ⁸ are each independently alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, or aryl having 6 to 12 carbon atoms,
The benzocarbazole compound described in [1] above.

[9] Ar is phenyl, biphenylyl, terphenylyl, naphthyl or phenanthryl;
A ¹ and A ² are one of hydrogen and the other is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl or phenanthryl, and
R ^{1 to} R ⁸ are each independently hydrogen, methyl, ethyl, propyl, cyclopentyl, cyclohexyl, phenyl, biphenylyl, terphenylyl, naphthyl, or phenanthryl.
The benzocarbazole compound described in [1] above.

[10] Ar is phenyl or naphthyl;
A ¹ and A ² are one of hydrogen, the other is phenyl, biphenylyl or naphthyl, and
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound described in [1] above.

[11] Ar is phenyl, A ¹ is phenyl, A ² is phenyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound described in [1] above.

[12] Ar is phenyl, A ¹ is 4-biphenylyl, A ² is 4-biphenylyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound described in [1] above.

[13] Ar is phenyl, A ¹ is 2-naphthyl, A ² is 2-naphthyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound described in [1] above.

[14] Ar is 2-naphthyl, A ¹ is phenyl, A ² is phenyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound described in [1] above.

[15] Ar is 2-naphthyl, A ¹ is 4-biphenylyl, A ² is 4-biphenylyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound described in [1] above.

[16] Ar is 2-naphthyl, A ¹ is 2-naphthyl, A ² is 2-naphthyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound described in [1] above.

[17] Ar is phenyl, A ¹ is phenyl, A ² is 4-biphenylyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound described in [1] above.

[18] Ar is phenyl, A ¹ is 4-biphenylyl, A ² is phenyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound described in [1] above.

[19] Ar is phenyl, A ¹ is phenyl, A ² is 2-naphthyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound described in [1] above.

[20] Ar is phenyl, A ¹ is 2-naphthyl, A ² is phenyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound described in [1] above.

[21] Ar is phenyl, A ¹ is 4-biphenylyl, A ² is 2-naphthyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound described in [1] above.

[22] Ar is phenyl, A ¹ is 2-naphthyl, A ² is 4-biphenylyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound described in [1] above.

[23] A material for a light-emitting layer of a light-emitting element, the material for a light-emitting layer containing the benzocarbazole compound according to any one of [1] to [22].

[24] The above [23], further comprising at least one selected from the group consisting of perylene derivatives, borane derivatives, amine-containing styryl derivatives, aromatic amine derivatives, coumarin derivatives, pyran derivatives, iridium complexes, and platinum complexes. The light emitting layer material described in 1.

[25] An organic electroluminescence device comprising a pair of electrodes composed of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes and containing the light-emitting layer material described in [23] or [24] .

[26] Furthermore, it has an electron transport layer and / or an electron injection layer arranged between the cathode and the light emitting layer, and at least one of the electron transport layer and the electron injection layer is a quinolinol-based metal complex, The organic electroluminescence device according to [25], which contains at least one selected from the group consisting of a pyridine derivative and a phenanthroline derivative.

[27] Furthermore, the electron transport layer and / or the electron injection layer disposed between the cathode and the light emitting layer are provided, and at least one of the electron transport layer and the electron injection layer includes a quinolinol-based metal complex. The organic electroluminescent element as described in [25] above.

[28] Furthermore, it has an electron transport layer and / or an electron injection layer arranged between the cathode and the light emitting layer, and at least one of the electron transport layer and the electron injection layer contains a pyridine derivative. The organic electroluminescent element as described in [25] above.

[29] Furthermore, it has an electron transport layer and / or an electron injection layer arranged between the cathode and the light emitting layer, and at least one of the electron transport layer and the electron injection layer contains a phenanthroline derivative. The organic electroluminescent element as described in [25] above.

[30] A display device comprising the organic electroluminescent element as described in any one of [25] to [29].

[31] A lighting device comprising the organic electroluminescent element as described in any one of [25] to [29].

  According to a preferred embodiment of the present invention, for example, a benzocarbazole compound having excellent characteristics as a light emitting layer material can be provided. Moreover, the organic electroluminescent element improved about heat resistance, drive voltage, luminous efficiency, current efficiency, element lifetime, external quantum efficiency, etc. can be provided. Furthermore, the benzocarbazole compound according to a preferred embodiment of the present invention has an advantage that it can be applied not only to phosphorescent devices but also to fluorescent devices. For example, the benzocarbazole compound according to a preferred embodiment of the present invention can be used as a host material for a red phosphorescent device and at the same time as a host material for a fluorescent blue device and a fluorescent green device. As a result, a material suitable for mass production of a full color flat panel display can be provided.

The benzocarbazole compound of the present invention will be described in detail.
The benzocarbazole compound according to the present invention is a benzocarbazole compound represented by the general formula (1).

1. The benzocarbazole compound represented by the general formula (1) First, the benzocarbazole compound represented by the general formula (1) will be described.

Examples of “aryl” of “optionally substituted aryl” in Ar, A ¹ , A ² and R ^{1 to} R ⁸ in the general formula (1) include aryl having 6 to 30 carbon atoms. The “aryl” of Ar is preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 18 carbon atoms, and still more preferably aryl having 6 to 12 carbon atoms. The “aryl” of A ¹ and A ² is preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 18 carbon atoms, and still more preferably an aryl having 6 to 12 carbon atoms. As "aryl" R ¹ to R ⁸ is preferably an aryl of 6 to 24 carbon atoms, more preferably 6 to 18 carbon atoms aryl, more preferably aryl having 6 to 12 carbon atoms.

  Specific “aryl” includes monocyclic aryl phenyl, (o-, m-, or p-) tolyl, (2,3-, 2,4-, 2,5-, 2,6- , 3,4-, or 3,5-) xylyl, mesityl, (o-, m-, or p-) cumenyl, bicyclic aryl (2-, 3-, or 4-) biphenylyl, fused di- Ring system aryl (1- or 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-) Yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl , M-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl- -Yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, or p-terphenyl-4-yl), a fused tricyclic aryl, acenaphthylene -(1-, 3-, 4-, or 5-) yl, fluorene- (1-, 2-, 3-, 4-, or 9-) yl, phenalen- (1- or 2-) yl, ( 1-, 2-, 3-, 4-, or 9-) phenanthryl, quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-) which is a tetracyclic aryl Terphenyl-3-yl, 5′-phenyl-m-terphenyl-4-yl, or m-quaterphenyl), triphenylene- (1- or 2-) yl which is a fused tetracyclic aryl, pyrene- ( 1-, 2-, or 4-) yl, naphthacene- (1-, -, Or 5-) yl, fused pentacyclic aryl perylene- (1-, 2-, or 3-) yl, pentacene- (1-, 2-, 5-, or 6-) yl It is done.

  Particularly preferred “aryl” in Ar is phenyl, biphenylyl, terphenylyl, naphthyl and phenanthryl, and among these, phenyl, 4-biphenylyl, 1-naphthyl, 2-naphthyl and 9-phenanthryl are preferred. When Ar is aryl, the benzocarbazole compound represented by the general formula (1) is characterized by increased rigidity, excellent heat resistance, and long life.

Particularly preferred “aryl” in A ¹ and A ² are phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl and phenanthryl, among which phenyl, 4-biphenylyl, 1-naphthyl, 2-naphthyl and 9 -Phenanthryl is preferred. A ¹ and A ² may be the same or different, and preferably A ¹ and A ² are the same. When A ¹ and A ² are aryl, the benzocarbazole compound represented by the general formula (1) is excellent in heat resistance, light emission efficiency, and lifetime.

Particularly preferable “aryl” in R ^{1 to} R ⁸ is phenyl, biphenylyl, naphthyl and phenanthryl, and among these, phenyl, 4-biphenylyl, 1-naphthyl and 2-naphthyl are preferable.

The “alkyl” of “optionally substituted alkyl” in A ¹ , A ² , and R ^{1 to} R ⁸ in the general formula (1) may be either a straight chain or a branched chain. Examples thereof include linear alkyl having 1 to 24 or branched alkyl having 3 to 24 carbon atoms. Preferred “alkyl” is alkyl having 1 to 18 carbons (branched alkyl having 3 to 18 carbons). More preferable “alkyl” is alkyl having 1 to 12 carbons (branched alkyl having 3 to 12 carbons). More preferable “alkyl” is alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). Particularly preferred “alkyl” is alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).

  Specific examples of “alkyl” include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1 -Methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2 -Propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-hept Decyl, n- octadecyl, such as n- eicosyl, and the like.

Examples of “cycloalkyl” of “optionally substituted cycloalkyl” in A ¹ , A ² and R ^{1 to} R ⁸ in the general formula (1) include cycloalkyl having 3 to 12 carbon atoms. . Preferred “cycloalkyl” is cycloalkyl having 3 to 10 carbon atoms. More preferred “cycloalkyl” is cycloalkyl having 5 to 8 carbon atoms. More preferred “cycloalkyl” is cycloalkyl having 5 to 6 carbon atoms.

  Specific examples of “cycloalkyl” include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

Examples of the “substituent” in Ar, A ¹ , A ² and R ^{1 to} R ⁸ in the general formula (1) include alkyl, cycloalkyl, and aryl. Preferred examples of these include A ¹ , A ² and those described in the “alkyl” column in R ^{1 to} R ⁸ , A ¹ , A ² , and those described in the “cycloalkyl” column in R ^{1 to} R ⁸ , Ar, A ¹ , A ² and the same as those described in the column of “aryl” in R ^{1 to} R ⁸ .

Specific examples of the “substituent” in Ar, A ¹ , A ² and R ^{1 to} R ⁸ include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, n-heptyl, n-octyl, t-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n- Alkyl such as tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl; cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl; phenyl, biphenylyl, naphthyl, terphenylyl, phenanthryl, etc. Of aryl; methylphenyl, ethylphenol And alkylaryl such as nyl, s-butylphenyl, t-butylphenyl, 1-methylnaphthyl, 2-methylnaphthyl, 1,6-dimethylnaphthyl, 2,6-dimethylnaphthyl and 4-t-butylnaphthyl. . The number of substituents is, for example, the maximum possible number of substitution, preferably 0-3, more preferably 0-2, and even more preferably 0 (unsubstituted).

From the viewpoint of material cost and ease of synthesis, R ^{1 to} R ⁸ are particularly preferably hydrogen. Similarly, A ¹ and A ² are preferably the same.

2. Specific examples of the compound represented by the general formula (1) As further specific examples of the compound represented by the general formula (1), for example, the compounds represented by the following formulas (1-1) to (1-174) Compounds.
Among the following compounds, in particular, the following formula (1-1), formula (1-3), formula (1-4), formula (1-7), formula (1-12), formula (1-13), Formula (1-14), Formula (1-19), Formula (1-21), Formula (1-23), Formula (1-24), Formula (1-25), Formula (1-29), Formula (1-31), Formula (1-34), Formula (1-35), Formula (1-41), Formula (1-44), Formula (1-45), Formula (1-49), Formula ( 1-59), Formula (1-61), Formula (1-63), Formula (1-65), Formula (1-79), Formula (1-80), Formula (1-82), Formula (1 -83), formula (1-84), formula (1-87), formula (1-90), formula (1-93), formula (1-101), formula (1-103), formula (1- 105), Formula (1-107), Formula (1-110), Formula (1-111), Formula (1-115), Formula (1-117), Formula (1-120), Formula (1-121 ), Formula (1-125), Formula (1-127), Formula (1-131), Formula (1-145), Formula (1-147), Formula (1-149), and Formula (1-151) The compound represented by these is preferable.
Furthermore, the following formula (1-1), formula (1-4), formula (1-7), formula (1-13), formula (1-14), formula (1-24), formula (1-29) , Formula (1-31), Formula (1-34), Formula (1-41), Formula (1-44), Formula (1-59), Formula (1-61), Formula (1-63), Formula (1-65), Formula (1-79), Formula (1-80), Formula (1-82), Formula (1-87), Formula (1-90), Formula (1-93) and Formula The compound represented by (1-101) is more preferable.

3. Production method of benzocarbazole compound represented by general formula (1) The benzocarbazole compound represented by general formula (1) can be produced by using a known synthesis method such as Suzuki coupling reaction, for example. it can. The Suzuki coupling reaction is a method of coupling an aromatic halide or triflate with an aromatic boronic acid or aromatic holonic acid ester using a palladium catalyst in the presence of a base. Specific examples of the reaction route for obtaining the compound represented by the general formula (1) by this method are as follows.
In the above formula, R ^{1 to} R ⁸ , A ¹ , A ² and Ar are the same as described above.

Specific examples of the palladium catalyst used in this reaction are Pd (PPh ₃ ) ₄ , PdCl ₂ (PPh ₃ ) ₂ , Pd (OAc) ₂ , tris (dibenzylideneacetone) dipalladium (0), tris (dibenzylideneacetone). ) Dipalladium (0) chloroform complex, bis (dibenzylideneacetone) palladium (0), and the like. In order to accelerate the reaction, a phosphine compound may be added to these palladium compounds in some cases. Specific examples of the phosphine compound include tri (t-butyl) phosphine, tricyclohexylphosphine, 1- (N, N-dimethylaminomethyl) -2- (di-t-butylphosphino) ferrocene, 1- (N, N -Dibutylaminomethyl) -2- (di-t-butylphosphino) ferrocene, 1- (methoxymethyl) -2- (di-t-butylphosphino) ferrocene, 1,1'-bis (di-t-butylphosphino) ) Ferrocene, 2,2′-bis (di-t-butylphosphino) -1,1′-binaphthyl, 2-methoxy-2 ′-(di-t-butylphosphino) -1,1′-binaphthyl and the like. .

  Specific examples of the base used in this reaction are sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, sodium hydroxide, potassium hydroxide, barium hydroxide, sodium ethoxide, sodium t-butoxide, sodium acetate, phosphoric acid. Tripotassium, potassium fluoride and the like.

  Furthermore, specific examples of the solvent used in this reaction are benzene, toluene, xylene, N, N-dimethylformamide, tetrahydrofuran, diethyl ether, t-butylmethyl ether, 1,4-dioxane, methanol, ethanol, Isopropyl alcohol and the like. These solvents can be appropriately selected according to the structure of the aromatic halide, triflate, aromatic holonic acid ester and aromatic boronic acid to be reacted. A solvent may be used independently and may be used as a mixed solvent.

  The benzocarbazole compound represented by the general formula (1) is a compound having strong fluorescence in a solid state and can be used for light emission of various colors, but is particularly suitable for blue light emission. Since the benzocarbazole compound represented by the general formula (1) has an asymmetric molecular structure, it is easy to form an amorphous state when manufacturing an organic EL element. In addition, it has excellent heat resistance and is stable when an electric field is applied.

  The benzocarbazole compound represented by the general formula (1) is effective as a host light emitting material. The benzocarbazole compound represented by the general formula (1) has a short emission wavelength and is particularly excellent as a fluorescent blue host light-emitting material, but can also be used for light emission other than blue light. The benzocarbazole compound represented by the general formula (1) is particularly effective as a phosphorescent host material. For example, when used as a host material of a red phosphorescent element, energy transfer to a red dopant is efficiently performed. As a result, a phosphorescent light emitting device with high efficiency and long life can be obtained.

  The benzocarbazole compound represented by the general formula (1) exhibits a stable glass state, and can form a stable amorphous film by vapor deposition or the like. Moreover, the solubility with respect to an organic solvent is large, and not only recrystallization and purification by column chromatography are easy, but also a free layer forming means can be employed when forming a layer of a light emitting element. For example, in general, in the layer formation by vapor deposition, there is a risk of decomposition of the compound or non-uniformity of the crystal structure of the formed layer, but the spin coating method is easily adopted using various solvents. Therefore, it is possible to form a layer that eliminates these fears.

4). Organic Electroluminescent Device The benzocarbazole compound according to the present invention can be used as a material for an organic electroluminescent device, for example.
The organic electroluminescent element according to this embodiment will be described in detail based on the drawings. FIG. 1 is a schematic cross-sectional view showing an organic electroluminescent element according to this embodiment.

<Structure of organic electroluminescence device>
An organic electroluminescent device 100 shown in FIG. 1 includes a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, and a hole injection layer 103. A hole transport layer 104 provided on the light-emitting layer 105, a light-emitting layer 105 provided on the hole-transport layer 104, a hole blocking layer 106 provided on the light-emitting layer 105, and a hole blocking layer 106 An electron transport layer 107 provided on the electron transport layer 107, an electron injection layer 108 provided on the electron transport layer 107, and a cathode 109 provided on the electron injection layer 108.

  The organic electroluminescent device 100 is manufactured in the reverse order, for example, the substrate 101, the cathode 109 provided on the substrate 101, the electron injection layer 108 provided on the cathode 109, and the electron injection layer. An electron transport layer 107 provided on the electron transport layer 108, a hole blocking layer 106 provided on the electron transport layer 107, a light emitting layer 105 provided on the hole blocking layer 106, The structure may include a hole transport layer 104 provided above, a hole injection layer 103 provided on the hole transport layer 104, and an anode 102 provided on the hole injection layer 103. .

  Not all of the above layers are necessary, and the minimum structural unit is composed of the anode 102, the light emitting layer 105, and the cathode 109, and the hole injection layer 103, the hole transport layer 104, the hole blocking layer 106, the electron The transport layer 107 and the electron injection layer 108 are provided arbitrarily. Moreover, each said layer may consist of a single layer, respectively, and may consist of multiple layers.

As an aspect of the layer constituting the organic electroluminescence device, the above-mentioned configuration of “substrate / anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode” Besides the aspect,
“Substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode”, “substrate / anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / "Cathode", "substrate / anode / hole injection layer / light emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron injection layer / cathode"", Substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode", "substrate / anode / light emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / Hole transport layer / light emitting layer / electron injection layer / cathode ”,“ substrate / anode / hole transport layer / light emitting layer / electron transport layer / cathode ”,“ substrate / anode / hole injection layer / light emitting layer / electron ” "Injection layer / cathode", "substrate / anode / hole injection layer / emission layer / electron transport layer / cathode", "substrate / anode / hole injection layer / hole transport layer / emission layer / cathode", "Substrate / anode / hole injection layer / light emitting layer / cathode", "substrate / anode / hole transport layer / light emitting layer / cathode", "substrate / anode / light emitting layer / electron transport layer / cathode", "substrate / anode / "Light emitting layer / electron injection layer / cathode" or "substrate / anode / light emitting layer / cathode".
Also, “substrate / anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode”, “substrate / anode / hole injection layer / hole transport layer / light emitting layer / "Hole blocking layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer" / Light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode ”,“ substrate / anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode ”,“ substrate / anode / Hole transport layer / light emitting layer / hole blocking layer / electron injection layer / cathode ”,“ substrate / anode / hole injection layer / light emitting layer / hole blocking layer / electron transport layer / cathode ”,“ substrate / anode / Hole injection layer / light emitting layer / hole blocking layer / electron injection layer / cathode ”,“ substrate / anode / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode ”,“ substrate / anode / positive Hole Incoming layer / hole transport layer / light emitting layer / hole blocking layer / cathode ”“ substrate / anode / hole injection layer / light emitting layer / hole blocking layer / cathode ”,“ substrate / anode / hole transport layer / light emitting ” Layer / hole blocking layer / cathode ”,“ substrate / anode / light emitting layer / hole blocking layer / electron transport layer / cathode ”,“ substrate / anode / light emitting layer / hole blocking layer / electron injection layer / cathode ”, The configuration of “substrate / anode / light emitting layer / hole blocking layer / cathode” may be used.

<Substrate in organic electroluminescence device>
The substrate 101 serves as a support for the organic electroluminescent device 100, and usually quartz, glass, metal, plastic, or the like is used. The substrate 101 is formed into a plate shape, a film shape, or a sheet shape according to the purpose. For example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used. Of these, glass plates and transparent synthetic resin plates such as polyester, polymethacrylate, polycarbonate, polysulfone and the like are preferable. In the case of a glass substrate, soda lime glass, non-alkali glass, or the like is used, and the thickness only needs to be sufficient to maintain the mechanical strength. The upper limit value of the thickness is, for example, 2 mm or less, preferably 1 mm or less. As for the material of the glass, non-alkali glass is preferred because it is better that there are fewer ions eluted from the glass, but soda-lime glass with a barrier coat such as SiO ₂ is also available on the market. it can. Further, the substrate 101 may be provided with a gas barrier film such as a dense silicon oxide film on at least one surface in order to improve the gas barrier property, and a synthetic resin plate, film or sheet having a particularly low gas barrier property is used as the substrate 101. When used, it is preferable to provide a gas barrier film.

<Anode in organic electroluminescence device>
The anode 102 serves to inject holes into the light emitting layer 105. When the hole injection layer 103 and / or the hole transport layer 104 are provided between the anode 102 and the light emitting layer 105, holes are injected into the light emitting layer 105 through these layers. .

  Examples of the material for forming the anode 102 include inorganic compounds and organic compounds. Examples of inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), etc.), halogenated compounds, etc. Examples thereof include metals (such as copper iodide), copper sulfide, carbon black, ITO glass, and nesa glass. Examples of the organic compound include polythiophene such as poly (3-methylthiophene), conductive polymer such as polypyrrole and polyaniline, and the like. In addition, it can select suitably from the substances currently used as an anode of an organic electroluminescent element, and can use it.

  The resistance of the transparent electrode is not limited as long as it can supply a sufficient current for light emission of the light emitting element, but is preferably low resistance from the viewpoint of power consumption of the light emitting element. For example, an ITO substrate of 300Ω / □ or less functions as an element electrode. However, since it is now possible to supply a substrate of about 10Ω / □, for example, 100-5Ω / □, preferably 50-5Ω. It is particularly desirable to use a low resistance product of / □. The thickness of ITO can be arbitrarily selected according to the resistance value, but is usually used in a range of 100 to 300 nm.

<Hole injection layer and hole transport layer in organic electroluminescence device>
The hole injection layer 103 plays a role of efficiently injecting holes moving from the anode 102 into the light emitting layer 105 or the hole transport layer 104. The hole transport layer 104 plays a role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 through the hole injection layer 103 to the light emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are each formed by laminating and mixing one or more hole injection / transport materials or a mixture of the hole injection / transport material and the polymer binder. Is done. In addition, an inorganic salt such as iron (III) chloride may be added to the hole injection / transport material to form a layer.

  As a hole injection / transport material, it is necessary to efficiently inject and transport holes from the positive electrode between electrodes to which an electric field is applied. The hole injection efficiency is high, and the injected holes are transported efficiently. It is desirable to do. For this purpose, it is preferable to use a substance that has a low ionization potential, a high hole mobility, excellent stability, and is less likely to generate trapping impurities during manufacturing and use.

  As a material for forming the hole injection layer 103 and the hole transport layer 104, in a photoconductive material, a compound conventionally used as a charge transport material for holes, a p-type semiconductor, and a hole injection of an organic electroluminescent element are used. Any known material used for the layer and the hole transport layer can be selected and used. Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis (N-allylcarbazole) or bis (N-alkylcarbazole), triarylamine derivatives (aromatic tertiary class). Polymer having amine in main chain or side chain, 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane, N, N′-diphenyl-N, N′-di (3-methylphenyl) -4 , 4'-diaminobiphenyl, N, N'-diphenyl-N, N'-dinaphthyl-4,4'-diaminobiphenyl (hereinafter abbreviated as NPD), N, N'-diphenyl-N, N'- Di (3-methylphenyl) -4,4′-diphenyl-1,1′-diamine, N, N′-dinaphthyl-N, N′-diphenyl-4 4'-diphenyl-1,1'-diamine, triphenylamine derivatives such as 4,4 ', 4 "-tris (3-methylphenyl (phenyl) amino) triphenylamine, starburst amine derivatives, stilbene derivatives, These are phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives, porphyrin derivatives, and other heterocyclic compounds, polysilanes, etc. Polycarbonate, styrene derivatives, polyvinyl carbazole, polysilane, and the like in the side chain are preferable, but any compound that can form a thin film necessary for manufacturing a light-emitting element, inject holes from the anode, and further transport holes can be used. It is not limited.

  It is also known that the conductivity of organic semiconductors is strongly influenced by the doping. Such an organic semiconductor matrix material is composed of a compound having a good electron donating property or a compound having a good electron accepting property. Strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known for doping of electron donor materials. (For example, the document “M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73 (22), 3202-3204 (1998)”) and the document “J. Blochwitz, M Pheiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73 (6), 729-731 (1998)). These generate so-called holes by an electron transfer process in an electron donating base material (hole transport material). Depending on the number and mobility of holes, the conductivity of the base material varies considerably. Known matrix substances having hole transporting properties include, for example, benzidine derivatives (TPD and the like), starburst amine derivatives (TDATA and the like), and specific metal phthalocyanines (particularly zinc phthalocyanine ZnPc and the like). 2005-167175).

<Light emitting layer in organic electroluminescent element>
The light emitting layer 105 emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 109 between electrodes to which an electric field is applied. The material for forming the light-emitting layer 105 may be a compound that emits light by being excited by recombination of holes and electrons (a light-emitting compound), can form a stable thin film shape, and is in a solid state It is preferable that the compound exhibits a strong light emission (fluorescence and / or phosphorescence) efficiency.

  The light emitting layer may be either a single layer or a plurality of layers, each formed of a light emitting material (host material, dopant material), which may be a mixture of a host material and a dopant material or a host material alone. Or either. That is, in each layer of the light emitting layer, only the host material or the dopant material may emit light, or both the host material and the dopant material may emit light. Each of the host material and the dopant material may be one kind or a plurality of combinations. The dopant material may be included in the host material as a whole, or may be included partially. The amount of the dopant used varies depending on the dopant, and may be determined according to the characteristics of the dopant (for example, if the amount used is too large, there is a risk of concentration quenching). The standard of the amount of the dopant used is preferably 0.001 to 50% by weight, more preferably 0.1 to 10% by weight, and further preferably 1 to 7% by weight of the entire light emitting material. As a doping method, it can be formed by a co-evaporation method with a host material, but it may be pre-mixed with the host material and then simultaneously deposited.

  In addition, the light emitting material of the light emitting element according to this embodiment may be either fluorescent or phosphorescent.

  As the host material, a benzocarbazole compound of the above general formula (1) can be used, and in particular, the above formula (1-1), formula (1-3), formula (1-4), formula (1-7) , Formula (1-12), Formula (1-13), Formula (1-14), Formula (1-19), Formula (1-21), Formula (1-23), Formula (1-24), Formula (1-25), Formula (1-29), Formula (1-31), Formula (1-34), Formula (1-35), Formula (1-41), Formula (1-44), Formula (1-45), Formula (1-49), Formula (1-59), Formula (1-61), Formula (1-63), Formula (1-65), Formula (1-79), Formula ( 1-80), Formula (1-82), Formula (1-83), Formula (1-84), Formula (1-87), Formula (1-90), Formula (1-93), Formula (1 -101), formula (1-103), formula (1-105), formula (1-107), formula (1-110), formula (1-111), formula (1-115), formula (1- 117), formula (1-120), formula (1-121), formula (1-125), formula (1-127), formula (1-131), formula (1-145), formula (1-147) ), Compounds represented by formula (1-149) and formula (1-151) are preferably used. Furthermore, the above formula (1-1), formula (1-4), formula (1-7), formula (1-13), formula (1-14), formula (1-24), formula (1-29) , Formula (1-31), Formula (1-34), Formula (1-41), Formula (1-44), Formula (1-59), Formula (1-61), Formula (1-63), Formula (1-65), Formula (1-79), Formula (1-80), Formula (1-82), Formula (1-87), Formula (1-90), Formula (1-93) and Formula It is more preferable to use the compound represented by (1-101). The content of the benzocarbazole compound represented by the general formula (1) in the light emitting layer 105 as a host material is preferably 1 to 100% by weight, more preferably 50 to 100% by weight, and particularly preferably 80 to 100% by weight. 90 to 100% by weight is particularly preferable.

  Other host materials include, but are not limited to, metal chelated oxinoid compounds such as fused ring derivatives such as anthracene and pyrene, tris (8-quinolinolato) aluminum, which have been known as light emitters. Bisstyryl derivatives such as bisstyryl anthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, coumarin derivatives, oxadiazole derivatives, pyrrolopyridine derivatives, perinone derivatives, cyclopentadiene derivatives, oxadiazole derivatives, thiadiazolopyridine derivatives, For pyrrolopyrrole derivatives and polymer systems, polyphenylene vinylene derivatives, polyparaphenylene derivatives, and polythiophene derivatives are preferably used.

  In addition, the host material can be appropriately selected from the compounds described in Chemical Industry, June 2004, page 13, and references cited therein.

  Moreover, it does not specifically limit as dopant material, A known compound can be used and it can select from various materials according to a desired luminescent color. Specifically, for example, condensed ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopylene, dibenzopyrene, and rubrene, benzoxazole derivatives, benzthiazole derivatives, benzimidazole derivatives, benztriazole derivatives, oxazole derivatives, Bisstyryl derivatives such as oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives and distyrylbenzene derivatives (Kaihei 1-245087), bisstyrylarylene derivatives (JP-A-2-247278), Isobenzofuran derivatives such as azaindacene derivatives, furan derivatives, benzofuran derivatives, phenylisobenzofuran, dimesitylisobenzofuran, di (2-methylphenyl) isobenzofuran, di (2-trifluoromethylphenyl) isobenzofuran, phenylisobenzofuran, Dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzthiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives Derivatives, coumarin derivatives such as 3-benzoxazolyl coumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives Oxobenzanthracene derivatives, xanthene derivatives, rhodamine derivatives, fluorescein derivatives, pyrylium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2,5 -Organic metals such as thiadiazolopyrene derivatives, pyromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, zinc, aluminum, beryllium, europium, terbium, dysprosium, iridium, platinum Complex.

  Illustratively for each color light, blue to blue-green dopant materials include naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene and other aromatic hydrocarbon compounds and derivatives thereof, furan, pyrrole, thiophene, silole, Aromatic heterocyclic compounds such as 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, thioxanthene And its derivatives, distyrylbenzene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, imidazole, thiazole, thiadiazole, cal Azole derivatives such as sol, oxazole, oxadiazole, triazole and metal complexes thereof, and N, N′-diphenyl-N, N′-di (3-methylphenyl) -4,4′-diphenyl-1,1′- Examples thereof include aromatic amine derivatives represented by diamine.

  Examples of green to yellow dopant materials include coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridone derivatives, quinacridone derivatives, and naphthacene derivatives such as rubrene. A compound in which a substituent capable of increasing the wavelength such as an aryl group, a heteroaryl group, an arylvinyl group, an amino group, or a cyano group is introduced into the compound exemplified as the blue-green dopant material is also a suitable example.

  Further, examples of the orange to red dopant material include naphthalimide derivatives such as bis (diisopropylphenyl) perylenetetracarboxylic imide, perinone derivatives, rare earth complexes such as Eu complexes having acetylacetone, benzoylacetone and phenanthroline as ligands, 4 -(Dicyanomethylene) -2-methyl-6- (p-dimethylaminostyryl) -4H-pyran and its analogs, metal phthalocyanine derivatives such as magnesium phthalocyanine and aluminum chlorophthalocyanine, rhodamine compounds, deazaflavin derivatives, coumarin derivatives, quinacridone Derivatives, phenoxazine derivatives, oxazine derivatives, quinazoline derivatives, pyrrolopyridine derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, phenoxazones Conductors and thiadiazolopyrene derivatives, etc., and further increase the wavelength of aryl, heteroaryl, arylvinyl, amino, and cyano groups to the compounds exemplified as the blue-blue-green and green-yellow dopant materials. A compound into which a substituent is introduced is also a suitable example. Furthermore, a phosphorescent metal complex having iridium represented by tris (2-phenylpyridine) iridium (III) or platinum as a central metal is also a suitable example.

  As dopant materials suitable for the material for the light emitting layer of the present invention, among the above-mentioned dopant materials, perylene derivatives, borane derivatives, amine-containing styryl derivatives, aromatic amine derivatives, coumarin derivatives, pyran derivatives, iridium complexes, or platinum complexes Is preferred.

Examples of perylene derivatives include 3,10-bis (2,6-dimethylphenyl) perylene, 3,10-bis (2,4,6-trimethylphenyl) perylene, 3,10-diphenylperylene, 3,4- Diphenylperylene, 2,5,8,11-tetra-t-butylperylene, 3,4,9,10-tetraphenylperylene, 3- (1'-pyrenyl) -8,11-di (t-butyl) perylene 3- (9′-anthryl) -8,11-di (t-butyl) perylene, 3,3′-bis (8,11-di (t-butyl) perylenyl), and the like.
JP-A-11-97178, JP-A-2000-133457, JP-A-2000-26324, JP-A-2001-267079, JP-A-2001-267078, JP-A-2001-267076, Perylene derivatives described in JP 2000-34234 A, JP 2001-267075 A, JP 2001-217077 A and the like may be used.

Examples of the borane derivative include 1,8-diphenyl-10- (dimesitylboryl) anthracene, 9-phenyl-10- (dimesitylboryl) anthracene, 4- (9′-anthryl) dimesitylborylnaphthalene, 4- (10 ′). -Phenyl-9'-anthryl) dimesitylborylnaphthalene, 9- (dimesitylboryl) anthracene, 9- (4'-biphenylyl) -10- (dimesitylboryl) anthracene, 9- (4 '-(N-carbazolyl) phenyl) -10- (Dimesitylboryl) anthracene and the like.
Moreover, you may use the borane derivative described in the international publication 2000/40586 pamphlet.

  Examples of the amine-containing styryl derivative include N, N, N ′, N′-tetra (4-biphenylyl) -4,4′-diaminostilbene, N, N, N ′, N′-tetra (1-naphthyl). -4,4'-diaminostilbene, N, N, N ', N'-tetra (2-naphthyl) -4,4'-diaminostilbene, N, N'-di (2-naphthyl) -N, N' -Diphenyl-4,4'-diaminostilbene, N, N'-di (9-phenanthryl) -N, N'-diphenyl-4,4'-diaminostilbene, 4,4'-bis [4 "-bis ( Diphenylamino) styryl] -biphenyl, 1,4-bis [4′-bis (diphenylamino) styryl] -benzene, 2,7-bis [4′-bis (diphenylamino) styryl] -9,9-dimethylfluorene , 4,4'-bis ( -Ethyl-3-carbazovinylene) -biphenyl, 4,4′-bis (9-phenyl-3-carbazovinylene) -biphenyl, etc. JP-A 2003-347056 and JP-A 2001-307884 Amine-containing styryl derivatives described in the above may be used.

Examples of the aromatic amine derivative include N, N, N, N-tetraphenylanthracene-9,10-diamine, 9,10-bis (4-diphenylamino-phenyl) anthracene, and 9,10-bis (4- Di (1-naphthylamino) phenyl) anthracene, 9,10-bis (4-di (2-naphthylamino) phenyl) anthracene, 10-di-p-tolylamino-9- (4-di-p-tolylamino-1) -Naphthyl) anthracene, 10-diphenylamino-9- (4-diphenylamino-1-naphthyl) anthracene, 10-diphenylamino-9- (6-diphenylamino-2-naphthyl) anthracene, [4- (4-diphenyl) Amino-phenyl) naphthalen-1-yl] -diphenylamine, [4- (4-diphenylamino-phenyl) na Talen-1-yl] -diphenylamine, [6- (4-diphenylamino-phenyl) naphthalen-2-yl] -diphenylamine, 4,4′-bis [4-diphenylaminonaphthalen-1-yl] biphenyl, 4, 4'-bis [6-diphenylaminonaphthalen-2-yl] biphenyl, 4,4 "-bis [4-diphenylaminonaphthalen-1-yl] -p-terphenyl, 4,4" -bis [6-diphenyl Aminonaphthalen-2-yl] -p-terphenyl and the like.
Moreover, you may use the aromatic amine derivative described in Unexamined-Japanese-Patent No. 2006-156888.
Examples of the aromatic amine derivative include compounds represented by the following D1.

Examples of the coumarin derivative include coumarin-6 and coumarin-334.
Moreover, you may use the coumarin derivative described in Unexamined-Japanese-Patent No. 2004-43646, Unexamined-Japanese-Patent No. 2001-76876, and Unexamined-Japanese-Patent No. 6-298758.

Examples of the pyran derivative include the following DCM and DCJTB.
JP-A-2005-126399, JP-A-2005-097283, JP-A-2002-234892, JP-A-2001-220577, JP-A-2001-081090, and JP-A-2001-052869 The pyran derivatives described in the above may be used.

Examples of the iridium complex include tris (1-phenylisoquinoline) iridium (III) (Ir (piq) ₃ ), bis (1-phenylisoquinoline) acetylacetonatoiridium (III) (Ir (piq) ₂ (acac)), tris (2-Phenylpyridine) iridium (III) (Ir (ppy) ₃ ), tris (2- (4-tolyl) pyridine) iridium (III) (Ir (ppy) ₃ ), bis (3-methyldibenzo [f. h] quinoxaline) acetylacetonatoiridium (III), bis (dibenzo [f.h] quinoxaline) acetylacetonatoiridium (III), tris (2-phenylquinoline) iridium (III) (Ir (pq) ₃ ), bis (2-phenylquinoline) acetylacetonate iridium (III) (Ir (pq) 2 (acac)), tri (2-benzothiophen-2-yl - pyridine) iridium (III) (Ir (btpy) 3), bis (2-benzothiophen-2-yl - pyridine) acetylacetonate Iridium (III) (Ir (btpy) 2 (Acac)), bis (1- (9,9-dimethyl-9H-fluoren-2-yl) -isoquinoline) iridium (III), bis (3- (9,9-dimethyl-9H-fluoren-2-yl) ) -Isoquinoline) iridium (III), bis (2- (9,9-dimethyl-9H-fluoren-2-yl) -quinoline) iridium (III), bis (benzo [h] quinoline) acetylacetonatoiridium (III) ), Bis (benzo [h] isoquinoline) acetylacetonatoiridium (III), bis (2-thienylpyridine) acetylacetonatolylid Um (III).
Also, JP 2006-089398 A, JP 2006-080419 A, JP 2006-290988 A, JP 2005-298483 A, JP 2005-097263 A, and JP 2004-111379 A. The iridium complex described in the above may be used.

Examples of the platinum complex include bis (2-phenylpyridine) platinum, octaethylplatinum porphyrin (PtOEP), and octaphenylplatinum porphyrin.
Also, JP-A-2006-190718, JP-A-2006-128634, JP-A-2006-093542, JP-A-2006-232784, JP-A-2004-335122, and JP-A-2004-331508 are disclosed. Platinum complexes described in International Publication No. 2004/039914 pamphlet and the like may be used.

  In addition, as a dopant, it can select and use suitably from the compound etc. which were described in the chemical industry June, 2004 issue page 13, and the reference literature etc. which were raised to it.

<Hole blocking layer in organic electroluminescence device>
The hole blocking layer 106 serves to confine holes and electrons in the light emitting layer 105 and improve the light emission efficiency. The hole blocking layer 106 is a substance that prevents holes moving from the anode 102 from reaching the cathode 109 and efficiently transports electrons injected from the cathode 109 toward the light emitting layer 105. It is desirable. That is, the material forming the hole blocking layer 106 is required to have a property of high electron mobility and low hole mobility in order to improve the light emission efficiency. In addition, high driving stability is also required from the demand for extending the life of organic electroluminescent elements.

  Specifically, organometallic complexes (mixed ligand complexes, binuclear metal complexes, etc.), styryl compounds (distyryl biphenyl derivatives, etc.), triazole derivatives, phenanthroline derivatives, borane derivatives, and anthracene derivatives (for example, JP-A 2006-2006 No. 049570) and the like. These materials can be used alone or in combination with different materials.

  Among these, organometallic complexes (such as mixed ligand complexes and binuclear metal complexes), phenanthroline derivatives, and borane derivatives are preferable.

  Examples of organometallic complexes (mixed ligand complexes, binuclear metal complexes, etc.) include bis (2-methyl-8-quinolinolato) (phenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-methyl). Phenolate) aluminum, bis (2-methyl-8-quinolinolato) (3-methylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (4-methylphenolate) aluminum, bis (2-methyl-8) -Quinolinolato) (2-phenylphenolato) aluminum, bis (2-methyl-8-quinolinolato) (3-phenylphenolato) aluminum, bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum ( Hereinafter, abbreviated as Balq.), Bis (2-methyl-8-quinoli) Lat) (2,3-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,6-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3,4-dimethyl) Phenolate) aluminum, bis (2-methyl-8-quinolinolato) (3,5-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3,5-di-t-butylphenolate) aluminum Bis (2-methyl-8-quinolinolato) (2,4-diphenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,5-diphenylphenolato) aluminum, bis (2-methyl-8) -Quinolinolato) (2,6-diphenylphenolate) aluminum, bis (2- Til-8-quinolinolato) (2,4,6-triphenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,4,6-trimethylphenolato) aluminum, bis (2-methyl-8) -Quinolinolato) (2,4,5,6-tetramethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinolato) (2-naphtholate) ) Aluminum, bis (2,4-dimethyl-8-quinolinolato) (2-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolato) (3-phenylphenolato) aluminum, bis (2,4 -Dimethyl-8-quinolinolato) (4-phenylphenolato) aluminum Bis (2,4-dimethyl-8-quinolinolato) (3,5-dimethylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolato) (3,5-di-t-butylphenolate) aluminum Bis (2-methyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum, bis (2,4-dimethyl-8-quinolinolato) aluminum-μ-oxo-bis (2 , 4-Dimethyl-8-quinolinolato) aluminum, bis (2-methyl-4-ethyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-4-ethyl-8-quinolinolato) aluminum, bis (2 -Methyl-4-methoxy-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl- -Methoxy-8-quinolinolato) aluminum, bis (2-methyl-5-cyano-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-5-cyano-8-quinolinolato) aluminum, bis (2-methyl -5-trifluoromethyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum.

  Examples of phenanthroline derivatives include 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (hereinafter abbreviated as BCP), 2,4,9, 7-tetraphenyl-1,10-phenanthroline, 9,10-di (1,10-phenanthrolin-2-yl) anthracene, 2,6-di (1,10-phenanthroline-5-yl) pyridine, 1,3 , 5-tri (1,10-phenanthroline-5-yl) benzene, 1,3-bis (2-phenyl-1,10-phenanthroline-9-yl) benzene and the like.

Examples of the borane derivative include 9- (4′-dimesitylborylbiphenyl-4-yl) -9H-carbazole, 9- (4- (4-dimesitylborylnaphthalen-1-yl) phenyl) -9H. -Carbazole, 9- (4- (4-dimesitylborylphenyl) naphthalen-1-yl) -9H-carbazole, 9- (4- (6-dimesitylborylnaphthalen-2-yl) phenyl) -9H -Carbazole, 9- (6- (4-Dimesitylborylphenyl) naphthalen-2-yl) -9H-carbazole, 9- (7-Dimesitylboryl-9,9-dimethyl-9H-fluoren-2-yl)- 9H-carbazole, 9- (7-dimesitylboryl-9,9-diphenyl-9H-fluoren-2-yl) -9H-carbazole, 4,4′-bis (dimesitylbo) B) Biphenyl, 1-Dimesitylboryl-4- (4-Dimesitylborylphenyl) naphthalene, 2-Dimesitylboryl-6- (4-Dimesitylborylphenyl) naphthalene, 2,7-bis (Dimesitylboryl) -9,9 -Dimethyl-9H-fluorene, 2,7-bis (dimesitylboryl) -9,9-diphenyl-9H-fluorene and the like.
Further, a borane derivative described in Japanese Patent Application No. 2005-210638 may be used.

<Electron injection layer and electron transport layer in organic electroluminescence device>
The electron injection layer 108 plays a role of efficiently injecting electrons moving from the cathode 109 into the light emitting layer 105, the hole blocking layer 106, or the electron transport layer 107. The electron transport layer 107 plays a role of efficiently transporting electrons injected from the cathode 109 or electrons injected from the cathode 109 through the electron injection layer 108 into the light emitting layer 105 or the hole blocking layer 106. is there. The electron transport layer 107 and the electron injection layer 108 are each formed by laminating and mixing one or more electron transport / injection materials, or a mixture of the electron transport / injection material and the polymer binder.

  The electron injecting / transporting layer is a layer that administers electrons injected from the cathode and further transports electrons. It is desirable that the electron injecting electrons have high efficiency and efficiently transport the injected electrons. For this purpose, it is preferable to use a substance that has a high electron affinity, a high electron mobility, excellent stability, and is unlikely to generate trapping impurities during production and use.

  Materials used for the electron transport layer and the electron injection layer include compounds conventionally used as electron transport compounds in photoconductive materials, and known compounds used for the electron injection layer and the electron transport layer of organic electroluminescence devices. Any of these can be selected and used.

  Specifically, pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, thiophene derivatives, thiadiazole derivatives, quinoxaline derivatives, quinoxaline Derivative polymers, benzazole compounds, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, imidazopyridine derivatives, borane derivatives, benzoxazole derivatives, benzthiazole derivatives, quinoline derivatives, aldazine derivatives, carbazole derivatives, indole derivatives, Examples thereof include phosphorus oxide derivatives and bisstyryl derivatives. In addition, oxadiazole derivatives (1,3-bis [(4-t-butylphenyl) 1,3,4-oxadiazolyl] phenylene, etc.), triazole derivatives (N-naphthyl-2,5-diphenyl-1,3, etc.) 4-triazole, etc.), benzoquinoline derivatives (2,2′-bis (benzo [h] quinolin-2-yl) -9,9′-spirobifluorene, etc.), benzimidazole derivatives (tris (N-phenylbenzimidazole, etc.) -2-yl) benzene), bipyridine derivatives, terpyridine derivatives (1,3-bis (4 ′-(2,2 ′: 6′2 ″ -terpyridine)) benzene, etc.), naphthyridine derivatives (bis (1-naphthyl) ) -4- (1,8-naphthyridin-2-yl) phenylphosphine oxide, etc.) These materials are used alone. Is also used, it may be used in admixture with different materials.

  In addition, a metal complex having an electron-accepting nitrogen can be used, for example, a hydroxyazole complex such as a quinolinol-based metal complex or a hydroxyphenyloxazole complex, an azomethine complex, a tropolone metal complex, a flavonol metal complex, or a benzoquinoline metal complex. can give. These materials can be used alone or in combination with different materials.

  Among these, quinolinol-based metal complexes, pyridine derivatives, or phenanthroline derivatives are preferable. In particular, when a pyridine derivative or a phenanthroline derivative is used for the electron transport layer or the electron injection layer, low voltage and high efficiency can be realized.

The quinolinol-based metal complex is a compound represented by the following general formula (E-1).
In the formula, R _{1 to} R ₆ are hydrogen or a substituent, M is Al, Ga, Be, or Zn, and n is an integer of 2 or 3.

  Specific examples of the quinolinol-based metal complex include tris (8-quinolinolato) aluminum (hereinafter abbreviated as ALQ), tris (4-methyl-8-quinolinolato) aluminum, and tris (5-methyl-8-quinolinolato) aluminum. , Tris (3,4-dimethyl-8-quinolinolato) aluminum, tris (4,5-dimethyl-8-quinolinolato) aluminum, tris (4,6-dimethyl-8-quinolinolato) aluminum, bis (2-methyl-8) -Quinolinolato) (phenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-methylphenolato) aluminum, bis (2-methyl-8-quinolinolato) (3-methylphenolato) aluminum, bis (2- Methyl-8-quinolinolate) (4- Tylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3-phenylphenolate) aluminum, bis (2-methyl- 8-quinolinolato) (4-phenylphenolato) aluminum, bis (2-methyl-8-quinolinolato) (2,3-dimethylphenolato) aluminum, bis (2-methyl-8-quinolinolato) (2,6-dimethyl) Phenolate) aluminum, bis (2-methyl-8-quinolinolato) (3,4-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3,5-dimethylphenolate) aluminum, bis (2 -Methyl-8-quinolinolate) (3,5-di-t- Tylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,6-diphenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,4,6-triphenylphenolate) aluminum Bis (2-methyl-8-quinolinolato) (2,4,6-trimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,4,5,6-tetramethylphenolato) aluminum, Bis (2-methyl-8-quinolinolato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinolato) (2-naphtholato) aluminum, bis (2,4-dimethyl-8-quinolinolato) (2-phenyl) Phenolate) aluminum, bis (2,4-dimethyl-8-quinolinola) G) (3-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolato) (4-phenylphenolato) aluminum, bis (2,4-dimethyl-8-quinolinolato) (3,5-dimethyl) Phenolate) aluminum, bis (2,4-dimethyl-8-quinolinolato) (3,5-di-t-butylphenolate) aluminum, bis (2-methyl-8-quinolinolato) aluminum-μ-oxo-bis ( 2-methyl-8-quinolinolato) aluminum, bis (2,4-dimethyl-8-quinolinolato) aluminum-μ-oxo-bis (2,4-dimethyl-8-quinolinolato) aluminum, bis (2-methyl-4- Ethyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-4-ethyl-) -Quinolinolato) aluminum, bis (2-methyl-4-methoxy-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-4-methoxy-8-quinolinolato) aluminum, bis (2-methyl-5-cyano) -8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-5-cyano-8-quinolinolato) aluminum, bis (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum, bis (10-hydroxybenzo [h] quinoline) beryllium and the like.

The pyridine derivative is a compound represented by the following general formula (E-2-1) or (E-2-2).
In the formula, R _{1 to} R ₅ are hydrogen or a substituent, adjacent groups may be bonded to each other to form a condensed ring, G represents a simple bond or an n-valent linking group, and n represents 2 It is an integer of ~ 8.

Examples of G in the general formula (E-2-2) include the following structural formulas. In addition, R in the following structural formula is each independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl or 2-naphthyl.

  Specific examples of the pyridine derivative include 2,5-bis (2,2′-bipyridyl-6-yl) -1,1-dimethyl-3,4-diphenylsilole, 2,5-bis (2,2′- Bipyridyl-6-yl) -1,1-dimethyl-3,4-dimesitylsilole, 9,10-di (2,2′-bipyridyl-6-yl) anthracene, 9,10-di (2,2 '-Bipyridyl-5-yl) anthracene, 9,10-di (2,3'-bipyridyl-6-yl) anthracene, 9,10-di (2,3'-bipyridyl-5-yl) -2-phenyl Anthracene, 9,10-di (2,2′-bipyridyl-5-yl) -2-phenylanthracene, 3,4-diphenyl-2,5-di (2,2′-bipyridyl-6-yl) thiophene, 3,4-diphenyl-2,5-di (2,3′- Pyridyl-5-yl) thiophene, 6'6 "- di (2-pyridyl) 2,2 ': 4', 4": 2 ", 2" '- like quaterphenyl pyridine.

The phenanthroline derivative is a compound represented by the following general formula (E-3-1) or (E-3-2).
In the formula, R _{1 to} R ₅ are hydrogen or a substituent, adjacent groups may be bonded to each other to form a condensed ring, G represents a simple bond or an n-valent linking group, and n represents 2 It is an integer of ~ 8. Examples of G in the general formula (E-3-2) include the same ones as described in the column of pyridine derivatives.

  Specific examples of the phenanthroline derivative include 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 2,4,9,7-tetraphenyl-1, 10-phenanthroline, 9,10-di (1,10-phenanthroline-2-yl) anthracene, 2,6-di (1,10-phenanthroline-5-yl) pyridine, 1,3,5-tri (1, And 10-phenanthroline-5-yl) benzene and 1,3-bis (2-phenyl-1,10-phenanthroline-9-yl) benzene.

  In particular, the case where a phenanthroline derivative is used for an electron transport layer and an electron injection layer will be described. In order to obtain stable light emission over a long period of time, a material excellent in thermal stability and thin film formation is desired, and among phenanthroline derivatives, the substituent itself has a three-dimensional structure, or a phenanthroline skeleton or Those having a three-dimensional structure by steric repulsion with an adjacent substituent or those having a plurality of phenanthroline skeletons linked to each other are preferred. Furthermore, when linking a plurality of phenanthroline skeletons, a compound containing a conjugated bond, a substituted or unsubstituted aromatic hydrocarbon, or a substituted or unsubstituted aromatic heterocycle in the linking unit is more preferable.

<Cathode in organic electroluminescence device>
The cathode 109 plays a role of injecting electrons into the light emitting layer 105 through the electron injection layer 108, the electron transport layer 107 and / or the hole blocking layer 106.

  The material for forming the cathode 109 is not particularly limited as long as it can efficiently inject electrons into the organic layer, but the same material as that for forming the anode 102 can be used. Among them, metals such as tin, magnesium, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium and magnesium or alloys thereof (magnesium-silver alloy) , Magnesium-indium alloys, aluminum-lithium alloys such as lithium fluoride / aluminum) are preferred. Lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective for increasing the electron injection efficiency and improving device characteristics. However, these low work function metals are generally unstable in the atmosphere. For example, the organic layer is doped with a small amount of lithium, cesium, or magnesium (1 nm or less in vacuum vapor deposition thickness gauge display). Although a method using a highly stable electrode can be given as a preferred example, it is particularly limited to these because inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide and cesium oxide can also be used. It is not something.

  Furthermore, for electrode protection, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys using these metals, and inorganic substances such as silica, titania and silicon nitride, polyvinyl alcohol, vinyl chloride Lamination of hydrocarbon polymer compounds and the like is a preferred example. The method for producing these electrodes is not particularly limited as long as conduction can be achieved, such as resistance heating, electron beam, sputtering, ion plating, and coating.

<Binder that may be used in each layer>
The materials used for the above hole injection layer, hole transport layer, light emitting layer, hole blocking layer, electron transport layer and electron injection layer can form each layer alone, but as a polymer binder, Vinyl chloride, polycarbonate, polystyrene, poly (N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polysulfone, polyamide, ethyl cellulose, acetic acid For solvent-soluble resins such as vinyl resin, ABS resin, polyurethane resin, and curable resins such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, etc. Decentralized It is also possible to use Te.

<Method for producing organic electroluminescent element>
Each layer constituting the organic electroluminescent element is formed by a method such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, printing method, spin coating method or cast method, coating method, etc. It can be formed by using a thin film. The thickness of each layer formed in this way is not particularly limited and can be appropriately set according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured with a crystal oscillation type film thickness measuring device or the like. When a thin film is formed using a vapor deposition method, the vapor deposition conditions vary depending on the type of material, the target crystal structure and association structure of the film, and the like. Deposition conditions generally include boat heating temperature of 50 to 400 ° C., vacuum degree of 10 ⁻⁶ to 10 ⁻³ Pa, deposition rate of 0.01 to 50 nm / second, substrate temperature of −150 to + 300 ° C., and film thickness of 2 nm to 5 μm. It is preferable to set appropriately within the range.

  Next, as an example of a method for producing an organic electroluminescent device, anode / hole injection layer / hole transport layer / light emitting layer comprising a host material and a dopant material / hole blocking layer / electron transport layer / electron injection layer / A method for producing an organic electroluminescent element comprising a cathode will be described. A thin film of an anode material is formed on a suitable substrate by vapor deposition or the like to produce an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. A thin film is formed by co-evaporating a host material and a dopant material thereon to form a light emitting layer. A hole blocking layer, an electron transport layer, an electron injection layer are formed on the light emitting layer, and a thin film made of a cathode material. Is formed by a vapor deposition method or the like to form a cathode, thereby obtaining a target organic electroluminescent element. In the production of the organic electroluminescence device described above, the production order was reversed, and the cathode, electron injection layer, electron transport layer, hole blocking layer, light emitting layer, hole transport layer, hole injection layer, anode It is also possible to produce in order.

  When a DC voltage is applied to the organic electroluminescent device thus obtained, the anode may be applied with a positive polarity and the cathode with a negative polarity. When a voltage of about 2 to 40 V is applied, the organic electroluminescent device is transparent or translucent. Luminescence can be observed from the electrode side (anode or cathode and both). The organic electroluminescence device emits light when a pulse current or an alternating current is applied. The alternating current waveform to be applied may be arbitrary.

<Application examples of organic electroluminescent devices>
The present invention can also be applied to a display device including an organic electroluminescent element or a lighting device including an organic electroluminescent element.
The display device or the illumination device including the organic electroluminescent element can be manufactured by a known method such as connecting the organic electroluminescent element according to the present embodiment and a known driving device, such as direct current driving, pulse driving, or alternating current. It can be driven by appropriately using a known driving method such as driving.

  Examples of the display device include a panel display such as a color flat panel display, and a flexible display such as a flexible color organic electroluminescence (EL) display (for example, JP-A-10-335066 and JP-A-2003-321546). Gazette, Japanese Patent Application Laid-Open No. 2004-281086, etc.). Examples of the display method of the display include a matrix and / or segment method. Note that the matrix display and the segment display may coexist in the same panel.

  A matrix means a pixel in which pixels for display are two-dimensionally arranged such as a lattice or a mosaic, and displays a character or an image with a set of pixels. The shape and size of the pixel are determined by the application. For example, a square pixel with a side of 300 μm or less is usually used for displaying images and characters on a personal computer, monitor, TV, and a pixel with a side of mm order for a large display such as a display panel. become. In monochrome display, pixels of the same color may be arranged. However, in color display, red, green, and blue pixels are displayed side by side. In this case, there are typically a delta type and a stripe type. The matrix driving method may be either a line sequential driving method or an active matrix. The line-sequential driving has the advantage of a simple structure. However, the active matrix may be superior in consideration of the operating characteristics, so it is necessary to use it depending on the application.

  In the segment method (type), a pattern is formed so as to display predetermined information, and a predetermined region is caused to emit light. For example, the time and temperature display in a digital clock or a thermometer, the operation state display of an audio device or an electromagnetic cooker, the panel display of an automobile, and the like can be mentioned.

  Examples of the illuminating device include an illuminating device such as indoor lighting, a backlight of a liquid crystal display device, and the like (for example, Japanese Patent Application Laid-Open Nos. 2003-257621, 2003-277741, and 2004-119211). Etc.) The backlight is used mainly for the purpose of improving the visibility of a display device that does not emit light, and is used for a liquid crystal display device, a clock, an audio device, an automobile panel, a display board, a sign, and the like. In particular, as a backlight for liquid crystal display devices, especially personal computers for which thinning is an issue, considering that conventional methods are made of fluorescent lamps and light guide plates, it is difficult to reduce the thickness. The backlight using the light emitting element according to the embodiment is thin and lightweight.

<Synthesis example of benzocarbazole compound>
Hereinafter, synthesis examples of the compound (1-13) will be described.

<Synthesis Example of Compound (1-13)>
Under nitrogen atmosphere, trifluoromethanesulfonic acid-7-phenyl-9-trifluoromethanesulfonyloxy-7H-benzo [c] carbazol-5-yl ester ( 5.9 g ) and 2- naphthaleneboronic acid ( 4.1 g ) in tetrahydrofuran And isopropyl alcohol ( 125 ml , tetrahydrofuran / isopropyl alcohol = 1/4), tetrakis (triphenylphosphine) palladium (0) ( 1.2 g ) was added and stirred for 5 minutes, and then potassium phosphate ( 12.7 g ) was added and refluxed for 4 hours. After the reaction, 60 ml of the solvent was removed. 100 ml of water was added and the precipitate was filtered. The precipitate was further washed with water and methanol to obtain a crude product of compound (1-13). The crude product was subjected to column purification with silica gel (solvent: heptane / toluene = 3/1), recrystallized with toluene, and then purified by sublimation to obtain 4.0 g of the desired compound (1-13). (Yield: 73.3%) was obtained. The structure of the compound (1-13) was confirmed by MS spectrum and NMR measurement.
¹ H-NMR (CDCl ₃ ): δ = 8.98 (d, 1H), 8.77 (d, 1H), 8.13 (s, 1H), 8.05 to 7.76 (m, 12H) , 7.68-7.44 (m, 12H) .
Other physical properties were as follows.
Glass transition temperature (Tg): 121 ° C. [Measuring instrument: Diamond DSC (manufactured by PERKIN-ELMER); Measurement conditions: cooling rate 200 ° C./Min., Temperature rising rate 10 ° C./Min.]

  By appropriately selecting the raw material compound, another benzocarbazole compound of the present invention can be synthesized by a method according to the above synthesis example.

<Example>
Electroluminescent devices according to Examples 1 to 5 and Comparative Examples 1 to 3 were prepared, and voltage (V), current density (mA / cm ² ), and luminous efficiency (Lm), which are characteristics at the time of 100 cd / m ² emission, respectively. / W), current efficiency (cd / A), emission wavelength (nm), and chromaticity (x, y) were measured. In addition, measurement of external quantum efficiency (%) and lifetime characteristics (luminance retention rate (%)) were performed. Hereinafter, Examples 1 to 5 and Comparative Examples 1 to 3 will be described in detail.

Table 1 below shows the material configuration of each layer in the electroluminescent elements according to Examples 1 to 5 and Comparative Examples 1 to 3 manufactured.

  In Table 1, “2-TNATA” is 4,4′4 ”-tris (2-naphthyl (phenyl) amino) triphenylamine,“ CuPc ”is copper phthalocyanine,“ NPD ”is N, N′-di (1 -Naphthyl) -N, N'-diphenylbenzidine, "CBP" is 4,4'-di-9-carbazolylbiphenyl, "Balq" is bis (2-methyl-8-quinolinolate) (4-phenylphenolate) ) Aluminum, “ALQ” is tris (8-quinolinolato) aluminum, “ET1” is 2,5-bis (2,2′-bipyridyl-6-yl) -1,1-dimethyl-3,4-dimesityl Siloles, each having the following chemical structural formula:

A glass substrate of 26 mm × 28 mm × 0.7 mm on which ITO was deposited to a thickness of 150 nm was used as a transparent support substrate. This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus, a molybdenum vapor deposition boat containing 2-TNATA, a molybdenum vapor deposition boat containing NPD, and a molybdenum product containing compound (1-13). Vapor deposition boat, molybdenum vapor deposition boat with Ir (piq) ₃ , molybdenum vapor deposition boat with Balq, molybdenum vapor deposition boat with ALQ, molybdenum vapor deposition boat with lithium fluoride, and A tungsten evaporation boat containing aluminum was installed.

Depressurize the vacuum chamber to 1 × 10 ⁻³ Pa, heat the vapor deposition boat containing 2-TNATA, deposit 2-TNATA to a film thickness of 40 nm, and form a hole injection layer; Then, the evaporation boat containing NPD was heated, and NPD was evaporated to a film thickness of 10 nm to form a hole transport layer. Next, the molybdenum vapor deposition boat containing the compound (1-13) and the molybdenum vapor deposition boat containing Ir (piq) ₃ were heated to co-deposit both compounds to a film thickness of 35 nm. A light emitting layer was formed. At this time, the doping concentration of Ir (piq) ₃ was about 7% by weight. Next, the evaporation boat containing Balq was heated, and Balq was evaporated to a film thickness of 10 nm to form a hole blocking layer. Next, the evaporation boat containing ALQ was heated, and ALQ was evaporated to a film thickness of 30 nm to form an electron transport layer. The above deposition rate was 0.1-1 nm / sec.

  Thereafter, the vapor deposition boat containing lithium fluoride is heated to deposit lithium fluoride at a deposition rate of 0.005 to 0.01 nm / second so that the film thickness becomes 0.5 nm, and then vapor deposition containing aluminum. An organic EL element was obtained by heating the boat and depositing aluminum at a deposition rate of 0.2 to 1 nm / second so as to have a film thickness of 100 nm.

Using the ITO electrode as the anode and the lithium fluoride / aluminum electrode as the cathode, the characteristics at 100 cd / m ² emission were measured. The voltage was 5 V, the current density was 1.25 mA / cm ² , the emission efficiency was 5.0 Lm / W, and the current efficiency was 8 cd. / A, emission wavelength 628 nm, and chromaticity (0.679, 0.320). The external quantum efficiency was 11%, and the current density at that time was 1 mA / cm ² . Further, when a constant current driving test was performed with a current density for obtaining an initial luminance of 1000 cd / m ² , the luminance retention rate after 1000 hours was 84%.

An organic EL device was obtained by the method according to Example 1 except that Ir (piq) ₃ used as the phosphorescent dopant in Example 1 was changed to PtOEP. Using the ITO electrode as the anode and the lithium fluoride / aluminum electrode as the cathode, the characteristics at 100 cd / m ² emission were measured. The voltage was 6.3 V, the current density was 6.5 mA / cm ² , the emission efficiency was 0.8 Lm / W, the current The efficiency was 1.5 cd / A, the emission wavelength was 649 nm, and the chromaticity (0.713, 0.284). The external quantum efficiency was 5.8%, and the current density at that time was ^2.5 mA / cm ² . When constant current driving at 0.25 mA / cm ² was performed, the initial luminance was 240 cd / m ² and the luminance retention rate after 200 hours was 91%.

A glass substrate (manufactured by Tokyo Sanyo Vacuum Co., Ltd.) of 26 mm × 28 mm × 0.7 mm on which ITO was deposited to a thickness of 150 nm was used as a transparent support substrate. This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Vacuum Kiko Co., Ltd.), molybdenum vapor deposition boat containing 2-TNATA, molybdenum vapor deposition boat containing NPD, compound (1 -13) molybdenum vapor deposition boat, Ir (piq) ₃ molybdenum vapor deposition boat, ET1 molybdenum vapor deposition boat, molybdenum fluoride vapor deposition boat containing lithium fluoride, and aluminum A tungsten vapor deposition boat containing the

Depressurize the vacuum chamber to 1 × 10 ⁻³ Pa, heat the vapor deposition boat containing 2-TNATA, deposit 2-TNATA to a film thickness of 40 nm, and form a hole injection layer; Then, the evaporation boat containing NPD was heated, and NPD was evaporated to a film thickness of 10 nm to form a hole transport layer. Next, the molybdenum vapor deposition boat containing the compound (1-13) and the molybdenum vapor deposition boat containing Ir (piq) ₃ were heated to co-deposit both compounds to a film thickness of 45 nm. A light emitting layer was formed. At this time, the doping concentration of Ir (piq) ₃ was about 7% by weight. Next, the evaporation boat containing ET1 was heated to deposit ET1 to a film thickness of 30 nm to form an electron transport layer. The above deposition rate was 0.1-1 nm / sec.

  Thereafter, the vapor deposition boat containing lithium fluoride is heated to deposit lithium fluoride at a deposition rate of 0.005 to 0.01 nm / second so that the film thickness becomes 0.5 nm, and then vapor deposition containing aluminum. An organic EL element was obtained by heating the boat and depositing aluminum at a deposition rate of 0.2 to 1 nm / second so as to have a film thickness of 100 nm.

Using the ITO electrode as the anode and the lithium fluoride / aluminum electrode as the cathode, the characteristics at 100 cd / m ² emission were measured. The voltage was 3.9 V, the current density was 1.18 mA / cm ² , the emission efficiency was 6.8 Lm / W, the current The efficiency was 8.5 cd / A, the emission wavelength was 628 nm, and the chromaticity (0.680, 0.319). The external quantum efficiency was 11.3%, and the current density at that time was 1 mA / cm ² . In addition, when a constant current driving test was performed at a current density for obtaining an initial luminance of 1000 cd / m ² , the luminance retention rate after a lapse of 1000 hours was 91%.

An organic EL device was obtained by a method according to Example 3 except that Ir (piq) ₃ used as the phosphorescent dopant in Example 3 was replaced with Ir (btpy) ₂ acac. Using the ITO electrode as the anode and the lithium fluoride / aluminum electrode as the cathode, the characteristics at 100 cd / m ² emission were measured. The voltage was 4.5 V, the current density was 2.1 mA / cm ² , the emission efficiency was 3.3 Lm / W, the current was The efficiency was 4.8 cd / A, the emission wavelength was 621 nm, and the chromaticity (0.683, 0.315). The external quantum efficiency was 6.1%, and the current density at that time was ² mA / cm ² . In addition, when a constant current driving test was performed at a current density for obtaining an initial luminance of 1000 cd / m ² , the luminance retention rate after 100 hours was 81%.

  A glass substrate of 26 mm × 28 mm × 0.7 mm on which ITO was deposited to a thickness of 150 nm was used as a transparent support substrate. This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus, a molybdenum vapor deposition boat containing copper phthalocyanine, a molybdenum vapor deposition boat containing NPD, and a molybdenum vapor deposition containing compound (1-13). A molybdenum vapor deposition boat containing D1, a molybdenum vapor deposition boat containing ET1, a molybdenum vapor deposition boat containing lithium fluoride, and a tungsten vapor deposition boat containing aluminum were mounted.

Depressurize the vacuum chamber to 1 × 10 ⁻³ Pa, heat the evaporation boat containing copper phthalocyanine, deposit copper phthalocyanine to a film thickness of 20 nm, and form a hole injection layer. The inside evaporation boat was heated and NPD was evaporated to a film thickness of 30 nm to form a hole transport layer. Next, the molybdenum vapor deposition boat containing the compound (1-13) and the molybdenum vapor deposition boat containing D1 are heated to co-evaporate both compounds to a thickness of 30 nm to form a light emitting layer. did. At this time, the doping concentration of D1 was about 5% by weight. Next, the evaporation boat containing ET1 was heated, and ET1 was evaporated to a film thickness of 20 nm to form an electron transport layer. The above deposition rate was 0.1-1 nm / sec.

  Thereafter, the vapor deposition boat containing lithium fluoride is heated to deposit lithium fluoride at a deposition rate of 0.005 to 0.01 nm / second so that the film thickness becomes 0.5 nm, and then vapor deposition containing aluminum. An organic EL element was obtained by heating the boat and depositing aluminum at a deposition rate of 0.2 to 1 nm / second so as to have a film thickness of 100 nm.

Using the ITO electrode as the anode and the lithium fluoride / aluminum electrode as the cathode, the characteristics at 100 cd / m ² emission were measured. The voltage was 3.7 V, the current density was 1.7 mA / cm ² , the emission efficiency was 4.8 Lm / W, the current The efficiency was 5.9 cd / A, the emission wavelength was 473 nm, and the chromaticity (0.144, 0.284). The external quantum efficiency was 3.5%, and the current density at that time was 1.6 mA / cm ² . In addition, when a constant current driving test was performed at a current density for obtaining an initial luminance of 1000 cd / m ² , the luminance retention rate after the elapse of 100 hours was 55%.

<Comparative Example 1>
An organic EL device was obtained by the method according to Example 1 except that the compound (1-13) used in Example 1 was replaced with CBP. Using the ITO electrode as the anode and the lithium fluoride / aluminum electrode as the cathode, the characteristics at 100 cd / m ² emission were measured. The voltage was 6.4 V, the current density was 1.3 mA / cm ² , the emission efficiency was 3.8 Lm / W, the current The efficiency was 7.7 cd / A, the emission wavelength was 626 nm, and the chromaticity (0.674, 0.323). The external quantum efficiency was 8.3%, and the current density at that time was 1 mA / cm ² . In addition, when a constant current driving test was performed at a current density for obtaining an initial luminance of 1000 cd / m ² , the luminance retention rate after 1000 hours was 55%.

<Comparative example 2>
An organic EL device was obtained by the method according to Example 2 except that the compound (1-13) used in Example 2 was replaced with CBP. Using the ITO electrode as the anode and the lithium fluoride / aluminum electrode as the cathode, the characteristics at 100 cd / m ² emission were measured. The voltage was 7.7 V, the current density was 7.4 mA / cm ² , the emission efficiency was 0.5 Lm / W, the current The efficiency was 1.3 cd / A, the emission wavelength was 648 nm, and the chromaticity (0.673, 0.307). The external quantum efficiency was 3.1%, and the current density at that time was 6.2 mA / cm ² . When constant current driving at 0.25 mA / cm ² was performed, the initial luminance was 230 cd / m ² and the luminance retention ratio after 200 hours was 78%.

<Comparative Example 3>
An organic EL device was obtained by the method according to Example 4 except that the compound (1-13) used in Example 4 was changed to Balq. Using the ITO electrode as the anode and the lithium fluoride / aluminum electrode as the cathode, the characteristics at 100 cd / m ² emission were measured. The voltage was 5.9 V, the current density was 2.1 mA / cm ² , the emission efficiency was 2.5 Lm / W, the current was The efficiency was 4.8 cd / A, the emission wavelength was 619 nm, and the chromaticity (0.680, 0.317). The external quantum efficiency was 6.1%, and the current density at that time was ² mA / cm ² . Further, when a constant current driving test was performed with a current density for obtaining an initial luminance of 1000 cd / m ² , the luminance retention rate after 100 hours was 53%.

Table 2 below summarizes the performance evaluation of the electroluminescent elements according to Examples 1 to 5 and Comparative Examples 1 to 3 described above.

  According to a preferred embodiment of the present invention, since the range of solvent selection during synthesis is large, it is possible to increase the degree of freedom of compound synthesis and to employ a free layer forming means when forming a layer of a light emitting element. it can. In addition, the present invention provides an organic electroluminescence device having higher performance in at least one of heat resistance, light emission efficiency, current efficiency, device lifetime, and external quantum efficiency, a display device including the same, and a lighting device including the same. be able to.

It is a schematic sectional drawing which shows the organic electroluminescent element which concerns on this embodiment.

Explanation of symbols

DESCRIPTION OF SYMBOLS 100 Organic electroluminescent element 101 Substrate 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light emitting layer 106 Hole blocking layer 107 Electron transport layer 108 Electron injection layer 109 Cathode

Claims (33)

A benzocarbazole compound represented by the following general formula (1).
(Where
Ar is phenyl, biphenylyl, naphthyl or phenanthryl;
A ¹ and A ² are each independently phenyl, biphenylyl, terphenylyl, naphthyl or phenanthryl;
R ^{1 to} R ⁸ are hydrogen. ) A benzocarbazole compound represented by the following general formula (1).
(Where
Ar is phenyl, biphenylyl, naphthyl or phenanthryl;
A ¹ and A ² are both phenyl, biphenylyl, terphenylyl, naphthyl or phenanthryl,
R ^{1 to} R ⁸ are hydrogen. ) Ar is phenyl, 4-biphenylyl, 1-naphthyl, 2-naphthyl or 9-phenanthryl;
A ¹ And A ² Each independently is phenyl, 4-biphenylyl, 1-naphthyl, 2-naphthyl or 9-phenanthryl;
R ¹ ~ R ⁸ Is hydrogen,
The benzocarbazole compound according to claim 1. Ar is phenyl, 4-biphenylyl, 1-naphthyl, 2-naphthyl or 9-phenanthryl;
A ¹ And A ² Are both phenyl, 4-biphenylyl, 1-naphthyl, 2-naphthyl or 9-phenanthryl;
R ¹ ~ R ⁸ Is hydrogen,
The benzocarbazole compound according to claim 2. Ar is phenyl;
A ¹ is phenyl, A ² is phenyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound according to claim 4 . Ar is phenyl;
A ¹ is 4-biphenylyl, A ² is 4-biphenylyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound according to claim 4 . Ar is phenyl;
A ¹ is 2-naphthyl, A ² is 2-naphthyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound according to claim 4 . Ar is phenyl;
A ¹ Is 1-naphthyl and A ² Is 1-naphthyl,
R ¹ ~ R ⁸ Is hydrogen,
The benzocarbazole compound according to claim 4. Ar is 2-naphthyl,
A ¹ is phenyl, A ² is phenyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound according to claim 4 . Ar is 2-naphthyl,
A ¹ is 4-biphenylyl, A ² is 4-biphenylyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound according to claim 4 . Ar is 2-naphthyl,
A ¹ is 2-naphthyl, A ² is 2-naphthyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound according to claim 4 . Ar is 2-naphthyl,
A ¹ Is 1-naphthyl and A ² Is 1-naphthyl,
R ¹ ~ R ⁸ Is hydrogen,
The benzocarbazole compound according to claim 4. Ar is phenyl;
A ¹ is phenyl, A ² is 4-biphenylyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound according to claim 3 . Ar is phenyl;
A ¹ is 4-biphenylyl, A ² is phenyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound according to claim 3 . Ar is phenyl;
A ¹ is phenyl, A ² is 2-naphthyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound according to claim 3 . Ar is phenyl;
A ¹ is 2-naphthyl, A ² is phenyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound according to claim 3 . Ar is phenyl;
A ¹ Is phenyl and A ² Is 1-naphthyl,
R ¹ ~ R ⁸ Is hydrogen,
The benzocarbazole compound according to claim 3. Ar is phenyl;
A ¹ Is 1-naphthyl and A ² Is phenyl,
R ¹ ~ R ⁸ Is hydrogen,
The benzocarbazole compound according to claim 3. Ar is phenyl;
A ¹ is 4-biphenylyl, A ² is 2-naphthyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound according to claim 3 . Ar is phenyl;
A ¹ is 2-naphthyl, A ² is 4-biphenylyl,
R ^{1 to} R ⁸ are hydrogen,
The benzocarbazole compound according to claim 3 . Ar is phenyl;
A ¹ Is 4-biphenylyl and A ² Is 1-naphthyl,
R ¹ ~ R ⁸ Is hydrogen,
The benzocarbazole compound according to claim 3. Ar is phenyl;
A ¹ Is 1-naphthyl and A ² Is 4-biphenylyl;
R ¹ ~ R ⁸ Is hydrogen,
The benzocarbazole compound according to claim 3. Ar is phenyl;
A ¹ Is 2-naphthyl and A ² Is 1-naphthyl,
R ¹ ~ R ⁸ Is hydrogen,
The benzocarbazole compound according to claim 3. Ar is phenyl;
A ¹ Is 1-naphthyl and A ² Is 2-naphthyl,
R ¹ ~ R ⁸ Is hydrogen,
The benzocarbazole compound according to claim 3. A material for a light emitting layer of a light emitting device, comprising the benzocarbazole compound according to any one of claims 1 to 24 . The luminescence according to claim 25 , further comprising at least one selected from the group consisting of perylene derivatives, borane derivatives, amine-containing styryl derivatives, aromatic amine derivatives, coumarin derivatives, pyran derivatives, iridium complexes and platinum complexes. Layer material. 27. An organic electroluminescence device comprising: a pair of electrodes composed of an anode and a cathode; and a light emitting layer disposed between the pair of electrodes and containing the light emitting layer material according to claim 25 or 26 . And an electron transport layer and / or an electron injection layer disposed between the cathode and the light emitting layer, wherein at least one of the electron transport layer and the electron injection layer includes a quinolinol-based metal complex, a pyridine derivative, and 28. The organic electroluminescent device according to claim 27 , comprising at least one selected from the group consisting of phenanthroline derivatives. Furthermore, it has an electron transport layer and / or an electron injection layer disposed between the cathode and the light emitting layer, and at least one of the electron transport layer and the electron injection layer contains a quinolinol-based metal complex. The organic electroluminescent element according to claim 27 . Furthermore, it has an electron carrying layer and / or an electron injection layer arrange | positioned between the said cathode and this light emitting layer, At least 1 of this electron carrying layer and an electron injection layer contains a pyridine derivative. 27. The organic electroluminescent device as described in 27 . Furthermore, it has an electron carrying layer and / or an electron injection layer arrange | positioned between the said cathode and this light emitting layer, At least 1 of this electron carrying layer and an electron injection layer contains a phenanthroline derivative. 27. The organic electroluminescent device as described in 27 . Display device comprising the organic electroluminescent device as claimed in any one of claims 27 to 31. Lighting device comprising the organic electroluminescent device as claimed in any one of claims 27 to 31.