JP3189805B2 - Organic electroluminescence device - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescence device having excellent light emission characteristics.

[0002]

2. Description of the Related Art Organic electroluminescence (EL)
The element is a self-luminous element utilizing the principle that a fluorescent substance emits light by the recombination energy of holes injected from an anode and electrons injected from a cathode when an electric field is applied. Eastman Kodak C.I. W. Tang et al. Report on a low-voltage driven organic EL device using a stacked device (CW Tang, SA VanSlyke, Applied Physics Letters (Applied Physics Letters)).
sics Letters), 51, 913, 19
Since 1987, researches on organic EL elements using organic materials as constituent materials have been actively conducted.
Tang et al. Use tris (8-hydroxyquinolinol aluminum) for the light emitting layer and a triphenyldiamine derivative for the hole transport layer. The advantages of the laminated structure include:
Increasing the efficiency of hole injection into the light-emitting layer, increasing the efficiency of excitons generated by recombination by blocking electrons injected from the cathode, confining excitons generated in the light-emitting layer, etc. No. As in this example, the element structure of the organic EL element is a two-layer type of a hole transporting (injection) layer, an electron transporting light emitting layer, or a hole transporting (injection) layer,
A three-layer type including a light-emitting layer and an electron transport (injection) layer is well known. In such a laminated structure element, in order to increase the recombination efficiency of injected holes and electrons, the element structure and the forming method are devised.

As a hole transporting material, N, N'-diphenyl-N, N'-bis (3-methylphenyl)-[1,
Aromatic diamine derivatives such as [1'-biphenyl] -4,4'-diamine are well known (for example, see Japanese Patent Application Laid-Open No.
-20771, JP-A-8-40995, JP-A-8-40997, JP-A-8-53397, JP-A-8-87122 and the like.

[0004] Oxadiazole derivatives, triazole derivatives and the like are well known as electron transporting materials.

As light emitting materials, chelate complexes such as tris (8-quinolinolato) aluminum complex, and luminescent materials such as coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives, and oxadiazole derivatives are known. Is also reported to emit light in the visible region from blue to red, and the realization of a color display element is expected (for example,
JP-A-8-239655, JP-A-7-13856
No. 1, JP-A-3-200889, etc.).

[0006]

However, the organic EL device using the blue light emitting material disclosed so far is
There is a problem that a long lifetime, excellent color purity, and high efficiency of blue light emission cannot be obtained. As one of the causes, for example, when an electron transporting layer and a hole transporting layer are used in addition to the light emitting layer, a change in EL emission color due to interaction between light emission from the light emitting layer and a constituent material other than the light emitting material, And a reduction in efficiency.

[0007]

Means for Solving the Problems As a result of intensive studies, the present inventors have found that, in a specific bis (styryldiphenylamino) naphthalene derivative, the 2-position or 1,4-bisdiarylamino group is attached to the 1,5-bisdiarylamino group. A compound having a substituent other than two or three hydrogen atoms at the 2-position relative to the bis-diarylamino group and at 1,3-, 5-, or 7-position relative to the 2,6-bisdiarylamino group; It was found that the organic EL device used as the above did not cause any interaction with the constituent materials of the organic EL device other than the compound of the present invention, and showed blue light emission with good color purity, leading to the present invention.

That is, the present invention provides an organic electroluminescent device having at least a light emitting layer between an anode and a cathode, wherein the light emitting layer contains a material represented by the following general formula [1] alone or as a mixture. It is an organic electroluminescence element.

[0009]

Embedded image

(However, Ar _{1 to} Ar ₄ are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, at least one of which is a styryl group represented by the following general formula [2]. Ar ₁ and Ar ₂ and Ar ₃ and Ar ₄ may form a ring with each other, and R _{1 to} R ₆ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group. Group, cyano group, nitro group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon Group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted Alkoxycarbonyl group, a carboxyl group, less of R _1, R ₄
One is a group other than a hydrogen atom, and both are hydrogen
It cannot be a group other than an atom. )

[0011]

Embedded image

(However, R _{7 to} R ₁₇ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group (excluding diphenylamino group), a cyano group, a nitro group, a substituted or Unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocycle A ring group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, or a carboxyl group.) In the present invention, at least a light emitting layer is provided between the anode and the cathode. In the organic electroluminescence device having the above, the light emitting layer is a material represented by the following general formula [3] Is used alone or as a mixture.

[0013]

Embedded image

(However, Ar _{5 to} Ar ₈ are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, at least one of which is represented by the following general formula [2]
Is a styryl group represented by Ar ₅ and Ar ₆ and Ar
₇ and Ar ₈ may form a ring with each other. R _{18 to} R ₂₃ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group,
Cyano group, nitro group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, A substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group,
Represents a carboxyl group, and at least one of R ₁₈ and R ₁₉
One is a group other than a hydrogen atom, and both are hydrogen atoms
There is no other group. )

[0015]

Embedded image

(However, R _{7 to} R ₁₇ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group (excluding diphenylamino group), a cyano group, a nitro group, a substituted or Unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocycle A ring group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, or a carboxyl group.) The present invention has at least a light emitting layer between the anode and the cathode. In the organic electroluminescence device, the light emitting layer is made of a material represented by the following general formula [4]. An organic electroluminescent element, which is contained alone or as a mixture.

[0017]

Embedded image

(However, Ar _{9 to} Ar ₁₂ are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, at least one of which is a styryl group represented by the following general formula [2]. Ar ₉ and Ar ₁₀ and Ar ₁₁ and Ar ₁₂ may form a ring with each other.
_{24 to} R ₂₉ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a cyano group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted group; Substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aryl An oxy group,
Represents a substituted or unsubstituted alkoxycarbonyl group or a carboxyl group, and at least one of R ₂₄ , R ₂₆ , R ₂₇ , and R ₂₉ is a group other than a hydrogen atom, and not all of them are groups other than a hydrogen atom. )

[0019]

Embedded image

(Where R _{7 to} R ₁₇ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group (excluding diphenylamino group), a cyano group, a nitro group, Unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocycle A ring group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, or a carboxyl group.) The compounds of the present invention are represented by the general formulas [1] and [3]. , [4]. At least one is a styryl group represented by the general formula [2], and Ar ₁ and Ar ₂ , Ar ₃ and Ar ₄ , Ar ₅ and Ar ₆ , Ar ₇ and A
r ₈ , Ar ₉ and Ar ₁₀ , and Ar ₁₁ and Ar ₁₂ may each form a ring with each other. In the above general formula, Ar ₁ to
The compound represented by Ar ₁₂ is a substituted or unsubstituted aryl group having 5 to 30 carbon atoms. Examples of such compounds include aromatic hydrocarbons such as benzene, naphthalene, anthracene, phenanthrene, naphthacene, pyrene, biphenyl and terphenyl, or condensed polycyclic hydrocarbons,
Carbazole, pyrrole, thiophene, furan, imidazole, pyrazole, isothiazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, furazane, tianthrene, isobenzofuran, phenoxazine, indolizine, indole, isoindole, 1
H-indazole, purine, quinoline, isoquinoline,
Phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, carbazole, β-carbazoline, phenanthridine, acridine, perimidine, phenanthroline, phenazine, phenothiazine,
A monovalent group obtained by removing one hydrogen atom from a heterocyclic compound such as phenoxazine or a condensed heterocyclic compound and a derivative thereof are exemplified. Examples of the compound forming a ring include:
And a carbazolyl group. R _{1 to} R ₂₉ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a cyano group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, Or an unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted Aralkyl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkoxycarbonyl group, and carboxyl group. Examples of the substituted or unsubstituted arylene group include a phenylene group, a naphthylene group, an anthrylene group, a phenanthrylene group, a naphthacenylene group, and a pyrenylene group. Examples of the halogen atom include fluorine, chlorine, bromine, and iodine. A substituted or unsubstituted amino group is represented by -NX ₁ X ₂ ;
X ₁ and X ₂ each independently represent a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, n
-Pentyl group, n-hexyl group, n-heptyl group, n-
Octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-
Butyl, 1,2,3-trihydroxypropyl, chloromethyl, 1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl, 1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 3-dibromoisopropyl group, 2,3-
Dibromo t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl Group, 2, 3
T-butyl iodide, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl, 2-aminoethyl, 2-aminoisobutyl, 1,2-diaminoethyl, 1, 3-diaminoisopropyl group, 2,
3-diamino t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-
Cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group,
2,3-dicyano t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group,
2-nitroethyl group, 2-nitroisobutyl group, 1,2
-Dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro t-butyl group, 1,2,3-trinitropropyl group, phenyl group, 1-naphthyl group, 2-
Naphthyl group, 1-anthryl group, 2-anthryl group, 9
-Anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-
Naphthacenyl group, 9-naphthacenyl group, 4-styrylphenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-ter Phenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-
Terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, p
-T-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group,
4′-methylbiphenylyl group, 4 ″ -t-butyl-
p-terphenyl-4-yl group, 2-pyrrolyl group, 3-
Pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 2-indolyl group, 3
-Indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group,
7-isoindolyl group, 2-furyl group, 3-furyl group,
2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzo Furanyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6- Quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2- Quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group,
3-carbazolyl group, 4-carbazolyl group, 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7-phenanthridinyl group, 8-
Phenanthridinyl group, 9-phenanthridinyl group, 1
0-phenanthridinyl group, 1-acridinyl group, 2-
Acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1,7-phenanthrolin-2-yl group, 1,7-phenanthrolin-3-yl group, 1,7-phenanth Lorin-4-yl group, 1,7-
Phenanthrolin-5-yl group, 1,7-phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group, 1,7-phenanthroline-9-yl group, 1, 7
-Phenanthroline-10-yl group, 1,8-phenanthrolin-2-yl group, 1,8-phenanthroline-3
-Yl group, 1,8-phenanthrolin-4-yl group,
1,8-phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group, 1,8-phenanthrolin-9-yl group Group, 1,8-phenanthrolin-10-yl group, 1,9
-Phenanthroline-2-yl group, 1,9-phenanthroline-3-yl group, 1,9-phenanthroline-4-
An yl group, a 1,9-phenanthrolin-5-yl group,
9-phenanthrolin-6-yl group, 1,9-phenanthrolin-7-yl group, 1,9-phenanthroline-8
-Yl group, 1,9-phenanthrolin-10-yl group,
1,10-phenanthrolin-2-yl group, 1,10-
Phenanthrolin-3-yl group, 1,10-phenanthrolin-4-yl group, 1,10-phenanthroline-5
-Yl group, 2,9-phenanthrolin-1-yl group,
2,9-phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group, 2,9-phenanthrolin-6-yl group Group, 2,9-phenanthrolin-7-yl group, 2,9-
Phenanthroline-8-yl group, 2,9-phenanthroline-10-yl group, 2,8-phenanthroline-1-
Yl group, 2,8-phenanthrolin-3-yl group, 2,
8-phenanthrolin-4-yl group, 2,8-phenanthrolin-5-yl group, 2,8-phenanthroline-6
An -yl group, a 2,8-phenanthroline-7-yl group,
2,8-phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group, 2,7-phenanthrolin-1-yl group, 2,7-phenanthrolin-3-yl Group, 2,7-phenanthrolin-4-yl group, 2,7-
Phenanthrolin-5-yl group, 2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group, 2,7-phenanthrolin-9-yl group, 2, 7
-Phenanthroline-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2
-Phenothiazinyl group, 3-phenothiazinyl group, 4-
Phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxazolyl group,
5-oxadiazolyl group, 3-furazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group, 2-methylpyrrol-5-yl group, 3-methylpyrrol-1-yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group,
3-methylpyrrol-5-yl group, 2-t-butylpyrrol-4-yl group, 3- (2-phenylpropyl) pyrrol-1-yl group, 2-methyl-1-indolyl group, 4
-Methyl-1-indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl 1-indolyl group, 4-t-butyl 1-indolyl group, 2-t- Butyl 3-indolyl group, 4-t-butyl 3-indolyl group and the like. However, neither X ₁ nor X ₂ is an aryl group. Examples of the substituted or unsubstituted alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, and n
-Hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-
Dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,
2,3-trihydroxypropyl group, chloromethyl group,
1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trichloro Propyl, bromomethyl, 1-bromoethyl, 2-bromoethyl, 2-bromoisobutyl, 1,2-dibromoethyl, 1,3
-Dibromoisopropyl group, 2,3-dibromo t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-
Iodoisobutyl group, 1,2-diiodoethyl group, 1,
3-diiodoisopropyl group, 2,3-diiodo t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2
-Aminoisobutyl group, 1,2-diaminoethyl group,
1,3-diaminoisopropyl group, 2,3-diamino t
-Butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano t-butyl group, 1,2,3-tricyanopropyl group,
Nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro t-butyl group, 1,2,3 -Trinitropropyl group, and the like. Examples of the substituted or unsubstituted alkenyl group include a vinyl group, an allyl group, a 1-butenyl group,
-Butenyl group, 3-butenyl group, 1,3-butanedienyl group, 1-methylvinyl group, styryl group, 4-diphenylaminostyryl group, 4-di-p-tolylaminostyryl group, 4-di-m-tolyl Aminostyryl group, 2,2-
Diphenylvinyl group, 1,2-diphenylvinyl group, 1
-Methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, 1-phenylallyl group, 2-phenylallyl group, 3-phenylallyl group, 3,3-diphenylallyl group, 1,2-dimethylallyl group , 1-phenyl-1
-Butenyl group, 3-phenyl-1-butenyl group and the like.

Examples of the substituted or unsubstituted cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and a 4-methylcyclohexyl group. The substituted or unsubstituted alkoxy group is a group represented by -OY, wherein Y is an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-
Butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxymethyl, 1-hydroxyethyl, 2
-Hydroxyethyl group, 2-hydroxyisobutyl group,
1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl Group, 2
-Chloroisobutyl group, 1,2-dichloroethyl group,
1,3-dichloroisopropyl group, 2,3-dichloro-
t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo t-butyl group, 1,2,3-tribromopropyl group,
Iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo t-butyl group, 1,2,3 -Triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-
Diamino t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl Group, 2, 3
-Dicyano t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitro Isopropyl group, 2,
Examples include a 3-dinitro t-butyl group and a 1,2,3-trinitropropyl group. Examples of the substituted or unsubstituted aromatic hydrocarbon group include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 1-phenanthryl group,
Phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2- Biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m
-Terphenyl-4-yl group, m-terphenyl-3-
Yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, pt-butylphenyl, p- (2-phenylpropyl) phenyl, 3-
Methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylyl group, 4 ″ -t-butyl-p-terphenyl-4-yl group And the like. Examples of the substituted or unsubstituted aromatic heterocyclic group include a 1-pyrrolyl group, a 2-pyrrolyl group, a 3-pyrrolyl group, a pyrazinyl group, a 2-pyridinyl group, a 3-pyridinyl group, a 4-pyridinyl group, a 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7
-Indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7
-Isoindolyl group, 2-furyl group, 3-furyl group, 2
-Benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuran Nyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl Group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl Group, 5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group,
3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phen Nanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-
Acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1,
7-phenanthrolin-2-yl group, 1,7-phenanthrolin-3-yl group, 1,7-phenanthroline-4
-Yl group, 1,7-phenanthrolin-5-yl group,
1,7-phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group, 1,7-phenanthrolin-9-yl group, 1,7-phenanthrolin-10-yl group Group, 1,8-phenanthrolin-2-yl group, 1,8-
Phenanthrolin-3-yl group, 1,8-phenanthrolin-4-yl group, 1,8-phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group, 1, 8
Phenanthroline-7-yl group, 1,8-phenanthroline-9-yl group, 1,8-phenanthroline-10
-Yl group, 1,9-phenanthrolin-2-yl group,
1,9-phenanthrolin-3-yl group, 1,9-phenanthrolin-4-yl group, 1,9-phenanthrolin-5-yl group, 1,9-phenanthrolin-6-yl group Group, 1,9-phenanthrolin-7-yl group, 1,9-
Phenanthroline-8-yl group, 1,9-phenanthroline-10-yl group, 1,10-phenanthroline-2
-Yl group, 1,10-phenanthrolin-3-yl group,
1,10-phenanthrolin-4-yl group, 1,10-
Phenanthrolin-5-yl group, 2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group, 2, 9
-Phenanthroline-5-yl group, 2,9-phenanthrolin-6-yl group, 2,9-phenanthroline-7-
Yl group, 2,9-phenanthroline-8-yl group, 2,
9-phenanthrolin-10-yl group, 2,8-phenanthrolin-1-yl group, 2,8-phenanthroline-
3-yl group, 2,8-phenanthrolin-4-yl group,
2,8-phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group, 2,8-phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl group Group, 2,8-phenanthrolin-10-yl group, 2,7
-Phenanthroline-1-yl group, 2,7-phenanthrolin-3-yl group, 2,7-phenanthroline-4-
Yl group, 2,7-phenanthrolin-5-yl group, 2,
7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group, 2,7-phenanthroline-9
An -yl group, a 2,7-phenanthroline-10-yl group,
1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 10-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 10-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-flazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group, 2-methylpyrrol-5-yl group, 3-methylpyrrole- 1-yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, - methylpyrrole-5-yl group,
2-t-butylpyrrol-4-yl group, 3- (2-phenylpropyl) pyrrol-1-yl group, 2-methyl-1
-Indolyl group, 4-methyl-1-indolyl group, 2-
Methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl 1-indolyl group, 4-t-butyl 1-indolyl group, 2-t-butyl 3-indolyl group, 4-t- Butyl 3-indolyl group, and the like. Examples of the substituted or unsubstituted aralkyl group include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butyl group, an α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β
-Naphthylethyl group, 2-β-naphthylethyl group, 1-
β-naphthylisopropyl group, 2-β-naphthylisopropyl group, 1-pyrrolylmethyl group, 2- (1-pyrrolyl) ethyl group, p-methylbenzyl group, m-methylbenzyl group, o-methylbenzyl group, p-chloro Benzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p
-Bromobenzyl group, m-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxy Benzyl group, p-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-nitrobenzyl group, m
-Nitrobenzyl group, o-nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group, 1-chloro-2-phenylisopropyl group and the like. No. A substituted or unsubstituted aryloxy group is represented by-
OZ, wherein Z is phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-
Phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2- Biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m
-Terphenyl-4-yl group, m-terphenyl-3-
Yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, pt-butylphenyl, p- (2-phenylpropyl) phenyl, 3-
Methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylyl group, 4 ″ -t-butyl-p-terphenyl-4-yl group , 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 3-pyridinyl, 4-
Pyridinyl group, 2-indolyl group, 3-indolyl group,
4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5
-Benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzo Furanyl group, 7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl Group, 3-isoquinolyl group, 4-isoquinolyl group, 5-
Isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group, 5
-Quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 1-phenanthridinyl group,
2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9- Phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1,7-phenanthroline-2-yl Group, 1,7-phenanthrolin-3-yl group, 1,7-
Phenanthrolin-4-yl group, 1,7-phenanthrolin-5-yl group, 1,7-phenanthrolin-6-yl group, 1,7-phenanthroline-8-yl group, 1, 7
-Phenanthroline-9-yl group, 1,7-phenanthrolin-10-yl group, 1,8-phenanthroline-2
-Yl group, 1,8-phenanthrolin-3-yl group,
1,8-phenanthrolin-4-yl group, 1,8-phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group Group, 1,8-phenanthrolin-9-yl group, 1,8-
Phenanthroline-10-yl group, 1,9-phenanthroline-2-yl group, 1,9-phenanthroline-3-
Yl group, 1,9-phenanthrolin-4-yl group, 1,
9-phenanthrolin-5-yl group, 1,9-phenanthrolin-6-yl group, 1,9-phenanthroline-7
-Yl group, 1,9-phenanthroline-8-yl group,
1,9-phenanthrolin-10-yl group, 1,10-
Phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group, 1,10-phenanthroline-4
-Yl group, 1,10-phenanthrolin-5-yl group,
2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group Group, 2,9-phenanthrolin-6-yl group, 2,9-
Phenanthroline-7-yl group, 2,9-phenanthroline-8-yl group, 2,9-phenanthroline-10-
Yl group, 2,8-phenanthrolin-1-yl group, 2,
8-phenanthrolin-3-yl group, 2,8-phenanthrolin-4-yl group, 2,8-phenanthroline-5
-Yl group, 2,8-phenanthrolin-6-yl group,
2,8-phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group, 2,7-phenanthrolin-1-yl Group, 2,7-phenanthrolin-3-yl group, 2,7-
Phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group, 2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group, 2, 7
-Phenanthroline-9-yl group, 2,7-phenanthroline-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group , 4-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl Group, 3-flazanyl group, 2-thienyl group, 3-
Thienyl group, 2-methylpyrrole-1-yl group, 2-methylpyrrole-3-yl group, 2-methylpyrrole-4-yl
Yl group, 2-methylpyrrole-5-yl group, 3-methylpyrrol-1-yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrole-5-yl Yl group, 2-t-butylpyrrol-4-yl group, 3- (2-phenylpropyl) pyrrol-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1-
Indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl 1-indolyl group, 4-t-butyl 1-indolyl group, 2-t-butyl 3-indolyl group , 4-t-butyl 3-indolyl group and the like. A substituted or unsubstituted alkoxycarbonyl group is represented by -COOY, wherein Y is a methyl group,
Ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-
Pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2- Bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-
Dibromo t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl Group, 2, 3
T-butyl iodide, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl, 2-aminoethyl, 2-aminoisobutyl, 1,2-diaminoethyl, 1, 3-diaminoisopropyl group, 2,
3-diamino t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-
Cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group,
2,3-dicyano t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group,
2-nitroethyl group, 2-nitroisobutyl group, 1,2
-Dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro t-butyl group, 1,2,3-trinitropropyl group and the like.

Examples of the compounds represented by the general formulas [1], [3] and [4] of the present invention are shown below, but the present invention is not limited thereto.

[0023]

Embedded image

[0024]

Embedded image

[0025]

Embedded image

[0026]

Embedded image

[0027]

Embedded image

[0028]

Embedded image

For example, the compound represented by the above (1)
Unnecessary interaction with other components does not occur as compared to a compound in which the naphthalene ring is completely substituted with hydrogen,
Blue light emission with excellent color purity can be obtained. Such an effect was obtained only when a substituent was introduced into the naphthalene ring, and such an effect was not confirmed at other positions of the compound.

The compound represented by the general formula [1] can be synthesized by a conventionally known synthesis reaction. For example, a triphenylamine derivative is synthesized by an Ullmann reaction between diaminoarylene and halogenated benzene or an Ullmann reaction between dihalogenated arylene and an aromatic amine. The styryl derivative can be synthesized by synthesizing a corresponding aldehyde and a phosphonate, and performing a Wittig-Hornor reaction thereof.

The element structure of the organic EL element according to the present invention is a structure in which one or more organic layers are laminated between the electrodes. For example, as shown in FIGS. , An anode, a hole transport layer, a light-emitting layer, an electron transport layer, a cathode, an anode, a hole transport layer, a light-emitting layer, a cathode, or an anode, a light-emitting layer, an electron transport layer, a cathode, and the like. The compound according to the invention may be used alone or as a mixture in any of the above organic layers, and it is also possible to dope other hole transporting materials, light emitting materials and electron transporting materials.

The hole transporting material used in the present invention is not particularly limited, and any compound which is generally used as a hole transporting agent may be used. For example, the following bis (di (p-tolyl) aminophenyl) -1,1-cyclohexane [01], N, N′-diphenyl-N, N′-bis (3-methylphenyl) -1,1′-biphenyl −4
4'-diamine [02], N, N'-diphenyl-N-
N-bis (1-naphthyl) -1,1'-biphenyl)-
Triphenyldiamines such as 4,4'-diamine [03], and starburst-type molecules ([04] to [06], etc.)
And the like.

[0033]

Embedded image

[0034]

Embedded image

[0035]

Embedded image

[0036]

Embedded image

[0037]

Embedded image

[0038]

Embedded image

The electron transporting material used in the present invention is not particularly limited, and any compound which is generally used as an electron transporting material may be used. For example, 2- (4-biphenylyl) -5- (4-t-butylphenyl) -1,
3,4-oxadiazole [07], bis {2- (4-
Oxadiazole derivatives such as t-butylphenyl) -1,3,4-oxadiazole {-m-phenylene [08], and triazole derivatives ([09], [10]
Quinolinol-based metal complexes ([11] to [14])
Etc.).

[0040]

Embedded image

[0041]

Embedded image

[0042]

Embedded image

[0043]

Embedded image

[0044]

Embedded image

[0045]

Embedded image

[0046]

Embedded image

[0047]

Embedded image

The anode of the organic thin film EL element plays a role of injecting holes into the hole transport layer, and it is effective that the anode has a work function of 4.5 eV or more. Specific examples of the anode material used in the present invention include indium tin oxide alloy (ITO), tin oxide (NESA), gold, silver, platinum, and copper. As the cathode, a material having a small work function is preferable for the purpose of injecting electrons into the electron transport band or the light emitting layer. The cathode material is not particularly limited, but specifically, indium, aluminum, magnesium, a magnesium-indium alloy, a magnesium-aluminum alloy, an aluminum-lithium alloy, an aluminum-scandium-lithium alloy, a magnesium-silver alloy, or the like can be used.

The method for forming each layer of the organic EL device of the present invention is not particularly limited. A conventionally known formation method such as a vacuum evaporation method and a spin coating method can be used. The organic thin film layer containing the compound represented by the general formula (1) used in the organic EL device of the present invention may be formed by vacuum evaporation, molecular beam evaporation (MBE), dipping of a solution dissolved in a solvent, spinning, or the like. It can be formed by a known method such as a coating method, a casting method, a bar coating method, and a roll coating method.

The thickness of each organic layer of the organic EL device of the present invention is not particularly limited. In general, if the thickness is too small, defects such as pinholes are likely to occur. Is usually worse, several nm to 1
The range of μm is preferred.

[0051]

DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the present invention will be described in detail with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist.

[0052]

EXAMPLES (Synthesis Example 1) Synthesis of Compound (1) 1,3-dibromo-2-methylnaphthalene, 4-methyldiphenylamine, potassium carbonate and copper powder were placed in a three-necked flask purged with argon, and the mixture was heated at 200 ° C. for 30 minutes. Stirred for hours. After completion of the reaction, the reaction mixture was diluted with toluene and filtered by suction to remove inorganic salts. The organic phase was washed once with water, dried over magnesium sulfate, and then toluene-ligroin (volume ratio 1: 1).
2) Separation and purification by silica gel chromatography using a mixed solvent, and yellow powder of 1,5-bis (4-methyldiphenylamino) -2-methylnaphthalene was synthesized by a reprecipitation method using a mixed solvent of toluene and ethanol. .

Next, phosphorus oxychloride and N-methylformanilide were added to a toluene solution of 1,5-bis (4-methyldiphenylamino) -2-methylnaphthalene, and
Stirred at 60 ° C. for 6 hours. After the completion of the reaction, the mixture was poured into cooled water, then transferred to a separating funnel and washed with water until neutral. It was dried over magnesium sulfate, separated and purified by silica gel column chromatography using a mixed solvent of toluene and ethyl acetate (volume ratio: 5: 1) to give 1,5-bis (4-methyl-4′-formyldiphenylamino) -2.
-Methylnaphthalene was synthesized.

Then, dimethyl sulfoxide was charged into a three-necked flask purged with argon, and sodium hydride was dispersed therein. Diethyl 4-methylbenzylphosphonate was added thereto, and a solution of 1,5-bis (4-methyl-4′-formyldiphenylamino) -2-methylnaphthalene in dimethyl sulfoxide was added dropwise with stirring.
For 5 hours. After the completion of the reaction, the mixture was poured into cooled water, then transferred to a separating funnel and washed with water until neutral. After drying over magnesium sulfate, the mixture was separated and purified by silica gel chromatography using a mixed solvent of toluene and ligroin (volume ratio 1: 2), and 1,5-bis (4- ( 4-Methylbenzyl) -4′-methyldiphenylamino) -2-methylnaphthalene [compound (1)] was synthesized.

Hereinafter, the compound of the present invention is added to a light-emitting layer (1 to 6,
9 to 11, 14 to 15), examples in which a mixed thin film with a hole transport material is used as a light emitting layer (7 to 8), and a mixed thin film with an electron transport material is used as a light emitting layer (12 to 13).

Example 1 FIG. 1 shows a cross-sectional structure of an element used in Example 1. Hereinafter, a procedure for manufacturing the organic thin film EL device used in Example 1 of the present invention will be described. The device is composed of an anode / a light emitting layer / a cathode. Sheet resistance is 20Ω by sputtering ITO on glass substrate
/ □ to form an anode. Compound (1) was formed thereon as a light emitting layer by vacuum evaporation at a thickness of 40 nm. Next, a magnesium-silver alloy was formed to a thickness of 200 nm as a cathode by a vacuum evaporation method to produce an organic EL device. When a DC voltage of 5 V was applied to the device, 200 cd / m
² blue luminescence was obtained. The maximum luminous efficiency is 0.5
lm / W.

(Example 2) An organic EL device was manufactured in the same manner as in Example 1 except that the compound (3) was used as a light emitting material. When a DC voltage of 5 V was applied to this device, blue light emission of 210 cd / m ² was obtained. The maximum luminous efficiency was 0.6 lm / W.

Example 3 An ITO was formed on a glass substrate by sputtering so that the sheet resistance became 20 Ω / □, and used as an anode. A 40 nm light emitting layer was formed thereon by a spin coating method using a chloroform solution of the compound (5). Next, a magnesium-silver alloy was formed as a cathode to a thickness of 200 nm by a vacuum evaporation method to produce an organic EL device. When a DC voltage of 5 V was applied to this element,
Blue light emission of 180 cd / m ² was obtained. The maximum luminous efficiency was 0.5 lm / W.

Example 4 FIG. 2 shows a cross-sectional structure of an element used in Example 4. The device has an anode / hole transport layer / light-emitting layer /
It is composed of an electron transport layer / cathode. Sheet resistance is 20Ω by sputtering ITO on glass substrate
/ □ to form an anode. [03] was formed thereon as a hole transport layer by vacuum evaporation at a thickness of 50 nm. Next, as a light-emitting layer, the compound (2) was formed to a thickness of 40 nm by a vacuum evaporation method. Next, [09] as an electron transport layer
Was formed to a thickness of 20 nm by a vacuum evaporation method. Next, a magnesium-silver alloy was formed as a cathode to a thickness of 200 nm by a vacuum evaporation method to produce an organic EL device. When a DC voltage of 10 V was applied to this device, blue light emission of 12,000 cd / m ² was obtained. The maximum luminous efficiency is 4.5 lm / W
Met.

Example 5 An organic EL device was manufactured in the same manner as in Example 4 except that the compound (4) was used as a light emitting material. When a DC voltage of 10 V was applied to this device, blue light emission of 10,000 cd / m ² was obtained. The maximum luminous efficiency was 4.8 lm / W.

(Example 6) [01] as a hole transport layer
Example 4 except that [08] was used as the electron transport layer.
The same operation as described above was performed to produce an organic EL device. When a DC voltage of 10 V was applied to this element, 13,000 cd
/ M ² blue light emission was obtained. The maximum luminous efficiency was 4.5 lm / W.

Example 7 FIG. 4 shows a cross-sectional structure of the device used in Example 7. The device consists of anode / light-emitting layer / electron transport layer /
It is composed of a cathode. ITO was formed on a glass substrate by sputtering so that the sheet resistance became 20 Ω / □, and used as an anode. [0]
3] and compound (1) were co-evaporated at a weight ratio of 1:10 to form a thin film having a thickness of 50 nm. Next, [09] was formed as an electron transporting layer to a thickness of 50 nm by a vacuum evaporation method. Next, a 200 nm thick magnesium-silver alloy is formed as a cathode,
An L element was produced. When a DC voltage of 10 V was applied to this device, blue light emission of 5,000 cd / m ² was obtained. The maximum luminous efficiency was 2.5 lm / W.

Example 8 An organic EL device was manufactured in the same manner as in Example 7, except that the compound (5) was used instead of the compound (1). When a DC voltage of 10 V was applied to this device, blue light emission of 7,200 cd / m ² was obtained. The maximum luminous efficiency was 2.4 lm / W.

Example 9 An ITO was formed on a glass substrate by sputtering so that the sheet resistance became 20 Ω / □, and used as an anode. A compound (3) was formed thereon with a thickness of 80 nm by a vacuum deposition method as a light emitting layer, and [08] was formed thereon with a thickness of 50 nm by a vacuum deposition method as an electron transport layer. Next, a magnesium-silver alloy of 200 nm was used as a cathode.
Thus, an EL device was manufactured. DC voltage is applied to this element by 1
When 0 V was applied, blue light emission of 8,000 cd / m ² was obtained. The maximum luminous efficiency was 4.2 lm / W.

Example 10 An organic EL device was produced in the same manner as in Example 9, except that the compound (5) was used instead of the compound (3). Apply a DC voltage of 10 V to this element.
Upon application, blue light emission of 9,200 cd / m ² was obtained. The maximum luminous efficiency was 2.4 lm / W.

Example 11 An organic EL device was produced in the same manner as in Example 9, except that Compound (1) was used in place of Compound (3) and [09] was used as an electron transport layer.
When a DC voltage of 10 V was applied to this element,
Blue light emission of 0 cd / m ² was obtained. The maximum luminous efficiency was 2.8 lm / W.

(Embodiment 12) FIG. 3 shows a sectional structure of an element used in Embodiment 12. The device is composed of an anode / a hole transport layer / a light emitting layer / a cathode. ITO on glass substrate
Was formed by sputtering so that the sheet resistance became 20 Ω / □, and used as an anode. [03] was formed thereon as a hole transporting layer by vacuum evaporation at a thickness of 50 nm. next,
As a light emitting layer, a film was formed by vacuum co-evaporation of [11] and compound (1) at a weight ratio of 20: 1 to form a film having a thickness of 50 nm. Next, a 200 nm thick magnesium-silver alloy is formed as a cathode and EL
An element was manufactured. When a DC voltage of 10 V was applied to this device, blue light emission of 5,500 cd / m ² was obtained.
The maximum luminous efficiency was 2.2 lm / W.

Example 13 As a light emitting layer, [11] and compound (2) were vacuum co-deposited at a weight ratio of 20: 1.
An organic EL device was manufactured in the same manner as in Example 12 except that a film having a thickness of nm was used. Apply a DC voltage of 10 V to this element.
Upon application, blue light emission of 6,000 cd / m ² was obtained. The maximum luminous efficiency was 2.1 lm / W.

Example 14 An ITO was formed on a glass substrate by sputtering so that the sheet resistance became 20 Ω / □, and used as an anode. [03] was formed thereon as a hole transporting layer by vacuum evaporation at a thickness of 50 nm. A compound (2) was formed thereon as a light emitting layer by vacuum evaporation to a thickness of 40 nm, and then a magnesium-silver alloy was formed as a cathode with a thickness of 200 nm.
m was formed to produce an EL element. When a DC voltage of 10 V was applied to this device, blue light emission of 4,000 cd / m ² was obtained. The maximum luminous efficiency is 1.3 lm / W
Met.

(Example 15) [01] as a hole transport layer
Example 1 was repeated except that the compound (4) was used as the light emitting layer.
The same operation as in Example 4 was performed to produce an organic EL device. When a DC voltage of 10 V was applied to this element, 4,100 cd / m
² blue luminescence was obtained. The maximum luminous efficiency is 1.2
lm / W.

[0071]

As described above, by using the compound of the present invention in the emission band of the organic EL device, high-luminance blue light emission with excellent color purity can be obtained, and the effect of the present invention is great.

[Brief description of the drawings]

FIG. 1 is a sectional view of an element of the present invention.

FIG. 2 is a sectional view of the device of the present invention.

FIG. 3 is a sectional view of the device of the present invention.

FIG. 4 is a cross-sectional view of the device of the present invention.

[Explanation of symbols]

 DESCRIPTION OF SYMBOLS 1 Substrate 2 Anode 3 Hole transport layer 4 Light emitting layer 5 Electron transport layer 6 Cathode

──────────────────────────────────────────────────続 き Continuation of the front page (72) Inventor Atsushi Oda 5-7-1 Shiba, Minato-ku, Tokyo NEC Corporation (56) References JP-A-10-88120 (JP, A) JP-A-9 -268284 (JP, A) JP-A-11-74079 (JP, A) JP-A-11-8068 (JP, A) JP-A-10-251633 (JP, A) (58) Fields investigated (Int. . ^7, DB name) C09K 11/06 CA (STN) REGISTRY (STN)

Claims (3)

(57) [Claims] 1. An organic electroluminescent device having at least a light emitting layer between an anode and a cathode, wherein the light emitting layer contains a material represented by the following general formula [1] alone or as a mixture. element. Embedded image (However, Ar _{1 to} Ar ₄ are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, at least one of which is a styryl group represented by the following general formula [2]. Ar ₁ and Ar ₂ and Ar ₃ and Ar ₄ may form a ring with each other, and R _{1 to} R ₆ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a cyano group, Group, nitro group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted Or an unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group,
Represents a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, or a carboxyl group, wherein at least one of R ₁ and R ₄ is other than a hydrogen atom
Groups and both of them are groups other than hydrogen atoms
Absent. ) (However, R _{7 to} R ₁₇ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group (excluding diphenylamino group), a cyano group, a nitro group, a substituted or unsubstituted Alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, A substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group,
A substituted or unsubstituted alkoxycarbonyl group or carboxyl group. ) 2. An organic electroluminescent device having at least a light emitting layer between an anode and a cathode, wherein the light emitting layer contains a material represented by the following general formula [3] alone or as a mixture. element. Embedded image (However, Ar _{5 to} Ar ₈ are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, at least one of which is a styryl group represented by the following general formula [2]. Ar ₅ and Ar ₆ and Ar ₇ and Ar ₈ may form a ring with each other, and R _{18 to} R ₂₃ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, Group, nitro group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted Or an unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group,
Represents a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, or a carboxyl group, wherein at least one of R ₁₈ and R ₁₉ is other than a hydrogen atom
And both are non-hydrogen groups
There is no. ) (However, R _{7 to} R ₁₇ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group (excluding diphenylamino group), a cyano group, a nitro group, a substituted or unsubstituted Alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, A substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group,
A substituted or unsubstituted alkoxycarbonyl group or carboxyl group. ) 3. An organic electroluminescent device having at least a light emitting layer between an anode and a cathode, wherein the light emitting layer contains a material represented by the following general formula [4] alone or as a mixture. element. Embedded image (However, Ar _{9 to} Ar ₁₂ are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, at least one of which is a styryl group represented by the following general formula [2]. Ar ₉ and Ar ₁₀ and Ar ₁₁ and Ar ₁₂ may form a ring with each other, and R _{24 to} R ₂₉ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a cyano group, Group, nitro group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted Or an unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group,
Represents a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, or a carboxyl group, wherein at least one of R ₂₄ , R ₂₆ , R ₂₇ , and R ₂₉ is a group other than a hydrogen atom, and All are not groups other than hydrogen atoms. ) (However, R _{7 to} R ₁₇ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group (excluding diphenylamino group), a cyano group, a nitro group, a substituted or unsubstituted Alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, A substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group,
A substituted or unsubstituted alkoxycarbonyl group or carboxyl group. )