WO2010010924A1

WO2010010924A1 - Anthracene derivative, and organic electroluminescence element comprising same

Info

Publication number: WO2010010924A1
Application number: PCT/JP2009/063192
Authority: WO
Inventors: 河村　昌宏; 光則伊藤
Original assignee: 出光興産株式会社
Priority date: 2008-07-25
Filing date: 2009-07-23
Publication date: 2010-01-28
Also published as: TW201016638A

Abstract

An anthracene derivative represented by formula (1) (excluding a compound represented by formula (1')).

Description

Anthracene derivative and organic electroluminescence device using the same

The present invention relates to an anthracene derivative and an organic electroluminescence element using the anthracene derivative.

Conventionally, an organic EL element (organic electroluminescence element) using light emission of an organic compound is known. The organic EL element has a plurality of organic thin films stacked between an anode and a cathode. In this configuration, when a voltage is applied between the anode and the cathode, holes and electrons are injected into the organic thin film from the anode and the cathode, respectively. Excited molecules are generated in the light emitting layer in the organic thin film by the injected holes and electrons. Then, energy when returning from the excited state to the ground state is emitted as light.

Patent Documents 1 to 10 disclose materials that can be used for the light emitting layer. However, any of the materials has problems such as low luminous efficiency and short lifetime of the organic EL element obtained.
International Publication No. 02/038524 Pamphlet Japanese Patent Laid-Open No. 2004-059535 Korean Patent Application Publication No. 10-2007-0101722 Specification US Pat. No. 7,326,371 JP 2005-170911 A International Publication No. 08/013399 Pamphlet International Publication No. 07/021117 Pamphlet JP 2003-146951 A International Publication No. 07/127078 Pamphlet International Publication No. 07/130259 Pamphlet

An object of the present invention is to provide a novel luminescent material and an organic EL element using the luminescent material.

As a result of intensive studies to solve the above problems, the present inventors have found that the following problems can be solved by the present invention.
According to the present invention, the following anthracene derivatives and the like are provided.
1. Anthracene derivatives represented by the following formula (1) (excluding those represented by the following formula (1 ′)).

Wherein R ₁ to R ₇ are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted carbon, An alkoxy group of 1 to 50, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group.
R ₁₁ to R ₁₅ and R ₂₁ to R ₂₅ are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted group An alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted condensed aromatic group having 10 to 50 carbon atoms, a substituted or unsubstituted number of nuclear atoms It is a 5-50 heterocyclic group, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group.
Provided that at least one of R ₁₁ to R ₁₅ and R ₂₁ to R ₂₅ is a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 nuclear atoms. It is a group.
Ar ₁ is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms.
However, Ar ₁ does not include an orthophenylene structure. )
2. Any one of R ₁₁ to R ₁₅ is a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms,
Substituted or unsubstituted fused aromatic group having 10 to 50 carbon atoms, or all of _R 11 _{~ R 15} other than _R 11 _{~ R 15} is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms is A hydrogen atom,
Any one of R ₂₁ to R ₂₅ is a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms,
Substituted or unsubstituted fused aromatic group having 10 to 50 carbon atoms, or all of _R 21 _{~ R 25} other than _R 21 _{~ R 25} is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms is 2. The anthracene derivative according to 1, which is a hydrogen atom.
3. R ₁₂ and R ₂₂ are each a substituted or unsubstituted condensed aromatic ring group having 10 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, and R ₁₁ , R ₁₃ , 2. The anthracene derivative according to 1, wherein R ₁₄ , R ₁₅ , R ₂₁ , R ₂₃ , R ₂₄ and R ₂₅ are hydrogen atoms.
4). R ₁₃ and R ₂₃ are each a substituted or unsubstituted condensed aromatic ring group having 10 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nucleus atoms, and R ₁₁ , R ₁₂ , 2. The anthracene derivative according to 1, wherein R ₁₄ , R ₁₅ , R ₂₁ , R ₂₂ , R ₂₄ and R ₂₅ are hydrogen atoms.
5). Ar ₁ is an unsubstituted phenyl group, a fluorenyl group having a substituent at the 9-position, an unsubstituted condensed aromatic group having 10 to 20 nuclear carbon atoms, or an unsubstituted heterocyclic group having 5 to 20 nuclear atoms. An anthracene derivative according to any one of 1 to 4.
6). 6. The anthracene derivative according to any one of 1 to 5, wherein the condensed aromatic group of Ar ₁ is a naphthyl group, a phenanthryl group, a pyrenyl group, or a fluoranthenyl group. 7). 7. The anthracene derivative according to any one of 1 to 6, wherein R ₁ to R ₇ are hydrogen atoms. 8). 8. A material for an organic electroluminescence device comprising the anthracene derivative according to any one of 1 to 7 above.
9. 9. The material for an organic electroluminescence device according to 8, which is a light emitting material.
10. An anode and a cathode;
Having one or more organic thin film layers including a light emitting layer sandwiched between the anode and the cathode;
The organic electroluminescent element in which at least 1 layer of the said organic thin film layer contains the organic electroluminescent element material of 8.
11. 11. The organic electroluminescence device according to 10, wherein the light emitting layer contains the material for an organic electroluminescence device.
12 12. The organic electroluminescence device according to 11, wherein the material for an organic electroluminescence device is a host material.
13. An anode and a cathode, and one or more organic thin film layers including a light emitting layer sandwiched between the anode and the cathode, wherein the light emitting layer is an anthracene derivative represented by the following formula (1) as a host material And an organic electroluminescence device containing at least one of a fluorescent dopant and a phosphorescent dopant.

Wherein R ₁ to R ₇ are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted carbon, An alkoxy group of 1 to 50, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group.
R ₁₁ to R ₁₅ and R ₂₁ to R ₂₅ are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted group An alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted condensed aromatic group having 10 to 50 carbon atoms, a substituted or unsubstituted number of nuclear atoms It is a 5-50 heterocyclic group, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group.
Provided that at least one of R ₁₁ to R ₁₅ and R ₂₁ to R ₂₅ is a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 nuclear atoms. It is a group.
Ar ₁ is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms.
However, Ar ₁ does not include an orthophenylene structure. )
14 14. The organic electroluminescence device according to 13, wherein the fluorescent dopant is a styrylamine compound.
15. 14. The organic electroluminescence device according to 13, wherein the fluorescent dopant is an arylamine compound.
16. 16. The organic electroluminescence device according to 15, wherein the arylamine compound is a compound represented by the following formula (2).

(Wherein R ^e is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, Substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted Aryloxy group having 6 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted ring formation An arylsilyl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkylgermanium group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl having 6 to 50 ring carbon atoms It is a germanium group.
t is an integer of 0 to 10.
Ar ³ to Ar ⁶ are each a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms. )
17. 16. The organic electroluminescence device according to 15, wherein the arylamine compound is a compound represented by the following formula (3).

(Wherein R ^f represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, Substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted Aryloxy group having 6 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted ring formation An arylsilyl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkylgermanium group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl having 6 to 50 ring carbon atoms It is a germanium group.
u is an integer of 0-8.
Ar ⁷ to Ar ¹⁰ are each a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 20 ring atoms. )
18. 16. The organic electroluminescence device according to 15, wherein the arylamine compound is a compound represented by the following formula (4).

(Wherein R ^g is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, Substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted Aryloxy group having 6 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted ring formation An arylsilyl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkylgermanium group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl having 6 to 50 ring carbon atoms It is a germanium group.
q is an integer of 0-6.
R ³⁰ and R ³¹ are each a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 20 nuclear atoms.
Ar ¹¹ to Ar ¹⁴ are each a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 20 ring atoms. )

According to the present invention, a novel light emitting material and an organic EL element using the light emitting material can be provided.

The anthracene derivative of the present invention is a compound represented by the following formula (1).

Wherein R ₁ to R ₇ are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted carbon, An alkoxy group of 1 to 50, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group.
R ₁₁ to R ₁₅ and R ₂₁ to R ₂₅ are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted group An alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted condensed aromatic group having 10 to 50 carbon atoms, a substituted or unsubstituted number of nuclear atoms It is a 5-50 heterocyclic group, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group.
Provided that at least one of R ₁₁ to R ₁₅ and R ₂₁ to R ₂₅ is a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 nuclear atoms. It is a group.
Ar ₁ is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms.
However, Ar ₁ does not include an orthophenylene structure. )

In the present invention, the “hydrogen atom” includes a deuterium atom.
In the present invention, “nuclear carbon” means a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring. The “nuclear atom” means a carbon atom and a hetero atom constituting a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring). For example, a phenyl group substituted with a naphthyl group is a substituted aryl group having 16 carbon atoms, and a phenyl group substituted with a methyl group is an aryl group having 6 substituted nuclear carbon atoms.
In the definition of each formula of the present invention, the substituent in “substituted or unsubstituted...” Includes an alkyl group, aryl group, cycloalkyl group, alkoxy group, heterocyclic group, halogen atom as described later. , A hydroxyl group, a nitro group, a cyano group, etc., preferably an alkyl group, an aryl group, a cycloalkyl group, or a heterocyclic group.

As described above, Ar ₁ of the anthracene derivative of the present invention does not include an orthophenylene structure. The fact that it does not contain an orthophenylene structure means that it does not have a substituent at the ortho position of the phenyl moiety of Ar ₁ directly bonded to the anthracene skeleton of the anthracene derivative of the present invention.
For example, when Ar ₁ is a phenyl group, the following anthracene derivatives are not included in the present invention.

(In the formula, X is a substituent.)

In addition, the anthracene derivative of the present invention may exclude those represented by the following formula (1 ′).

Ar ₁ is preferably an unsubstituted phenyl group, a fluorenyl group having a substituent at the 9-position, an unsubstituted condensed aromatic group having 10 to 20 nuclear carbon atoms, or an unsubstituted heterocyclic ring having 5 to 20 nuclear atoms. It is a group.

R ₁ to R ₇ of the anthracene derivative of the present invention are preferably hydrogen atoms from the viewpoint that it is easy to obtain light of a low wavelength side such as blue.

In addition, R ¹¹ to R ¹⁵ and R ²¹ to ²⁵ of the anthracene derivative of the present invention preferably satisfy any of the following (A) to (D).
(A) At least one of R ₁₁ to R ₁₅ and at least one of R ₂₁ to R ₂₅ are each a substituted or unsubstituted condensed aromatic ring group having 10 to 50 nuclear carbon atoms. (B) R ₁₂ and R ₂₂ are each a substituted or unsubstituted condensed aromatic ring group having 10 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nucleus atoms, R ₁₁ , R ₁₃ , R ₁₄ , R ₁₅ , R ₂₁ , R ₂₃ , R ₂₄ and R ₂₅ are hydrogen atoms.
(C) R ₁₃ and R ₂₃ are each a substituted or unsubstituted condensed aromatic ring group having 10 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nucleus atoms, R ₁₁ , R ₁₂ , R ₁₄ , R ₁₅ , R ₂₁ , R ₂₂ , R ₂₄ and R ₂₅ are hydrogen atoms.
(D) any one of R ₁₁ to R ₁₅ is a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms; or unsubstituted condensed aromatic group having 10 to 50 carbon atoms, or a substituted or all of _R 11 _{~ R 15} other than _R 11 _{~ R 15} is a heterocyclic group having 5 to 50 ring atoms unsubstituted hydrogen And any one of R ₂₁ to R ₂₅ is a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, substituted or unsubstituted fused aromatic group having 10 to 50 carbon atoms, or all of _R 21 _{~ R 25} other than _R 21 _{~ R 25} is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms is It is a hydrogen atom.

Examples of the alkyl group having 1 to 20 carbon atoms of R ₁ to R ₇ , R ₁₁ to R ₁₅ and R ₂₁ to R ₂₅ include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, and an 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, 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-sia Ethyl 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, Examples include 2,3-trinitropropyl group. Preferred are methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group and t-butyl group.

Examples of the cycloalkyl group having 3 to 20 carbon atoms of R ₁ to R ₇ , R ₁₁ to R ₁₅ and R ₂₁ to R ₂₅ include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, 1 -Adamantyl group, 2-adamantyl group, 1-norbornyl group, 2-norbornyl group and the like. Preferably, it is a cyclopentyl group or a cyclohexyl group.

The substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms of R ₁ to R ₇ , R ₁₁ to R ₁₅ and R ₂₁ to R ₂₅ is a group represented by —OZ, and Z is a group represented by R ₁ to R ₇ is selected from alkyl groups having 1 to 20 carbon atoms. Z is preferably a methyl group or an ethyl group.

Examples of substituted or unsubstituted silyl groups for R ₁ to R ₇ , R ₁₁ to R ₁₅ and R ₂₁ to R ₂₅ include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group. Group, triphenylsilyl group and the like. A trimethylsilyl group or a triphenylsilyl group is preferable.

Examples of the substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms for R ₁₁ to R ₁₅ , R ₂₁ to R ₂₅ and Ar ₁ include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 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, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 6-chrysenyl group, 1-benzo [c] phenanthryl group, 2-benzo [c] phenanthryl group, 3-benzo [c] phenanthryl group, 4-benzo [C] phenanthryl group, 5-benzo [c] phenanthryl group, 6-benzo [c] phenanthryl group, 1-benzo [g] chrysene Group, 2-benzo [g] chrysenyl group, 3-benzo [g] chrysenyl group, 4-benzo [g] chrysenyl group, 5-benzo [g] chrysenyl group, 6-benzo [g] chrysenyl group, 7- Benzo [g] chrysenyl group, 8-benzo [g] chrysenyl group, 9-benzo [g] chrysenyl group, 10-benzo [g] chrysenyl group, 11-benzo [g] chrysenyl group, 12-benzo [g] chrysenyl group Group, 13-benzo [g] chrysenyl group, 14-benzo [g] chrysenyl group, 1-triphenyl group, 2-triphenyl group, 2-fluorenyl group, 9,9-dimethylfluoren-2-yl group, benzo Fluorenyl group, dibenzofluorenyl 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 group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, pt-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 and the like. From the viewpoint of appropriate molecular weight and durability against redox, it is preferable. Is a substituted or unsubstituted phenyl group and a substituted or unsubstituted aryl group having 10 to 14 nuclear carbon atoms (eg, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group), substituted or unsubstituted fluorenyl group (2 -Fluorenyl group), and substituted or unsubstituted pyrenyl groups (1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group).

Examples of the substituted or unsubstituted heterocyclic group having 5 to 50 nucleus atoms of R ₁₁ to R ₁₅ , R ₂₁ to R ₂₅ and Ar ₁ include 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 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 group 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1-i Benzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group, 4-dibenzothiophenyl group, 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 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-phenanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, -Acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1,7-phenanthrolin-2-yl group, 1,7-phenanthroline-3-yl group, 1,7- Phenanthroline-4-yl group, 1,7-phenanthroline-5-yl group, 1,7-phenanthroline-6-yl group, 1,7-phenanthroline-8-yl group 1,7-phenanthroline-9-yl group, 1,7-phenanthroline-10-yl group, 1,8-phenanthroline-2-yl group, 1,8-phenanthroline-3-yl group, 1,8-phenanthroline- 4-yl group, 1,8-phenanthroline-5-yl group, 1,8-phenanthroline-6-yl group, 1,8-phenanthroline-7-yl group, 1,8-phenanthroline-9-yl group, 1 , 8-phenanthroline-10-yl group, 1,9-phenanthroline-2-yl group, 1,9-phenanthroline-3-yl group, 1,9-phenanthroline-4-yl group, 1,9-phenanthroline-5 -Yl group, 1,9-phenanthroline-6-yl group, 1,9-phenanthroline-7-yl group, 1,9-phenanthroline-8-yl group, 1,9-phena Trolin-10-yl group, 1,10-phenanthroline-2-yl group, 1,10-phenanthroline-3-yl group, 1,10-phenanthroline-4-yl group, 1,10-phenanthroline-5-yl group 2,9-phenanthroline-1-yl group, 2,9-phenanthroline-3-yl group, 2,9-phenanthroline-4-yl group, 2,9-phenanthroline-5-yl group, 2,9-phenanthroline -6-yl group, 2,9-phenanthroline-7-yl group, 2,9-phenanthroline-8-yl group, 2,9-phenanthroline-10-yl group, 2,8-phenanthroline-1-yl group, 2,8-phenanthroline-3-yl group, 2,8-phenanthroline-4-yl group, 2,8-phenanthroline-5-yl group, 2,8-phenanthroline -6-yl group, 2,8-phenanthroline-7-yl group, 2,8-phenanthroline-9-yl group, 2,8-phenanthroline-10-yl group, 2,7-phenanthroline-1-yl group, 2,7-phenanthroline-3-yl group, 2,7-phenanthroline-4-yl group, 2,7-phenanthroline-5-yl group, 2,7-phenanthroline-6-yl group, 2,7-phenanthroline- 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, 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-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-india 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, etc. . From the viewpoint of durability against redox, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group Group, 3-dibenzothiophenyl group, 4-dibenzothiophenyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group and 9-carbazolyl group are preferable.

Examples of the substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms of R ₁₁ to R ₁₅ and R ₂₁ to R ₂₅ include a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, and a 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, 1-pyrenyl group 2-pyrenyl group, 4-pyrenyl group, 2-fluorenyl group and the like. In particular, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group, pyrenyl group (1-pyrenyl group, 2-pyrenyl group and 4-pyrenyl group) from the viewpoint of appropriate molecular weight and durability to redox And a fluorenyl group (2-fluorenyl group) are preferred.
These substituents may further have a substituent such as an alkyl group, a cycloalkyl group, an alkoxy group, a cyano group, a silyl group, an aryl group, a heterocyclic group, a halogen atom, etc. An alkyl group, an aryl group, and a heterocyclic group are preferable, and an aryl group and a heterocyclic group are more preferable. Specific examples of these substituents are as described above.

Hereinafter, specific examples of the anthracene derivative of the present invention and the anthracene derivative as a host used in combination with the dopant in the organic electroluminescence device will be shown.

The above specific examples are only a part of the anthracene derivatives of the present invention. Needless to say, the anthracene derivatives of the present invention not shown in the specific examples have the same effects as the anthracene derivatives shown in the specific examples.

The anthracene derivative of the present invention can be synthesized, for example, by the method described in WO2004 / 018587. Specific synthesis methods are shown in the examples described later.

The anthracene derivative of the present invention can be used as a light emitting material for an organic EL device, and is preferably used as a host material.

The organic EL device of the present invention is a device in which one or more organic thin film layers are formed between an anode and a cathode. When the organic thin film layer is a plurality of layers, one layer is a light emitting layer. When the number of organic thin film layers is one, a light emitting layer as an organic thin film layer is formed between the anode and the cathode. At least one of the organic thin film layers (preferably the light-emitting layer) contains the anthracene derivative of the present invention, and further transports holes injected from the anode or electrons injected from the cathode to the light-emitting material. Further, a hole injection material or an electron injection material may be contained. Since the anthracene derivative of the present invention has its characteristic steric structure, it has high emission characteristics.

In the organic thin film layer of the organic EL element of the present invention, a material other than the anthracene derivative of the present invention may be used in combination. For example, compounds represented by the following (i) to (ix) can be used as a host material used in combination in the light emitting layer of the organic EL device of the present invention.

Asymmetric anthracene represented by the following formula (i).

(In the formula, Ar ⁰⁰¹ is a substituted or unsubstituted condensed aromatic hydrocarbon group having 10 to 50 nuclear carbon atoms. Ar ⁰⁰² is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms. X ⁰⁰¹ to X ⁰⁰³ are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms, substituted or unsubstituted A substituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted nuclear atom number of 5 to 50 Aryloxy group, substituted or unsubstituted arylthio group having 5 to 50 nucleus atoms, substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, carboxyl group, halogen atom, cyano , A nitro group, and a hydroxy group, a, b and c are each an integer of 0 to 4. n is an integer of 1 to 3. When n is 2 or more, [] Same or different.)

An asymmetric monoanthracene derivative represented by the following formula (ii).

(In the formula, Ar ⁰⁰³ and Ar ⁰⁰⁴ are each independently a substituted or unsubstituted aromatic ring group having 6 to 50 nuclear carbon atoms, and m and n are each an integer of 1 to 4, provided that When m = n = 1 and the binding position of Ar ⁰⁰³ and Ar ^{004 to} the benzene ring is symmetrical, Ar ⁰⁰³ and Ar ⁰⁰⁴ are not the same, and m or n is an integer of 2 to 4 M and n are different integers.
R ⁰⁰¹ to R ⁰¹⁰ are each independently a hydrogen atom, a substituted or unsubstituted aromatic ring group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms, a substituted group Or an unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, Substituted or unsubstituted aryloxy group having 5 to 50 nucleus atoms, substituted or unsubstituted arylthio group having 5 to 50 nucleus atoms, substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, substituted or unsubstituted A silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, and a hydroxy group. )

An asymmetric pyrene derivative represented by the following formula (iii).

[ ^Wherein , Ar ⁰⁰⁵ and Ar ⁰⁰⁶ are each a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms. L ⁰⁰¹ and L ⁰⁰² are a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenylene group, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted dibenzosilolylene group, respectively.
m is an integer from 0 to 2, n is an integer from 1 to 4, s is an integer from 0 to 2, and t is an integer from 0 to 4.
L ⁰⁰¹ or Ar ⁰⁰⁵ binds to any of the 1-5 positions of pyrene, and L ⁰⁰² or Ar ⁰⁰⁶ binds to any of the 6-10 positions of pyrene. However, when n + t is an even number, Ar ⁰⁰⁵ , Ar ⁰⁰⁶ , L ⁰⁰¹ , and L ⁰⁰² satisfy the following (1) or (2).
(1) Ar ⁰⁰⁵ ≠ Ar ⁰⁰⁶ and / or L ⁰⁰¹ ≠ L ⁰⁰² (where ≠ indicates a group having a different structure)
(2) When Ar ⁰⁰⁵ = Ar ⁰⁰⁶ and L ⁰⁰¹ = L ⁰⁰² (2-1) m ≠ s and / or n ≠ t, or (2-2) When m = s and n = t,
(2-2-1) L ⁰⁰¹ and L ⁰⁰² or pyrene are bonded to different bonding positions on Ar ⁰⁰⁵ and Ar ⁰⁰⁶ , respectively (2-2-2) L ⁰⁰¹ and L ⁰⁰² , or pyrene is , Ar ⁰⁰⁵ and Ar ⁰⁰⁶ are bonded at the same bonding position, and the substitution positions in pyrene of L ⁰⁰¹ and L ⁰⁰² or Ar ⁰⁰⁵ and Ar ⁰⁰⁶ are 1-position and 6-position, or 2-position and 7-position There is no. ]

An asymmetric anthracene derivative represented by the following formula (iv):

(In the formula, A ⁰⁰¹ and A ⁰⁰² are each independently a substituted or unsubstituted condensed aromatic ring group having 10 to 20 nuclear carbon atoms.
Ar ⁰⁰⁷ and Ar ⁰⁰⁸ are each independently a hydrogen atom or a substituted or unsubstituted aromatic ring group having 6 to 50 nuclear carbon atoms.
R ⁰¹¹ to R ⁰²⁰ are each independently a hydrogen atom, a substituted or unsubstituted aromatic ring group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms, a substituted group Or an unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, Substituted or unsubstituted aryloxy group having 5 to 50 nucleus atoms, substituted or unsubstituted arylthio group having 5 to 50 nucleus atoms, substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, substituted or unsubstituted A silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxy group.
Ar ⁰⁰⁷ , Ar ⁰⁰⁸ , R ⁰¹⁹ and R ⁰²⁰ may each be plural, and adjacent ones may form a saturated or unsaturated cyclic structure.
However, in the formula (iv), a group that is symmetrical with respect to the XY axis shown on the anthracene is not bonded to the 9th and 10th positions of the central anthracene. )

An anthracene derivative represented by the following formula (v).

(Wherein R ⁰²¹ to R ⁰³⁰ are each independently a hydrogen atom, alkyl group, cycloalkyl group, optionally substituted aryl group, alkoxyl group, aryloxy group, alkylamino group, alkenyl group, arylamino group, or substituted. A and b each represent an integer of 1 to 5, and when they are 2 or more, R ^021s or R ^022s may be the same or different from each other Alternatively, R ⁰²¹ or R ⁰²² may be bonded to each other to form a ring, and R ⁰²³ and R ⁰²⁴ , R ⁰²⁵ and R ⁰²⁶ , R ⁰²⁷ and R ⁰²⁸ , R ⁰²⁹ and R ⁰³⁰ are L ⁰⁰³ may be a single bond, —O—, —S—, —N (R) — (where R is an alkyl group or an aryl group which may be substituted). Represents an alkylene group or an arylene group.)

An anthracene derivative represented by the following formula (vi).

(Wherein R ⁰³¹ to R ⁰⁴⁰ each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an alkoxyl group, an aryloxy group, an alkylamino group, an arylamino group, or an optionally substituted multicyclic group) C, d, e and f each represent an integer of 1 to 5, and when they are 2 or more, R ^{031 to} each other, R ^{032 to} each other, R ^{036 to} each other or R ^{037 to} each other may be the same may be different, also ^{R 031} ^{together, R 032} ^together, may also be ^{R 033} s or ^{R 037} are bonded to each other to form a ^{ring, R 033} and ^R ^{034, R 039} and ^{R 040} are each other bonded to ring the optionally formed .L ⁰⁰⁴ is a single bond, -O -, - S -, - N (R) - (R is an aryl group which may be alkyl or substituted), Al Shows the alkylene group or an arylene group.)

Spirofluorene derivatives represented by the following formula (vii).

( ^Wherein A ⁰⁰⁵ to A ⁰⁰⁸ are each independently a substituted or unsubstituted biphenylyl group or a substituted or unsubstituted naphthyl group.)

A condensed ring-containing compound represented by the following formula (viii):

( ^Wherein A ⁰¹¹ to A ⁰¹³ are each independently a substituted or unsubstituted arylene group having 6 to 50 nuclear carbon atoms. A ⁰¹⁴ to A ⁰¹⁶ are each independently a hydrogen atom, or a substituted or unsubstituted group. A substituted aryl group having 6 to 50 carbon atoms, R ⁰⁴¹ to R ⁰⁴³ each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or 1 carbon atom; Alkoxy group having 6 to 6 carbon atoms, aryloxy group having 5 to 18 carbon atoms, aralkyloxy group having 7 to 18 carbon atoms, arylamino group having 5 to 16 carbon atoms, nitro group, cyano group, ester group having 1 to 6 carbon atoms Or a halogen atom, and at least one of A ⁰¹¹ to A ⁰¹⁶ is a group having three or more condensed aromatic rings.)

A fluorene compound represented by the following formula (ix).

Wherein R ⁰⁵¹ and R ⁰⁵² are a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aromatic heterocyclic group, a substituted amino group, ^{R 051} together to bind to. different fluorene group represents a cyano group or a halogen ^{atom, R 052} each other, or different, even the same, ^{R 051} and ^{R 052} bonding to the same fluorene group, R ⁰⁵³ and R ⁰⁵⁴ may be a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted group. R ⁰⁵³ and R ⁰⁵⁴ representing an aromatic heterocyclic group and bonded to different fluorene groups are the same or different. R ⁰⁵³ and R ⁰⁵⁴ bonded to the same fluorene group may be the same or different, and Ar ⁰¹¹ and Ar ⁰¹² may be a substituted or unsubstituted condensed group having a total of 3 or more benzene rings. A polycyclic aromatic hydrocarbon group or a condensed polycyclic aromatic heterocyclic group in which a total of three or more substituted or unsubstituted carbons of a benzene ring and a heterocyclic ring is bonded to a fluorene group, Ar ⁰¹¹ and Ar ⁰¹² are (It may be the same or different. N represents an integer of 1 to 10.)

The light emitting layer of the organic EL device of the present invention preferably contains a phosphorescent dopant and / or a fluorescent dopant. Further, a light emitting layer containing these dopants may be stacked on the light emitting layer containing the anthracene derivative of the present invention.

A phosphorescent dopant is a compound that can emit light from triplet excitons. Although it is not particularly limited as long as it emits light from triplet excitons, it is preferably a metal complex containing at least one metal selected from the group consisting of Ir, Ru, Pd, Pt, Os and Re, and is preferably a porphyrin metal complex or ortho Metalated metal complexes are preferred. The phosphorescent compounds may be used alone or in combination of two or more.

The porphyrin metal complex is preferably a porphyrin platinum complex.
There are various ligands that form orthometalated metal complexes. Preferred ligands include compounds having a phenylpyridine skeleton, bipyridyl skeleton or phenanthroline skeleton, or 2-phenylpyridine derivatives, 7,8. -Benzoquinoline derivatives, 2- (2-thienyl) pyridine derivatives, 2- (1-naphthyl) pyridine derivatives, 2-phenylquinoline derivatives and the like. These ligands may have a substituent as needed. In particular, a fluorinated compound or a compound having a trifluoromethyl group introduced is preferable as a blue dopant. Furthermore, you may have ligands other than the said ligands, such as an acetylacetonate and picric acid, as an auxiliary ligand.

Specific examples of such metal complexes include tris (2-phenylpyridine) iridium, tris (2-phenylpyridine) ruthenium, tris (2-phenylpyridine) palladium, bis (2-phenylpyridine) platinum, tris (2- Phenylpyridine) osmium, tris (2-phenylpyridine) rhenium, octaethylplatinum porphyrin, octaphenylplatinum porphyrin, octaethylpalladium porphyrin, octaphenylpalladium porphyrin, etc. An appropriate complex is selected depending on the device performance and the host compound to be used.

There is no restriction | limiting in particular as content in the light emitting layer of a phosphorescent dopant, Although it can select suitably according to the objective, For example, it is 0.1-70 mass%, and 1-30 mass% is preferable. If the content of the phosphorescent compound is less than 0.1% by mass, the light emission is weak and the effect of the content may not be sufficiently exhibited. If the content exceeds 70% by mass, a phenomenon called concentration quenching becomes prominent. The device performance may be degraded.

Fluorescent dopants are required from amine compounds, aromatic compounds, chelate complexes such as tris (8-quinolinolato) aluminum complex, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives, oxadiazole derivatives, etc. It is preferable to select a compound in accordance with the emission color, and a styrylamine compound, a styryldiamine compound, an arylamine compound, and an aryldiamine compound are more preferable. Moreover, the condensed polycyclic aromatic compound which is not an amine compound is also preferable. These fluorescent dopants may be used alone or in combination.

As the styrylamine compound and styryldiamine compound, those represented by the following formula (A) are preferable.

(In the formula, Ar ¹⁰¹ is a p-valent group, and a corresponding p-valent group of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a stilbenyl group, or a distyrylaryl group, and Ar ¹⁰² and Ar ¹⁰³ are Each of them is an aromatic hydrocarbon group having 6 to 20 carbon atoms, and Ar ¹⁰¹ , Ar ¹⁰² and Ar ¹⁰³ may be substituted, and any one of Ar ¹⁰¹ to Ar ¹⁰³ is substituted with a styryl group. More preferably, at least one of Ar ^{102 and} Ar ¹⁰³ is substituted with a styryl group, and p is an integer of 1 to 4, and preferably an integer of 1 to 2.
Here, examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include a phenyl group, a naphthyl group, an anthranyl group, a phenanthryl group, and a terphenyl group.

As the arylamine compound and the aryldiamine compound, those represented by the following formula (B) are preferable.

(In the formula, Ar ¹¹¹ is a q-valent substituted or unsubstituted aromatic hydrocarbon group having 5 to 40 nuclear carbon atoms, and Ar ¹¹² and Ar ¹¹³ are each substituted or unsubstituted aryl having 5 to 40 nuclear carbon atoms. Q is an integer of 1 to 4, preferably an integer of 1 to 2.)
Here, examples of the aryl group having 5 to 40 nuclear carbon atoms include phenyl, naphthyl, anthranyl, phenanthryl, pyrenyl, coronyl, biphenyl, terphenyl, pyrrolyl, furyl, thienyl. Group, benzothienyl group, oxadiazolyl group, diphenylanthranyl group, indolyl group, carbazolyl group, pyridyl group, benzoquinolyl group, fluoranthenyl group, acenaphthofluoranthenyl group, stilbene group, perylenyl group, chrysenyl group, picenyl group, triphenylenyl Group, rubicenyl group, benzoanthracenyl group, phenylanthranyl group, bisanthracenyl group and the like, and naphthyl group, anthranyl group, chrycenyl group and pyrenyl group are preferable.

Preferred substituents substituted on the aryl group include alkyl groups having 1 to 6 carbon atoms (ethyl group, methyl group, i-propyl group, n-propyl group, s-butyl group, t-butyl group, pentyl group). Hexyl group, cyclopentyl group, cyclohexyl group, etc.), alkoxy group having 1 to 6 carbon atoms (ethoxy group, methoxy group, i-propoxy group, n-propoxy group, s-butoxy group, t-butoxy group, pentoxy group, Hexyloxy group, cyclopentoxy group, cyclohexyloxy group, etc.), aryl group having 5 to 40 nuclear carbon atoms, amino group substituted with an aryl group having 5 to 40 nuclear carbon atoms, aryl group having 5 to 40 nuclear carbon atoms An ester group having an alkyl group, an ester group having an alkyl group having 1 to 6 carbon atoms, a cyano group, a nitro group, a halogen atom, and the like.

The light emitting layer may contain a hole transport material, an electron transport material, and a polymer binder as necessary.
The thickness of the light emitting layer is preferably 5 to 50 nm, more preferably 7 to 50 nm, and most preferably 10 to 50 nm. If the thickness is less than 5 nm, it is difficult to form a light emitting layer, and it may be difficult to adjust the chromaticity. If the thickness exceeds 50 nm, the driving voltage may increase.

In the present invention, the light emitting layer preferably contains a fluorescent dopant. The fluorescent dopant is preferably a styrylamine compound or an arylamine compound.

The arylamine compound is more preferably a compound represented by the following formulas (2) to (4).

(Wherein R ^e is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, Substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted Aryloxy group having 6 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted ring formation An arylsilyl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkylgermanium group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl having 6 to 50 ring carbon atoms It is a germanium group.
t is an integer of 0 to 10.
Ar ³ to Ar ⁶ are each a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms. )

(Wherein R ^f represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, Substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted Aryloxy group having 6 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted ring formation An arylsilyl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkylgermanium group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl having 6 to 50 ring carbon atoms It is a germanium group.
u is an integer of 0-8.
Ar ⁷ to Ar ¹⁰ are each a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 20 ring atoms. )

In the formulas (2) to (4), examples of the substituted or unsubstituted alkyl group having 1 to 20 carbon atoms include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert- Examples thereof include butyl group, pentyl group, hexyl group, heptyl group, octyl group, stearyl group, 2-phenylisopropyl group, trichloromethyl group, trifluoromethyl group and the like, preferably methyl group, ethyl group, propyl group, tert- It is a butyl group.

Examples of the substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, and phenyl-t-butyl. Group, 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-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromine Benzyl group, m-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl 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, α-phenoxybenzyl group, α, α-dimethylbenzyl group, α, α-methylphenylbenzyl group, α, α-ditrifluoromethylbenzyl group, triphenylmethyl group, α-benzyloxybenzyl group, etc. That.

Examples of the substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms include, for example, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group, bicycloheptyl group, Bicyclooctyl group, tricycloheptyl group, adamantyl group and the like can be mentioned, and cyclopentyl group, cyclohexyl group, cycloheptyl group, bicycloheptyl group, bicyclooctyl group and adamantyl group are preferable.

The substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms is a group represented by —OZ, and Z is selected from the above substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

The substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms is represented by —OY, and Y is selected from the following substituted or unsubstituted aryl groups having 6 to 50 ring carbon atoms.

Examples of the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms include a phenyl group, a methylphenyl group, an ethylphenyl group, a biphenyl group, a cyclopentylphenyl group, a cyclohexylphenyl group, a methylbiphenyl group, an ethylbiphenyl group, Examples include cyclopentylphenyl group, cyclohexylbiphenyl group, terphenyl group, naphthyl group, methylnaphthyl group, anthryl group, pyrenyl group, chrysenyl group, fluoranthenyl group, perylenyl group, fluorenyl group, and the like, preferably phenyl group, naphthyl group , A fluorenyl group.
Examples of the substituted or unsubstituted heterocyclic group include heterocyclic groups similar to those exemplified for R _{11 in the} formula (1).

In the present invention, organic EL elements having a plurality of organic thin film layers are (anode / hole injection layer / light emitting layer / cathode), (anode / light emitting layer / electron injection layer / cathode), (anode / hole). (Injection layer / light emitting layer / electron injection layer / cathode) and the like.
In addition to the anthracene derivative of the present invention, the above-described fluorescent dopant and phosphorescent dopant, a known light emitting material, doping material, hole injection material, or electron injection material may be used for the multiple layers as necessary. You can also. The organic EL element can prevent the brightness | luminance and lifetime fall by quenching by making the said organic thin film layer into a multilayer structure. If necessary, a light-emitting material, a doping material, a hole injection material, and an electron injection material can be used in combination. Further, by using a doping material, it is possible to improve light emission luminance and light emission efficiency and to obtain red and blue light emission. Further, the hole injection layer, the light emitting layer, and the electron injection layer may each be formed of two or more layers. In that case, in the case of a hole injection layer, the layer that injects holes from the electrode is a hole injection layer, and the layer that receives holes from the hole injection layer and transports holes to the light emitting layer is a hole transport layer. Call. Similarly, in the case of an electron injection layer, a layer that injects electrons from an electrode is referred to as an electron injection layer, and a layer that receives electrons from the electron injection layer and transports electrons to a light emitting layer is referred to as an electron transport layer. Each of these layers is selected and used depending on factors such as the energy level of the material, heat resistance, adhesion with the organic layer or the metal electrode.

Examples of host materials or doping materials that can be used in the light emitting layer together with the anthracene derivative of the present invention include naphthalene, phenanthrene, rubrene, anthracene, anthracene derivatives, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, penta Condensed polycyclic aromatic compounds such as phenylcyclopentadiene, fluorene, spirofluorene, 9,10-diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis (9′-ethynylanthracenyl) benzene, and the like; Derivatives thereof, organometallic complexes such as tris (8-quinolinolato) aluminum, bis- (2-methyl-8-quinolinolato) -4- (phenylphenolinato) aluminum, triaryl Min derivative, styrylamine derivative, stilbene derivative, coumarin derivative, pyran derivative, oxazone derivative, benzothiazole derivative, benzoxazole derivative, benzimidazole derivative, pyrazine derivative, cinnamic acid ester derivative, diketopyrrolopyrrole derivative, acridone derivative, quinacridone Examples thereof include, but are not limited to, derivatives.

The hole injection layer and the hole transport layer help to inject holes into the light emitting layer and transport to the light emitting region, and have a high hole mobility and a small ionization energy of usually 5.5 eV or less. As a material for such a hole injection layer and a hole transport layer, a material that transports holes to the light emitting layer with lower electric field strength is preferable, and the hole mobility is, for example, 10 ⁴ to 10 ⁶ V / cm. When applying the electric field of 10 ⁻⁴ cm ² / V · sec or more, it is preferable.
The material for the hole injection layer and the hole transport layer is not particularly limited, and is conventionally used as a charge transport material for holes in optical transmission materials, and the hole injection layer and holes for organic EL devices. An arbitrary thing can be selected and used from the well-known things used for the transport layer.

For the hole injection layer and the hole transport layer, for example, an aromatic amine derivative represented by the following formula can be used.

Ar ²¹¹ to Ar ²¹³ , Ar ²²¹ to Ar ^223, and Ar ²⁰³ to Ar ²⁰⁸ are each a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted number of 5 to 50 nuclear atoms. An aromatic heterocyclic group. a to c and p to r are integers of 0 to 3, respectively. Ar ²⁰³ and Ar ²⁰⁴ , Ar ²⁰⁵ and Ar ²⁰⁶ , Ar ²⁰⁷ and Ar ²⁰⁸ may be connected to each other to form a saturated or unsaturated ring.

Furthermore, a compound represented by the following formula can be used for the hole injection layer and the hole transport layer.

Ar ²³¹ to Ar ²³⁴ are each a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms. L is a linking group, which is a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms. x is an integer of 0 to 5. Ar ²³² and Ar ²³³ may ^combine with each other to form a saturated or unsaturated ring. Specific examples of the substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms and the substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms are the same as those described above. can give.

Furthermore, specific examples of the material for the hole injection layer and the hole transport layer include, for example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives. And amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers (particularly thiophene oligomers).

The above materials can be used for the hole injection layer and the hole transport layer, but porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds, particularly aromatic tertiary amine compounds should be used. Is preferred.

Further, compounds having two condensed aromatic rings in the molecule, such as 4,4′-bis (N- (1-naphthyl) -N-phenylamino) biphenyl (hereinafter abbreviated as NPD), triphenylamine unit It is preferable to use 4,4 ′, 4 ″ -tris (N- (3-methylphenyl) -N-phenylamino) triphenylamine (hereinafter abbreviated as MTDATA) or the like in which three are connected in a starburst type. .

In addition, a nitrogen-containing heterocyclic derivative represented by the following formula can also be used.

In the formula, R ²⁰¹ to R ²⁰⁶ each represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic heterocyclic group. R ²⁰¹ and R ²⁰² , R ²⁰³ and R ²⁰⁴ , R ²⁰⁵ and R ²⁰⁶ , R ²⁰¹ and R ²⁰⁶ , R ²⁰² and R ²⁰³ , or R ²⁰⁴ and R ²⁰⁵ may form a condensed ring.

Furthermore, the compound of the following formula can also be used.

R ²¹¹ to R ²¹⁶ are substituents, each preferably an electron-withdrawing group such as a cyano group, a nitro group, a sulfonyl group, a carbonyl group, a trifluoromethyl group, or a halogen.

In addition, inorganic compounds such as p-type Si and p-type SiC can also be used as materials for the hole injection layer and the hole transport layer.
The hole injection layer and the hole transport layer can be formed by thinning the above-described compound by a known method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. The thickness of the hole injection layer and the hole transport layer is not particularly limited, but is usually 5 nm to 5 μm. The hole injection layer and the hole transport layer may be composed of one or more layers made of the above-mentioned materials, or a plurality of hole injection layers and hole transport layers made of different compounds are laminated. There may be.

As an electron injection material, it has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or light emitting material, and a hole injection layer of excitons generated in the light emitting layer The compound which prevents the movement to and is excellent in thin film forming ability is preferable.
As specific examples of the electron injecting material, 8-hydroxyquinoline or a metal complex of its derivative or an oxadiazole derivative is preferable. As a specific example of the metal complex of 8-hydroxyquinoline or its derivative, a metal chelate oxinoid compound containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline), such as tris (8-quinolinolato) aluminum, is injected. It can be used as a material.

On the other hand, examples of the oxadiazole derivative include electron transfer compounds represented by the following general formula.

(In the above formula, Ar ¹ , Ar ² , Ar ³ , Ar ⁵ , Ar ⁶ , and Ar ⁹ each represent a substituted or unsubstituted aryl group, and may be the same or different from each other.
Ar ⁴ , Ar ⁷ and Ar ⁸ represent a substituted or unsubstituted arylene group, and may be the same or different.

Further, materials represented by the following general formulas (A) to (F) can also be used as the electron injection material.

(In the general formulas (A) and (B), A ¹ to A ³ are each independently a nitrogen atom or a carbon atom.
Ar ¹ is a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 60 nuclear atoms,
Ar ² represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 60 nuclear atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. Or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms or a divalent group thereof.
However, any ^one of Ar ¹ and Ar ² is a substituted or unsubstituted condensed ring group having 10 to 60 nuclear carbon atoms, or a substituted or unsubstituted monoheterocondensed ring group having 5 to 60 nucleus atoms.
L ¹ , L ² and L are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 60 nuclear atoms, or a substituted or unsubstituted An unsubstituted fluorenylene group.
R represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 60 nuclear atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. Or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, n is an integer of 0 to 5, and when n is 2 or more, a plurality of R may be the same or different and adjacent to each other A plurality of R groups may be bonded to each other to form a carbocyclic aliphatic ring or a carbocyclic aromatic ring.
R ¹ represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 nuclear carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 nuclear carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. Or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms or —L ¹ —Ar ¹ —Ar ² . The nitrogen-containing heterocyclic derivative represented by this.

HAr-L-Ar ¹ -Ar ² (C)
(Wherein HAr is a nitrogen-containing heterocycle having 3 to 40 carbon atoms which may have a substituent,
L has a single bond, an arylene group having 6 to 60 nuclear carbon atoms which may have a substituent, a heteroarylene group having 5 to 60 nuclear atoms which may have a substituent, or a substituent. A fluorenylene group which may be
Ar ¹ is an optionally substituted divalent aromatic hydrocarbon group having 6 to 60 nuclear carbon atoms,
Ar ² is an aryl group having 6 to 60 nuclear carbon atoms which may have a substituent or a heterocyclic group having 5 to 60 nuclear atoms which may have a substituent. The nitrogen-containing heterocyclic derivative represented by this.

Wherein X and Y are each independently a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, an alkoxy group, an alkenyloxy group, an alkynyloxy group, a hydroxy group, a substituted or unsubstituted aryl group, a substituted group Or an unsubstituted heterocyclic ring or a structure in which X and Y are combined to form a saturated or unsaturated ring,
R ₁ to R ₄ each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an alkoxy group, an aryloxy group, a perfluoroalkyl group, a perfluoroalkoxy group, an amino group, Alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, azo group, alkylcarbonyloxy group, arylcarbonyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, sulfinyl group, sulfonyl group, sulfanyl group, Silyl, carbamoyl, aryl, heterocyclic, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate, isocyanate, thiocyanate, isothi If the cyanate were group or cyano group, or adjacent a structure substituted or the unsubstituted rings are fused. A silacyclopentadiene derivative represented by:

(Wherein R ₁ to R ₈ and Z ₂ are each independently a hydrogen atom, a saturated or unsaturated hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, a substituted amino group, a substituted boryl group, or an alkoxy group. Or an aryloxy group,
X, Y and Z ₁ each independently represent a saturated or unsaturated hydrocarbon group, aromatic hydrocarbon group, heterocyclic group, substituted amino group, alkoxy group or aryloxy group;
The substituents of Z ₁ and Z ₂ may be bonded to each other to form a condensed ring. N represents an integer of 1 to 3, and when n is 2 or more, Z ₁ may be different.
However, the case where n is 1, X, Y and R ₂ are methyl groups and R ₈ is a hydrogen atom or a substituted boryl group and the case where n is 3 and Z ₁ is a methyl group are not included. A borane derivative represented by:

[Wherein, Q ¹ and Q ² each independently represent a ligand represented by the following general formula (G),
L is a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, —OR ¹ (R ¹ is a hydrogen atom, A substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group) or —O—Ga—Q ³ (Q ⁴ ) (Q ³ and Q ⁴ are the same as Q ¹ and Q ² ). ]

[Wherein, rings A ¹ and A ² are 6-membered aryl ring structures condensed with each other which may have a substituent. ]

This metal complex has strong properties as an n-type semiconductor and has a large electron injection capability. Furthermore, since the generation energy at the time of complex formation is also low, the bond between the metal of the formed metal complex and the ligand is strengthened, and the fluorescence quantum efficiency as a light emitting material is also increased.
The alkyl group, aromatic hydrocarbon group, aryl group, heterocyclic group, condensed aromatic group and the like described in the above-described dopant hole injecting material, hole transporting material, and electron injecting material in the present invention are represented by the above formula (1). The examples given above for R ₁ to R ₂₂ can be applied.

Favorable forms of the organic EL device of the present invention include a device containing a reducing dopant in an electron transporting region or an interface region between a cathode and an organic layer. Here, the reducing dopant is defined as a substance capable of reducing the electron transporting compound. Accordingly, various materials can be used as long as they have a certain reducibility, such as alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metals. Oxides, alkaline earth metal halides, rare earth metal oxides or rare earth metal halides, alkali metal carbonates, alkaline earth metal carbonates, alkali metal organic complexes, alkaline earth metal organic complexes In addition, at least one substance selected from the group consisting of organic complexes of rare earth metals can be preferably used.

More specifically, preferable reducing dopants include Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV) and Cs (work function: 1 .95 eV), at least one alkali metal selected from the group consisting of Ca (work function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV), and Ba (work function: 2.52 eV). Particularly preferred are those having a work function of 2.9 eV or less, including at least one alkaline earth metal selected from the group consisting of: Among these, a more preferable reducing dopant is at least one alkali metal selected from the group consisting of K, Rb, and Cs, more preferably Rb or Cs, and most preferably Cs. . These alkali metals have particularly high reducing ability, and the addition of a relatively small amount to the electron injection region can improve the light emission luminance and extend the life of the organic EL element. Further, as a reducing dopant having a work function of 2.9 eV or less, a combination of two or more alkali metals is also preferable. Particularly, a combination containing Cs, such as Cs and Na, Cs and K, Cs and Rb, or Cs. And a combination of Na and K. By including Cs in combination, the reducing ability can be efficiently exhibited, and by adding to the electron injection region, the emission luminance and the life of the organic EL element can be improved.

In the present invention, an electron injection layer composed of an insulator or a semiconductor may be further provided between the cathode and the organic layer. At this time, current leakage can be effectively prevented and the electron injection property can be improved. As such an insulator, it is preferable to use at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides. If the electron injection layer is composed of these alkali metal chalcogenides or the like, it is preferable in that the electron injection property can be further improved.
Specifically, preferable alkali metal chalcogenides include, for example, Li ₂ O, K ₂ O, Na ₂ S, Na ₂ Se, and Na ₂ O, and preferable alkaline earth metal chalcogenides include, for example, CaO, BaO. , SrO, BeO, BaS, and CaSe. Further, preferable alkali metal halides include, for example, LiF, NaF, KF, CsF, LiCl, KCl, and NaCl. Examples of preferable alkaline earth metal halides include fluorides such as CaF ₂ , BaF ₂ , SrF ₂ , MgF ₂ and BeF ₂ , and halides other than fluorides.

In addition, as a semiconductor constituting the electron injection layer, an oxide containing at least one element of Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb, and Zn. , Nitrides or oxynitrides, or a combination of two or more. In addition, the inorganic compound constituting the electron injection layer is preferably a microcrystalline or amorphous insulating thin film. If the electron injection layer is composed of these insulating thin films, a more uniform thin film is formed, and pixel defects such as dark spots can be reduced. Examples of such inorganic compounds include the alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides described above.

Next, as a cathode, what uses a metal, an alloy, an electroconductive compound, and a mixture thereof with a small work function (4 eV or less) as an electrode material is used. Specific examples of such electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, cesium, magnesium / silver alloy, aluminum / aluminum oxide, Al / Li ₂ O, Al / LiO, Al / LiF, aluminum Examples include lithium alloys, indium, and rare earth metals.
This cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.

Here, when light emitted from the light emitting layer is taken out from the cathode, it is preferable that the transmittance of the light emitted from the cathode is larger than 10%. The sheet resistance as the cathode is preferably several hundred Ω / □ or less, and the film thickness is usually 10 nm to 1 μm, preferably 50 to 200 nm.

In general, since an organic EL element applies an electric field to an ultra-thin film, pixel defects are likely to occur due to leakage or short circuit. In order to prevent this, an insulating thin film layer may be inserted between the pair of electrodes.

Examples of the material used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, and silicon oxide. Germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, and the like. A mixture or laminate of these may be used.

In order to improve the stability of the organic EL device obtained by the present invention against temperature, humidity, atmosphere, etc., it is possible to provide a protective layer on the surface of the device, or to protect the entire device with silicon oil, resin, etc. It is.

As the conductive material used for the anode of the organic EL device of the present invention, a material having a work function larger than 4 eV is suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum Palladium, etc. and their alloys, metal oxides such as tin oxide and indium oxide used for ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole are used. Suitable conductive materials for the cathode are those having a work function smaller than 4 eV, such as magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride, and the like. However, it is not limited to these. Examples of alloys include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but are not limited thereto. The ratio of the alloy is controlled by the temperature of the vapor deposition source, the atmosphere, the degree of vacuum, etc., and is selected to an appropriate ratio. If necessary, the anode and the cathode may be formed of two or more layers.

In the organic EL device of the present invention, in order to emit light efficiently, it is desirable that at least one surface is sufficiently transparent in the light emission wavelength region of the device. The substrate is also preferably transparent. The transparent electrode is set using the above-described conductive material so as to ensure a predetermined translucency by a method such as vapor deposition or sputtering. The electrode on the light emitting surface preferably has a light transmittance of 10% or more. The substrate is not limited as long as it has mechanical and thermal strength and has transparency, and includes a glass substrate and a transparent resin film.
Transparent resin films include polyethylene, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, polypropylene, polystyrene, polymethyl methacrylate, polyvinyl chloride, polyvinyl alcohol, polyvinyl butyral, nylon, polyether ether ketone. , Polysulfone, polyethersulfone, tetrafluoroethylene-perfluoroalkyl vinyl ether copolymer, polyvinyl fluoride, tetrafluoroethylene-ethylene copolymer, tetrafluoroethylene-hexafluoropropylene copolymer, polychlorotrifluoroethylene, Polyvinylidene fluoride, polyester, polycarbonate, polyurethane, polyimide, polyetherimide, polyimide, polypropylene, etc. It is.

For the formation of each layer of the organic EL device according to the present invention, any of dry film forming methods such as vacuum deposition, sputtering, plasma, ion plating, etc. and wet film forming methods such as spin coating, dipping, and flow coating is applied. be able to. The film thickness is not particularly limited, but must be set to an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too thin, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied. The normal film thickness is suitably in the range of 5 nm to 10 μm, but more preferably in the range of 10 nm to 0.2 μm.

In the case of the wet film-forming method, the material for forming each layer is dissolved or dispersed in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane or the like to form a thin film, and any solvent may be used. In any organic thin film layer, an appropriate resin or additive may be used for improving film formability and preventing pinholes in the film. Usable resins include polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, cellulose and other insulating resins and copolymers thereof, poly-N-vinyl. Examples thereof include photoconductive resins such as carbazole and polysilane, and conductive resins such as polythiophene and polypyrrole. Examples of the additive include an antioxidant, an ultraviolet absorber, and a plasticizer.

The organic EL device of the present invention can be used for a flat light emitter such as a flat panel display of a wall-mounted television, a light source such as a copying machine, a printer, a backlight of a liquid crystal display or instruments, a display board, a marker lamp, and the like. The material of the present invention can be used not only in an organic EL device but also in fields such as an electrophotographic photosensitive member, a photoelectric conversion device, a solar cell, and an image sensor.
[Example]

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

Example 1
Compound 1 was synthesized according to the following synthesis scheme.

[Synthesis of 2-phenylanthracene]
In an argon atmosphere, 14.5 g of phenylboronic acid, 25.7 g of 2-bromoanthracene, 2.31 g of tetrakis (triphenylphosphine) palladium (0), 400 mL of toluene, and 200 mL of 2M sodium carbonate aqueous solution were charged and stirred at reflux for 8 hours. did. After stirring, the mixture was cooled to room temperature, and the precipitated crystals were filtered off. The obtained crystals were recrystallized from toluene-hexane and washed repeatedly to obtain 19.1 g of 2-phenylanthracene (yield 75%).

[Synthesis of 9,10-dibromo-2-phenylanthracene]
19.1 g of the synthesized 2-phenylanthracene was dissolved in 200 mL of N, N-dimethylformamide with heating, 29.4 g of N-bromosuccinimide in 20 mL of N, N-dimethylformamide was added, and the mixture was stirred with heating at 60 ° C. for 6 hours. After stirring, the mixture was cooled to room temperature, and the reaction solution was poured into 1 L of water. The obtained solid was washed successively with methanol, water and methanol, recrystallized with toluene-hexane, and washed repeatedly to obtain 24.8 g (yield 80%) of 9,10-dibromo-2-phenylanthracene.

[Synthesis of Compound 1]
Under an argon atmosphere, 2.06 g of 9,10-dibromo-2-phenylanthracene synthesized, 2.98 g of 4- (2-naphthyl) phenylboronic acid synthesized by a known method, tetrakis (triphenylphosphine) palladium (0) 0.231 g, 40 mL of toluene, and 20 mL of 2M aqueous sodium carbonate solution were added, and the mixture was stirred at reflux for 8 hours. After stirring, the mixture was cooled to room temperature, and the precipitated crystals were filtered off. The obtained crystals were washed with methanol, water, and methanol, and then recrystallized with toluene to obtain pale yellow crystals.
The obtained compound 1 had a molecular weight of 658.27 and m / e = 658.

Example 2
Compound 2 was synthesized according to the following synthesis scheme.

[Synthesis of Compound 2]
Compound 2 was synthesized and identified in the same manner as in Example 1 except that 3- (1-naphthyl) phenylboronic acid synthesized by a known method was used instead of 4- (1-naphthyl) phenylboronic acid.
The obtained compound 2 had a molecular weight of 658.27 and m / e = 658.

Example 3
Compound 3 was synthesized according to the following synthesis scheme.

[Synthesis of Compound 3]
Compound 3 was synthesized and identified in the same manner as in Example 1 except that 3- (2-naphthyl) phenylboronic acid synthesized by a known method was used instead of 4- (1-naphthyl) phenylboronic acid.
The obtained compound 3 had a molecular weight of 658.27 and m / e = 658.

Example 4
Compound 4 was synthesized according to the following synthesis scheme.

[Synthesis of 2- (2-naphthyl) anthracene]
2- (2-naphthyl) anthracene was synthesized in the same manner as the synthesis of 2-phenylanthracene in Example 1 except that 2-naphthaleneboronic acid was used instead of phenylboronic acid.

[Synthesis of 9,10-dibromo-2- (2-naphthyl) anthracene]
9,10-dibromo-2 was synthesized in the same manner as the synthesis of 9,10-dibromo-2-phenylanthracene of Example 1 except that 2- (2-naphthyl) anthracene synthesized instead of 2-phenylanthracene was used. -(2-Naphthyl) anthracene was synthesized.

[Synthesis of Compound 4]
Compound 4 was synthesized in the same manner as Compound 1 of Example 1 except that 9,10-dibromo-2- (2-naphthyl) anthracene was used instead of 9,10-dibromo-2-phenylanthracene. Identified.
The obtained compound 4 had a molecular weight of 708.28 and m / e = 708.

Example 5
Compound 5 was synthesized according to the following synthesis scheme.

Instead of 9,10-dibromo-2-phenylanthracene, 9,10-dibromo-2- (2-naphthyl) anthracene was synthesized by a known method instead of 4- (1-naphthyl) phenylboronic acid. Compound 5 was synthesized and identified in the same manner as in Example 1 except that (2-naphthyl) phenylboronic acid was used.
The molecular weight of Compound 5 obtained was 708.28, and m / e = 708.

Example 6
Compound 6 was synthesized according to the following synthesis scheme.

9,10-Dibromo-2- (2-naphthyl) anthracene instead of 9,10-dibromo-2-phenylanthracene was synthesized by a known method instead of 4- (1-naphthyl) phenylboronic acid. Compound 6 was synthesized and identified in the same manner as in Example 1 except that (1-naphthyl) phenylboronic acid was used.
The obtained compound 6 had a molecular weight of 708.28 and m / e = 708.

Example 7
Compound 7 was synthesized according to the following synthesis scheme.

Instead of 9,10-dibromo-2-phenylanthracene, 9,10-dibromo-2- (2-naphthyl) anthracene was synthesized by a known method instead of 4- (1-naphthyl) phenylboronic acid. The compound was synthesized and identified in the same manner as in Example 1 except that (2-naphthyl) phenylboronic acid was used.
The molecular weight of Compound 7 obtained was 708.28, and m / e = 708.

Example 8
Compound 8 was synthesized according to the following synthesis scheme.

[Synthesis of 2-bromodibenzofuran]
150 g of dibenzofuran and 1 L of acetic acid were charged into a flask and purged with nitrogen and dissolved by heating. After adding 188 g of bromine dropwise with occasional water cooling, the mixture was stirred for 20 hours under air cooling. The precipitated crystals were separated by filtration, washed successively with acetic acid and water, and dried under reduced pressure. The obtained crystals were purified by distillation under reduced pressure and then recrystallized several times with methanol to obtain 66.8 g (yield 31%) of 2-bromodibenzofuran.

[Synthesis of dibenzofuran-2-boronic acid]
Under an argon atmosphere, 400 mL of anhydrous THF was added to 24.7 g of 2-bromodibenzofuran, and 63 mL of a 1.6M n-butyllithium hexane solution was added with stirring at −40 ° C. The reaction solution was stirred for 1 hour while warming to 0 ° C. The reaction solution was cooled again to −78 ° C., and a solution of trimethyl borate (26.0 g) in dry THF (50 mL) was added dropwise. The reaction solution was stirred at room temperature for 5 hours. After adding 200 mL of 1N hydrochloric acid and stirring for 1 hour, the aqueous layer was removed. The organic layer was dried over magnesium sulfate and the solvent was removed under reduced pressure. The obtained solid was washed with toluene to obtain 15.2 g (yield 72%) of dibenzofuran-2-boronic acid.

[Synthesis of 2- (2-dibenzofuranyl) anthracene]
2- (2-Dibenzofuranyl) anthracene was synthesized in the same manner as the synthesis of 2-phenylanthracene in Example 1, except that dibenzofuran-2-boronic acid was used instead of phenylboronic acid.

[Synthesis of 2- (2-dibenzofuranyl) -9,10-dibromoanthracene]
2- (2-Dibenzofuranyl) was synthesized in the same manner as the synthesis of 9,10-dibromo-2-phenylanthracene in Example 1, except that 2- (2-dibenzofuranyl) anthracene was used instead of 2-phenylanthracene. ) -9,10-Dibromoanthracene was synthesized.

[Synthesis of Compound 8]
2- (2-Dibenzofuranyl) -9,10-dibromoanthracene prepared in place of 9,10-dibromo-2-phenylanthracene was prepared in place of 4- (1-naphthyl) phenylboronic acid Compound 8 was synthesized and identified in the same manner as in Example 1 except that (1-naphthyl) phenylboronic acid was used.
The obtained compound 8 had a molecular weight of 748.28 and m / e = 748.

Example 9
Compound 9 was synthesized according to the following synthesis scheme.

The compound 1 was synthesized in the same manner using 3- (2-dibenzofuranyl) phenylboronic acid synthesized by a known method instead of 4- (1-naphthyl) phenylboronic acid. As a result of mass spectrum analysis, it was confirmed that the obtained crystal was Compound 10. The molecular weight of Compound 9 obtained was 738.26, and m / e = 738.

Example 10
Compound 10 was synthesized according to the following synthesis scheme.

In the synthesis of Compound 1, 3- (2-naphthyl) phenylboronic acid synthesized by a known method instead of 4- (1-naphthyl) phenylboronic acid was synthesized by a known method instead of phenylboronic acid. , 9-Dimethylfluorene-2-boronic acid was synthesized in the same manner. As a result of mass spectrum analysis, it was confirmed that the obtained crystal was Compound 11. The obtained compound 11 had a molecular weight of 774.33 and m / e = 774.

Example 11
[Production of organic EL element]
A 25 mm × 75 mm × 1.1 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes. The cleaned glass substrate with a transparent electrode line is mounted on a substrate holder of a vacuum deposition apparatus, and first, a compound A-1 having a film thickness of 60 nm is formed so as to cover the transparent electrode on the surface on which the transparent electrode line is formed. Was deposited. Subsequent to the formation of the A-1 film, A-2 having a thickness of 20 nm was formed on the A-1 film. Further, a compound 1 (host material) synthesized in Example 1 and a dopant material D-1 were formed in a film thickness ratio of 40: 2 on the A-2 film at a film thickness of 40 nm to form a light emitting layer.

On this film, the compound ET-1 was deposited as an electron transport layer with a thickness of 20 nm by vapor deposition. Thereafter, LiF was formed to a thickness of 1 nm. On the LiF film, metal Al was deposited to a thickness of 150 nm to form a metal cathode, thereby forming an organic EL device. When voltage was applied to this organic EL element, blue light emission was obtained.

Examples 12 to 125 and Comparative Examples 1 to 30
In Example 11, organic EL devices were similarly produced using the host materials and dopant materials shown in Tables 1 to 4 instead of the host material compound 1 and the dopant material D-1.

Tables 1 to 4 show the light emission efficiency, the half-life at an initial luminance of 1000 cd / m ^2, and the light emission color of the organic EL devices obtained in Examples 11 to 125 and Comparative Examples 1 to 30, respectively.
From the results in Tables 1 to 4, it was found that the organic EL device using the anthracene derivative of the present invention has excellent light emission characteristics.

The energy gap and emission wavelength of Compound 2, Compound (A), Compound (B), and Compound (C) used for the production of the organic EL device were evaluated. The results are shown in Table 5.

As can be seen from Table 5, Compound 2, which is an anthracene derivative of the present invention, has an energy gap smaller than that of Compound (A) and exhibits an emission wavelength close to that of Compound (A).
Therefore, it is presumed that Compound 2 can emit light with smaller energy and can extend the lifetime of the organic EL device.

The compound (B) and the compound (C) also have a small energy gap like the compound 2. However, since these compounds have a longer emission wavelength than the compound 2, energy transfer to the blue dopant is difficult, and the blue element It is estimated that the light emission efficiency decreases.

Since the anthracene derivative of the present invention has an appropriate energy gap and emission wavelength even in the green color, as can be seen from the organic EL devices of Examples 26 to 125, the anthracene derivative of the present invention is highly efficient. A long-life green element is obtained.

The organic EL element using the organic light emitting medium of the present invention is useful as a light source such as a flat light emitter of a wall-mounted television or a backlight of a display.
The entire contents of the documents described in this specification are incorporated herein by reference.

Claims

Anthracene derivatives represented by the following formula (1) (excluding those represented by the following formula (1 ′)).

Wherein R 1 to R 7 are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted carbon, An alkoxy group of 1 to 50, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group.
R 11 to R 15 and R 21 to R 25 are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted group An alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted condensed aromatic group having 10 to 50 carbon atoms, a substituted or unsubstituted number of nuclear atoms It is a 5-50 heterocyclic group, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group.
Provided that at least one of R 11 to R 15 and R 21 to R 25 is a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 nuclear atoms. It is a group.
Ar 1 is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms.
However, Ar 1 does not include an orthophenylene structure. )
Any one of R 11 to R 15 is a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms,
Substituted or unsubstituted fused aromatic group having 10 to 50 carbon atoms, or all of R 11 ~ R 15 other than R 11 ~ R 15 is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms is A hydrogen atom,
Any one of R 21 to R 25 is a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms,
Substituted or unsubstituted fused aromatic group having 10 to 50 carbon atoms, or all of R 21 ~ R 25 other than R 21 ~ R 25 is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms is The anthracene derivative according to claim 1, which is a hydrogen atom.
R 12 and R 22 are each a substituted or unsubstituted condensed aromatic ring group having 10 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, and R 11 , R 13 , The anthracene derivative according to claim 1, wherein R 14 , R 15 , R 21 , R 23 , R 24 and R 25 are hydrogen atoms.
R 13 and R 23 are each a substituted or unsubstituted condensed aromatic ring group having 10 to 50 nuclear carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 nucleus atoms, and R 11 , R 12 , The anthracene derivative according to claim 1, wherein R 14 , R 15 , R 21 , R 22 , R 24 and R 25 are hydrogen atoms.
Ar 1 is an unsubstituted phenyl group, a fluorenyl group having a substituent at the 9-position, an unsubstituted condensed aromatic group having 10 to 20 nuclear carbon atoms, or an unsubstituted heterocyclic group having 5 to 20 nuclear atoms. The anthracene derivative according to any one of claims 1 to 4.
The anthracene derivative according to any one of claims 1 to 5, wherein the condensed aromatic group of Ar 1 is a naphthyl group, a phenanthryl group, a pyrenyl group, or a fluoranthenyl group.
7. The anthracene derivative according to claim 1, wherein R 1 to R 7 are hydrogen atoms.
A material for an organic electroluminescence device comprising the anthracene derivative according to any one of claims 1 to 7.
The material for an organic electroluminescence element according to claim 8, which is a light emitting material.
An anode and a cathode;
Having one or more organic thin film layers including a light emitting layer sandwiched between the anode and the cathode;
The organic electroluminescent element in which at least 1 layer of the said organic thin film layer contains the organic electroluminescent element material of Claim 8.
The organic electroluminescence device according to claim 10, wherein the light emitting layer contains the material for an organic electroluminescence device.
The organic electroluminescent element according to claim 11, wherein the organic electroluminescent element material is a host material.
An anode and a cathode;
Having one or more organic thin film layers including a light emitting layer sandwiched between the anode and the cathode;
The light emitting layer contains an anthracene derivative represented by the following formula (1) as a host material,
Furthermore, the organic electroluminescent element containing at least one of a fluorescent dopant and a phosphorescent dopant.

Wherein R 1 to R 7 are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted carbon, An alkoxy group of 1 to 50, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group.
R 11 to R 15 and R 21 to R 25 are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted group An alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted condensed aromatic group having 10 to 50 carbon atoms, a substituted or unsubstituted number of nuclear atoms It is a 5-50 heterocyclic group, a substituted or unsubstituted silyl group, a halogen atom, or a cyano group.
Provided that at least one of R 11 to R 15 and R 21 to R 25 is a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 nuclear atoms. It is a group.
Ar 1 is a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms.
However, Ar 1 does not include an orthophenylene structure. )
The organic electroluminescent device according to claim 13, wherein the fluorescent dopant is a styrylamine compound.
The organic electroluminescence device according to claim 13, wherein the fluorescent dopant is an arylamine compound.
The organic electroluminescence device according to claim 15, wherein the arylamine compound is a compound represented by the following formula (2).

(Wherein R e is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, Substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted Aryloxy group having 6 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted ring formation An arylsilyl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkylgermanium group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl having 6 to 50 ring carbon atoms It is a germanium group.
t is an integer of 0 to 10.
Ar 3 to Ar 6 are each a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms. )
The organic electroluminescence device according to claim 15, wherein the arylamine compound is a compound represented by the following formula (3).

(Wherein R f represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, Substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted Aryloxy group having 6 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted ring formation An arylsilyl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkylgermanium group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl having 6 to 50 ring carbon atoms It is a germanium group.
u is an integer of 0-8.
Ar 7 to Ar 10 are each a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 20 ring atoms. )
The organic electroluminescence device according to claim 15, wherein the arylamine compound is a compound represented by the following formula (4).

(Wherein R g is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, Substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted Aryloxy group having 6 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted ring formation An arylsilyl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkylgermanium group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl having 6 to 50 ring carbon atoms It is a germanium group.
q is an integer of 0-6.
R 30 and R 31 are each a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 20 nuclear atoms.
Ar 11 to Ar 14 are each a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 20 ring atoms. )