WO2013175746A1

WO2013175746A1 - Organic electroluminescent element

Info

Publication number: WO2013175746A1
Application number: PCT/JP2013/003147
Authority: WO
Inventors: 池田　剛; 裕勝伊藤
Original assignee: 出光興産株式会社
Priority date: 2012-05-22
Filing date: 2013-05-17
Publication date: 2013-11-28
Also published as: TW201410840A

Abstract

An organic electroluminescent element wherein between an opposing anode and cathode there is at least an organic light emission layer and an electron transport layer that are adjacent in this order from the anode side, the organic light emission layer includes an anthracene compound represented by formula (1-1), and the electron transport layer includes an azine compound represented by formula (2-1). Ar¹¹-Az (2-1)

Description

Organic electroluminescence device

The present invention relates to an organic electroluminescence element.

An organic electroluminescence (EL) element is a self-luminous element utilizing the principle that a light-emitting material emits light by recombination energy of holes injected from an anode and electrons injected from a cathode when an electric field is applied.
Organic EL elements have features such as low voltage drive, high brightness, diversity of emission wavelengths, high-speed response, and the ability to produce thin and light-emitting devices, and are therefore applied to a wide range of applications.
Organic compound materials used in organic EL elements have been actively studied since they have a great influence on the color of light emitted from the elements and the light emission lifetime. For example, Patent Document 1 discloses an anthracene compound with a four-ring condensed ring.

Although development of materials for organic EL elements has been studied, further improvement in the lifetime of organic EL elements and further improvement in luminous efficiency are required.

International publication WO2011 / 054442

An object of the present invention is to provide an organic EL element with improved lifetime and luminous efficiency.

When the organic light emitting layer containing a specific anthracene compound and the electron transport layer containing a specific azine compound are formed adjacent to each other, the present inventors have a long lifetime and high light emission efficiency. The inventors found that an element can be obtained and completed the present invention.

According to the present invention, the following organic EL elements and the like are provided.
1. Between the anode and cathode facing each other, from the anode side, at least an organic light emitting layer and an electron transport layer are adjacent to each other in this order,
The organic light emitting layer contains an anthracene compound represented by the following formula (1-1):
The electron transport layer contains an azine compound represented by the following formula (2-1):
Organic electroluminescence device.

(In the formula (1-1), Ar ¹ is a substituted or unsubstituted aromatic hydrocarbon group having 15 to 60 ring carbon atoms.
Ar ² is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
L is a single bond or a substituted or unsubstituted arylene group having 6 to 10 ring carbon atoms.
R ¹ to R ⁸ are each independently a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted An unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or a substituted or unsubstituted ring An arylsilyl group having 8 to 50 carbon atoms formed.
n is an integer of 1 to 4, and when n is 2 or more, the plurality of L may be the same or different. )

(In Formula (2-1),
Ar ¹¹ is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms having at least one substituted or unsubstituted carbazole skeleton-containing group as a substituent.
Az is a substituted or unsubstituted aromatic nitrogen-containing 6-membered cyclic group. )
2. 2. The organic electroluminescence device according to 1, wherein the azine compound represented by the formula (2-1) has a substituted or unsubstituted carbazole skeleton-containing group which is a substituted or unsubstituted 9-carbazolyl group.
3. 2. The organic electroluminescence device according to 1, wherein Ar ^{11 in the} formula (2-1) is selected from any of the following.

(Wherein L ¹⁰⁰ is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
Ar ¹⁰⁰ is a hydrogen atom or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms. )
4). 3. The organic electroluminescence device according to 1 or 2, wherein the azine compound is a compound represented by the following formula (2-1).

(In the formula (2-2), k is an integer of 1 to 3, n is an integer of 0 to 3,
R ¹¹ to R ¹⁸ are each independently a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 ring atoms. Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 ring carbon atoms, substituted or unsubstituted An aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted 3 to 30 carbon atoms An alkylsilyl group, a substituted or unsubstituted dialkylarylsilyl group having 8 to 40 carbon atoms, a substituted or unsubstituted alkyldiarylsilyl group having 13 to 50 carbon atoms, a substituted Or an unsubstituted triarylsilyl group having 18 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a halogen atom, a cyano group, A hydroxyl group, a nitro group, or a carboxy group.
Az is a substituted or unsubstituted aromatic nitrogen-containing 6-membered cyclic group. )
5. 5. The organic electroluminescence device according to 4, wherein Az in the formula (2-2) is a group represented by the following formula (2a).

(In Formula (2a), X ¹ to X ³ are each independently a nitrogen atom or CH, and at least two of X ¹ to X ³ are nitrogen atoms.
Ar ¹² and Ar ¹³ are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms. )
6). 6. The organic electroluminescence device according to 5, wherein X ¹ and X ^{2 in} the formula (2a) are nitrogen atoms and X ³ is CH.
7). Formula number of carbon atoms of ^{Ar 12} in (2a) is equal to or less than the number of carbon atoms of ^{Ar 13,} the organic electroluminescence device according to 5 or 6.
8). 8. The organic electroluminescence device according to any one of 5 to 7, wherein Ar ^{12 in the} formula (2a) is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted biphenyl group. .
9. 9. The organic electroluminescence device according to any one of 4 to 8, wherein k in the formula (2-2) is 2.
10. 10. The organic electroluminescence device according to any one of 4 to 9, wherein R ¹¹ to R ^{18 in} the formula (2-2) are hydrogen atoms.
11. Ar ^{1 in the} formula (1-1) is a substituent represented by the following formula (1a), (1b), (1c), (1d), (1e), (1f), (1g) or (1h) The organic electroluminescence device according to any one of 1 to 10, which is any one of

(In formulas (1a) to (1h), one of R is a single bond bonded to L, and each R other than a single bond is independently a hydrogen atom, a fluorine atom, a cyano group, substituted or unsubstituted. An alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted ring forming carbon atom having 6 to 6 carbon atoms. 30 aryloxy groups, substituted or unsubstituted trialkylsilyl groups having 3 to 40 carbon atoms, or substituted or unsubstituted arylsilyl groups having 8 to 50 carbon atoms.)
12 The organic electro according to any one of 1 to 11, wherein Ar ^{1 in the} formula (1-1) is any one of substituents represented by the following formulas (1a), (1b), (1c) or (1h): Luminescence element.

(In the formulas (1a) to (1c) and (1h), one of R is a single bond bonded to L, and each R other than a single bond is independently a hydrogen atom, a fluorine atom, a cyano group, Substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted ring formation A C6-C30 aryloxy group, a substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or a substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms.)
13. The organic compound according to W described in any one of 1 to 12, wherein Ar ^{1 in the} formula (1-1) is any one of substituents represented by the following formula (1a ′), (1b ′), or (1h ′) Electroluminescence element.

(In the formulas (1a ′), (1b ′) and (1h ′), any one of R ′ is a single bond bonded to L, and R ′ and R other than a single bond are each independently hydrogen. Atom, fluorine atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or a substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms is there.)
14 14. The organic electroluminescence device according to any one of 1 to 13, wherein L in the formula (1-1) is a single bond.
15. A panel module using the organic electroluminescence device according to any one of 1 to 14.
Electronic equipment using the panel module according to 16.15.

According to the present invention, it is possible to provide an organic EL element with improved lifetime and luminous efficiency.

It is the schematic which shows the layer structure of the organic EL element of one Embodiment of this invention. It is a schematic sectional drawing which shows the example of the organic electroluminescent light-emitting device using the organic electroluminescent element of this invention. It is the schematic which shows the layer structure of the organic EL element of other embodiment of this invention.

The organic EL device of the present invention has an organic light emitting layer and an electron transport layer adjacent to each other in this order between at least the anode side and the anode, and the organic light emitting layer has the following formula (1-1): And the electron transport layer contains an azine compound represented by the following formula (2-1). In the present invention, azine is a 6-membered ring compound containing one or more nitrogen atoms in the ring.

(In the formula (1-1), Ar ¹ is a substituted or unsubstituted aromatic hydrocarbon group having 15 to 60 ring carbon atoms.
Ar ² is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
L is a single bond or a substituted or unsubstituted arylene group having 6 to 10 ring carbon atoms.
R ¹ to R ⁸ are each independently a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted Unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or substituted or unsubstituted And an arylsilyl group having 8 to 50 carbon atoms.
n is an integer of 1 to 4, and when n is 2 or more, the plurality of L may be the same or different. )

(In Formula (2-1),
Ar ¹¹ is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms having at least one substituted or unsubstituted carbazole skeleton-containing group as a substituent.
Az is a substituted or unsubstituted aromatic nitrogen-containing 6-membered cyclic group. )

In the organic EL device of the present invention, a laminate comprising an organic light emitting layer containing an anthracene compound represented by formula (1-1) and an electron transport layer containing an azine compound represented by formula (2-1) is adjacent to each other. Including. The azine compound represented by the formula (2-1) is estimated to be able to smoothly inject electrons into the organic light emitting layer, and enables the device to be driven at a low voltage. Further, the charge balance can be optimized by including the anthracene compound represented by the formula (1-1) in the organic light emitting layer for smooth electron injection by the azine compound of the electron transport layer. Thereby, the organic EL element of this invention can show high efficiency and long lifetime.

[Anthracene compounds]
The anthracene compound contained in the organic light-emitting layer is preferably such that Ar ^{1 in the} formula (1-1) has the following formulas (1a), (1b), (1c), (1d), (1e), (1f), (1g ) Or (1h), and more preferably any of the substituents represented by formula (1a), (1b), or (1h).
Preferably, Ar ¹ is any one of the groups represented by the following formulas (1a), (1b), (1c), (1d), (1e), (1f), (1g) or (1h). And more preferably a substituent containing any of the groups represented by the formula (1a), (1b), or (1h). The substituent containing a group represented by the formula (1a) or the like is preferably a group in which a group represented by the formula (1a) or the like is bonded to phenylene, naphthalenylene, biphenylene or the like.
Generally, increasing the size of the condensed ring in the molecule increases the overlap between molecules and improves transportability. However, if the condensed ring is too large, the carrier balance may be lost and efficiency may not be obtained.

(In formulas (1a) to (1h), one of R is a single bond bonded to L, and each R other than a single bond is independently a hydrogen atom, a fluorine atom, a cyano group, substituted or unsubstituted. An alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted 6 to 30 carbon atoms. An aryloxy group, a substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or a substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms.)

When Ar ^{1 in} formula (1-1) is a substituent represented by formula (1a), (1b) or (1h), the position of substitution of these substituents with L is represented by the following formula (1a ′), A relationship of (1b ′) or (1h ′) is preferable. Since the portion corresponding to the substitution position is considered to be an active site in the ring structure, it is considered that the substitution of a substituent at the position increases the stability of the molecule and extends the lifetime when the device is driven.

(In the formulas (1a ′), (1b ′) and (1h ′), any one of R ′ is a single bond bonded to L, and R ′ and R other than a single bond are each independently hydrogen. Atom, fluorine atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or a substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms is there.)

Ar ^{2 in} Formula (1-1) is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted phenanthryl group. Ar ² is one of these substituents, and it is considered that the carrier balance is more suitable when the device is manufactured and driven.
The biphenyl group in this application refers to any of 2-biphenyl group, 3-biphenyl group and 4-biphenyl group.

L in Formula (1-1) is preferably a single bond or a substituted or unsubstituted phenylenyl group, and more preferably a single bond. N is preferably 1.
When L is a single bond, it is considered that a more suitable carrier balance is obtained when an element is formed and driven.

R ¹ to R ^{8 in} the formula (1-1) are preferably all hydrogen atoms. Since all of R ¹ to R ⁸ of the anthracene ring are hydrogen atoms, the compound is considered to be stable, and is considered to have a long life when driven as an element.

Specific examples of the anthracene compound represented by the formula (1-1) are shown below.

[Azine compounds]
Ar ^{11 of the} azine compound represented by the formula (2-1) is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms and having one or more substituted or unsubstituted carbazole skeleton-containing groups as substituents. The carbazole skeleton-containing group is preferably a carbazolyl group. Preferably it has 1 or 2 carbazolyl groups.
The substituted or unsubstituted carbazole skeleton-containing group for Ar ¹¹ is preferably a substituted or unsubstituted 9-carbazolyl group.

The carbazole skeleton-containing group is preferably selected from any of the following.

(Wherein L ¹⁰⁰ is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
Ar ¹⁰⁰ is a hydrogen atom or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms. )

Specifically, compounds represented by the following formulas can be exemplified.

Az in the formula (2-1) is a substituted or unsubstituted aromatic nitrogen-containing 6-membered cyclic group, preferably a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, or a substituted or unsubstituted Triazinyl group.

Az in the formula (2-1) is preferably a group represented by the following formula (2a).

(In Formula (2a), X ¹ to X ³ are each independently a nitrogen atom or CH, and at least two of X ¹ to X ³ are nitrogen atoms.
Ar ¹² and Ar ¹³ are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 (preferably 6 to 12) ring-forming carbon atoms. )

Regarding the group represented by the formula (2a), X ¹ and X ² are preferably nitrogen atoms, and X ³ is preferably CH.
The number of carbon atoms of ^{Ar 12} in the formula (2a) is preferably less than or equal to the number of carbon atoms of ^{Ar 13.}
In particular, Ar ¹² in formula (2a) is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted biphenyl group.

The azine compound represented by the formula (2-1) is preferably an azine compound represented by the following formula (2-2).

(In the formula (2-2), k is an integer of 1 to 3, n is an integer of 0 to 3,
R ¹¹ to R ¹⁸ are each independently a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 ring atoms. Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 ring carbon atoms, substituted or unsubstituted An aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted 3 to 30 carbon atoms An alkylsilyl group, a substituted or unsubstituted dialkylarylsilyl group having 8 to 40 carbon atoms, a substituted or unsubstituted alkyldiarylsilyl group having 13 to 50 carbon atoms, a substituted Or an unsubstituted triarylsilyl group having 18 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a halogen atom, a cyano group, A hydroxyl group, a nitro group, or a carboxy group.
Az is a substituted or unsubstituted aromatic nitrogen-containing 6-membered cyclic group. )

K in the formula (2-2) is preferably 2.

R ¹¹ to R ^{18 in} the formula (2-2) are preferably hydrogen atoms.

Az in the formula (2-2) is the same as that in the formula (2-1).

Specific examples of the azine compound represented by the formula (2-1) are shown below.

Hereinafter, examples of each group of the above-described anthracene compound and azine compound of the present invention will be described.
The “ring-forming carbon” means a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring, and the “ring-forming atom” includes a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring). ) Is a carbon atom and a hetero atom.
In the present application, the hydrogen atom includes light hydrogen, deuterium, and tritium.

The aromatic hydrocarbon group (aryl group) preferably has 6 to 20 ring carbon atoms, and more preferably 6 to 12 ring carbon atoms.
Specific examples of the aromatic hydrocarbon group include phenyl, tolyl, xylyl, naphthyl, phenanthryl, pyrenyl, chrysenyl, benzo [c] phenanthryl, benzo [g] chrysenyl, benzoanthryl. , Triphenylenyl group, fluorenyl group, 9,9-dimethylfluorenyl group, benzofluorenyl group, dibenzofluorenyl group, biphenyl group, terphenyl group, fluoranthenyl group, etc., preferably phenyl group, Biphenyl group and naphthyl group.
Examples of the aromatic hydrocarbon group having a substituent include a tolyl group, a xylyl group, and a 9,9-dimethylfluorenyl group.

The aromatic heterocyclic group (heteroaryl group) preferably has 5 to 20 ring atoms, and more preferably 5 to 14 ring atoms.
Specific examples of the aromatic heterocyclic group include pyrrolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridyl, triazinyl, indolyl, isoindolyl, imidazolyl, benzimidazolyl, indazolyl, imidazol [ 1,2-a] pyridinyl group, furyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, azadibenzofuranyl group, thiophenyl group, benzothiophenyl group, dibenzothiophenyl group, azadibenzothiophenyl group Quinolyl group, isoquinolyl group, quinoxalinyl group, quinazolinyl group, naphthyridinyl group, carbazolyl group, azacarbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, phenothiazinyl group, phenoxazinyl group, Xazozolyl group, oxadiazolyl group, furazanyl group, benzoxazolyl group, thienyl group, thiazolyl group, thiadiazolyl group, benzthiazolyl group, triazolyl group, tetrazolyl group, etc., preferably dibenzofuranyl group, dibenzothiophenyl group, It is a carbazolyl group.

Examples of the alkyl group include linear, branched and cyclic alkyl groups. The number of carbon atoms is preferably 1-20, and more preferably 1-10. Examples of linear and branched alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, and n-hexyl. Group, n-heptyl group, n-octyl group and the like, preferably methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group and tert-butyl group. More preferred are methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, and t-butyl group.
Examples of the cyclic alkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a 2-norbornyl group. Preferred are a cyclopentyl group and a cyclohexyl group.

The alkoxy group is represented as —OY, and examples of Y include the above alkyl examples. Specific examples of the alkoxy group include a methoxy group and an ethoxy group.
The aryloxy group is represented by —OZ, and examples of Z include the above aryl groups. Specific examples of the aryloxy group include a phenoxy group and a naphthyloxy group.

The aralkyl group is represented by —Y—Z. Examples of Y include alkylene examples corresponding to the above alkyl examples, and examples of Z include the above aryl examples. The aryl part of the aralkyl group preferably has 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms. The alkyl moiety preferably has 1 to 10 carbon atoms, particularly preferably 1 to 6 carbon atoms. For example, benzyl group, phenylethyl group, 2-phenylpropan-2-yl group and the like can be mentioned.

Examples of the haloalkyl group include groups in which one or more halogen atoms (a fluorine atom, a chlorine atom, and a bromine atom are preferable, and a fluorine atom is preferably substituted) on the alkyl group having 1 to 30 carbon atoms described above. . Specific examples include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a trifluoromethylmethyl group, and a pentafluoroethyl group. Preferably, they are a trifluoromethyl group and a pentafluoroethyl group.

Examples of the haloalkoxy group include groups in which one or more halogens (including a fluorine atom, a chlorine atom and a bromine atom are preferable, and a fluorine atom is preferably substituted) on the above alkoxy group. Preferably, it is a trifluoromethoxy group.

The alkylsilyl group is a silyl group substituted with 1 to 3 alkyl groups, and the arylsilyl group is a silyl group substituted with 1 to 3 aryl groups. The alkyl group and aryl group are the same as those described above.
The trialkylsilyl group is represented as —Si (R ^a ) (R ^b ) (R ^c ), and examples of (R ^a ), (R ^b ) and (R ^c ) include the alkyl groups described above. Specific examples include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, propyldimethylsilyl group and the like.

The dialkylarylsilyl group is represented as —Si (R ^a ) (R ^b ) (Ar ^c ), and examples of (R ^a ) and (R ^b ) include the alkyl groups described above, and examples of (Ar ^c ) Examples of the aryl group include the aryl groups described above. Specific examples include a phenyldimethylsilyl group.

The alkyldiarylsilyl group is represented as —Si (R ^a ) (Ar ^b ) (Ar ^c ), and examples of (R ^a ) include the alkyl groups described above. Examples of (Ar ^b ) and (Ar ^c ) Examples of the aryl group include the aryl groups described above. Specific examples include a methyldiphenylsilyl group.
The triarylsilyl group is represented as —Si (Ar ^a ) (Ar ^b ) (Ar ^c ), and examples of (Ar ^a ), (Ar ^b ) and (Ar ^c ) include the aryl groups described above. . Specific examples include a triphenylsilyl group.

Examples of the alkenyl group include vinyl, propenyl, butenyl, pentenyl, pentadienyl, hexenyl, hexadienyl, heptenyl, octenyl, octadienyl, 2-ethylhexenyl, decenyl and the like.
Examples of the alkynyl group include ethynyl group and methylethynyl group.

In the anthracene compound represented by the formula (1-1) and the azine compound represented by the formula (2-1), the substituents of “substituted or unsubstituted... , Substituted silyl groups, aryl groups, heteroaryl groups, alkoxy groups, aralkyl groups, haloalkyl groups, and other halogen atoms (including fluorine, chlorine, bromine, iodine, etc., preferably fluorine atoms), silyl groups , Hydroxyl group, nitro group, cyano group, carboxy group, aryloxy group and the like.

The anthracene compound represented by the formula (1-1) can be synthesized by referring to, for example, WO2009 / 069566 and WO2011 / 054442.
The azine compound represented by the formula (2-1) can be synthesized by referring to, for example, WO2003 / 080760.

The content of the anthracene compound represented by the formula (1-1) in the organic light emitting layer adjacent to the electron transport layer is not particularly limited, but is, for example, 1 to 100% by weight, preferably 80 to 100% by weight, More preferably, it is 90 to 100% by weight.
The content of the azine compound represented by the formula (2-1) in the electron transport layer adjacent to the organic light emitting layer is not particularly limited, but is, for example, 1 to 100% by weight, preferably 50 to 100% by weight.

[Element structure]
In the organic EL device of the present invention, other configurations are not particularly limited as long as the above-described stacked structure of the electron transport layer and the organic light emitting layer is included, and a known device configuration can be adopted. Hereinafter, the example of an organic EL element is demonstrated using drawing.

Embodiment 1
FIG. 1 is a schematic view showing a layer structure of an embodiment of the organic EL device of the present invention.
In the organic EL element 1, the anode 20, the hole injection layer 30, the hole transport layer 40, the organic light emitting layer 50, the electron transport layer 60, the electron injection layer 70, and the cathode 80 are laminated on the substrate 10 in this order. It has a configuration. The hole transport zone is a hole transport layer and a hole injection layer. Similarly, the electron transport zone is the electron transport layer 60 and the electron injection layer 70. The hole injection layer 30 and the electron injection layer 70 do not have to be formed, but preferably one or more layers are formed respectively.

In the organic EL device of this embodiment, the organic light emitting layer 50 and the electron transport layer 60 are formed adjacent to each other. The organic light emitting layer 50 is a layer containing the anthracene compound represented by the above formula (1-1), and the electron transport layer 60 contains the azine compound represented by the above formula (2-1). Is a layer.

FIG. 1 schematically shows the organic EL element 1 as one light emitting unit, but two or more organic EL elements 1 are combined, or the organic EL element 1 is combined with another organic EL element. Thus, an organic EL multicolor light emitting device can be formed.

FIG. 2 is a schematic cross-sectional view showing an example of an organic EL light emitting device using the organic EL element of the present invention.
The organic EL light emitting device is a device having a blue EL element 1B (first element), a green EL element 1G (second element), and a red EL element 1R (third element) in parallel on a substrate 10.
The configuration of each color organic EL element uses

patterned anodes

20B, 20G, and 20R, and the organic light emitting layer corresponds to each color, and the blue light emitting layer 50B, the green light emitting layer 50G, and the red light emitting layer 50R, respectively. The organic EL element 1 is the same as that described above except that the hole injection layer 30 and the electron injection layer 70 are not formed. Between each light emitting layer, the insulating layer 54 which isolate | separates two light emitting layers is provided.
The blue EL element 1B, the green EL element 1G, and the red EL element 1R share each organic layer (the hole transport layer 40 and the electron transport layer 60) except for the organic light emitting layer.

In this example, three colors of organic EL elements are used. However, the present invention is not limited to this, and two (two colors) or four or more colors of organic EL elements may be used. For example, in the case of a device in which two-color organic EL elements are arranged in parallel, multicolor light emission is possible by setting the emission color of one organic EL element to blue to green and the emission color of the other organic EL elements to yellow to red. It becomes.
In addition, although both the hole transport layer 40 and the electron transport layer 60 are formed as a common layer, either one may be used. In this case, the organic EL element of this invention should just be used for one of the used organic EL elements. Each EL element may be a fluorescent light emitting element or a phosphorescent light emitting element.
In the present invention, the organic EL element of the present invention is preferably used as the fluorescent blue EL element.

Embodiment 2
FIG. 3 is a schematic view showing the layer structure of another embodiment of the organic EL device of the present invention.
The organic EL element 2 is an example of a tandem organic EL element in which two light emitting units are stacked via a charge generation layer.
The organic EL element 2 includes an anode 20, a first hole transport layer 41, a first organic light emitting layer 51, a first electron transport layer 61, a charge generation layer 90, a second hole transport layer 42, a first hole on the substrate 10. The second organic light-emitting layer 52, the third organic light-emitting layer 53, the second electron transport layer 62, and the cathode 80 are stacked in this order. A region sandwiched between the anode 20 and the charge generation layer 90 is the first light emitting unit 3A, and a region sandwiched between the charge generation layer 90 and the cathode 80 is the second light emitting unit 3B.

The charge generation layer 90 is a layer that generates charge when a voltage is applied to the organic EL element 2, and injects electrons into the first electron transport layer 61 and injects holes into the second hole transport layer 42. .
As a material of the charge generation layer 90, a known material, for example, a material described in US 7,358,661 can be used. Specifically, oxides, nitrides, iodides, borides containing one or more metal elements such as In, Sn, Zn, Ti, Zr, Hf, V, Mo, Cu, Ga, Sr, La, and Ru. Etc.

In the present embodiment, the first organic light emitting layer 51 of the first light emitting unit 3A is a layer containing the anthracene compound represented by the above formula (1-1), and the first electron transport layer 61 is the above-described layer. This is a layer containing an azine compound represented by the formula (2-1).
In the organic EL element 2, for example, the first organic light emitting layer 51 is a fluorescent light emitting layer that emits blue light (for example, a peak wavelength is 430 to 500 nm), and the second organic light emitting layer 52 is green light (for example, a peak wavelength is 500 to 500 nm). 570 nm) and the third organic light-emitting layer 53 is a phosphorescent light-emitting layer that emits red light (for example, a peak wavelength of 570 nm or more), thereby obtaining an organic EL element that emits white light.

In the present embodiment, two light emitting units are used. However, the present invention is not limited to this, and three or more light emitting units may be formed. Further, the second organic light emitting layer 52 and the third organic light emitting layer 53 may be combined to form a single layer.
In the present embodiment, the laminated structure peculiar to the present application is used for the first light emitting unit 3A. However, the present invention is not limited thereto, and for example, the laminated structure peculiar to the present application may be used for the second light emitting unit 3B. You may use for both unit 3A and the 2nd light emission unit 3B.
Each organic light emitting layer may be a fluorescent light emitting layer or a phosphorescent light emitting layer, and the emission color is not limited. What is necessary is just to set suitably according to a use from a well-known structure.

As in

Embodiments

1 and 2 described above, the organic EL element of the present invention can employ various known configurations. In addition, light emission of the light emitting layer can be extracted from the anode side, the cathode side, or both sides.

In the organic EL element of the present invention, other configurations of the organic light-emitting layer and the electron transport layer adjacent to the organic light-emitting layer are not particularly limited, and known materials and the like can be used.
Hereinafter, although the layer of the element of Embodiment 1 is demonstrated easily, the material applied to the organic EL element of this invention is not limited to the following.

[substrate]
As the substrate, a glass plate, a polymer plate or the like can be used.
Examples of the glass plate include soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz. Examples of the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfone, and polysulfone.

[anode]
The anode is made of, for example, a conductive material, and a conductive material having a work function larger than 4 eV is suitable.
Examples of the conductive material include carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium, and their alloys, ITO substrate, tin oxide used for NESA substrate, indium oxide, and the like. Examples thereof include metal oxides and organic conductive resins such as polythiophene and polypyrrole.
The anode may be formed with a layer structure of two or more layers if necessary.

[cathode]
The cathode is made of, for example, a conductive material, and a conductive material having a work function smaller than 4 eV is suitable.
Examples of the conductive material include, but are not limited to, magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride, and alloys thereof.
Examples of the alloy 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 cathode may be formed with a layer structure of two or more layers, and the cathode can be produced by forming a thin film from the conductive material by a method such as vapor deposition or sputtering.

When light emitted from the light emitting layer is taken out from the cathode, the transmittance of the cathode for light emission is preferably greater 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.

[Organic light emitting layer]
The organic light emitting layer is not particularly limited as long as the organic light emitting layer adjacent to the electron transport layer contains an anthracene compound represented by the formula (1-1), and may be any of a known fluorescent light emitting layer and phosphorescent light emitting layer. In the present invention, a fluorescent light-emitting layer is preferable, and an anthracene derivative is particularly preferable as a host material of the light-emitting layer.

The light emitting layer may be a double host (also referred to as host / cohost). Specifically, the carrier balance in the light emitting layer may be adjusted by combining an electron transporting host and a hole transporting host in the light emitting layer.
Moreover, it is good also as a double dopant. In the light emitting layer, each dopant emits light by adding two or more dopant materials having a high quantum yield. For example, a yellow light emitting layer may be realized by co-evaporating a host, a red dopant, and a green dopant.

The light emitting layer may be a single layer or a laminated structure. When the light emitting layer is stacked, the recombination region can be concentrated on the light emitting layer interface by accumulating electrons and holes at the light emitting layer interface. This improves the quantum efficiency.

[Hole injection layer and hole transport layer (hole injection / transport layer)]
The hole injection / transport layer is a layer that assists hole injection into the light emitting layer and transports it to the light emitting region, and has a high hole mobility and a small ionization energy of usually 5.6 eV or less.
Examples of materials that can be used for the hole injection / transport layer include triazole derivatives (see US Pat. No. 3,112,197), oxadiazole derivatives (see US Pat. No. 3,189,447), imidazole, and the like. Derivatives (see Japanese Patent Publication No. 37-16096), polyarylalkane derivatives (US Pat. No. 3,615,402, US Pat. No. 3,820,989, US Pat. No. 3,542,544) JP-B-45-555, JP-A-51-10983, JP-A-51-93224, JP-A-55-17105, JP-A-56-4148, JP-A-55-108667, JP-A-55-156953. No. 56-36656), pyrazoline derivatives and pyrazolone derivatives (US Pat. No. 3,180,729, No. 1) 278,746, JP 55-88064, 55-88065, 49-105537, 55-51086, 56-80051, 56-88141. No. 57-45545, No. 54-112537, No. 55-74546, etc.), phenylenediamine derivatives (US Pat. No. 3,615,404, JP-B 51-10105, 46-3712, 47-25336, 54-1119925, etc.), arylamine derivatives (US Pat. Nos. 3,567,450, 3,240,597) No. 3,658,520, No. 4,232,103, No. 4,175,961, No. 4,012,37. Specification, JP-B-49-35702, JP-A-39-27577, JP-A-55-144250, JP-A-56-119132, JP-A-56-22437, West German patent No. 1,110,518 Etc.), amino-substituted chalcone derivatives (see US Pat. No. 3,526,501 etc.), oxazole derivatives (disclosed in US Pat. No. 3,257,203 etc.), styrylanthracene, etc. Derivatives (see JP 56-46234 A), fluorenone derivatives (see JP 54-110837 A, etc.), hydrazone derivatives (US Pat. No. 3,717,462, JP 54-59143 A) No. 55-52063, No. 55-52064, No. 55-46760, No. 57-11350, No. 57 -148749, JP-A-2-311591, etc.), stilbene derivatives (JP-A 61-210363, 61-228451, 61-14642, 61-72255, 62-47646, 62-36674, 62-10652, 62-30255, 60-93455, 60-94462, 60-174749, 60-175052, etc.), silazane derivatives (US Pat. No. 4,950,950), polysilanes (JP-A-2-204996), aniline copolymers (JP-A-2-282263) And the like.
In addition, inorganic compounds such as p-type Si and p-type SiC can also be used as the hole injection material.

As the material of the hole injection / transport layer, a cross-linkable material can be used. As the cross-linkable hole injection / transport layer, for example, Chem. Mater. 2008, 20, 413-422, Chem. Mater. Examples include a layer obtained by insolubilizing a cross-linking material such as 2011, 23 (3), 658-681, WO2008108430, WO2009102027, WO2009123269, WO2010016555, WO2010018813 by heat, light or the like.

[Electron injection layer and electron transport layer (electron injection / transport layer)]
The electron injection / transport layer is a layer that assists the injection of electrons into the light emitting layer and transports it to the light emitting region, and has a high electron mobility.
In the organic EL element, since emitted light is reflected by an electrode (for example, a cathode), it is known that light emitted directly from the anode interferes with light emitted via reflection by the electrode. In order to efficiently use this interference effect, the electron injecting / transporting layer is appropriately selected with a film thickness of several nm to several μm. However, particularly when the film thickness is large, in order to avoid a voltage increase, 10 ⁴ to 10 ^6. The electron mobility is preferably at least 10 ⁻⁵ cm ² / Vs or more when an electric field of V / cm is applied.

As described above, in the present invention, the electron transport layer adjacent to the organic light emitting layer contains an azine compound represented by the formula (2-1). As a material that can be used by mixing with another electron injection / transport layer or an azine compound, an aromatic heterocyclic compound containing at least one hetero atom in the molecule is preferable, and a nitrogen-containing ring derivative is particularly preferable. The nitrogen-containing ring derivative is preferably an aromatic ring having a nitrogen-containing 6-membered ring or 5-membered ring skeleton, or a condensed aromatic ring compound having a nitrogen-containing 6-membered ring or 5-membered ring skeleton.

In addition, an organic layer having semiconductivity may be formed by doping (n) with a donor material and doping (p) with an acceptor material. A typical example of N doping is to dope a metal such as Li or Cs to the material of the electron transport layer, and a typical example of P doping is to dope an acceptor material such as F4TCNQ to the material of the hole transport layer. (See, for example, Japanese Patent No. 3695714).

For the formation of each layer of the organic EL device of the present invention, a known method such as a dry film forming method such as vacuum deposition, sputtering, plasma, or ion plating, or a wet film forming method such as spin coating, dipping, or flow coating is applied. be able to.
The thickness of each layer is not particularly limited, but must be set to an appropriate 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.

The organic EL device of the present invention can be used in a panel module used for various displays as a light emitting device.
Further, the panel module of the present invention can be used for a display device such as a television, a portable terminal, and a personal computer, lighting, and the like.

Example 1
A glass substrate with an ITO transparent electrode line of 25 mm × 75 mm × 1.1 mm (manufactured by Geomatic: ITO film thickness 130 nm) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, and further UV (ultraviolet) ozone cleaning for 30 minutes.
The glass substrate with the transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum deposition apparatus, and the compound HA is first deposited on the surface on which the transparent electrode line is formed so as to cover the transparent electrode. A film was formed. A compound HT1 was vapor-deposited on the HA film to form a 95 nm-thick hole transport layer. On this hole transport layer, the compound H100, which is a fluorescent host, and the compound BD, which is a fluorescent dopant, were co-evaporated with a thickness of 25 nm to obtain a fluorescent light emitting layer. The dopant concentration was 5% by weight.
Subsequently, the compound ET100 was vapor-deposited on this fluorescent light emitting layer, and an electron transport layer having a thickness of 20 nm was formed. Following the formation of the electron transport layer, the compound ET1 was vapor-deposited to form an electron injection layer having a thickness of 5 nm. Furthermore, LiF with a thickness of 1 nm and metal Al with a thickness of 80 nm were sequentially laminated to form a cathode to manufacture an organic EL device. Note that LiF, which is an electron injecting electrode, was formed at a deposition rate of 1 Å / min.

The compounds used in the examples are as follows.

Example 2
An organic EL device is formed in the same manner as in Example 1 except that the hole transport layer is formed using the following compound HT2 instead of the compound HT1, and the electron transport layer is formed using the following compound ET200 instead of the compound ET100. did.

Example 3
An organic EL device was formed in the same manner as in Example 1 except that the compound ET200 was used instead of the compound ET100 to form the electron transport layer.

Example 4
A hole transport layer is formed using compound HT2 instead of compound HT1, a fluorescent light emitting layer is formed using compound H200 below instead of compound H100, and an electron transport layer is formed using compound ET200 instead of compound ET100. An organic EL element was formed in the same manner as in Example 1 except that it was formed.

Example 5
An organic EL device was formed in the same manner as in Example 1 except that the fluorescent light emitting layer was formed using Compound H200 instead of Compound H100 and the electron transport layer was formed using Compound ET200 instead of Compound ET100.

Comparative Example 1
A hole transport layer is formed using compound HT2 instead of compound HT1, a fluorescent light emitting layer is formed using compound H300 below instead of compound H100, and an electron transport layer is formed using compound ET200 instead of compound ET100. An organic EL element was formed in the same manner as in Example 1 except that it was formed.

The organic EL devices produced in the examples and comparative examples are made to emit light by direct current drive, and the luminance (L), chromaticity (x, y), luminous efficiency η (lm / W) at the current density of 10 mA / cm ² , external Quantum efficiency (EQE:%) was measured. Further, the element lifetime (LT80) was measured. The results are shown in Table 1.
The values of luminance, light emission efficiency η, external quantum efficiency (EQE), and element lifetime (LT80) in the table are relative values with the value of Comparative Example 1 being 100.

The organic EL element of the present invention has a long life and can be driven with high efficiency. Accordingly, it can be suitably used as a display device such as a television, a portable terminal, a personal computer, or a light emitting element such as an illumination.

Although several embodiments and / or examples of the present invention have been described in detail above, those skilled in the art will appreciate that these exemplary embodiments and / or embodiments are substantially without departing from the novel teachings and advantages of the present invention. It is easy to make many changes to the embodiment. Accordingly, many of these modifications are within the scope of the present invention.
All the contents of the Japanese application specification that is the basis of the priority of Paris in this application are incorporated herein.

Claims

Between the anode and cathode facing each other, from the anode side, at least an organic light emitting layer and an electron transport layer are adjacent to each other in this order,
The organic light emitting layer contains an anthracene compound represented by the following formula (1-1):
The electron transport layer contains an azine compound represented by the following formula (2-1):
Organic electroluminescence device.

(In the formula (1-1), Ar 1 is a substituted or unsubstituted aromatic hydrocarbon group having 15 to 60 ring carbon atoms.
Ar 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
L is a single bond or a substituted or unsubstituted arylene group having 6 to 10 ring carbon atoms.
R 1 to R 8 are each independently a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted An unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or a substituted or unsubstituted ring An arylsilyl group having 8 to 50 carbon atoms formed.
n is an integer of 1 to 4, and when n is 2 or more, the plurality of L may be the same or different. )

(In Formula (2-1),
Ar 11 is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms having at least one substituted or unsubstituted carbazole skeleton-containing group as a substituent.
Az is a substituted or unsubstituted aromatic nitrogen-containing 6-membered cyclic group. )
2. The organic electroluminescence device according to claim 1, wherein the substituted or unsubstituted carbazole skeleton-containing group of the azine compound represented by the formula (2-1) is a substituted or unsubstituted 9-carbazolyl group.
2. The organic electroluminescence device according to claim 1, wherein Ar 11 in the formula (2-1) is selected from any of the following.

(Wherein L 100 is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
Ar 100 is a hydrogen atom or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms. )
The organic electroluminescence device according to claim 1 or 2, wherein the azine compound is a compound represented by the following formula (2-1).

(In the formula (2-2), k is an integer of 1 to 3, n is an integer of 0 to 3,
R 11 to R 18 are each independently a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 ring atoms. Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 ring carbon atoms, substituted or unsubstituted An aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted 3 to 30 carbon atoms An alkylsilyl group, a substituted or unsubstituted dialkylarylsilyl group having 8 to 40 carbon atoms, a substituted or unsubstituted alkyldiarylsilyl group having 13 to 50 carbon atoms, a substituted Or an unsubstituted triarylsilyl group having 18 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a halogen atom, a cyano group, A hydroxyl group, a nitro group, or a carboxy group.
Az is a substituted or unsubstituted aromatic nitrogen-containing 6-membered cyclic group. )
The organic electroluminescence device according to claim 4, wherein Az in the formula (2-2) is a group represented by the following formula (2a).

(In Formula (2a), X 1 to X 3 are each independently a nitrogen atom or CH, and at least two of X 1 to X 3 are nitrogen atoms.
Ar 12 and Ar 13 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms. )
The organic electroluminescence device according to claim 5, wherein X 1 and X 2 in the formula (2a) are nitrogen atoms, and X 3 is CH.
The organic electroluminescent element according to claim 5 or 6, wherein the carbon number of Ar 12 in the formula (2a) is equal to or less than the carbon number of Ar 13 .
The organic electro of any one of claims 5 to 7, wherein Ar 12 in the formula (2a) is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted biphenyl group. Luminescence element.
The organic electroluminescence device according to any one of claims 4 to 8, wherein k in the formula (2-2) is 2.
10. The organic electroluminescence device according to claim 4, wherein R 11 to R 18 in the formula (2-2) are hydrogen atoms.
Ar 1 in the formula (1-1) is a substituent represented by the following formula (1a), (1b), (1c), (1d), (1e), (1f), (1g) or (1h) 11. The organic electroluminescence device according to claim 1, wherein the organic electroluminescence device is any one of the above.

(In formulas (1a) to (1h), one of R is a single bond bonded to L, and each R other than a single bond is independently a hydrogen atom, a fluorine atom, a cyano group, substituted or unsubstituted. An alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted ring forming carbon atom having 6 to 6 carbon atoms. 30 aryloxy groups, substituted or unsubstituted trialkylsilyl groups having 3 to 40 carbon atoms, or substituted or unsubstituted arylsilyl groups having 8 to 50 carbon atoms.)
The Ar 1 in the formula (1-1) is any one of substituents represented by the following formulas (1a), (1b), (1c) or (1h). Organic electroluminescence device.

(In the formulas (1a) to (1c) and (1h), one of R is a single bond bonded to L, and each R other than a single bond is independently a hydrogen atom, a fluorine atom, a cyano group, Substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted ring formation A C6-C30 aryloxy group, a substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or a substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms.)
The organic compound according to any one of claims 1 to 12, wherein Ar 1 in the formula (1-1) is any one of substituents represented by the following formula (1a '), (1b'), or (1h '). Electroluminescence element.

(In the formulas (1a ′), (1b ′) and (1h ′), any one of R ′ is a single bond bonded to L, and R ′ and R other than a single bond are each independently hydrogen. Atom, fluorine atom, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or a substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms is there.)
14. The organic electroluminescence device according to claim 1, wherein L in the formula (1-1) is a single bond.
A panel module using the organic electroluminescence element according to any one of claims 1 to 14.
Electronic equipment using the panel module according to claim 15.