US20200388768A1

US20200388768A1 - Organic electroluminescence device and electronic apparatus

Info

Publication number: US20200388768A1
Application number: US16/971,252
Authority: US
Inventors: Tetsuya Masuda; Yuki Nakano; Takushi Shiomi
Original assignee: Idemitsu Kosan Co Ltd
Current assignee: Idemitsu Kosan Co Ltd
Priority date: 2018-02-20
Filing date: 2019-02-20
Publication date: 2020-12-10
Also published as: US11765972B2; US20210009527A1; KR20200123105A; WO2019163825A1; CN111712493B; JP7244485B2; CN111712493A; JPWO2019163826A1; WO2019163826A1

Abstract

An organic electroluminescence device, comprising: an anode, an emitting layer, a first electron-transporting layer, a second electron-transporting layer and a cathode in this order, wherein the second electron-transporting layer comprises a compound represented by the following formula (1), and the emitting layer comprises a compound represented by the following formula (10).

Description

TECHNICAL FIELD

The invention relates to an organic electroluminescence device and an electronic apparatus.

BACKGROUND ART

When voltage is applied to an organic electroluminescence device (hereinafter, referred to as an organic EL device in several cases), holes and electrons are injected into an emitting layer from an anode and a cathode, respectively. Then, thus injected holes and electrons are recombined in the emitting layer, and excitons are formed therein.
The organic EL device includes the emitting layer between the anode and the cathode. Further, the organic EL device has a stacked structure including an organic layer such as a hole-injecting layer, a hole-transporting layer, an electron-injecting layer, and an electron-transporting layer in several cases.
Documents disclosing such an organic EL device include, for example, Patent Documents 1 to 4 below

RELATED ART DOCUMENTS

Patent Documents

Patent Document 1: WO2005/113531
Patent Document 2: US2016/0020405
Patent Document 3: WO2016/126022
Patent Document 4: US2017/0018723

SUMMARY OF THE INVENTION

An object of the invention is to provide a high performance organic electroluminescence device. In particular, it is an object of the invention to provide an organic electroluminescence device having high luminous efficiency, an organic electroluminescence device having long life, or an organic electroluminescence device having high luminous efficiency and long life. Moreover, an object of the invention is providing an electronic device using such an organic electroluminescence device.
According to the invention, the following organic EL device and electric apparatus can be provided.
1. An organic electroluminescence device, comprising:
an anode, an emitting layer, a first electron-transporting layer, a second electron-transporting layer and a cathode in this order, wherein
the second electron-transporting layer comprises a compound represented by the following formula (1), and
the emitting layer comprises a compound represented by the following formula (10):
wherein in the formula (1),
L₁is a single bond, or a group selected from the group consisting of
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted biphenylene group,
a substituted or unsubstituted terphenylene group,
a substituted or unsubstituted quarterphenylene group,
a substituted or unsubstituted fused arylene group including 10 to 30 carbon atoms that form a ring (hereinafter referred to as “ring carbon atoms”), and
a group in that 1 to 3 substituted or unsubstituted phenylene groups and 1 to 3 substituted or unsubstituted fused arylene groups including 10 to 30 ring carbon atoms are linked via a single bond;
Ar¹and Ar²are independently a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 30 atoms that form a ring (hereinafter referred to as “ring atoms”) and no nitrogen atom;
X₁to X₃are independently N or CR₁;
provided that two or more of X₁to X₃are N; R₁does not form a ring by bonding with adjacent L₁, Ar₁or Ar₂;
R₁'s are independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 20 carbon atoms, a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 30 ring atoms, except for a carbazolyl group;
HA is a monovalent group represented by the following formula (HA):
wherein in the formula (HA),
Y₁to Y₈are independently N or CR₂; R₂'s are independently a hydrogen atom or a substituent;
when plural R₂'s are present, the plural R₂'s may be the same or different; plural R₂'s substituting on adjacent carbon atoms may form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other;
provided that one of Y₁to Y₈and atoms constituting the substituted or unsubstituted, saturated or unsaturated ring formed by bonding R₂'s with each other is a carbon atom bonded with L₁;
X₄is O or S;
wherein in the formula (10),
R₁₁to R₁₈are independently a hydrogen atom,
a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms,
a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms,
a substituted or unsubstituted alkylthio group including 1 to 50 carbon atoms,
a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms,
a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms,
a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms,
—Si(R₁₀₁)(R₁₀₂)(R₁₀₃),

—C(═O)R₁₀₄,

—COOR₁₀₅,

—N(R₁₀₆)(R₁₀₇),
a halogen atom, a cyano group, a nitro group,
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
R₁₀₁to R₁₀₇are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
when two or more of each of R₁₀₁to R₁₀₇are present, the two or more of each of R₁₀₁to R₁₀₇may be the same or different;
provided that at least one of Ar₁₁and Ar₁₂is a monovalent group represented by the following formula (11);
wherein in the formula (11),
one of R₂₁to R₂₈is bonded with L₁or L₁₂; and
R₂₁to R₂₈which are not bonded with L₁₁or L₁₂are independently a hydrogen atom,
a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms,
a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms,
a substituted or unsubstituted alkylthio group including 1 to 50 carbon atoms,
a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms,
a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms,
a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms,
—Si(R₁₀₁)(R₁₀₂)(R₁₀₃),

—C(═O)R₁₀₄,

—COOR₁₀₅,

—N(R₁₀₆)(R₁₀₇),
a halogen atom, a cyano group, a nitro group,
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
R₁₀₁to R₁₀₇are as defined above:
Ar₁₁or Ar₁₂, which is not the monovalent group represented by the formula (11), is an unsubstituted aryl group including 6 to 50 ring carbon atoms, an aryl group including 6 to 50 ring carbon atoms, which is substituted with an unsubstituted alkyl group including 1 to 50 carbon atoms, or an aryl group including 6 to 50 ring carbon atoms, which is substituted with an unsubstituted aryl group including 6 to 50 ring carbon atoms;
L₁₁and L₁₂are independently a single bond, a substituted or unsubstituted alkylene group including 1 to 50 carbon atoms, a substituted or unsubstituted arylene group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group including 5 to 50 ring atoms.
2. An electronic apparatus provided with the organic electroluminescence device according to the above 1.
According to the invention, high performance organic electroluminescence device is provided. In particular, an organic electroluminescence device having high luminous efficiency, an organic electroluminescence device having long life, or an organic electroluminescence device having high luminous efficiency and long life is provided. Moreover, according to the invention, an electronic device using such an organic electroluminescence device is provided.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a diagram showing a schematic configuration of the first embodiment of an organic EL device of the invention.

MODE FOR CARRYING OUT THE INVENTION

Definition

In the present specification, a hydrogen atom means an atom including isotopes different in the number of neutrons, namely, a protium, a deuterium and a tritium.
In the present specification, a term “ring carbon atoms” represents the number of carbon atoms among atoms forming a subject ring itself of a compound having a structure in which atoms are bonded in a ring form (for example, a monocyclic compound, a fused ring compound, a cross-linked compound, a carbocyclic compound or a heterocylic compound). When the subject ring is substituted by a substituent, the carbon contained in the substituent is not included in the number of ring carbon atoms. The same shall apply to the “ring carbon atoms” described below, unless otherwise noted. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. Further, for example, a 9,9-diphenylfluorenyl group has 13 ring carbon atoms, and a 9,9′-spirobifluorenyl group has 25 ring carbon atoms.
Further, when the benzene ring or the naphthalene ring is substituted by an alkyl group as a substituent, for example, the number of carbon atoms of the alkyl group is not included in the ring carbon atoms.
In the present specification, a term “ring atoms” represents the number of atoms forming a subject ring itself of a compound having a structure in which atoms are bonded in a ring form (for example, a monocycle, a fused ring and a ring assembly) (for example, a monocyclic compound, a fused ring compound, a cross-linked compound, a carbocyclic compound or a heterocyclic compound). The atoms that do not form the ring (e.g., a hydrogen atom that terminates bonds which are not used to form the ring) or the atoms contained in a substituent where the ring is substituted by the substituent is not included in the number of ring atom. The same shall apply to the “ring atoms” described below, unless otherwise noted. For example, a pyridine ring has 6 ring atoms, a quinazoline ring has 10 ring atoms, and a furan ring has 5 ring atoms. A hydrogen atom bonded with a carbon atom of the pyridine ring or the quinazoline ring or an atom forming the substituent is not included in the number of the ring atoms.
In the present specification, a term “XX to YY carbon atoms” in an expression of “substituted or unsubstituted ZZ group including XX to YY carbon atoms” represents the number of carbon atoms when the ZZ group is unsubstituted. The number of carbon atoms of a substituent when the ZZ group is substituted is not included. Here, “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
In the present specification, a term “XX to YY atoms” in an expression of “substituted or unsubstituted ZZ group including XX to YY atoms” represents the number of atoms when the ZZ group is unsubstituted. The number of atoms of a substituent when the group is substituted is not included. Here, “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
A term “unsubstituted” in the case of “substituted or unsubstituted ZZ group” means that the ZZ group is not substituted by a substituent, and a hydrogen atom is bonded therewith. Alternatively, a term “substituted” in the case of “substituted or unsubstituted ZZ group” means that one or more hydrogen atoms in the ZZ group are substituted by a substituent. Similarly, a term “substituted” in the case of “BB group substituted by an AA group” means that one or more hydrogen atoms in the BB group are substituted by the AA group.
Hereinafter, the substituent described herein will be described.
The number of the ring carbon atoms of the “unsubstituted aryl group” described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified.
The number of the ring carbon atoms of the “unsubstituted heterocyclic group” described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified.
The number of the carbon atoms of the “unsubstituted alkyl group” described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified.
The number of the carbon atoms of the “unsubstituted alkenyl group” described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified.
The number of the carbon atoms of the “unsubstituted alkynyl group” described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified.
The number of the ring carbon atoms of the “unsubstituted cycloalkyl group” described herein is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified.
The number of the ring carbon atoms of the “unsubstituted arylene group” described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified.
The number of the ring atoms of the “unsubstituted divalent heterocyclic group” described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified.
The number of the carbon atoms of the “unsubstituted alkylene group” described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified.
Specific examples (specific example group G1) of the “substituted or unsubstituted aryl group” described herein include an unsubstituted aryl group and a substituted aryl group described below. (Here, a term “unsubstituted aryl group” refers to a case where the “substituted or unsubstituted aryl group” is the “unsubstituted aryl group,” and a term “substituted aryl group” refers to a case where the “substituted or unsubstituted aryl group” is the “substituted aryl group”. Hereinafter, a case of merely “aryl group” includes both the “unsubstituted aryl group” and the “substituted aryl group”.
The “substituted aryl group” refers to a case where the “unsubstituted aryl group” has a substituent, and specific examples thereof include a group in which the “unsubstituted aryl group” has the substituent, and a substituted aryl group described below. It should be noted that examples of the “unsubstituted aryl group” and examples of the “substituted aryl group” listed herein are only one example, and the “substituted aryl group” described herein also includes a group in which a group in which “unsubstituted aryl group” has a substituent or the like further has a substituent, and a group in which “substituted aryl group” further has a substituent.
An unsubstituted aryl group:
a phenyl group,
a p-biphenyl group,
a m-biphenyl group,
an o-biphenyl group,
a p-terphenyl-4-yl group,
a p-terphenyl-3-yl group,
a p-terphenyl-2-yl group,
a m-terphenyl-4-yl group,
a m-terphenyl-3-yl group,
a m-terphenyl-2-yl group,
an o-terphenyl-4-yl group,
an o-terphenyl-3-yl group,
an o-terphenyl-2-yl group,
a 1-naphthyl group,
a 2-naphthyl group,
an anthryl group,
a benzanthryl group,
a phenanthryl group,
a benzophenanthryl group,
a phenalenyl group,
a pyrenyl group,
a chrysenyl group,
a benzochrysenyl group,
a triphenylenyl group,
a benzotriphenylenyl group,
a tetracenyl group,
a pentacenyl group,
a fluorenyl group,
a 9,9′-spirobifluorenyl group,
a benzofluorenyl group,
a dibenzofluorenyl group,
a fluoranethenyl group,
a benzofluoranethenyl group, and
a perylenyl group.
A substituted aryl group:
an o-tolyl group,
a m-tolyl group,
a p-tolyl group,
a p-xylyl group,
a m-xylyl group,
an o-xylyl group,
a p-isopropyl phenyl group,
a m-isopropyl phenyl group,
an o-isopropyl phenyl group,
a p-t-butylphenyl group,
a m-t-butylphenyl group,
an o-t-butylphenyl group,
a 3,4,5-trimethylphenyl group,
a 9,9-dimethylfluorenyl group,
a 9,9-diphenylfluorenyl group
a 9,9-di(4-methylphenyl)fluorenyl group,
a 9,9-di(4-isopropylphenyl)fluorenyl group,
a 9,9-di(4-t-butylphenyl)fluorenyl group,
a cyanophenyl group,
a triphenylsilylphenyl group,
a trimethylsilylphenyl group,
a phenylnaphthyl group, and
a naphthylphenyl group.
The “heterocyclic group” described herein is a ring group having at least one hetero atom in the ring atom. Specific examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom and a boron atom.
The “heterocyclic group” described herein may be a monocyclic group, or a fused ring group.
The “heterocyclic group” described herein may be an aromatic heterocyclic group, or an aliphatic heterocyclic group.
Specific examples (specific example group G2) of the “substituted or unsubstituted heterocyclic group” include an unsubstituted heterocyclic group and a substituted heterocyclic group described below. (Here, the unsubstituted heterocyclic group refers to a case where the “substituted or unsubstituted heterocyclic group” is the “unsubstituted heterocyclic group,” and the substituted heterocyclic group refers to a case where the “substituted or unsubstituted heterocyclic group” is the “substituted heterocyclic group”. Hereinafter, the case of merely “heterocyclic group” includes both the “unsubstituted heterocyclic group” and the “substituted heterocyclic group”.
The “substituted heterocyclic group” refers to a case where the “unsubstituted heterocyclic group” has a substituent, and specific examples thereof include a group in which the “unsubstituted heterocyclic group” has a substituent, and a substituted heterocyclic group described below. It should be noted that examples of the “unsubstituted heterocyclic group” and examples of the “substituted heterocyclic group” listed herein are merely one example, and the “substituted heterocyclic group” described herein also includes a group in which “unsubstituted heterocyclic group” which has a substituent or the like further has a substituent, and a group in which “substituted heterocyclic group” further has a substituent.
An unsubstituted heterocyclic group having a nitrogen atom:
a pyrrolyl group,
an imidazolyl group,
a pyrazolyl group,
a triazolyl group,
a tetrazolyl group,
an oxazolyl group,
an isoxazolyl group,
an oxadiazolyl group,
a thiazolyl group,
an isothiazolyl group,
a thiadiazolyl group,
a pyridyl group,
a pyridazinyl group,
a pyrimidinyl group,
a pyrazinyl group,
a triazinyl group,
an indolyl group,
an isoindolyl group,
an indolizinyl group,
a quinolizinyl group,
a quinolyl group,
an isoquinolyl group,
a cinnolyl group,
a phthalazinyl group,
a quinazolinyl group,
a quinoxalinyl group,
a benzimidazolyl group,
an indazolyl group,
a phenanthrolinyl group,
a phenanthridinyl group
an acridinyl group,
a phenazinyl group,
a carbazolyl group,
a benzocarbazolyl group,
a morpholino group,
a phenoxazinyl group,
a phenothiazinyl group,
an azacarbazolyl group, and
a diazacarbazolyl group.
An unsubstituted heterocyclic group having an oxygen atom:
a furyl group,
an oxazolyl group,
an isoxazolyl group,
an oxadiazolyl group,
a xanthenyl group,
a benzofuranyl group,
an isobenzofuranyl group,
a dibenzofuranyl group,
a naphthobenzofuranyl group,
a benzooxazolyl group,
a benzisoxazolyl group,
a phenoxazinyl group,
a morpholino group,
a dinaphthofuranyl group,
an azadibenzofuranyl group,
a diazadibenzofuranyl group,
an azanaphthobenzofuranyl group, and
a diazanaphthobenzofuranyl group.
An unsubstituted heterocyclic group having a sulfur atom:
a thienyl group,
a thiazolyl group,
an isothiazolyl group,
a thiadiazolyl group,
a benzothiophenyl group,
an isobenzothiophenyl group,
a dibenzothiophenyl group,
a naphthobenzothiophenyl group,
a benzothiazolyl group,
a benzisothiazolyl group,
a phenothiazinyl group,
a dinaphthothiophenyl group,
an azadibenzothiophenyl group,
a diazadibenzothiophenyl group,
an azanaphthobenzothiophenyl group, and
a diazanaphthobenzothiophenyl group.
A substituted heterocyclic group having a nitrogen atom:
a (9-phenyl)carbazolyl group,
a (9-biphenylyl)carbazolyl group,
a (9-phenyl)phenylcarbazolyl group,
a (9-naphthyl)carbazolyl group,
a diphenylcarbazol-9-yl group,
a phenylcarbazol-9-yl group,
a methylbenzimidazolyl group,
an ethylbenzimidazolyl group,
a phenyltriazinyl group,
a biphenylyltriazinyl group,
a diphenyltriazinyl group,
a phenylquinazolinyl group, and
a biphenylylquinazolinyl group.
A substituted heterocyclic group having an oxygen atom:
a phenyldibenzofuranyl group,
a methyldibenzofuranyl group,
a t-butyldibenzofuranyl group, and
a monovalent residue of spiro[9H-xanthene-9,9′-[9H]fluorene].
A substituted heterocyclic group having a sulfur atom:
a phenyldibenzothiophenyl group,
a methyldibenzothiophenyl group,
a t-butyldibenzothiophenyl group, and
a monovalent residue of spiro[9H-thioxantene-9,9′-[9H]fluorene].
A monovalent group derived from the following unsubstituted heterocyclic ring containing at least one of a nitrogen atom, an oxygen atom and a sulfur atom, and a group in which a monovalent group derived from the following unsubstituted heterocyclic ring has a substituent:
In the formulas (XY-1) to (XY-18), X_Aand Y_Aare independently an oxygen atom, a sulfur atom, NH or CH₂. However, at least one of X_Aand Y_Ais an oxygen atom, a sulfur atom or NH.
The heterocyclic ring represented by the formulas (XY-1) to (XY-18) becomes a monovalent heterocyclic group having a bond at an arbitrary position.
An expression “the monovalent group formed from the unsubstituted heterocyclic ring represented by the formulas (XY-1) to (XY-18) has a substituent” refers to a case where the hydrogen atom bonded with the carbon atom of a skeleton of the formulas is substituted by a substituent, or a state in which X_Aor Y_Ais NH or CH₂, and the hydrogen atom in the NH or CH₂is replaced with a substituent.
Specific examples (specific example group G3) of the “substituted or unsubstituted alkyl group” include an unsubstituted alkyl group and a substituted alkyl group described below. (Here, the unsubstituted alkyl group refers to a case where the “substituted or unsubstituted alkyl group” is the “unsubstituted alkyl group,” and the substituted alkyl group refers to a case where the “substituted or unsubstituted alkyl group” is the “substituted alkyl group”). Hereinafter, the case of merely “alkyl group” includes both the “unsubstituted alkyl group” and the “substituted alkyl group”.
The “substituted alkyl group” refers to a case where the “unsubstituted alkyl group” has a substituent, and specific examples thereof include a group in which the “unsubstituted alkyl group” has a substituent, and a substituted alkyl group described below. It should be noted that examples of the “unsubstituted alkyl group” and examples of the “substituted alkyl group” listed herein are merely one example, and the “substituted alkyl group” described herein also includes a group and the like in which “unsubstituted alkyl group” has a substituent further has a substituent, a group in which “substituted alkyl group” further has a substituent.
An unsubstituted alkyl group:
a methyl group,
an ethyl group,
a n-propyl group,
an isopropyl group,
a n-butyl group,
an isobutyl group,
a s-butyl group, and
a t-butyl group.
A substituted alkyl group:
a heptafluoropropyl group (including an isomer),
a pentafluoroethyl group,
a 2,2,2-trifluoroethyl group, and
a trifluoromethyl group.
Specific examples (specific example group G4) of the “substituted or unsubstituted alkenyl group” include an unsubstituted alkenyl group and a substituted alkenyl group described below. (Here, the unsubstituted alkenyl group refers to a case where the “substituted or unsubstituted alkenyl group” is the “unsubstituted alkenyl group,” and the substituted alkenyl group refers to a case where the “substituted or unsubstituted alkenyl group” is the “substituted alkenyl group”). Hereinafter, the case of merely “alkenyl group” includes both the “unsubstituted alkenyl group” and the “substituted alkenyl group”.
The “substituted alkenyl group” refers to a case where the “unsubstituted alkenyl group” has a substituent, and specific examples thereof include a group in which the “unsubstituted alkenyl group” has a substituent, and a substituted alkenyl group described below. It should be noted that examples of the “unsubstituted alkenyl group” and examples of the “substituted alkenyl group” listed herein are merely one example, and the “substituted alkenyl group” described herein also includes a group and the like in which “unsubstituted alkenyl group” has a substituent further has a substituent, a group in which “substituted alkenyl group” further has a substituent.
An unsubstituted alkenyl group and a substituted alkenyl group:
a vinyl group,
an allyl group,
a 1-butenyl group,
a 2-butenyl group,
a 3-butenyl group,
a 1,3-butanedienyl group,
a 1-methylvinyl group,
a 1-methylallyl group,
a 1,1-dimethylallyl group,
a 2-methylallyl group, and
a 1,2-dimethylallyl group.
Specific examples (specific example group G5) of the “substituted or unsubstituted alkynyl group” include an unsubstituted alkynyl group described below. (Here, the unsubstituted alkynyl group refers to a case where the “substituted or unsubstituted alkynyl group” is the “unsubstituted alkynyl group”). Hereinafter, a case of merely “alkynyl group” includes both the “unsubstituted alkynyl group” and the “substituted alkynyl group”.
The “substituted alkynyl group” refers to a case where the “unsubstituted alkynyl group” has a substituent, and specific examples thereof include a group in which the “unsubstituted alkynyl group” described below has a substituent.
An unsubstituted alkynyl group:
an ethynyl group.
Specific examples (specific example group G6) of the “substituted or unsubstituted cycloalkyl group” described herein include an unsubstituted cycloalkyl group and a substituted cycloalkyl group described below. (Here, the unsubstituted cycloalkyl group refers to a case where the “substituted or unsubstituted cycloalkyl group” is the “unsubstituted cycloalkyl group,” and the substituted cycloalkyl group refers to a case where the “substituted or unsubstituted cycloalkyl group” is the “substituted cycloalkyl group”). Hereinafter, a case of merely “cycloalkyl group” includes both the “unsubstituted cycloalkyl group” and the “substituted cycloalkyl group”.
The “substituted cycloalkyl group” refers to a case where the “unsubstituted cycloalkyl group” a the substituent, and specific examples thereof include a group in which the “unsubstituted cycloalkyl group” has a substituent, and a substituted cycloalkyl group described below. It should be noted that examples of the “unsubstituted cycloalkyl group” and examples of the “substituted cycloalkyl group” listed herein are merely one example, and the “substituted cycloalkyl group” described herein also includes a group and the like in which “unsubstituted cycloalkyl group” has a substituent further has a substituent, a group in which “substituted cycloalkyl group” further has a substituent
An unsubstituted aliphatic ring group:
a cyclopropyl group,
a cyclobutyl group,
a cyclopentyl group,
a cyclohexyl group,
a 1-adamantyl group,
a 2-adamantyl group,
a 1-norbomyl group, and
a 2-norbomyl group.
A substituted cycloalkyl group:
a 4-methylcyclohexyl group.
Specific examples (specific example group G7) of the group represented by —Si(R₉₀₁)(R₉₀₂)(R₉₀₃) described herein include

—Si(G1)(G1)(G1),

—Si(G1)(G2)(G2),

—Si(G1)(G1)(G2),

—Si(G2)(G2)(G2),

—Si(G5)(G5)(G5) and

—Si(G6)(G6)(G6).

In which,
G1 is the “aryl group” described in the specific example group G1.
G2 is the “heterocyclic group” described in the specific example group G2.
G3 is the “alkyl group” described in the specific example group G3.
G6 is the “cycloalkyl group” described in the specific example group G6.
Specific examples (specific example group G8) of the group represented by —O—(R₉₀₄) described herein include

—O(G1),

—O(G2),

—O(G3) and

—O(G6).

In which,
G1 is the “aryl group” described in the specific example group G1.
G2 is the “heterocyclic group” described in the specific example group G2.
G3 is the “alkyl group” described in the specific example group G3.
G6 is the “cycloalkyl group” described in the specific example group G6.
Specific examples (specific example group G9) of the group represented by —S—(R₉₀₅) described herein include

—S(G1),

—S(G2),

—S(G3) and

—S(G6).

In which,
G1 is the “aryl group” described in the specific example group G1.
G2 is the “heterocyclic group” described in the specific example group G2.
G3 is the “alkyl group” described in the specific example group G3.
G6 is the “cycloalkyl group” described in the specific example group G6.
Specific examples (specific example group G10) of the group represented by —N(R₉₀₆)(R₉₀₇) described herein include

—N(G1)(G1),

—N(G2)(G2),

—N(G1)(G2),

—N(G3)(G3) and

—N(G6) (G6).

In which,
G1 is the “aryl group” described in the specific example group G1.
G2 is the “heterocyclic group” described in the specific example group G2.
G3 is the “alkyl group” described in the specific example group G3.
G6 is the “cycloalkyl group” described in the specific example group G6.
Specific examples (specific example group G11) of the “halogen atom” described herein include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
The “alkoxy group” described herein include a group represented by —O(G3), where G3, for examples is the “alkyl group” described in the specific example group G3. The number of carbon atoms of the “unsubstituted alkoxy group” are 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified.
The “alkylthio group” described herein include a group represented by —S(G3), where G3, for examples is the “alkyl group” described in the specific example group G3. The number of carbon atoms of the “unsubstituted alkylthio group” are 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified.
The “aryloxy group” described herein include a group represented by —O(G1), where G1, for examples is the “aryl group” described in the specific example group G1. The number of ring carbon atoms of the “unsubstituted aryloxy group” are 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified.
The “arylthio group” described herein include a group represented by —S(G1), where G1, for examples is the “aryl group” described in the specific example group G1. The number of ring carbon atoms of the “unsubstituted arylthio group” are 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified.
The “aralkyl group” described herein include a group represented by -(G3)-(G1), where G3, for examples is the “alkyl group” described in the specific example group G3, and G1, for examples is the “aryl group” described in the specific example group G1. Accordingly, the “aralkyl group” is one aspect of the “substituted alkyl group” substituted by the “aryl group”. The number of carbon atoms of the “unsubstituted aralkyl group,” which is the “unsubstituted alkyl group” substituted by the “unsubstituted aryl group,” are 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified.
Specific example of the “aralkyl group” include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butyl group, an α-naphthylmethyl group, a 1-α-naphthylethyl group, a 2-α-naphthylethyl group, a 1-α-naphthylisopropyl group, a 2-α-naphthylisopropyl group, a p-naphthylmethyl group, a 1-β-naphthylethyl group, a 2-β-naphthylethyl group, a 1-β-naphthylisopropyl group, and a 2-β-naphthylisopropyl group.
The substituted or unsubstituted aryl group described herein is, unless otherwise specified, preferably a phenyl group, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9′-spirobifluorenyl group, a 9,9-diphenylfluorenyl group, or the like.
The substituted or unsubstituted heterocyclic group described herein is, unless otherwise specified, preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group, a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an azadibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group, a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazinyl group, a biphenylyltriazinyl group, diphenyltriazinyl group, a phenyldibenzofuranyl group, a phenyldibenzothiophenyl group, or the like.
The substituted or unsubstituted alkyl group described herein is, unless otherwise specified, preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, or the like.
The “substituted or unsubstituted arylene group” descried herein refers to a group in which the above-described “aryl group” is converted into divalence, unless otherwise specified. Specific examples (specific example group G12) of the “substituted or unsubstituted arylene group” include a group in which the “aryl group” described in the specific example group G1 is converted into divalence.
Specific examples (specific example group G13) of the “substituted or unsubstituted divalent heterocyclic group” include a group in which the “heterocyclic group” described in the specific example group G2 is converted into divalence.
Specific examples (specific example group G14) of the “substituted or unsubstituted alkylene group” include a group in which the “alkyl group” described in the specific example group G3 is converted into divalence.
The substituted or unsubstituted arylene group described herein is any group described below, unless otherwise specified.
In the formulas (XY-20) to (XY-29), R₉₀₈is a substituent.
Then, m901 is an integer of 0 to 4, and when m901 is two or more, a plurality of R₉₀₈may be the same with or different from each other.
In the formulas (XY-30) to (XY-40), R₉₀₉is independently a hydrogen atom or a substituent. Two of R₉₀₉may be bonded with each other through a single bond to form a ring.
In the formulas (XY-41) to (XY-46), R₉₁₀is a substituent.
Then, m902 is an integer of 0 to 6. When m902 is two or more, a plurality of R₉₁₀may be the same or different.
The substituted or unsubstituted divalent heterocyclic group described herein is preferably any group described below, unless otherwise specified.
In the formulas (XY-50) to (XY-64), R₉₁₁is a hydrogen atom or a substituent.
In the formulas (XY-65) to (XY-75), X_Bis an oxygen atom or a sulfur atom.
An organic electroluminescence device according to the first aspect of the invention (hereinafter, referred to as the organic EL device of the first aspect in several cases) is characterized in that an organic electroluminescence device comprises:
an anode, an emitting layer, a first electron-transporting layer, a second electron-transporting layer and a cathode in this order,
the second electron-transporting layer comprises a compound represented by the following formula (1):
and the emitting layer comprises a compound represented by the following formula (10).
Each substituent in the above formulas (1) and (10) will be described later.
In the organic EL device of the first aspect, a high-performance organic electroluminescence device can be obtained by comprising an anode, an emitting layer, a first electron-transporting layer, a second electron-transporting layer and a cathode in this order, the second electron-transporting layer comprises a compound represented by the above formula (1), and the emitting layer comprises a compound represented by the above formula (10). In particular, it is possible to obtain an organic electroluminescence device having a high luminous efficiency, an organic electroluminescence device having a long lifetime, and an organic electroluminescence device having a high luminous efficiency and a long lifetime. It is presumed that this effect is obtained by improving the carrier balance factor by the configuration.
The first electron-transporting layer may or may not be directly adjacent to the light emitting layer. However, the first electron-transporting layer is preferably immediately adjacent to the emitting layer.
The first electron-transporting layer and the second electron-transporting layer may or may not be directly adjacent to each other. However, the first electron-transporting layer and the second electron-transporting layer are preferably immediately adjacent to each other.
When the emitting layer and the first electron-transporting layer or the first electron-transporting layer and the second electron-transporting layer are not adjacent to each other, a third electron-transporting layer or the like may be provided between the respective layers.
The second electron-transporting layer may or may not be directly adjacent to the cathode. When the second electron-transporting layer is not adjacent to the cathode, another layer may be provided between the second electron-transporting layer and the cathode. The other layer provided between the second electron-transporting layer and the cathode is preferably an electron-injecting layer. An electron-injecting layer is preferably provided between the second electron-transporting layer and the cathode. The material of the electron-injecting layer will be described later.
It is also preferable that an organic layer is provided between the anode and the emitting layer. The organic layer between the anode and the emitting layer is preferably a hole injection layer, a hole-transporting layer or the like. The materials for the hole injection layer and the hole-transporting layer will be described later.
Next, the compound represented by the formula (1) will be described.
In the formula (1),
L₁is a single bond, or a group selected from the group consisting of
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted biphenylene group,
a substituted or unsubstituted terphenylene group,
a substituted or unsubstituted quarterphenylene group,
a substituted or unsubstituted fused arylene group including 10 to 30 ring carbon atoms, and
a group in that 1 to 3 substituted or unsubstituted phenylene groups and 1 to 3 substituted or unsubstituted fused arylene groups including 10 to 30 ring carbon atoms are linked via a single bond;
A_r1and A_r2are independently a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 30 ring atoms and no nitrogen atom;
X₁to X₃are independently N or CR₁;
provided that two or more of X₁to X₃are N; R₁does not form a ring by bonding with adjacent L₁, Ar₁or Ar₂;
R₁'s are independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 20 carbon atoms, a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 30 ring atoms;
HA is a monovalent group represented by the following formula (HA).
In the formula (HA),
Y₁to Y₈are independently N or CR₂. R₂'s are independently a hydrogen atom or a substituent;
When plural R₂'s are present, the plural R₂'s may be the same or different. Plural R₂'s substituting on adjacent carbon atoms may form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other;
provided that one of Y₁to Y₈and atoms constituting the substituted or unsubstituted, saturated or unsaturated ring formed by bonding R₂'s with each other is a carbon atom bonded with L₁;
X₄is O or S;
In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (2):
In the formula (2), L₁, A_r1, Ar₂and X₁to X₄are as defined in the formula (1);

- one of Y_1ato Y_4ais a carbon atom bonded with L₁;

Y_5ato Y_8aand Y_1ato Y_4awhich is not the carbon atom bonded with L₁are independently N or CR₂; R₂'s are independently a hydrogen atom or a substituent;
when plural R₂'s are present, the plural R₂'s may be the same or different; plural R₂'s substituting on adjacent carbon atoms may form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other.
In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (2A):
In the formula (2A), X₄, L₁, Ar₁, Ar₂and X₁to X₃are as defined in the formula (1);
one of Y_1bto Y_4bis a carbon atom bonded with L₁;
Y_5bto Y_8band Y_1bto Y_4bwhich is not the carbon atom bonded with L₁are independently N or CR₃; and R₃'s are independently a hydrogen atom or a substituent;
when plural R₃'s are present, the plural R₃'s may be the same or different; and plural R₃'s substituting on adjacent carbon atoms do not form a ring.
In one embodiment, the compound represented by the formula (1) is selected from the group consisting of compounds represented by any of the following formulas (3-1) to (3-12):
In the formulas (3-1) to (3-12), L₁, Ar₁, Ar₂, X₁to X₄and Y₁to Y₈are as defined in the formula (1);
R₄'s are independently a substituent;
n1's are an integer of 0 to 4, n2's are an integer of 0 to 3; when n1 and n2 are two or more, plural R₄'s may be the same or different; plural R₄'s substituting on adjacent carbon atoms may form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other.
Specific examples of the unsubstituted arylene group in the formula (1) in the case where L₁is an arylene group including 16 to 30 ring carbon atoms, wherein 1 to 3 substituted or unsubstituted phenylene groups and 1 to 3 arylene groups composed of substituted or unsubstituted fused rings are connected via a single bond, include a group in combination with a phenylene group and a naphthylene group which are divalent groups consisting of one or more monocycles and one or more fused rings as shown below
In one embodiment, L₁is a single bond, or a group selected from the group consisting of
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted biphenylene group,
a substituted or unsubstituted terphenylene group,
a substituted or unsubstituted quaterphenylene group,
a substituted or unsubstituted arylene group composed of a fused ring including 10 to 30 ring carbon atoms;
a group in which 1 to 3 substituted or unsubstituted phenylene groups and 1 to 3 arylene groups composed of substituted or unsubstituted fused rings are connected via a single bond.
When L₁has a substituent, the substituent is a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 30 ring atoms, except for a carbazolyl group.
In one embodiment, L₁is a substituted or unsubstituted arylene group including 6 to 12 ring carbon atoms, and is specifically a divalent group represented by any of the following formulas (aa1) to (aa3).
In formulas (aa1) to (aa3),
R₂is a substituent;

- n1's are an integer of 0 to 4 and n2 is an integer of 0 to 6.

When n1 and n2 are two or more, plural R₂'s may be the same or different. Plural R₂'s substituting on adjacent carbon atoms do not form a ring by bonding with each other.
In the above formulas (aa1) to (aa3), R₂is bonded to any position capable of bonding on the benzene ring or the naphthalene ring. The same applies hereafter.
In one embodiment, L₁is a single bond or the unsubstituted arylene group including 6 to 30 ring carbon atoms.
In one embodiment, L₁is a single bond or an unsubstituted arylene group including 6 to 12 ring carbon atoms.
In one embodiment, particularly preferable examples of the substituent when L₁has a substituent include a phenyl group and an azine group such as a pyridinyl group, a pyrimidinyl group and a triazinyl group.
In one embodiment, Ar₁and Ar₂are a substituted or unsubstituted monovalent heterocyclic group including 5 to 30 ring atoms, except for a substituted or unsubstituted carbazolyl group, preferably a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and azine groups such as a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, and a substituted or unsubstituted triazinyl group.
In one embodiment, L₁is a single bond, or a group selected from the group consisting of divalent groups represented by any of the following formulas (a1) to (a3).
In one embodiment, L₁is a single bond, or a group selected from the group consisting of divalent groups represented by any of the following formulas (a1-1) to (a1-3).
The above formulas (a2) and (a3) are shown more specifically by formulas (a2-1) to (a2-9) and formulas (a3-1) to (a3-6).
In one embodiment, Ar₁and Ar₂are independently a substituted or unsubstituted aryl group including 6 to 12 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 12 ring atoms and no nitrogen atom.
In one embodiment, Ar₁and Ar₂are independently a group selected from the group consisting of monovalent groups represented by any of the following formulas (b1) to (b3).
In the formulas (b1) to (b3),
R₅'s are independently a substituent,
p's are an integer of 0 to 5,
q is an integer of 0 to 7,
m is an integer of 0 to 4.
When p, q or m is two or more, plural R₅'s may be the same or different. When p, q or m is two or more, plural R₅'s do not form a ring by bonding with each other.
In the above formulas (b1) to (b3), R₅is bonded to any position capable of bonding on the benzene ring or the naphthalene ring. The same applies hereafter.
In one embodiment, Ar₁and Ar₂are independently a group selected from the group consisting of monovalent groups represented by any of the following formulas (b1-1), and (b3-1) to (b3-3).
In the formulas (b1-1), and (b3-1) to (b3-3),
R₅'s are independently a substituent,
p's are an integer of 0 to 5,
m's are an integer of 0 to 4.
When p or m is two or more, plural R₅'s may be the same or different. When p or m is two or more, plural R₅'s do not form a ring by bonding with each other.
In one embodiment, X₁to X₃are N.
In one embodiment, the compound represented by the formula (1) is selected from the group consisting of compounds represented by any of the following formulas (2A-1) to (2A-4).
In the formulas (2A-1) to (2A-4), L₁and X₁to X₄are as defined in the formula (1).
Y_1bto Y_8bare independently N or CR₃. R₃'s are independently a hydrogen atom or a substituent.
When plural R₃'s are present, the plural R₃'s may be the same or different. Plural R₃'s substituting on adjacent carbon atoms do not form a ring by bonding with each other.
Ar_1aand Ar_2aare independently a substituted or unsubstituted aryl group including 6 to 12 ring carbon atoms.
In one embodiment, the compound represented by the formula (1) is selected from the group consisting of compounds represented by any of the following formulas (2A-1-1) to (2A-4-1).
In the formulas (2A-1-1) to (2A-4-1), X₄is as defined in the formula (1).
Y_1bto Y_8bare independently N or CR₃. R₃'s are independently a hydrogen atom or a substituent.
When plural R₃'s are present, the plural R₃'s may be the same or different. Plural R₃'s substituting on adjacent carbon atoms do not form a ring by bonding with each other.
L_1bis a single bond or a group selected from the group consisting of divalent groups represented by any of the following formulas (a1) to (a3).
Ar_1band Ar_2bare independently a group selected from the group consisting of monovalent groups represented by any of the following formulas (b1) to (b3):
wherein in the formulas (b1) to (b3),
R₅'s are independently a substituent,
p's are an integer of 0 to 5,
q is an integer of 0 to 7,
m is an integer of 0 to 4;
when p, q or m is two or more, plural R₅'s may be the same or different, and
when p, q or m is two or more, plural R₅'s do not form a ring by bonding with each other.
In one embodiment, the compound represented by the formula (1) is selected from the group consisting of compounds represented by any of the following formulas (2A-1-2) to (2A-4-2).
In the formulas (2A-1-2) to (2A-4-2), X₄is as defined in the formula (1).
Y_1bto Y_8bare independently N or CR₃. R₃'s are independently a hydrogen atom or a substituent.
When plural R₃'s are present, the plural R₃'s may be the same or different. Plural R₃'s substituting on adjacent carbon atoms do not form a ring by bonding with each other.
L_1cis a single bond or a group selected from the group consisting of divalent groups represented by any of the following formulas (a1-1) to (a1-3).
Hereinafter, the formulas (a2) and (a3) are more specifically represented by any of the following formulas (a2-1) to (a2-9) and formulas (a3-1) to (a3-6).
Ar_1aand Ar_2care independently a group selected from the group consisting of monovalent groups represented by any of the following formulas (b1-1), and (b3-1) to (b3-3):
wherein in the formulas (b1-1), and (b3-1) to (b3-3),
R₅'s are independently a substituent,
p's are an integer of 0 to 5,
m's are an integer of 0 to 4;
when p or m is two or more, plural R₅'s may be the same or different, and
when p or m is two or more, plural R₅'s do not form a ring by bonding with each other.
In one embodiment, the compound represented by the formula (1) is selected from the group consisting of compounds represented by any of the following formulas (3-1-1) to (3-6-1).
In the formulas (3-1-1) to (3-6-1), X₁to X₄and Y₁to Y₈are as defined in the formula (1).
R₄'s are independently a substituent.
n1's are an integer of 0 to 4. When n1 is 2 to 4, plural R₄'s may be the same or different. Plural R₄'s substituting on adjacent carbon atoms may form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other.
L_1ais a single bond or an unsubstituted arylene group including 6 to 12 ring carbon atoms.
Ar_1aand Ar_2aare independently a substituted or unsubstituted aryl group including 6 to 12 ring carbon atoms.
In one embodiment, the compound represented by the formula (1) is selected from the group consisting of compounds represented by any of the following formulas (3-1-2) to (3-6-2).
In the formulas (3-1-2) to (3-6-2), X₄and Y₁to Y₈are as defined in the formula (1).
R₄'s are independently a substituent.
n1's are an integer of 0 to 4. When n1 is 2 to 4, plural R₄'s may be the same or different. Plural R₄'s substituting on adjacent carbon atoms may form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other.
L_1bis a single bond or a group selected from the group consisting of divalent groups represented by any of the following formulas (a1) to (a3).
Ar_1band Ar_2bare independently a group selected from the group consisting of monovalent groups represented by any of the following formulas (b1) to (b3):
wherein in the formulas (b1) to (b3),
R₅'s are independently a substituent,
p's are an integer of 0 to 5,
q is an integer of 0 to 7,
m is an integer of 0 to 4;
when p, q or m is two or more, plural R₅'s may be the same or different, and
when p, q or m is two or more, plural R₅'s do not form a ring by bonding with each other.
In one embodiment, the compound represented by the formula (1) is selected from the group consisting of compounds represented by any of the following formulas (3-1-3) to (3-6-3).
In the formulas (3-1-3) to (3-6-3), X₄and Y₁to Y₈are as defined in the formula (1).
R₄'s are independently a substituent.
n1's are an integer of 0 to 4. When n1 is 2 to 4, plural R₄'s may be the same or different. Plural R₄'s substituting on adjacent carbon atoms may form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other.
L_1cis a single bond or a group selected from the group consisting of divalent groups represented by any of the following formulas (a1-1) to (a1-3).
Ar_1cand Ar_2care independently a group selected from the group consisting of monovalent groups represented by any of the following formulas (b1-1), and (b3-1) to (b3-3):
wherein in the formulas (b1-1), and (b3-1) to (b3-3),
R₅'s are independently a substituent,
p's are an integer of 0 to 5,
m's are an integer of 0 to 4;
when p or m is two or more, plural R₅'s may be the same or different, and
when p or m is two or more, plural R₅'s do not form a ring by bonding with each other.
In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (4):
wherein in the formula (4), X₁to X₄, Y₁to Y₈and L₁are as defined in the formula (1);
R₆'s are independently a halogen atom, a cyano group, a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 20 carbon atoms, a substituted or unsubstituted aryl group including 6 to 12 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 30 ring atoms;
provided that when R₆is the monovalent heterocyclic group, R₆is a monovalent heterocyclic group other than a substituted or unsubstituted carbazolyl group;
r is an integer of 0 to 5; when r is 2 to 5, plural R₆'s may be the same or different, and when plural R₆'s are present, plural R₆'s do not form a ring by bonding with each other.
In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (5):
In the formula (5), X₁to X₄are as defined in the formula (1).
Ar_1dand Ar_2dare independently a substituted or unsubstituted aryl group including 6 to 12 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 12 ring atoms.
One of Y_1dto Y_4dis a carbon atom bonded with L_1a.
Y_5dto Y_8d, and Y_1dto Y_4dwhich are not the carbon atom bonded with L_1dare independently N or CR_2a. R_2a's are independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 12 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 12 ring atoms.
When plural R_2a's are present, the plural R_2a's may be the same or different. Plural R_2a's substituting on adjacent carbon atoms may form a substituted or unsubstituted, saturated or unsaturated ring.
L_1dis a single bond or an unsubstituted arylene group including 6 to 12 ring carbon atoms.
In one embodiment, the monovalent group represented by the formula (HA) in the formula (1):
wherein in the formula, Y₁to Y₈and X₄are as defined in the formula (1), is a group selected from the group consisting of a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzofuropyridinyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzothienopyridinyl group, a substituted or unsubstituted benzothienoquinolyl group, and a substituted or unsubstituted benzofuroquinolyl group.
In one embodiment, the monovalent group represented by the formula (HA) in the formula (1) is a group selected from the following groups.
In the formulas, X₄and Y₄are as defined in the formula (1).
The substituent in the case of “substituted or unsubstituted” and the substituent which is R₂to R₆in the formula (1) are selected from the group consisting of
an alkyl group including 1 to 50 carbon atoms,
an alkenyl group including 2 to 50 carbon atoms,
an alkynyl group including 2 to 50 carbon atoms,
a cycloalkyl group including 3 to 50 carbon atoms,
an alkoxy group including 1 to 50 carbon atoms,
an alkylthio group including 1 to 50 carbon atoms,
an aryloxy group including 6 to 50 ring carbon atoms,
an arylthio group including 6 to 50 ring carbon atoms,
an aralkyl group including 7 to 50 carbon atoms,
—Si(R₄₁)(R₄₂)(R₄₃),

—C(═O)R₄₄,

—COOR₄₅,

—S(═O)₂R₄₆,
—P(═O)(R₄₇)(R₄₈),
—Ge(R₄₉)(R₅₀)(R₅₁),
—N(R₅₂)(R₅₃), a hydroxy group, a halogen atom, a cyano group, a nitro group, an aryl group including 6 to 50 ring carbon atoms, and a heterocyclic group including 5 to 50 ring atoms, except for a carbazolyl group;
R₄₁to R₅₃are independently a hydrogen atom, an alkyl group including 1 to 50 carbon atoms, an aryl group including 6 to 50 ring carbon atoms, or a heterocyclic group including 5 to 50 ring atoms, except for a carbazolyl group, and when two or more of each of R₄₁to R₆₃are present, the two or more of each of R₄₁to R₆₃may be the same or different.
In one embodiment, the substituent in the case of “substituted or unsubstituted” and the substituent which is R₂to R₆in the formula (1) are selected from the group consisting of an alkyl group including 1 to 50 carbon atoms, an aryl group including 6 to 12 ring carbon atoms, and a monovalent heterocyclic group including 5 to 12 ring atoms.
Specific examples of the compound represented by the above formula (1) are described below, but the invention is not limited thereto.
Next, the compound represented by the formula (10) will be described.
In the formula (10),
R₁₁to R₁₈are independently a hydrogen atom,
a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms,
a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms,
a substituted or unsubstituted alkylthio group including 1 to 50 carbon atoms,
a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms,
a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms,
a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms,
—Si(R₁₀₁)(R₁₀₂)(R₁₀₃),

—C(═O)R₁₀₄,

—COOR₁₀₅,

—N(R₁₀₆)(R₁₀₇),
a halogen atom, a cyano group, a nitro group,
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms.
R₁₀₁to R₁₀₇are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms.
When two or more of each of R₁₀₁to R₁₀₇are present, the two or more of each of R₁₀₁to R₁₀₇may be the same or different.
At least one of Ar₁₁and Ar₁₂is a monovalent group represented by the following formula (11);
wherein in the formula (11),
one of R₂₁to R₂₈is bonded with L₁₁or L₁₂; and
R₂₁to R₂₈which are not bonded with L₁₁or L₁₂are independently a hydrogen atom,
a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms,
a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms,
a substituted or unsubstituted alkylthio group including 1 to 50 carbon atoms,
a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms,
a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms,
a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms,
—Si(R₁₀₁)(R₁₀₂)(R₁₀₃),

—C(═O)R₁₀₄,

—COOR₁₀₅,

—N(R₁₀₆)(R₁₀₇),
a halogen atom, a cyano group, a nitro group,
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
R₁₀₁to R₁₀₇are as above:
Ar₁₁or Ar₁₂, which is not the monovalent group represented by the formula (11), is an unsubstituted aryl group including 6 to 50 ring carbon atoms, an aryl group including 6 to 50 ring carbon atoms, which is substituted with an unsubstituted alkyl group including 1 to 50 carbon atoms, or an aryl group including 6 to 50 ring carbon atoms, which is substituted with an unsubstituted aryl group including 6 to 50 ring carbon atoms;
L₁₁and L₁₂are independently a single bond, a substituted or unsubstituted alkylene group including 1 to 50 carbon atoms, a substituted or unsubstituted arylene group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group including 5 to 50 ring atoms.
In one embodiment, the compound represented by the formula (10) is a compound represented by the following formula (10-1):
wherein in the formula (10-1), R₁₁to R₁₈, Ar₁₁, L₁₁, L₁₂, R₂₁, and R₂₃to R₂₈are as defined in the formula (10).
In one embodiment, the compound represented by the formula (10) is a compound represented by the following formula (10-2):
wherein in the formula (10-2), L₁₁is a single bond; R₁₁to R₁₈, Arm L₁₂, and R₂₁to R₂₈are as defined in the formula (10).
In one embodiment, the compound represented by the formula (10) is a compound represented by the following formula (10-3):
wherein in the formula (10-3), Liu is a single bond; R₁₁to R₁₈, Ar₁₁, L₁₂, R₂₁, and R₂₃to R₂₈are as defined in the formula (10).
In one embodiment, in the formulas (10), (10-1), (10-2) and (10-3), R₂₁to R₂₈which are not bonded with L₁₁are a hydrogen atom.
In one embodiment, in the formulas (10), (10-1), (10-2) and (10-3), R₁₁to R₁₈are a hydrogen atom.
In one embodiment, the compound represented by the formula (10) is a compound represented by the following formula (10-4):
wherein in the formula (10-4), L₁₁is a single bond; Ar₁₁and L₁₂are as defined in the formula (1).
In one embodiment, the substituent in the case of “substituted or unsubstituted” in the formulas (10), (10-1), (10-2), (10-3) and (10-4) is selected from the group consisting of an alkyl group including 1 to 50 carbon atoms, an alkenyl group including 2 to 50 carbon atoms, an alkynyl group including 2 to 50 carbon atoms, a cycloalkyl group including 3 to 50 carbon atoms, an alkoxy group including 1 to 50 carbon atoms, an alkylthio group including 1 to 50 carbon atoms, an aryloxy group including 6 to 50 ring carbon atoms, an arylthio group including 6 to 50 ring carbon atoms, an aralkyl group including 7 to 50 carbon atoms, —Si(R₄₁)(R₄₂)(R₄₃), —C(═O)R₄₄, —COOR₄₅, —S(═O)₂R₄₆, —P(═O)(R₄₇)(R₄₈), —Ge(R₄₉)(R₅₀)(R₅₁), —N(R₅₂)(R₅₃), a hydroxy group, a halogen atom, a cyano group, a nitro group, an aryl group including 6 to 50 ring carbon atoms, and a heterocyclic group including 5 to 50 ring atoms;
R₄₁to R₅₃are independently a hydrogen atom, an alkyl group including 1 to 50 carbon atoms, an aryl group including 6 to 50 ring carbon atoms, or a heterocyclic group including 5 to 50 ring atoms, and when two or more of each of R₄₁to R₅₃are present, the two or more of each of R₄₁to R₅₃may be the same or different.
In one embodiment, the substituent in the case of “substituted or unsubstituted” in the formulas (10), (10-1), (10-2), (10-3) and (10-4) is selected from the group consisting of an alkyl group including 1 to 50 carbon atoms, an aryl group including 6 to 50 ring carbon atoms, and a heterocyclic group including 5 to 50 ring atoms.
In one embodiment, the substituent in the case of “substituted or unsubstituted” in the formulas (10), (10-1), (10-2), (10-3) and (10-4) is selected from the group consisting of an alkyl group including 1 to 18 carbon atoms, an aryl group including 6 to 18 ring carbon atoms, and a heterocyclic group including 5 to 18 ring atoms.
Specific examples of the compound represented by the above formula (2) are described below, but the invention is not limited thereto.
In one embodiment, the second electron-transporting layer further comprises one or two or more selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, an alkaline earth metal halide, a rare earth metal oxide, a rare earth metal halide, an alkali metal-containing organic complex, an alkaline earth metal-containing organic complex, and a rare earth metal-containing organic complex. Among the above compounds, an organic complex containing an alkali metal is preferable, and Liq (8-hydroxyquinolinolato-lithium) is particularly preferable.
In one embodiment, the first electron-transporting layer comprises a compound represented by the following formula (30):
wherein in the formula (30),
X₁₁is a nitrogen atom, CH or CR₈₃;
when X₁₁is CR₈₃, the adjacent two among R₈₂to R₈₄may be bonded to each other, to form together with the two ring carbon atoms to which they are bonded, a substituted or unsubstituted aromatic hydrocarbon ring including 10 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring including 5 to 32 ring atoms;
R₈₁, and R₈₂to R₈₄which do not form the ring are independently a group represented by any of the following formulas (31) to (34):
wherein in the formulas (31) to (34),
L₃₁, L₃₃, L₃₆, L₃₈and L₃₉are independently a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 32 ring atoms;
L₃₂, L₃₄and L₃₅are independently a substituted or unsubstituted arylene group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group including 5 to 32 ring atoms;
L₃₇is a substituted or unsubstituted trivalent aromatic hydrocarbon ring group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted trivalent heterocyclic group including 5 to 32 ring atoms.
In one embodiment, the compound represented by the formula (30) is a compound represented by the following formula (30a) or the following formula (30b). That is, X₁₁is N or CH.
In the formula (30a) and (30b), R₈₁, R₈₂and R₈₄are as defined in the formula (30).
In one embodiment, the compound represented by the formula (30) is a compound represented by the following formula (30c). That is, X₁₁is N or CR₈₃.
In the formula (30c), R₈₁to R₈₄are as defined in the formula (30).
The adjacent two among R₈₂to R₈₄are bonded to each other specifically, when R₈₂and R₈₃or R₈₃and R₈₄are bonded to each other.
In one embodiment, when the adjacent two among R₈₂to R₈₄are bonded to each other to form an aromatic hydrocarbon ring including 10 to 30 ring carbon atoms or a heterocyclic ring including 5 to 32 ring atoms, the structure formed by bonding adjacent two among R₈₂to R₈₄to each other is selected from the following group. The following structure may have a substituent.
In the above formula, * indicates the bonding position of R₈₂and R₈₃or R₈₃and R₈₄.
In one embodiment, the structure formed by bonding adjacent two among R₈₂to R₈₄to each other is selected from the following group. The following structure may have a substituent.
In the above formula, * indicates the bonding position of R₈₂and R₈₃or R₈₃and R₈₄.
In one embodiment, for L₃₁to L₃₉in the formulas (31) to (34), the substituted or unsubstituted aryl group, arylene group and trivalent aromatic hydrocarbon ring group is independently, which include 6 to 30 ring carbon atoms, are each a substituted or unsubstituted aryl group, arylene group and trivalent aromatic hydrocarbon ring group, which include 6 to 18 ring carbon atoms.
In the formulas (31) to (34), specific examples of the aromatic hydrocarbon ring including 6 to 30 ring carbon atoms which forms the substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms, the arylene group and the trivalent aromatic hydrocarbon ring group of L₃₁to L₃₉include, for example, benzene, biphenyl, terphenyl (including isomers), quarterphenyl (including isomers), naphthalene, fluorene, acenaphthalene, anthracene, benzoanthracene, aceanthracene, phenanthrene, benzophenanthrene, phenalene, pentacene, picene, pentaphenylene, pyrene, chrysene, benzochrysene, s-indacene, as-indacene, fluoranthene, benzofluoranthene, perylene, triphenylene, benzotriphenylene, spirofluorene and so on. The above rings may have a substituent.
In one embodiment, the aromatic hydrocarbon ring including 6 to 30 ring carbon atoms which forms the substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms, the arylene group and the trivalent aromatic hydrocarbon ring group of L₃₁to L₃₉is selected from the following group. The following rings may have a substituent.
Specific examples of the substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms in L₃₁, L₃₃, L₃₆, L₃₈and L₃₉are a monovalent residue which can be obtained by removing one hydrogen atom from the aromatic hydrocarbon rings mentioned above. The monovalent residue may have a substituent.
In one embodiment, in L₃₁, L₃₃, L₃₆, L₃₈and L₃₉, the substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms is a monovalent residue which is obtained by removing one hydrogen atom from the aromatic hydrocarbon rings selected from the group consisting of a substituted or unsubstituted benzene, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthalene, a substituted or unsubstituted fluorene, a substituted or unsubstituted phenanthrene, a substituted or unsubstituted anthracene, a substituted or unsubstituted triphenyl, a substituted or unsubstituted benzochrysene, a substituted or unsubstituted fluoranthene, a substituted or unsubstituted pyrene, a substituted or unsubstituted spirofluorene, a substituted or unsubstituted 9,9-diphenylfluorene, and a substituted or unsubstituted 9,9-dimethylfluorene. The monovalent residue may have a substituent.
In one embodiment, in L₃₁, L₃₃, L₃₆, L₃₈and L₃₉, the substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms is selected from the following group. The following groups may have a substituent
In L₃₂, L₃₄and L₃₅, specific examples of the substituted or unsubstituted arylene group including 6 to 30 ring carbon atoms include a divalent residue which can be obtained by removing one hydrogen atom from each of two ring carbon atoms of the aromatic hydrocarbon rings mentioned above. The divalent residue may have a substituent.
In one embodiment, in L₃₂, L₃₄and L₃₅, the substituted or unsubstituted arylene group including 6 to 30 ring carbon atoms is a divalent residue which is obtained by removing one hydrogen atom from each of two ring carbon atoms of the aromatic hydrocarbon ring selected from the group consisting of a substituted or unsubstituted benzene, a substituted or unsubstituted naphthalene, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted quarterphenyl, a substituted or unsubstituted 9,9-dimethylfluorene, a substituted or unsubstituted 9,9-diphenylfluorene, a substituted or unsubstituted spirofluorene, and a substituted or unsubstituted anthracene.
In one embodiment, the substituted or unsubstituted arylene group including 6 to 30 ring carbon atoms is selected from the following group. The following divalent groups may have a substituent.
In L₃₇, specific examples of the substituted or unsubstituted trivalent aromatic hydrocarbon ring group including 6 to 30 ring carbon atoms include a trivalent residue which can be obtained by removing one hydrogen atom from each of three ring carbon atoms of the aromatic hydrocarbon rings mentioned above. The trivalent residue may have a substituent.
In one embodiment, in L₃₇, the substituted or unsubstituted trivalent aromatic hydrocarbon ring group including 6 to 30 ring carbon atoms is a trivalent residue which is obtained by removing one hydrogen atom from each of three ring carbon atoms of the aromatic hydrocarbon rings selected from the group consisting of a substituted or unsubstituted benzene, a substituted or unsubstituted naphthalene, and a substituted or unsubstituted anthracene.
In one embodiment, in L₃₇, the substituted or unsubstituted trivalent aromatic hydrocarbon ring group including 6 to 30 ring carbon atoms is a trivalent residue of a substituted or unsubstituted benzene.
In one embodiment, in L₃₇, the substituted or unsubstituted trivalent aromatic hydrocarbon ring group including 6 to 30 ring carbon atoms is a benzene-1,3,5-triyl group. The trivalent group may have a substituent.
In one embodiment, in the formulas (31) to (34), the substituted or unsubstituted monovalent to trivalent heterocyclic group including 5 to 32 ring atoms of L₃₁to L₃₉is a monovalent to trivalent residue which can be obtained by removing one hydrogen atom from each of the 1 to 3 ring atoms of a heterocyclic group including 5 to 32 ring atoms.
In one embodiment, in the formulas (31) to (34), the substituted or unsubstituted monovalent to trivalent heterocyclic group including 5 to 32 ring atoms of L₃₁to L₃₉is a substituted or unsubstituted monovalent to trivalent heterocyclic group including 5 to 18 ring atoms.
In one embodiment, the substituted or unsubstituted monovalent to trivalent heterocyclic group including 5 to 32 ring atoms of L₃₁to L₃₉includes 1 to 5, 1 to 3 or 1 to 2 heteroatoms such as a nitrogen atom, a sulfur atom and an oxygen atom.
In the formulas (31) to (34), specific examples of the substituted or unsubstituted heterocyclic ring including 5 to 32 ring atoms which forms the substituted or unsubstituted monovalent to trivalent heterocyclic group including 5 to 32 ring atoms of L₃₁to L₃₉include, for example, pyrrole, imidazole, imidazoline, pyrazole, triazole, furan, thiophene, thiazole, isothiazole, oxazole, isooxazole, oxadiazole, thiadiazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, bipyrrole, terpyrrole, bithiophene, terthiophene, bipyridine, terpyridine, indole, isoindole, benzofuran, isobenzofuran, benzothiophene, indolizine, quinolidine, quinoline, isoquinoline, cinnoline, phthalazine, quinazoline, quinoxaline, benzimidazole, benzoxazole, benzothiazole, indazole, benzisoxazole, benzisothiazole, benzofuran, dibenzofuran, naphthobenzofuran, benzothiophene, dibenzothiophene, naphthobenzothiophene, carbazole, benzocarbazole, phenanthridine, acridine, phenanthroline, phenazine, phenothiazine, phenoxazine, xanthene and so on. The above heterocyclic ring may have a substituent.
In one embodiment, the substituted or unsubstituted heterocyclic group including 5 to 32 ring atoms which forms the substituted or unsubstituted monovalent to trivalent heterocyclic ring including 5 to 32 ring atoms of L₃₁to L₃₉is selected from the following group. The following rings may have a substituent
Specific examples of the substituted or unsubstituted monovalent heterocyclic group including 5 to 32 ring atoms in L₃₁, L₃₃, L₃₆, L₃₈and L₃₉are a monovalent residue which can be obtained by removing one hydrogen atom from one ring atom of the heterocyclic rings mentioned above. The monovalent residue may have a substituent.
In one embodiment, in L₃₁, L₃₃, L₃₆, L₃₈and L₃₉, the substituted or unsubstituted monovalent heterocyclic group including 5 to 32 ring atoms is a monovalent residue which is obtained by removing one hydrogen atom on a ring atom of the heterocyclic rings selected from the group consisting of a substituted or unsubstituted pyridine, a substituted or unsubstituted pyrazine, a substituted or unsubstituted pyridazine, a substituted or unsubstituted pyrimidine, a substituted or unsubstituted triazine, a substituted or unsubstituted bipyridine, a substituted or unsubstituted carbazole, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted xanthene, a substituted or unsubstituted phenanthroline, and a substituted or unsubstituted quinoline.
In one embodiment, in L₃₁, L₃₃, L₃₆, L₃₈and L₃₉, the substituted or unsubstituted monovalent heterocyclic group including 5 to 32 ring atoms is selected from the following group. The following groups may have a substituent.
In L₃₂, L₃₄and L₃₅, specific examples of the substituted or unsubstituted divalent heterocyclic group including 5 to 32 ring atoms include a divalent residue which can be obtained by removing one hydrogen atom from each of two ring atoms of the heterocyclic rings mentioned above. The divalent residue may have a substituent.
In one embodiment, in L₃₂, L₃₄and L₃₅, the substituted or unsubstituted divalent heterocyclic group including 5 to 32 ring atoms is a divalent residue which is obtained by removing one hydrogen atom from each of two ring atoms of the heterocyclic ring selected from the group consisting of a substituted or unsubstituted a substituted or unsubstituted indole, a substituted or unsubstituted isoindole, a substituted or unsubstituted benzofuran, a substituted or unsubstituted isobenzofuran, a substituted or unsubstituted benzothiophene, a substituted or unsubstituted indolizine, a substituted or unsubstituted quinolidine, a substituted or unsubstituted quinoline, a substituted or unsubstituted isoquinoline, a substituted or unsubstituted cinnoline, a substituted or unsubstituted phthalazine, a substituted or unsubstituted quinazoline, a substituted or unsubstituted quinoxaline, a substituted or unsubstituted benzimidazole, a substituted or unsubstituted benzisothiazole, a substituted or unsubstituted benzofuran, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted naphthobenzofuran, a substituted or unsubstituted benzothiophene, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted naphthobenzothiophene, a substituted or unsubstituted carbazole, a substituted or unsubstituted benzocarbazole, a substituted or unsubstituted phenanthridine, a substituted or unsubstituted acridine, a substituted or unsubstituted phenanthroline, a substituted or unsubstituted phenazine, a substituted or unsubstituted phenothiazine, a substituted or unsubstituted phenoxazine, and a substituted or unsubstituted xanthene.
In one embodiment, in L₃₂, L₃₄and L₃₅, the substituted or unsubstituted divalent heterocyclic group including 5 to 32 ring atoms is a divalent residue which is obtained by removing one hydrogen atom from each of two ring atoms of the heterocyclic ring selected from the group consisting of a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted dibenzothiophene, and a substituted or unsubstituted carbazole.
In one embodiment, in L₃₂, L₃₄and L₃₅, the substituted or unsubstituted divalent heterocyclic group including 5 to 32 ring atoms is a divalent residue which is obtained by removing one hydrogen atom from each of two ring atoms of a substituted or unsubstituted pyridine and a substituted or unsubstituted carbazole.
In L₃₇, specific examples of the substituted or unsubstituted trivalent heterocyclic group including 5 to 32 ring atoms include a trivalent residue which can be obtained by removing one hydrogen atom from each of three ring atoms of the heterocyclic rings mentioned above. The trivalent residue may have a substituent.
In one embodiment, in L₃₇, the substituted or unsubstituted trivalent heterocyclic group including 5 to 32 ring atoms is a trivalent residue which is obtained by removing one hydrogen atom from each of three ring atoms of the heterocyclic ring selected from the group consisting of a substituted or unsubstituted pyridine, a substituted or unsubstituted pyrazine, a substituted or unsubstituted pyridazine, a substituted or unsubstituted pyrimidine, a substituted or unsubstituted triazine, a substituted or unsubstituted quinoline, a substituted or unsubstituted benzofuran and a substituted or unsubstituted benzothiophene.
Specific examples of the compound represented by the above formula (30) are described below, but the invention is not limited thereto.
The organic EL device of the first aspect includes at least an anode/a emitting layer/a first electron-transporting layer/a second electron-transporting layer/a cathode, the emitting layer comprises the compound (10), and the second electron-transporting layer comprises the compound (1).
As far as the emitting layer comprising the compound (10), the first electron-transporting layer, and the second electron-transporting layer comprising the compound (1) are provided, a layer other than these may be provided between the emitting layer and the cathode, or the organic EL device may have one or more layers between the emitting layer and the anode.
FIG. 1 shows a schematic configuration of an embodiment of the organic EL device of the first aspect.
An organic EL device 1 has a substrate 2, an anode 3, an emitting layer 5, and a first electron-transporting layer 7 and a second electron-transporting layer 8 as an organic layer 6 between the emitting layer 5 and the cathode 10.
The organic layer 6 between the cathode 10 and the emitting layer 5 functions as an electron-injecting/transporting layer.
The organic EL device 1 may include the organic layer 4 between the anode 3 and the emitting layer 5. The organic layer 4 functions as a hole-injecting/transporting layer.
Here, “electron-injecting/transporting layer” means “at least one of an electron-injecting layer and an electron-transporting layer”, and “hole-injecting/transporting layer” means “at least one of a hole-injecting layer and a hole-transporting layer”.
Further, an electron blocking layer may be provided on the anode 3 side of the emitting layer 5, and a hole-blocking layer may be provided on the cathode 4 side of the emitting layer 5, respectively.
This makes it possible to confine electrons and holes in the emitting layer 5 and increase the probability of exciton generation in the emitting layer 5.
In FIG. 1, two of the first electron-transporting layer 7 and the second electron-transporting layer 8 are drawn between the cathode 10 and the emitting layer 5, but the organic EL device 1 may have three or more organic layers. When having three or more organic layers, the compound represented by the formula (1) is contained in the organic layer closest to the cathode 10.
A layer other than the organic layer may be provided between the second electron-transporting layer 8 and the cathode 10. Examples of layers other than the organic layer include inorganic layers such as LiF and Yb.
In one embodiment, the organic electroluminescence device includes at least one organic layer between the anode and the emitting layer.
In one embodiment, at least one layer of the organic layer 4 (hole-injecting/transporting layer) between the anode 3 and the emitting layer 5 contains a compound represented by the following formula (20).
In the formula (20),
one or more pairs of adjacent two or more among R₃₁to R₃₈may form a substituted or unsubstituted, saturated or unsaturated ring; R₃₁to R₃₈which do not form the ring is independently a hydrogen atom,
a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms,
a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms,
a substituted or unsubstituted alkylthio group including 1 to 50 carbon atoms,
a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms,
a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms,
a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms,
—Si(R₂₀₁)(R₂₀₂)(R₂₀₃),

—C(═O)R₂₀₄,

—COOR₂₀₅,

a halogen atom, a cyano group, a nitro group,
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted heterocyclic group including 5 to 50 ring atoms;
R₂₀₁to R₂₀₅are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group including 5 to 50 ring atoms;
when two or more of each of R₂₀₁to R₂₀₅are present, the two or more of each of R₂₀₁to R₂₀₅may be the same or different;
L₂₁to L₂₄are independently a single bond, a substituted or unsubstituted alkylene group including 1 to 50 carbon atoms, a substituted or unsubstituted arylene group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group including 5 to 50 ring atoms;
Ar₂₁and Ar₂₂are independently a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group including 5 to 50 ring atoms.
In the compound (20), the positional relationship on benzene ring with which L₂₃and L₂₄are bonded may be ortho (o), meta (m) or para (p). The positional relationship is preferably ortho or meta, and particularly preferably meta.
Hereinafter, “one or more pairs of adjacent two or more among R₃₁to R₃₈may form a substituted or unsubstituted, saturated or unsaturated ring” in the compound represented by formula (20) will be described.
The “one or more pairs of adjacent two or more among R₃₁to R₃₈” is, for example, a pair of R₃₁and R₃₂, R₃₂and R₃₃, R₃₃and R₃₄, R₃₄and R₃₅, R₃₅and R₃₆, R₃₆and R₃₇, R₃₇and R₃₈, R₃₁, R₃₂and R₃₃, R₃₂, R₃₃and R₃₄, and the like.
The substituent in “substituted or unsubstituted” for the saturated or unsaturated ring is as described later for the formula (20).
The “saturated or unsaturated ring” means, for example, when the ring is formed of R₃₁and R₃₂, a ring formed by a carbon atom with which R₃₁is bonded, a carbon atom with which R₃₂is bonded, and one or more arbitrary elements. Specifically, when the ring is formed of R₃₁and R₃₂, and an unsaturated ring is formed of a carbon atom with which R₃₁is bonded, a carbon atom with which R₃₂is bonded, and four carbon atoms, the ring formed of R₃₁and R₃₂is a benzene ring.
The “arbitrary element” is preferably a C element, a N element, an O element, and a S element. In the arbitrary element (e.g., for element C or element N), chemical bonding sites which are not involved in the ring formation may be terminated by a hydrogen atom and the like.
The “one or more arbitrary element” is preferably two or more and 15 or less, more preferably 3 or more and 12 or less, and further preferably 3 or more and 5 or less arbitrary elements.
When a pair of R₃₂, R₃₃and R₃₄forms a ring, the compound represented by the formula (20) is, for example, a compound represented by the following formula (20-10). In the formula (20-10), for example, when R₆₁is a phenyl group, a pair of R₃₂, R₃₃and R₃₄forms a substituted ring.
In the formula (20-10), R₃₁, R₃₅to R₃₈, L₂₁to L₂₄, Ar₂₁and Ar₂₂are as defined in the formula (20), and R₆₁to R₆₆is the same as the substituent in the case of “substituted or unsubstituted” in the compound (20) described later (the arbitrary substituent in the compound (20)).
The “one or more pairs” means that, for example, R₃₁and R₃₂form a ring, and R₃₇and R₃₈may form a ring at the same time. In this case, the compound represented by the formula (20) is a compound represented by the following formula (20-11), for example. In the formula (20-11), for example, when R₇₁is a phenyl group, R₃₁and R₃₂form a substituted ring.
In the formula (20-11), R₃₃to R₃₆, L₂₁to L₂₄, Ar₂₁and Ar₂₂are as defined in the formula (20), and R₇₁to R₇₈is the same as the substituent in the case of “substituted or unsubstituted” in the compound (2) described later (the arbitrary substituent in the compound (2)).
In one embodiment, it is preferable that the compound (20) contain any one or both of a compound represented by the following formula (20a) and a compound represented by the following formula (20b) (hereinafter, referred to as a compound (20a) and a compound (20b)).
In the formulas (20a) and (20b), R₃₁to R₃₈, L₂₁to L₂₄, Ar₂₁and Ar₂₂are as defined in the formula (20).
In one embodiment, it is preferable that the compound (20) be a compound (20a), i.e., L₂₃and L₂₄are substituted with each other at the meta-position of a benzene ring.
In one embodiment, L₂₄in the compound (20) is preferably a single bond.
In one embodiment, L₂₃in the compound (20) is preferably a single bond.
In one embodiment, it is preferable that one of Ar₂₁and Ar₂₂in the compound (20) be a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, and the other be a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group including 5 to 50 ring atom.
In one embodiment, R₃₁to R₃₈in the compound (20) are preferably hydrogen atoms.
In one embodiment, the compound (20) is a compound represented by the following formula (20a-1) and/or a compound represented by the following formula (20b-1).
In the formulas (20a-1) and (20b-1), L₂₄is a single bond and R₃₁to R₃₈, L₂₁to L₂₃, Ar₂₁and Ar₂₂are as defined in the formula (20).
In one embodiment, the compound (20) is a compound represented by the following formula (20a-2) and/or a compound represented by the following formula (20b-2).
In the formulas (20a-2) and (20b-2), L₂₃is a single bond and R₃₁to R₃₈, L₂₁, L₂₂, L₂₄, Ar₂₁and Ar₂₂are as defined in the formula (20).
In one embodiment, the compound (20) is a compound represented by the following formula (20a-3) and/or a compound represented by the following formula (20b-3).
In the formulas (20a-3) and (20b-3), L₂₁to L₂₄, Ar₂₁and Ar₂₂are as defined in the formula (20).
In one embodiment, the compound (20) is a compound represented by the following formula (20a-4).
In the formula (20a-4), L₂₃is a single bond and L₂₁, L₂₂, L₂₄, Ar₂₁and Ar₂₂are as defined in the formula (20).
Examples of the substituent in the case of “substituted or unsubstituted” in the compounds (20), (20a), (20b), (20a-1), (20b-1), (20a-2), (20b-2), (20a-3), (20b-3), and (20a-4) (hereinafter, also referred to as the arbitrary substituent of the compound (20)) include an alkyl group including 1 to 50 carbon atoms, an alkenyl group including 2 to 50 carbon atoms, an alkynyl group including 2 to 50 carbon atoms, a cycloalkyl group including 3 to 50 ring carbon atoms, an alkoxy group including 1 to 50 carbon atoms, an alkylthio group including 1 to 50 carbon atoms, an aryloxy group including 6 to 50 ring carbon atoms, an arylthio group including 6 to 50 ring carbon atoms, an aralkyl group including 7 to 50 carbon atoms, —Si(R₄₁)(R₄₂)(R₄₃), —C(═O)R₄₄, —COOR₄₅, —S(═O)₂R₄₆, —P(═O)(R₄₇)(R₄₅), —Ge(R₄₉)(R₅₀)(R₅₁), a hydroxyl group, a halogen atom, a cyano group, a nitro group, an aryl group including 6 to 50 ring carbon atoms, and a heterocyclic group including 5 to 50 ring atoms. R₄₁to R₅₁are independently a hydrogen atom, an alkyl group including 1 to 50 carbon atoms, an aryl group including 6 to 50 ring carbon atoms, or a heterocyclic group including 5 to 50 ring atoms. When two or more R₄₁to R₅₁are present, the two or more R₄₁to R₅₁may be the same or different. Among these, an alkyl group including 1 to 50 carbon atoms, an aryl group including 6 to 50 ring carbon atoms, or a heterocyclic group including 5 to 50 ring atoms is preferable, and an alkyl group including 1 to 18 carbon atoms, an aryl group including 6 to 18 ring carbon atoms, or a heterocyclic group including 5 to 18 ring atoms is more preferable.
Specific examples of each substituent, arbitrary substituent, and halogen atom in the compound (20) are as defined those described above, respectively, but each substituent and arbitrary substituent in the compound (20) do not contain a substituted or unsubstituted amino group. Thus, in the compound (20), there is only one amino group.
Specific examples of the compound (20) include, for example, the following compounds.
In addition to the above layers, an organic semiconductor layer, an adhesion-improving layer, an insulating layer, and the like may be provided between an emitting layer and an anode, or between an emitting layer and a cathode.
In one embodiment, it is preferable that the compound (10) be a host material of an emitting layer.
Further, the emitting layer containing the compound (10) may be a phosphorescent emitting layer or a fluorescent emitting layer, and may be a plurality of layers. The emitting layer containing the compound (10) is preferably a fluorescent emitting layer. When the plurality of emitting layers is present, a space layer may be provided between the respective emitting layers for the purpose of preventing excitons generated in the phosphorescent emitting layer from diffusing into the fluorescent emitting layer.
In one embodiment, the emitting layer further contains one or both of a fluorescent dopant and a phosphorescent dopant.
The emitting layer containing the compound (10) may further contain one or both of a fluorescent dopant and a phosphorescent dopant. The emitting layer containing the compound (10) preferably contains a fluorescent dopant.
Examples of the fluorescent dopant and the phosphorescent dopant include a fluorescence emitting material and a phosphorescence emitting material of a guest material of an emitting layer described later.
The organic EL device of the first embodiment includes, as described above, an anode, an emitting layer, a first electron-transporting layer, a second electron-transporting layer, and a cathode in this order, and the conventionally known materials and device structures can be applied as long as the effect of the present invention is not impaired except that the second electron-transporting layer contains the compound (1) and the emitting layer contains the compound (10).
Hereinafter, members and compounds constituting each layer which can be used in one embodiment of the organic EL device according to the first embodiment, other than the compound (1) and the compound (10) and the compounds (20) optionally used in the layer between the anode and the emitting layer will be described.

(Substrate)

A substrate is used as a support of an emitting device. As the substrate, glass, quartz, plastic, or the like can be used, for example. Further, a flexible substrate may be used. A term “flexible substrate” means a bendable (flexible) substrate, and specific examples thereof include a plastic substrate formed of polycarbonate or polyvinyl chloride.

(Anode)

For the anode formed on the substrate, metal, alloy, an electrically conductive compound, a mixture thereof or the like, each having a large work function (specifically 4.0 eV or more), is preferably used. Specific examples thereof include indium oxide-tin oxide (ITO: Indium Tin Oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide and indium oxide containing zinc oxide, graphene, and the like. In addition thereto, specific examples thereof include gold (Au), platinum (Pt), or a nitride of a metallic material (for example, titanium nitride) and the like.

(Hole-Injecting Layer)

The hole-injecting layer is a layer containing a material having high hole-injecting properties. As the material having high hole-injecting properties, such a material can be used as molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, an aromatic amine compound, or a polymer compound (oligomer, dendrimer, polymer, etc.).

(Hole-Transporting Layer)

The hole-transporting layer is a layer containing a material having high hole-transporting properties. For the hole-transporting layer, an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used. A polymer compound such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. However, a material other than the above-described materials may be used as long as the material has higher transporting properties of holes in comparison with electrons. It should be noted that the layer containing the material having high hole-transporting properties may be formed into not only a monolayer, but also a layer in which two or more layers formed of the above-described materials are stacked.

(Guest Material of an Emitting Layer)

An emitting layer is a layer containing a material having high emitting property, and various material can be used. For example, as a material having high emitting property, a fluorescent compound which emits fluorescence or a phosphorescent compound which emits phosphorescence can be used. A fluorescent compound is a compound which can emit from a singlet excited state, and a phosphorescent compound is a compound which can emit from a triplet excited state.
As the blue fluorescent emitting material which can be used for an emitting layer, a pyrene derivative, a styrylamine derivative, a chrysene derivative, a fluoranthene derivative, a fluorene derivative, a diamine derivative, a triarylamine derivative, and the like can be used. As a green fluorescent emitting material which can be used for an emitting layer, an aromatic amine derivative, and the like can be used. As a red fluorescent emitting material which can be used for an emitting layer, a tetracene derivative, a diamine derivative, and the like can be used.
As a blue phosphorescent emitting material which can be used for an emitting layer, a metal complex such as an iridium complex, an osmium complex, a platinum complex, and the like is used. As a green phosphorescent emitting material which can be used for an emitting layer, an iridium complex, and the like is used. As a red phosphorescent emitting material which can be used for an emitting layer, a metal complex such as an iridium complex, a platinum complex, a terbium complex, a europium complex, and the like can be used.

(Host Material of an Emitting Layer)

As an emitting layer, a configuration may be employed in which the above-described material having high emitting property (guest material) is dispersed in another material (host material). As a material for dispersing a material having a high emitting property, various materials can be used, and it is preferable to use a material having a higher lowest unoccupied orbital level (LUMO level) and a lower highest occupied orbital level (HOMO level) than a material having a high emitting property.
As a material for dispersing a material having high emitting property (host material), 1) metal complex such as an aluminum complex, a beryllium derivative, and a zinc complex, 2) heterocyclic compound such as an oxadiazole derivative, a benzimidazole derivative, a phenanthroline derivative and the like, 3) fused aromatic compound such as a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, a chrysene derivative and the like, and 3) aromatic amine compound such as an triarylamine derivative, a fused polycyclic aromatic amine derivative and the like can be used.

(Electron-Transporting Layer)

An electron-transporting layer is a layer that comprises a substance having high electron-transporting property. As an electron-transporting layer, 1) metal complex such as an aluminum complex, a beryllium complex, and a zinc complex, 2) heteroaromatic compound such as an imidazole derivative a benzimidazole derivative, an azine derivative, a carbazole derivative, a phenanthroline derivative and the like, and 3) polymer can be used.

(Electron-Injecting Layer)

An electron-injecting layer is a layer containing a material high electron-injecting property. As an electron-injecting layer, a metal complex compound such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF₂), 8-hydroxyquinolinolato-lithium (Liq), and an alkali metal such as lithium oxide (LiO_x), an alkaline earth metal, or a compound thereof.

(Cathode)

For the cathode, a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like, having a small work function (specifically, 3.8 eV or less) is preferably used. Specific examples of such a cathode material include elements belonging to Group 1 or Group 2 of the Periodic Table of the Elements, i.e., an alkali metal such as lithium (Li) and cesium (Cs), an alkaline earth metal such as magnesium (Mg), calcium (Ca) and strontium (Sr), and alloys containing these metals (e.g., MgAg and AlLi); a rare earth metal such as europium (Eu) and ytterbium (Yb), and alloys containing these metals.
In the organic EL device of the first aspect, a method for forming each layer is not limited. A conventionally-known method for forming each layer according to a vacuum deposition process, a spin coating process or the like can be used. Each layer such as the emitting layer can be formed by a known method such as a vacuum deposition process, a molecular beam deposition process (MBE process), or an application process such as a dipping process, a spin coating process, a casting process, a bar coating process and a roll coating process, using a solution prepared by dissolving the material in the solvent
In the organic EL device of the first aspect, a film thickness of each layer is not particularly limited, but is ordinarily preferably in the range of several nm to 1 μm generally in order to suppress a defect such as a pinhole, keep low applied voltage, or improve the luminous efficiency.
The electronic apparatus according to the second aspect of the present invention is characterized by containing the organic electroluminescence device according to the first aspect.
Specific examples of the electronic apparatus include a display component such as an organic EL panel module, a display device such as a television, a mobile telephone, or a personal computer, and an emitting device such as a light, a vehicular lamp, and the like.

EXAMPLES

Next, the invention will be explained in more detail in accordance with the following Examples and Comparative Examples, which should not be construed as limiting the scope of the invention.

Example 1

(Fabrication of Organic EL Device)

A25 mm×75 mm×1.1 mm-thick glass substrate with an ITO transparent electrode (anode) (manufactured by GEOMATEC Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, and then subjected to UV-ozone cleaning for 30 minutes. The thickness of ITO was adjusted to 130 nm.
The glass substrate after being cleaned was mounted onto a substrate holder in a vacuum vapor deposition apparatus. Compounds HT and HI were co-deposited on a surface on the side on which the transparent electrode was formed so as to cover the transparent electrode to be 3% in a proportion (mass ratio) of the Compound HI to form a Compound HI film having a thickness of 5 nm. This HI film functions as a hole-injecting layer.
Following the formation of the HI film, Compound HT was deposited to form an 90 nm-thickness HT film on the HI film. The HT film functions as a first hole-transporting layer.
After formation of the HT film, Compound EB was deposited to form an EB film having a thickness of 5 nm on the HT film. The EB film functions as a second hole-transporting layer.
BH-1 (host material) and Compound BD (dopant material) were co-deposited on the EB film to be 4% in a proportion (mass ratio) of the Compound BD to form a 20 nm-thickness BH-1:BD film. The BH-1:BD film functions as an emitting layer.
HB-1 was deposited on the emitting layer to form a 5 nm-thickness HB-1 film. The HB-1 film functions as a first electron-transporting layer. Following the formation of the HB-1 film, Compound E-1 and Liq were co-deposited to be 50% in a proportion (mass ratio) of the Compound Liq to form a 20 nm-thickness E-1:Liq film. The E-1:Liq film functions as a second electron-transporting layer. Liq was deposited on the E-1:Liq film to form a Liq film having a thickness of 1 nm. Metal Al was deposited on the Liq film to form a metal cathode having a thickness of 80 nm. As described above, an organic EL device was fabricated.

(Evaluation of Organic EL Device)

Voltage was applied to the organic EL device to be 10 mA/cm²in current density, thereby measuring an EL emission spectrum of the obtained organic EL device by using Spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). External quantum efficiency (EQE) (%) was calculated from the obtained spectral radiance spectrum. The results are shown in Table 1.
Further, a voltage was applied to the organic EL device so that the current density was 50 mA/cm², and the lifetime LT95 (hr) until the luminance was 95% of the initial luminance (LT95@50 mA/cm²) was measured. The results are shown in Table 1.

Examples 2 to 24 and Comparative Example 1 to 7

The organic EL devices were fabricated and evaluated in the same manner as in Example 1 except that the compounds shown in the following Tables 1 to 4 were used as host materials of emitting layers, electron-transporting layers and electron-injecting layer materials. The results are shown in Tables 1 to 4.
The compounds used in Examples and Comparative examples are shown below.

TABLE 1

	Hole-	1st hole-	2nd hole-		Emitting	1st electron-	2nd electron-
	injecting	transporting	transporting	Emitting layer	layer	transporting	transporting	EQE	LT95
No.	layer	layer	layer	Host	Dopant	layer	layer	(%)	(hr)

Example-1	HT:HI	HT	EB	Compound BH-1	BD	HB-1	Compound E-1:Liq	10.3	105
Example-2	HT:HI	HT	EB	Compound BH-1	BD	HB-1	Compound E-2:Liq	10.4	135
Example-3	HT:HI	HT	EB	Compound BH-1	BD	HB-1	Compound E-3:Liq	10.4	127
Comp. Ex-1	HT:HI	HT	EB	Compound BH-1	BD	HB-1	Comp. Compound	9.7	59
							EC-1:Liq
Comp. Ex-2	HT:HI	HT	EB	Compound BH-1	BD	HB-2	Comp. Compound	9.7	53
							EC-1:Liq

Comp. Ex-3	HT:HI	HT	EB	Compound BH-1	BD	Compound E-1	7.5	—
Comp. Ex-4	HT:HI	HT	EB	Compound BH-1	BD	Compound E-1:Liq	8.3	—

Comp. Ex-5	HT:HI	HT	EB	Compound BH-1	BD	Compound	HB-1:Liq	7.7	—
						E-1
Comp. Ex-6	HT:HI	HT	EB	Comp. Compound	BD	HB-1	Compound E-1:Liq	7.4	11
				BHC-1
Comp. Ex-7	HT:HI	HT	EB	Comp. Compound	BD	HB-1	Compound E-1:Liq	8.5	38
				BHC-2

From the results of Table 1, it can be seen that the devices of Examples 1 to 3 in which the compound represented by the formula (1) was used for the electron-injecting layer and the compound represented by the formula (10) was used as the host material of the emitting layer, have a high external quantum efficiency EQE and an improved device life.
In contrast, Comparative Examples 1 and 2 in which the compound represented by the formula (1) is not used in the electron-injecting layer have poor external quantum efficiency EQE and short device life.
In Comparative Examples 3 and 4 in which the organic layer between the cathode and the emitting layer is one layer, it can be seen that the external quantum efficiency EQE is inferior even if the compound represented by the formula (1) is used.
It can be seen that even if the organic layer between the cathode and the emitting layer is two layers, the external quantum efficiency EQE is inferior also in Comparative Example 5 in which the materials of the electron-transporting layer and the electron-injecting layer are exchanged.
It can be seen that in Comparative Examples 6 and 7 in which the compound represented by the formula (10) is not used as the host material of the emitting layer, the external quantum efficiency EQE and the device life are significantly inferior.

TABLE 2

	Hole-	1st hole-	2nd hole-		Emitting	1st electron-
	injecting	transporting	transporting	Emitting layer	layer	transporting	2nd electron-	EQE	LT95
No.	layer	layer	layer	Host	Dopant	layer	transporting layer	(%)	( hr)

Example-4	HT:HI	HT	EB	Compound BH-1	BD	HB-2	Compound E-1:Liq	10.4	101
Example-5	HT:HI	HT	EB	Compound BH-1	BD	HB-2	Compound E-2:Liq	10.6	121
Example-6	HT:HI	HT	EB	Compound BH-1	BD	HB-2	Compound E-3:Liq	10.5	118
Comp. Ex.-2	HT:HI	HT	EB	Compound BH-1	BD	HB-2	Comp. Compound	9.7	53
							EC-1:Liq

From the results of Table 2, it can be seen that in Examples 4 to 6, the external quantum efficiency EQE is high and the device life is improved even if the electron-transporting layer material is changed.
In contrast, in Comparative Example 2 in which only the material of the electron-injecting layer is changed to Compound EC-1 which is not the compound represented by the formula (1), it can be seen that the luminous efficiency is low and the device life is short.

TABLE 3

	Hole-	1st hole-	2nd hole-		Emitting	1st electron-
	injecting	transporting	transporting	Emitting layer	layer	transporting	2nd electron-	EQE	LT95
No.	layer	layer	layer	Host	Dopant	layer	transporting layer	(%)	(hr)

Example-7	HT:HI	HT	EB	Compound BH-2	BD	HB-1	Compound E-1:Liq	9.9	132
Example-8	HT:HI	HT	EB	Compound BH-2	BD	HB-1	Compound E-2:Liq	9.9	144
Example-9	HT:HI	HT	EB	Compound BH-2	BD	HB-1	Compound E-3:Liq	10.0	139
Example-10	HT:HI	HT	EB	Compound BH-3	BD	HB-1	Compound E-1:Liq	9.9	108
Example-11	HT:HI	HT	EB	Compound BH-3	BD	HB-1	Compound E-2:Liq	10.0	122
Example-12	HT:HI	HT	EB	Compound BH-3	BD	HB-1	Compound E-3:Liq	10.0	129
Example-13	HT:HI	HT	EB	Compound BH-4	BD	HB-1	Compound E-1:Liq	10.2	101
Example-14	HT:HI	HT	EB	Compound BH-4	BD	HB-1	Compound E-2:Liq	10.3	117
Example-15	HT:HI	HT	EB	Compound BH-4	BD	HB-1	Compound E-3:Liq	10.3	114
Comp. Ex.-1	HT:HI	HT	EB	Compound BH-1	BD	HB-1	Comp. Compound	9.7	59
							EC-1:Liq
Comp. Ex.-6	HT:HI	HT	EB	Comp. Compound	BD	HB-1	Compound E-1:Liq	7.4	11
				BHC-1
Comp. Ex.-7	HT:HI	HT	EB	Comp. Compound	BD	HB-1	Compound E-1:Liq	8.5	38
				BHC-2

From the results of Table 3, in Examples 7 to 15 in which the material of the electron-injecting layer is the compound represented by the formula (1) and the host material of the emitting layer is the compound represented by the formula (10), it can be seen that the efficiency EQE is high and the device life is improved.

TABLE 4

	Hole-	1st hole-	2nd hole-		Emitting	1st electron-
	injecting	transporting	transporting	Emitting layer	layer	transporting	2nd electron-	EQE	LT95
No.	layer	layer	layer	Host	Dopant	layer	transporting layer	(%)	(hr)

Example-16	HT:HI	HT	EB	Compound BH-1	BD	HB-3	Compound E-1:Liq	10.3	124
Example-17	HT:HI	HT	EB	Compound BH-1	BD	HB-3	Compound E-2:Liq	10.4	116
Example-18	HT:HI	HT	EB	Compound BH-1	BD	HB-3	Compound E-3:Liq	10.5	121
Example-19	HT:HI	HT	EB	Compound BH-1	BD	HB-4	Compound E-1:Liq	10.3	122
Example-20	HT:HI	HT	EB	Compound BH-1	BD	HB-4	Compound E-2:Liq	10.4	121
Example-21	HT:HI	HT	EB	Compound BH-1	BD	HB-4	Compound E-3:Liq	10.5	128
Example-22	HT:HI	HT	EB	Compound BH-1	BD	HB-5	Compound E-1:Liq	10.5	105
Example-23	HT:HI	HT	EB	Compound BH-1	BD	HB-5	Compound E-2:Liq	10.6	113
Example-24	HT:HI	HT	EB	Compound BH-1	BD	HB-5	Compound E-3:Liq	10.6	118

From the results of Table 4, in Examples 16 to 24 in which the material of the electron-injecting layer is the compound represented by the formula (1) and the host material of the emitting layer is the compound represented by the formula (10), it can be seen that the efficiency EQE is high and the device life is improved.
Although only some exemplary embodiments and/or examples of this invention have been described in detail above, those skilled in the art will readily appreciate that many modifications are possible in the exemplary embodiments and/or examples without materially departing from the novel teachings and advantages of this invention. Accordingly, all such modifications are intended to be included within the scope of this invention.
The documents described in the specification are incorporated herein by reference in its entirety.

Claims

1. An organic electroluminescence device, comprising:

an anode, an emitting layer, a first electron-transporting layer, a second electron-transporting layer and a cathode in this order, wherein

the second electron-transporting layer comprises a compound represented by the following formula (1), and

the emitting layer comprises a compound represented by the following formula (10):

wherein in the formula (1),

L₁is a single bond, or a group selected from the group consisting of

a substituted or unsubstituted phenylene group,

a substituted or unsubstituted biphenylene group,

a substituted or unsubstituted terphenylene group,

a substituted or unsubstituted quarterphenylene group,

a substituted or unsubstituted fused arylene group including 10 to 30 ring carbon atoms, and

a group in that 1 to 3 substituted or unsubstituted phenylene groups and 1 to 3 substituted or unsubstituted fused arylene groups including 10 to 30 ring carbon atoms are linked via a single bond;

Ar₁and Ar₂are independently a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 30 ring atoms and no nitrogen atom;

X₁to X₃are independently N or CR₁;

provided that two or more of X₁to X₃are N; R₁does not form a ring by bonding with adjacent L₁, Ar₁or Ar₂;

R₁'s are independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 20 carbon atoms, a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 30 ring atoms;

HA is a monovalent group represented by the following formula (HA):

wherein in the formula (HA),

Y₁to Y₈are independently N or CR₂; R₂'s are independently a hydrogen atom or a substituent;

when plural R₂'s are present, the plural R₂'s may be the same or different; plural R₂'s substituting on adjacent carbon atoms may form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other;

provided that one of Y₁to Y₈and atoms constituting the substituted or unsubstituted, saturated or unsaturated ring formed by bonding R₂'s with each other is a carbon atom bonded with L₁;

X₄is O or S;

wherein in the formula (10),

R₁₁to R₁₈are independently a hydrogen atom,

a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms,

a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms,

a substituted or unsubstituted alkylthio group including 1 to 50 carbon atoms,

a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms,

a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms,

a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms,

—Si(R₁₀₁)(R₁₀₂)(R₁₀₃),

—C(═O)R₁₀₄,

—COOR₁₀₅,

—N(R₁₀₆)(R₁₀₇),

a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;

R₁₀₁to R₁₀₇are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;

when two or more of each of R₁₀₁to R₁₀₇are present, the two or more of each of R₁₀₁to R₁₀₇may be the same or different;

provided that at least one of Ar₁₁and Ar₁₂is a monovalent group represented by the following formula (11);

wherein in the formula (11),

one of R₂₁to R₂₈is bonded with L₁₁or L₁₂;

R₂₁to R₂₈which are not bonded with L₁₁or L₁₂are independently a hydrogen atom,

a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms,

a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms,

a substituted or unsubstituted alkylthio group including 1 to 50 carbon atoms,

a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms,

—Si(R₁₀₁)(R₁₀₂)(R₁₀₃),

—C(═O)R₁₀₄,

—COOR₁₀₅,

—N(R₁₀₆)(R₁₀₇),

a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;

R₁₀₁to R₁₀₇are as defined above:

Ar₁₁or Ar₁₂, which is not the monovalent group represented by the formula (11), is an unsubstituted aryl group including 6 to 50 ring carbon atoms, an aryl group including 6 to 50 ring carbon atoms, which is substituted with an unsubstituted alkyl group including 1 to 50 carbon atoms, or an aryl group including 6 to 50 ring carbon atoms, which is substituted with an unsubstituted aryl group including 6 to 50 ring carbon atoms; and

L₁₁and L₁₂are independently a single bond, a substituted or unsubstituted alkylene group including 1 to 50 carbon atoms, a substituted or unsubstituted arylene group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group including 5 to 50 ring atoms.

2. The organic electroluminescence device according to claim 1, wherein the compound represented by the formula (1) is a compound represented by the following formula (2):

wherein in the formula (2), L₁, Ar₁, Ar₂and X₁to X₄are as defined in the formula (1);

one of Y_1ato Y_4ais a carbon atom bonded with L₁;

Y_5ato Y_8aand Y_1ato Y_4awhich is not the carbon atom bonded with L₁are independently N or CR₂; R₂'s are independently a hydrogen atom or a substituent; and

when plural R₂'s are present, the plural R₂'s may be the same or different; plural R₂'s substituting on adjacent carbon atoms may form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other.

3. The organic electroluminescence device according to claim 1, wherein the compound represented by the formula (1) is a compound represented by the following formula (2A):

wherein in the formula (2A), X₄, L₁, Ar₁, Ar₂and X₁to X₃are as defined in the formula (1);

one of Y_1bto Y_4bis a carbon atom bonded with L₁;

Y_5bto Y_8band Y_1bto Y_4bwhich is not the carbon atom bonded with L₁are independently N or CR₃; R₃'s are independently a hydrogen atom or a substituent; and

when plural R₃'s are present, the plural R₃'s may be the same or different; plural R₃'s substituting on adjacent carbon atoms do not form a ring.

4. The organic electroluminescence device according to claim 1, the compound represented by the formula (1) is selected from the group consisting of compounds represented by any of the following formulas (3-1) to (3-12):

wherein in the formulas (3-1) to (3-12), L₁, Ar₁, Ar₂, X₁to X₄and Y₁to Y₈are as defined in the formula (1);

R₄'s are independently a substituent;

n1's are an integer of 0 to 4, n2's are an integer of 0 to 3; when n1 and n2 are two or more, plural R₄'s may be the same or different; plural R₄'s substituting on adjacent carbon atoms may form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other.

5. The organic electroluminescence device according to claim 1, wherein L₁is a single bond, or a group selected from the group consisting of

a substituted or unsubstituted phenylene group,

a substituted or unsubstituted biphenylene group,

a substituted or unsubstituted terphenylene group,

a substituted or unsubstituted quarterphenylene group,

a group in that 1 to 3 substituted or unsubstituted phenylene groups and 1 to 3 substituted or unsubstituted fused arylene groups are linked via a single bond; and

in the case that L₁has a substituent, the substituent is a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 30 ring atoms, except for a carbazolyl group.

6. The organic electroluminescence device according to claim 1, wherein L₁is a single bond, or the unsubstituted arylene group including 6 to 30 ring carbon atoms.

7. The organic electroluminescence device according to claim 1, wherein L₁is a single bond, or the unsubstituted arylene group including 6 to 12 ring carbon atoms.

8. The organic electroluminescence device according to claim 1, wherein L₁is a single bond, or a group selected from the group consisting of divalent groups represented by any of the following formulas (a1) to (a3).

9. The organic electroluminescence device according to claim 1, wherein L₁is a single bond, or a group selected from the group consisting of divalent groups represented by any of the following formulas (a1-1) to (a1-3).

10. The organic electroluminescence device according to claim 1, wherein Ar₁and Ar₂are independently a substituted or unsubstituted aryl group including 6 to 12 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 12 ring atoms and no nitrogen atom.

11. The organic electroluminescence device according to claim 1, wherein Ar₁and Ar₂are independently a group selected from the group consisting of monovalent groups represented by any of the following formulas (b1) to (b3).

wherein in the formulas (b1) to (b3),

R₅'s are independently a substituent,

p's are an integer of 0 to 5,

q is an integer of 0 to 7,

m is an integer of 0 to 4;

when p, q or m is two or more, plural R₅'s may be the same or different, and

when p, q or m is two or more, plural R₅'s do not form a ring by bonding with each other.

12. The organic electroluminescence device according to claim 1, wherein Ar₁and Ar₂are independently a group selected from the group consisting of monovalent groups represented by any of the following formulas (b1-1) and (b3-1) to (b3-3):

wherein in the formulas (b1-1), and (b3-1) to (b3-3),

R₅'s are independently a substituent,

p's are an integer of 0 to 5,

m's are an integer of 0 to 4;

when p or m is two or more, plural R₅'s may be the same or different, and

when p or m is two or more, plural R₅'s do not form a ring by bonding with each other.

13. The organic electroluminescence device according to claim 1, wherein X₁to X₃are N.

14. The organic electroluminescence device according to claim 1, wherein the compound represented by the formula (1) is selected from the group consisting of compounds represented by any of the following formulas (2A-1) to (2A-4):

wherein in the formulas (2A-1) to (2A-4), L₁and X₁to X₄are as defined in the formula (1)

Y_1bto Y_8bare independently N or CR₃; R₃'s are independently a hydrogen atom or a substituent;

when plural R₃'s are present, the plural R₃'s may be the same or different; plural R₃'s substituting on adjacent carbon atoms do not form a ring by bonding with each other; and

Ar_1aand Ar_2aare independently a substituted or unsubstituted aryl group including 6 to 12 ring carbon atoms.

15. The organic electroluminescence device according to claim 1, wherein the compound represented by the formula (1) is selected from the group consisting of compounds represented by any of the following formulas (2A-1-1) to (2A-4-1):

wherein in the formulas (2A-1-1) to (2A-4-1), X₄is as defined in the formula (1);

when plural R₃'s are present, the plural R₃'s may be the same or different; plural R₃'s substituting on adjacent carbon atoms do not form a ring by bonding with each other;

L_1bis a single bond or a group selected from the group consisting of divalent groups represented by any of the following formulas (a1) to (a3):

Ar_1band Ar_2bare independently a group selected from the group consisting of monovalent groups represented by any of the following formulas (b1) to (b3):

wherein in the formulas (b1) to (b3),

R₅'s are independently a substituent,

p's are an integer of 0 to 5,

q is an integer of 0 to 7,

m is an integer of 0 to 4;

when p, q or m is two or more, plural R₅'s may be the same or different, and

16. The organic electroluminescence device according to claim 1, wherein the compound represented by the formula (1) is selected from the group consisting of compounds represented by any of the following formulas (2A-1-2) to (2A-4-2):

wherein in the formulas (2A-1-2) to (2A-4-2), X₄is as defined in the formula (1);

L_1cis a single bond or a group selected from the group consisting of divalent groups represented by any of the following formulas (a1-1) to (a1-3):

Ar_1cand Ar_2care independently a group selected from the group consisting of monovalent groups represented by any of the following formulas (b1-1), and (b3-1) to (b3-3):

wherein in the formulas (b1-1), and (b3-1) to (b3-3),

R₅'s are independently a substituent,

p's are an integer of 0 to 5,

m's are an integer of 0 to 4;

when p or m is two or more, plural R₅'s may be the same or different, and

17. The organic electroluminescence device according to claim 1, wherein the compound represented by the formula (1) is selected from the group consisting of compounds represented by any of the following formulas (3-1-1) to (3-6-1):

wherein in the formulas (3-1-1) to (3-6-1), X₁to X₄and Y₁to Y₈are as defined in the formula (1);

R₄'s are independently a substituent;

n1's are an integer of 0 to 4; when n1 is 2 to 4, plural R₄'s may be the same or different; plural R₄'s substituting on adjacent carbon atoms may form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other;

L_1ais a single bond or an unsubstituted arylene group including 6 to 12 ring carbon atoms; and

18. The organic electroluminescence device according to claim 1, wherein the compound represented by the formula (1) is selected from the group consisting of compounds represented by any of the following formulas (3-1-2) to (3-6-2):

wherein in the formulas (3-1-2) to (3-6-2), X₄and Y₁to Y₈are as defined in the formula (1);

R₄'s are independently a substituent;

wherein in the formulas (b1) to (b3),

R₅'s are independently a substituent,

p's are an integer of 0 to 5,

q is an integer of 0 to 7,

m is an integer of 0 to 4;

when p, q or m is two or more, plural R₅'s may be the same or different, and

19. The organic electroluminescence device according to claim 1, wherein the compound represented by the formula (1) is selected from the group consisting of compounds represented by any of the following formulas (3-1-3) to (3-6-3):

wherein in the formulas (3-1-3) to (3-6-3), X₄and Y₁to Y₈are as defined in the formula (1);

R₄'s are independently a substituent;

wherein in the formulas (b1-1), and (b3-1) to (b3-3),

R₅'s are independently a substituent,

p's are an integer of 0 to 5,

m's are an integer of 0 to 4;

when p or m is two or more, plural R₅'s may be the same or different, and

20. The organic electroluminescence device according to claim 1, wherein the compound represented by the formula (1) is a compound represented by the following formula (4):

wherein in the formula (4), X₁to X₄, Y₁to Y₈and L₁are as defined in the formula (1);

R₆'s are independently a halogen atom, a cyano group, a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 20 carbon atoms, a substituted or unsubstituted aryl group including 6 to 12 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 30 ring atoms;

provided that when R₆is the monovalent heterocyclic group, R₆is a monovalent heterocyclic group other than a substituted or unsubstituted carbazolyl group;

r is an integer of 0 to 5; when r is 2 to 5, plural R₆'s may be the same or different, and when plural R₆'s are present, plural R₆'s do not form a ring by bonding with each other.

21. The organic electroluminescence device according to claim 1, wherein the compound represented by the formula (1) is a compound represented by the following formula (5):

wherein in the formula (5), X₁to X₄are as defined in the formula (1);

Ar_1dand Ar_2dare independently a substituted or unsubstituted aryl group including 6 to 12 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group including 5 to 12 ring atoms;

one of Y_1dto Y_4dis a carbon atom bonded with L_1a;

Y_5dto Y_8d, and Y_1dto Y_4dwhich are not the carbon atom bonded with L_1dare independently N or CR_2a; R_2a's are independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 12 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 12 ring atoms;

when plural R_2a's are present, the plural R_2a's may be the same or different; plural R_2a's substituting on adjacent carbon atoms may form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other; and

L_1dis a single bond or an unsubstituted arylene group including 6 to 12 ring carbon atoms.

22. The organic electroluminescence device according to claim 1, wherein the monovalent group represented by the formula (HA) is a group selected from the group consisting of the following groups:

wherein in the formula, Y₁to Y₈and X₄are as defined in the formula (1);

wherein in the formulas, X₄and Y₄are as defined in the formula (1).

23. The organic electroluminescence device according to claim 1, wherein the substituent in the case of “substituted or unsubstituted” in the formula (1) is selected from the group consisting of an alkyl group including 1 to 50 carbon atoms, an alkenyl group including 2 to 50 carbon atoms, an alkynyl group including 2 to 50 carbon atoms, a cycloalkyl group including 3 to 50 carbon atoms, an alkoxy group including 1 to 50 carbon atoms, an alkylthio group including 1 to 50 carbon atoms, an aryloxy group including 6 to 50 ring carbon atoms, an arylthio group including 6 to 50 ring carbon atoms, an aralkyl group including 7 to 50 carbon atoms, —Si(R₄₁)(R₄₂)(R₄₃), —C(═O)R₄₄, —COOR₄₅, —S(═O)₂R₄₆, —P(═O)(R₄₇)(R₄₈), —Ge(R₄₉)(R₅₀)(R₅₁), —N(R₅₂)(R₅₃), a hydroxy group, a halogen atom, a cyano group, a nitro group, an aryl group including 6 to 50 ring carbon atoms, and a heterocyclic group including 5 to 50 ring atoms, except for a carbazolyl group;

R₄₁to R₅₃are independently a hydrogen atom, an alkyl group including 1 to 50 carbon atoms, an aryl group including 6 to 50 ring carbon atoms, or a heterocyclic group including 5 to 50 ring atoms except for a carbazolyl group, and when two or more of each of R₄₁to R₅₃are present, the two or more of each of R₄₁to R₅₃may be the same or different.

24. The organic electroluminescence device according to claim 23, wherein the substituent in the case of “substituted or unsubstituted” in the formula (1) is selected from the group consisting of an alkyl group including 1 to 50 carbon atoms, an aryl group including 6 to 12 ring carbon atoms, and a monovalent heterocyclic group including 5 to 12 ring atoms.

25. The organic electroluminescence device according to claim 1, wherein the compound represented by the formula (10) is a compound represented by the following formula (10-1):

wherein in the formula (10-1), R₁₁to R₁₈, Ar₁₁, L₁₁, L₁₂, R₂₁, and R₂₃to R₂₈are as defined in the formula (10).

26. The organic electroluminescence device according to claim 1, wherein the compound represented by the formula (10) is a compound represented by the following formula (10-2):

wherein in the formula (10-2), L₁₁is a single bond; R₁₁to R₁₈, Ar₁₁, L₁₂, and R₂₁to R₂₈are as defined in the formula (10).

27. The organic electroluminescence device according to claim 1, wherein the compound represented by the formula (10) is a compound represented by the following formula (10-3):

wherein in the formula (10-3), L₁₁is a single bond; R₁₁to R₁₈, Ar₁₁, L₁₂, R₂₁, and R₂₃to R₂₈are as defined in the formula (10).

28. The organic electroluminescence device according to claim 1, wherein R₂₁to R₂₈which are not bonded with L₁₁are a hydrogen atom.

29. The organic electroluminescence device according to claim 1, wherein R₁₁to R₁₈are a hydrogen atom.

30. The organic electroluminescence device according to claim 1, wherein the compound represented by the formula (10) is a compound represented by the following formula (10-4):

wherein in the formula (10-4), L₁₁is a single bond; Ar₁₁and L₁₂are as defined in the formula (10).

31. The organic electroluminescence device according to claim 1, wherein the substituent in the case of “substituted or unsubstituted” in the formula (10) is selected from the group consisting of an alkyl group including 1 to 50 carbon atoms, an alkenyl group including 2 to 50 carbon atoms, an alkynyl group including 2 to 50 carbon atoms, a cycloalkyl group including 3 to 50 carbon atoms, an alkoxy group including 1 to 50 carbon atoms, an alkylthio group including 1 to 50 carbon atoms, an aryloxy group including 6 to 50 ring carbon atoms, an arylthio group including 6 to 50 ring carbon atoms, an aralkyl group including 7 to 50 carbon atoms, —Si(R₄₁)(R₄₂)(R₄₃), —C(═O)R₄₄, —COOR₄₅, —S(═O)₂R₄₆, —P(═O)(R₄₇)(R₄₈), —Ge(R₄₉)(R₅₀)(R₅₁), —N(R₅₂)(R₅₃), a hydroxy group, a halogen atom, a cyano group, a nitro group, an aryl group including 6 to 50 ring carbon atoms, and a monovalent heterocyclic group including 5 to 50 ring atoms;

R₄₁to R₅₃are independently a hydrogen atom, an alkyl group including 1 to 50 carbon atoms, an aryl group including 6 to 50 ring carbon atoms, or a monovalent heterocyclic group including 5 to 50 ring atoms, and when two or more of each of R₄₁to R₅₃are present, the two or more of each of R₄₁to R₅₃may be the same or different.

32. The organic electroluminescence device according to claim 31, wherein the substituent in the case of “substituted or unsubstituted” in the formula (10) is selected from the group consisting of an alkyl group including 1 to 50 carbon atoms, an aryl group including 6 to 50 ring carbon atoms, and a monovalent heterocyclic group including 5 to 50 ring atoms.

33. The organic electroluminescence device according to claim 31, wherein the substituent in the case of “substituted or unsubstituted” in the formula (10) is selected from the group consisting of an alkyl group including 1 to 18 carbon atoms, an aryl group including 6 to 18 ring carbon atoms, and a monovalent heterocyclic group including 5 to 18 ring atoms.

34. The organic electroluminescence device according to claim 1, wherein the second electron-transporting layer further comprises one or two or more selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, an alkaline earth metal halide, a rare earth metal oxide, a rare earth metal halide, an alkali metal-containing organic complex, an alkaline earth metal-containing organic complex, and a rare earth metal-containing organic complex.

35. The organic electroluminescence device according to claim 1, wherein the first electron-transporting layer comprises a compound represented by the following formula (30):

wherein in the formula (30),

X₁₁is a nitrogen atom, CH or CR₈₃;

when X₁₁is CR₈₃, the adjacent two among R₈₂to R₈₄may be bonded to each other, to form together with the two ring carbon atoms to which they are bonded, a substituted or unsubstituted aromatic hydrocarbon ring including 10 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring including 5 to 32 ring atoms;

R₈₁, and R₈₂to R₈₄which do not form the ring are independently a group represented by any of the following formulas (31) to (34):

wherein in the formulas (31) to (34),

L₃₁, L₃₃, L₃₆, L₃₈and L₃₉are independently a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 32 ring atoms;

L₃₂, L₃₄and L₃₅are independently a substituted or unsubstituted arylene group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group including 5 to 32 ring atoms;

L₃₇is a substituted or unsubstituted trivalent aromatic hydrocarbon ring group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted trivalent heterocyclic group including 5 to 32 ring atoms.

36. The organic electroluminescence device according to claim 1, wherein the organic electroluminescence device comprising at least one organic layer between the anode and the emitting layer.

37. The organic electroluminescence device according to claim 1, wherein the emitting layer further comprises one or both of a fluorescent dopant and a phosphorescent dopant.

38. An electronic apparatus, comprising the organic electroluminescence device according to claim 1.