WO2020075757A1

WO2020075757A1 - Organic electroluminescence element and electronic device using same

Info

Publication number: WO2020075757A1
Application number: PCT/JP2019/039827
Authority: WO
Inventors: 裕基中野; 太郎八巻; 聡美田崎; 加藤　朋希
Original assignee: 出光興産株式会社
Priority date: 2018-10-09
Filing date: 2019-10-09
Publication date: 2020-04-16

Abstract

This organic electroluminescence element includes a negative electrode, a positive electrode, and a luminous layer disposed between the negative electrode and the positive electrode, wherein the luminous layer includes a compound represented by formula (1) (at least one of R₁-R₁₃ is -L-N(R₉₀₆)(R₉₀₇)) and a compound represented by formula (11).

Description

Organic electroluminescence element and electronic device using the same

<< The present invention relates to an organic electroluminescence element and an electronic device using the same.

When a voltage is applied to the organic electroluminescence element (hereinafter, also referred to as “organic EL element”), holes are injected from the anode and electrons are injected from the cathode into the light emitting layer. Then, in the light emitting layer, the injected holes and electrons are recombined to form excitons.

In Patent Document 1, a polycyclic aromatic compound in which a plurality of aromatic rings are connected by a boron atom and a nitrogen atom is used as a dopant material for a light emitting layer of an organic EL device, and a specific anthracene-based compound is used as a host material. It is disclosed.

International Publication No. 2017/188111

However, the organic EL element disclosed in Patent Document 1 cannot be said to have sufficiently high luminous efficiency, and there is room for improvement.
An object of the present invention is to provide an organic EL device having excellent luminous efficiency and an electronic device using the organic EL device.

As a result of intensive studies by the present inventors, the compound (dopant) represented by the formula (1) and the compound (host material) having a specific structure represented by the formula (11) are combined to form a light emitting layer. It was found that an organic EL device exhibiting a high luminous efficiency can be obtained by using it for the above-mentioned, and the present invention has been completed.

According to the present invention, the following organic EL device and electronic device are provided.
1. A cathode,
An anode,
A light-emitting layer disposed between the cathode and the anode,
Have
The light emitting layer is
A compound represented by the following formula (1):
A compound represented by the following formula (11):
The organic electroluminescent element containing.

(In formula (1),
Ar ₁ is bonded to either or both of R ₃ and R ₁₃ to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
Ar ₂ is bonded to either or both of R ₅ and R ₆ to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
Ar ₁ and Ar ₂ that do not form a substituted or unsubstituted heterocycle are each independently
It is an aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a heterocyclic group having 5 to 50 ring atoms.
One or more adjacent two or more sets of R ₁ to R ₁₃ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form a ring.
R ₁ to R _{13 which} are not involved in the formation of the substituted or unsubstituted heterocycle and the formation of the substituted or unsubstituted saturated or unsaturated ring are each independently,
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-LN (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
L is
It is a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
However, at least one of R ₁ to R ₁₃ does not form the above-mentioned substituted or unsubstituted heterocycle, does not form the above-mentioned substituted or unsubstituted saturated or unsaturated ring, and -L- N (R ₉₀₆ ) (R ₉₀₇ ).
R ₉₀₁ to R ₉₀₇ are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more R ₉₀₁ to R ₉₀₇ exist, each of the two or more R ₉₀₁ to R ₉₀₇ may be the same or different.
m and n are each independently R ₁ and R, which are Ar ₁ and Ar ₂ and which can be substituted with an aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a heterocyclic group having 5 to 50 ring atoms. It is a number of _two . When m is 2 or more, two or more R ₁ 's may be the same or different, and when n is 2 or more, two or more R ₂ 's may be the same. And may be different. )

(In formula (11),
Ar ₁₀₁ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
L ₁₀₁ and L ₁₀₂ are each independently
It is a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
Two or more adjacent _ones of R ₁₀₁ to R ₁₀₄ and two or more adjacent _ones of R ₁₀₅ to R ₁₀₈ do not bond with each other to form a ring.
Two or more adjacent R ₁₁₁ to R ₁₁₇ do not bond to each other to form a ring.
R ₁₀₁ to R ₁₀₈ and R ₁₁₁ to R ₁₁₇ are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1). )

2. An electronic device comprising the organic EL element according to the above 1.

According to the present invention, it is possible to provide an organic EL element having excellent luminous efficiency and an electronic device using the organic EL element.

1 is a diagram illustrating a schematic configuration of an organic EL element according to one embodiment of the present invention.

[Definition]
As used herein, the term “hydrogen atom” includes isotopes having different neutron numbers, that is, protium, deuterium, and tritium.

In the present specification, in the chemical structural formula, at a bondable position where a symbol such as “R” or “D” representing a deuterium atom is not specified, a hydrogen atom, that is, a light hydrogen atom, a deuterium atom, or It is assumed that a tritium atom is bonded.

In the present specification, the number of ring-forming carbon atoms refers to the ring itself of a compound having a structure in which atoms are cyclically bonded (for example, a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). Indicates the number of carbon atoms among the atoms. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the ring-forming carbon number. The "number of ring carbon atoms" described below is the same unless otherwise specified. For example, a benzene ring has 6 ring-forming carbons, a naphthalene ring has 10 ring-forming carbons, a pyridine ring has 5 ring-forming carbons, and a furan ring has 4 ring-forming carbons. Further, for example, the 9,9-diphenylfluorenyl group has 13 ring-forming carbon atoms, and the 9,9′-spirobifluorenyl group has 25 ring-forming carbon atoms.
When a benzene ring or a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring-forming carbon atoms.

In the present specification, the number of ring-forming atoms means a compound having a structure in which atoms are cyclically bonded (for example, a monocyclic compound, a condensed ring, a ring assembly) (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, Ring compound) represents the number of atoms constituting the ring itself. The atoms that do not form a ring (eg, hydrogen atoms that terminate the bonds of the atoms that make up the ring) and the atoms that are included in the substituent when the ring is substituted with a substituent are not included in the number of ring-forming atoms. The “number of ring-forming atoms” described below is the same unless otherwise specified. For example, the pyridine ring has 6 ring-forming atoms, the quinazoline ring has 10 ring-forming atoms, and the furan ring has 5 ring-forming atoms. A hydrogen atom bonded to a carbon atom of a pyridine ring or a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms.

In the present specification, the “carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having XX to YY carbon atoms” represents the number of carbon atoms when the ZZ group is unsubstituted. The carbon number of the substituent in the case where it is performed 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, “atom number XX to YY” in the expression “substituted or unsubstituted ZZ group having XX to YY atoms” means the number of atoms when the ZZ group is unsubstituted, The number of atoms of the substituent when it is included is not included. Here, “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.

<< "Unsubstituted" in the case of "substituted or unsubstituted ZZ group" means that the ZZ group is not substituted with a substituent and a hydrogen atom is bonded. Alternatively, “substituted” in the case of “substituted or unsubstituted ZZ group” means that one or more hydrogen atoms in the ZZ group have been replaced by a substituent. Similarly, “substitution” in the case of “BB group substituted with AA group” means that one or more hydrogen atoms in BB group are replaced with AA group.

Hereinafter, the substituents described in the present specification will be described.
The ring-forming carbon number of the “unsubstituted aryl group” described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification. .
The number of ring-forming atoms of the “unsubstituted heterocyclic group” described herein is from 5 to 50, preferably from 5 to 30, more preferably from 5 to 18, unless otherwise specified herein. is there.
The carbon number of the “unsubstituted alkyl group” described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in the present specification.
The carbon number of the “unsubstituted alkenyl group” described in the present specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified in the present specification.
The carbon number of the “unsubstituted alkynyl group” described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified in the present specification.
The number of ring-forming carbon atoms of the “unsubstituted cycloalkyl group” described herein is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified in this specification. is there.
The number of ring-forming carbon atoms of the “unsubstituted arylene group” described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification. .
The number of ring-forming atoms of the “unsubstituted divalent heterocyclic group” described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 unless otherwise specified in the present specification. ~ 18.
The carbon number of the “unsubstituted alkylene group” described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in the present specification.

Specific examples (specific example group G1) of the “substituted or unsubstituted aryl group” described in the present specification include the following unsubstituted aryl groups and substituted aryl groups. (Here, the unsubstituted aryl group refers to the case where the “substituted or unsubstituted aryl group” is the “unsubstituted aryl group”, and the substituted aryl group is the “substituted or unsubstituted aryl group”. The term "substituted aryl group" is used below.) Hereinafter, the term "aryl group" includes both "unsubstituted aryl group" and "substituted aryl group".
The “substituted aryl group” is a case where the “unsubstituted aryl group” has a substituent, and examples thereof include a group in which the following “unsubstituted aryl group” has a substituent and examples of a substituted aryl group. . Note that the examples of the “unsubstituted aryl group” and the examples of the “substituted aryl group” listed here are merely examples, and the “substituted aryl group” described in the present specification includes “unsubstituted aryl group”. The group in which the “group” has a substituent further has a substituent, and the “substituted aryl group” further has a substituent.

Unsubstituted aryl group:
Phenyl group,
p-biphenyl group,
m-biphenyl group,
o-biphenyl group,
p-terphenyl-4-yl group,
a p-terphenyl-3-yl group,
p-terphenyl-2-yl group,
m-terphenyl-4-yl group,
m-terphenyl-3-yl group,
m-terphenyl-2-yl group,
o-terphenyl-4-yl group,
o-terphenyl-3-yl group,
o-terphenyl-2-yl group,
1-naphthyl group,
2-naphthyl group,
Anthryl group,
Benzoanthryl group,
Phenanthryl group,
Benzophenanthryl group,
Phenalenyl group,
Pyrenyl group,
A chrysenyl group,
Benzochrysenyl group,
Triphenylenyl group,
Benzotriphenylenyl group,
Tetracenyl group,
Pentacenyl group,
Fluorenyl group,
9,9′-spirobifluorenyl group,
Benzofluorenyl group,
Dibenzofluorenyl group,
A fluoranthenyl group,
Benzofluoranthenyl group,
Perylenyl group

Substituted aryl group:
o-tolyl group,
m-tolyl group,
p-tolyl group,
Para-xylyl group,
Meta-xylyl group,
Ortho-xylyl group,
Para-isopropylphenyl group,
Meta-isopropylphenyl group,
Ortho-isopropylphenyl group,
Para-t-butylphenyl group,
Meta-t-butylphenyl group,
Ortho-t-butylphenyl group,
3,4,5-trimethylphenyl group,
9,9-dimethylfluorenyl group,
9,9-diphenylfluorenyl group,
9,9-di (4-methylphenyl) fluorenyl group,
9,9-di (4-isopropylphenyl) fluorenyl group,
9,9-di (4-tbutylphenyl) fluorenyl group,
A cyanophenyl group,
Triphenylsilylphenyl group,
Trimethylsilylphenyl group,
Phenylnaphthyl group,
Naphthylphenyl group

The "heterocyclic group" described in the present specification is a cyclic group containing at least one hetero atom as a ring forming 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 in the present specification may be a monocyclic group or a condensed ring group.
The “heterocyclic group” described in the present specification may be an aromatic heterocyclic group or an aliphatic heterocyclic group.
Specific examples of the "substituted or unsubstituted heterocyclic group" (specific example group G2) described in the present specification include the following unsubstituted heterocyclic groups and substituted heterocyclic groups. (Here, an unsubstituted heterocyclic group refers to a case where “substituted or unsubstituted heterocyclic group” is an “unsubstituted heterocyclic group”, and a substituted heterocyclic group refers to “substituted or unsubstituted heterocyclic group.” Hereinafter, the term “heterocyclic group” is a “substituted heterocyclic group”.) Hereinafter, when simply referred to as “heterocyclic group”, both “unsubstituted heterocyclic group” and “substituted heterocyclic group” are used. Including.
The “substituted heterocyclic group” is a case where the “unsubstituted heterocyclic group” has a substituent, and the following “unsubstituted heterocyclic group” has a substituent or an example of a substituted heterocyclic group. And the like. The examples of the “unsubstituted heterocyclic group” and the examples of the “substituted heterocyclic group” are merely examples, and the “substituted heterocyclic group” described in the present specification includes “unsubstituted heterocyclic group”. A group in which the “substituted heterocyclic group” has a substituent further has a substituent, and a group in which the “substituted heterocyclic group” further has a substituent is also included.

Unsubstituted heterocyclic group containing nitrogen atom:
A pyrrolyl group,
Imidazolyl group,
Pyrazolyl group,
Triazolyl group,
Tetrazolyl group,
An oxazolyl group,
Isoxazolyl group,
An oxadiazolyl group,
Thiazolyl group,
An isothiazolyl group,
Thiadiazolyl group,
Pyridyl group,
A pyridazinyl group,
Pyrimidinyl group,
Pyrazinyl group,
Triazinyl group,
Indolyl group,
Isoindolyl group,
An indolizinyl group,
Quinolizinyl group,
Quinolyl group,
An isoquinolyl group,
Cinnolyl group,
Phthalazinyl group,
Quinazolinyl group,
Quinoxalinyl group,
Benzimidazolyl group,
Indazolyl group,
A phenanthrolinyl group,
Phenanthridinyl group,
Acridinyl group,
Phenazinyl group,
Carbazolyl group,
Benzocarbazolyl group,
Morpholino group,
Phenoxazinyl group,
Phenothiazinyl group,
Azacarbazolyl group,
Diazacarbazolyl group

Unsubstituted heterocyclic group containing oxygen atom:
Frill group,
An oxazolyl group,
Isoxazolyl group,
An oxadiazolyl group,
Xanthenyl group,
Benzofuranyl group,
An isobenzofuranyl group,
Dibenzofuranyl group,
Naphthobenzofuranyl group,
Benzoxazolyl group,
Benzoisoxazolyl group,
Phenoxazinyl group,
Morpholino group,
Dinaphthofuranyl group,
Azadibenzofuranyl group,
Diazadibenzofuranyl group,
Azanaphthobenzofuranyl group,
Diazanaphthobenzofuranyl group

Unsubstituted heterocyclic group containing a sulfur atom:
Thienyl group,
Thiazolyl group,
An isothiazolyl group,
Thiadiazolyl group,
Benzothiophenyl group,
Isobenzothiophenyl group,
Dibenzothiophenyl group,
Naphthobenzothiophenyl group,
Benzothiazolyl group,
Benzoisothiazolyl group,
Phenothiazinyl group,
A dinaphthothiophenyl group,
Azadibenzothiophenyl group,
Diazadibenzothiophenyl group,
Azanaphthobenzothiophenyl group,
Diazanaphthobenzothiophenyl group

A substituted heterocyclic group containing a nitrogen atom:
(9-phenyl) carbazolyl group,
(9-biphenylyl) carbazolyl group,
(9-phenyl) phenylcarbazolyl group,
(9-naphthyl) carbazolyl group,
A diphenylcarbazol-9-yl group,
A phenylcarbazol-9-yl group,
A methylbenzimidazolyl group,
Ethyl benzimidazolyl group,
Phenyltriazinyl group,
Biphenylyltriazinyl group,
Diphenyltriazinyl group,
Phenylquinazolinyl group,
Biphenylylquinazolinyl group

A substituted heterocyclic group containing an oxygen atom:
Phenyldibenzofuranyl group,
Methyldibenzofuranyl group,
t-butyldibenzofuranyl group,
Monovalent residue of spiro [9H-xanthene-9,9 '-[9H] fluorene]

Substituted heterocyclic groups containing a sulfur atom:
Phenyldibenzothiophenyl group,
A methyldibenzothiophenyl group,
t-butyldibenzothiophenyl group,
Monovalent residue of spiro [9H-thioxanthene-9,9 '-[9H] fluorene]

A monovalent group derived by removing one hydrogen atom bonded to a ring-forming atom of the following unsubstituted heterocycle containing at least one of a nitrogen atom, an oxygen atom, and a sulfur atom, and the following unsubstituted A group in which a monovalent group derived by removing one hydrogen atom bonded to a ring-forming atom of a heterocycle has a substituent:

In the formulas (XY-1) to (XY-18), X _A and Y _A are each independently an oxygen atom, a sulfur atom, NH, or CH ₂ . However, at least one of X _A and Y _A is an oxygen atom, a sulfur atom, or NH.
The heterocyclic ring represented by the above formulas (XY-1) to (XY-18) has a bond at an arbitrary position to be a monovalent heterocyclic group.
The monovalent group derived from the unsubstituted heterocyclic ring represented by the above formulas (XY-1) to (XY-18) has a substituent when the carbon atom constituting the skeleton in these formulas is when bonded hydrogen atoms is replaced by a substituent, or, X _a and Y _a is NH or CH _2, hydrogen atoms in these NH or CH ₂ may refer to a state in which is replaced by a substituent.

Specific examples (specific example group G3) of the “substituted or unsubstituted alkyl group” described in the present specification include the following unsubstituted alkyl groups and substituted alkyl groups. (Here, the unsubstituted alkyl group refers to a case where the “substituted or unsubstituted alkyl group” is an “unsubstituted alkyl group”, and the substituted alkyl group refers to a “substituted or unsubstituted alkyl group” Hereinafter, the term “substituted alkyl group” is referred to.) Hereinafter, the term “alkyl group” includes both “unsubstituted alkyl group” and “substituted alkyl group”.
The “substituted alkyl group” is a case where the “unsubstituted alkyl group” has a substituent, and examples thereof include a group in which the following “unsubstituted alkyl group” has a substituent and examples of a substituted alkyl group. . The examples of the “unsubstituted alkyl group” and the examples of the “substituted alkyl group” listed here are merely examples, and the “substituted alkyl group” described in this specification includes “unsubstituted alkyl group”. The group in which the “group” has a substituent further has a substituent, and the “substituted alkyl group” further has a substituent.

Unsubstituted alkyl group:
Methyl group,
Ethyl group,
n-propyl group,
Isopropyl group,
n-butyl group,
Isobutyl group,
s-butyl group,
t-butyl group

Substituted alkyl group:
Heptafluoropropyl group (including isomers),
Pentafluoroethyl group,
2,2,2-trifluoroethyl group,
Trifluoromethyl group

Specific examples (specific example group G4) of the “substituted or unsubstituted alkenyl group” described in the present specification include the following unsubstituted alkenyl groups and substituted alkenyl groups. (Here, the unsubstituted alkenyl group refers to a case where the “substituted or unsubstituted alkenyl group” is an “unsubstituted alkenyl group”, and the “substituted alkenyl group” refers to a “substituted or unsubstituted alkenyl group.” Is a "substituted alkenyl group".) Hereinafter, the term "alkenyl group" includes both "unsubstituted alkenyl group" and "substituted alkenyl group".
The `` substituted alkenyl group '' is a case where the `` unsubstituted alkenyl group '' has a substituent, and examples of the following `` unsubstituted alkenyl group '' include a group having a substituent and a substituted alkenyl group. . Note that the examples of the “unsubstituted alkenyl group” and the examples of the “substituted alkenyl group” are merely examples, and the “substituted alkenyl group” described in the present specification includes “unsubstituted alkenyl group”. The group in which the “group” has a substituent further has a substituent, and the “substituted alkenyl group” further has a substituent.

Unsubstituted alkenyl group and substituted alkenyl group:
Vinyl group,
Allyl group,
1-butenyl group,
2-butenyl group,
A 3-butenyl group,
1,3-butanedienyl group,
1-methylvinyl group,
1-methylallyl group,
1,1-dimethylallyl group,
2-methylallyl group,
1,2-dimethylallyl group

Specific examples (specific example group G5) of the “substituted or unsubstituted alkynyl group” described in the present specification include the following unsubstituted alkynyl groups. (Here, the unsubstituted alkynyl group refers to a case where the “substituted or unsubstituted alkynyl group” is an “unsubstituted alkynyl group”.) Hereinafter, when simply referred to as “alkynyl group”, Alkynyl group "and" substituted alkynyl group ".
The “substituted alkynyl group” is a case where the “unsubstituted alkynyl group” has a substituent, and examples thereof include the following “unsubstituted alkynyl group” having a substituent.

Unsubstituted alkynyl group:
Ethynyl group

Specific examples (specific example group G6) of the “substituted or unsubstituted cycloalkyl group” described in the present specification include the following unsubstituted cycloalkyl groups and substituted cycloalkyl groups. (Here, the unsubstituted cycloalkyl group refers to the case where the “substituted or unsubstituted cycloalkyl group” is an “unsubstituted cycloalkyl group”, and the substituted cycloalkyl group is the “substituted or unsubstituted The term "cycloalkyl group" means a "substituted cycloalkyl group".) Hereinafter, when simply referring to "cycloalkyl group", both "unsubstituted cycloalkyl group" and "substituted cycloalkyl group" are referred to. Including.
"Substituted cycloalkyl group" is a case where "unsubstituted cycloalkyl group" has a substituent, and examples of the following "unsubstituted cycloalkyl group" have a substituent and substituted cycloalkyl groups. And the like. It should be noted that the examples of the “unsubstituted cycloalkyl group” and the examples of the “substituted cycloalkyl group” are merely examples, and the “substituted cycloalkyl group” described in this specification includes “unsubstituted cycloalkyl group”. A group in which the “substituted cycloalkyl group” further has a substituent, a group in which the “substituted cycloalkyl group” further has a substituent, and the like are also included.

Unsubstituted aliphatic ring group:
Cyclopropyl group,
Cyclobutyl group,
Cyclopentyl group,
Cyclohexyl group,
A 1-adamantyl group,
A 2-adamantyl group,
1-norbornyl group,
2-norbornyl group

Substituted cycloalkyl group:
4-methylcyclohexyl group

Specific examples of the group represented by —Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ) described in the present specification (specific example group G7) include:
-Si (G1) (G1) (G1),
-Si (G1) (G2) (G2),
-Si (G1) (G1) (G2),
-Si (G2) (G2) (G2),
-Si (G3) (G3) (G3),
-Si (G5) (G5) (G5),
-Si (G6) (G6) (G6)
Is mentioned.
here,
G1 is an "aryl group" described in Specific Example Group G1.
G2 is the “heterocyclic group” described in Specific Example Group G2.
G3 is the “alkyl group” described in Specific Example Group G3.
G5 is the “alkynyl group” described in Specific Example Group G5.
G6 is the “cycloalkyl group” described in Specific Example Group G6.

Specific examples of the group represented by —O— (R ₉₀₄ ) described in the present specification (specific example group G8) include
-O (G1),
-O (G2),
-O (G3),
-O (G6)
Is mentioned.
here,
G1 is an "aryl group" described in Specific Example Group G1.
G2 is the “heterocyclic group” described in Specific Example Group G2.
G3 is the “alkyl group” described in Specific Example Group G3.
G6 is the “cycloalkyl group” described in Specific Example Group G6.

Specific examples of the group represented by -S- (R ₉₀₅ ) described in the present specification (specific example group G9) include
-S (G1),
-S (G2),
-S (G3),
-S (G6)
Is mentioned.
here,
G1 is an "aryl group" described in Specific Example Group G1.
G2 is the “heterocyclic group” described in Specific Example Group G2.
G3 is the “alkyl group” described in Specific Example Group G3.
G6 is the “cycloalkyl group” described in Specific Example Group G6.

Specific examples of the group represented by -N (R ₉₀₆ ) (R ₉₀₇ ) (specific example group G10) described in the present specification include:
-N (G1) (G1),
-N (G2) (G2),
-N (G1) (G2),
-N (G3) (G3),
-N (G6) (G6)
Is mentioned.
here,
G1 is an "aryl group" described in Specific Example Group G1.
G2 is the “heterocyclic group” described in Specific Example Group G2.
G3 is the “alkyl group” described in Specific Example Group G3.
G6 is the “cycloalkyl group” described in Specific Example Group G6.

具体 Specific examples (specific example group G11) of the “halogen atom” described in this specification include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

A specific example of the “alkoxy group” described in the present specification is a group represented by —O (G3), where G3 is an “alkyl group” described in the specific example group G3. The carbon number of the “unsubstituted alkoxy group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
A specific example of the “alkylthio group” described in the present specification is a group represented by —S (G3), where G3 is the “alkyl group” described in the specific example group G3. The carbon number of the “unsubstituted alkylthio group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
A specific example of the “aryloxy group” described in the present specification is a group represented by —O (G1), where G1 is the “aryl group” described in the specific example group G1. The ring-forming carbon number of the “unsubstituted aryloxy group” is from 6 to 50, preferably from 6 to 30, and more preferably from 6 to 18, unless otherwise specified herein.
A specific example of the “arylthio group” described in the present specification is a group represented by —S (G1), where G1 is the “aryl group” described in the specific example group G1. The ring-forming carbon number of the “unsubstituted arylthio group” is from 6 to 50, preferably from 6 to 30, and more preferably from 6 to 18, unless otherwise specified herein.
A specific example of the “aralkyl group” described in the present specification is a group represented by — (G3) — (G1), wherein G3 is an “alkyl group” described in the specific example group G3. , G1 is the “aryl group” described in Specific Example Group G1. Thus, an “aralkyl group” is an embodiment of a “substituted alkyl group” substituted with an “aryl group”. The carbon number of the “unsubstituted aralkyl group” which is the “unsubstituted alkyl group” substituted by the “unsubstituted aryl group” is 7 to 50, preferably 7 unless otherwise specified in the present specification. -30, more preferably 7-18.
Specific examples of the “aralkyl group” include, for example, benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl Group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2- β-naphthylethyl group, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group and the like.

Unless otherwise specified, the substituted or unsubstituted aryl group described in the present specification is preferably a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a p-terphenyl- 4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl- 2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, phenanthryl group , A pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-diphenylfluorenyl group and the like.

The substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, unless otherwise specified in the present specification. Nanthrolinyl group, carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group, Dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, (9 -Phenyl) carbazolyl group ((9-phenyl) carbazolyl -1-yl group, (9-phenyl) carbazol-2-yl group, (9-phenyl) carbazol-3-yl group, or (9-phenyl) carbazol-4-yl group), (9-biphenylyl) carbazolyl Group, (9-phenyl) phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofura Nyl, phenyldibenzothiophenyl, indolocarbazolyl, pyrazinyl, pyridazinyl, quinazolinyl, cinnolinyl, phthalazinyl, quinoxalinyl, pyrrolyl, indolyl, pyrrolo [3,2,1-jk] Carbazolyl group, furanyl group, benzofuranyl group, thiophenyl group, Benzothiophenyl, pyrazolyl, imidazolyl, benzimidazolyl, triazolyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, isothiazolyl, benzisothiazolyl, thiadiazolyl, isoxazolyl, benzisoxazolyl And a pyridinyl group, a piperidinyl group, a piperazinyl group, an imidazolidinyl group, an indolo [3,2,1-jk] carbazolyl group, a dibenzothiophenyl group, and the like.

The above-mentioned dibenzofuranyl group and dibenzothiophenyl group are specifically any one of the following groups unless otherwise described in this specification.

In the formulas (XY-76) to (XY-79), X _B is an oxygen atom or a sulfur atom.

Unless otherwise specified, the substituted or unsubstituted alkyl group described in the present specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group. And the like.

Unless otherwise specified, the “substituted or unsubstituted arylene group” described in the present specification means a divalent group of the above “aryl group”. Specific examples of the “substituted or unsubstituted arylene group” (specific example group G12) include a divalent group of the “aryl group” described in specific example group G1. That is, as a specific example (specific group G12) of the "substituted or unsubstituted arylene group", a group excluding one hydrogen bonded to the ring-forming carbon of the "aryl group" described in the specific group G1. Is.

Specific examples (specific example group G13) of the “substituted or unsubstituted divalent heterocyclic group” described in the present specification include groups obtained by divalently converting the “heterocyclic group” described in the specific example group G2. Is mentioned. That is, specific examples (specific example group G13) of the “substituted or unsubstituted divalent heterocyclic group” include one of the “heterocyclic groups” bonded to the ring-forming atom of the “heterocyclic group” described in the specific example group G2. It is a group excluding hydrogen.

具体 As a specific example (specific example group G14) of the “substituted or unsubstituted alkylene group” described in the present specification, a group in which the “alkyl group” described in the specific example group G3 is divalent is exemplified. That is, as a specific example (specific example group G14) of the “substituted or unsubstituted alkylene group”, one hydrogen bonded to the carbon forming the alkane structure of the “alkyl group” described in the specific example group G3 Excluded groups.

置換 The substituted or unsubstituted arylene group described in the present specification is preferably any one of the following groups unless otherwise described in the present specification.

In the formulas (XY-20) to (XY-29), (XY-83) and (XY-84), R ₉₀₈ is a substituent.
m901 is 0 to a 4 integer, when m901 represents 2 or more, to _{R 908} of existing in plural numbers may be the same as each other or may be different.

In the formulas (XY-30) to (XY-40), R ₉₀₉ is each independently a hydrogen atom or a substituent. Two R ₉₀₉ may be bonded to each other via a single bond to form a ring.

In formulas (XY-41) to (XY-46), R ₉₁₀ is a substituent.
m902 is an integer of 0 to 6. When m902 is 2 or more, a plurality of R ₉₁₀ may be the same as or different from each other.

置換 The substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the following groups unless otherwise described in the present specification.

In the formulas (XY-50) to (XY-60), R ₉₁₁ is a hydrogen atom or a substituent.

In the formula (XY-65) ~ (XY -75), X B is an oxygen atom or a sulfur atom.

In the present specification, the following formula (where the parent skeleton is an anthracene ring) in the case where “one or more pairs of adjacent two or more bind to each other to form a substituted or unsubstituted saturated or unsaturated ring” XY-80) will be described as an example.

For example, among R ₉₂₁ to R ₉₃₀ , “adjacent two which form a ring when one or more adjacent two or more are bonded to each other to form a ring” includes R ₉₂₁ and R ₉₂₂ , R ₉₂₂ and _R _{923, R 923} and _R _{924, R 924} and _R _{930, R 930} and _R _{925, R 925} and _R _{926, R 926} and _R _{927, R 927} and _R _{928, R 928} and _{R 929,} and R ₉₂₉ and R ₉₂₁ .

The “one or more sets” means that two or more adjacent two sets may form a ring at the same time. For example, when R ₉₂₁ and R ₉₂₂ combine with each other to form ring A, and at the same time, R ₉₂₅ and R ₉₂₆ combine with each other to form ring B, the compound is represented by the following formula (XY-81) .

“When two or more adjacent groups form a ring”, for example, R ₉₂₁ and R ₉₂₂ combine with each other to form ring A, and R ₉₂₂ and R ₉₂₃ combine with each other to form ring C In the case where three adjacent R ₉₂₁ to R ₉₂₃ are fused to the anthracene mother skeleton to form a ring A and a ring C sharing R ₉₂₂ , they are represented by the following formula (XY-82).

The rings A to C formed in the above formulas (XY-81) and (XY-82) are saturated or unsaturated rings.
“Unsaturated ring” means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. “Saturated ring” means an aliphatic hydrocarbon ring or an aliphatic heterocyclic ring.
For example, in Formula (XY-81), a ring A formed by bonding R ₉₂₁ and R ₉₂₂ to each other has a carbon atom of an anthracene skeleton to which R ₉₂₁ is bonded and a carbon atom of an anthracene skeleton to which R ₉₂₂ is bonded. A ring formed by atoms and one or more optional elements is meant. As a specific example, when a ring A is formed by R ₉₂₁ and R ₉₂₂ , the carbon atom of the anthracene skeleton to which R ₉₂₁ is bonded, the carbon atom of the anthracene skeleton to which R ₉₂₂ is bonded, and four carbon atoms are different. When forming a saturated ring, the ring formed by R ₉₂₁ and R ₉₂₂ is a benzene ring. When a saturated ring is formed, the ring is a cyclohexane ring.

Here, the “arbitrary element” is preferably a C element, an N element, an O element, or an S element. In any element (for example, in the case of the C element or the N element), a bond that does not participate in ring formation may be terminated with a hydrogen atom or the like, or may be substituted with an arbitrary substituent. When any element other than the C element is included, the formed ring is a heterocyclic ring.
“One or more optional elements” constituting a saturated or unsaturated ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and still more preferably 3 or more and 5 or less. .

As a specific example of the aromatic hydrocarbon ring, a structure in which the aryl group mentioned as a specific example in the specific example group G1 is terminated with a hydrogen atom is given.
As a specific example of the aromatic heterocyclic ring, a structure in which the aromatic heterocyclic group described as a specific example in the specific example group G2 is terminated with a hydrogen atom is given.
Specific examples of the aliphatic hydrocarbon ring include a structure in which the cycloalkyl group mentioned as a specific example in Specific Example Group G6 is terminated with a hydrogen atom.
When the above “saturated or unsaturated ring” has a substituent, the substituent is, for example, an “optional substituent” described later. Specific examples of the substituent in the case where the above “saturated or unsaturated ring” has a substituent are the substituents described in the above section of “the substituent described in the present specification”.

In one embodiment of the present specification, the substituent in the case of “substituted or unsubstituted” (hereinafter, may be referred to as “optional substituent”) may be:
An unsubstituted alkyl group having 1 to 50 carbon atoms,
An unsubstituted alkenyl group having 2 to 50 carbon atoms,
An unsubstituted alkynyl group having 2 to 50 carbon atoms,
An unsubstituted cycloalkyl group having 3 to 50 carbon atoms for ring formation,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N ( _R906 ) ( _R907 )
(here,
R ₉₀₁ to R ₉₀₇ are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. When two or more R ₉₀₁ to R ₉₀₇ exist, each of the two or more R ₉₀₁ to R ₉₀₇ may be the same or different. ),
Halogen atom, cyano group, nitro group,
It is a group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and an unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.

In one embodiment, the substituents when referred to as "substituted or unsubstituted" are:
An alkyl group having 1 to 50 carbon atoms,
It is a group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a monovalent heterocyclic group having 5 to 50 ring atoms.

In one embodiment, the substituents when referred to as "substituted or unsubstituted" are:
An alkyl group having 1 to 18 carbon atoms,
It is a group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a monovalent heterocyclic group having 5 to 18 ring atoms.

具体 Specific examples of each of the optional substituents are as described above.

In the present specification, unless otherwise specified, adjacent substituents may be substituted with a saturated or unsaturated ring (preferably a substituted or unsubstituted saturated or unsaturated 5- or 6-membered ring, (Preferably, a benzene ring).
In the present specification, an optional substituent may further have a substituent unless otherwise specified. Examples of the substituent further included in the optional substituent include those similar to the optional substituent described above.

[Organic EL device]
An organic EL device according to one aspect of the present invention is
A cathode,
An anode,
A light-emitting layer disposed between the cathode and the anode,
Have
The light emitting layer is
A compound represented by the following formula (1):
A compound represented by the following formula (11):
It is characterized by containing.

Each group in the above formulas (1) and (11) will be described later.

(Compound represented by Formula (1))
The compound represented by Formula (1) will be described.

The compound represented by the formula (1) has at least one amino group —N (R ₉₀₆ ) (R ₉₀₇ ). That is, at least one of R ₁ to R ₁₃ does not form the above-mentioned substituted or unsubstituted heterocycle, does not form the above-mentioned substituted or unsubstituted saturated or unsaturated ring, and -L- N (R ₉₀₆ ) (R ₉₀₇ ). The compound represented by the formula (1) having an amino group has a high hole trapping property.

In the formula (1), “Ar ₁ is bonded to either or both of R ₃ and R ₁₃ to form a substituted or unsubstituted heterocycle”, and “Ar ₂ is R _{5 or} R ₆ to form a substituted or unsubstituted heterocycle by being bonded to one or both of ₆ to form a substituted or unsubstituted heterocycle. For example, the case where Ar ₁ is bonded to R ₃ to form a heterocycle Ha containing a nitrogen atom is shown by the following formula (1-1). Although not described in the following formula (1-1), ring Ha may have an arbitrary substituent. The optional substituents may be the R _1, it may be a substituent other than R _1.

(In the formula (1-1), Ar ₁ , Ar ₂ , R ₁ , R ₂ , R ₄ to R ₁₃ , m and n are as defined in the formula (1).
Ha is a ring containing a nitrogen atom as a ring-forming element. Ring Ha may have a substituent. )

The "adjacent two of of _R 1 _{~ R 13",} specifically, _{R 2} to each other when together _{R 1} _{when R 1} there are a plurality, _{R 2} there are a plurality, _{R 3} and R ₄ , R ₄ and R ₅ , R ₆ and R ₇ , R ₇ and R ₈ , R ₈ and R ₉ , R ₁₀ and R ₁₁ , R ₁₁ and R ₁₂ , and R ₁₂ and R ₁₃ respectively. .

“One or more adjacent two or more pairs of R ₃ to R ₁₃ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring” will be described with reference to specific examples. For example, the following formula (1-2) shows the case where one set of R ₇ and R ₈ forms an unsubstituted benzene ring. Formula (1-3) below shows the case where one set of R ₈ and R ₉ forms an unsubstituted benzene ring. Formula (1-4) below shows the case where two sets of R ₇ and R ₈ and R ₁₁ and R ₁₂ each form an unsubstituted benzene ring. The following formula (1-5) shows the case where two groups of R ₈ and R ₉ and R ₁₀ and R ₁₁ each form an unsubstituted benzene ring.

(In the formulas (1-2) to (1-5), Ar ₁ , Ar ₂ , R ₁ to R ₅ , R ₇ , R ₉ , R ₁₀ to R ₁₂ , m and n are the same as those in the formula (1). As defined.)

“Ar ₁ and Ar ₂ which do not form a substituted or unsubstituted heterocycle are each independently an aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a heterocyclic group having 5 to 50 ring atoms. , ”And“ m and n can be independently substituted with an aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a heterocyclic group having 5 to 50 ring atoms, which are Ar ₁ and Ar _2. The number of R ₁ and R ₂ ”.
If m and n are 0, namely, _{when R 1} and _{R 2} are not substituted with Ar ₁ and Ar _2, Ar ₁ and Ar ₂ are each a monovalent aromatic hydrocarbon bonded only N Is a group or a monovalent heterocyclic group, and when m and n are 1, Ar ₁ and Ar ₂ are respectively bonded to 1 R ₁ and N, and 1 R ₂ and N 2 It is a valence group. Further, for example, when m and n are 2 or more, Ar ₁ and Ar ₂ are respectively bonded to N and m R ₁ and N and n R ₂ respectively, and have (m + 1) valence and ( n + 1) valent group.

In one embodiment, R ₁ to R _{13 in} the above formula (1) that are not involved in the formation of the substituted or unsubstituted heterocycle and the formation of the substituted or unsubstituted saturated or unsaturated ring. Of these, 1 to 4 are —LN (R ₉₀₆ ) (R ₉₀₇ ), where L, R ₉₀₆ and R ₉₀₇ are as defined in the above formula (1). .

In one embodiment, L in the above formula (1) is a single bond or a substituted or unsubstituted phenylene group.
In one embodiment, L in the above formula (1) is a single bond or an unsubstituted phenylene group.

In one embodiment, both Ar ₁ and Ar ₂ in the above formula (1) do not form the above-mentioned substituted or unsubstituted heterocycle.

In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (2).

(In the formula (2), R ₁ to R ₁₃ are as defined in the formula (1).
m1 and n1 are each independently an integer of 0 to 5. When m1 and n1 are 2 or more, a plurality of R ₁ and R ₂ may be the same or different from each other. )

In one embodiment, the compound represented by the formula (2) is a compound represented by the following formula (2a).

(In the formula (2a), R ₁ to R ₃ , R ₅ to R ₁₃ , L, R ₉₀₆ and R ₉₀₇ are as defined in the formula (1).
m1 and n1 are each independently an integer of 0 to 5. When m1 and n1 are 2 or more, a plurality of R ₁ and R ₂ may be the same or different from each other. )

In one embodiment, the compound represented by the formula (2) is a compound represented by the following formula (2b).

(In the formula (2b), R ₁ to R ₃ , R ₅ to R ₁₃ , R ₉₀₆ and R ₉₀₇ are as defined in the formula (1).
m1 and n1 are each independently an integer of 0 to 5. When m1 and n1 are 2 or more, a plurality of R ₁ and R ₂ may be the same or different from each other.
—N (R ₉₀₆ ) (R ₉₀₇ ) is bonded to the carbon atom in the ortho position, the carbon atom in the meta position, or the carbon atom in the para position of the phenyl group. )

In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (3).

(In the formula (3), R ₄ , R ₇ , R ₈ , R ₁₁ and R ₁₂ are as defined in the formula (1).
R ₁₄ to R ₁₉ are the same as R ₁ and R ₂ in the formula (1), respectively. )

In one embodiment, R ₁ to R _{13 in} the above formula (1) that are not involved in the formation of the substituted or unsubstituted heterocycle and the formation of the substituted or unsubstituted saturated or unsaturated ring. But,
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or -N (R ₉₀₆ ) (R ₉₀₇ ), wherein R ₉₀₆ and R ₉₀₇ are as defined in the above formula (1). It is).

In one embodiment, R ₃ , R ₅ , R ₆ , R ₇ , R ₉ , R ₁₀ , R ₁₂ and R ₁₃ in the above formula (1) are hydrogen atoms.

In one embodiment, the compound represented by the above formula (1) is a compound represented by the following formula (4).

(In the formula (4), R ₄ , R ₈ and R ₁₁ are as defined in the formula (1).
R ₁₅ and R ₁₈ are the same as R ₁ and R ₂ in the formula (1), respectively. )

In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (5).

(In the formula (5), R ₈ and R ₁₁ are as defined in the formula (1).
L ₄ is the same as L in the above formula (1).
R ₁₅ and R ₁₈ are the same as R ₁ and R ₂ in the formula (1), respectively.
R ₉₀₆ and R ₉₀₇ are as defined in the above formula (1). ]

In one embodiment, R ₈ , R ₁₁ , R ₁₅ and R ₁₈ in the formula (5) are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or -N (R ₉₀₆ ) (R ₉₀₇ ), wherein R ₉₀₆ and R ₉₀₇ are as defined in the above formula (1). It is).

In one embodiment, R ₄ in the above formula (1) is a substituted or unsubstituted diphenylamino group.

In one embodiment, R ₄ in the above formula (1) is —LN (R ₉₀₆ ) (R ₉₀₇ ), and R ₈ , R ₁₁ , R ₁₅ and R ₁₈ are each independently,
Hydrogen atom,
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.

In one embodiment, R ₈ , R ₁₁ , R ₁₅ and R ₁₈ in formula (5) are each independently
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, and R ₉₀₆ and R ₉₀₇ are unsubstituted phenyl groups.

Details of each substituent in the above formulas (1) to (5) and the substituent in the case of “substituted or unsubstituted” are as described in the column of “Definition” in this specification.

Specific examples of the compound represented by the formula (1) will be described below, but these are merely examples, and the compound represented by the formula (1) is not limited to the following specific examples. In the following specific compound, "Me" represents a methyl group, and "tBu" represents a tert-butyl group.

The compound represented by the formula (1) includes, for example, a group containing three benzene rings and a group containing N-Ar _1- (R ₁ ) _m and a group containing N-Ar _2- (R ₂ ) _n. The intermediate product can be produced by binding with (1st reaction), and the final product can be produced by binding the three benzene rings with a linking group (group containing B) (2nd reaction). In the first reaction, an amination reaction such as a Bhabhurt-Hartwig reaction can be applied. In the second reaction, a tandem hetero Friedel-Crafts reaction or the like can be applied.

(Compound represented by Formula (11))
Next, the compound represented by formula (11) will be described.

In one embodiment, the compound represented by the formula (11) is a compound represented by the following formula (12).

(In the formula (12), Ar ₁₀₁ , L ₁₀₁ , R ₁₀₁ to R _108, and R ₁₁₁ to R ₁₁₇ are as defined in the formula (11).)

In one embodiment, R ₁₀₁ to R ₁₀₈ in the formula (11) are each an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted cycloalkyl group having 3 to 6 carbon atoms, an unsubstituted ring It is an aryl group having 6 to 18 carbon atoms or a hydrogen atom.
In one embodiment, R ₁₀₁ to R ₁₀₈ in the above formula (11) are an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, or a hydrogen atom. is there.
In one embodiment, R ₁₀₁ to R ₁₀₈ in the above formula (11) are an unsubstituted aryl group having 6 to 18 ring carbon atoms, or a hydrogen atom.
In one embodiment, R ₁₀₁ to R ₁₀₈ in the above formula (11) are hydrogen atoms.

In one embodiment, R ₁₁₁ to R ₁₁₇ in the above formula (11) are an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted aryl group having 6 to 18 ring carbon atoms, or a hydrogen atom. .
In one embodiment, R ₁₁₁ to R ₁₁₇ in the above formula (11) are an unsubstituted aryl group having 6 to 18 ring carbon atoms, or a hydrogen atom.
In one embodiment, R ₁₁₁ to R ₁₁₇ in the above formula (11) are an unsubstituted alkyl group having 1 to 6 carbon atoms, or a hydrogen atom.
In one embodiment, R ₁₁₁ to R ₁₁₇ in the above formula (11) are hydrogen atoms.

In one embodiment, the compound represented by the formula (11) is a compound represented by the following formula (13).

(In Formula (13), Ar ₁₀₁ , L _101, and L ₁₀₂ are as defined in Formula (11) above.)

In one embodiment, L ₁₀₁ in the above formula (11) is a single bond,
It is an unsubstituted o-phenylene group or an unsubstituted m-phenylene group.

In one embodiment, Ar ₁₀₁ in the above formula (11) is selected from groups represented by the following formulas (b1) to (b6).

(In formulas (b1) to (b6),
_Ra is
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1).
p is an integer of 0 to 5.
q is an integer of 0 to 4.
r is an integer of 0 to 3.
When R _a is 2 or more, the plurality of R _a may be the same as or different from each other. )

In one embodiment, the compound represented by the formula (11) is a compound represented by the following formula (14).

(In the formula (14), Ar ₁₀₁ and L ₁₀₂ are as defined in the formula (11).)

In one embodiment, when L ₁₀₁ and L ₁₀₂ in the formula (11) are substituted or unsubstituted arylene groups having 6 to 50 ring carbon atoms, the arylene groups are each independently the following formula (c1): ) To (c17).

(In the formulas (c1) to (c17), * represents a single bond bonded to Ar ₁₀₁ or the 2-position of the dibenzofuran ring.
** is a single bond bonded to the anthracene skeleton in the above formula (11).
R ₁₂₀ is
An alkyl group having 1 to 50 carbon atoms,
An alkenyl group having 2 to 50 carbon atoms,
An alkynyl group having 2 to 50 carbon atoms,
A cycloalkyl group having 3 to 50 ring carbon atoms,
An alkylsilyl group having 1 to 50 carbon atoms,
It is a halogen atom or a cyano group.
m4 is an integer of 0 to 4.
m5 is an integer of 0 to 6.
When m4 and m5 are each 2 or more, a plurality of R ₁₂₀ may be the same as or different from each other.
When m4 and m5 are each 2 or more, adjacent R _120's are bonded to each other to form a saturated or unsaturated ring, or do not form a saturated or unsaturated ring. )

In one embodiment, the compound represented by the formula (11) is a compound represented by the following formula (15).

(In the formula (15), Ar ₁₀₁ is as defined in the formula (11).)

Details of each substituent in the above formulas (11) to (15) and (b1) to (b6) and the substituent in the case of “substituted or unsubstituted” are described in the “Definition” column of the present specification. As described.

Specific examples of the compound represented by the formula (11) will be described below, but these are merely examples, and the compound represented by the formula (11) is not limited to the following specific examples.

As described above, the organic EL element according to one aspect of the present invention has a cathode, an anode, and a light emitting layer disposed between the cathode and the anode, and the light emitting layer has the above formula ( Other than containing the compound represented by 1) and the compound represented by the formula (11), conventionally known materials and device configurations can be applied as long as the effects of the present invention are not impaired.

The content of the compound represented by the formula (1) in the light emitting layer is preferably 1% by mass or more and 20% by mass or less with respect to the entire light emitting layer. Further, the content of the compound represented by the formula (11) in the light emitting layer is preferably 80% by mass or more and 99% by mass or less with respect to the entire light emitting layer.

One aspect of the organic EL device of the present invention preferably has a hole transport layer between the anode and the light emitting layer.

One aspect of the organic EL device of the present invention preferably has an electron transport layer between the cathode and the light emitting layer.

Hereinafter, the layer structure of the organic EL element according to one aspect of the present invention will be described.
An organic EL element according to one aspect of the present invention includes an organic layer between a pair of electrodes including a cathode and an anode. The organic layer includes at least one layer containing an organic compound. Alternatively, the organic layer is formed by stacking a plurality of layers containing an organic compound. The organic layer may have a layer composed of only one or a plurality of organic compounds. The organic layer may have a layer that simultaneously contains an organic compound and an inorganic compound. The organic layer may have a layer composed of only one or more inorganic compounds.
At least one of the layers included in the organic layer is a light emitting layer. The organic layer may be configured as, for example, one light emitting layer, or may include other layers that can be adopted in the layer configuration of the organic EL element. The layer that can be adopted in the layer structure of the organic EL element is not particularly limited, but for example, a hole transport zone (hole transport layer, hole injection layer, provided between the anode and the light emitting layer, Electron blocking layer, exciton blocking layer, etc.), light emitting layer, space layer, electron transporting zone (electron transporting layer, electron injecting layer, hole blocking layer, etc.) provided between the cathode and the light emitting layer.

The organic EL element according to one aspect of the present invention may be, for example, a fluorescent or phosphorescent light emitting type monochromatic light emitting element, or a fluorescent / phosphorescent hybrid type white light emitting element. Further, it may be a simple type having a single light emitting unit or a tandem type having a plurality of light emitting units.
The “light emitting unit” refers to a minimum unit including an organic layer, at least one of the organic layers being a light emitting layer, and emitting light by recombination of injected holes and electrons.
Further, the “light emitting layer” described in the present specification is an organic layer having a light emitting function. The light emitting layer is, for example, a phosphorescent light emitting layer, a fluorescent light emitting layer, or the like, and may be a single layer or a plurality of layers.
The light emitting unit may be a laminated type having a plurality of phosphorescent light emitting layers or fluorescent light emitting layers. In this case, for example, a space layer for preventing excitons generated in the phosphorescent light emitting layer from diffusing into the fluorescent light emitting layer. May be provided between each light emitting layer.

Examples of the simple organic EL element include element configurations such as an anode / a light emitting unit / a cathode.
A typical layer structure of the light emitting unit is shown below. Layers in parentheses are optional.
(A) (hole injection layer /) hole transport layer / fluorescent emission layer (/ electron transport layer / electron injection layer)
(B) (hole injection layer /) hole transport layer / phosphorescence emitting layer (/ electron transport layer / electron injection layer)
(C) (hole injection layer /) hole transport layer / first fluorescent light emitting layer / second fluorescent light emitting layer (/ electron transport layer / electron injection layer)
(D) (hole injection layer /) hole transport layer / first phosphorescent emitting layer / second phosphorescent emitting layer (/ electron transporting layer / electron injecting layer)
(E) (Hole injection layer /) Hole transport layer / Phosphorescence emission layer / Space layer / Fluorescence emission layer (/ Electron transport layer / Electron injection layer)
(F) (hole injection layer /) hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer / space layer / fluorescent light emitting layer (/ electron transport layer / electron injection layer)
(G) (hole injecting layer /) hole transporting layer / first phosphorescent emitting layer / space layer / second phosphorescent emitting layer / space layer / fluorescent emitting layer (/ electron transporting layer / electron injecting layer)
(H) (hole injecting layer /) hole transporting layer / phosphorescent emitting layer / space layer / first fluorescent emitting layer / second fluorescent emitting layer (/ electron transporting layer / electron injecting layer)
(I) (Hole injection layer /) Hole transport layer / Electron blocking layer / Fluorescent emission layer (/ Electron transport layer / Electron injection layer)
(J) (Hole injection layer /) Hole transport layer / Electron blocking layer / Phosphorescent layer (/ Electron transport layer / Electron injection layer)
(K) (hole injection layer /) hole transport layer / exciton block layer / fluorescent emission layer (/ electron transport layer / electron injection layer)
(L) (Hole injection layer /) Hole transport layer / Exciton blocking layer / Phosphorescent layer (/ Electron transport layer / Electron injection layer)
(M) (hole injection layer /) first hole transport layer / second hole transport layer / fluorescent light emitting layer (/ electron transport layer / electron injection layer)
(N) (hole injection layer /) first hole transport layer / second hole transport layer / fluorescent light emitting layer (/ first electron transport layer / second electron transport layer / electron injection layer)
(O) (hole injection layer /) first hole transport layer / second hole transport layer / phosphorescent emitting layer (/ electron transport layer / electron injection layer)
(P) (Hole injection layer /) First hole transport layer / Second hole transport layer / Phosphorescent layer (/ First electron transport layer / Second electron transport layer / Electron injection layer)
(Q) (hole injection layer /) hole transport layer / fluorescent emission layer / hole blocking layer (/ electron transport layer / electron injection layer)
(R) (hole injection layer /) hole transport layer / phosphorescence emitting layer / hole blocking layer (/ electron transport layer / electron injection layer)
(S) (hole injection layer /) hole transport layer / fluorescent emission layer / exciton blocking layer (/ electron transport layer / electron injection layer)
(T) (hole injection layer /) hole transport layer / phosphorescence emitting layer / exciton blocking layer (/ electron transport layer / electron injection layer)

However, the layer structure of the organic EL element according to one embodiment of the present invention is not limited to these. For example, when the organic EL element has a hole injection layer and a hole transport layer, the hole injection layer is preferably provided between the hole transport layer and the anode. Further, when the organic EL element has an electron injection layer and an electron transport layer, it is preferable that the electron injection layer is provided between the electron transport layer and the cathode. In addition, each of the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer may be composed of one layer or may be composed of a plurality of layers.

The plurality of phosphorescent light emitting layers, and the phosphorescent light emitting layer and the fluorescent light emitting layer may be light emitting layers of mutually different colors. For example, the light emitting unit (f) includes a hole transport layer / first phosphorescent light emitting layer (red light emission) / second phosphorescent light emitting layer (green light emission) / space layer / fluorescent light emitting layer (blue light emission) / electron transport layer. You can also do it.
An electron blocking layer may be provided between each light emitting layer and the hole transport layer or the space layer. Further, a hole blocking layer may be provided between each light emitting layer and the electron transport layer. By providing the electron blocking layer or the hole blocking layer, electrons or holes can be confined in the light emitting layer, the probability of recombination of charges in the light emitting layer can be increased, and the light emission efficiency can be improved.

As a typical element structure of the tandem type organic EL element, for example, an element structure such as anode / first light emitting unit / intermediate layer / second light emitting unit / cathode can be mentioned.
The first light emitting unit and the second light emitting unit can be independently selected from the above light emitting units, for example.
The intermediate layer is also generally called an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, a connector layer, or an intermediate insulation layer. The intermediate layer is a layer that supplies electrons to the first light emitting unit and holes to the second light emitting unit, and can be formed of a known material.
Only one of the first light emitting unit and the second light emitting unit may be the light emitting layer of one embodiment of the present invention, or both may be the light emitting layer of one embodiment of the present invention.

The functions and materials of each layer of the organic EL element described in this specification will be described below.

(substrate)
The substrate is used as a support for the organic EL device. The substrate preferably has a light transmittance of 50% or more in the visible light region having a wavelength of 400 to 700 nm, and is preferably a smooth substrate. Examples of the material of the substrate include soda lime glass, aluminosilicate glass, quartz glass, plastic and the like. A flexible substrate can be used as the substrate. The flexible substrate refers to a substrate that can be bent (flexible), and examples thereof include a plastic substrate. Specific examples of the material forming the plastic substrate include polycarbonate, polyarylate, polyether sulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, polyethylene naphthalate and the like. Also, an inorganic vapor deposition film can be used.

(anode)
As the anode, for example, a metal, an alloy, a conductive compound, a mixture thereof, or the like, which has a large work function (specifically, 4.0 eV or more) is preferably used. Specific examples of the material of the anode include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, and oxide containing zinc oxide. Examples include indium and graphene. Further, gold, silver, platinum, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, palladium, titanium, and nitrides of these metals (for example, titanium nitride) can be given.

The anode is usually formed by depositing these materials on a substrate by a sputtering method. For example, indium oxide-zinc oxide can be formed by a sputtering method using a target in which zinc oxide is added at 1 to 10 mass% with respect to indium oxide. For example, for indium oxide containing tungsten oxide or zinc oxide, a target in which 0.5 to 5 mass% of tungsten oxide or 0.1 to 1 mass% of zinc oxide is added to indium oxide is used. It can be formed by a sputtering method.
Other methods of forming the anode include, for example, a vacuum vapor deposition method, a coating method, an inkjet method, a spin coating method and the like. For example, when silver paste or the like is used, a coating method, an inkjet method, or the like can be used.

Note that the hole injection layer formed in contact with the anode is formed using a material that facilitates hole injection regardless of the work function of the anode. Therefore, a general electrode material such as a metal, an alloy, a conductive compound, or a mixture thereof can be used for the anode. Specifically, alkali metals such as lithium and cesium; magnesium; alkaline earth metals such as calcium and strontium; alloys containing these metals (eg magnesium-silver, aluminum-lithium); rare earth metals such as europium and ytterbium. A material having a small work function such as an alloy containing a rare earth metal may be used for the anode.

(Hole injection layer)
The hole-injection layer is a layer containing a substance having a high hole-injection property and has a function of injecting holes from the anode into the organic layer. Examples of the substance having a high hole injecting property include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, and silver oxide. Compounds, tungsten oxides, manganese oxides, aromatic amine compounds, electron-withdrawing (acceptor) compounds, polymer compounds (oligomers, dendrimers, polymers, etc.) and the like. Of these, aromatic amine compounds and acceptor compounds are preferable, and acceptor compounds are more preferable.

Specific examples of the aromatic amine compound include 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4,4 ′, 4 ″ -tris [N- (3 -Methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA), 4,4'-bis [N- (4-diphenylaminophenyl) -N-phenylamino] biphenyl (abbreviation: DPAB), 4, 4′-bis (N- {4- [N ′-(3-methylphenyl) -N′-phenylamino] phenyl} -N-phenylamino) biphenyl (abbreviation: DNTPD), 1,3,5-tris [ N- (4-diphenylaminophenyl) -N-phenylamino] benzene (abbreviation: DPA3B), 3- [N- (9-phenylcarbazol-3-yl) -N-phenylamino -9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA2), 3- [N Examples thereof include-(1-naphthyl) -N- (9-phenylcarbazol-3-yl) amino] -9-phenylcarbazole (abbreviation: PCzPCN1).

As the acceptor compound, for example, a heterocyclic derivative having an electron-withdrawing group, a quinone derivative having an electron-withdrawing group, an arylborane derivative, a heteroarylborane derivative and the like are preferable, and specific examples thereof include hexacyanohexaazatriphenylene, 2, 3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane (abbreviation: F4TCNQ), 1,2,3-tris [(cyano) (4-cyano-2,3,5,5) 6-tetrafluorophenyl) methylene] cyclopropane and the like.
When the compound having an acceptor property is used, the hole injection layer preferably further contains a matrix material. As the matrix material, a material known as a material for an organic EL device can be used, and for example, an electron donating (donor) compound is preferably used.

(Hole transport layer)
The hole-transporting layer is a layer containing a substance having a high hole-transporting property and has a function of transporting holes from the anode to the organic layer.

The substance having a high hole-transporting property is preferably a substance having a hole mobility of 10 ⁻⁶ cm ² / (V · s) or more, and examples thereof include aromatic amine compounds, carbazole derivatives, anthracene derivatives, and Examples thereof include molecular compounds.

Specific examples of the aromatic amine compound include 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB), N, N′-bis (3-methylphenyl)- N, N′-diphenyl- [1,1′-biphenyl] -4,4′-diamine (abbreviation: TPD), 4-phenyl-4 ′-(9-phenylfluoren-9-yl) triphenylamine (abbreviation) : BAFLP), 4,4′-bis [N- (9,9-dimethylfluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: DFLDPBi), 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4,4 ′, 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA), 4 4'-bis [N- (spiro-9,9'-bifluoren-2-yl) -N- phenylamino] biphenyl (abbreviation: BSPB), and the like.

Specific examples of the carbazole derivative include 4,4′-di (9-carbazolyl) biphenyl (abbreviation: CBP), 9- [4- (9-carbazolyl) phenyl] -10-phenylanthracene (abbreviation: CzPA), 9 -Phenyl-3- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation: PCzPA) and the like can be given.

Specific examples of the anthracene derivative include 2-t-butyl-9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA), 9,10-di (2-naphthyl) anthracene (abbreviation: DNA), Examples thereof include 9,10-diphenylanthracene (abbreviation: DPAnth).

Specific examples of the polymer compound include poly (N-vinylcarbazole) (abbreviation: PVK) and poly (4-vinyltriphenylamine) (abbreviation: PVTPA).

If the compound has a hole transporting property higher than an electron transporting property, a substance other than these may be used in the hole transporting layer.

The hole transport layer may be a single layer or a laminate of two or more layers. In this case, it is preferable to dispose a layer containing a substance having a large energy gap among substances having a high hole transporting property on the side closer to the light emitting layer.

(Light emitting layer)
The light emitting layer is a layer containing a substance having high light emitting property (dopant material). As the dopant material, various materials can be used, and for example, a fluorescent light emitting compound (fluorescent dopant), a phosphorescent light emitting compound (phosphorescent dopant), and the like can be used. The fluorescence emitting compound is a compound capable of emitting light from a singlet excited state, and a light emitting layer containing the compound is called a fluorescence emitting layer. The phosphorescent compound is a compound capable of emitting light from a triplet excited state, and a light emitting layer containing the compound is called a phosphorescent layer.

The light emitting layer usually contains a dopant material and a host material for making it emit light efficiently. Note that the dopant material may be referred to as a guest material, an emitter, or a light emitting material depending on the literature. The host material may also be referred to as a matrix material depending on the literature.
One light emitting layer may include a plurality of dopant materials and a plurality of host materials. Further, there may be a plurality of light emitting layers.

In this specification, a host material combined with a fluorescent dopant is referred to as a “fluorescent host”, and a host material combined with a phosphorescent dopant is referred to as a “phosphorescent host”. It should be noted that the fluorescent host and the phosphorescent host are not distinguished only by the molecular structure. The phosphorescent host is a material forming a phosphorescent emitting layer containing a phosphorescent dopant, but does not mean that it cannot be used as a material forming a fluorescent emitting layer. The same applies to the fluorescent host.

The content of the dopant material in the light emitting layer is not particularly limited, but from the viewpoint of sufficient light emission and concentration quenching, it is preferably 0.1 to 70% by mass, and more preferably 0.1% by mass. -30% by mass, more preferably 1-30% by mass, even more preferably 1-20% by mass, particularly preferably 1-10% by mass.

<Fluorescent dopant>
Examples of the fluorescent dopant that can be used with the fluorescent dopant used in one embodiment of the present invention include, for example, fused polycyclic aromatic derivatives, styrylamine derivatives, condensed ring amine derivatives, boron-containing compounds, pyrrole derivatives, indole derivatives, Examples thereof include carbazole derivatives. Of these, condensed ring amine derivatives, boron-containing compounds and carbazole derivatives are preferable.
Examples of the condensed ring amine derivative include a diaminopyrene derivative, a diaminochrysene derivative, a diaminoanthracene derivative, a diaminofluorene derivative, and a diaminofluorene derivative in which one or more benzofuro skeletons are condensed.
Examples of the boron-containing compound include a pyrromethene derivative and a triphenylborane derivative.

The blue fluorescent dopant that can be used with the fluorescent dopant used in one embodiment of the present invention includes, for example, a pyrene derivative, a styrylamine derivative, a chrysene derivative, a fluoranthene derivative, a fluorene derivative, a diamine derivative, and a triarylamine derivative. Etc. Specifically, N, N′-bis [4- (9H-carbazol-9-yl) phenyl] -N, N′-diphenylstilbene-4,4′-diamine (abbreviation: YGA2S), 4- (9H -Carbazol-9-yl) -4 '-(10-phenyl-9-anthryl) triphenylamine (abbreviation: YGAPA), 4- (10-phenyl-9-anthryl) -4'-(9-phenyl-9H -Carbazol-3-yl) triphenylamine (abbreviation: PCBAPA) and the like.

Examples of the green fluorescent dopant that can be used with the fluorescent dopant used in one embodiment of the present invention include aromatic amine derivatives. Specifically, N- (9,10-diphenyl-2-anthryl) -N, 9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N- [9,10-bis (1,1 '-Biphenyl-2-yl) -2-anthryl] -N, 9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N- (9,10-diphenyl-2-anthryl) -N, N ', N'-Triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N- [9,10-bis (1,1'-biphenyl-2-yl) -2-anthryl] -N, N' , N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N- [9,10-bis (1,1'-biphenyl-2-yl)]-N- [4- (9H-carbazole -9-yl Phenyl] -N- phenyl-anthracene-2-amine (abbreviation: 2YGABPhA), N, N, 9- triphenylamine anthracene-9-amine (abbreviation: DPhAPhA), and the like.

As the red fluorescent dopant, a tetracene derivative, a diamine derivative, or the like can be used together with the fluorescent dopant used in one embodiment of the present invention. Specifically, N, N, N ′, N′-tetrakis (4-methylphenyl) tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N, N, N ′, N′-tetrakis (4-methylphenyl) acenaphtho [1,2-a] fluoranthene-3,10-diamine (abbreviation: p-mPhAFD) and the like can be given.

<Phosphorescent dopant>
Examples of the phosphorescent dopant include a phosphorescent heavy metal complex and a phosphorescent rare earth metal complex.
Examples of the heavy metal complex include iridium complex, osmium complex, platinum complex and the like. The heavy metal complex is preferably an orthometallated complex of a metal selected from iridium, osmium, and platinum.
Examples of rare earth metal complexes include terbium complexes and europium complexes. Specifically, tris (acetylacetonato) (monophenanthroline) terbium (III) (abbreviation: Tb (acac) ₃ (Phen)), tris (1,3-diphenyl-1,3-propanedionate) (mono) Phenanthroline) europium (III) (abbreviation: Eu (DBM) ₃ (Phen)), tris [1- (2-thenoyl) -3,3,3-trifluoroacetonato] (monophenanthroline) europium (III) (abbreviation) : Eu (TTA) ₃ (Phen)) and the like. These rare earth metal complexes are preferable as phosphorescent dopants because rare earth metal ions emit light due to electronic transition between different multiplicities.

Examples of the blue phosphorescent dopant include iridium complex, osmium complex, and platinum complex. Specifically, bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C2 ′] iridium (III) tetrakis (1-pyrazolyl) borate (abbreviation: FIr6), bis [2- (4 ′ , 6′-Difluorophenyl) pyridinato-N, C2 ′] iridium (III) picolinate (abbreviation: FIrpic), bis [2- (3 ′, 5′-bistrifluoromethylphenyl) pyridinato-N, C2 ′] iridium ( III) picolinate (abbreviation: Ir (CF3ppy) ₂ (pic)), bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C2 ′] iridium (III) acetylacetonate (abbreviation: FIracac), etc. Is mentioned.

Examples of green phosphorescent dopants include iridium complexes. Specifically, tris (2-phenylpyridinato-N, C2 ′) iridium (III) (abbreviation: Ir (ppy) ₃ ), bis (2-phenylpyridinato-N, C2 ′) iridium (III ) Acetylacetonate (abbreviation: Ir (ppy) ₂ (acac)), bis (1,2-diphenyl-1H-benzimidazolato) iridium (III) acetylacetonate (abbreviation: Ir (pbi) ₂ (acac)) , Bis (benzo [h] quinolinato) iridium (III) acetylacetonate (abbreviation: Ir (bzq) ₂ (acac)), and the like.

Examples of red phosphorescent dopants include iridium complexes, platinum complexes, terbium complexes, europium complexes and the like. Specifically, bis [2- (2′-benzo [4,5-α] thienyl) pyridinato-N, C3 ′] iridium (III) acetylacetonate (abbreviation: Ir (btp) ₂ (acac)), Bis (1-phenylisoquinolinato-N, C2 ′) iridium (III) acetylacetonate (abbreviation: Ir (piq) ₂ (acac)), (acetylacetonato) bis [2,3-bis (4-fluoro) (Phenyl) quinoxalinato] iridium (III) (abbreviation: Ir (Fdpq) ₂ (acac)), 2,3,7,8,12,13,17,18-octaethyl-21H, 23H-porphyrin platinum (II) (abbreviation) : PtOEP) and the like.

<Host material>
As the host material, examples of materials that can be used with the host material used in one embodiment of the present invention include metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; indole derivatives, pyridine derivatives, pyrimidine derivatives, triazine derivatives, quinolines. Heterocyclic compounds such as derivatives, isoquinoline derivatives, quinazoline derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, oxadiazole derivatives, benzimidazole derivatives, phenanthroline derivatives; naphthalene derivatives, triphenylene derivatives, carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, Condensed aromatic compounds such as chrysene derivatives, naphthacene derivatives and fluoranthene derivatives; aromatic compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives Family amine compounds, and the like. A plurality of types of host materials may be used in combination.

Specific examples of the metal complex include tris (8-quinolinolato) aluminum (III) (abbreviation: Alq), tris (4-methyl-8-quinolinolato) aluminum (III) (abbreviation: Almq3), bis (10-hydroxybenzo). [H] Quinolinato) beryllium (II) (abbreviation: BeBq2), bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (III) (abbreviation: BAlq), bis (8-quinolinolato) zinc (b) II) (abbreviation: Znq), bis [2- (2-benzoxazolyl) phenolato] zinc (II) (abbreviation: ZnPBO), bis [2- (2-benzothiazolyl) phenolato] zinc (II) (abbreviation: ZnBTZ) and the like.

Specific examples of the heterocyclic compound include 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD) and 1,3-bis [5 -(P-tert-Butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 3- (4-biphenylyl) -4-phenyl-5- (4- tert-Butylphenyl) -1,2,4-triazole (abbreviation: TAZ), 2,2 ′, 2 ″-(1,3,5-benzenetriyl) tris (1-phenyl-1H-benzimidazole) (Abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and the like can be given.

Specific examples of the condensed aromatic compound include 9- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation: CzPA) and 3,6-diphenyl-9- [4- (10- Phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation: DPCzPA), 9,10-bis (3,5-diphenylphenyl) anthracene (abbreviation: DPPA), 9,10-di (2-naphthyl) anthracene ( Abbreviation: DNA), 2-tert-butyl-9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA), 9,9'-bianthryl (abbreviation: BANT), 9,9 '-(stilbene- 3,3′-diyl) diphenanthrene (abbreviation: DPNS), 9,9 ′-(stilbene-4,4′-diyl) diphenanthrene (abbreviation: DPNS2) , 3,3 ′, 3 ″-(benzene-1,3,5-triyl) tripylene (abbreviation: TPB3), 9,10-diphenylanthracene (abbreviation: DPAnth), 6,12-dimethoxy-5,11-diphenyl Examples include chrysene.

Specific examples of the aromatic amine compound include N, N-diphenyl-9- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazol-3-amine (abbreviation: CzA1PA), 4- (10 -Phenyl-9-anthryl) triphenylamine (abbreviation: DPhPA), N, 9-diphenyl-N- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazol-3-amine (abbreviation: PCAPA) ), N, 9-diphenyl-N- {4- [4- (10-phenyl-9-anthryl) phenyl] phenyl} -9H-carbazol-3-amine (abbreviation: PCAPBA), N- (9,10- Diphenyl-2-anthryl) -N, 9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), 4,4′-bis [N- (1- (Futyl) -N-phenylamino] biphenyl (abbreviation: NPB or α-NPD), N, N′-bis (3-methylphenyl) -N, N′-diphenyl- [1,1′-biphenyl] -4, 4′-diamine (abbreviation: TPD), 4,4′-bis [N- (9,9-dimethylfluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: DFLDPBi, 4,4′-bis [ Examples thereof include N- (spiro-9,9′-bifluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: BSPB).

The fluorescent host is preferably a compound having a singlet level higher than that of the fluorescent dopant, and examples thereof include a heterocyclic compound and a condensed aromatic compound. As the condensed aromatic compound, for example, anthracene derivative, pyrene derivative, chrysene derivative, naphthacene derivative and the like are preferable.

The phosphorescent host is preferably a compound having a triplet level higher than that of the phosphorescent dopant, and examples thereof include a metal complex, a heterocyclic compound, and a condensed aromatic compound. Among these, for example, indole derivatives, carbazole derivatives, pyridine derivatives, pyrimidine derivatives, triazine derivatives, quinoline derivatives, isoquinoline derivatives, quinazoline derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, naphthalene derivatives, triphenylene derivatives, phenanthrene derivatives, fluoranthene derivatives, etc. preferable.

(Electron transport layer)
The electron-transporting layer is a layer containing a substance having a high electron-transporting property. The substance having a high electron-transporting property is preferably a substance having an electron mobility of 10 ⁻⁶ cm ² / Vs or more, and examples thereof include metal complexes, aromatic heterocyclic compounds, aromatic hydrocarbon compounds, and polymer compounds. Etc.

Examples of the metal complex include aluminum complex, beryllium complex, zinc complex and the like. Specifically, tris (8-quinolinolato) aluminum (III) (abbreviation: Alq), tris (4-methyl-8-quinolinolato) aluminum (abbreviation: Almq3), bis (10-hydroxybenzo [h] quinolinato) beryllium (Abbreviation: BeBq2), bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (III) (abbreviation: BAlq), bis (8-quinolinolato) zinc (II) (abbreviation: Znq), bis [2- (2-benzoxazolyl) phenolato] zinc (II) (abbreviation: ZnPBO), bis [2- (2-benzothiazolyl) phenolato] zinc (II) (abbreviation: ZnBTZ), and the like can be given.

Examples of the aromatic heterocyclic compound include imidazole derivatives such as benzimidazole derivatives, imidazopyridine derivatives and benzimidazophenanthridine derivatives; azine derivatives such as pyrimidine derivatives and triazine derivatives; quinoline derivatives, isoquinoline derivatives, phenanthroline derivatives and the like. Examples thereof include compounds having a nitrogen six-membered ring structure (including those having a phosphine oxide-based substituent on the heterocycle). Specifically, 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis [5- (ptert- Butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 3- (4-tert-butylphenyl) -4-phenyl-5- (4-biphenylyl)- 1,2,4-triazole (abbreviation: TAZ), 3- (4-tert-butylphenyl) -4- (4-ethylphenyl) -5- (4-biphenylyl) -1,2,4-triazole (abbreviation) : P-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), 4,4′-bis (5-methylbenzoxazol-2-yl) stilbene (abbreviation: BzOs), etc. And the like.

Examples of aromatic hydrocarbon compounds include anthracene derivatives and fluoranthene derivatives.

Specific examples of the polymer compound include poly [(9,9-dihexylfluorene-2,7-diyl) -co- (pyridine-3,5-diyl)] (abbreviation: PF-Py), poly [(9 , 9-dioctylfluorene-2,7-diyl) -co- (2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy) and the like.

If the compound has a higher electron transporting property than the hole transporting property, a substance other than these may be used in the electron transporting layer.

The electron transport layer may be a single layer or a laminate of two or more layers. In this case, it is preferable to dispose a layer containing a substance having a large energy gap among substances having a high electron transporting property on the side closer to the light emitting layer.

In the electron transport layer, for example, a metal such as an alkali metal, magnesium, an alkaline earth metal, an alloy containing two or more of these metals; an alkali metal compound such as 8-quinolinolatolithium (abbreviation: Liq), A metal compound such as an alkaline earth metal compound may be contained. When a metal such as an alkali metal, magnesium, an alkaline earth metal, or an alloy containing two or more of these metals is contained in the electron transport layer, the content thereof is not particularly limited, but 0 The amount is preferably 1 to 50% by mass, more preferably 0.1 to 20% by mass, and further preferably 1 to 10% by mass.
When the electron transport layer contains a metal compound such as an alkali metal compound or a metal compound such as an alkaline earth metal compound, the content thereof is preferably 1 to 99% by mass, more preferably 10 to 90% by mass. Is. The layer on the side of the light emitting layer in the case where the electron transport layer has a plurality of layers may be formed of only these metal compounds.

(Electron injection layer)
The electron injection layer is a layer containing a substance having a high electron injection property, and has a function of efficiently injecting electrons from the cathode to the light emitting layer. Examples of the substance having a high electron injecting property include alkali metals, magnesium, alkaline earth metals, and compounds thereof. Specific examples include lithium, cesium, calcium, lithium fluoride, cesium fluoride, calcium fluoride, and lithium oxide. Alternatively, a substance having an electron-transporting property containing an alkali metal, magnesium, an alkaline earth metal, or a compound thereof, for example, a substance containing Alq containing magnesium can be used.

Alternatively, a composite material containing an organic compound and a donor compound can be used for the electron-injection layer. Since the organic compound receives an electron from the compound having a donor property, such a composite material has an excellent electron injecting property and an electron transporting property.
As the organic compound, a substance having an excellent electron-transporting property is preferable, and for example, the above-described substance having a high electron-transporting property such as a metal complex or an aromatic heterocyclic compound can be used.
The donor compound may be any substance that can donate an electron to an organic compound, and examples thereof include alkali metals, magnesium, alkaline earth metals, and rare earth metals. Specific examples include lithium, cesium, magnesium, calcium, erbium and ytterbium. Moreover, alkali metal oxides and alkaline earth metal oxides are preferable, and specific examples thereof include lithium oxide, calcium oxide, and barium oxide. It is also possible to use a Lewis base such as magnesium oxide. Alternatively, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.

(cathode)
The cathode is preferably a metal, an alloy, a conductive compound, or a mixture thereof, which has a low work function (specifically, 3.8 eV or less). Examples of materials for the cathode include alkali metals such as lithium and cesium; magnesium; alkaline earth metals such as calcium and strontium; alloys containing these metals (eg magnesium-silver, aluminum-lithium); europium, ytterbium, etc. Rare earth metals; alloys containing rare earth metals, and the like.
The cathode is usually formed by a vacuum vapor deposition method or a sputtering method. When silver paste or the like is used, a coating method, an inkjet method, or the like can be used.

Further, when the electron injection layer is provided, the cathode is formed by using various conductive materials such as aluminum, silver, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, regardless of the work function. Can be formed. These conductive materials can be formed by a sputtering method, an inkjet method, a spin coating method, or the like.

(Insulating layer)
Since an organic EL element applies an electric field to a thin film, a pixel defect due to a leak or a short circuit easily occurs. In order to prevent this, a thin film insulating layer may be inserted between the pair of electrodes.
Specific examples of the substance used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, and oxide. Examples thereof include silicon, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide and the like. A mixture of these materials can be used for the insulating layer, or a stack of a plurality of layers containing these substances can be used.

(Space layer)
The space layer is provided between the two layers in order to prevent diffusion of excitons generated in the phosphorescent emitting layer into the fluorescent emitting layer and to adjust carrier balance when the fluorescent emitting layer and the phosphorescent emitting layer are stacked, for example. It is provided. The space layer can also be provided between a plurality of phosphorescent emitting layers and the like.
Since the space layer is provided between the plurality of light emitting layers, it is preferably formed of a substance having both an electron transporting property and a hole transporting property. Further, the triplet energy is preferably 2.6 eV or more from the viewpoint of preventing diffusion of the triplet energy in the adjacent phosphorescent emitting layer.
Examples of the substance used for the space layer include the same substances as those used for the hole transport layer described above.

(Electron blocking layer, hole blocking layer, exciton blocking layer)
An electron blocking layer, a hole blocking layer, an exciton (triplet) blocking layer, etc. may be provided adjacent to the light emitting layer.
The electron blocking layer is a layer having a function of blocking leakage of electrons from the light emitting layer to the hole transport layer. The hole blocking layer is a layer having a function of blocking leakage of holes from the light emitting layer to the electron transport layer. The exciton blocking layer is a layer having a function of blocking excitons generated in the light emitting layer from diffusing into an adjacent layer and confining the excitons in the light emitting layer.

(Middle layer)
In the tandem type organic EL device, an intermediate layer is provided.

(Layer forming method)
The method for forming each layer of the organic EL element is not particularly limited, unless otherwise specified. As a forming method, a known method such as a dry film forming method or a wet film forming method can be used. Specific examples of the dry film forming method include a vacuum vapor deposition method, a sputtering method, a plasma method, an ion plating method and the like. Specific examples of the wet film forming method include various coating methods such as a spin coating method, a dipping method, a flow coating method, and an inkjet method.

(Film thickness)
The film thickness of each layer of the organic EL element is not particularly limited, unless otherwise specified. If the film thickness is too small, defects such as pinholes are likely to occur and sufficient emission brightness cannot be obtained. On the other hand, if the film thickness is too large, a high driving voltage is required and the efficiency decreases. From such a viewpoint, the film thickness is usually preferably 1 nm to 10 μm, more preferably 1 nm to 0.2 μm.

[Electronics]
An electronic device according to one aspect of the present invention includes the above-described organic EL element according to one aspect of the present invention. Specific examples of electronic devices include display components such as organic EL panel modules; display devices such as televisions, mobile phones, smartphones, and personal computers; lighting, and light-emitting devices for vehicle lamps.

Next, the present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited to the description of these Examples.

<Compound>
The compounds represented by the formula (1) used for producing the organic EL devices of Examples 1 to 8 are shown below.

The compounds represented by the formula (11) used for manufacturing the organic EL devices of Examples 1 to 8 are shown below.

The comparative compounds used for manufacturing the organic EL devices of Comparative Examples 1 to 12 are shown below.

Other compounds used for manufacturing the organic EL devices of Examples 1 to 8 and Comparative Examples 1 to 12 are shown below.

Example 1
(Production of organic EL element)
A 25 mm × 75 mm × 1.1 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, and then UV ozone cleaning for 30 minutes. The film thickness of ITO was 130 nm.
The cleaned glass substrate with a transparent electrode was mounted on a substrate holder of a vacuum vapor deposition apparatus, and the compound HA-1 was vapor-deposited so as to cover the transparent electrode on the surface on which the transparent electrode was formed, and the film thickness was 5 nm. HA-1 film was formed. This HA-1 film functions as a hole injection layer.

Following the formation of this HA-1 film, the compound HT-1 was vapor-deposited to form an HT-1 film having a film thickness of 80 nm on the HA-1 film. This HT-1 film functions as a hole transport layer (first hole transport layer).
After forming the HT-1 film, a compound HT-2 was deposited, and a 10 nm-thick HT-2 film was formed on the HT-1 film. This HT-2 film functions as an electron blocking layer (second hole transport layer).
A compound BH-1 (host material) and a compound BD-1 (dopant material) are co-deposited on the HT-2 film so that the ratio of the compound BD-1 is 2% by mass. A BD-1 film was formed. This BH-1: BD-1 film functions as a light emitting layer.

Compound ET-1 was deposited on this light emitting layer to form a 10 nm-thick ET-1 film. This ET-1 film functions as a hole barrier layer.
Compound ET-2 was deposited on the ET-1 film to form a 15 nm-thick ET-2 film. This ET-2 film functions as an electron transport layer. LiF was deposited on the ET-2 film to form a 1 nm-thick LiF film. Metal Al was vapor-deposited on this LiF film to form a metal cathode having a film thickness of 80 nm, and an organic EL device was produced.

The layer structure of the obtained organic EL device is as follows.
ITO (130) / HA-1 (5) / HT-1 (80) / HT-2 (10) / BH-1: BD-1 (25: 2% by mass) / ET-1 (10) / ET- 2 (15) / LiF (1) / Al (80)
The numbers in parentheses indicate the film thickness (unit: nm). Similarly, in parentheses, the number in percent indicates the proportion (mass%) of the dopant material in the light emitting layer.

(Evaluation of organic EL element)
The initial characteristics of the obtained organic EL device were measured at room temperature by driving with a DC (direct current) constant current of 10 mA / cm ² . Table 1 shows the measurement results of the driving voltage.
Further, a voltage was applied to the organic EL element so that the current density was 10 mA / cm ^2, and the EL emission spectrum was measured with a spectral radiance meter CS-1000 (manufactured by Konica Minolta Co., Ltd.). The external quantum efficiency EQE (%) was calculated from the obtained spectral radiance spectrum. The results are shown in Table 1.

Examples 2-8 and Comparative Examples 1-12
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in Table 1 were used as the host material and the dopant material. The results are shown in Tables 1-1 and 1-2.

From the results of Tables 1-1 and 1-2, the organic EL devices of Examples 1 to 8 in which the specific host material and the specific dopant material were combined were higher than the organic EL devices of Comparative Examples 1 to 12. It can be seen that it exhibits external quantum efficiency.

The host materials BH-1 to BH-4 used in the examples and having dibenzofuran in the side chain have a high hole injecting property and the recombination region tends to diffuse. On the other hand, the dopant material BD-C1 in which a plurality of aromatic rings are connected by a boron atom and a nitrogen atom tends to have a low hole trapping property. Therefore, it was found that the combination of the dopant material BD-C1 and the host materials BH-1 to BH-4 is easily affected by diffusion of the recombination region.

On the other hand, the dopant material BD-1, which has a plurality of aromatic rings connected by a boron atom and a nitrogen atom and has an amino group, has a higher hole trapping property than BD-C1 having no amino group. Therefore, it is considered that when the dopant material BD-1 and the host materials BH-1 to BH-4 are combined, the influence of diffusion of the recombination region is less likely to occur, and the external quantum efficiency is increased.

While certain embodiments and / or examples of the invention have been described in detail above, those skilled in the art will recognize those exemplary embodiments and / or examples without departing substantially from the novel teachings and advantages of the invention. It is easy to make many changes to the embodiments. Accordingly, many of these changes are within the scope of the invention.
The entire contents of the documents and the application based on the Paris Convention priority of the present application are incorporated herein by reference.

Claims

A cathode,
An anode,
A light-emitting layer disposed between the cathode and the anode,
Have
The light emitting layer is
A compound represented by the following formula (1):
A compound represented by the following formula (11):
The organic electroluminescent element containing.

(In formula (1),
Ar 1 is bonded to either or both of R 3 and R 13 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
Ar 2 is bonded to either or both of R 5 and R 6 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
Ar 1 and Ar 2 that do not form a substituted or unsubstituted heterocycle are each independently
It is an aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a heterocyclic group having 5 to 50 ring atoms.
One or more adjacent two or more sets of R 1 to R 13 are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form a ring.
R 1 to R 13 which are not involved in the formation of the substituted or unsubstituted heterocycle and the formation of the substituted or unsubstituted saturated or unsaturated ring are each independently,
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R 901 ) (R 902 ) (R 903 ),
—O— (R 904 ),
-S- (R 905 ),
-LN (R 906 ) (R 907 ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
L is
It is a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
However, at least one of R 1 to R 13 does not form the above-mentioned substituted or unsubstituted heterocycle, does not form the above-mentioned substituted or unsubstituted saturated or unsaturated ring, and -L- N (R 906 ) (R 907 ).
R 901 to R 907 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more R 901 to R 907 exist, each of the two or more R 901 to R 907 may be the same or different.
m and n are each independently R 1 and R, which are Ar 1 and Ar 2 and which can be substituted with an aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a heterocyclic group having 5 to 50 ring atoms. It is a number of two . When m is 2 or more, two or more R 1 's may be the same or different, and when n is 2 or more, two or more R 2 's may be the same. And may be different. )

(In formula (11),
Ar 101 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
L 101 and L 102 are each independently
It is a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
Two or more adjacent ones of R 101 to R 104 and two or more adjacent ones of R 105 to R 108 do not bond with each other to form a ring.
Two or more adjacent R 111 to R 117 do not bond to each other to form a ring.
R 101 to R 108 and R 111 to R 117 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R 901 ) (R 902 ) (R 903 ),
—O— (R 904 ),
-S- (R 905 ),
-N (R 906 ) (R 907 ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are as defined in the above formula (1). )
In the formula (1), 1 to R 1 among R 1 to R 13 that are not involved in the formation of the substituted or unsubstituted heterocycle and the formation of the substituted or unsubstituted saturated or unsaturated ring The four are —LN (R 906 ) (R 907 ), wherein L, R 906 and R 907 are as defined in formula (1) above. Organic electroluminescent device.
The organic electroluminescent device according to claim 1 or 2, wherein L in the formula (1) is a single bond or a substituted or unsubstituted phenylene group.
The organic electroluminescent device according to claim 1, wherein both Ar 1 and Ar 2 in the formula (1) do not form the substituted or unsubstituted heterocycle.
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).

(In the formula (2), R 1 to R 13 are as defined in the formula (1).
m1 and n1 are each independently an integer of 0 to 5. When m1 and n1 are 2 or more, a plurality of R 1 and R 2 may be the same or different from each other. )
The organic electroluminescent device according to any one of claims 1 to 5, wherein the compound represented by the formula (1) is a compound represented by the following formula (3).

(In the formula (3), R 4 , R 7 , R 8 , R 11 and R 12 are as defined in the formula (1).
R 14 to R 19 are the same as R 1 and R 2 in the formula (1), respectively. )
In the above formula (1), R 1 to R 13 that are not involved in the formation of the substituted or unsubstituted heterocycle and the formation of the substituted or unsubstituted saturated or unsaturated ring are
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or -N (R 906 ) (R 907 ), wherein R 906 and R 907 are as defined in the above formula (1). .) The organic electroluminescent device according to any one of claims 1 to 5.
The organic electroluminescence according to any one of claims 1 to 5, wherein R 3 , R 5 , R 6 , R 7 , R 9 , R 10 , R 12 and R 13 in the formula (1) are hydrogen atoms. element.
9. 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).

(In the formula (4), R 4 , R 8 and R 11 are as defined in the formula (1).
R 15 and R 18 are the same as R 1 and R 2 in the formula (1), respectively. )
10. The organic electroluminescent device according to claim 1, wherein the compound represented by the formula (1) is a compound represented by the following formula (5).

(In the formula (5), R 8 and R 11 are as defined in the formula (1).
L 4 is the same as L in the above formula (1).
R 15 and R 18 are the same as R 1 and R 2 in the formula (1), respectively.
R 906 and R 907 are as defined in the above formula (1). ]
R 8 , R 11 , R 15 and R 18 in the formula (5) are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or -N (R 906 ) (R 907 ), wherein R 906 and R 907 are as defined in the above formula (1). .) The organic electroluminescent device according to claim 10.
The organic electroluminescence device according to any one of claims 1 to 9 and 11, wherein R 4 in the formula (1) is a substituted or unsubstituted diphenylamino group.
13. The organic electroluminescence device according to claim 1, wherein the compound represented by the formula (11) is a compound represented by the following formula (12).

(In the formula (12), Ar 101 , L 101 , R 101 to R 108, and R 111 to R 117 are as defined in the formula (11).)
14. The organic electroluminescent device according to claim 1, wherein R 101 to R 108 in the formula (11) are hydrogen atoms.
15. The organic electroluminescent element according to claim 1, wherein R 111 to R 117 in the formula (11) are hydrogen atoms.
13. The organic electroluminescence device according to claim 1, wherein the compound represented by the formula (11) is a compound represented by the following formula (13).

(In Formula (13), Ar 101 , L 101, and L 102 are as defined in Formula (11) above.)
L 101 in the formula (11) is a single bond,
The organic electroluminescence device according to any one of claims 1 to 16, which is an unsubstituted o-phenylene group or an unsubstituted m-phenylene group.
The organic electroluminescent device according to claim 1, wherein Ar 101 in the formula (11) is selected from groups represented by the following formulas (b1) to (b6).

(In formulas (b1) to (b6),
Ra is
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R 901 ) (R 902 ) (R 903 ),
—O— (R 904 ),
-S- (R 905 ),
-N (R 906 ) (R 907 ),
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are as defined in the above formula (1).
p is an integer of 0 to 5.
q is an integer of 0 to 4.
r is an integer of 0 to 3.
When R a is 2 or more, the plurality of R a may be the same as or different from each other. )
The organic electroluminescence device according to any one of claims 1 to 12 and 16, wherein the compound represented by the formula (11) is a compound represented by the following formula (14).

(In the formula (14), Ar 101 and L 102 are as defined in the formula (11).)
20. The organic electroluminescence device according to claim 1, wherein the compound represented by the formula (11) is a compound represented by the following formula (15).

(In the formula (15), Ar 101 is as defined in the formula (11).)
21. The organic electroluminescent device according to claim 1, further comprising a hole transport layer between the anode and the light emitting layer.
22. The organic electroluminescent device according to claim 1, further comprising an electron transport layer between the cathode and the light emitting layer.
An electronic device comprising the organic electroluminescent element according to any one of claims 1 to 22.