KR20210075089A - Novel compounds, organic electroluminescent devices, electronic devices - Google Patents

Abstract

(식 (1)에 있어서, R₁∼R₈ 중 적어도 하나는 중수소 원자이다. Ar₂는 하기 식 (2), (3) 또는 (4)로 표시되는 1가의 기이다.)

The present invention relates to a compound represented by the following formula (1).

(In the formula (1), _{at least one of R 1} to _{R 8} is a deuterium atom. Ar ₂ is a monovalent group represented by the following formula (2), (3) or (4).)

Description

Novel compounds, organic electroluminescent devices, electronic devices

The present invention relates to novel compounds, organic electroluminescent devices and electronic devices.

When a voltage is applied to an organic electroluminescent element (hereinafter, sometimes referred to as "organic EL element"), holes from the anode and electrons from the cathode are injected into the light emitting layer, respectively. Then, in the light emitting layer, the injected holes and electrons recombine to form excitons.

In order to improve the element performance of an organic electroluminescent element, although improvement of the material used for an organic electroluminescent element is progressing gradually (for example, patent documents 1-7), further performance improvement is calculated|required. In particular, since improvement of the lifespan of an organic EL element is an important subject leading to the life of a commercialized product, the material which can implement|achieve a long-life organic EL element is calculated|required.

[Patent Document 1] Korean Patent Laid-Open No. 2016-0141361 [Patent Document 2] Specification of US Patent Application Publication No. 2017/200899 [Patent Document 3] Korean Patent Laid-Open No. 2017-055411 [Patent Document 4] International Publication No. 2010/099534 [Patent Document 5] International Publication No. 2010/135395 [Patent Document 6] International Publication No. 2010/071362 [Patent Document 7] International Publication No. 2010/066830

An object of the present invention is to provide a compound capable of producing a long-life organic EL device, a long-lived organic EL device, and an electronic device using the organic EL device.

MEANS TO SOLVE THE PROBLEM As a result of repeating earnest research in order to achieve the said objective, the present inventors discovered that organic electroluminescent element excellent in lifetime is obtained when the compound which has a specific structure represented by Formula (1) is used, and completed this invention did.

According to the present invention, the following compounds, organic EL devices and electronic devices are provided.

1. A compound represented by the following formula (1).

(in formula (1),

R ₁ to _{R 8} are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

R ₉₀₁ to _{R 907} are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms;

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

R ₉₀₁ ~R ₉₀₇ a, if present more than one, each of the two or more R ₉₀₁ ~R ₉₀₇ may be subjected to may be the same different.

At least one of R ₁ to _{R 8} is a deuterium atom.

Adjacent two or more of R ₁ to _{R 4} and adjacent two or more of R ₅ to _{R 8} are not bonded to each other to form a ring.

L ₁ and L ₂ are each independently

single bond,

A substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

It is a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

Ar ₁ is

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

Ar ₂ is a monovalent group represented by the following formula (2), (3) or (4).

In formulas (2) to (4),

One or more pairs of adjacent two of R ₁₅ to _{R 20} combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

When _{one or more pairs of adjacent two of R 15} to _{R 20} combine with each other to not form a substituted or unsubstituted saturated or unsaturated ring, one of _{R 13} to _{R 20} is a single bond bonded to _{L 2 .}

When _{one or more pairs of adjacent R 15} to _{R 20} combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, R ₁₅ to R which does not form the substituted or unsubstituted saturated or unsaturated ring ₂₀ , and one of R ₁₃ and R ₁₄ is a single bond bonded to _{L 2 .}

_{R 13} to _{R 20} , and R ₁₁ and R ₁₂ which do not form the substituted or unsubstituted saturated or unsaturated ring and are not a single bond bonded to _{L 2} are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

R ₉₀₁ to _{R 907} are as defined in Formula (1) above.)

2. An organic electroluminescent device comprising a cathode, an anode, and one or two or more organic layers disposed between the cathode and the anode, wherein at least one of the organic layers contains the compound according to 1.

3. An electronic device provided with the organic electroluminescent element of 2.

ADVANTAGE OF THE INVENTION According to this invention, the compound which can manufacture long-life organic electroluminescent element, the long-life organic electroluminescent element, and the electronic device using the said organic electroluminescent element can be provided.

[Justice]

In the present specification, the hydrogen atom includes isotopes having different neutron numbers, that is, light hydrogen (protium), deuterium (deuterium), and tritium (tritium).

In the present specification, in the chemical structural formula, a hydrogen atom, that is, a light hydrogen atom, a deuterium atom or a tritium atom is bonded to a bondable position where a symbol such as "R" or "D" representing a deuterium atom is not specified. do.

In the present specification, the number of carbon atoms for forming a ring refers to the number of carbon atoms in the atoms constituting the ring itself of a compound (eg, monocyclic compound, condensed cyclic compound, crosslinked compound, carbocyclic compound, heterocyclic compound) having a structure in which atoms are bonded cyclically. represents the number. When the ring is substituted with a substituent, the carbon included in the substituent is not included in the number of ring carbon atoms. The "ring carbon number" described below is the same unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. Further, for example, the number of ring carbon atoms of the 9,9-diphenylfluorenyl group is 13, and the number of ring carbon atoms of the 9,9'-spirobifluorenyl group is 25.

In addition, when an alkyl group is substituted as a substituent on a benzene ring or a naphthalene ring, for example, carbon number of the alkyl group is not included in the number of ring carbon number.

In the present specification, the number of ring atoms refers to a compound (eg, monocyclic compound, condensed ring compound, crosslinked compound, carbocyclic compound, heterocyclic compound) of a structure (eg, monocyclic, condensed ring, ring set) in which atoms are cyclically bonded. represents the number of atoms that make up the ring itself. Atoms not constituting a ring (eg, a hydrogen atom terminating a bond of atoms constituting a ring) or atoms included in a substituent when the ring is substituted by a substituent are not included in the number of ring atoms. The "number of ring atoms" described below is the same unless otherwise specified. For example, the number of ring atoms of the pyridine ring is 6, the number of ring atoms of the quinazoline ring is 10, and the number of ring atoms of the furan ring is 5. Hydrogen atoms bonded to carbon atoms of the pyridine ring or quinazoline ring, or atoms constituting a substituent, respectively, are not included in the number of ring atoms.

In the present specification, the expression "a substituted or unsubstituted ZZ group having XX to YY carbon atoms" indicates that the "carbon number XX to YY" represents the number of carbon atoms when the ZZ group is unsubstituted, and the Carbon number is not included. Here, "YY" is greater than "XX", and "XX" and "YY" mean an integer of 1 or more, respectively.

In the present specification, "the number of atoms XX to YY" in the expression "a ZZ group having XX to YY substituted or unsubstituted atoms" indicates the number of atoms when the ZZ group is unsubstituted, and when substituted The number of atoms in the substituents is not included. Here, "YY" is greater than "XX", and "XX" and "YY" mean an integer of 1 or more, respectively.

"Unsubstituted" in the case of "a substituted or unsubstituted ZZ group" means that the ZZ group is not substituted with a substituent and a hydrogen atom is bonded. Alternatively, "substitution" in the case of "a substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are substituted with a substituent. "Substitution" in the case of "the BB group substituted with the AA group" means similarly that one or more hydrogen atoms in the BB group are substituted with the AA group.

Hereinafter, the substituents described in this specification are demonstrated.

The number of ring carbon atoms of the "unsubstituted aryl group" described in the present specification is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified in the present specification.

The number of ring atoms in the "unsubstituted heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified in the present specification.

The number of carbon atoms of the "unsubstituted alkyl group" described in the present specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified in the present specification.

The number of carbon atoms 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 number of carbon atoms of the "unsubstituted alkynyl 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 number of ring carbon atoms in the "unsubstituted cycloalkyl group" described in the present specification is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified in the present specification.

The number of ring carbon atoms of the "unsubstituted arylene group" described in the present specification is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified in the present specification.

The number of ring atoms of the "unsubstituted divalent heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified in the present specification.

The number of carbon atoms of the "unsubstituted alkylene group" described in the present specification is 1 to 50, preferably 1 to 20, 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 this specification include the following unsubstituted aryl groups and substituted aryl groups (herein, the unsubstituted aryl group means " A substituted or unsubstituted aryl group" refers to the case of an "unsubstituted aryl group", and a substituted aryl group refers to a case in which the "substituted or unsubstituted aryl group" is a "substituted aryl group"). Hereinafter, simply referred to as "aryl group" includes both "unsubstituted aryl group" and "substituted aryl group".

The "substituted aryl group" is a case in which the "unsubstituted aryl group" has a substituent, and examples of the group and the substituted aryl group in which the following "unsubstituted aryl group" has a substituent are exemplified. In addition, the examples of the "unsubstituted aryl group" and the examples of the "substituted aryl group" listed here are only examples, and in the "substituted aryl group" described in this specification, "unsubstituted aryl group" is a substituent Also included are groups in which the group having a group further has a substituent, and a group in which 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,

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,

benzoanthryl group,

phenanthryl group,

benzophenanthryl group,

phenalenyl group,

pyrenyl group,

chrysenyl group,

benzochrysenyl group,

triphenylenyl group,

benzotriphenylenyl group,

tetracenyl group,

pentacenyl group,

fluorenyl group,

9,9'-spirobifluorenyl group,

benzofluorenyl group,

dibenzofluorenyl group,

fluoranethenyl group,

benzofluorane ethenyl group,

Perylenyl group

A 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-dimethyl fluorenyl group,

9,9-diphenylfluorenyl group,

9,9-di (4-methylphenyl) fluorenyl group,

9,9-di (4-isopropylphenyl) fluorenyl group,

9,9-di (4-t-butylphenyl) fluorenyl group,

cyanophenyl group,

triphenylsilylphenyl group,

trimethylsilylphenyl group,

phenylnaphthyl group,

naphthylphenyl group

The "heterocyclic group" described in this 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 have either a monocyclic contribution or a condensed ring contribution.

An aromatic heterocyclic group may be sufficient as "heterocyclic group" described in this specification, and an aliphatic heterocyclic group may be sufficient as it.

Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic groups and substituted heterocyclic groups (herein, the term "unsubstituted heterocyclic group" means "A substituted or unsubstituted heterocyclic group" refers to the case of an "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to a case where "a substituted or unsubstituted heterocyclic group" is "a substituted heterocyclic group"). Hereinafter, simply referred to as "heterocyclic group" includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group".

The "substituted heterocyclic group" is a case where the "unsubstituted heterocyclic group" has a substituent, and examples of a group in which the following "unsubstituted heterocyclic group" has a substituent, a substituted heterocyclic group, etc. are mentioned. In addition, the examples of the "unsubstituted heterocyclic group" and the examples of the "substituted heterocyclic group" listed here are only examples, and in the "substituted heterocyclic group" described in this specification, "unsubstituted heterocyclic group" is a substituent Also included are groups in which the group having a group further has a substituent, a group in which the "substituted heterocyclic group" further has a substituent, and the like.

An unsubstituted heterocyclic group containing a nitrogen atom:

pyrrolyl group,

imidazolyl group,

pyrazolyl group,

triazolyl group,

tetrazolyl group,

oxazolyl group,

isoxazolyl group,

oxadiazolyl group,

thiazolyl group,

isothiazolyl group,

thiadiazolyl group,

pyridyl group,

pyridazinyl,

pyrimidinyl group,

pyrazinyl group,

triazinyl group,

indolyl group,

isoindolyl group,

indolizinyl group,

quinolizinyl group,

quinolyl group,

isoquinolyl group,

play fun,

phthalazinyl group,

quinazolinyl group,

quinoxalinyl group,

benzimidazolyl group,

indazolyl group,

phenanthrolinyl group,

phenanthridinyl group,

acridinyl group,

phenazinyl group,

carbazolyl group,

benzocarbazolyl group,

morpholino group,

phenoxadinyl group,

phenothiazinyl group,

azacarbazolyl group,

diazacarbazolyl group

An unsubstituted heterocyclic group containing an oxygen atom:

furyl,

oxazolyl group,

isoxazolyl group,

oxadiazolyl group,

xanthenyl group,

benzofuranyl group,

isobenzofuranyl group,

dibenzofuranyl group,

naphthobenzofuranyl group,

benzoxazolyl group,

benzoisoxazolyl group,

phenoxadinyl group,

morpholino group,

dinaphthofuranyl group,

azadibenzofuranyl group,

diazadibenzofuranyl group,

azanaphthobenzofuranyl group,

diazanaphthobenzofuranyl group

An unsubstituted heterocyclic group containing a sulfur atom:

thienyl group,

thiazolyl group,

isothiazolyl group,

thiadiazolyl group,

benzothiophenyl group,

isobenzothiophenyl group,

dibenzothiophenyl group,

naphthobenzothiophenyl group,

benzothiazolyl group,

benzoisothiazolyl group,

phenothiazinyl group,

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,

diphenylcarbazol-9-yl group,

phenylcarbazol-9-yl group,

methylbenzoimidazolyl group,

ethyl benzoimidazolyl 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]

A substituted heterocyclic group containing a sulfur atom:

phenyldibenzothiophenyl group,

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 heterocyclic ring containing at least one of a nitrogen atom, an oxygen atom and a sulfur atom and a ring-forming atom of the following unsubstituted heterocyclic ring A group in which a monovalent group derived by removing one bonded hydrogen atom 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 . provided _{that at least one of X A} and Y _A is an oxygen atom, a sulfur atom, or NH.

The heterocycles represented by the formulas (XY-1) to (XY-18) have a bond at an arbitrary position and become a monovalent heterocyclic group.

The fact that the monovalent group derived from the unsubstituted heterocycle represented by the formulas (XY-1) to (XY-18) has a substituent means that a hydrogen atom bonded to a carbon atom constituting the skeleton in these formulas is substituted with a substituent If present, or X _A or Y _A is NH or CH ₂ , it indicates a state in which a hydrogen atom in these NH or CH _{2 is substituted with a substituent.}

Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification include the following unsubstituted alkyl groups and substituted alkyl groups (herein, the unsubstituted alkyl group means "substituted or unsubstituted"). "alkyl group" refers to the case of "unsubstituted alkyl group", and the substituted alkyl group refers to the case where "substituted or unsubstituted alkyl group" is "substituted alkyl group"). Hereinafter, simply referred to as "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 of the group and the substituted alkyl group in which the following "unsubstituted alkyl group" has a substituent are exemplified. In addition, the examples of the "unsubstituted alkyl group" and the examples of the "substituted alkyl group" listed here are only examples, and in the "substituted alkyl group" described in this specification, the group in which the "unsubstituted alkyl group" has a substituent is a substituent A group further having , a group in which the "substituted alkyl group" further has a substituent, and the like are also included.

Unsubstituted alkyl groups:

methyl group,

ethyl group,

n-propyl group,

isopropyl group,

n-butyl group,

isobutyl group,

s-butyl group,

t-butyl group

A 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 this specification include the following unsubstituted alkenyl groups and substituted alkenyl groups (herein, the unsubstituted alkenyl group means A "substituted or unsubstituted alkenyl group" refers to a case in which the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group", and "a substituted alkenyl group" refers to a case in which the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group." ). Hereinafter, when simply referred to as "alkenyl group", both "unsubstituted alkenyl group" and "substituted alkenyl group" are included.

The "substituted alkenyl group" is a case where the "unsubstituted alkenyl group" has a substituent, and examples of a group and a substituted alkenyl group in which the following "unsubstituted alkenyl group" has a substituent are given. In addition, the examples of the "unsubstituted alkenyl group" and the examples of the "substituted alkenyl group" listed here are only examples, and in the "substituted alkenyl group" described in this specification, the "unsubstituted alkenyl group" is a substituent Groups in which the group having a group further has a substituent, a group in which the "substituted alkenyl group" further has a substituent, etc. are also included.

Unsubstituted alkenyl groups and substituted alkenyl groups:

vinyl,

Announcement,

1-butenyl group,

2-butenyl group,

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 this specification include the following unsubstituted alkynyl groups (herein, the unsubstituted alkynyl group means "substituted or unsubstituted"). refers to the case where "alkynyl group of" is "unsubstituted alkynyl group"). Hereinafter, when simply referred to as "alkynyl group", both "unsubstituted alkynyl group" and "substituted alkynyl group" are included.

The "substituted alkynyl group" is a case where the "unsubstituted alkynyl group" has a substituent, and the group etc. in which the following "unsubstituted alkynyl group" has a substituent are mentioned.

Unsubstituted alkynyl groups:

ethynyl group

Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group" described in this specification include the following unsubstituted cycloalkyl groups and substituted cycloalkyl groups (herein, the unsubstituted cycloalkyl group is The "substituted or unsubstituted cycloalkyl group" refers to the case of an "unsubstituted cycloalkyl group", and the substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group"). Hereinafter, when simply referred to as "cycloalkyl group", both "unsubstituted cycloalkyl group" and "substituted cycloalkyl group" are included.

The "substituted cycloalkyl group" is a case in which the "unsubstituted cycloalkyl group" has a substituent, and examples of a group in which the following "unsubstituted cycloalkyl group" has a substituent or a substituted cycloalkyl group are exemplified. In addition, the examples of the "unsubstituted cycloalkyl group" and the examples of the "substituted cycloalkyl group" listed here are only examples, and in the "substituted cycloalkyl group" described in this specification, "unsubstituted cycloalkyl group" is a substituent Groups in which the group having a group further has a substituent, a group in which the "substituted cycloalkyl group" further has a substituent, etc. are also included.

Unsubstituted aliphatic ring groups:

cyclopropyl group,

cyclobutyl group,

cyclopentyl group,

cyclohexyl group,

1-adamantyl group,

2-adamantyl group,

1-norbornyl group,

2-norbornyl group

A substituted cycloalkyl group:

4-methylcyclohexyl group

As a specific example (specific example group G7) of the group represented by -Si(R ₉₀₁ )(R ₉₀₂ )(R _{903 ) described herein,}

-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)

can be heard

here,

G1 is the "aryl group" described in the specific example group G1.

G2 is the "heterocyclic group" described in the specific example group G2.

G3 is the "alkyl group" described in the specific example group G3.

G5 is "alkynyl group" as described in specific example group G5.

G6 is the "cycloalkyl group" described in the specific example group G6.

As a specific example (specific example group G8) of the group represented by _{-O- (R 904} ) described in the present specification,

-O(G1),

-O(G2),

-O(G3),

-O(G6)

can be heard

here,

G1 is the "aryl group" described in the specific example group G1.

G2 is the "heterocyclic group" described in the specific example group G2.

G3 is the "alkyl group" described in the specific example group G3.

G6 is the "cycloalkyl group" described in the specific example group G6.

As a specific example (specific example group G9) of the group represented by _{-S- (R 905} ) described in the present specification,

-S(G1),

-S(G2),

-S(G3),

-S(G6)

can be heard

here,

G1 is the "aryl group" described in the specific example group G1.

G2 is the "heterocyclic group" described in the specific example group G2.

G3 is the "alkyl group" described in the specific example group G3.

G6 is the "cycloalkyl group" described in the specific example group G6.

As a specific example (specific example group G10) of the group represented by _{-N (R 906} ) (R ₉₀₇ ) described in the present specification,

-N(G1)(G1),

-N(G2)(G2),

-N(G1)(G2),

-N(G3)(G3),

-N(G6)(G6)

can be heard

here,

G1 is the "aryl group" described in the specific example group G1.

G2 is the "heterocyclic group" described in the specific example group G2.

G3 is the "alkyl group" described in the specific example group G3.

G6 is the "cycloalkyl group" described in the specific example group G6.

As a specific example (specific example group G11) of the "halogen atom" described in this specification, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. are mentioned.

A specific example of the "alkoxy group" described in this specification is a group represented by -O(G3), where G3 is the "alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, as long as otherwise specified herein.

A specific example of the "alkylthio group" described in this specification is a group represented by -S(G3), wherein G3 is the "alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, as far as otherwise stated in the present specification.

A specific example of the "aryloxy group" described in this specification is a group represented by -O(G1), where G1 is the "aryl group" described in the specific example group G1. The number of ring carbon atoms in the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, as far as otherwise specified herein.

A specific example of the "arylthio group" described in this specification is a group represented by -S(G1), where G1 is the "aryl group" described in the specific example group G1. The number of ring carbon atoms in the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified in the present specification.

Specific examples of the "aralkyl group" described herein are groups represented by -(G3)-(G1), wherein G3 is the "alkyl group" described in specific example group G3, and G1 is described in specific example group G1. It is an "aryl group". Therefore, the "aralkyl group" is an embodiment of the "substituted alkyl group" in which the "aryl group" is substituted. The number of carbon atoms in the "unsubstituted aralkyl group", which is an "unsubstituted alkyl group" in which the "unsubstituted aryl group" is substituted, is 7 to 50, preferably 7 to 30, and more Preferably it is 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.

The substituted or unsubstituted aryl group described in this specification is preferably a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl- 4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, phenanthryl group, pyrenyl group, chrysenyl group, triphenyl group nyl group, fluorenyl group, 9,9'-spirobifluorenyl group, 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, and benzo unless otherwise specified in the specification. imidazolyl group, phenanthrolinyl 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, naphthobenzoyl group Thiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, (9-phenyl)carbazolyl group ((9-phenyl)carbazol-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, diphenylcar Bazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, phenyldibenzothiophenyl group, indolocarbazolyl group , pyrazinyl group, pyridazinyl group, quinazolinyl group, cinnolinyl group, phthalazinyl group, quinoxalinyl group, pyrrolyl group, indolyl group, pyrrolo[3,2,1-jk]carbazolyl group, fura Nyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group, triazolyl group, oxazolyl group, benzoxazolyl group, thiazolyl group, benzothiazolyl group, Isothiazolyl group, benzisothiazolyl group, thiadiazolyl group, isoxazolyl group, benzisooxazolyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, imidazolidinyl group, indolo[ 3,2,1-jk] a carbazolyl group, a dibenzothiophenyl group, and the like.

The dibenzofuranyl group and the dibenzothiophenyl group are specifically any one of the following groups unless otherwise specified in the present specification.

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

The substituted or unsubstituted alkyl group described in this 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, etc., unless otherwise stated in the specification. .

The "substituted or unsubstituted arylene group" described in this specification refers to a group in which the "aryl group" is divalent unless otherwise specified. Specific examples (specific example group G12) of the "substituted or unsubstituted arylene group" include groups in which the "aryl group" described in the specific example group G1 is divalent. That is, a specific example (specific example group G12) of the "substituted or unsubstituted arylene group" is a group in which one hydrogen bonded to the ring-forming carbon of the "aryl group" described in specific example group G1 is removed.

Specific examples (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group" described in this specification include a group in which the "heterocyclic group" described in specific example group G2 is divalent. That is, a specific example (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group" is a group in which one hydrogen bonded to a ring-forming atom of the "heterocyclic group" described in specific example group G2 has been removed.

As a specific example (specific example group G14) of the "substituted or unsubstituted alkylene group" described in this specification, the group etc. which made the "alkyl group" described in specific example group G3 divalent are mentioned. That is, a specific example (specific example group G14) of the "substituted or unsubstituted alkylene group" is a group in which one hydrogen bonded to the carbon forming the alkane structure of the "alkyl group" described in specific example group G3 has been removed.

The substituted or unsubstituted arylene group described in this specification is preferably any of the following groups, unless otherwise specified in this specification.

In formulas (XY-20) to (XY-29), (XY-83) and (XY-84), R ₉₀₈ is a substituent.

m901 is an integer of 0 to 4, and when m901 is 2 or more, a plurality of R ₉₀₈ may be the same as or different from each other.

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

In formulas (XY-41) to (XY-46), R ₉₁₀ is a substituent.

m902 is an integer from 0 to 6. When m902 is 2 or more, two or more R ₉₁₀ may be the same as or different from each other.

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

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

In the formulas (XY-65) to (XY-75), X _B represents an oxygen atom or a sulfur atom.

In the present specification, in the case of "adjacent two or more sets of one or more bonds with each other to form a substituted or unsubstituted saturated or unsaturated ring", the parent skeleton is an anthracene ring: XY-80 Anthracene compound represented by ) will be described as an example.

For example, R ₉₂₁ ~R 2 gaeran adjacent pair of first couple of cases, "to form a ring adjacent two or more than one tank is bonded to each other" in the _930, 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 .

Said "one or more sets" means that two or more sets of said adjacent two sets may form a ring simultaneously. 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, it is represented by the following formula (XY-81).

When "at least two adjacent" form a ring, for example, R ₉₂₁ and R ₉₂₂ combine with each other to form Ring A, R ₉₂₂ and R ₉₂₃ combine with each other to form Ring C, and R ₉₂₁ to _{R 923} When the three adjacent to each other _{form the ring A and the ring C which share R 922} condensed on the anthracene parent skeleton, they are represented by the following formula (XY-82).

Rings A to C formed in the formulas (XY-81) and (XY-82) are saturated or unsaturated rings.

An "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 the above formula (XY-81), ring A formed by bonding _{R 921} and R ₉₂₂ to each other is a carbon atom of an anthracene skeleton to which _{R 921} is bonded, a carbon atom of an anthracene skeleton to which _{R 922 is bonded;} It means a ring formed by one or more arbitrary elements. As a specific example, when R ₉₂₁ and R ₉₂₂ form ring A, 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 4 carbon atoms are unsaturated When forming a ring, the ring formed by R ₉₂₁ and R ₉₂₂ becomes a benzene ring. Moreover, when forming a saturated ring, it becomes a cyclohexane ring.

Here, the "arbitrary element" is preferably a C element, an N element, an O element, or an S element. In an arbitrary element (for example, in the case of a C element or an N element), a bond not involved 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 C element is included, the ring formed becomes a heterocyclic ring.

The number of "one or more arbitrary elements" constituting the saturated or unsaturated ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, still more preferably 3 or more and 5 or less.

As a specific example of an aromatic hydrocarbon ring, the structure in which the aryl group mentioned as a specific example in specific example group G1 was terminated with the hydrogen atom is mentioned.

As a specific example of an aromatic heterocycle, the structure in which the aromatic heterocyclic group mentioned as a specific example in specific example group G2 was terminated with the hydrogen atom is mentioned.

As a specific example of an aliphatic hydrocarbon ring, the structure in which the cycloalkyl group mentioned as a specific example in specific example group G6 was terminated with the hydrogen atom is mentioned.

When the above-described "saturated or unsaturated ring" has a substituent, the substituent is, for example, an "optional substituent" described later. Specific examples of the substituent when the above-mentioned "saturated or unsaturated ring" has a substituent are the substituents described in the above-mentioned "Substituents described in this specification" section.

In one embodiment in the present specification, the substituent in the case of "substituted or unsubstituted" (hereinafter, may be referred to as "optional substituent") is,

an unsubstituted C1-C50 alkyl group;

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 ring carbon atoms;

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ )

(here,

R ₉₀₁ to _{R 907} are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms;

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R ₉₀₁ ~R ₉₀₇ a, if present more than one, each of the two or more R ₉₀₁ ~R ₉₀₇ may be subjected to may be the same different.),

Halogen atom, cyano group, nitro group,

an unsubstituted aryl group having 6 to 50 ring carbon atoms, and

Unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms

It is a group selected from the group consisting of.

In one embodiment, the substituent in the case of said "substituted or unsubstituted" is

an alkyl group having 1 to 50 carbon atoms;

an aryl group having 6 to 50 ring carbon atoms, and

A monovalent heterocyclic group having 5 to 50 ring atoms

It is a group selected from the group consisting of.

In one embodiment, the substituent in the case of said "substituted or unsubstituted" is

an alkyl group having 1 to 18 carbon atoms;

an aryl group having 6 to 18 ring carbon atoms, and

A monovalent heterocyclic group having 5 to 18 ring atoms

It is a group selected from the group consisting of.

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

In the present specification, unless otherwise specified, adjacent arbitrary substituents form a saturated or unsaturated ring (preferably a substituted or unsubstituted saturated or unsaturated 5-membered ring or 6-membered ring, more preferably a benzene ring) also good

In this specification, unless otherwise indicated, arbitrary substituents may have a substituent further. As a substituent which an arbitrary substituent further has, the thing similar to the said arbitrary substituent is mentioned.

[New compound]

The compound according to one embodiment of the present invention is represented by the following formula (1).

(in formula (1),

R ₁ to _{R 8} are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

R ₉₀₁ to _{R 907} are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms;

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

R ₉₀₁ ~R ₉₀₇ a, if present more than one, each of the two or more R ₉₀₁ ~R ₉₀₇ may be subjected to may be the same different.

At least one of R ₁ to _{R 8} is a deuterium atom.

Adjacent two or more of R ₁ to _{R 4} and adjacent two or more of R ₅ to _{R 8} are not bonded to each other to form a ring.

L ₁ and L ₂ are each independently

single bond,

A substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

It is a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

Ar ₁ is

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

Ar ₂ is a monovalent group represented by the following formula (2), (3) or (4).

In formulas (2) to (4),

One or more pairs of adjacent two of R ₁₅ to _{R 20} combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

When _{one or more pairs of adjacent two of R 15} to _{R 20} combine with each other to not form a substituted or unsubstituted saturated or unsaturated ring, one of _{R 13} to _{R 20} is a single bond bonded to _{L 2 .}

When _{one or more pairs of adjacent R 15} to _{R 20} combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, R ₁₅ to R which does not form the substituted or unsubstituted saturated or unsaturated ring ₂₀ , and one of R ₁₃ and R ₁₄ is a single bond bonded to _{L 2 .}

_{R 13} to _{R 20} , and R ₁₁ and R ₁₂ which do not form the substituted or unsubstituted saturated or unsaturated ring and are not a single bond bonded to _{L 2} are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is 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).)

When the compound according to an aspect of the present invention has the above-described structure, it becomes possible to improve device performance when used as an organic EL device. Specifically, it becomes possible to provide an organic EL device having a longer lifespan.

In addition, according to one aspect of the present invention, it is possible to provide a method for improving the performance of an organic EL device, characterized in that the compound is used in the light emitting layer of the organic EL device. Specifically, the method uses, as a host material, a compound having the same structure as the compound represented by Formula (1) (hereinafter also referred to as "light hydrogen body") except that it contains only light hydrogen atoms as hydrogen atoms. Compared with the case, it becomes possible to improve the organic EL device performance. In the case of using a light hydrogen body, substantially only the light hydrogen body as the host material in the light emitting layer [the ratio of the content of the light hydrogen body to the total of the compound represented by Formula (1) and the light hydrogen body is 90 mol% or more, 95 mol% or more or 99 mol% or more].

That is, as a host material, in place of or in addition to a light hydrogen body, a compound in which at least one of the light hydrogen atoms on the anthracene skeleton among the light hydrogen atoms of the light hydrogen body is substituted with a deuterium atom [a compound represented by the formula (1)] By using it, the said performance can be improved.

All of R ₁ to _{R 8} may be deuterium atoms, or a part (eg, one or two or more) may be deuterium atoms.

_{R 1} to _{R 8} that are not deuterium atoms are preferably hydrogen atoms (light hydrogen atoms).

In one embodiment, at least one of the hydrogen atoms of one or more selected from the group consisting of _{L 1} and L _{2 is a deuterium atom.} Specifically, in one embodiment _{, at least one selected from the group consisting of L 1} and L ₂ is an unsubstituted arylene group having 6 to 30 ring carbon atoms in which at least one of the hydrogen atoms is a deuterium atom, or a hydrogen atom. an unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, at least one of which is a deuterium atom.

In one embodiment, L ₁ and L ₂ are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms. Preferably, at least one of _{L 1} and L _{2 is a single bond.}

_{In one embodiment, R 13} or R ₁₄ in Formulas (2) to (4) is a single bond bonded to _{L 2 .}

_{In one embodiment, one or more pairs of adjacent two of R 15} to _{R 20} in formulas (2) to (4) do not combine with each other to form a substituted or unsubstituted saturated or unsaturated ring.

In one embodiment, among _{R 11} to _{R 20} in Formulas (2) to (4), it is a hydrogen atom that is not a single bond bonded to _{L 2 and does not contribute to ring formation either.}

In one embodiment, among _{R 11} to _{R 20} in formulas (2) to (4), at least one of those that is not a single bond bonded to _{L 2 and does not contribute to ring formation is a deuterium atom.}

In one embodiment, at least one of the hydrogen atoms which one or more of _{Ar 1 has is a deuterium atom.} Specifically, in one embodiment, Ar ₁ is an unsubstituted aryl group having 6 to 50 ring carbon atoms in which at least one of the hydrogen atoms is a deuterium atom, or an unsubstituted ring in which at least one of the hydrogen atoms is a deuterium atom. It is a monovalent heterocyclic group having 5 to 50 forming atoms.

Ar ₁ is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, more preferably selected from groups represented by the following formulas (a1) to (a4).

(In formulas (a1) to (a4), * is a single bond bonded to _{L 1 .}

R ₂₁ is each independently

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is 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).

m1 is an integer of 0-4 each independently.

m2 is an integer of 0-5 each independently.

m3 is each independently an integer of 0-7.

When each of m1 to m3 is 2 or more, a plurality of R ₂₁ may be the same as or different from each other.

When each of m1 to m3 is 2 or more, a plurality of adjacent R ₂₁ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring is not formed.)

The presence of a deuterium atom in the compound ^{is confirmed by mass spectrometry or 1} H-NMR analysis. In addition, the bonding position of the deuterium atom in a compound ^{is specified by <1>} H-NMR analysis. Specifically, it is as follows.

Mass spectrometry was performed on the target compound, and the molecular weight increased by 1 compared to the corresponding compound in which all hydrogen atoms were light hydrogen atoms, so that it could be confirmed that one deuterium atom was included. In addition, the heavy hydrogen atom is ¹ because H-NMR analysis a signal does not come in, it is possible to determine the number of deuterium atoms contained in the molecule by the integral value obtained by performing the ¹ H-NMR analysis for the subject compounds. Moreover, the binding position of a deuterium atom can be specified by performing <^1> H-NMR analysis with respect to a target compound and attributing a signal.

The composition in one aspect of the present invention contains the compound represented by Formula (1), and the content ratio of the latter to the total of the compound represented by Formula (1) and the light hydrogen is 99 mol% or less. The light hydrogen body content ratio is confirmed by mass spectrometry.

Moreover, in the composition in one aspect of the present invention, the content ratio of electrons with respect to the total of the compound represented by formula (1) and the light hydrogen is 30 mol% or more, 50 mol% or more, 70 mol% or more, 90 mol % or more, 95 mol% or more, 99 mol% or more, or 100 mol%.

In one embodiment, the compound represented by Formula (1) is the following Formula (1-1), (1-2), (1-3), (1-4), (1-5) or (1- It is a compound represented by 6).

(In formulas (1-1), (1-2), (1-3), (1-4), (1-5) and (1-6), R ₁ to _{R 8} , R ₁₁ to _{R 20} , Ar ₁ , L ₁ and L ₂ are as defined in Formula (1).)

In one embodiment, the compound represented by formula (1) is the following formula (1-11), (1-12), (1-13), (1-14), (1-15) or (1- 16) is a compound represented by

(in formulas (1-11), (1-12), (1-13), (1-14), (1-15) and (1-16), R ₁ to _{R 8} , Ar ₁ and L ₁ is as defined in Equation (1) above.)

In one embodiment, the compound represented by formula (1) is the following formula (1-21), (1-22), (1-23), (1-24), (1-25) or (1- 26) is a compound represented by

(In formulas (1-21), (1-22), (1-23), (1-24), (1-25) and (1-26), Ar ₁ and L ₁ are represented by Formula (1) as defined in .)

The compound represented by Formula (1) can be synthesized according to the synthesis method described in Examples, by using known substitution reactions or raw materials tailored to the target substance.

Examples of compounds according to one aspect of the present invention are shown below. In the following specific examples, D represents a deuterium atom.

The compound described above can be used as a material for an organic EL device, preferably as a host material for a light emitting layer.

[Organic EL device]

The organic EL device according to an aspect of the present invention has a cathode, an anode, and one or two or more organic layers disposed between the cathode and the anode, and the organic layer is a compound represented by Formula (1) or the composition of the present invention described above. contains A conventionally well-known material and element structure can be applied for an organic layer, unless the effect of this invention is impaired except for containing the compound represented by Formula (1) or the composition of said this invention. The above-described organic EL device preferably contains a compound in which the light emitting layer of the organic layer is represented by the formula (1) or the composition of the present invention described above.

In one embodiment, the light emitting layer of the organic EL device according to an aspect of the present invention contains the compound represented by Formula (1) and a light hydrogen body, and the content ratio of the latter to the total is 99 mol% or less.

Further, in one embodiment, the light emitting layer of the organic EL device according to an aspect of the present invention contains the compound represented by Formula (1) and a light hydrogen body, and the content ratio of electrons to the total is 30 mol% or more , 50 mol% or more, 70 mol% or more, 90 mol% or more, 95 mol% or more, 99 mol% or more, or 100 mol%.

In one aspect of the organic EL device of the present invention, it is preferable to have a hole transport layer between the anode and the light emitting layer.

In one aspect of the organic EL device of the present invention, it is preferable to have an electron transporting layer between the cathode and the light emitting layer.

A typical element configuration of the organic EL element of the present invention is

(1) anode/light emitting layer/cathode

(2) anode/hole injection layer/light emitting layer/cathode

(3) anode/light emitting layer/electron injection/transport layer/cathode

(4) anode/hole injection layer/light emitting layer/electron injection/transport layer/cathode

(5) anode/organic semiconductor layer/light emitting layer/cathode

(6) anode/organic semiconductor layer/electron barrier layer/light emitting layer/cathode

(7) anode/organic semiconductor layer/light emitting layer/adhesion improvement layer/cathode

(8) anode/hole injection/transport layer/light emitting layer/electron injection/transport layer/cathode

(9) anode/insulating layer/light emitting layer/insulating layer/cathode

(10) anode/inorganic semiconductor layer/insulating layer/light emitting layer/insulating layer/cathode

(11) anode/organic semiconductor layer/insulating layer/light emitting layer/insulating layer/cathode

(12) anode/insulating layer/hole injection/transport layer/light-emitting layer/insulating layer/cathode

(13) anode/insulating layer/hole injection/transport layer/light emitting layer/electron injection/transport layer/cathode

Structures, such as these are mentioned.

Although the structure of (8) is used preferably among the above, it is not limited to these.

In the present specification, "hole injection/transport layer" means "at least one of a hole injection layer and a hole transport layer", and "electron injection/transport layer" means "at least one of an electron injection layer and an electron transport layer".

The light emitting layer is preferably, in addition to the compound (host material) represented by the formula (1), the following formulas (11), (21), (31), (41), (51), (61), (71) ) and at least one compound (dopant material) selected from the group consisting of (81).

(Compound represented by Formula (11))

The compound represented by Formula (11) is demonstrated.

[In formula (11),

One or more pairs of two or more adjacent to each other among R ₁₀₁ to _{R 110} do not form a substituted or unsubstituted saturated or unsaturated ring or a substituted or unsubstituted saturated or unsaturated ring by combining them.

At least one of R ₁₀₁ to _{R 110} is a monovalent group represented by the following formula (12).

_{R 101} to _{R 110} which do not form the substituted or unsubstituted saturated or unsaturated ring and are not a monovalent group represented by the following formula (12) are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is 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 formula (12), Ar ₁₀₁ and Ar ₁₀₂ are each independently

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

L _{101 to L 103} are each independently

single bond,

A substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

It is a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.)]

In Formula (11), _{it is preferable that two of R 101 - R 110} are groups represented by Formula (12).

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

(In Formula (13), R ₁₁₁ to _{R 118} are the same as _{R 101} to _{R 110 which} is not a monovalent group represented by Formula (12) in Formula (11) _{. Ar 101} , Ar ₁₀₂ , L ₁₀₁ , L ₁₀₂ and L ₁₀₃ are as defined in the above formula (12).)

In formula (11) _{, it is preferable that L 101} is a single bond, and it is preferable that L ₁₀₂ and L ₁₀₃ are a single bond.

In one embodiment, the compound represented by formula (11) is represented by the following formula (14) or (15).

(In Formula (14), R ₁₁₁ to _{R 118} are as defined in Formula (13). Ar ₁₀₁ , Ar ₁₀₂ , L ₁₀₂ and L ₁₀₃ are as defined in Formula (12).)

(In Formula (15), R ₁₁₁ to _{R 118} are as defined in Formula (13). Ar ₁₀₁ and Ar ₁₀₂ are as defined in Formula (12).)

In the formulas (11) and (12), preferably _{, at least one of Ar 101} and Ar ₁₀₂ is a group represented by the following formula (16).

(in formula (16),

X ₁₀₁ represents an oxygen atom or a sulfur atom.

Among R ₁₂₁ to _{R 127} , at least one pair of adjacent two or more are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring is not formed.

_{R 121} to _{R 127} which do not form the substituted or unsubstituted saturated or unsaturated ring are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

R ₉₀₁ to _{R 907} are as defined in Formula (1) above.)

X ₁₀₁ is preferably an oxygen atom.

At least one of R ₁₂₁ to _{R 127 is,}

A substituted or unsubstituted C1-C50 alkyl group;

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 carbon atoms;

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

It is preferable that it is a substituted or unsubstituted monovalent heterocyclic group of 5-50 ring atoms.

In the formulas (11) and (12), _{it is preferable that Ar 101} is a group represented by the formula (16), and Ar ₁₀₂ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, the compound represented by Formula (11) is represented by the following Formula (17).

(In Formula (17), R ₁₁₁ to _{R 118} are as defined in Formula (13) above. R ₁₂₁ to _{R 127} are as defined in Formula (16).

R ₁₃₁ to _{R 135} are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

R ₉₀₁ to _{R 907} are as defined in Formula (1) above.)

As a compound represented by Formula (11), the compound shown below is mentioned as a specific example, for example. In the following specific examples, Me represents a methyl group.

(Compound represented by Formula (21))

The compound represented by Formula (21) is demonstrated.

(In formula (21),

each Z is independently CR _a or N.

A1 ring and A2 ring are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

When R _a multiple presence, the plurality of R and _a 2 more than one set or more adjacent ones are bonded to each other substituted or unsubstituted, saturated or forms a ring having an unsaturated, or the chain of a saturated or unsaturated, substituted or unsubstituted does not form

When R _b is a plurality is present, more than one trillion or more adjacent ones of the plurality of R _b are bonded to each other or form a ring, saturated or unsaturated, substituted or unsubstituted, or a cyclic saturated or unsaturated substituted or unsubstituted does not form

When R _c has a plurality is present, adjacent ones of the plurality of R _c 2 at least one set or more are bonded to each other or form a ring, saturated or unsaturated, substituted or unsubstituted, or a cyclic saturated or unsaturated substituted or unsubstituted does not form

n21 and n22 are each independently an integer of 0-4.

_{R a} to _{R c} that do not form a substituted or unsubstituted saturated or unsaturated ring are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

R ₉₀₁ to _{R 907} are as defined in Formula (1) above.)

The "aromatic hydrocarbon ring" of ring A1 and ring A2 has the same structure as the compound which introduce|transduced the hydrogen atom into the "aryl group" mentioned above. The "aromatic hydrocarbon ring" of the A1 ring and the A2 ring contains two carbon atoms on the central condensed bicyclic structure of the formula (21) as ring forming atoms. As a specific example of "a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms", the compound etc. which introduce|transduced the hydrogen atom into the "aryl group" described in specific example group G1 are mentioned.

The "heterocycle" of the A1 ring and the A2 ring has the same structure as the compound in which a hydrogen atom is introduced into the above-mentioned "heterocyclic group". The "heterocycle" of the A1 ring and the A2 ring includes two carbon atoms on the central condensed bicyclic structure of the formula (21) as ring forming atoms. As a specific example of "a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms", the compound etc. which introduce|transduced the hydrogen atom into the "heterocyclic group" described in specific example group G2 are mentioned.

R _b is bonded to any one of the carbon atoms forming the aromatic hydrocarbon ring of the A1 ring or any one of the atoms forming the heterocyclic ring of the A1 ring.

R _c is bonded to any one of the carbon atoms forming the aromatic hydrocarbon ring of the A2 ring or any one of the atoms forming the heterocyclic ring of the A2 ring.

At least one (preferably two) of R _a to _{R c} is preferably a group represented by the following formula (21a).

-L ₂₀₁ -Ar ₂₀₁ (21a)

(in formula (21a),

L ₂₀₁ silver

single bond,

A substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

It is a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

Ar ₂₀₁ is

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;

A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or

It is group represented by following formula (21b).

(in formula (21b),

L ₂₁₁ and L ₂₁₂ are each independently

single bond,

A substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

It is a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

Ar ₂₁₁ and Ar ₂₁₂ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

_{Ar 211} and Ar ₂₁₂ that do not form a substituted or unsubstituted saturated or unsaturated ring are each independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.))

In one embodiment, the compound represented by Formula (21) is represented by the following Formula (22).

(In formula (22),

One or more sets of two or more adjacent to each other among R ₂₀₁ to _{R 211} do not form a substituted or unsubstituted saturated or unsaturated ring or a substituted or unsubstituted saturated or unsaturated ring when combined with each other.

_{R 201} to _{R 211} which do not form the substituted or unsubstituted saturated or unsaturated ring are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

R ₉₀₁ to _{R 907} are as defined in Formula (1) above.)

At least one (preferably two) of R ₂₀₁ to _{R 211} is preferably a group represented by the above formula (21a). Preferably, R ₂₀₄ and R ₂₁₁ are groups represented by the above formula (21a).

In one embodiment, the compound represented by the formula (21) is a compound in which a structure represented by the following formula (21-1) or (21-2) is bonded to the A1 ring. In one embodiment, the compound represented by the formula (22) is a compound in which a structure represented by the following formula (21-1) or (21-2) is bonded to a ring to which _{R 204} to _{R 207 are bonded.}

(In the formula (21-1), the two number of bonds * are each independently bonded to the ring-forming carbon atom of the aromatic hydrocarbon ring of the A1 ring of the formula (21) or the ring-forming atom of the heterocyclic ring, or It binds to any one of _{R 204} to _{R 207.}

The three number of bonds * in the formula (21-2) are each independently bonded to a ring-forming carbon atom or a heterocyclic ring-forming atom of the aromatic hydrocarbon ring of the A1 ring of the formula (21), or R ₂₀₄ to binds to any one of R _207.

At _{least one pair of adjacent two or more of R 221} to _{R 227} and R ₂₃₁ to _{R 239} is combined with each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring I never do that.

_{R 221} to _{R 227} and R ₂₃₁ to _{R 239} which do not form the substituted or unsubstituted saturated or unsaturated ring are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

R ₉₀₁ to _{R 907} are as defined in Formula (1) above.)

In one embodiment, the compound represented by Formula (21) is a compound represented by the following Formula (21-3), Formula (21-4), or Formula (21-5).

(in Formula (21-3), Formula (21-4) and Formula (21-5),

Ring A1 is as defined in Formula (21).

R ₂₄₀₁ to _{R 2407} are the same as _{R 221} to _{R 227} in formulas (21-1) and (21-2). R ₂₄₁₀ to _{R 2417} are the same as _{R 201} to _{R 211} in Formula (22). Two R ₂₄₁₇ may be the same as or different from each other.)

In one embodiment, the substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms in the A1 ring of the formula (21-5) is a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted fluorene ring .

In one embodiment, the substituted or unsubstituted heterocycle having 5 to 50 ring atoms in the A1 ring of formula (21-5) is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carba It is a sol ring or a substituted or unsubstituted dibenzothiophene ring.

In one embodiment, the compound represented by the formula (21) or (22) is selected from the group consisting of compounds represented by the following formulas (21-6-1) to (21-6-7).

(in formulas (21-6-1) to (21-6-7),

R ₂₄₂₁ to _{R 2427} are the same as _{R 221} to _{R 227} in formulas (21-1) and (21-2). R ₂₄₃₀ to _{R 2437} and R ₂₄₄₁ to _{R 2444} are the same as _{R 201} to _{R 211} in Formula (22).

X is O, NR ₉₀₁ , or C(R ₉₀₂ )(R ₉₀₃ ).

R ₉₀₁ to _{R 903} are as defined in Formula (1) above.)

In one embodiment, in the compound represented by the formula (22), _{one or more pairs of two or more adjacent to each other among R 201} to _{R 211} are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring. The said embodiment is demonstrated in detail as Formula (25) below.

(Compound represented by Formula (25))

The compound represented by Formula (25) is demonstrated.

(in formula (25),

R ₂₅₁ and R ₂₅₂ , R ₂₅₂ and R ₂₅₃ , R ₂₅₄ and R ₂₅₅ , R ₂₅₅ and R ₂₅₆ , R ₂₅₆ and R ₂₅₇ , R ₂₅₈ and R ₂₅₉ , R ₂₅₉ and R ₂₆₀ and R ₂₆₀ and R ₂₆₁ At least two of the pairs selected from are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring.

provided _{that a pair consisting of R 251} and R ₂₅₂ and a pair consisting of R ₂₅₂ and R ₂₅₃ ; a pair consisting of R ₂₅₄ and R ₂₅₅ and a pair consisting of R ₂₅₅ and R ₂₅₆ ; a pair consisting of R ₂₅₅ and R ₂₅₆ and a pair consisting of R ₂₅₆ and R ₂₅₇ ; a pair consisting of R ₂₅₈ and R ₂₅₉ and a pair consisting of R ₂₅₉ and R ₂₆₀ ; And _{the pair consisting of R 259} and R ₂₆₀ and the pair consisting of R ₂₆₀ and R ₂₆₁ do not form a ring at the same time.

The _{two or more rings formed by R 251} to _{R 261} may be the same or different.

_{R 251} to _{R 261} which do not form a substituted or unsubstituted saturated or unsaturated ring are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

R ₉₀₁ to _{R 907} are as defined in Formula (1) above.)

In formula (25), R _n and R _n+1 (n represents an integer selected from 251, 252, 254 to 256, and 258 to 260) are bonded to each other to form R _n and R _n+1 Together with the two ring-forming carbon atoms, they form a substituted or unsubstituted, saturated or unsaturated ring. The ring is preferably composed of an atom selected from a C atom, an O atom, an S atom and an N atom, and the number of atoms is preferably 3 to 7, more preferably 5 or 6.

The number of the above-described ring structures in the compound represented by formula (25) is, for example, 2, 3, or 4. Two or more ring structures may exist on the same benzene ring on the mother skeleton of Formula (25), respectively, and may exist on different benzene rings. For example, when it has three ring structures, one ring structure may exist in each of the three benzene rings of Formula (25).

Examples of the above-described ring structure in the compound represented by the formula (25) include structures represented by the following formulas (251) to (260).

(In formulas (251) to (257), *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12 and *13 and *14 each represent _{the above two ring-forming carbon atoms to which R n} and R _n+1 are bonded, and the ring-forming carbon atoms to which R _n is bonded are *1 and *2, *3 and *4, *5 and Either of the two ring-forming carbon atoms represented by *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14 may be used.

X ₂₅₀₁ is C(R ₂₅₁₂ )(R ₂₅₁₃ ), NR ₂₅₁₄ , O or S.

One or more sets of two or more adjacent to each other among R ₂₅₀₁ to _{R 2506} and R ₂₅₁₂ to _{R 2513} combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring I never do that.

_{R 2501} to _{R 2514} which do not form a substituted or unsubstituted saturated or unsaturated ring are the same as _{R 251} to _{R 261 above.)}

(In formulas (258) to (260), *1 and *2, and *3 and *4 each represent the two ring-forming carbon atoms to which _{R n} and R _{n+1 are bonded, and R n} is bonded to each other. The ring-forming carbon atoms to be used may be either of the two ring-forming carbon atoms represented by *1 and *2 or *3 and *4.

X ₂₅₀₁ is C(R ₂₅₁₂ )(R ₂₅₁₃ ), NR ₂₅₁₄ , O or S.

At _{least one pair of adjacent two or more of R 2515} to _{R 2525} does not form a substituted or unsubstituted saturated or unsaturated ring or a substituted or unsubstituted saturated or unsaturated ring by combining them with each other.

_{R 2515} to _{R 2521} and R ₂₅₂₂ to _{R 2525} which do not form a substituted or unsubstituted saturated or unsaturated ring are the same as _{R 251} to _{R 261 above.)}

In formula (25), _{at least one of R 252} , R ₂₅₄ , R ₂₅₅ , R ₂₆₀ and R ₂₆₁ (preferably at least one of R ₂₅₂ , R ₂₅₅ and R ₂₆₀ , more preferably R ₂₅₂ ) is a ring It is preferable if it is group which does not form a structure.

(i) a substituent when the ring structure formed by _{R n} and R _n+1 in the formula (25) has a substituent;

_{(ii) R 251} to _{R 261} which do not form a ring structure in the formula (25), and

_{(iii) R 2501} to _{R 2514} and R ₂₅₁₅ to _{R 2525} in formulas (251) to (260) are preferably each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 carbon atoms;

-N (R ₉₀₆ ) (R ₉₀₇ ),

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;

Either a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or a group selected from the following group.

(In formulas (261) to (264), R _d is each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

X is C(R ₉₀₁ )(R ₉₀₂ ), NR ₉₀₃ , O or S.

R ₉₀₁ to _{R 907} are as defined in the above formula (1).

p1 is each independently an integer from 0 to 5, p2 is each independently an integer from 0 to 4, p3 is an integer from 0 to 3, and p4 is an integer from 0 to 7.)

In one embodiment, the compound represented by formula (25) is represented by any one of the following formulas (25-1) to (25-6).

(In Formulas (25-1) to (25-6), rings d to i are each independently a substituted or unsubstituted saturated or unsaturated ring. R ₂₅₁ to _{R 261} are the same as in Formula (25). .)

In one embodiment, the compound represented by formula (25) is represented by any one of the following formulas (25-7) to (25-12).

(In formulas (25-7) to (25-12), rings d to f, k and j are each independently a substituted or unsubstituted saturated or unsaturated ring. R ₂₅₁ to _{R 261} are represented by the formula (25 ) is the same as

In one embodiment, the compound represented by formula (25) is represented by any one of the following formulas (25-13) to (25-21).

(In Formulas (25-13) to (25-21), rings d to k are each independently a substituted or unsubstituted saturated or unsaturated ring. R ₂₅₁ to _{R 261} are the same as in Formula (25). .)

As a substituent when the ring g or h further has a substituent, for example,

A substituted or unsubstituted C1-C50 alkyl group;

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

and groups represented by the formulas (261), (263) or (264).

In one embodiment, the compound represented by formula (25) is represented by any one of the following formulas (25-22) to (25-25).

(In formulas (25-22) to (25-25), X ₂₅₀ is each independently C(R ₉₀₁ )(R ₉₀₂ ), NR ₉₀₃ , O or S. R ₂₅₁ to _{R 261} , R ₂₇₁ to R ₂₇₈ is the same as _{R 251} to _{R 261 in} Formula (25) _{. R 901 to R 903} are as defined in Formula (1).)

In one embodiment, the compound represented by Formula (25) is represented by the following Formula (25-26).

(In formula (25-26), X ₂₅₀ is C(R ₉₀₁ )(R ₉₀₂ ), NR ₉₀₃ , O or S. R ₂₅₃ , R ₂₅₄ , R ₂₅₇ , R ₂₅₈ , R ₂₆₁ and R ₂₇₁ to R ₂₈₂ is the same as _{R 251} to _{R 261 in} Formula (25) _{. R 901 to R 903} are as defined in Formula (1).)

As a compound represented by Formula (21), the compound shown below is mentioned as a specific example, for example. In the following specific examples, Me represents a methyl group.

(Compound represented by Formula (31))

The compound represented by Formula (31) is demonstrated. The compound represented by Formula (31) is a compound corresponding to the compound represented by Formula (21-3) mentioned above.

(in formula (31),

At _{least one pair of adjacent two or more of R 301} to _{R 307} and R ₃₁₁ to _{R 317} does not form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring .

_{R 301} to _{R 307} and R ₃₁₁ to _{R 317} which do not form a substituted or unsubstituted saturated or unsaturated ring are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

R ₃₂₁ and R ₃₂₂ are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

R ₉₀₁ to _{R 907} are as defined in Formula (1) above.)

"A set _{of two or more adjacent among R 301} to _{R 307} and R ₃₁₁ to _{R 317} " is, for example, R ₃₀₁ and R ₃₀₂ , R ₃₀₂ and R ₃₀₃ , R ₃₀₃ and R ₃₀₄ , R ₃₀₅ and R ₃₀₆ , R ₃₀₆ and It is a combination of _{R 307} , R ₃₀₁ and R ₃₀₂ and R _{303 .}

In one embodiment, at least one, preferably two _{, of R 301} to _{R 307} and R ₃₁₁ to _{R 317} is a group represented by _{-N(R 906} )(R _{907 ).}

In one embodiment, R ₃₀₁ to _{R 307} and R ₃₁₁ to _{R 317} are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring forming atom 5 It is a monovalent heterocyclic group of -50.

In one embodiment, the compound represented by Formula (31) is a compound represented by the following Formula (32).

(In formula (32),

At _{least one pair of adjacent two or more of R 331} to _{R 334} and R ₃₄₁ to _{R 344} does not form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring .

_{R 331} to _{R 334} , R ₃₄₁ to _{R 344} , and R ₃₅₁ and R ₃₅₂ that do not form the substituted or unsubstituted saturated or unsaturated ring are each independently

hydrogen atom,

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

R ₃₆₁ to _{R 364} are each independently

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.)

In one embodiment, the compound represented by Formula (31) is a compound represented by the following Formula (33).

(In Formula (33), R ₃₅₁ , R ₃₅₂ and R ₃₆₁ to _{R 364} are as defined in Formula (32).)

In one embodiment, the compound represented by Formula (31) is a compound represented by the following Formula (34) or (35).

(in formulas (34) and (35),

R ₃₆₁ to _{R 364} are as defined in the above formula (32).

At _{least one pair of adjacent two or more of R 371} to _{R 377} and R ₃₈₀ to _{R 386} does not form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring .

_{R 371} to _{R 377} and R ₃₈₀ to _{R 386} , and R ₃₈₇ which do not form the substituted or unsubstituted saturated or unsaturated ring are each independently

hydrogen atom,

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. Two R ₃₈₇ may be the same as or different from each other.)

In one embodiment, the compound represented by Formula (31) is a compound represented by the following Formula (34-2) or (35-2).

(In formulas (34-2) and (35-2), R ₃₆₁ to _{R 364} , R ₃₇₅ to _{R 377} and R ₃₈₄ to _{R 387} are as defined in the formulas (34) and (35) above.)

_{In one embodiment, R 361} to _{R 364} in formulas (32), (33), (34), (35), (34-2) and (35-2) are each independently substituted or unsubstituted of an aryl group having 6 to 50 ring carbon atoms (preferably a phenyl group).

In one embodiment, R ₃₂₁ and R ₃₂₂ in Formula (31), Formulas (32), (33), (34), (35), (34-2), (35-2) R ₃₅₁ and R ₃₅₂ are each independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms (preferably a phenyl group).

In one embodiment, the compound represented by Formula (31) is a compound represented by the following Formula (36).

(In formula (36), one or more sets of two or more adjacent among _{R 3001} , R ₃₀₀₂ , R ₃₀₀₅ to _{R 3007} , R ₃₀₁₀ , R ₃₀₁₁ , R ₃₀₁₄ to _{R 3016} , and R ₃₀₃₁ to _{R 3034 are bonded to each other} It does not form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring.

each X _a is independently selected from O, S and N(R ₃₅ ).

R ₃₅ is _{bonded to R 3031} to form a substituted or unsubstituted saturated or unsaturated ring, or does not form the ring.

_{R 3001} , R ₃₀₀₂ , R ₃₀₀₅ to _{R 3007} , R ₃₀₁₀ , R ₃₀₁₁ , R ₃₀₁₄ to _{R 3016} , and R ₃₀₃₁ to _{R 3035} , and R ₃₀₂₁ , which do not form the substituted or unsubstituted saturated or unsaturated ring; R ₃₀₂₂ are each independently

hydrogen atom,

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.)

In one embodiment, the substituent in the case of "substituted or unsubstituted" in formulas (31) to (36) is

A substituted or unsubstituted C1-C50 alkyl group;

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 carbon atoms;

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

As a compound represented by Formula (31), the compound shown below is mentioned as a specific example, for example. In the following specific examples, Me represents a methyl group.

(Compound represented by Formula (41))

The compound represented by Formula (41) is demonstrated.

(in formula (41),

ring a, ring b and ring c are each independently

A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

It is a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

R ₄₀₁ and R ₄₀₂ are each independently combined with the a ring, b ring or c ring to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle.

_{R 401} and R ₄₀₂ that do not form the substituted or unsubstituted heterocycle are each independently

A substituted or unsubstituted C1-C50 alkyl group;

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 carbon atoms;

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.)

Ring a, ring b and ring c are a ring condensed into a central condensed bicyclic structure of Formula (41) composed of B atoms and two N atoms (a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms).

The "aromatic hydrocarbon ring" of ring a, ring b, and ring c has the same structure as the compound in which a hydrogen atom is introduced into the "aryl group" described above. The "aromatic hydrocarbon ring" of ring a contains three carbon atoms on the central condensed bicyclic structure of Formula (41) as ring forming atoms. The "aromatic hydrocarbon ring" of ring b and ring c contains two carbon atoms on the central condensed bicyclic structure of Formula (41) as ring forming atoms. As a specific example of "a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms", the compound etc. which introduce|transduced the hydrogen atom into the "aryl group" described in specific example group G1 are mentioned.

The "heterocycle" of the a ring, the b ring, and the c ring has the same structure as the compound in which a hydrogen atom is introduced into the "heterocyclic group" described above. The "heterocycle" of the a ring includes three carbon atoms on the central condensed bicyclic structure of the formula (41) as ring forming atoms. The "heterocycle" of ring b and ring c contains two carbon atoms on the central condensed bicyclic structure of Formula (41) as ring forming atoms. As a specific example of "a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms", the compound etc. which introduce|transduced the hydrogen atom into the "heterocyclic group" described in specific example group G2 are mentioned.

R ₄₀₁ and R ₄₀₂ may each independently combine with ring a, ring b or ring c to form a substituted or unsubstituted heterocycle. The heterocycle in this case contains the nitrogen atom on the condensed bicyclic structure at the center of Formula (41). The heterocycle in this case may contain hetero atoms other than a nitrogen atom. When R ₄₀₁ and R ₄₀₂ are bonded to the a ring, the b ring or the c ring, specifically, the atoms constituting the a ring, the b ring or the c ring are bonded to the atoms constituting the _{R 401} and R _{402 .} . For example, R ₄₀₁ may combine with ring a to form a nitrogen-containing heterocycle of bicyclic condensation (or tricyclic condensation or more) in which the ring containing _{R 401 and ring a are condensed.} As a specific example of the said nitrogen-containing heterocyclic ring, the compound etc. corresponding to the heterocyclic group more than bicyclic condensation containing nitrogen among the specific example group G2 are mentioned.

When R ₄₀₁ is bonded to ring b, when R ₄₀₂ is bonded to ring a, and when R ₄₀₂ is bonded to ring c, it is the same as above.

In one embodiment, ring a, ring b, and ring c in Formula (41) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms.

In one embodiment, a ring, b ring, and c ring in Formula (41) are each independently a substituted or unsubstituted benzene ring or a naphthalene ring.

In one embodiment, R ₄₀₁ and R ₄₀₂ in Formula (41) are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring atom number 5 to 50 is a monovalent heterocyclic group, preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, the compound represented by Formula (41) is a compound represented by the following Formula (42).

(in formula (42),

R _401A is combined with one or more selected from the group consisting of R ₄₁₁ and R ₄₂₁ to form a substituted or unsubstituted heterocycle or does not form a substituted or unsubstituted heterocycle. R _402A is combined with one or more selected from the group consisting of R ₄₁₃ and R ₄₁₄ to form a substituted or unsubstituted heterocycle or does not form a substituted or unsubstituted heterocycle.

_{R 401A} and R _402A that do not form the substituted or unsubstituted heterocycle are each independently

A substituted or unsubstituted C1-C50 alkyl group;

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 carbon atoms;

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

One or more pairs of adjacent two or more of R ₄₁₁ to _{R 421} do not combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring.

_{R 411} to _{R 421} which do not form the substituted or unsubstituted heterocycle or the substituted or unsubstituted saturated or unsaturated ring are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

R ₉₀₁ to _{R 907} are as defined in Formula (1) above.)

R _401A and R _402A in the formula (42) are groups corresponding to _{R 401} and R _{402 in the formula (41).}

For example, R _401A and R ₄₁₁ may combine to form a nitrogen-containing heterocycle of bicyclic condensed (or tricyclic condensed or more) in which the ring containing them and the benzene ring corresponding to the a ring are condensed. As a specific example of the said nitrogen-containing heterocyclic ring, the compound etc. corresponding to the heterocyclic group more than bicyclic condensation containing nitrogen among the specific example group G2 are mentioned. The case where R _401A and R ₄₁₂ are bonded, the case where R _402A and R ₄₁₃ are bonded, and the case where R _402A and R ₄₁₄ are bonded are the same as above.

One or more pairs of adjacent two or more of R ₄₁₁ to _{R 421} may combine with each other to form a substituted or unsubstituted saturated or unsaturated ring. For example, R ₁₁ and R ₁₂ may combine to form a structure in which a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring or a benzothiophene ring is condensed with respect to the 6-membered ring to which they are bonded, and the formed condensed ring is It becomes a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring.

_{In one embodiment, R 411} to _{R 421 which} do not contribute to ring formation are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or 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.

_{In one embodiment, R 411} to _{R 421 which} do not contribute to ring formation are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring forming atom 5 It is a monovalent heterocyclic group of -50.

_{In one embodiment, R 411} to _{R 421 which} do not contribute to ring formation are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, R ₄₁₁ to _{R 421} not contributing to ring formation are each independently a hydrogen atom or a substituted or unsubstituted C 1 to C 50 alkyl group, and at least one of _{R 411} to _{R 421 is substituted or unsubstituted} It is a substituted C1-C50 alkyl group.

In one embodiment, the compound represented by the formula (42) is a compound represented by the following formula (43).

(in formula (43),

R ₄₃₁ is _{combined with R 446} to form a substituted or unsubstituted heterocycle or does not form a substituted or unsubstituted heterocycle. R ₄₃₃ is _{combined with R 447} to form a substituted or unsubstituted heterocycle or does not form a substituted or unsubstituted heterocycle. R ₄₃₄ is _{combined with R 451} to form a substituted or unsubstituted heterocycle or does not form a substituted or unsubstituted heterocycle. R ₄₄₁ is _{combined with R 442} to form a substituted or unsubstituted heterocycle or does not form a substituted or unsubstituted heterocycle.

At _{least one pair of adjacent two or more of R 431} to _{R 451} does not form a substituted or unsubstituted saturated or unsaturated ring or a substituted or unsubstituted saturated or unsaturated ring by combining them with each other.

_{R 431} to _{R 451} which do not form the substituted or unsubstituted heterocycle or the substituted or unsubstituted saturated or unsaturated ring are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

R ₉₀₁ to _{R 907} are as defined in Formula (1) above.)

R ₄₃₁ may _{combine with R 446} to form a substituted or unsubstituted heterocycle. For example, R ₄₃₁ and R ₄₄₆ may combine to _{form a tricyclic or more fused nitrogen-containing heterocycle in which a benzene ring to which R 46} is bonded, a ring containing N, and a benzene ring corresponding to the a ring are condensed. As a specific example of the said nitrogen-containing heterocyclic ring, the compound etc. corresponding to the heterocyclic group more than tricyclic condensed containing nitrogen are mentioned among the specific example group G2. The case where R ₄₃₃ and R ₄₄₇ are bonded, the case where R ₄₃₄ and R ₄₅₁ are bonded, and the case where R ₄₄₁ and R ₄₄₂ are bonded are the same as above.

_{In one embodiment, R 431} to _{R 451} that do not contribute to ring formation are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or 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.

_{In one embodiment, R 431} to _{R 451 which} do not contribute to ring formation are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring forming atom 5 It is a monovalent heterocyclic group of -50.

_{In one embodiment, R 431} to _{R 451 which} do not contribute to ring formation are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, R ₄₃₁ to _{R 451} not contributing to ring formation are each independently a hydrogen atom or a substituted or unsubstituted C 1 to C 50 alkyl group, and at least one of _{R 431} to _{R 451 is substituted or unsubstituted} It is a substituted C1-C50 alkyl group.

In one embodiment, the compound represented by the formula (43) is a compound represented by the following formula (43A).

(in formula (43A),

R ₄₆₁ is

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 carbon atoms, or

It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

R ₄₆₂ to _{R 465} are each independently

A substituted or unsubstituted C1-C50 alkyl group;

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 carbon atoms, or

It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.)

In one embodiment, R ₄₆₁ to _{R 465} are each independently a substituted or unsubstituted C 1 to C 50 alkyl group or a substituted or unsubstituted aryl group having 6 to 50 ring C atoms.

In one embodiment, R ₄₆₁ to _{R 465} are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, the compound represented by the formula (43) is a compound represented by the following formula (43B).

(in formula (43B),

R ₄₇₁ and R ₄₇₂ are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 carbon atoms;

-N(R ₉₀₆ )(R ₉₀₇ ), or

It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

R ₄₇₃ to _{R 475} are each independently

A substituted or unsubstituted C1-C50 alkyl group;

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 carbon atoms;

-N(R ₉₀₆ )(R ₉₀₇ ), or

It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

R ₉₀₆ and R ₉₀₇ are as defined in Formula (1) above.)

In one embodiment, the compound represented by the formula (43) is a compound represented by the following formula (43B').

(In the formula (43B'), R ₄₇₂ to _{R 475} are as defined in the formula (43B).)

In one embodiment, at least one of _{R 471} to _{R 475 is}

A substituted or unsubstituted C1-C50 alkyl group;

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 carbon atoms;

-N(R ₉₀₆ )(R ₉₀₇ ), or

It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment,

R ₄₇₂ is

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

-N(R ₉₀₆ )(R ₉₀₇ ), or

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

R ₄₇₁ and R ₄₇₃ to _{R 475} are each independently

A substituted or unsubstituted C1-C50 alkyl group;

-N(R ₉₀₆ )(R ₉₀₇ ), or

It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, the compound represented by the formula (43) is a compound represented by the following formula (43C).

(in formula (43C),

R ₄₈₁ and R ₄₈₂ are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 carbon atoms, or

It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

R ₄₈₃ to _{R 486} are each independently

A substituted or unsubstituted C1-C50 alkyl group;

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 carbon atoms, or

It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.)

In one embodiment, the compound represented by the formula (43) is a compound represented by the following formula (43C').

(In the formula (43C'), R ₄₈₃ to _{R 486} are as defined in the formula (43C).)

In one embodiment, _{each of R 481} to _{R 486} is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, R ₄₈₁ to _{R 486} are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

The compound represented by the formula (41) is prepared by first linking the a ring, the b ring and the c ring with a linking group ( _{a group containing NR 1} and a group containing NR ₂ ) to prepare an intermediate (first reaction), a The final product can be prepared by joining the ring, ring b and ring c with a linking group (a group comprising B) (second reaction). In the first reaction, an amination reaction such as a Buchwald-Hartwig reaction may be applied. In the second reaction, a tandem hetero-Friedel-Crafts reaction or the like can be applied.

Specific examples of the compound represented by the formula (41) are described below, but these are merely examples, and the compound represented by the formula (41) is not limited to the following specific examples. In the following specific examples, Me represents a methyl group and tBu represents a tert-butyl group.

(Compound represented by Formula (51))

The compound represented by Formula (51) is demonstrated.

(in formula (51),

The r ring is a ring represented by Formula (52) or Formula (53) condensed at any position of an adjacent ring.

The q ring and the s ring are each independently a ring represented by the formula (54) condensed at any position in the adjacent ring.

The p-ring and the t-ring are each independently a structure represented by the formula (55) or (56) condensed at any position in the adjacent ring.

When R ₅₀₁ is a plurality is present, bonded to each other is a plurality of R ₅₀₁ adjacent to form a ring, saturated or unsaturated substituted or unsubstituted, or do not form a ring, saturated or unsaturated substituted or unsubstituted.

X ₅₀₁ is an oxygen atom, a sulfur atom, or NR ₅₀₂ .

_{R 501} and R ₅₀₂ that do not form the substituted or unsubstituted saturated or unsaturated ring are

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is 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).

Ar ₅₀₁ and Ar ₅₀₂ are each independently

A substituted or unsubstituted C1-C50 alkyl group;

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 carbon atoms;

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

L ₅₀₁ silver

A substituted or unsubstituted alkylene group having 1 to 50 carbon atoms;

A substituted or unsubstituted alkenylene group having 2 to 50 carbon atoms;

A substituted or unsubstituted alkynylene group having 2 to 50 carbon atoms;

A substituted or unsubstituted cycloalkylene group having 3 to 50 ring carbon atoms;

A substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

It is a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.

m1 is each independently an integer from 0 to 2, m2 is each independently an integer from 0 to 4, m3 is each independently an integer from 0 to 3, and m4 is each independently an integer from 0 to 5. When R ₅₀₁ is a plurality is present, a plurality of R ₅₀₁ may be subjected to a phase may be the same or different.)

In the formula (51), each ring of the p-ring to the t-ring is condensed by sharing two carbon atoms with an adjacent ring. The position and direction to condense are not limited, Condensation is possible in arbitrary positions and directions.

In one embodiment, in Formula (52) or Formula (53) of the r ring, R ₅₀₁ is a hydrogen atom.

In one embodiment, the compound represented by formula (51) is represented by any one of the following formulas (51-1) to (51-6).

(In formulas (51-1) to (51-6), R ₅₀₁ , X ₅₀₁ , Ar ₅₀₁ , Ar ₅₀₂ , L ₅₀₁ , m1 and m3 are as defined in the above formula (51).)

In one embodiment, the compound represented by the formula (51) is represented by any one of the following formulas (51-11) to (51-13).

(In Formulas (51-11) to (51-13), R ₅₀₁ , X ₅₀₁ , Ar ₅₀₁ , Ar ₅₀₂ , L ₅₀₁ , m1 , m3 and m4 are as defined in Formula (51) above.)

In one embodiment, the compound represented by formula (51) is represented by any one of the following formulas (51-21) to (51-25).

(In Formulas (51-21) to (51-25), R ₅₀₁ , X ₅₀₁ , Ar ₅₀₁ , Ar ₅₀₂ , L ₅₀₁ , m1 and m4 are as defined in Formula (51) above.)

In one embodiment, the compound represented by formula (51) is represented by any one of the following formulas (51-31) to (51-33).

(In formulas (51-31) to (51-33), R ₅₀₁ , X ₅₀₁ , Ar ₅₀₁ , Ar ₅₀₂ , L ₅₀₁ , and m2 to m4 are as defined in the above formula (51).)

In one embodiment, Ar ₅₀₁ and Ar ₅₀₂ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, one of Ar ₅₀₁ and Ar ₅₀₂ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the other is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms to be.

As a compound represented by Formula (51), the compound shown below is mentioned as a specific example, for example. In the following specific examples, Me represents a methyl group.

(Compound represented by Formula (61))

The compound represented by Formula (61) is demonstrated.

(in formula (61),

At least one set of R ₆₀₁ and R ₆₀₂ , R ₆₀₂ and R ₆₀₃ , and R ₆₀₃ and R ₆₀₄ is bonded to each other to form a divalent group represented by the following formula (62).

At least one set of R ₆₀₅ and R ₆₀₆ , R ₆₀₆ and R ₆₀₇ , and R ₆₀₇ and R ₆₀₈ is bonded to each other to form a divalent group represented by the following formula (63).

At least one of R ₆₀₁ to _{R 604} that does not form a divalent group represented by the formula (62), and _{at least one of R 611} to _{R 614} is a monovalent group represented by the following formula (64).

At least one of R ₆₀₅ to _{R 608} that does not form a divalent group represented by the formula (63), and _{at least one of R 621} to _{R 624} is a monovalent group represented by the following formula (64).

X ₆₀₁ is an oxygen atom, a sulfur atom, or NR ₆₀₉ ;

_{R 601} to _{R 608 that} does not form a divalent group represented by the formulas (62) and (63), and is not a monovalent group represented by the formula (64), and is not a monovalent group represented by the formula (64) R ₆₁₁ to _{R 614} and R ₆₂₁ to _{R 624} , and R ₆₀₉ are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is 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 formula (64), Ar ₆₀₁ and Ar ₆₀₂ are each independently

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

L _{601 to L 603} are each independently

single bond,

a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms;

A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or

It is a divalent linking group formed by bonding 2 to 4 of them.)

In the formula (61), the position at which the divalent group represented by the formula (62) and the divalent group represented by the formula (63) are formed is not particularly limited, and R ₆₀₁ to _{R 608} may form the group at possible positions. can

In one embodiment, the compound represented by formula (61) is represented by any one of the following formulas (61-1) to (61-6).

(In Formulas (61-1) to (61-6), X ₆₀₁ is as defined in Formula (61) above.

At least two of R ₆₀₁ to _{R 624} are monovalent groups represented by the above formula (64).

_{R 601} to _{R 642, which} are not monovalent groups represented by the formula (64), are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

R ₉₀₁ to _{R 907} are as defined in Formula (1) above.)

In one embodiment, the compound represented by formula (61) is represented by any one of the following formulas (61-7) to (61-18).

(In the formulas (61-7) to (61-18), X ₆₀₁ is as defined in the formula (61). * is a single bond bonded to the monovalent group represented by the formula (64). R ₆₀₁ ~R ₆₂₄ is the same as R ₆₀₁ ~R ₆₂₄ not univalent group represented by the formula (64).)

_{R 601} to _{R 608} , which do not form the divalent group represented by the formulas (62) and (63), and are not the monovalent group represented by the formula (64), and the monovalent group represented by the formula (64) R ₆₁₁ to _{R 614} and R ₆₂₁ to _{R 624 other than} are preferably each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 carbon atoms;

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

The monovalent group represented by the formula (64) is preferably represented by the following formula (65) or (66).

(In formula (65), R ₆₃₁ to _{R 640} are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

R ₉₀₁ to _{R 907} are as defined in Formula (1) above.)

(In Formula (66), Ar ₆₀₁ , L _{601 ,} and L ₆₀₃ are as defined in Formula (64) above. HAr ₆₀₁ has a structure represented by the following Formula (67).

In formula (67), X ₆₀₂ is an oxygen atom or a sulfur atom.

Any one of R ₆₄₁ to _{R 648} is a single bond bonded to _{L 603 .}

_{R 641} to _{R 648} that are not a single bond are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

R ₉₀₁ to _{R 907} are as defined in Formula (1) above.)

As a compound represented by Formula (61), other than the compound described in International Publication No. 2014/104144, the compound shown below is mentioned as a specific example, for example. In the following specific examples, Me represents a methyl group.

(Compound represented by Formula (71))

The compound represented by Formula (71) is demonstrated.

(in formula (71),

A ₇₀₁ ring and A ₇₀₂ ring are each independently

A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

It is a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

At _{least one selected from the group consisting of A 701} ring and A ₇₀₂ ring is bonded to the number of bonds * of the structure represented by the following formula (72).

In formula (72),

A ₇₀₃ rings are each independently

A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

It is a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

X ₇₀₁ is NR ₇₀₃ , C(R ₇₀₄ )(R ₇₀₅ ), Si(R ₇₀₆ )(R ₇₀₇ ), Ge(R ₇₀₈ )(R ₇₀₉ ), O, S or Se.

R ₇₀₁ and R ₇₀₂ combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

_{R 701} and R ₇₀₂ that do not form a substituted or unsubstituted saturated or unsaturated ring, and R ₇₀₃ to _{R 709} are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

R ₉₀₁ to _{R 907} are as defined in Formula (1) above.)

At _{least one selected from the group consisting of A 701} ring and A ₇₀₂ ring is bonded to the number of bonds * in the structure represented by Formula (72). That is, in one embodiment, the _{ring-forming carbon atom of the aromatic hydrocarbon ring of the A 701} ring or the ring-forming atom of the heterocyclic ring is bonded to the number of bonds * in the structure represented by formula (72). Further, in one embodiment, the _{ring-forming carbon atom of the aromatic hydrocarbon ring of the A 702} ring or the ring-forming atom of the heterocyclic ring is bonded to the number of bonds * in the structure represented by formula (72).

In one embodiment, a group represented by the following formula (73) is bonded to either or both of the _{A 701} ring and the A _{702 ring.}

(In formula (73), Ar ₇₀₁ and Ar ₇₀₂ are each independently

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

L _{701 to L 703} are each independently

single bond,

a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms;

A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or

It is a divalent linking group formed by bonding 2 to 4 of them.)

In one embodiment, in addition to the _{A 701 ring, the ring-forming carbon atom of the aromatic hydrocarbon ring of the A 702} ring, or the ring-forming atom of the heterocyclic ring is bonded to the number of bonds * in the structure represented by formula (72). In this case, the structures represented by Formula (72) may be the same or different.

In one embodiment, R ₇₀₁ and R ₇₀₂ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, R ₇₀₁ and R ₇₀₂ combine with each other to form a fluorene structure.

In one embodiment, Ring A ₇₀₁ and Ring A ₇₀₂ are a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, such as a substituted or unsubstituted benzene ring.

In one embodiment, Ring A ₇₀₃ is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, such as a substituted or unsubstituted benzene ring.

In one embodiment, X ₇₀₁ is O or S.

As a compound represented by Formula (71), the compound shown below is mentioned as a specific example, for example. In the following specific examples, Me represents a methyl group.

(Compound represented by Formula (81))

The compound represented by Formula (81) is demonstrated.

(in formula (81),

The A ₈₀₁ ring is a ring represented by the formula (82) condensed at any position of an adjacent ring.

A ₈₀₂ ring is a ring represented by formula (83) condensed at any position of an adjacent ring. Two bonding numbers* bond at any position on the _{A 803 ring.}

X ₈₀₁ and X ₈₀₂ are each independently C(R ₈₀₃ )(R ₈₀₄ ), Si(R ₈₀₅ )(R ₈₀₆ ), an oxygen atom, or a sulfur atom.

A ₈₀₃ ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

Ar ₈₀₁ is 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 ₈₀₁ to _{R 806} are each independently

hydrogen atom,

A substituted or unsubstituted C1-C50 alkyl group;

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 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

It is 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).

m801 and m802 are each independently an integer of 0-2. When these are 2, a plurality of R ₈₀₁ or R ₈₀₂ may be the same as or different from each other.

a801 is an integer from 0 to 2. When a801 is 0 or 1, the structures in parentheses indicated by "3-a801" may be the same as or different from each other. When a801 is 2, Ar ₈₀₁ may be the same as or different from each other.)

In one embodiment, Ar ₈₀₁ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, Ring A ₈₀₃ is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, such as a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted It is an anthracene ring.

In one embodiment, R ₈₀₃ and R ₈₀₄ are each independently a substituted or unsubstituted C1-C50 alkyl group.

In one embodiment, a801 is 1.

As a compound represented by Formula (81), the compound shown below is mentioned as a specific example, for example.

As for content in the light emitting layer of the compound (host material) represented by Formula (1), 80 mass % or more and 99 mass % or less are preferable with respect to the whole light emitting layer. In addition, in the light emitting layer of at least one compound (dopant material) selected from the group consisting of formulas (11), (21), (31), (41), (51), (61), (71) and (81) As for content, 1 mass % or more and 20 mass % or less are preferable with respect to the whole light emitting layer.

Hereinafter, members that can be used in the organic EL device according to one embodiment of the present invention, materials other than the above compounds constituting each layer, and the like will be described.

(Board)

The substrate is used as a support for the light emitting device. As the substrate, for example, glass, quartz, plastic or the like can be used. Moreover, you may use a flexible board|substrate. The flexible substrate refers to a substrate that can be bent (flexible), for example, a plastic substrate including polycarbonate and polyvinyl chloride.

(anode)

For the anode formed on the substrate, it is preferable to use a metal having a large work function (specifically, 4.0 eV or more), an alloy, an electrically conductive compound, a mixture thereof, or the like. Specifically, for example, indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, and indium oxide containing zinc oxide, yes A pin etc. are mentioned. In addition, gold (Au), platinum (Pt), or a nitride of a metal material (eg, titanium nitride) may be mentioned.

(hole injection layer)

The hole injection layer is a layer including a material having high hole injection property. Examples of the material having high hole injection property include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, aromatic amine compound, or A high molecular compound (oligomer, dendrimer, polymer, etc.) etc. can be used.

(hole transport layer)

The hole transport layer is a layer containing a material having high hole transport properties. An aromatic amine compound, a carbazole derivative, an anthracene derivative, etc. can be used for a hole transport layer. A high molecular compound such as poly(N-vinylcarbazole) (abbreviation: PVK) or poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. However, materials other than these may be used as long as they have a higher hole transport property than electrons. In addition, the layer containing the substance with high hole-transport property is not only a single|mono layer, but the layer containing the said substance may be laminated|stacked in two or more layers.

(Guest material of the light emitting layer)

The light emitting layer is a layer containing a substance having high light emitting property, and various materials can be used. For example, a fluorescent compound emitting fluorescence or a phosphorescent compound emitting phosphorescence can be used as the substance having high luminescence. A fluorescent compound is a compound capable of emitting light from a singlet excited state, and a phosphorescent compound is a compound capable of emitting light from a triplet excited state.

A pyrene derivative, a styrylamine derivative, a chrysene derivative, a fluoranthene derivative, a fluorene derivative, a diamine derivative, a triarylamine derivative, etc. can be used as a blue fluorescent-emitting material which can be used for a light emitting layer. As a green fluorescent light emitting material that can be used for the light emitting layer, an aromatic amine derivative or the like can be used. As a red fluorescent material that can be used for the light emitting layer, a tetracene derivative, a diamine derivative, or the like can be used.

Metal complexes, such as an iridium complex, an osmium complex, and a platinum complex, are used as a blue phosphorescence-emitting material which can be used for a light emitting layer. As a green phosphorescent material that can be used for the light emitting layer, an iridium complex or the like is used. Metal complexes, such as an iridium complex, a platinum complex, a terbium complex, and a europium complex, are used as a red phosphorescence-emitting material which can be used for a light emitting layer.

(Host material of light emitting layer)

The light emitting layer may have a configuration in which the above-described high luminescent material (guest material) is dispersed in another material (host material). Various materials can be used as a material for dispersing a material with high luminescence, and it is preferable to use a material having a higher lowest empty orbital level (LUMO level) and a lower highest occupied orbital level (HOMO level) than a high luminescent material. Do.

As a substance (host material) for dispersing a substance with high luminescence, 1) a metal complex such as an aluminum complex, a beryllium complex or a zinc complex, 2) a heterocyclic ring such as an oxadiazole derivative, a benzimidazole derivative or a phenanthroline derivative compound, 3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives or chrysene derivatives, and 3) aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives.

(electron transport layer)

The electron transport layer is a layer containing a material having high electron transport properties. In the electron transport layer, 1) metal complexes such as aluminum complex, beryllium complex, zinc complex, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, 3) polymers compounds may be used.

(electron injection layer)

The electron injection layer is a layer containing a material having high electron injection property. Metals such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), and 8-hydroxyquinolinolato-lithium (Liq) in the electron injection layer A complex compound, _{an alkali metal such as lithium oxide (LiO x} ), an alkaline earth metal, or a compound thereof can be used.

(cathode)

For the negative electrode, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a small work function (specifically, 3.8 eV or less). Specific examples of such anode material include elements belonging to Group 1 or Group 2 of the Periodic Table of the Elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg), calcium (Ca), strontium ( and alkaline earth metals such as Sr) and alloys containing them (eg, MgAg, AlLi), europium (Eu), and rare earth metals such as ytterbium (Yb), and alloys containing them.

In the organic EL device according to one aspect of the present invention, the method for forming each layer is not particularly limited. A formation method by a conventionally well-known vacuum deposition method, a spin coating method, etc. can be used. Each layer such as the light emitting layer is formed by a known method using a vacuum deposition method, a molecular beam deposition method (MBE method) or a coating method such as a dipping method of a solution dissolved in a solvent, a spin coating method, a casting method, a bar coating method, and a roll coating method can do.

In the organic EL device according to an aspect of the present invention, the film thickness of each layer is not particularly limited, but in general, in order to suppress defects such as pinholes, reduce the applied voltage, and improve luminous efficiency, it is usually A range of several nm to 1 m is preferable.

[Electronics]

An electronic device according to an aspect of the present invention includes the organic EL device according to an aspect of the present invention.

Specific examples of the electronic device include display parts such as an organic EL panel module, a display device such as a television, a mobile phone, or a personal computer, and a light emitting device such as lighting or a vehicle lighting fixture.

Example

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

Synthesis Example 1 [Synthesis of Compound BH-1]

(Synthesis of Intermediate 1)

Toluene 75 ml, dimethoxyethane 75 ml in 13.3 g (50.0 mmol) of 9-bromoanthracene-d9, 6.4 g (52.5 mmol) of phenylboronic acid, _{1.2 g (1.00 mmol) of Pd[PPh 3} ] _{4 under argon atmosphere} , 2M Na ₂ CO ₃ aqueous solution of 75 ml (150.0 mmol) was added, and the mixture was stirred under reflux for 10 hours.

After completion of the reaction, the mixture was cooled to room temperature, and the sample was transferred to a separation funnel and extracted with dichloromethane. The organic phase _{was dried over MgSO 4} , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 10.9 g of a white solid. FD-MS analysis was performed on the obtained compound, and it was identified as the following intermediate 1 (yield 83%).

(Synthesis of Intermediate 2)

A solution of 5.3 g (20.0 mmol) of Intermediate 1 in 120 ml of dichloromethane was added dropwise to a solution of 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane at room temperature, followed by stirring for 1 hour.

After completion of the reaction, the sample was transferred to a separation funnel and washed with a _{2M Na 2} S ₂ O _{3 aqueous solution.} Further, the organic phase was washed with 10% Na ₂ CO ₃ , and then washed with water, and the separated organic phase _{was dried over MgSO 4} , filtered and concentrated.

The concentrated residue was dispersed in methanol (100 ml) to collect precipitated crystals to obtain 6.5 g of a white solid. FD-MS analysis was performed on the obtained compound, and it was identified as the following intermediate 2 (yield 95%).

(Synthesis of compound BH-1)

Under argon atmosphere, intermediate 2 1.7 g (5.0 mmol), benzo [b] naphtho [2,3-d] furan-2-boronic acid 1.4 g (5.3 mmol), Pd [PPh ₃ ] ₄ 0.1 g (0.1 mmol) ), toluene 7.5 ml, dimethoxyethane 7.5 ml, 2M Na ₂ CO ₃ aqueous solution 7.5 ml (15.0 mmol) were added, and the mixture was heated and stirred under reflux for 10 hours.

After completion of the reaction, the mixture was cooled to room temperature, and the sample was transferred to a separation funnel and extracted with dichloromethane. The organic phase _{was dried over MgSO 4} , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 1.7 g of a white solid. FD-MS analysis was performed on the obtained compound, and it was identified as the following compound BH-1 (yield 70%).

Synthesis Example 2 [Synthesis of Compound BH-2]

(Synthesis of Intermediate 3)

Toluene 75 ml, dimethoxyethane in 13.3 g (50.0 mmol) of 9-bromoanthracene-d9, 9.0 g (52.5 mmol) of 1-naphthaleneboronic acid, 1.2 g (1.00 mmol) of _{Pd[PPh 3} ] _{4 under an argon atmosphere} 75 ml, 2M Na ₂ CO ₃ aqueous solution 75 ml (150.0 mmol) was added, and the mixture was stirred under reflux for 10 hours.

After completion of the reaction, it was cooled to room temperature, and the sample was transferred to a separation funnel and extracted with dichloromethane. The organic phase _{was dried over MgSO 4} , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 13.3 g of a white solid. FD-MS analysis was performed on the obtained compound, and it was identified as the following intermediate 3 (yield 85%).

(Synthesis of Intermediate 4)

A solution of 6.3 g (20.0 mmol) of Intermediate 3 in 120 ml of dichloromethane was added dropwise to a solution of 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane at room temperature, followed by stirring for 1 hour.

After completion of the reaction, the sample was transferred to a separation funnel and washed with a _{2M Na 2} S ₂ O _{3 aqueous solution.} Further, the organic phase was washed with 10% Na ₂ CO ₃ , then washed 3 times with water. The organic phase _{was dried over MgSO 4} , filtered and concentrated.

The concentrated residue was dispersed in methanol (100 mL) to collect precipitated crystals to obtain 7.5 g of a white solid. FD-MS analysis was performed on the obtained compound, and it was identified as the following intermediate 4 (yield 96%).

(Synthesis of compound BH-2)

Under argon atmosphere, intermediate 4 2.0 g (5.0 mmol), benzo [b] naphtho [2,3-d] furan-2-boronic acid 1.4 g (5.3 mmol), Pd [PPh ₃ ] ₄ 0.1 g (0.1 mmol) ), toluene 7.5 ml, dimethoxyethane 7.5 ml, 2M Na ₂ CO ₃ aqueous solution 7.5 ml (15.0 mmol) were added, and the mixture was heated and stirred under reflux for 10 hours.

After completion of the reaction, the mixture was cooled to room temperature, and the sample was transferred to a separation funnel and extracted with dichloromethane. The organic phase _{was dried over MgSO 4} , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 1.9 g of a white solid. FD-MS analysis was performed on the obtained compound, and it was identified as the following compound BH-2 (yield 73%).

Synthesis Example 3 [Synthesis of Compound BH-3]

(Synthesis of Intermediate 5)

Toluene 75 in 13.3 g (50.0 mmol) of 9-bromoanthracene d9, 13.0 g (52.5 mmol) of 4-(1-naphthyl)phenylboronic acid, 1.2 g (1.00 mmol) of _{Pd[PPh 3} ] _{4 under argon atmosphere} ml, dimethoxyethane 75 ml, 2M Na ₂ CO ₃ aqueous solution 75 ml (150.0 mmol) were added, and the mixture was stirred under reflux for 10 hours.

After completion of the reaction, the mixture was cooled to room temperature, and the sample was transferred to a separation funnel and extracted with dichloromethane. The organic phase _{was dried over MgSO 4} , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 15.6 g of a white solid. FD-MS analysis was performed on the obtained compound, and it was identified as the following intermediate 5 (yield 80%).

(Synthesis of Intermediate 6)

A solution of 7.8 g (20.0 mmol) of Intermediate 5 in 120 ml of dichloromethane was added dropwise to a solution of 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane at room temperature, followed by stirring for 1 hour.

After completion of the reaction, the sample was transferred to a separation funnel and washed with a _{2M Na 2} S ₂ O _{3 aqueous solution.} Further, the organic phase was washed with 10% Na ₂ CO ₃ , then washed 3 times with water. The organic phase _{was dried over MgSO 4} , filtered and concentrated.

The concentrated residue was dispersed in methanol (100 ml) to collect precipitated crystals to obtain 8.6 g of a white solid. FD-MS analysis was performed on the obtained compound, and it was identified as the following intermediate 6 (yield 92%).

(Synthesis of compound BH-3)

Under argon atmosphere, intermediate 6 2.3 g (5.0 mmol), benzo [b] naphtho [2,3-d] furan-2-boronic acid 1.4 g (5.3 mmol), Pd [PPh ₃ ] ₄ 0.1 g (0.1 mmol) ), toluene 7.5 ml, dimethoxyethane 7.5 ml, 2M Na ₂ CO ₃ aqueous solution 7.5 ml (15.0 mmol) were added, and the mixture was heated and stirred under reflux for 10 hours.

After completion of the reaction, the mixture was cooled to room temperature, and the sample was transferred to a separation funnel and extracted with dichloromethane. The organic phase _{was dried over MgSO 4} , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 2.1 g of a white solid. FD-MS analysis was performed on the obtained compound, and it was identified as the following compound BH-3 (yield 68%).

Synthesis Example 4 [Synthesis of Compound BH-4]

In Synthesis Example 1, 1.4 g of benzo[b]naphtho[1,2-d]furan-10-boronic acid instead of benzo[b]naphtho[2,3-d]furan-2-boronic acid ( 5.3 mmol) was used, and the reaction was conducted in the same manner to obtain 1.7 g of white crystals. FD-MS analysis was performed on the obtained compound, and it was identified as the following compound BH-4 (yield 71%).

Synthesis Example 5 [Synthesis of Compound BH-5]

In Synthesis Example 1, 1.4 g of benzo[b]naphtho[2,1-d]furan-8-boronic acid instead of benzo[b]naphtho[2,3-d]furan-2-boronic acid ( 5.3 mmol) was used, and the reaction was conducted in the same manner to obtain 1.6 g of white crystals. FD-MS analysis was performed on the obtained compound, and it was identified as the following compound BH-5 (yield 65%).

Synthesis Example 6 [Synthesis of Compound BH-6]

In Synthesis Example 1, 1.4 g of benzo[b]naphtho[2,3-d]furan-1-boronic acid instead of benzo[b]naphtho[2,3-d]furan-2-boronic acid ( 5.3 mmol) was used, and the same reaction was conducted to obtain 1.4 g of white crystals. FD-MS analysis was performed on the obtained compound, and it was identified as the following compound BH-6 (yield 57%).

Synthesis Example 7 [Synthesis of Compound BH-7]

(Synthesis of Intermediate 7)

Toluene 75 ml, dimethoxyethane in 13.3 g (50.0 mmol) of 9-bromoanthracene d9, 10.4 g (52.5 mmol) of 3-biphenylboronic acid, 1.2 g (1.00 mmol) of _{Pd[PPh 3} ] _{4 under argon atmosphere} 75 ml, 2M Na ₂ CO ₃ aqueous solution 75 ml (150.0 mmol) was added, and the mixture was stirred under reflux for 10 hours.

After completion of the reaction, the mixture was cooled to room temperature, and the sample was transferred to a separation funnel and extracted with dichloromethane. The organic phase _{was dried over MgSO 4} , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 13.6 g of a white solid. FD-MS analysis was performed on the obtained compound, and it was identified as the following intermediate 7 (yield 80%).

(Synthesis of Intermediate 8)

A solution of 6.8 g (20.0 mmol) of Intermediate 7 in 120 ml of dichloromethane was added dropwise to a solution of 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane at room temperature, followed by stirring for 1 hour.

After completion of the reaction, the sample was transferred to a separation funnel and washed with a _{2M Na 2} S ₂ O _{3 aqueous solution.} Further, the organic phase was washed with 10% Na ₂ CO ₃ , then washed 3 times with water. The organic phase _{was dried over MgSO 4} , filtered and concentrated.

The concentrated residue was dispersed in methanol (100 mL) to collect precipitated crystals to obtain 8.0 g of a white solid. FD-MS analysis was performed on the obtained compound, and it was identified as the following intermediate 8 (yield 96%).

(Synthesis of compound BH-7)

Under argon atmosphere, intermediate 8 2.1 g (5.0 mmol), benzo [b] naphtho [2,3-d] furan-1-boronic acid 1.4 g (5.3 mmol), Pd [PPh ₃ ] ₄ 0.1 g (0.1 mmol) ), toluene 7.5 ml, dimethoxyethane 7.5 ml, 2M Na ₂ CO ₃ aqueous solution 7.5 ml (15.0 mmol) were added, and the mixture was heated and stirred under reflux for 10 hours.

After completion of the reaction, the mixture was cooled to room temperature, and the sample was transferred to a separation funnel and extracted with dichloromethane. The organic phase _{was dried over MgSO 4} , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 1.7 g of a white solid. FD-MS analysis was performed on the obtained compound, and it was identified as the following compound BH-7 (yield 60%).

Synthesis Example 8 [Synthesis of Compound BH-8]

In Synthesis Example 1, 1.4 g of benzo[b]naphtho[2,1-d]furan-7-boronic acid instead of benzo[b]naphtho[2,3-d]furan-2-boronic acid ( 5.3 mmol) was used, and the reaction was conducted in the same manner to obtain 1.6 g of white crystals. FD-MS analysis was performed on the obtained compound, and it was identified as the following compound BH-8 (yield 65%).

Synthesis Example 9 [Synthesis of Compound BH-9]

(Synthesis of Intermediate 9)

Toluene 75 ml, dimethoxyethane in 13.3 g (50.0 mmol) of 9-bromoanthracene d9, 10.4 g (52.5 mmol) of 4-biphenylboronic acid, 1.2 g (1.00 mmol) of _{Pd[PPh 3} ] _{4 under argon atmosphere} 75 ml, 2M Na ₂ CO ₃ aqueous solution 75 ml (150.0 mmol) was added, and the mixture was stirred under reflux for 10 hours.

After completion of the reaction, it was cooled to room temperature, and the sample was transferred to a separation funnel and extracted with dichloromethane. The organic phase _{was dried over MgSO 4} , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 14.1 g of a white solid. FD-MS analysis was performed on the obtained compound, and it was identified as the following intermediate 9 (yield 83%).

(Synthesis of Intermediate 10)

A solution of 6.8 g (20.0 mmol) of Intermediate 9 in 120 ml of dichloromethane was added dropwise to a solution of 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane at room temperature, followed by stirring for 1 hour.

After completion of the reaction, the sample was transferred to a separation funnel and washed with a _{2M Na 2} S ₂ O _{3 aqueous solution.} Further, the organic phase was washed with 10% Na ₂ CO ₃ , then washed 3 times with water. The organic phase _{was dried over MgSO 4} , filtered and concentrated.

The concentrated residue was dispersed in methanol (100 mL) to collect precipitated crystals to obtain 8.0 g of a white solid. FD-MS analysis was performed on the obtained compound, and it was identified as the following intermediate 10 (yield 96%).

(Synthesis of compound BH-9)

Under argon atmosphere, intermediate 10 2.1 g (5.0 mmol), benzo [b] naphtho [2,3-d] furan-1-boronic acid 1.4 g (5.3 mmol), Pd [PPh ₃ ] ₄ 0.1 g (0.1 mmol) ), toluene 7.5 ml, dimethoxyethane 7.5 ml, 2M Na ₂ CO ₃ aqueous solution 7.5 ml (15.0 mmol) were added, and the mixture was heated and stirred under reflux for 10 hours.

After completion of the reaction, the mixture was cooled to room temperature, and the sample was transferred to a separation funnel and extracted with dichloromethane. The organic phase _{was dried over MgSO 4} , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 1.4 g of a white solid. FD-MS analysis was performed on the obtained compound, and it was identified as the following compound BH-9 (yield 51%).

Synthesis Example 10 [Synthesis of Compound BH-10]

In Synthesis Example 7, 1.4 g of benzo[b]naphtho[2,1-d]furan-7-boronic acid instead of benzo[b]naphtho[2,3-d]furan-1-boronic acid ( 5.3 mmol) was used, and the reaction was repeated to obtain 1.4 g of white crystals. FD-MS analysis was performed on the obtained compound, and it was identified as the following compound BH-10 (yield 52%).

Synthesis Example 11 [Synthesis of Compound BH-11]

In Synthesis Example 1, 3-(benzo[b]naphtho[2,3-d]furan-1-yl)phenyl instead of benzo[b]naphtho[2,3-d]furan-2-boronic acid The same reaction was carried out except that 1.8 g (5.3 mmol) of boronic acid was used to obtain 1.5 g of white crystals. FD-MS analysis was performed on the obtained compound, and it was identified as the following compound BH-11 (yield 53%).

Synthesis Example 12 [Synthesis of Compound BH-12]

(Synthesis of Intermediate 11)

Toluene 75 ml, dimethoxyethane in 13.3 g (50.0 mmol) of 9-bromoanthracene d9, 10.4 g (52.5 mmol) of 2-biphenylboronic acid, 1.2 g (1.00 mmol) of _{Pd[PPh 3} ] _{4 under argon atmosphere} 75 ml, 2M Na ₂ CO ₃ aqueous solution 75 ml (150.0 mmol) was added, and the mixture was stirred under reflux for 10 hours.

After completion of the reaction, the mixture was cooled to room temperature, and the sample was transferred to a separation funnel and extracted with dichloromethane. The organic phase _{was dried over MgSO 4} , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 10.9 g of a white solid. FD-MS analysis was performed on the obtained compound, and it was identified as the following intermediate 11 (yield 64%).

(Synthesis of Intermediate 12)

A solution of 6.8 g (20.0 mmol) of Intermediate 11 in 120 ml of dichloromethane was added dropwise to a solution of 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane at room temperature, followed by stirring for 1 hour.

After completion of the reaction, the sample was transferred to a separation funnel and washed with a _{2M Na 2} S ₂ O _{3 aqueous solution.} Further, the organic phase was washed with 10% Na ₂ CO ₃ , then washed 3 times with water. The organic phase _{was dried over MgSO 4} , filtered and concentrated.

The concentrated residue was dispersed in methanol (100 mL) to collect precipitated crystals to obtain 8.0 g of a white solid. FD-MS analysis was performed on the obtained compound, and it was identified as the following intermediate 12 (yield 96%).

(Synthesis of compound BH-12)

Under argon atmosphere, intermediate 12 2.1 g (5.0 mmol), benzo [b] naphtho [2,3-d] furan-2-boronic acid 1.4 g (5.3 mmol), Pd [PPh ₃ ] ₄ 0.1 g (0.1 mmol) ), toluene 7.5 ml, dimethoxyethane 7.5 ml, 2M Na ₂ CO ₃ aqueous solution 7.5 ml (15.0 mmol) were added, and the mixture was heated and stirred under reflux for 10 hours.

After completion of the reaction, the mixture was cooled to room temperature, and the sample was transferred to a separation funnel and extracted with dichloromethane. The organic phase _{was dried over MgSO 4} , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 1.7 g of a white solid. FD-MS analysis was performed on the obtained compound, and it was identified as the following compound BH-12 (yield 60%).

Synthesis Example 13 [Synthesis of Compound BH-13]

In Synthesis Example 1, 1.4 g of benzo[b]naphtho[2,1-d]furan-6-boronic acid instead of benzo[b]naphtho[2,3-d]furan-2-boronic acid ( 5.3 mmol) was used, and the reaction was conducted in the same manner to obtain 1.2 g of white crystals. FD-MS analysis was performed on the obtained compound, and it was identified as the following compound BH-13 (yield 50%).

Synthesis Example 14 [Synthesis of Compound BH-14]

In Synthesis Example 1, 4-(benzo [b] naphtho [2,3-d] furan-1-yl) phenyl instead of benzo [b] naphtho [2,3-d] furan-2-boronic acid The same reaction was carried out except that 1.8 g (5.3 mmol) of boronic acid was used to obtain 1.5 g of white crystals. FD-MS analysis was performed on the obtained compound, and it was identified as the following compound BH-14 (yield 55%).

Synthesis Example 15 [Synthesis of Compound BH-15]

(Synthesis of Intermediate 13)

Under argon atmosphere, 9-bromoanthracene d9 1.33 g (5.00 mmol), phenyl-d5-boronic acid 0.67 g (5.25 mmol), Pd[PPh ₃ ] ₄ 0.12 g (0.10 mmol) in toluene 7.5 ml, dimethoxyethane 7.5 ml, _{7.5 ml (15.0 mmol) of a 2M Na 2} CO ₃ aqueous solution was added, and the mixture was stirred under reflux for 10 hours.

After completion of the reaction, the mixture was cooled to room temperature, and the sample was transferred to a separation funnel and extracted with dichloromethane. The organic phase _{was dried over MgSO 4} , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 1.07 g of a white solid. FD-MS analysis was performed on the obtained compound, and it was identified as the following intermediate 13 (yield 80%).

(Synthesis of Intermediate 14)

A solution of 1.07 g (4.0 mmol) of Intermediate 13 in 25 ml of dichloromethane was added dropwise to a solution of 0.64 g (4.0 mmol) of bromine in 3 ml of dichloromethane at room temperature, followed by stirring for 1 hour.

After completion of the reaction, the sample was transferred to a separation funnel and washed with a _{2M Na 2} S ₂ O _{3 aqueous solution.} Further, the organic phase was washed with 10% Na ₂ CO ₃ , then with water, and the separated organic phase _{was dried over MgSO 4} , filtered and concentrated.

The concentrated residue was dispersed in methanol (100 ml) to collect precipitated crystals to obtain 1.3 g of a white solid. FD-MS analysis was performed on the obtained compound, and it was identified as the following intermediate 14 (yield 95%).

(Synthesis of compound BH-15)

Under argon atmosphere, 0.87 g (2.5 mmol) of Intermediate 14, 0.69 g (2.65 mmol) of benzo[b]naphtho[2,3-d]furan-2-boronic acid, 0.06 g (0.05 mmol _{) of Pd[PPh 3} ] ₄ ), 5 ml of toluene, 5 ml of dimethoxyethane, and _{5 ml (10.0 mmol) of a 2M Na 2} CO ₃ aqueous solution were added, followed by heating and stirring under reflux for 10 hours.

After completion of the reaction, the mixture was cooled to room temperature, and the sample was transferred to a separation funnel and extracted with dichloromethane. The organic phase _{was dried over MgSO 4} , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 0.87 g of a white solid. FD-MS analysis was performed on the obtained compound, and it was identified as the following compound BH-15 (yield 72%).

Synthesis Example 16 [Synthesis of Compound BH-16]

In Synthesis Example 2, 1.4 g of benzo[b]naphtho[1,2-d]furan-10-boronic acid instead of benzo[b]naphtho[2,3-d]furan-2-boronic acid ( 5.3 mmol) was used, and the reaction was carried out in the same manner to obtain 1.5 g of white crystals. FD-MS analysis was performed on the obtained compound, and it was identified as the following compound BH-16 (yield 56%).

Example 1

(Production of organic EL device)

A glass substrate (manufactured by Geomatic Co., Ltd.) provided with an ITO transparent electrode (anode) having a thickness of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. . The film thickness of ITO was 130 nm.

A glass substrate equipped with a transparent electrode after cleaning is mounted on a substrate holder of a vacuum vapor deposition apparatus, first, a compound HI is deposited on the surface on which the transparent electrode is formed so as to cover the transparent electrode, and HI having a film thickness of 5 nm A film was formed. This HI film functions as a hole injection layer.

Following the formation of the HI film, a compound HT-1 was vapor-deposited, and an HT-1 film having a thickness of 80 nm was formed on the HI film. This HT-1 film functions as a hole transport layer (first hole transport layer).

Following the formation of the HT-1 film, a compound HT-2 was vapor-deposited, and an HT-2 film having a thickness of 10 nm was formed on the HT-1 film. This HT-2 film functions as an electron blocking layer (second hole transport layer).

Compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited on the HT-2 film so that the ratio of compound BD-1 was 4 mass %, and BH-1:BD- with a film thickness of 25 nm Film 1 was formed. This BH-1:BD-1 film functions as a light emitting layer.

Compound ET-1 was vapor-deposited on this light emitting layer, and the ET-1 film with a film thickness of 10 nm was formed into a film. This ET-1 film functions as a hole barrier layer.

Compound ET-2 was deposited on the ET-1 film to form an ET-2 film with a thickness of 15 nm. This ET-2 film functions as an electron transport layer. LiF was vapor-deposited on this 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 with a film thickness of 80 nm, and an organic EL element was produced.

The layer structure of the obtained organic electroluminescent element is as follows.

ITO(130)/HI(5)/HT-1(80)/HT-2(10)/BH-1:BD-1(25:4% by mass)/ET-1(10)/ET-2( 15)/LiF(1)/Al(80)

The number in parentheses indicates the film thickness (unit: nm).

The materials used in Example 1 and the Examples and Comparative Examples mentioned later are shown below.

(Evaluation of organic EL device)

A voltage was applied to the obtained organic EL device so that the current density became 50 mA/cm 2 , and the time (LT95 (unit: time)) until the luminance became 95% with respect to the initial luminance was measured. A result is shown in Table 1.

In addition, the CIE1931 chromaticity coordinates (CIEx, CIEy) when a voltage was applied to the obtained organic EL element so that the current density was 10 mA/cm 2 was measured using a spectral emission luminance meter CS-1000 (manufactured by Konica Minolta Corporation). Thus, a spectral radiation luminance spectrum was obtained and measured. A result is shown in Table 1.

Comparative Example 1-1, Comparative Example 1-2

An organic EL device was manufactured and evaluated in the same manner as in Example 1, except that the compounds shown in the following table were used as the host material for the light emitting layer. A result is shown in Table 1.

Example 2, Comparative Example 2

An organic EL device was manufactured and evaluated in the same manner as in Example 1, except that the compounds shown in the following table were used as the host material for the light emitting layer. A result is shown in Table 2.

Example 3, Comparative Examples 3-1, 3-2

An organic EL device was manufactured and evaluated in the same manner as in Example 1, except that the compounds shown in the following table were used as the host material for the light emitting layer. A result is shown in Table 3.

Example 4, Comparative Example 4-1, Comparative Example 4-2

An organic EL device was manufactured and evaluated in the same manner as in Example 1, except that the compounds shown in the following table were used as the host material for the light emitting layer. A result is shown in Table 4.

Example 5, Comparative Example 5

An organic EL device was manufactured and evaluated in the same manner as in Example 1, except that the compounds shown in the following table were used as the host material for the light emitting layer. A result is shown in Table 5.

Example 6, Comparative Example 6

An organic EL device was manufactured and evaluated in the same manner as in Example 1, except that the compounds shown in the following table were used as the host material for the light emitting layer. A result is shown in Table 6.

Example 11, Comparative Example 11

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 7.

Example 12, Comparative Example 12

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 8.

Example 13, Comparative Example 13

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 9.

Example 14, Comparative Example 14

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 10.

Example 15, Comparative Example 15

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 11.

Example 16, Comparative Example 16

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 12.

Example 17, Comparative Example 17

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 13.

Example 18, Comparative Example 18

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 14.

Example 21, Comparative Example 21

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 15.

Example 22, Comparative Example 22

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 16.

Example 23, Comparative Example 23

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 17.

Example 24, Comparative Example 24

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 18.

Example 25, Comparative Example 25

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 19.

Example 26, Comparative Example 26

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 20.

Example 27, Comparative Example 27

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 21.

Example 28, Comparative Example 28

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 22.

Example 31, Comparative Example 31

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 23.

Example 32, Comparative Example 32

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 24.

Example 33, Comparative Example 33

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 25.

Example 34, Comparative Example 34

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 26.

Example 35, Comparative Example 35

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 27.

Example 36, Comparative Example 36

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 28.

Example 37, Comparative Example 37

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 29.

Example 38, Comparative Example 38

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 30.

Example 41, Comparative Example 41

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 31.

Example 42, Comparative Example 42

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 32.

Example 43, Comparative Example 43

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 33.

Example 44, Comparative Example 44

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 34.

Example 45, Comparative Example 45

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 35.

Example 46, Comparative Example 46

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 36.

Example 47, Comparative Example 47

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 37.

Example 48, Comparative Example 48

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 38.

Example 51, Comparative Example 51

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 39.

Example 52, Comparative Example 52

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 40.

Example 53, Comparative Example 53

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 41.

Example 54, Comparative Example 54

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 42.

Example 55, Comparative Example 55

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 43.

Example 56, Comparative Example 56

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 44.

Example 57, Comparative Example 57

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 45.

Example 58, Comparative Example 58

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 46.

Example 61, Comparative Example 61

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 47.

Example 62, Comparative Example 62

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 48.

Example 63, Comparative Example 63

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 49.

Example 64, Comparative Example 64

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 50.

Example 65, Comparative Example 65

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 51.

Example 66, Comparative Example 66

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 52.

Example 67, Comparative Example 67

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 53.

Example 68, Comparative Example 68

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 54.

Example 69, Comparative Example 69

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 55.

Example 70, Comparative Example 70

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 56.

Example 71, Comparative Example 71

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 57.

Example 72, Comparative Example 72

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 58.

Example 73, Comparative Example 73

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 59.

Example 74, Comparative Example 74

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 60.

Example 75, Comparative Example 75

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 61.

Example 76, Comparative Example 76

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 62.

Example 77

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 63.

Example 78, Comparative Example 78

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 64.

Comparative Example 79

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 65.

Example 80, Comparative Example 80

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 66.

Example 81, Comparative Example 81

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 67.

Example 82, Comparative Example 82

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 68.

Example 83, Comparative Example 83

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 69.

Example 84, Comparative Example 84

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 70.

Example 85, Comparative Example 85

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 71.

Example 86

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 72.

Example 87, Comparative Example 87

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 73.

Comparative Example 88

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 74.

Example 89, Comparative Example 89

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 75.

Example 90, Comparative Example 90

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 76.

Example 91, Comparative Example 91

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 77.

Example 92, Comparative Example 92

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 78.

Example 93, Comparative Example 93

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 79.

Example 94, Comparative Example 94

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 80.

Example 95

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 81.

Example 96, Comparative Example 96

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 82.

Comparative Example 97

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 83.

Example 98, Comparative Example 98

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 84.

Example 99, Comparative Example 99

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 85.

Example 100, Comparative Example 100

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 86.

Example 101, Comparative Example 101

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 87.

Example 102, Comparative Example 102

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 88.

Example 103, Comparative Example 103

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 89.

Example 104

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 90.

Example 105, Comparative Example 105

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 91.

Comparative Example 106

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 92.

Example 107, Comparative Example 107

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 93.

Example 108, Comparative Example 108

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 94.

Example 109, Comparative Example 109

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 95.

Example 110, Comparative Example 110

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 96.

Example 111, Comparative Example 111

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 97.

Example 112, Comparative Example 112

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 98.

Example 113

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 99.

Example 114, Comparative Example 114

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 100.

Comparative Example 115

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 101.

Example 116, Comparative Example 116

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 102.

Example 117, Comparative Example 117

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 103.

Example 118, Comparative Example 118

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 104.

Example 119, Comparative Example 119

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 105.

Example 120, Comparative Example 120

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 106.

Example 121, Comparative Example 121

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 107.

Example 122

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 108.

Example 123, Comparative Example 123

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 109.

Comparative Example 124

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 110.

Example 125, Comparative Example 125

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 111.

Example 126, Comparative Example 126

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 112.

Example 127, Comparative Example 127

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 113.

Example 128, Comparative Example 128

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 114.

Example 129, Comparative Example 129

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 115.

Example 130, Comparative Example 130

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). A result is shown in Table 116.

Example 131

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 117.

Example 132, Comparative Example 132

An organic EL device was produced and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 118.

From the results in Tables 1 to 118, when the compound of the present invention having a deuterium atom at a specific site is used in the light emitting layer of the organic EL element, the life of the organic EL element is longer than when a compound having no deuterium atom is used at the site. it can be seen that Further, from the comparison between Example 3 and Comparative Example 3-2, it can be seen that even in the case of a compound having a deuterium atom at a specific site, the lifespan of the organic EL device can be prolonged by adopting the structure of the present invention.

Although embodiments and/or examples of the present invention have been described in some detail above, those skilled in the art can make many changes to these illustrative embodiments and/or examples without substantially departing from the novel teachings and effects of the present invention. It is easy to add Accordingly, many modifications thereof are included within the scope of the present invention.

All the documents described in this specification and the application content on which the priority under the Paris Convention of the present application is based are incorporated herein by reference.

Claims (27)

A compound represented by the following formula (1).

(in formula (1),
R ₁ to _{R 8} are each independently
hydrogen atom,
A substituted or unsubstituted C1-C50 alkyl group;
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 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
It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to _{R 907} are each independently
hydrogen atom,
A substituted or unsubstituted C1-C50 alkyl group;
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms;
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or
It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ ~R ₉₀₇ a, if present more than one, each of the two or more R ₉₀₁ ~R ₉₀₇ may be subjected to may be the same different.
At least one of R ₁ to _{R 8} is a deuterium atom.
Adjacent two or more of R ₁ to _{R 4} and adjacent two or more of R ₅ to _{R 8} are not bonded to each other to form a ring.
L ₁ and L ₂ are each independently
single bond,
A substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or
It is a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
Ar ₁ is
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or
It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
Ar ₂ is a monovalent group represented by the following formula (2), (3) or (4).

In formulas (2) to (4),
One or more pairs of adjacent two of R ₁₅ to _{R 20} combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.
When _{one or more pairs of adjacent two of R 15} to _{R 20} combine with each other to not form a substituted or unsubstituted saturated or unsaturated ring, one of _{R 13} to _{R 20} is a single bond bonded to _{L 2 .}
When _{one or more pairs of adjacent R 15} to _{R 20} combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, R ₁₅ to R which does not form the substituted or unsubstituted saturated or unsaturated ring ₂₀ , and one of R ₁₃ and R ₁₄ is a single bond bonded to _{L 2 .
R 13} to _{R 20} , and R ₁₁ and R ₁₂ which do not form the substituted or unsubstituted saturated or unsaturated ring and are not a single bond bonded to _{L 2} are each independently
hydrogen atom,
A substituted or unsubstituted C1-C50 alkyl group;
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 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
It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to _{R 907} are as defined in Formula (1) above.) The compound according to claim 1, wherein at least two of _{R 1} to _{R 8 are deuterium atoms.} The compound according to claim 1 or 2, wherein R ₁ to _{R 8} are all deuterium atoms. The unsubstituted arylene group having 6 to 30 ring carbon atoms according to any one of claims 1 to 3, wherein _{at least one selected from the group consisting of L 1} and L ₂ is a deuterium atom in which at least one hydrogen atom is a deuterium atom. , or an unsubstituted divalent heterocyclic group having 5 to 30 ring atoms in which at least one of the hydrogen atoms is a deuterium atom. The compound according to any one of claims 1 to 4, wherein L ₁ and L ₂ are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms. The compound according to any one of claims 1 to 5, wherein R ₁₃ or R ₁₄ is a single bond bonded to _{L 2 .} The compound according to any one of claims 1 to 6, wherein at _{least one pair of adjacent two of R 15} to _{R 20} do not combine with each other to form a substituted or unsubstituted saturated or unsaturated ring. The method according to any one of claims 1 to 7, wherein Ar ₁ is an unsubstituted aryl group having 6 to 50 ring carbon atoms in which at least one of the hydrogen atoms is a deuterium atom, or at least one of the hydrogen atoms is a deuterium atom A compound which is an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. The compound according to any one of claims 1 to 8, wherein Ar ₁ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. The compound according to claim 9, wherein Ar ₁ is selected from groups represented by the following formulas (a1) to (a4).

(In formulas (a1) to (a4), * is a single bond bonded to _{L 1 .}
R ₂₁ is
A substituted or unsubstituted C1-C50 alkyl group;
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 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
It is 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).
m1 is an integer of 0-4.
m2 is an integer of 0-5.
m3 is an integer of 0-7.
When each of m1 to m3 is 2 or more, a plurality of R ₂₁ may be the same as or different from each other.
When each of m1 to m3 is 2 or more, a plurality of adjacent R ₂₁ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring is not formed.) 11. The method according to any one of claims 1 to 10, wherein the substituted or unsubstituted saturated or unsaturated ring is not formed and is not a single bond bonded to _{L 2 R 13} to _{R 20} , and R ₁₁ and A compound wherein at least one of _{R 12 is a deuterium atom.} According to claim 1, wherein the compound represented by the formula (1) is the following formula (1-1), (1-2), (1-3), (1-4), (1-5) or (1) The compound which is a compound represented by -6).

(In formulas (1-1), (1-2), (1-3), (1-4), (1-5) and (1-6), R ₁ to _{R 8} , R ₁₁ to _{R 20} , Ar ₁ , L ₁ and L ₂ are as defined in Formula (1).) According to claim 1, wherein the compound represented by the formula (1) is the following formula (1-11), (1-12), (1-13), (1-14), (1-15) or (1) -16), which is a compound represented by

(in formulas (1-11), (1-12), (1-13), (1-14), (1-15) and (1-16), R ₁ to _{R 8} , Ar ₁ and L ₁ is as defined in Equation (1) above.) According to claim 1, wherein the compound represented by the formula (1) is the following formula (1-21), (1-22), (1-23), (1-24), (1-25) or (1) -26) is a compound represented by the compound.

(In formulas (1-21), (1-22), (1-23), (1-24), (1-25) and (1-26), Ar ₁ and L ₁ are represented by Formula (1) as defined in .) 15. The compound according to any one of claims 1 to 14, which is a material for an organic electroluminescent device. 16. A composition comprising the compound according to any one of claims 1 to 15, wherein the compound represented by the formula (1) is a compound represented by the formula (1), except that the compound represented by the formula (1) contains only a light hydrogen atom as a hydrogen atom. A composition having a content ratio of the latter to the total of the compound having the same structure as 99 mol% or less. cathode and
anode and
one or two or more organic layers disposed between the cathode and the anode
has,
At least one of the organic layers contains the compound according to any one of claims 1 to 15 or the composition according to claim 16
Organic electroluminescent device. The organic electroluminescent device according to claim 17, wherein the organic layer comprises a light emitting layer, and the light emitting layer comprises the compound. 19. The group according to claim 17 or 18, wherein the light emitting layer is composed of the following formulas (11), (21), (31), (41), (51), (61), (71) and (81). An organic electroluminescent device further comprising at least one compound selected from

(in formula (11),
One or more pairs of two or more adjacent to each other among R ₁₀₁ to _{R 110} do not form a substituted or unsubstituted saturated or unsaturated ring or a substituted or unsubstituted saturated or unsaturated ring by combining them.
At least one of R ₁₀₁ to _{R 110} is a monovalent group represented by the following formula (12).
_{R 101} to _{R 110} which do not form the substituted or unsubstituted saturated or unsaturated ring and are not a monovalent group represented by the following formula (12) are each independently
hydrogen atom,
A substituted or unsubstituted C1-C50 alkyl group;
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 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
It is 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 formula (12), Ar ₁₀₁ and Ar ₁₀₂ are each independently
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or
It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
L _{101 to L 103} are each independently
single bond,
A substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or
It is a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.)

(in formula (21),
each Z is independently CR _a or N.
A1 ring and A2 ring are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.
When R _a multiple presence, the plurality of R and _a 2 more than one set or more adjacent ones are bonded to each other substituted or unsubstituted, saturated or forms a ring having an unsaturated, or the chain of a saturated or unsaturated, substituted or unsubstituted does not form
When R _b is a plurality is present, more than one trillion or more adjacent ones of the plurality of R _b are bonded to each other or form a ring, saturated or unsaturated, substituted or unsubstituted, or a cyclic saturated or unsaturated substituted or unsubstituted does not form
When R _c has a plurality is present, adjacent ones of the plurality of R _c 2 at least one set or more are bonded to each other or form a ring, saturated or unsaturated, substituted or unsubstituted, or a cyclic saturated or unsaturated substituted or unsubstituted does not form
n21 and n22 are each independently an integer of 0-4.
_{R a} to _{R c} that do not form a substituted or unsubstituted saturated or unsaturated ring are each independently
hydrogen atom,
A substituted or unsubstituted C1-C50 alkyl group;
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 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
It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to _{R 907} are as defined in Formula (1) above.)

(in formula (31),
At _{least one pair of adjacent two or more of R 301} to _{R 307} and R ₃₁₁ to _{R 317} does not form a substituted or unsubstituted saturated or unsaturated ring or a substituted or unsubstituted saturated or unsaturated ring.
_{R 301} to _{R 307} and R ₃₁₁ to _{R 317} which do not form a substituted or unsubstituted saturated or unsaturated ring are each independently
hydrogen atom,
A substituted or unsubstituted C1-C50 alkyl group;
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 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
It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₃₂₁ and R ₃₂₂ are each independently
hydrogen atom,
A substituted or unsubstituted C1-C50 alkyl group;
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 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
It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to _{R 907} are as defined in Formula (1) above.)

(in formula (41),
ring a, ring b and ring c are each independently
A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or
It is a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.
R ₄₀₁ and R ₄₀₂ are each independently combined with the a ring, b ring or c ring to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle.
_{R 401} and R ₄₀₂ that do not form the substituted or unsubstituted heterocycle are each independently
A substituted or unsubstituted C1-C50 alkyl group;
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 carbon atoms;
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or
It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.)

(in formula (51),
The r ring is a ring represented by Formula (52) or Formula (53) condensed at any position of an adjacent ring.
The q ring and the s ring are each independently a ring represented by the formula (54) condensed at any position in the adjacent ring.
The p-ring and the t-ring are each independently a structure represented by the formula (55) or (56) condensed at any position in the adjacent ring.
When R ₅₀₁ is a plurality is present, bonded to each other is a plurality of R ₅₀₁ adjacent to form a ring, saturated or unsaturated substituted or unsubstituted, or do not form a ring, saturated or unsaturated substituted or unsubstituted.
X ₅₀₁ is an oxygen atom, a sulfur atom, or NR ₅₀₂ .
_{R 501} and R ₅₀₂ that do not form the substituted or unsubstituted saturated or unsaturated ring are
hydrogen atom,
A substituted or unsubstituted C1-C50 alkyl group;
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 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
It is 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).
Ar ₅₀₁ and Ar ₅₀₂ are each independently
A substituted or unsubstituted C1-C50 alkyl group;
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 carbon atoms;
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or
It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
L ₅₀₁ silver
A substituted or unsubstituted alkylene group having 1 to 50 carbon atoms;
A substituted or unsubstituted alkenylene group having 2 to 50 carbon atoms;
A substituted or unsubstituted alkynylene group having 2 to 50 carbon atoms;
A substituted or unsubstituted cycloalkylene group having 3 to 50 ring carbon atoms;
A substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or
It is a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.
m1 is an integer from 0 to 2, m2 is an integer from 0 to 4, m3 is each independently an integer from 0 to 3, and m4 is each independently an integer from 0 to 5. When R ₅₀₁ is a plurality is present, a plurality of R ₅₀₁ may be subjected to a phase may be the same or different.)

(in formula (61),
At least one set of R ₆₀₁ and R ₆₀₂ , R ₆₀₂ and R ₆₀₃ , and R ₆₀₃ and R ₆₀₄ is bonded to each other to form a divalent group represented by the following formula (62).
At least one set of R ₆₀₅ and R ₆₀₆ , R ₆₀₆ and R ₆₀₇ , and R ₆₀₇ and R ₆₀₈ is bonded to each other to form a divalent group represented by the following formula (63).

At least one of R ₆₀₁ to _{R 604} that does not form a divalent group represented by the formula (62), and _{at least one of R 611} to _{R 614} is a monovalent group represented by the following formula (64).
At least one of R ₆₀₅ to _{R 608} that does not form a divalent group represented by the formula (63), and _{at least one of R 621} to _{R 624} is a monovalent group represented by the following formula (64).
X ₆₀₁ is an oxygen atom, a sulfur atom, or NR ₆₀₉ ;
_{R 601} to _{R 608 that} does not form a divalent group represented by the formulas (62) and (63), and is not a monovalent group represented by the formula (64), and is not a monovalent group represented by the formula (64) R ₆₁₁ to _{R 614} and R ₆₂₁ to _{R 624} , and R ₆₀₉ are each independently
hydrogen atom,
A substituted or unsubstituted C1-C50 alkyl group;
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 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
It is 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 formula (64), Ar ₆₀₁ and Ar ₆₀₂ are each independently
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or
It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
L _{601 to L 603} are each independently
single bond,
a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms;
A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or
It is a divalent linking group formed by bonding 2 to 4 of them.)

(in formula (71),
A ₇₀₁ ring and A ₇₀₂ ring are each independently
A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or
It is a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.
At _{least one selected from the group consisting of A 701} ring and A ₇₀₂ ring is bonded to the number of bonds * of the structure represented by the following formula (72).

In formula (72),
A ₇₀₃ rings are each independently
A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or
It is a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.
X ₇₀₁ is NR ₇₀₃ , C(R ₇₀₄ )(R ₇₀₅ ), Si(R ₇₀₆ )(R ₇₀₇ ), Ge(R ₇₀₈ )(R ₇₀₉ ), O, S or Se.
R ₇₀₁ and R ₇₀₂ combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.
_{R 701} and R ₇₀₂ that do not form a substituted or unsubstituted saturated or unsaturated ring, and R ₇₀₃ to _{R 709} are each independently
hydrogen atom,
A substituted or unsubstituted C1-C50 alkyl group;
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 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
It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to _{R 907} are as defined in Formula (1) above.)

(in formula (81),
The A ₈₀₁ ring is a ring represented by the formula (82) condensed at any position of an adjacent ring.
A ₈₀₂ ring is a ring represented by formula (83) condensed at any position of an adjacent ring. Two bonding numbers* bond at any position on the _{A 803 ring.}
X ₈₀₁ and X ₈₀₂ are each independently C(R ₈₀₃ )(R ₈₀₄ ), Si(R ₈₀₅ )(R ₈₀₆ ), an oxygen atom, or a sulfur atom.
A ₈₀₃ ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.
Ar ₈₀₁ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or
It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₈₀₁ to _{R 806} are each independently
hydrogen atom,
A substituted or unsubstituted C1-C50 alkyl group;
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 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
It is 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).
m801 and m802 are each independently an integer of 0-2. When these are 2, a plurality of R ₈₀₁ or R ₈₀₂ may be the same as or different from each other.
a801 is an integer from 0 to 2. When a801 is 0 or 1, the structures in parentheses indicated by "3-a801" may be the same as or different from each other. When a801 is 2, Ar ₈₀₁ may be the same as or different from each other.) The organic electroluminescent device according to claim 19, wherein in the formula (11), _{two of R 101} to _{R 110} are groups represented by the formula (12). The organic electroluminescent device according to claim 19 or 20, wherein the compound represented by the formula (11) is a compound represented by the following formula (13).

(In Formula (13), R ₁₁₁ to _{R 118} are the same as _{R 101} to _{R 110 which} is not a monovalent group represented by Formula (12) in Formula (11) _{. Ar 101} , Ar ₁₀₂ , L ₁₀₁ , L ₁₀₂ and L ₁₀₃ are as defined in Equation (12) above.) The organic electroluminescent device according to claim 21, wherein the compound represented by the formula (13) is a compound represented by the following formula (14).

(In Formula (14), R ₁₁₁ to _{R 118} are as defined in Formula (13). Ar ₁₀₁ , Ar ₁₀₂ , L ₁₀₂ and L ₁₀₃ are as defined in Formula (12).) The organic electroluminescent device according to claim 21, wherein the compound represented by the formula (13) is a compound represented by the following formula (15).

(In Formula (15), R ₁₁₁ to _{R 118} are as defined in Formula (13). Ar ₁₀₁ and Ar ₁₀₂ are as defined in Formula (12).) The organic electroluminescent device according to claim 21, wherein the compound represented by the formula (13) is a compound represented by the following formula (17).

(In the formula (17), R ₁₁₁ to _{R 118} are as defined in the formula (13).
Among R ₁₂₁ to _{R 127} , at least one pair of adjacent two or more are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring is not formed.
_{R 121} to _{R 127} which do not form the substituted or unsubstituted saturated or unsaturated ring are each independently
hydrogen atom,
A substituted or unsubstituted C1-C50 alkyl group;
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 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
It is 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).
R ₁₃₁ to _{R 135} are each independently
hydrogen atom,
A substituted or unsubstituted C1-C50 alkyl group;
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 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
It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to _{R 907} are as defined in Formula (1) above.) The organic electroluminescent device according to any one of claims 17 to 24, having a hole transport layer between the anode and the light emitting layer. The organic electroluminescent device according to any one of claims 17 to 25, having an electron transporting layer between the cathode and the light emitting layer. An electronic device provided with the organic electroluminescent element in any one of Claims 17-26.