KR20230142716A - Compounds, materials for organic electroluminescent devices, organic electroluminescent devices and electronic devices - Google Patents

Abstract

Includes compounds represented by the following formula (1) or formula (2) (each symbol in each formula is as defined in the specification), organic electroluminescent devices containing the compounds, and such organic electroluminescent devices. electronic devices that do.

Description

Compounds, materials for organic electroluminescent devices, organic electroluminescent devices and electronic devices

The present invention relates to compounds, materials for organic electroluminescent devices, organic electroluminescent devices, and electronic devices containing the organic electroluminescent devices.

Generally, an organic electroluminescence device (hereinafter sometimes referred to as an "organic EL device") is composed of an anode, a cathode, and an organic layer sandwiched between the anode and the cathode. When a voltage is applied between both electrodes, electrons from the cathode side and holes from the anode side are injected into the light-emitting region. The injected electrons and holes recombine in the light-emitting region to create an excited state, and the excited state returns to the ground state. It emits light when it comes. Therefore, the development of materials that efficiently transport electrons or holes to the light-emitting region and facilitate recombination of electrons and holes is important in obtaining high-performance organic EL devices.

Patent Documents 1 to 7 disclose compounds used as materials for organic electroluminescent devices.

International Publication No. 2013/077352 Korean Patent Publication No. 10-2020-0068398 Korean Patent Publication No. 10-2017-0096769 International Publication No. 2020/022769 US Patent Application Publication No. 2020/227658 Specification Chinese Patent Publication No. 111072637 US Patent Application Publication No. 2019/363260 Specification

Conventionally, many compounds for organic EL devices have been reported, but there is still a need for compounds that further improve the performance of organic EL devices.

The present invention was made to solve the above problems, and provides a compound that further improves the performance of an organic EL device, an organic EL device with further improved device performance, and an electronic device including such an organic EL device. The purpose.

The present inventors conducted intensive studies on the performance of organic EL devices containing the compounds described in Patent Documents 1 to 7, and as a result, an organic EL device containing a compound represented by the following formula (1) and the following formula (2) It was discovered that the performance of an organic EL device containing a compound represented by ) is further improved.

In one aspect, the present invention provides a compound represented by the following formula (1).

[Formula 1]

(In equation (1),

Ar ¹ to ^{Ar 3} each independently represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

L ¹ is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, and Ar ² and L ¹ are bonded to each other to form a substituted or unsubstituted arylene group. An unsubstituted ring may be formed.

L ² is a single bond or a 2+p-valent residue of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 25 ring carbon atoms.

p is 0 or 1, when L ² is a single bond, p is 0, and when L ² is a 2+p valent residue of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 25 ring carbon atoms, p is 0 or 1.

R ¹ to R ⁶ and R ¹¹ to ^{R 14} are each independently,

hydrogen atom,

halogen Atom,

Cyanogi,

nitrogi,

A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

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 group represented by Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

A group represented by -O-(R ₉₀₄ ),

A group represented by -S-(R ₉₀₅ ),

A group represented by -N(R ₉₀₆ )(R ₉₀₇ ),

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

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

R ₉₀₁ to R ₉₀₇ are each independently,

hydrogen atom,

A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

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

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

When two or more R _901s exist, the two or more R _901s are the same as or different from each other,

When two or more R _902s exist, the two or more R _902s are the same as or different from each other,

When two or more R ₉₀₃ exist, the two or more R ₉₀₃ are the same as or different from each other,

When two or more R _904s exist, the two or more R _904s are the same as or different from each other,

When two or more R _905s exist, the two or more R _905s are the same as or different from each other,

When two or more R _906s exist, the two or more R _906s are the same as or different from each other,

When two or more R _907s exist, the two or more R _907s are the same or different from each other,

R ¹ and R ² do not combine with each other to form a ring,

In one or more groups selected from R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ¹¹ and R ¹² , R ¹² and R ¹³ , and R ¹³ and R ¹⁴ , two adjacent ones are bonded to each other Thus, a substituted or unsubstituted ring may be formed.

X ¹ is an oxygen atom or a sulfur atom.

*d is bonded to one carbon atom selected from *a, *b, and *c.)

In another aspect, the present invention provides a compound represented by the following formula (2).

[Formula 2]

(In equation (2),

Ar ¹¹ to ^{Ar 13} each independently represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

L ¹¹ is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, and Ar ¹² and L ¹² are bonded to each other to form a substituted or unsubstituted arylene group. An unsubstituted ring may be formed.

L ¹² is a 2+q valent residue of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 25 ring carbon atoms.

q is 0 or 1.

R ⁴¹ to R ⁴⁶ and R ⁵¹ to ^{R 54} are each independently,

hydrogen atom,

halogen Atom,

Cyanogi,

nitrogi,

A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

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 group represented by Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

A group represented by -O-(R ₉₀₄ ),

A group represented by -S-(R ₉₀₅ ),

A group represented by -N(R ₉₀₆ )(R ₉₀₇ ),

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

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

R ₉₀₁ to R ₉₀₇ are each independently,

hydrogen atom,

A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

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

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

When two or more R _901s exist, the two or more R _901s are the same as or different from each other,

When two or more R _902s exist, the two or more R _902s are the same as or different from each other,

When two or more R ₉₀₃ exist, the two or more R ₉₀₃ are the same as or different from each other,

When two or more R _904s exist, the two or more R _904s are the same as or different from each other,

When two or more R _905s exist, the two or more R _905s are the same as or different from each other,

When two or more R _906s exist, the two or more R _906s are the same as or different from each other,

When two or more R _907s exist, the two or more R _907s are the same or different from each other,

R ⁴¹ and R ⁴² do not combine with each other to form a ring,

In one or more groups selected from R ⁴³ and R ⁴⁴ , R ⁴⁴ and R ⁴⁵ , R ⁴⁵ and R ⁴⁶ , R ⁵¹ and R ⁵² , R ⁵² and R ⁵³ , and R ⁵³ and R ⁵⁴ , two adjacent ones are bonded to each other Thus, a substituted or unsubstituted ring may be formed.

X ¹¹ is an oxygen atom or a sulfur atom.)

In another aspect, the present invention provides a material for an organic electroluminescent device having at least one selected from the compound represented by the formula (1) and the compound represented by the formula (2).

In another aspect, the present invention is an organic electroluminescent device having a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer includes a light-emitting layer, and at least one layer of the organic layer has the formula above: An organic electroluminescent device comprising at least one selected from the compound represented by (1) and the compound represented by the formula (2) is provided.

In another aspect, the present invention provides an electronic device including the organic electroluminescent device.

An organic EL device containing the compound represented by formula (1) above exhibits improved device performance. Additionally, organic EL devices containing the compound represented by formula (2) exhibit improved device performance.

1 is a schematic diagram showing an example of the layer structure of an organic EL device according to one aspect of the present invention.
Figure 2 is a schematic diagram showing another example of the layer structure of an organic EL device according to one aspect of the present invention.

[Justice]

In this specification, hydrogen atoms include isotopes with different numbers of neutrons, that is, protium, deuterium, and 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. Pretend it exists.

In this specification, the number of ring-forming carbon atoms refers to the number of atoms constituting the ring itself of compounds having a structure in which atoms are bonded in a ring (e.g., monocyclic compounds, condensed ring compounds, cross-linked compounds, carbocyclic compounds, and heterocyclic compounds). Indicates the number of carbon atoms. When the ring is substituted by a substituent, the carbon included in the substituent is not included in the ring-forming carbon number. The same applies to the “ring-forming carbon number” described below, 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. Also, for example, the ring carbon number of the 9,9-diphenylfluorenyl group is 13, and the ring carbon number of the 9,9'-spirobifluorenyl group is 25.

In addition, when the benzene ring is substituted with a substituent, for example, an alkyl group, the carbon number of the alkyl group is not included in the ring carbon number of the benzene ring. Therefore, the ring carbon number of the benzene ring in which the alkyl group is substituted is 6. In addition, when the naphthalene ring is substituted with a substituent, for example, an alkyl group, the carbon number of the alkyl group is not included in the ring carbon number of the naphthalene ring. Therefore, the ring carbon number of the naphthalene ring in which the alkyl group is substituted is 10.

In this specification, the number of ring atoms refers to compounds (e.g., monocyclic compounds, condensed ring compounds, cross-linked compounds, carbocyclic compounds) with structures in which atoms are bonded in a ring (e.g., monocyclic, condensed ring, and ring set). , and heterocyclic compounds) indicates the number of atoms constituting the ring itself. Atoms that do not constitute a ring (for example, a hydrogen atom that terminates the bond of the atoms forming a ring) or atoms included in a substituent when the ring is substituted by a substituent are not included in the number of ring forming atoms. The “number of ring atoms” described below is the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to the pyridine ring or the atoms constituting the substituent is not included in the number of pyridine ring forming atoms. Therefore, the number of ring atoms of the pyridine ring to which the hydrogen atom or substituent is bonded is 6. In addition, for example, the hydrogen atom bonded to the carbon atom of the quinazoline ring or the atom constituting the substituent is not included in the number of ring forming atoms of the quinazoline ring. Therefore, the number of ring atoms of the quinazoline ring to which the hydrogen atom or substituent is bonded is 10.

In this specification, “carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group with carbon atoms XX to YY” refers to the carbon number when the ZZ group is unsubstituted, and refers to the number of carbon atoms when the ZZ group is substituted. Does not include carbon number. Here, “YY” is greater than “XX”, “XX” means an integer of 1 or more, and “YY” means an integer of 2 or more.

In this specification, “atom number XX to YY” in the expression “substituted or unsubstituted ZZ group with atom number XX to YY” indicates the number of atoms when the ZZ group is unsubstituted, and when the ZZ group is substituted, Do not include the number of atoms of the substituent. Here, “YY” is greater than “XX”, “XX” means an integer of 1 or more, and “YY” means an integer of 2 or more.

In this specification, an unsubstituted ZZ group refers to a case where a “substituted or unsubstituted ZZ group” is an “unsubstituted ZZ group,” and a substituted ZZ group refers to a case where a “substituted or unsubstituted ZZ group” refers to a “substituted ZZ group.” Indicates the case of “gi”.

In this specification, “unsubstituted” in the case of “substituted or unsubstituted ZZ group” means that the hydrogen atom in the ZZ group is not substituted with a substituent. The hydrogen atom in the “unsubstituted ZZ group” is a light hydrogen atom, a heavy hydrogen atom, or a tritium atom.

In addition, in this specification, “substitution” in the case of “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 “a BB group substituted with an AA group” similarly means that one or more hydrogen atoms in the BB group are substituted with an AA group.

“Substituents described in this specification”

Hereinafter, the substituents described in this specification will be described. Unless otherwise stated, each substituent described in this specification is defined as follows.

The ring carbon number of the “unsubstituted aryl group” described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

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

The carbon number of the “unsubstituted alkyl group” described in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise stated in this specification.

The carbon number of the “unsubstituted alkenyl group” described in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise stated in this specification.

The carbon number of the “unsubstituted alkynyl group” described in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified in this specification.

The ring carbon number of the “unsubstituted cycloalkyl group” described in this specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise stated in this specification.

The ring carbon number of the “unsubstituted arylene group” described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

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

The carbon number of the “unsubstituted alkylene group” described in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise stated in this specification.

· 「Substituted or unsubstituted aryl group」

Specific examples of the “substituted or unsubstituted aryl group” (specific example group G1) described in this specification include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B). . (Here, an unsubstituted aryl group refers to a case where a “substituted or unsubstituted aryl group” is an “unsubstituted aryl group”, and a substituted aryl group refers to a case where a “substituted or unsubstituted aryl group” is a “substituted aryl group”. ".) In this specification, when simply referred to as an "aryl group", it includes both an "unsubstituted aryl group" and a "substituted aryl group."

“Substituted aryl group” means a group in which one or more hydrogen atoms of an “unsubstituted aryl group” are replaced with a substituent. Examples of the “substituted aryl group” include, for example, a group in which one or more hydrogen atoms of the “unsubstituted aryl group” of the specific example group G1A below are replaced with a substituent, and examples of the substituted aryl group of the specific example group G1B below. I can hear it. Meanwhile, the examples of “unsubstituted aryl group” and “substituted aryl group” listed here are only examples, and the “substituted aryl group” described in this specification includes “ A group in which the hydrogen atom bonded to the carbon atom of the aryl group itself in the “substituted aryl group” is further substituted with a substituent, and a group in which the hydrogen atom of the substituent in the “substituted aryl group” of the specific example group G1B below is further substituted with a substituent. Prayer is included.

· Unsubstituted aryl group (specific example group G1A):

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,

m-terphenyl-3'-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,

benzantryl group,

phenanthryl group,

benzophenanthryl group,

Penalen diary,

Piran Diary,

Crysen Diary,

Benzokreisen diary,

triphenylene group,

benzotriphenylene group,

tetracene diary,

Pentacene diary,

fluorene diary,

9,9'-spirobifluorene group,

benzofluorene diyl,

Dibenzofluorene diary,

fluoranthene diary,

benzofluoranthene diary,

perylene group, and

A monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

[Formula 3]

[Formula 4]

· Substituted aryl group (specific example group G1B):

o-tolyl group,

m-tolyl group,

p-tolyl group,

para-xylyl group,

meta-xylyl group,

ortho-xylyl group,

para-isopropylphenyl group,

meta-isopropylphenyl group,

ortho-isopropylphenyl group,

para-t-butylphenyl group,

meta-t-butylphenyl group,

ortho-t-butylphenyl group,

3,4,5-trimethylphenyl group,

9,9-dimethylfluorenyl group,

9,9-diphenylfluorenyl group

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

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

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

cyanophenyl group,

Triphenylsilylphenyl group,

trimethylsilylphenyl group,

phenylnaphthyl group,

a naphthylphenyl group, and

A group in which one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the above general formulas (TEMP-1) to (TEMP-15) are replaced with a substituent.

· 「Substituted or unsubstituted heterocyclic group」

The “heterocyclic group” described in this specification is a cyclic group containing at least one hetero atom in the ring forming atom. Specific examples of heteroatoms include nitrogen atom, oxygen atom, sulfur atom, silicon atom, phosphorus atom, and boron atom. The “heterocyclic group” described in this specification is a monocyclic group or a condensed ring group.

The “heterocyclic group” described in this specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

Specific examples of the “substituted or unsubstituted heterocyclic group” (specific example group G2) described in this specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). there is. (Here, unsubstituted heterocyclic group refers to the case where “substituted or unsubstituted heterocyclic group” is “unsubstituted heterocyclic group”, and substituted heterocyclic group refers to the case where “substituted or unsubstituted heterocyclic group” is “substituted heterocyclic group”. Refers to the case of “heterocyclic group”.) In this specification, simply referring to “heterocyclic group” includes both “unsubstituted heterocyclic group” and “substituted heterocyclic group.”

“Substituted heterocyclic group” means a group in which one or more hydrogen atoms of the “unsubstituted heterocyclic group” are replaced with a substituent. Specific examples of the “substituted heterocyclic group” include a group in which the hydrogen atom of the “unsubstituted heterocyclic group” in the specific example group G2A below is substituted, and examples of the substituted heterocyclic group in the specific example group G2B below. Meanwhile, the examples of “unsubstituted heterocyclic group” and “substituted heterocyclic group” listed here are only examples, and the “substituted heterocyclic group” described in this specification includes “substituted heterocyclic group” of specific example group G2B. Included are groups in which the hydrogen atom bonded to the ring-forming atom of the heterocyclic group itself in “ventilation” is further substituted with a substituent, and groups in which the hydrogen atom of the substituent in the “substituted heterocyclic group” of specific example group G2B is further substituted with a substituent. .

Specific example group G2A includes, for example, an unsubstituted heterocyclic group containing the following nitrogen atom (specific example group G2A1), an unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2), and an unsubstituted heterocyclic group containing a sulfur atom. heterocyclic group (specific example group G2A3), and a monovalent heterocyclic group (specific example group G2A4) derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) Includes.

Specific examples group G2B include, for example, a substituted heterocyclic group containing the following nitrogen atom (specific example group G2B1), a substituted heterocyclic group containing an oxygen atom (specific example group G2B2), and a substituted heterocyclic group containing a sulfur atom. (specific example group G2B3), and a group in which at least one hydrogen atom of a monovalent heterocyclic group derived from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) is substituted with a substituent (specific example group G2B4) Includes.

· Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1):

pyrrolyl group,

imidazolyl group,

pyrazolyl group,

triazolyl group,

tetrazolyl group,

Oxazolyl group,

isoxazolylgi,

Oxadiazolyl group,

thiazolyl group,

Isothiazolyl group,

Cyadiazolyl group,

pyridyl group,

Piri Dajin Diary,

pyrimidine diary,

Pyrazine diary,

triazine diary,

indolyl group,

Isoin rolling machine,

indolizine diary,

Quinolizine diary,

quinolyl group,

isoquinolyl group,

Shinnolilgi,

Phthalazine diary,

Quinazoline diary,

quinoxaline diary,

Benzimidazolyl group,

indazolyl group,

phenanthroline diary,

phenanthridine diary,

Acridine diary,

phenazine diary,

carbazolyl group,

benzocarbazolyl group,

morpholino group,

Phenoc photo diary,

Phenothiazine diary,

azacarbazolyl group, and

Diazacabazolyl group.

· Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2):

furyl group,

Oxazolyl group,

isoxazolylgi,

Oxadiazolyl group,

Janten Diary,

benzofuran diary,

Isobenzofuran diary,

dibenzofuran diary,

Naphthobenzofuran diary,

Benzoxazolyl group,

Benz isoxazolyl group,

Phenoc photo diary,

morpholino group,

Dynaptofuran diary,

Azadibenzofuran diary,

Diazadaibenzofuran diary,

Azanaphthobenzofuran diary, and

Diazanapthobenzofuran diary.

· Unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3):

CyN Diary,

thiazolyl group,

Isothiazolyl group,

Cyadiazolyl group,

Benzothiophen diary (benzothiene diary),

Isobenzothiophene diary (Isobenzothiene diary),

Dibenzothiophene diary (Dibenzothiene diary),

Naphthobenzothiophene diary (Naphthobenzothiene diary),

Benzothiazolyl group,

Benzisothiazolyl group,

Phenothiazine diary,

Dynaphthothiophen diary (Dynaphthothiene diary),

Azadibenzothiophene diary (azadibenzothiene diary),

Diaza diebenzothiophen diary (Diazadibenzothiene diary),

Azanaphthobenzothiophene diyl (azanaphthobenzothiene diyl), and

Diazanapthobenzothiophene diary (Diazanaphthobenzothiene diary).

· Monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

[Formula 5]

[Formula 6]

In the above general formulas (TEMP-16) to (TEMP-33), X _A and Y _A are each independently an oxygen atom, a sulfur atom, NH, or CH ₂ . However, at least one of X _A and Y _A is an oxygen atom, a sulfur atom, or NH.

In the general formulas (TEMP-16) to (TEMP-33), when at least one of X _A and Y _A is NH or CH ₂ , the general formulas (TEMP-16) to (TEMP-33) The monovalent heterocyclic group derived from the indicated ring structure includes a monovalent group obtained by removing one hydrogen atom from NH or CH ₂ .

· Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1):

(9-phenyl)carbazolyl group,

(9-biphenylyl)carbazolyl group,

(9-phenyl)phenylcarbazolyl group,

(9-naphthyl)carbazolyl group,

Diphenylcarbazole-9-yl group,

phenylcarbazole-9-yl group,

Methylbenzimidazolyl group,

Ethylbenzimidazolyl group,

phenyltriazine diary,

biphenylyl triazine diyl,

Diphenyltriazine diary,

phenylquinazolinyl group, and biphenylylquinazolinyl group.

· Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

phenyldibenzofuran diary,

Methyldibenzofuranyl group,

t-butyldibenzofuranyl group, and

Monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

· Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):

phenyldibenzothiophenyl,

Methyl dibenzothiophenyl group,

t-butyldibenzothiophenyl group, and

Monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

· A group in which at least one hydrogen atom of a monovalent heterocyclic group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) is substituted with a substituent (specific example group G2B4):

The above-mentioned “one or more hydrogen atoms of a monovalent heterocyclic group” refers to a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, or a nitrogen atom when at least one of X _A and Y _A is NH. It means one or more hydrogen atoms selected from the hydrogen atom of the methylene group and the hydrogen atom of the methylene group when one of X _A and Y _A is CH ₂ .

· 「Substituted or unsubstituted alkyl group」

Specific examples of the “substituted or unsubstituted alkyl group” (specific example group G3) described in this specification include the following unsubstituted alkyl group (specific example group G3A) and substituted alkyl group (specific example group G3B). (Here, an unsubstituted alkyl group refers to a case where the “substituted or unsubstituted alkyl group” is an “unsubstituted alkyl group”, and a substituted alkyl group refers to a case where the “substituted or unsubstituted alkyl group” is a “substituted alkyl group”. (Indicates.) Hereinafter, when simply referred to as “alkyl group”, it includes both “unsubstituted alkyl group” and “substituted alkyl group”.

“Substituted alkyl group” means a group in which one or more hydrogen atoms in the “unsubstituted alkyl group” are replaced with a substituent. Specific examples of the “substituted alkyl group” include a group in which one or more hydrogen atoms in the following “unsubstituted alkyl group” (specific example group G3A) is replaced with a substituent, and examples of a substituted alkyl group (specific example group G3B). You can. In this specification, the alkyl group in “unsubstituted alkyl group” means a chain-shaped alkyl group. Therefore, the “unsubstituted alkyl group” includes a straight-chain “unsubstituted alkyl group” and a branched “unsubstituted alkyl group”. Meanwhile, the examples of “unsubstituted alkyl group” and “substituted alkyl group” listed here are only examples, and the “substituted alkyl group” described in this specification includes the “substituted alkyl group” of specific example group G3B. Also included are groups in which the hydrogen atom of the alkyl group itself is further substituted with a substituent, and groups in which the hydrogen atom of the substituent in the "substituted alkyl group" of specific example group G3B is further substituted with a substituent.

· Unsubstituted alkyl group (specific example group G3A):

methyl group,

ethyl group,

n-profile group,

isopropyl group,

n-butyl group,

isobutyl group,

s-butyl group, and

t-butyl group.

· Substituted alkyl group (specific example group G3B):

Heptafluoropropyl group (including isomers),

pentafluoroethyl group,

2,2,2-trifluoroethyl group, and

Trifluoromethyl group.

· 「Substituted or unsubstituted alkene group」

Specific examples of the “substituted or unsubstituted alkenyl group” (specific example group G4) described in this specification include the following unsubstituted alkenyl group (specific example group G4A) and substituted alkenyl group (specific example group G4B). there is. (Here, unsubstituted alkenyl group refers to the case where “substituted or unsubstituted alkenyl group” is “unsubstituted alkenyl group”, and “substituted alkenyl group” refers to the case where “substituted or unsubstituted alkenyl group” is “ Refers to the case of “substituted alkenyl group”.) In this specification, when simply referred to as “alkenyl group”, it includes both “unsubstituted alkenyl group” and “substituted alkenyl group”.

“Substituted alkenyl group” means a group in which one or more hydrogen atoms in the “unsubstituted alkenyl group” are replaced with a substituent. Specific examples of the “substituted alkenyl group” include the following “unsubstituted alkenyl group” (specific example group G4A) having a substituent, and substituted alkenyl group (specific example group G4B). Meanwhile, the examples of “unsubstituted alkenyl group” and “substituted alkenyl group” listed here are only examples, and the “substituted alkenyl group” described in this specification includes “substituted alkene” of specific example group G4B. Groups in which the hydrogen atom of the alkenyl group itself in the group "is further substituted by a substituent" and groups in which the hydrogen atom of the substituent in the "substituted alkenyl group" of specific example group G4B are further substituted by a substituent are also included.

· Unsubstituted alkene group (specific example group G4A):

vinyl,

inform,

1-Buten Diary,

2-Buten Diary, and

3-Buten Diary.

· Substituted alkene group (specific example group G4B):

1,3-butane diene diary,

1-methylvinyl group,

1-methylallyl group,

1,1-dimethylallyl group,

2-methylallyl group, and

1,2-dimethylallyl group.

· 「Substituted or unsubstituted alkyne group」

Specific examples of the “substituted or unsubstituted alkynyl group” (specific example group G5) described in this specification include the following unsubstituted alkynyl group (specific example group G5A). (Here, unsubstituted alkyne group refers to the case where “substituted or unsubstituted alkyne group” is “unsubstituted alkyne group”.) Hereinafter, simply referred to as “alkyne group”, “unsubstituted alkyne group” refers to “unsubstituted alkyne group”. Includes both “alkyne group” and “substituted alkyne group”.

“Substituted alkynyl group” means a group in which one or more hydrogen atoms in the “unsubstituted alkynyl group” are replaced with a substituent. Specific examples of the “substituted alkynyl group” include groups in which one or more hydrogen atoms in the following “unsubstituted alkynyl group” (specific example group G5A) are substituted with a substituent.

· Unsubstituted alkyne group (specific example group G5A):

Ettin Diary

· 「Substituted or unsubstituted cycloalkyl group」

Specific examples of the “substituted or unsubstituted cycloalkyl group” (specific example group G6) described in this specification include the following unsubstituted cycloalkyl group (specific example group G6A) and substituted cycloalkyl group (specific example group G6B). there is. (Here, an unsubstituted cycloalkyl group refers to a case where a “substituted or unsubstituted cycloalkyl group” is an “unsubstituted cycloalkyl group”, and a substituted cycloalkyl group refers to a case where a “substituted or unsubstituted cycloalkyl group” is a “substituted or unsubstituted cycloalkyl group”. Refers to a case of a “cycloalkyl group.”) In this specification, simply referring to a “cycloalkyl group” includes both an “unsubstituted cycloalkyl group” and a “substituted cycloalkyl group.”

“Substituted cycloalkyl group” means a group in which one or more hydrogen atoms in the “unsubstituted cycloalkyl group” are replaced with a substituent. Specific examples of the “substituted cycloalkyl group” include groups in which one or more hydrogen atoms in the following “unsubstituted cycloalkyl group” (specific example group G6A) are substituted with a substituent, and examples of substituted cycloalkyl groups (specific example group G6B). etc. can be mentioned. Meanwhile, the examples of “unsubstituted cycloalkyl group” and “substituted cycloalkyl group” listed here are only examples, and the “substituted cycloalkyl group” described in this specification includes “substituted cycloalkyl group” of specific example group G6B. Includes groups in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group in the “alkyl group” itself is substituted with a substituent, and groups in which the hydrogen atom of the substituent in the “substituted cycloalkyl group” of specific example group G6B is further substituted with a substituent. do.

· Unsubstituted cycloalkyl group (specific example group G6A):

cyclopropyl machine,

cyclobutyl group,

cyclopentyl group,

cyclohexyl group,

1-adamantyl group,

2-adamantyl group,

1-norbornyl group, and

2-norbornyl group.

· Substituted cycloalkyl group (specific example group G6B):

4-methylcyclohexyl group.

· 「Group represented by -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ )」

Specific examples of the group represented by -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ) described herein (specific example group G7) are:

-Si(G1)(G1)(G1),

-Si(G1)(G2)(G2),

-Si(G1)(G1)(G2),

-Si(G2)(G2)(G2),

-Si(G3)(G3)(G3), and

-Si(G6)(G6)(G6)

can be mentioned. From here,

G1 is a “substituted or unsubstituted aryl group” described in specific example group G1.

G2 is a “substituted or unsubstituted heterocyclic group” described in specific example group G2.

G3 is a “substituted or unsubstituted alkyl group” described in specific example group G3.

G6 is a “substituted or unsubstituted cycloalkyl group” described in specific example group G6.

-A plurality of G1 in Si(G1)(G1)(G1) are the same as or different from each other.

-A plurality of G2 in Si(G1)(G2)(G2) is the same as or different from each other.

-A plurality of G1 in Si(G1)(G1)(G2) are the same as or different from each other.

-Si(G2)(G2)(G2) A plurality of G2 is the same as or different from each other.

-Si(G3)(G3)(G3) A plurality of G3 is the same as or different from each other.

-A plurality of G6 in Si(G6)(G6)(G6) is the same as or different from each other.

· 「Group represented by -O-(R ₉₀₄ )」

Specific examples of the group represented by -O-(R ₉₀₄ ) described in this specification (specific example group G8) are:

-O(G1),

-O(G2),

-O(G3), and

-O(G6)

can be mentioned.

From here,

G1 is a “substituted or unsubstituted aryl group” described in specific example group G1.

G2 is a “substituted or unsubstituted heterocyclic group” described in specific example group G2.

G3 is a “substituted or unsubstituted alkyl group” described in specific example group G3.

G6 is a “substituted or unsubstituted cycloalkyl group” described in specific example group G6.

· 「Group represented by -S-(R ₉₀₅ )」

Specific examples of the group represented by -S-(R ₉₀₅ ) described in this specification (specific example group G9) are:

-S(G1),

-S(G2),

-S(G3), and

-S(G6)

can be mentioned.

From here,

G1 is a “substituted or unsubstituted aryl group” described in specific example group G1.

G2 is a “substituted or unsubstituted heterocyclic group” described in specific example group G2.

G3 is a “substituted or unsubstituted alkyl group” described in specific example group G3.

G6 is a “substituted or unsubstituted cycloalkyl group” described in specific example group G6.

· 「Group represented by -N(R ₉₀₆ )(R ₉₀₇ )」

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), and

-N(G6)(G6)

can be mentioned. From here,

G1 is a “substituted or unsubstituted aryl group” described in specific example group G1.

G2 is a “substituted or unsubstituted heterocyclic group” described in specific example group G2.

G3 is a “substituted or unsubstituted alkyl group” described in specific example group G3.

G6 is a “substituted or unsubstituted cycloalkyl group” described in specific example group G6.

A plurality of G1 in -N(G1)(G1) are the same as or different from each other.

A plurality of G2s in -N(G2)(G2) are the same as or different from each other.

A plurality of G3s in -N(G3)(G3) are the same as or different from each other.

-A plurality of G6 in N(G6)(G6) are the same as or different from each other.

· 「Halogen atom」

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

· 「Substituted or unsubstituted fluoroalkyl group」

The “substituted or unsubstituted fluoroalkyl group” described in this specification means a group in which at least one hydrogen atom bonded to the carbon atom constituting the alkyl group in the “substituted or unsubstituted alkyl group” is substituted with a fluorine atom, In the “substituted or unsubstituted alkyl group”, a group (perfluoro group) in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group are substituted with fluorine atoms is also included. The carbon number of the “unsubstituted fluoroalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the specification. “Substituted fluoroalkyl group” means a group in which one or more hydrogen atoms of the “fluoroalkyl group” are replaced with a substituent. On the other hand, the “substituted fluoroalkyl group” described in this specification includes a group in which at least one hydrogen atom bonded to the carbon atom of the alkyl chain in the “substituted fluoroalkyl group” is further substituted with a substituent, and a “substituted fluoroalkyl group” Groups in which one or more hydrogen atoms of the substituent in the “roalkyl group” are further substituted with a substituent are also included. Specific examples of the “unsubstituted fluoroalkyl group” include groups in which one or more hydrogen atoms in the “alkyl group” (specific example group G3) are substituted with a fluorine atom.

· 「Substituted or unsubstituted haloalkyl group」

The “substituted or unsubstituted haloalkyl group” described in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom constituting the alkyl group in the “substituted or unsubstituted alkyl group” is substituted with a halogen atom, The “substituted or unsubstituted alkyl group” also includes groups in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group are substituted with halogen atoms. The carbon number of the “unsubstituted haloalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the specification. “Substituted haloalkyl group” means a group in which one or more hydrogen atoms of the “haloalkyl group” are replaced with a substituent. On the other hand, the “substituted haloalkyl group” described in this specification includes a group in which at least one hydrogen atom bonded to the carbon atom of the alkyl chain in the “substituted haloalkyl group” is further substituted with a substituent, and a “substituted haloalkyl group” Also included are groups in which one or more hydrogen atoms of the substituent are further substituted with a substituent. Specific examples of the “unsubstituted haloalkyl group” include groups in which one or more hydrogen atoms in the “alkyl group” (specific example group G3) are substituted with a halogen atom. Haloalkyl groups are sometimes referred to as halogenated alkyl groups.

· 「Substituted or unsubstituted alkoxy group」

A specific example of the “substituted or unsubstituted alkoxy group” described in this specification is a group represented by -O(G3), where G3 is a “substituted or unsubstituted alkyl group” described in specific example group G3. The carbon number of the “unsubstituted alkoxy group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the specification.

· 「Substituted or unsubstituted alkylthio group」

A specific example of the “substituted or unsubstituted alkylthio group” described in this specification is a group represented by -S(G3), where G3 is a “substituted or unsubstituted alkyl group” described in specific example group G3. The carbon number of the “unsubstituted alkylthio group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the specification.

· 「Substituted or unsubstituted aryloxy group」

A specific example of the “substituted or unsubstituted aryloxy group” described in this specification is a group represented by -O(G1), where G1 is a “substituted or unsubstituted aryl group” described in specific example group G1. . The ring carbon number of the “unsubstituted aryloxy group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the specification.

· 「Substituted or unsubstituted arylthio group」

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

· 「Substituted or unsubstituted trialkylsilyl group」

A specific example of the “trialkylsilyl group” described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a “substituted or unsubstituted alkyl group” described in specific example group G3. am. -Si(G3)(G3)(G3) A plurality of G3 is the same as or different from each other. The carbon number of each alkyl group of the “trialkylsilyl group” is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in the specification.

· 「Substituted or unsubstituted aralkyl group」

A specific example of the “substituted or unsubstituted aralkyl group” described in this specification is a group represented by -(G3)-(G1), where G3 is a “substituted or unsubstituted alkyl group” described in specific example group G3. and G1 is a “substituted or unsubstituted aryl group” described in specific example group G1. Therefore, an “aralkyl group” is a group in which the hydrogen atom of the “alkyl group” is replaced with an “aryl group” as a substituent, and is one aspect of a “substituted alkyl group.” “Unsubstituted aralkyl group” is an “unsubstituted aralkyl group” in which an “unsubstituted aryl group” is substituted, and the carbon number of the “unsubstituted aralkyl group” is 7 to 50, unless otherwise specified in the specification. , preferably 7 to 30, and more preferably 7 to 18.

Specific examples of “substituted or unsubstituted aralkyl group” include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenyl isopropyl group, 2-phenyl isopropyl group, phenyl-t-butyl group, and α-naph. Tylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthyl isopropyl group, 2-α-naphthyl isopropyl group, β-naphthylmethyl group, 1-β-naph Examples include thylethyl group, 2-β-naphthylethyl group, 1-β-naphthyl isopropyl group, and 2-β-naphthyl isopropyl group.

Unless otherwise stated herein, 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, triphenylene diary group, fluorenyl group, 9,9'-spirobifluorenyl group, 9,9-dimethylfluorenyl group, and 9,9-diphenylfluorenyl group.

The substituted or unsubstituted heterocyclic group described in this specification is, unless otherwise stated in this specification, preferably pyridyl group, pyrimidinyl group, triazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, and benzyl group. Imidazolyl group, phenanthrolinyl group, carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), benzocarbazolyl group , azacarbazolyl group, diazacabazolyl group, dibenzofuran group, naphthobenzofuran group, azadibenzofuran group, diazadibenzofuran group, dibenzothiophene group, naphthobenzothiophene group, azadai Benzothiophenyl 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, diphenylcarbazol-9-yl group , phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group.

In this specification, carbazolyl group is specifically any of the following groups, unless otherwise stated in this specification.

[Formula 7]

In this specification, the (9-phenyl)carbazolyl group is specifically any of the following groups, unless otherwise stated in this specification.

[Formula 8]

In the general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents the bonding position.

In this specification, dibenzofuranyl group and dibenzothiophenyl group are specifically any of the following groups, unless otherwise stated in this specification.

[Formula 9]

In the above general formulas (TEMP-34) to (TEMP-41), * represents the binding position.

Substituted or unsubstituted alkyl groups described in this specification, unless otherwise stated in this specification, are preferably methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, and t-butyl group, etc. am.

· 「Substituted or unsubstituted arylene group」

Unless otherwise specified, the “substituted or unsubstituted arylene group” described in this specification is a divalent group derived from the “substituted or unsubstituted aryl group” by removing one hydrogen atom on the aryl ring. am. Specific examples of the “substituted or unsubstituted arylene group” (specific example group G12) include 2 derived by removing one hydrogen atom on the aryl ring from the “substituted or unsubstituted aryl group” described in specific example group G1. Examples include group A, etc.

· 「Substituted or unsubstituted divalent heterocyclic group」

Unless otherwise specified, the “substituted or unsubstituted divalent heterocyclic group” described in this specification refers to a 2-valent ring derived from the “substituted or unsubstituted heterocyclic group” by removing one hydrogen atom on the heterocyclic ring. It is the spirit of Ga. As a specific example of the “substituted or unsubstituted divalent heterocyclic group” (specific example group G13), it is derived by removing one hydrogen atom on the heterocycle from the “substituted or unsubstituted heterocyclic group” described in specific example group G2. bivalent groups, etc.

· 「Substituted or unsubstituted alkylene group」

Unless otherwise specified, the “substituted or unsubstituted alkylene group” described in this specification is a divalent group derived from the “substituted or unsubstituted alkyl group” by removing one hydrogen atom on the alkyl chain. . Specific examples of the “substituted or unsubstituted alkylene group” (specific example group G14) include a divalent group derived by removing one hydrogen atom on the alkyl chain from the “substituted or unsubstituted alkyl group” described in specific example group G3. etc. can be mentioned.

Unless otherwise stated, the substituted or unsubstituted arylene group described in this specification is preferably any of the following general formulas (TEMP-42) to (TEMP-68).

[Formula 10]

[Formula 11]

In the general formulas (TEMP-42) to (TEMP-52), Q ₁ to _{Q 10} each independently represent a hydrogen atom or a substituent.

In the above general formulas (TEMP-42) to (TEMP-52), * represents the binding position.

[Formula 12]

In the general formulas (TEMP-53) to (TEMP-62), Q ₁ to _{Q 10} each independently represent a hydrogen atom or a substituent.

Formulas Q ₉ and Q ₁₀ may be bonded to each other through a single bond to form a ring.

In the general formulas (TEMP-53) to (TEMP-62), * represents the bonding position.

[Formula 13]

In the general formulas (TEMP-63) to (TEMP-68), Q ₁ to _{Q 8} each independently represent a hydrogen atom or a substituent.

In the above general formulas (TEMP-63) to (TEMP-68), * represents the binding position.

Unless otherwise stated, the substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any of the following general formulas (TEMP-69) to (TEMP-102).

[Formula 14]

[Formula 15]

[Formula 16]

In the general formulas (TEMP-69) to (TEMP-82), Q ₁ to _{Q 9} each independently represent a hydrogen atom or a substituent.

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

In the general formulas (TEMP-83) to (TEMP-102), Q ₁ to _{Q 8} each independently represent a hydrogen atom or a substituent.

The above is an explanation of “the substituents described in this specification.”

· 「When combining to form a ring」

In this specification, "one or more sets of adjacent two or more groups combine with each other to form a substituted or unsubstituted monocycle, or combine with each other to form a substituted or unsubstituted condensed ring, or combine with each other. The case of “without bonding” refers to the case where “one or more groups of two or more adjacent groups combine with each other to form a substituted or unsubstituted monocycle” and “one or more groups of two or more adjacent groups combine with each other to form a substituted or unsubstituted monocycle.” This refers to a case where “one or more groups combine with each other to form a substituted or unsubstituted condensed ring” and a case where “one or more sets of adjacent two or more groups do not combine with each other.”

In this specification, when “one or more sets of two or more adjacent groups combine with each other to form a substituted or unsubstituted monocycle,” and “one or more sets of groups consisting of two or more adjacent groups” , combining with each other to form a substituted or unsubstituted condensed ring” (hereinafter, these cases may be collectively referred to as “the case of combining to form a ring”) will be described below. The case of an anthracene compound represented by the following general formula (TEMP-103), in which the parent skeleton is an anthracene ring, will be explained as an example.

[Formula 21]

For example, among R ₉₂₁ to _{R 930} , in the case where “one or more sets of two or more adjacent groups combine with each other to form a ring,” the group consisting of two adjacent groups that constitutes one set, 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 of R ₉₂₇ and R ₉₂₈ , R ₉₂₈ and R ₉₂₉ , and R ₉₂₉ and R ₉₂₁ .

The above-mentioned “one or more sets” means that two or more sets of the adjacent two or more sets may form a ring simultaneously. For example, when R ₉₂₁ and R ₉₂₂ combine with each other to form ring Q _A , and at the same time, R ₉₂₅ and R ₉₂₆ combine with each other to form ring Q _B , represented by the general formula (TEMP-103) Anthracene compounds have the following general formula (TEMP-104): displayed.

[Formula 22]

The case where “a group consisting of two or more adjacent elements” forms a ring is not only a case where groups consisting of adjacent “two” elements are combined as in the above-mentioned example, but also a case where groups consisting of adjacent “three or more elements” are combined. Also includes cases. For example, R ₉₂₁ and R ₉₂₂ combine with each other to form ring Q _A , and R ₉₂₂ and R ₉₂₃ combine with each other to form ring Q _C , and three adjacent rings (R ₉₂₁ , R ₉₂₂ , and R ₉₂₃ ) refers to a case where groups consisting of groups combine with each other to form a ring and condense to the anthracene parent skeleton. In this case, the anthracene compound represented by the general formula (TEMP-103) has the following general formula (TEMP-105) It is displayed as . In the following general formula (TEMP-105), ring Q _A and ring Q _C share R ₉₂₂ .

[Formula 23]

The “mono-ring” or “condensed ring” formed is a structure of only the formed ring, and may be a saturated ring or an unsaturated ring. Even in the case where “one set of two adjacent groups” forms a “mono-ring” or “condensed ring”, the “mono-ring” or “condensed ring” can form a saturated ring or an unsaturated ring. there is. For example, ring Q _A and ring Q _B formed in the general formula (TEMP-104) are respectively “monocyclic” or “condensed ring.” In addition, ring Q _A and ring Q _C formed in the above general formula (TEMP-105) are “condensed rings.” Ring Q _A and ring _{Q C} of the general formula (TEMP-105) are condensed to form a condensed ring _. If ring Q _A of the general formula (TMEP-104) is a benzene ring, ring Q _A is a monocyclic ring. If ring Q _A of the general formula (TMEP-104) is a naphthalene ring, ring Q _A is a condensed ring.

“Unsaturated ring” means an aromatic hydrocarbon ring or an aromatic heterocycle. “Saturated ring” means an aliphatic hydrocarbon ring or a non-aromatic heterocycle.

Specific examples of the aromatic hydrocarbon ring include structures in which the group specified as a specific example in specific example group G1 is terminated by a hydrogen atom.

Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic group cited as a specific example in specific example group G2 is terminated by a hydrogen atom.

Specific examples of the aliphatic hydrocarbon ring include structures in which the group specified as a specific example in specific example group G6 is terminated by a hydrogen atom.

“Forming a ring” means forming a ring only with a plurality of atoms of the parent skeleton, or with a plurality of atoms of the parent skeleton and one or more arbitrary elements in addition. For example, the ring Q _A formed by R ₉₂₁ and R ₉₂₂ bonded to each other, represented by the general formula (TEMP-104), is a carbon atom of the anthracene skeleton to which R ₉₂₁ is bonded, and the anthracene skeleton to which R ₉₂₂ is bonded. It means a ring formed from a carbon atom and one or more arbitrary elements. As a specific example, in the case of forming ring Q _A with R ₉₂₁ and R ₉₂₂ , a carbon atom of the anthracene skeleton to which R ₉₂₁ is bonded, a carbon atom of the anthracene skeleton to which R ₉₂₂ is bonded, and a monocyclic unsaturated ring with 4 carbon atoms When forming a ring, the ring formed by R ₉₂₁ and R ₉₂₂ is a benzene ring.

Here, unless otherwise stated in the specification, the “arbitrary element” is preferably at least one element selected from the group consisting of a carbon element, a nitrogen element, an oxygen element, and a sulfur element. In an arbitrary element (for example, in the case of a carbon element or a nitrogen element), the bond that does not form a ring may be terminated with a hydrogen atom or the like, and may be substituted with an “optional substituent” described later. When it contains any element other than a carbon element, the ring formed is a heterocycle.

Unless otherwise stated in the specification, the “one or more arbitrary elements” constituting the monocycle or condensed ring are preferably 2 to 15 elements, more preferably 3 to 12 elements, and still more preferably Typically, there are 3 or more and 5 or less.

Unless otherwise stated in this specification, among “monocyclic” and “condensed ring”, “monocyclic” is preferable.

Unless otherwise stated in the specification, among “saturated rings” and “unsaturated rings,” “unsaturated rings” are preferable.

Unless otherwise stated in this specification, a “monocycle” is preferably a benzene ring.

Unless otherwise stated in this specification, the “unsaturated ring” is preferably a benzene ring.

In the case where “one or more groups of two or more adjacent groups” are “combined with each other to form a substituted or unsubstituted monocycle,” or when “they are combined with each other to form a substituted or unsubstituted condensed ring.” , Unless otherwise stated in the present specification, preferably, at least one set of two or more adjacent groups are bonded to each other, a plurality of atoms of the parent skeleton, and 1 to 15 carbon elements and nitrogen. It forms a substituted or unsubstituted “unsaturated ring” consisting of at least one element selected from the group consisting of an element, an oxygen element, and a sulfur element.

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

When the above-mentioned “saturated ring” 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 "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the above-mentioned section of "Substituents described in this specification."

The above is the case where “one or more sets of two or more adjacent groups combine with each other to form a substituted or unsubstituted monocycle,” and “one or more sets of groups consisting of two or more adjacent groups combine with each other.” Thus, this is an explanation of the case of “forming a substituted or unsubstituted condensed ring” (“case of forming a ring by combining”).

· Substituents in the case of “substituted or unsubstituted”

In one embodiment in the present specification, the substituent in the case of “substituted or unsubstituted” (sometimes referred to as “optional substituent” in this specification) is, for example,

Unsubstituted alkyl group having 1 to 50 carbon atoms,

An unsubstituted alkenyl group having 2 to 50 carbon atoms,

An unsubstituted alkyne 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 ),

Halogen atom, cyano group, nitro group,

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

Unsubstituted heterocyclic group having 5 to 50 ring atoms

A group selected from the group consisting of, etc.,

Here, R ₉₀₁ to R ₉₀₇ are each independently,

hydrogen atom,

A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

When two or more R _901s exist, the two or more R _901s are the same as or different from each other,

When two or more R _902s exist, the two or more R _902s are the same as or different from each other,

When two or more R ₉₀₃ exist, the two or more R ₉₀₃ are the same as or different from each other,

When two or more R _904s exist, the two or more R _904s are the same as or different from each other,

When two or more R _905s exist, the two or more R _905s are the same as or different from each other,

When two or more R _906s exist, the two or more R _906s are the same as or different from each other,

When two or more _R907s exist, the two or more _R907s are the same as or different from each other.

In one embodiment, the substituent in the case of “substituted or unsubstituted” is:

An alkyl group with 1 to 50 carbon atoms,

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

Heterocyclic group with 5 to 50 ring atoms

It is a group selected from the group consisting of.

In one embodiment, the substituent in the case of “substituted or unsubstituted” is:

An alkyl group with 1 to 18 carbon atoms,

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

Heterocyclic group with 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 specific examples of the substituents described in the above section “Substituents described in this specification.”

In this specification, unless otherwise stated, any adjacent substituents may form a “saturated ring” or an “unsaturated ring”, and are preferably a substituted or unsubstituted saturated 5-membered ring, or a substituted ring. Alternatively, it forms an unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, and more preferably forms a benzene ring.

In this specification, unless otherwise stated, any substituent may further have a substituent. The substituents that any substituent further has are the same as the above-mentioned arbitrary substituents.

In this specification, the numerical range expressed using “AA to BB” is set with the numerical value AA written before “AA to BB” as the lower limit, and the numerical value BB written after “AA to BB” as the upper limit. It means the inclusive range.

Hereinafter, the compounds of the present invention will be described.

The compound according to one aspect of the present invention has the following formula (1): displayed.

However, hereinafter, the compound of the present invention expressed by formula (1) and the formula included in formula (1) described later may be simply referred to as “invention compound (1).” In addition, the compound according to another aspect of the present invention is represented by formula (2) described later. Hereinafter, the compound of the present invention expressed by formula (2) described later and the formula included in formula (2) described later may be simply referred to as “invention compound (2).” Additionally, when both "invention compound (1)" and "invention compound (2)" are meant, they may simply be referred to as "invention compound".

[Formula 24]

Hereinafter, symbols in equations included in equation (1) and equation (1) described later will be explained. Meanwhile, identical symbols have identical meanings.

In equation (1),

Ar ¹ to ^{Ar 3} each independently represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

The details of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms represented by Ar ¹ to ^{Ar 3} are as described above in the section “Substituents described in this specification.”

The unsubstituted aryl group represented by Ar ¹ to ^{Ar 3} is preferably a phenyl group, biphenyl group, naphthyl group, or fluorenyl group.

Details of the substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms represented by Ar ¹ to ^{Ar 3} are as described above in the section “Substituents described in this specification.”

The unsubstituted heterocyclic group represented by Ar ¹ to ^{Ar 3} is preferably a pyridyl group, quinazolinyl group, dibenzofuranyl group, or dibenzothiophenyl group.

Ar ¹ is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, more preferably a phenyl group, biphenyl group, or naphthyl group, and still more preferably a phenyl group.

In one embodiment, Ar ² is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, more preferably a phenyl group, biphenyl group, naphthyl group, or fluorenyl group, and even more preferably an aryl group having 6 to 30 ring carbon atoms. It is a phenyl group, a biphenyl group, or a naphthyl group.

In another aspect, Ar ² is preferably a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, and more preferably a pyridyl group, quinazolinyl group, dibenzofuranyl group, or dibenzothiophene. It's a diary.

Ar ³ is preferably a phenyl group, pyridyl group, dibenzofuranyl group, or dibenzothiophenyl group, and more preferably a dibenzofuranyl group.

L ¹ is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, and Ar ² and L ¹ are bonded to each other to form a substituted or unsubstituted arylene group. An unsubstituted ring may be formed.

L ¹ is preferably a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms.

The details of the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms represented by L ¹ are as described above in the section “Substituents described in this specification.”

The unsubstituted arylene group having 6 to 30 ring carbon atoms represented by L ¹ is preferably a phenylene group, biphenylene group, or naphthylene group, and more preferably a phenylene group.

The details of the substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms represented by L ¹ are as described above in the section “Substituents described in this specification.”

The details of the optional substituted or unsubstituted ring formed by combining Ar ² and L ¹ are as described above in “Substituents described in this specification,” and include a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted ring, It is selected from an aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocycle, and a substituted or unsubstituted non-aromatic heterocycle.

The aromatic hydrocarbon ring is, for example, a benzene ring, a biphenylene ring, a naphthalene ring, or a fluorene ring, and is preferably a naphthalene ring or a fluorene ring.

The aliphatic hydrocarbon ring is, for example, a cyclopentene ring, a cyclopentadiene ring, a cyclohexene ring, a cyclohexadiene ring, or a hydrocarbon ring obtained by partially hydrogenating the aromatic hydrocarbon ring.

The aromatic heterocycle includes, for example, pyrrole ring, furan ring, thiophene ring, pyridine ring, imidazole ring, pyrazole ring, indole ring, isoindole ring, benzofuran ring, isobenzofuran ring, benzothiophene ring, benzimidazole ring, indazole ring, dibenzofuran ring, naphthobenzofuran ring, dibenzothiophene ring, naphthobenzothiophene ring, carbazole ring, or benzocarbazole ring, preferably dibenzofuran ring, or It is a dibenzothiophene pill.

The non-aromatic heterocycle is, for example, a heterocycle obtained by partially hydrogenating the aromatic heterocycle.

L ² is a single bond or a 2+p-valent residue of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 25 ring carbon atoms.

In one aspect of the present invention, L ² is preferably a single bond. In another aspect, L ² is preferably a 2+p-valent residue of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 25 ring carbon atoms.

Examples of the 2+p-valent residue of the substituted or unsubstituted aromatic hydrocarbon ring having 6 to 25 ring carbon atoms represented by L ² include, for example, phenylene group, biphenylylene group, terphenylylene group, naphthylene group, and anthryl. Renal group, benzantrylene group, phenanthrylene group, benzophenanthrylene group, phenaleneylene group, picenylene group, pentaphenylene group, pyreneylene group, chrysenylene group, benzochrysenylene group, triphenyleneylene group, fluoranthenylene group , or a fluorenylene group.

The 2+p-valent residue of the unsubstituted aromatic hydrocarbon ring having 6 to 25 ring carbon atoms represented by L ² is preferably a phenylene group, biphenylene group, or naphthylene group, and more preferably a phenylene group.

p is 0 or 1, when L ² is a single bond, p is 0, and when L ² is a 2+p valent residue of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 25 ring carbon atoms, p is 0. or 1.

p is preferably 0.

R ¹ to R ⁶ and R ¹¹ to ^{R 14} are each independently,

hydrogen atom,

halogen Atom,

Cyanogi,

nitrogi,

A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

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 group represented by Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

A group represented by -O-(R ₉₀₄ ),

A group represented by -S-(R ₉₀₅ ),

A group represented by -N(R ₉₀₆ )(R ₉₀₇ ),

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

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

R ₉₀₁ to R ₉₀₇ are each independently,

hydrogen atom,

A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

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

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

When two or more R _901s exist, the two or more R _901s are the same as or different from each other,

When two or more R _902s exist, the two or more R _902s are the same as or different from each other,

When two or more R ₉₀₃ exist, the two or more R ₉₀₃ are the same as or different from each other,

When two or more R _904s exist, the two or more R _904s are the same as or different from each other,

When two or more R _905s exist, the two or more R _905s are the same as or different from each other,

When two or more R _906s exist, the two or more R _906s are the same as or different from each other,

When two or more R _907s exist, the two or more R _907s are the same or different from each other,

R ¹ and R ² do not combine with each other to form a ring,

In one or more groups selected from R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ¹¹ and R ¹² , R ¹² and R ¹³ , and R ¹³ and R ¹⁴ , two adjacent ones are bonded to each other Thus, a substituted or unsubstituted ring may be formed.

R ¹ to R ⁶ and R ¹¹ to ^{R 14} are each independently, preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms. , a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, more preferably a hydrogen atom or a substituted or unsubstituted heterocyclic group having 1 to 50 ring carbon atoms. It is an alkyl group, and more preferably, it is a hydrogen atom.

The details of the halogen atoms represented by R ¹ to R ⁶ and R ¹¹ to ^{R 14} are as described above in the section “Substituents described in this specification,” and are preferably fluorine atoms.

The details of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms represented by R ¹ to R ⁶ and R ¹¹ to ^{R 14} are as described above in the section “Substituents described in this specification.”

The unsubstituted alkyl group represented by R ¹ to R ⁶ and R ¹¹ to ^{R 14} is preferably a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, and s-butyl group. , or a t-butyl group, more preferably a methyl group, an ethyl group, an isopropyl group, or a t-butyl group, and even more preferably a methyl group or a t-butyl group.

The details of the substituted or unsubstituted alkenyl group having 2 to 50 ring carbon atoms represented by R ¹ to R ⁶ and R ¹¹ to ^{R 14} are as described above in the section “Substituents described in this specification.”

Details of the substituted or unsubstituted alkynyl group having 2 to 50 ring carbon atoms represented by R ¹ to R ⁶ and R ¹¹ to ^{R 14} are as described above in the section “Substituents described in this specification.”

Details of the substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms represented by R ¹ to R ⁶ and R ¹¹ to ^{R 14} are as described above in the section “Substituents described in this specification.”

The unsubstituted cycloalkyl group represented by R ¹ to R ⁶ and R ¹¹ to ^{R 14} is preferably cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-ah. It is a damantyl group, 1-norbornyl group, or 2-norbornyl group, more preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and even more preferably a cyclopentyl group or a cyclohexyl group.

R ¹ to R ⁶ , and R ¹¹ to ^{R 14} , -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ), -O-(R ₉₀₄ ), -S-(R ₉₀₅ ); The details of the group represented by and -N(R ₉₀₆ )(R ₉₀₇ ) are as described in “Substituents described in this specification.”

The details of the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms represented by R ¹ to ^{R 6} and R ¹¹ to ^{R 14} are as described in “Substituents described in this specification.”

The unsubstituted aryl group represented by R ¹ to R ⁶ and R ¹¹ to ^{R 14} is preferably a phenyl group, a biphenyl group, a naphthyl group, or a phenanthryl group, and more preferably a phenyl group, a biphenyl group, or a naphthyl group. And, more preferably, it is a phenyl group.

Details of the substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms represented by R ¹ to R ⁶ and R ¹¹ to ^{R 14} are as described in “Substituents described in this specification.”

The unsubstituted heterocyclic group is preferably a dibenzofuranyl group or a dibenzothiophenyl group.

In one or more groups selected from R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ¹¹ and R ¹² , R ¹² and R ¹³ , and R ¹³ and R ¹⁴ , two adjacent ones are bonded to each other The details of the optionally substituted or unsubstituted ring formed by this are the same as the details described above regarding the optionally substituted or unsubstituted ring formed by combining Ar ² and L ¹ with each other.

In the present invention, in one or more groups selected from R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ¹¹ and R ¹² , R ¹² and R ¹³ , and R ¹³ and R ¹⁴ , adjacent The two do not have to combine with each other to form a substituted or unsubstituted ring.

X ¹ is an oxygen atom or a sulfur atom.

In one aspect of the present invention, X ¹ is preferably an oxygen atom. In another aspect, X ¹ is preferably a sulfur atom.

*d is bonded to one carbon atom selected from *a, *b, and *c.

In one aspect of the present invention, *d is preferably bonded to the carbon atom *a. In another aspect, *d is preferably bonded to the carbon atom *b. In another aspect, *d is preferably bonded to the carbon atom *c.

The invention compound (1) represented by formula (1) is preferably one of the following formulas (1A) to (1C): displayed.

[Formula 25]

In formulas (1A) to (1C),

R ²¹ to R ²⁵ and R ³¹ to ^{R 38} are each independently,

hydrogen atom,

halogen Atom,

Cyanogi,

nitrogi,

A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

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 group represented by Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

A group represented by -O-(R ₉₀₄ ),

A group represented by -S-(R ₉₀₅ ),

A group represented by -N(R ₉₀₆ )(R ₉₀₇ ),

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

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

step,

In equation (1A),

When p is 0, one selected from R ²¹ to R ²⁵ is a single bond bonded to *f,

When p is 1, one selected from R ²¹ to ^{R 25} is a single bond bonded to *e, and the other bond selected from R ²¹ to R ²⁵ is a single bond bonded to *f,

In equation (1B),

When p is 0, one selected from R ³¹ to ^{R 38} is a single bond bonded to *g, and the other bond selected from R ³¹ to R ³⁸ is a single bond bonded to *i,

When p is 1, one selected from R ³¹ to ^{R 38} is a single bond bonded to *g, the other bond selected from R ³¹ to R ³⁸ is a single bond bonded to *h, and R ³¹ to Another one selected from R ³⁸ is a single bond bonded to *i.

Ar ¹ ∼Ar ³ , L ¹ , p ^, R ¹ ∼R ⁶ _, ^{R 11} ∼R ₁₄ , It is as defined.

R ²¹ to R ²⁵ and R ³¹ to ^{R 38} are each independently, preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms. , a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, more preferably a hydrogen atom, a substituted or unsubstituted aryl group having 1 to 50 ring carbon atoms. an alkyl group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, more preferably a hydrogen atom or a substituted or unsubstituted ring forming group. It is an aryl group having 6 to 50 carbon atoms, and more preferably a hydrogen atom.

The details of each group represented by R ²¹ to ^{R 25} and R ³¹ to ^{R 38} are the same as those of the corresponding groups described for R ¹ to ^{R 6} and R ¹¹ to ^{R 14} , and the preferred groups are all the same. do.

In equation (1A),

When p is 0, one selected from R ²² to R ²⁴ is preferably a single bond bonded to *f.

When p is 1, it is preferable that one selected from R ²² and R ²³ is a single bond bonded to *e, and one selected from R ²⁴ and R ²⁵ is a single bond bonded to *f.

The invention compound (1) represented by formula (1) is preferably represented by the following formula (1A-1) or (1B-1): displayed.

[Formula 26]

In formulas (1A-1) and (1B-1),

Ar ¹ , Ar ² , L ¹ , R ¹ to R ⁶ , R ¹¹ to R ¹⁴ , X ¹ , *a, *b, *c, and *d are as defined in formula (1), and R ²¹ to R ²⁶ , and *f are as defined in Formula (1A), and R ³¹ to R ³⁸ , *g, and *i are as defined in Formula (1B).

The invention compound (1) represented by formula (1) is preferably represented by the following formula (1A-1a) or (1A-1b): displayed.

[Formula 27]

In formulas (1A-1a) and (1A-1b),

Ar ¹ , Ar ² , L ¹ , R ¹ to R ⁶ , R ¹¹ to R ¹⁴ , X ¹ , *a, *b, *c, and *d are as defined in formula (1), and R ²¹ to R ²⁵ is as defined in equation (1A).

Inventive compound (1) represented by formula (1) is preferably represented by the following formula (1A-1c) displayed.

[Formula 28]

In formula (1A-1c),

Ar ¹ , Ar ² , L ¹ , R ¹ to R ⁶ , R ¹¹ to R ¹⁴ , and X ¹ are as defined in formula (1), and R ²¹ to ^{R 25} and *f are as defined in formula (1A). It is as defined.

Inventive compound (1) represented by formula (1) is preferably represented by the following formula (1C-1a) displayed.

[Formula 29]

In formula (1C-1a),

Ar ¹ , Ar ² , L ¹ , R ¹ to R ⁶ , R ¹¹ to R ¹⁴ , and X ¹ are as defined in formula (1).

As one aspect of the present invention,

(1-1) R ¹ to R ⁶ may be a hydrogen atom,

(1-2) R ¹¹ to R ¹⁴ may all be hydrogen atoms,

(1-3) In formula (1A), R ²¹ to ^{R 25} that are not single bonds bonding to *f and *e may all be hydrogen atoms,

(1-4) In formula (1B), R ³¹ to ^{R 38} that are not single bonds bonding to *g, *h and *i may all be hydrogen atoms,

(1-5) In formula (1A-1), R ²¹ to ^{R 25} that are not a single bond bonded to *f may all be hydrogen atoms,

(1-6) In formula (1B-1), R ³¹ to ^{R 38} that are not single bonds bonding to *g and *i may all be hydrogen atoms,

(1-7) In formula (1A-1a), R ²¹ , R ²² , R ²⁴ and R ²⁵ may all be hydrogen atoms,

(1-8) In formula (1A-1b), R ²¹ and R ²³ to ^{R 25} may all be hydrogen atoms,

(1-9) In formula (1A-1c), R ²¹ to ^{R 25} that are not a single bond bonded to *f may all be hydrogen atoms.

Compounds according to another aspect of the present invention have the following formula (2): displayed.

[Formula 30]

Hereinafter, symbols in equations included in equation (2) and equation (2) described later will be explained. Meanwhile, identical symbols have identical meanings.

In equation (2),

Ar ¹¹ to ^{Ar 13} each independently represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

The details of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms represented by Ar ¹¹ to ^{Ar 13} are as described above in the section “Substituents described in this specification.”

The unsubstituted aryl group represented by Ar ¹¹ to ^{Ar 13} is preferably a phenyl group, biphenyl group, naphthyl group, or fluorenyl group.

Details of the substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms represented by Ar ¹¹ to ^{Ar 13} are as described above in the section “Substituents described in this specification.”

The unsubstituted heterocyclic group represented by Ar ¹¹ to ^{Ar 13} is preferably a pyridyl group, quinazolinyl group, dibenzofuranyl group, or dibenzothiophenyl group.

Ar ¹¹ is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, more preferably a phenyl group, biphenyl group, or naphthyl group, and still more preferably a phenyl group.

In one embodiment, Ar ¹² is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, more preferably a phenyl group, biphenyl group, naphthyl group, or fluorenyl group, and even more preferably an aryl group having 6 to 30 ring carbon atoms. It is a phenyl group, a biphenyl group, or a naphthyl group.

In another aspect, Ar ¹² is preferably a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, and more preferably a pyridyl group, quinazolinyl group, dibenzofuranyl group, or dibenzothiophene. It's a diary.

Ar ¹³ is preferably a phenyl group, a pyridyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, and more preferably a dibenzofuranyl group.

L ¹¹ is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, and Ar ¹² and L ¹¹ are bonded to each other to form a substituted or unsubstituted arylene group. An unsubstituted ring may be formed.

L ¹¹ is preferably a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms.

The details of the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms represented by L ¹¹ are as described above in the section “Substituents described in this specification.”

The unsubstituted arylene group having 6 to 30 ring carbon atoms represented by L ¹¹ is preferably a phenylene group, biphenylene group, or naphthylene group, and more preferably a phenylene group.

The details of the substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms represented by L ¹¹ are as described above in the section “Substituents described in this specification.”

The details of the optional substituted or unsubstituted ring formed by combining Ar ¹² and L ¹¹ are as described above in “Substituents described in this specification,” and include a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted ring, and a substituted or unsubstituted ring. It is selected from an aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocycle, and a substituted or unsubstituted non-aromatic heterocycle. Details of the substituted or unsubstituted aromatic hydrocarbon ring, the substituted or unsubstituted aliphatic hydrocarbon ring, the substituted or unsubstituted aromatic heterocycle, and the substituted or unsubstituted non-aromatic heterocycle are given in Formula (1): Ar The details are the same as when ² and L ¹ combine with each other to form a substituted or unsubstituted ring.

L ¹² is a 2+q valent residue of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 25 ring carbon atoms.

Examples of the 2+q-valent residue of the substituted or unsubstituted aromatic hydrocarbon ring having 6 to 25 ring carbon atoms represented by L ¹² include, for example, phenylene group, biphenylylene group, terphenylylene group, naphthylene group, and anthryl. Renal group, benzantrylene group, phenanthrylene group, benzophenanthrylene group, phenaleneylene group, piceneylene group, pentaphenylene group, pyreneylene group, chrysenylene group, benzochrysenylene group, triphenyleneylene group, fluoranthenylene group , or a fluorenylene group.

The 2+q-valent residue of the unsubstituted aromatic hydrocarbon ring having 6 to 25 ring carbon atoms represented by L ¹² is preferably a phenylene group, biphenylene group, or naphthylene group, and more preferably a phenylene group.

q is 0 or 1.

q is preferably 0.

R ⁴¹ to R ⁴⁶ and R ⁵¹ to ^{R 54} are each independently,

hydrogen atom,

halogen Atom,

Cyanogi,

nitrogi,

A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

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 group represented by Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

A group represented by -O-(R ₉₀₄ ),

A group represented by -S-(R ₉₀₅ ),

A group represented by -N(R ₉₀₆ )(R ₉₀₇ ),

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

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

R ₉₀₁ to R ₉₀₇ are each independently,

hydrogen atom,

A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

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

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

When two or more R _901s exist, the two or more R _901s are the same as or different from each other,

When two or more R _902s exist, the two or more R _902s are the same as or different from each other,

When two or more R ₉₀₃ exist, the two or more R ₉₀₃ are the same as or different from each other,

When two or more R _904s exist, the two or more R _904s are the same as or different from each other,

When two or more R _905s exist, the two or more R _905s are the same as or different from each other,

When two or more R _906s exist, the two or more R _906s are the same as or different from each other,

When two or more R _907s exist, the two or more R _907s are the same or different from each other,

R ⁴¹ and R ⁴² do not combine with each other to form a ring,

In one or more groups selected from R ⁴³ and R ⁴⁴ , R ⁴⁴ and R ⁴⁵ , R ⁴⁵ and R ⁴⁶ , R ⁵¹ and R ⁵² , R ⁵² and R ⁵³ , and R ⁵³ and R ⁵⁴ , two adjacent ones are bonded to each other Thus, a substituted or unsubstituted ring may be formed.

The details of each group represented by R ⁴¹ to ^{R 46} and R ⁵¹ to ^{R 54} are the same as those of the corresponding groups described for R ¹ to ^{R 6} and R ¹¹ to ^{R 14} , and the preferred groups are all the same. do.

In one or more groups selected from R ⁴³ and R ⁴⁴ , R ⁴⁴ and R ⁴⁵ , R ⁴⁵ and R ⁴⁶ , R ⁵¹ and R ⁵² , R ⁵² and R ⁵³ , and R ⁵³ and R ⁵⁴ , two adjacent ones are bonded to each other The details of the optional substituted or unsubstituted ring formed are as described above in “Substituents described in this specification”, and include a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic hydrocarbon ring, and a substituted or unsubstituted ring. It is selected from aromatic heterocycles and substituted or unsubstituted non-aromatic heterocycles. Details of the substituted or unsubstituted aromatic hydrocarbon ring, the substituted or unsubstituted aliphatic hydrocarbon ring, the substituted or unsubstituted aromatic heterocycle, and the substituted or unsubstituted non-aromatic heterocycle are given in Formula (1): Ar The details are the same as when ² and L ¹ combine with each other to form a substituted or unsubstituted ring.

In the present invention, in one or more groups selected from R ⁴³ and R ⁴⁴ , R ⁴⁴ and R ⁴⁵ , R ⁴⁵ and R ⁴⁶ , R ⁵¹ and R ⁵² , R ⁵² and R ⁵³ , and R ⁵³ and R ⁵⁴ , adjacent The two do not have to combine with each other to form a substituted or unsubstituted ring.

X ¹¹ is an oxygen atom or a sulfur atom.

In one aspect of the present invention, X ¹¹ is preferably an oxygen atom. In another aspect, X ¹¹ is preferably a sulfur atom.

The invention compound (2) represented by formula (2) is preferably represented by the following formula (2A) or (2B): displayed.

[Formula 31]

In equations (2A) and (2B),

R ⁶¹ to R ⁶⁵ and R ⁷¹ to ^{R 78} are each independently,

hydrogen atom,

halogen Atom,

Cyanogi,

nitrogi,

A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

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 group represented by Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

A group represented by -O-(R ₉₀₄ ),

A group represented by -S-(R ₉₀₅ ),

A group represented by -N(R ₉₀₆ )(R ₉₀₇ ),

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

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

step,

In equation (2A),

When q is 0, the other one selected from R ⁶¹ to R ⁶⁵ is a single bond bonded to *k,

When q is 1, one selected from R ⁶¹ to ^{R 65} is a single bond bonded to *j, and the other selected from R ⁶¹ to R ⁶⁵ is a single bond bonded to *k,

In equation (2B),

When q is 0, one selected from R ⁷¹ to R ⁷⁸ is a single bond bonded to *l, and the other bond selected from R ⁷¹ to R ⁷⁸ is a single bond bonded to *m,

When q is 1, one selected from R ⁷¹ to R ⁷⁸ is a single bond bonded to *l, the other bond selected from R ⁷¹ to R ⁷⁸ is a single bond bonded to *j, and R ⁷¹ to Another one selected from R ⁷⁸ is a single bond bonded to *m.

Ar ¹¹ to Ar ¹³ , L ¹¹ , q, R ⁴¹ to R ⁴⁶ , R ⁵¹ to R ⁵⁴ , X ¹¹ , and R ₉₀₁ to R ₉₀₇ are as defined in formula (2).

R ⁶¹ to R ⁶⁵ and R ⁷¹ to ^{R 78} are each independently, preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms. , a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, more preferably a hydrogen atom, a substituted or unsubstituted aryl group having 1 to 50 ring carbon atoms. an alkyl group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, more preferably a hydrogen atom or a substituted or unsubstituted ring forming group. It is an aryl group having 6 to 50 carbon atoms, and more preferably a hydrogen atom.

The details of each group represented by R ⁶¹ to ^{R 65} and R ⁷¹ to ^{R 78} are the same as those of the corresponding groups described for R ¹ to ^{R 6} and R ¹¹ to ^{R 14} , and all preferred groups are the same. do.

In equation (2A),

When q is 0, one selected from R ⁶² to R ⁶⁴ is preferably a single bond bonded to *k.

When q is 1, it is preferable that one selected from R ⁶² and R ⁶³ is a single bond bonded to *k, and one selected from R ⁶⁴ and R ⁶⁵ is a single bond bonded to *j.

The invention compound (2) represented by formula (2) is preferably represented by the following formula (2A-1) or (2B-1): displayed.

[Formula 32]

In formulas (2A-1) and (2B-1),

Ar ¹¹ and Ar ¹² , L ¹¹ , R ⁴¹ to R ⁴⁶ , R ⁵¹ to R ⁵⁴ , and X ¹¹ are as defined in formula (2), and R ⁶¹ to ^{R 65} and *k are as defined in formula (2A) It is as defined, and R ⁷¹ to R ⁷⁸ , *l, and *n are as defined in formula (2B).

The invention compound (2) represented by formula (2) is preferably represented by the following formula (2A-1a) or (2B-1b): displayed.

[Formula 33]

In formulas (2A-1a) and (2B-1b),

Ar ¹¹ and Ar ¹³ , L ¹¹ , R ⁴¹ to R ⁴⁶ , R ⁵¹ to ^{R 54} , and X ¹¹ are as defined in Formula (2), and R ⁶¹ to ^{R 66} are as defined in Formula (2A).

As one aspect of the present invention,

(2-1) R ⁴¹ to R ⁴⁶ may be hydrogen atoms,

(2-2) R ⁵¹ to R ⁵⁴ may all be hydrogen atoms,

(2-3) In formula (2A), R ⁶¹ to ^{R 65} that are not single bonds bonding to *j and *k may all be hydrogen atoms,

(2-4) In formula (2B), R ⁷¹ to ^{R 78} that are not single bonds bonding to *l, *m and *n may all be hydrogen atoms,

(2-5) In formula (2A-1), R ⁶¹ to ^{R 65} that are not a single bond bonded to *j may all be hydrogen atoms,

(2-6) In formula (2B-1), R ⁷¹ to ^{R 78} that are not single bonds bonding to *k and *l may all be hydrogen atoms,

(2-7) In formula (2A-1a), R ⁶¹ , R ⁶² , R ⁶⁴ and R ⁶⁵ may all be hydrogen atoms,

(2-8) In formula (2A-1b), R ⁶¹ and R ⁶³ to ^{R 65} may all be hydrogen atoms.

As mentioned above, the “hydrogen atom” used in this specification includes light hydrogen atoms, heavy hydrogen atoms, and tritium atoms. Therefore, the inventive compound may contain naturally occurring deuterium atoms.

Additionally, a deuterium atom may be intentionally introduced into the invention compound by using a compound in which part or all of the raw material compound is deuterated. Accordingly, in one aspect of the present invention, the inventive compound contains at least one deuterium atom. That is, invention compound (1) is a compound represented by formula (1), and may be a compound in which at least one hydrogen atom contained in the compound is a deuterium atom, and invention compound (2) is expressed by formula (2). The compound may be a compound in which at least one hydrogen atom contained in the compound is a deuterium atom.

In the compound represented by formula (1),

A hydrogen atom possessed by a substituted or unsubstituted aryl group or heterocyclic group represented by any of Ar ¹ to Ar ³ ;

A hydrogen atom possessed by the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or the divalent heterocyclic group represented by L ¹ ;

A hydrogen atom possessed by the 2+p-valent residue of the substituted or unsubstituted aromatic hydrocarbon ring having 6 to 25 ring carbon atoms represented by L ² ;

a hydrogen atom represented by any of R ¹ to R ⁶ and R ¹¹ to R ¹⁴ ; A hydrogen atom possessed by a substituted or unsubstituted alkyl group, alkenyl group, alkynyl group, cycloalkyl group, aryl group, or heterocyclic group represented by any of R ¹ to R ⁶ and R ¹¹ to ^{R 14} ; A group represented by -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ), a group represented by -O-(R ₉₀₄ ), -S- represented by any of R ¹ to R ⁶ and R ¹¹ to ^{R 14} a hydrogen atom possessed by a group represented by (R ₉₀₅ ), a group represented by -N(R ₉₀₆ )(R ₉₀₇ );

A hydrogen atom represented by any of R ₉₀₁ to R ₉₀₇ ; A hydrogen atom possessed by a substituted or unsubstituted alkyl group, cycloalkyl group, aryl group, or heterocyclic group represented by any of R ₉₀₁ to _{R 907} ;

A hydrogen atom possessed by the pyrimidine ring constituting formula (1);

Hydrogen atoms other than R ¹¹ to R ¹⁴ included in the structure represented by the following formula (1-x) constituting formula (1);

At least one hydrogen atom selected from may be a deuterium atom.

[Formula 34]

However, in formula (1-x), * is the bonding position to L ² , and R ¹¹ to R ¹⁴ , X ¹ , *a, *b, *c, and *d are as defined in formula (1).

In the compound represented by formula (2),

A hydrogen atom possessed by a substituted or unsubstituted aryl group or heterocyclic group represented by any of Ar ¹¹ to Ar ¹³ ;

A hydrogen atom possessed by the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or the divalent heterocyclic group represented by L ¹¹ ;

A hydrogen atom possessed by the 2+q valent residue of the substituted or unsubstituted aromatic hydrocarbon ring having 6 to 25 ring carbon atoms represented by L ¹² ;

A hydrogen atom represented by any of R ⁴¹ to R ⁴⁶ and R ⁵¹ to R ⁵⁴ ; A hydrogen atom possessed by a substituted or unsubstituted alkyl group, alkenyl group, alkynyl group, cycloalkyl group, aryl group, or heterocyclic group represented by any of R ⁴¹ to R ⁴⁶ and R ⁵¹ to ^{R 54} ; A group represented by -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ), a group represented by -O-(R ₉₀₄ ), -S- represented by any of R ⁴¹ to R ⁴⁶ and R ⁵¹ to R ⁵⁴ a hydrogen atom possessed by a group represented by (R ₉₀₅ ), a group represented by -N(R ₉₀₆ )(R ₉₀₇ );

A hydrogen atom represented by any of R ₉₀₁ to R ₉₀₇ ; A hydrogen atom possessed by a substituted or unsubstituted alkyl group, cycloalkyl group, aryl group, or heterocyclic group represented by any of R ₉₀₁ to _{R 907} ;

A hydrogen atom possessed by the pyrimidine ring constituting formula (2);

Hydrogen atoms other than R ⁵¹ to R ⁵⁴ contained in the structure represented by the following formula (2-x) constituting formula (2);

At least one hydrogen atom selected from may be a deuterium atom.

[Formula 35]

However, in formula (2-x), 14 is the binding position to L ¹² , R ⁵¹ to R ⁵⁴ , and X ¹² are as defined in formula (2).

The deuteration rate of the inventive compound depends on the deuteration rate of the raw material compound used. Even if raw materials with a predetermined deuterium digestion rate are used, light hydrogen isotopes of natural origin may be included in a certain ratio. Therefore, the mode of deuteration rate of the invention compound shown below includes a ratio that takes into account trace amounts of naturally occurring isotopes to the ratio obtained by simply counting the number of deuterium atoms expressed in the chemical formula.

The deuteration rate of the invention compound is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, even more preferably 10% or more, and even more preferably 50% or more.

The invention compound may be a mixture containing a deuterated compound and a non-deuterated compound, or a mixture of two or more compounds having different deuteration rates. The deuteration rate of such a mixture is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, even more preferably 10% or more, even more preferably 50% or more, and It is less than 100%.

In addition, the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the invention compound is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, and even more preferably 10%. or more, and also less than 100%.

The details of the substituents (optional substituents) in the case of “substituted or unsubstituted” included in the definition of each formula above are as described in “Substituents in the case of “substituted or unsubstituted”” am.

The inventive compound can be easily produced by those skilled in the art by referring to the synthesis examples and known synthesis methods described later.

Specific examples of the invention compounds are shown below, but are not limited to the following exemplary compounds.

In the following specific examples, D represents a deuterium atom.

[Formula 36]

[Formula 37]

[Formula 38]

[Formula 39]

[Formula 40]

[Formula 41]

[Formula 42]

[Formula 43]

[Formula 44]

[Formula 45]

[Formula 46]

[Formula 47]

[Formula 48]

[Formula 49]

[Formula 50]

[Formula 51]

[Formula 52]

[Formula 53]

[Formula 54]

[Formula 55]

[Formula 56]

[Formula 57]

[Formula 58]

[Formula 59]

[Formula 60]

[Formula 61]

[Formula 62]

[Formula 63]

[Formula 64]

[Formula 65]

[Formula 66]

[Formula 67]

[Formula 68]

[Formula 69]

[Formula 70]

[Formula 71]

[Formula 72]

[Formula 73]

[Formula 74]

[Formula 75]

[Formula 76]

[Formula 77]

[Formula 78]

[Formula 79]

[Formula 80]

[Formula 81]

[Formula 82]

[Formula 83]

[Formula 84]

[Formula 85]

[Formula 86]

[Formula 87]

[Formula 88]

[Formula 89]

[Formula 90]

[Formula 91]

[Formula 92]

[Formula 93]

[Formula 94]

[Formula 95]

[Formula 96]

[Formula 97]

Materials for organic EL devices

The material for an organic EL device of the present invention contains the inventive compound. The content of the invention compound in the organic EL device material is preferably 1% by mass or more (inclusive of 100%), preferably 10% by mass or more (inclusive of 100%), and 50% by mass or more (inclusive of 100%). It is more preferable that it is 80 mass% or more (inclusive of 100%), and it is especially preferable that it is 90 mass% or more (inclusive of 100%). The material for organic EL devices of the present invention is useful for manufacturing organic EL devices.

Organic EL device

The organic EL device of the present invention includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer contains a light-emitting layer, and at least one layer of the organic layer contains the invention compound.

Examples of the organic layer containing the invention compound include a hole transport zone (hole injection layer, hole transport layer, electron blocking layer, exciton blocking layer, etc.) provided between the anode and the light-emitting layer, a light-emitting layer, a space layer, and an electron layer provided between the cathode and the light-emitting layer. Transport bands (electron injection layer, electron transport layer, hole blocking layer, etc.) may be mentioned, but are not limited to these. The invention compound is preferably a material of the electron transport band of a fluorescent or phosphorescent EL device, more preferably a material of an electron transport layer or a hole blocking layer, particularly preferably a first electron transport layer, a second electron transport layer, or a hole device layer. It is used as a material for

The organic EL device of the present invention may be a fluorescent or phosphorescent monochromatic light emitting device, a fluorescent/phosphorescent hybrid white light emitting device, a simple type having a single light emitting unit, or a tandem type having a plurality of light emitting units. , Among these, it is preferable that it is a fluorescence-emitting type device. Here, the “light-emitting unit” refers to the minimum unit that includes an organic layer, at least one layer of which is a light-emitting layer, and emits light when injected holes and electrons recombine.

For example, a typical element configuration of a simple type organic EL device includes the following device configuration.

(1) Anode/light emitting unit/cathode

Additionally, the light emitting unit may be of a multilayer type having a plurality of phosphorescent light emitting layers or a plurality of fluorescent light emitting layers. In that case, a space layer may be provided between each light emitting layer for the purpose of preventing excitons generated in the phosphorescent light emitting layer from diffusing into the fluorescent light emitting layer. do. A typical layer structure of a simple type light emitting unit is shown below. The layers in parentheses are arbitrary.

(a) (hole injection layer/)hole transport layer/fluorescence emitting layer/electron transport layer (/electron injection layer)

(b) (hole injection layer/)hole transport layer/phosphorescent emitting layer/electron transport layer (/electron injection layer)

(c) (hole injection layer/) hole transport layer/first fluorescent emitting layer/second fluorescent emitting layer/electron transport layer (/electron injection layer)

(d) (hole injection layer/) hole transport layer/first phosphorescent emitting layer/second phosphorescent emitting layer/electron transport layer (/electron injection layer)

(e) (hole injection layer/)hole transport layer/phosphorescent light-emitting layer/space layer/fluorescent light-emitting layer/electron transport layer (/electron injection layer)

(f) (hole injection layer/) hole transport layer/first phosphorescent emitting layer/second phosphorescent emitting layer/space layer/fluorescent emitting layer/electron transport layer (/electron injection layer)

(g) (hole injection layer/) hole transport layer/first phosphorescent emitting layer/space layer/second phosphorescent emitting layer/space layer/fluorescent emitting layer/electron transport layer (/electron injection layer)

(h) (hole injection layer/) hole transport layer/phosphorescent emitting layer/space layer/first fluorescent emitting layer/second fluorescent emitting layer/electron transport layer (/electron injection layer)

(i) (hole injection layer/)hole transport layer/electron blocking layer/fluorescence emitting layer/electron transport layer (/electron injection layer)

(j) (hole injection layer/)hole transport layer/electron blocking layer/phosphorescent emitting layer/electron transport layer (/electron injection layer)

(k) (hole injection layer/)hole transport layer/exciton blocking layer/fluorescence emitting layer/electron transport layer (/electron injection layer)

(l) (hole injection layer/)hole transport layer/exciton blocking layer/phosphorescence emitting layer/electron transport layer (/electron injection layer)

(m) (hole injection layer/) first hole transport layer/second hole transport layer/fluorescence emitting layer/electron transport layer (/electron injection layer)

(n) (hole injection layer/) first hole transport layer/second hole transport layer/phosphorescent emitting layer/electron transport layer (/electron injection layer)

(o) (hole injection layer/) first hole transport layer/second hole transport layer/fluorescent light-emitting layer/first electron transport layer/second electron transport layer (/electron injection layer)

(p) (hole injection layer/) first hole transport layer/second hole transport layer/phosphorescent emitting layer/first electron transport layer/second electron transport layer (/electron injection layer)

(q) (hole injection layer/)hole transport layer/fluorescence emitting layer/hole blocking layer/electron transport layer (/electron injection layer)

(r) (hole injection layer/)hole transport layer/phosphorescent emitting layer/hole blocking layer/electron transport layer (/electron injection layer)

(s) (hole injection layer/)hole transport layer/fluorescent light-emitting layer/exciton blocking layer/electron transport layer (/electron injection layer)

(t) (hole injection layer/)hole transport layer/phosphorescence emitting layer/exciton blocking layer/electron transport layer (/electron injection layer)

Each of the phosphorescent or fluorescent light-emitting layers may exhibit different light-emitting colors. Specifically, in the light-emitting unit (f), (hole injection layer/) hole transport layer/first phosphorescent light-emitting layer (red light-emitting)/second phosphorescent light-emitting layer (green light-emitting)/space layer/fluorescent light-emitting layer (blue light-emitting)/ A layer structure such as an electron transport layer can be mentioned.

On the other hand, an electron blocking layer may be appropriately provided between each light-emitting layer and the hole transport layer or space layer. Additionally, a hole blocking layer may be appropriately provided between each light-emitting layer and the electron transport layer. By providing an electron blocking layer or a hole blocking layer, electrons or holes can be confined in the light emitting layer, the probability of charge recombination in the light emitting layer can be increased, and light emission efficiency can be improved.

Representative device configurations of tandem organic EL devices include the following device configurations.

(2) Anode/first light emitting unit/middle layer/second light emitting unit/cathode

Here, as the first light emitting unit and the second light emitting unit, for example, each can be independently selected from the light emitting units described above.

The intermediate layer is also generally called an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, and an intermediate insulating layer, and supplies electrons to the first light-emitting unit and holes to the second light-emitting unit. Available material compositions are available.

1 is a schematic diagram showing an example of the configuration of an organic EL device of the present invention. The organic EL element 1 has a substrate 2, an anode 3, a cathode 4, and a light emitting unit 10 disposed between the anode 3 and the cathode 4. The light emitting unit 10 has a light emitting layer 5 . A hole transport band 6 (hole injection layer, hole transport layer, etc.) between the light emitting layer 5 and the anode 3, and an electron transport band 7 (electron injection layer, electron transport layer, etc.) between the light emitting layer 5 and the cathode 4. transport layer, etc.). Additionally, an electron blocking layer (not shown) may be provided on the anode 3 side of the light emitting layer 5, and a hole blocking layer (not shown) may be provided on the cathode 4 side of the light emitting layer 5. As a result, electrons and holes are confined in the light-emitting layer 5, and the generation efficiency of excitons in the light-emitting layer 5 can be further increased.

Figure 2 is a schematic diagram showing another configuration of the organic EL device of the present invention. The organic EL element 11 has a substrate 2, an anode 3, a cathode 4, and a light emitting unit 20 disposed between the anode 3 and the cathode 4. The light emitting unit 20 has a light emitting layer 5 . The hole transport zone disposed between the anode 3 and the light emitting layer 5 is formed of the hole injection layer 6a, the first hole transport layer 6b, and the second hole transport layer 6c. Additionally, the electron transport zone disposed between the light emitting layer 5 and the cathode 4 is formed by the first electron transport layer 7a and the second electron transport layer 7b.

Meanwhile, in the present invention, a host combined with a fluorescent dopant material (fluorescent light-emitting material) is called a fluorescent host, and a host combined with a phosphorescent dopant material is called a phosphorescent host. Fluorescent hosts and phosphorescent hosts are not distinguished only by their molecular structures. That is, the phosphorescent host refers to a material that forms a phosphorescent light-emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material that forms a fluorescent light-emitting layer. The same goes for fluorescent hosts.

Board

The substrate is used as a support for an organic EL device. As a substrate, for example, a plate of glass, quartz, or plastic can be used. Additionally, a flexible substrate may be used. Examples of flexible substrates include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. Additionally, an inorganic vapor deposition film can also be used.

anode

For the anode formed on the substrate, it is preferable to use metals, alloys, electrically conductive compounds, and mixtures thereof with a large work function (specifically, 4.0 eV or more). Specifically, for example, indium oxide-tin oxide (ITO: Indium Tin Oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide. , graphene, etc. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), Palladium (Pd), titanium (Ti), or nitrides of these metals (eg, titanium nitride) can be used.

These materials are usually formed into a film by a sputtering method. For example, indium oxide-zinc oxide is a target containing 1 to 10 wt% of zinc oxide relative to indium oxide, and indium oxide containing tungsten oxide and zinc oxide is a target containing 0.5 to 5 wt% of tungsten oxide to indium oxide. , it can be formed by the sputtering method by using a target containing 0.1 to 1 wt% of zinc oxide. In addition, it may be produced by vacuum deposition, coating, inkjet, spin coating, etc.

Since the hole injection layer formed in contact with the anode is formed using a material that facilitates hole injection regardless of the work function of the anode, materials commonly used as electrode materials (e.g., metals, alloys, electrically conductive compounds) , and mixtures thereof, elements belonging to group 1 or 2 of the periodic table of elements) can be used.

Materials with a small work function, elements belonging to group 1 or 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), magnesium (Mg), calcium (Ca), and strontium (Sr) ), and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), and ytterbium (Yb), and alloys containing these. On the other hand, when forming an anode using an alkali metal, an alkaline earth metal, and an alloy containing them, a vacuum deposition method or a sputtering method can be used. Additionally, when using silver paste or the like, a coating method, an inkjet method, etc. can be used.

hole injection layer

The hole injection layer is a layer containing a material with high hole injection properties (hole injection material), and is formed between the anode and the light-emitting layer, or, if present, between the hole transport layer and the anode.

Hole injection materials other than the invention compounds 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, etc. can be used.

4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviated name: TDATA), a low molecular weight organic compound, 4,4',4"-tris[N-(3-methylphenyl)- N-phenylamino]triphenylamine (abbreviated name: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated name: DPAB), 4,4'- Bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviated name: DNTPD), 1,3,5-tris[N-( 4-Diphenylaminophenyl)-N-phenylamino]benzene (abbreviated name: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated name) : PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated name: PCzPCA2), 3-[N-(1-naph) Aromatic amine compounds such as til)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviated name: PCzPCN1) can also be used as hole injection layer materials.

High molecular compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, poly(N-vinylcarbazole) (abbreviated name: PVK), poly(4-vinyltriphenylamine) (abbreviated name: PVTPA), poly[N-(4-{N'-[4-(4-) Diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated name: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl) Benzidine] (abbreviated name: Poly-TPD) and other polymer compounds. In addition, polymer compounds with added acids such as poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid) (PEDOT/PSS) and polyaniline/poly(styrenesulfonic acid) (PAni/PSS) can be used. It may be possible.

Moreover, it is also preferable to use an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K).

[Formula 98]

(In the above formula, R ₂₁ to _{R 26} each independently represent a cyano group, -CONH ₂ , a carboxyl group, or -COOR ₂₇ (R ₂₇ represents an alkyl group with 1 to 20 carbon atoms or a cycloalkyl group with 3 to 20 carbon atoms) ). In addition, two adjacent groups selected from R ₂₁ and R ₂₂ , R ₂₃ and R ₂₄ , and R ₂₅ and R ₂₆ may be combined with each other to form a group represented by -CO-O-CO-.)

Examples of R ₂₇ include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, cyclopentyl group, and cyclohexyl group.

hole transport layer

The hole transport layer is a layer containing a material with high hole transport properties (hole transport material), and is formed between the anode and the light-emitting layer, or, if present, between the hole injection layer and the light-emitting layer.

The hole transport layer may have a single-layer structure or may have a multi-layer structure containing two or more layers. For example, the hole transport layer may have a two-layer structure including a first hole transport layer (anode side) and a second hole transport layer (cathode side). In one aspect of the present invention, the hole transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, and the hole transport layer closest to the cathode in the multi-layer structure, for example, the second hole transport layer of the two-layer structure, is preferably adjacent to the light-emitting layer. It is preferable that it is adjacent to the light emitting layer. In another aspect of the present invention, an electron blocking layer, which will be described later, may be interposed between the hole transport layer and the light emitting layer in the single-layer structure, or between the hole transport layer and the light emitting layer closest to the light emitting layer in the multilayer structure.

As the hole transport layer material, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used.

Examples of aromatic amine compounds include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated name: NPB) and N,N'-bis(3-methylphenyl)- N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated name: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)tri Phenylamine (abbreviated name: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviated name: DFLDPBi), 4,4', 4"-tris(N,N-diphenylamino)triphenylamine (abbreviated name: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated name: TDATA) : MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviated name: BSPB). The compound has a hole mobility of 10 ^-6 cm ² /Vs or more.

As carbazole derivatives, for example, 4,4'-di(9-carbazolyl)biphenyl (abbreviated name: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviated name: CBP) CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviated name: PCzPA).

Anthracene derivatives include, for example, 2-t-butyl-9,10-di(2-naphthyl)anthracene (abbreviated name: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviated name: DNA) ), and 9,10-diphenylanthracene (abbreviated name: DPAnth).

High molecular compounds such as poly(N-vinylcarbazole) (abbreviated name: PVK) or poly(4-vinyltriphenylamine) (abbreviated name: PVTPA) can also be used.

However, compounds other than the above may be used as long as they have higher hole transport properties than electron transport properties.

Dopant material of the emitting layer

The light-emitting layer is a layer containing a highly luminescent material (dopant material), and various materials can be used. For example, a fluorescent material or a phosphorescent material can be used as a dopant material. A fluorescent material is a compound that emits light from a singlet excited state, and a phosphorescent material is a compound that emits light from a triplet excited state.

As a blue-based fluorescent material that can be used in the light-emitting layer, pyrene derivatives, styrylamine derivatives, chryssen derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. can be used. Specifically, N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviated name: YGA2S), 4 -(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviated name: YGAPA), 4-(10-phenyl-9-anthryl)-4'- (9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated name: PCBAPA), etc.

As a green fluorescent material that can be used in the light-emitting layer, an aromatic amine derivative or the like can be used. Specifically, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviated name: 2PCAPA), N-[9,10-bis( 1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviated name: 2PCABPhA), N-(9,10-diphenyl- 2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated name: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2- 1)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated name: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl) -2-yl)]-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracene-2-amine (abbreviated name: 2YGABPhA), N,N,9-triphenylanthracene-9 -Amines (abbreviated name: DPhAPhA), etc. can be mentioned.

As red fluorescent materials that can be used in the light-emitting layer, tetracene derivatives, diamine derivatives, etc. can be used. Specifically, N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviated name: p-mPhTD), 7,14-diphenyl-N,N,N ',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviated name: p-mPhAFD), etc.

In one aspect of the present invention, it is preferable that the light-emitting layer contains a fluorescent light-emitting material (fluorescent dopant material).

As a blue-based phosphorescent material that can be used in the light-emitting layer, metal complexes such as iridium complex, osmium complex, and platinum complex are used. Specifically, bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) tetrakis(1-pyrazolyl)borate (abbreviated name: FIr6), bis [2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviated name: FIrpic), bis[2-(3',5'-bis) Trifluoromethylphenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviated name: Ir(CF3ppy)2(pic)), bis[2-(4',6'-difluorophenyl) ) pyridinato-N, C2'] iridium (III) acetylacetonate (abbreviated name: FIracac), etc.

As a green phosphorescent material that can be used in the light-emitting layer, an iridium complex or the like is used. Tris(2-phenylpyridinato-N,C2')iridium(III) (abbreviated name: Ir(ppy)3), bis(2-phenylpyridinato-N,C2')iridium(III) acetylaceto Nate (abbreviated name: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazoleto)iridium(III) acetylacetonate (abbreviated name: Ir(pbi)2(acac)), and bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviated name: Ir(bzq)2(acac)).

As red phosphorescent materials that can be used in the light-emitting layer, metal complexes such as iridium complex, platinum complex, terbium complex, and europium complex are used. Specifically, bis[2-(2'-benzo[4,5-α]thienyl)pyridinato-N,C3']iridium(III) acetylacetonate (abbreviated name: Ir(btp)2( acac)), bis(1-phenylisoquinolinato-N,C2')iridium(III) acetylacetonate (abbreviated name: Ir(piq)2(acac)), (acetylacetonate)bis[2,3 -bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviated name: Ir(Fdpq)2(acac)), 2,3,7,8,12,13,17,18-octaethyl- and organometallic complexes such as 21H,23H-porphyrin platinum(II) (abbreviated name: PtOEP).

In addition, tris(acetylacetonate)(monophenanthroline)terbium(III) (abbreviated name: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedionato) (Monophenanthroline) Europium(III) (abbreviated name: Eu(DBM)3(Phen)), Tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenane Trolin) Rare earth metal complexes such as europium(III) (abbreviated name: Eu(TTA)3(Phen)) can be used as phosphorescent materials because they emit light (electron transition between different multiplicities) from rare earth metal ions. there is.

In one aspect of the present invention, it is preferable that the light-emitting layer contains a phosphorescent light-emitting material (phosphorescent dopant material).

Host material of the emitting layer

The light emitting layer may have a structure in which the above-described dopant material is dispersed in another material (host material). It is preferable to use a material that has a higher lowest empty orbital level (LUMO level) and a lower highest occupied orbital level (HOMO level) than the dopant material.

As a host material, for example

(1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes,

(2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives,

(3) Condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives;

(4) Aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives are used.

For example, tris(8-quinolinoleto)aluminum(III) (abbreviated name: Alq), tris(4-methyl-8-quinolinoleto)aluminum(III) (abbreviated name: Almq3), bis(10- Hydroxybenzo[h]quinolinato)beryllium(II) (abbreviated name: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolate)aluminium(III) (abbreviated name: BAlq) , bis(8-quinolinoleto)zinc(II) (abbreviated name: Znq), bis[2-(2-benzoxazolyl)phenolate]zinc(II) (abbreviated name: ZnPBO), bis[2-(2) -benzothiazolyl)phenolate]metal complexes such as zinc(II) (abbreviated name: ZnBTZ);

2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated name: PBD), 1,3-bis[5-(p-tert-butyl) Phenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviated name: OXD-7), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl) -1,2,4-triazole (abbreviated name: TAZ), 2,2',2"-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviated name: TPBI ), heterocyclic compounds such as vasophenanthroline (abbreviated name: BPhen), and vassocuproine (abbreviated name: BCP);

9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviated name: CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl) Phenyl]-9H-carbazole (abbreviated name: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviated name: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviated name: DNA) ), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviated name: t-BuDNA), 9,9'-bianthryl (abbreviated name: BANT), 9,9'-(stilbene -3,3'-diyl) diphenanthrene (abbreviated name: DPNS), 9,9'-(stilbene-4,4'-diyl) diphenanthrene (abbreviated name: DPNS2), 3,3',3 "-(benzene-1,3,5-triyl)tripyrene (abbreviated name: TPB3), 9,10-diphenylanthracene (abbreviated name: DPAnth), 6,12-dimethoxy-5,11-diphenylcrylate condensed aromatic compounds such as Sen et al.; and

N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviated name: CzA1PA), 4-(10-phenyl-9-anthryl) ) Triphenylamine (abbreviated name: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviated name: PCAPA), N ,9-Diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazol-3-amine (abbreviated name: PCAPBA), N-(9,10- Diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviated name: 2PCAPA), 4,4'-bis[N-(1-naphthyl)-N-phenylamino ]Biphenyl (abbreviated name: NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated name: TPD), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviated name: DFLDPBi), 4,4'-bis[ Aromatic amine compounds such as N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviated name: BSPB) can be used. Multiple types of host materials may be used.

In particular, in the case of a blue fluorescent element, it is preferable to use the following anthracene compound as a host material.

[Formula 99]

[Formula 100]

[Formula 101]

electron transport layer

The electron transport layer is a layer containing a material with high electron transport properties (electron transport material), and is formed between the light emitting layer and the cathode, or, if present, between the electron injection layer and the light emitting layer. The inventive compound may be used in the electron transport layer alone or in combination with a compound described later.

The electron transport layer may have a single-layer structure or a multi-layer structure containing two or more layers. For example, the electron transport layer may have a two-layer structure including a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one aspect of the present invention, the electron transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, and the electron transport layer closest to the anode in the multi-layer structure, for example, the first electron transport layer of the two-layer structure, is It is preferable that it is adjacent to the light emitting layer. In another aspect of the present invention, a hole blocking layer, which will be described later, may be interposed between the electron transport layer and the light emitting layer in the single-layer structure, or between the electron transport layer and the light emitting layer closest to the light emitting layer in the multilayer structure.

In the electron transport layer having the above two-layer structure, the inventive compound may be contained in one or both of the first electron transport layer and the second electron transport layer.

In one aspect of the present invention, the invention compound is preferably contained only in the first electron transport layer, in another aspect, the invention compound is preferably contained only in the second electron transport layer, and in another aspect, the invention compound is preferably contained in the second electron transport layer. It is preferably included in the first electron transport layer and the second electron transport layer.

In one aspect of the present invention, the inventive compound contained in one or both of the first electron transport layer and the second electron transport layer is preferably a light hydrogen compound from the viewpoint of production cost.

The light hydrogen body is an invention compound in which all hydrogen atoms in the invention compound are light hydrogen atoms.

Accordingly, the present invention includes an organic EL device in which one or both of the first electron transport layer and the second electron transport layer contain the invention compound substantially composed only of light hydrogen elements. “Invention compound consisting substantially only of light hydrogen elements” means that the content ratio of light hydrogen elements to the total amount of the invention compound is 90 mol% or more, preferably 95 mol% or more, more preferably 99 mol% or more (each 100%) includes).

In the electron transport layer, for example,

(1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes,

(2) Heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives,

(3) High molecular compounds can be used.

Examples of metal complexes include tris(8-quinolinoleto)aluminum(III) (abbreviated name: Alq), tris(4-methyl-8-quinolinoleto)aluminum (abbreviated name: Almq3), and bis(10). -Hydroxybenzo[h]quinolinato)beryllium (abbreviated name: BeBq ₂ ), bis(2-methyl-8-quinolinolato)(4-phenylphenolate)aluminium(III) (abbreviated name: BAlq), Bis(8-quinolinoleto)zinc(II) (abbreviated name: Znq), bis[2-(2-benzoxazolyl)phenolate]zinc(II) (abbreviated name: ZnPBO), bis[2-(2- Benzothiazolyl) phenolate] zinc (II) (abbreviated name: ZnBTZ).

Heteroaromatic compounds include, for example, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated name: PBD), 1,3-bis. [5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviated name: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5- (4-biphenylyl)-1,2,4-triazole (abbreviated name: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl )-1,2,4-triazole (abbreviated name: p-EtTAZ), vasophenanthroline (abbreviated name: BPhen), vassocuproine (abbreviated name: BCP), 4,4'-bis (5-methylbenzoxa Zol-2-yl)stilbene (abbreviated name: BzOs) can be mentioned.

Examples of polymer compounds include poly[(9,9-dhexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated name: PF-Py), poly Examples include [(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated name: PF-BPy). .

The material has an electron mobility of 10 ^-6 cm ² /Vs or more. On the other hand, materials other than those mentioned above may be used for the electron transport layer as long as they have higher electron transport properties than hole transport properties.

electron injection layer

The electron injection layer is a layer containing a material with high electron injection properties. The electron injection layer contains alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), europium (Eu), and ytterbium (Yb). rare earth metals, and compounds containing these metals can be used. Such compounds include, for example, alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes, alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, rare earth metal oxides, and rare earths. Metal halides and organic complexes containing rare earth metals can be mentioned. Additionally, a plurality of these compounds can be mixed and used.

In addition, a material having electron transport properties containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a material containing magnesium (Mg) in Alq may be used. On the other hand, in this case, electron injection from the cathode can be performed more efficiently.

Alternatively, a composite material formed by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer. Such a composite material has excellent electron injection and electron transport properties because the organic compound accepts electrons from an electron donor. In this case, the organic compound is preferably a material excellent in transporting electrons. Specifically, for example, materials constituting the electron transport layer described above (metal complexes, heteroaromatic compounds, etc.) can be used. The electron donor may be any material that is electron-donating to an organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferable, and examples include lithium, cesium, magnesium, calcium, erbium, and ytterbium. Additionally, alkali metal oxides and alkaline earth metal oxides are preferable, and examples include lithium oxide, calcium oxide, and barium oxide. Additionally, a Lewis base such as magnesium oxide may be used. Additionally, organic compounds such as tetraciafulvalene (abbreviated name: TTF) can also be used.

cathode

For the cathode, it is preferable to use metals, alloys, electrically conductive compounds, and mixtures thereof with a small work function (specifically, 3.8 eV or less). Specific examples of such negative electrode materials include elements belonging to group 1 or 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg), calcium (Ca), and strontium ( Alkaline earth metals such as Sr) and alloys containing them (for example, MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.

On the other hand, when forming a cathode using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum deposition method or a sputtering method can be used. Additionally, when using silver paste or the like, a coating method, an inkjet method, etc. can be used.

On the other hand, by providing an electron injection layer, a cathode can be formed using various conductive materials such as Al, Ag, ITO, graphene, silicon, or indium oxide-tin oxide containing silicon oxide, regardless of the work function. can do. These conductive materials can be formed into a film using sputtering, inkjet, spin coating, etc.

insulating layer

Organic EL elements are prone to pixel defects due to leaks or short circuits because an electric field is applied to an ultra-thin film. To prevent this, an insulating layer made of an insulating thin film layer may be inserted between a pair of electrodes.

Materials used in the insulating layer include, for example, aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, and germanium oxide. nium, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, etc. On the other hand, mixtures or laminates thereof may be used.

space floor

The space layer is, for example, when stacking a fluorescent emitting layer and a phosphorescent emitting layer, it is provided between the fluorescent emitting layer and the phosphorescent emitting layer for the purpose of preventing excitons generated in the phosphorescent emitting layer from diffusing into the fluorescent emitting layer or adjusting the carrier balance. This is the floor that becomes Additionally, the space layer can also be provided between a plurality of phosphorescent light-emitting layers.

Since the space layer is provided between the light emitting layers, it is preferably a material that has both electron transport properties and hole transport properties. Additionally, in order to prevent diffusion of triplet energy in adjacent phosphorescent emitting layers, it is preferable that the triplet energy is 2.6 eV or more. Materials used in the space layer include the same materials used in the hole transport layer described above.

low floor

A blocking layer such as an electron blocking layer, a hole blocking layer, or an exciton blocking layer may be provided adjacent to the light emitting layer. The electron blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole transport layer, and the hole blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron transport layer. The exciton-blocking layer has the function of preventing excitons generated in the light-emitting layer from diffusing into surrounding layers and confining the excitons within the light-emitting layer.

In one aspect of the present invention, it is preferable that the electron transport zone includes a hole blocking layer on the cathode side, and that the hole blocking layer includes the inventive compound. Additionally, it is preferable that the hole blocking layer is adjacent to the light emitting layer.

Each layer of the organic EL device can be formed by conventionally known deposition methods, coating methods, etc. For example, deposition methods such as vacuum deposition and molecular beam deposition (MBE), or coating methods such as dipping, spin coating, casting, bar coating, and roll coating using a solution of a layer-forming compound. It can be formed by a known method.

The film thickness of each layer is not particularly limited, but in general, if the film thickness is too thin, defects such as pinholes are likely to occur, and if the film thickness is too thick, a high driving voltage is required and efficiency deteriorates, so it is usually 5 nm to 10 μm, and 10 nm ~0.2μm is more preferred.

The organic EL element can be used in display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and electronic devices such as lighting and light-emitting devices such as vehicle lamps.

Example

Hereinafter, the present invention will be described in more detail using examples, but the present invention is not limited to the following examples.

Inventive compounds used for producing organic EL devices (I) of Examples 1 to 4

[Formula 102]

Comparative compounds used in the production of organic EL devices (I) of Comparative Examples 1 to 3

[Formula 103]

Other compounds used in the production of organic EL devices (I)

[Formula 104]

Fabrication of organic EL device (I)

Example 1

A 25 mm x 75 mm x 1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonic cleaned in isopropyl alcohol for 5 minutes and then cleaned with UV ozone for 30 minutes. The film thickness of ITO was 130 nm.

Attachment of cleaned ITO transparent electrode The glass substrate is mounted on a substrate holder of a vacuum evaporation device, and first, the transparent electrode is covered on the side where the transparent electrode is formed, and then the compound HT-1 and the compound HI-1 are co-deposited. , a hole injection layer with a film thickness of 10 nm was formed. The mass ratio (HT-1:HI-1) of compound HT-1 and compound HI-1 was 97:3.

Next, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer with a film thickness of 80 nm.

Next, EBL-1 was deposited on this first hole transport layer to form a second hole transport layer with a film thickness of 10 nm.

Next, on this second hole transport layer, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited to form a light emitting layer with a film thickness of 25 nm. The mass ratio of compound BH-1 and compound BD-1 (BH-1:BD-1) was 96:4.

Next, Compound 1 was deposited on this light emitting layer to form a first electron transport layer with a film thickness of 10 nm.

Next, on this first electron transport layer, compound ET-1 was deposited to form a second electron transport layer with a film thickness of 15 nm.

Next, LiF was deposited on this second electron transport layer to form an electron injecting electrode with a film thickness of 1 nm.

Then, metal Al was deposited on this electron injecting electrode to form a metal cathode with a film thickness of 50 nm.

The layer structure of the organic EL device (I) of Example 1 obtained in this way is shown below.

ITO (130)/HT-1:HI-1=97:3 (10)/HT-1 (80)/EBL-1 (10)/BH-1:BD-1=96:4 (25)/compound 1 (10)/ET-1 (15)/LiF (1)/Al (50)

In the above layer configuration, the numbers in parentheses are the film thickness (nm), and the ratio is the mass ratio.

Measurement of device life (LT90)

The obtained organic EL device (I) was driven by direct current at a current density of 50 mA/cm ² at room temperature, the time (h) until the luminance decreased to 90% of the initial luminance was measured, and this was measured as the 90% lifespan (LT90). I did it. The results are shown in Table 1.

Examples 2 to 4

An organic EL device (I) was produced in the same manner as in Example 1 except that the first electron transport layer material was changed to a compound shown in Table 1 below, and LT90 was measured. The results are shown in Table 1.

Comparative Examples 1 to 3

Each organic EL device (I) was produced in the same manner as in Example 1 except that the first electron transport layer material was changed to the compound shown in Table 1 below, and LT90 was measured. The results are shown in Table 1.

From the results in Table 1, it can be seen that compared to the comparative compounds, the compounds of the present invention provide organic EL devices with significantly improved device lifespan.

Inventive compounds used for producing organic EL devices (II) of Examples 5 to 8

[Formula 105]

Comparative compounds used in the production of organic EL devices (II) of Comparative Examples 4 to 6

[Formula 106]

Other compounds used in the production of organic EL devices (II)

[Formula 107]

Fabrication of organic EL device (II)

Example 5

A 25 mm x 75 mm x 1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonic cleaned in isopropyl alcohol for 5 minutes and then cleaned with UV ozone for 30 minutes. The film thickness of ITO was 130 nm.

Attaching the cleaned ITO transparent electrode The glass substrate is mounted on a substrate holder of a vacuum evaporation device, and first, the transparent electrode is covered on the side where the transparent electrode is formed, and then the compound HT-1 and the compound HI-1 are co-deposited. , a hole injection layer with a film thickness of 10 nm was formed. The mass ratio (HT-1:HI-1) of compound HT-1 and compound HI-1 was 97:3.

Next, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer with a film thickness of 80 nm.

Next, EBL-1 was deposited on this first hole transport layer to form a second hole transport layer with a film thickness of 5 nm.

Next, on this second hole transport layer, compound BH-2 (host material) and compound BD-1 (dopant material) were co-deposited to form a light emitting layer with a film thickness of 25 nm. The mass ratio of compound BH-2 and compound BD-1 (BH-2:BD-1) was 96:4.

Next, Compound 1 was deposited on this light-emitting layer to form a first electron transport layer with a film thickness of 5 nm.

Next, on this first electron transport layer, compounds ET-2 and Liq were co-deposited to form a second electron transport layer with a film thickness of 20 nm. The mass ratio of compounds ET-2 and Liq (ET-2:Liq) was 50:50.

Next, Yb was deposited on this second electron transport layer to form an electron injecting electrode with a film thickness of 1 nm.

Then, metal Al was deposited on this electron injecting electrode to form a metal cathode with a film thickness of 50 nm.

The LT90 of the organic EL device (II) of Example 5 obtained in this way was measured in the same manner as Example 1. The results are shown in Table 2, and the layer structure of the organic EL device (II) of Example 5 is shown below.

ITO (130)/HT-1:HI-1=97:3 (10)/HT-1 (80)/EBL-1 (5)/BH-2:BD-1=96:4 (25)/compound 1 (5)/ET-2:Liq=50:50 (20)/Yb (1)/Al (50)

In the above layer configuration, the numbers in parentheses are the film thickness (nm), and the ratio is the mass ratio.

Examples 6 to 8

Each organic EL device (II) was produced in the same manner as in Example 5 except that the first electron transport layer material was changed to a compound shown in Table 2 below, and LT90 was measured. The results are shown in Table 2.

Comparative Examples 4 to 6

Each organic EL device (II) was produced in the same manner as in Example 5 except that the first electron transport layer material was changed to a compound shown in Table 2 below, and LT90 was measured. The results are shown in Table 2.

From the results in Table 2, it can be seen that compared to the comparative compounds, the compounds of the present invention provide organic EL devices with significantly improved device lifespan.

Inventive compounds used for producing organic EL devices (III) of Examples 9 to 18

[Formula 108]

Other compounds used in the production of organic EL devices (III)

[Formula 109]

Fabrication of organic EL device (III)

Example 9

A 25 mm x 75 mm x 1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonic cleaned in isopropyl alcohol for 5 minutes and then cleaned with UV ozone for 30 minutes. The film thickness of ITO was 130 nm.

Attaching the cleaned ITO transparent electrode The glass substrate is mounted on a substrate holder of a vacuum evaporation device, and first, the transparent electrode is covered on the side where the transparent electrode is formed, and then the compound HT-1 and the compound HI-1 are co-deposited. , a hole injection layer with a film thickness of 10 nm was formed. The mass ratio (HT-1:HI-1) of compound HT-1 and compound HI-1 was 97:3.

Next, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer with a film thickness of 80 nm.

Next, EBL-1 was deposited on this first hole transport layer to form a second hole transport layer with a film thickness of 10 nm.

Next, on this second hole transport layer, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited to form a light emitting layer with a film thickness of 25 nm. The mass ratio of compound BH-1 and compound BD-1 (BH-1:BD-1) was 96:4.

Next, on this light-emitting layer, Compound 5 was deposited to form a first electron transport layer with a film thickness of 10 nm.

Next, compound ET-1 was deposited on this first electron transport layer to form a second electron transport layer with a film thickness of 15 nm.

Next, LiF was deposited on this second electron transport layer to form an electron injecting electrode with a film thickness of 1 nm.

Then, metal Al was deposited on this electron injecting electrode to form a metal cathode with a film thickness of 50 nm.

The LT90 of the organic EL device (III) of Example 5 obtained in this way was measured in the same manner as Example 1. The results are shown in Table 3, and the layer structure of the organic EL device (III) of Example 9 is shown below.

ITO (130)/HT-1:HI-1=97:3 (10)/HT-1 (80)/EBL-1 (10)/BH-1:BD-1=96:4 (25)/compound 5 (10)/ET-1 (15)/LiF (1)/Al (50)

In the above layer configuration, the numbers in parentheses are the film thickness (nm), and the ratio is the mass ratio.

Examples 10 to 18

Each organic EL device (III) was produced in the same manner as in Example 9 except that the first electron transport layer material was changed to the compound shown in Table 3 below, and LT90 was measured. The results are shown in Table 3.

From the results in Table 3, it can be seen that compared to the comparative compounds, the compounds of the present invention provide organic EL devices with significantly improved device lifespan.

Compounds synthesized in Synthesis Examples 1 to 15

[Formula 110]

Intermediate Synthesis Example 1: Synthesis of Intermediate A

[Formula 111]

4-Bromo-1-naphthaldehyde (9.0 g), 4-acetylbiphenyl (7.5 g), and sodium hydroxide (0.15 g) were added to 300 mL of ethanol, and stirred at room temperature for 5 hours. Next, benzamidine hydrochloride (6.0 g) and sodium hydroxide (1.8 g) were added, and the mixture was stirred at 70°C for 5 hours. After completion of the reaction, the precipitate was separated by filtration and purified by silica gel column chromatography (developing solvent: hexane/toluene) to obtain Intermediate A (7.5 g, yield 38%) as a white solid.

Intermediate Synthesis Example 2: Synthesis of Intermediate D

[Formula 112]

4-Bromo-1-naphthaldehyde (9.0 g), 3-acetylbiphenyl (7.5 g), and sodium hydroxide (0.15 g) were added to 300 mL of ethanol, and stirred at room temperature for 5 hours. Next, benzamidine hydrochloride (6.0 g) and sodium hydroxide (1.8 g) were added, and the mixture was stirred at 70°C for 5 hours. After completion of the reaction, the precipitate was separated by filtration and purified by silica gel column chromatography (developing solvent; hexane/toluene) to obtain Intermediate D (5.9 g, yield 30%) as a white solid.

Intermediate Synthesis Example 3: Synthesis of Intermediate K

[Formula 113]

Under argon atmosphere, 5'-chloro-1,1':3',1"-terphenyl-2,2",3,3",4,4",5,5",6,6"-d10( 10.0g, 36.4mmol), bispinacholatodiborone (10.2g, 40.0mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (798mg), potassium acetate (5.36g) , 54.6 mmol), dioxane (200 ml) was added, and the mixture was heated and stirred at 100°C for 12 hours. After completion of the reaction, the solvent was concentrated and the resulting residue was purified by column chromatography to obtain a white solid (11.5 g, yield 86%). The obtained white solid was intermediate K, as a result of mass spectrum analysis (m/e = 366 for molecular weight 366.3).

Intermediate Synthesis Example 4: Synthesis of Intermediate L

[Formula 114]

Under argon atmosphere, intermediate K (11.0 g, 30.0 mmol), 4,6-dichloro-2-phenylpyrimidine (7.43 g, 33.0 mmol), tetrakis(triphenylphosphine)palladium (0) (1.73 g) , Dimethoxyethane (200 ml) and water (40 ml) were added to potassium carbonate (8.30 g, 60.1 mmol), and the mixture was heated and stirred at 50°C for 12 hours. After completion of the reaction, extraction was performed with ethyl acetate, the organic layer was concentrated, and the obtained residue was purified by column chromatography to obtain a white solid (6.2 g, yield 48%). The obtained white solid was intermediate L as a result of mass spectrum analysis (m/e = 429 for molecular weight 429.0).

Synthesis Example 1: Synthesis of Compound 1

[Formula 115]

Intermediate A (4.7 g) and 4-(2-dibenzofuranyl)phenylboronic acid (3.4 g) were added to 1,2-dimethoxyethane (90 mL), and argon gas was passed through the solution for 5 minutes. PdCl ₂ (Amphos) ₂ (0.26 g) and sodium carbonate aqueous solution (2M, 12 mL) were added thereto, and the mixture was heated at 75° C. for 17 hours while stirring in an argon atmosphere. The solvent was distilled off from the reaction solution, and the obtained solid was purified by silica gel column chromatography (developing solvent: hexane/toluene) to obtain a white solid (5.6 g, yield 90%).

The obtained white solid was Compound 1, as a result of mass spectrum analysis (m/e = 676 for molecular weight 676.82).

Synthesis Example 2: Synthesis of Compound 2

[Formula 116]

The synthesis was carried out in the same manner as in Synthesis Example 1, except that dibenzofuran-2-boronic acid (1.4 g) was used instead of intermediate A (2.5 g) and 4-(2-dibenzofuranyl)phenylboronic acid. A white solid (2.6 g, yield 88%) was obtained.

The obtained white solid was Compound 2, as a result of mass spectrum analysis (m/e = 600 for molecular weight 600.72).

Synthesis Example 3: Synthesis of Compound 3

[Formula 117]

In Synthesis Example 1, Intermediate A (5.0 g) and 3-(2-dibenzofuranyl)phenylboronic acid (3.1 g) were used instead of 4-(2-dibenzofuranyl)phenylboronic acid. Other than that, the synthesis was performed in the same manner to obtain a white solid (3.2 g, yield 48%).

The obtained white solid was Compound 3, as a result of mass spectrum analysis (m/e = 676 for molecular weight 676.82).

Synthesis Example 4: Synthesis of Compound 4

[Formula 118]

In Synthesis Example 1, Intermediate A (5.0 g), except that 4-(4-dibenzofuranyl)phenylboronic acid (3.1 g) was used instead of 4-(2-dibenzofuranyl)phenylboronic acid. The synthesis was performed similarly to obtain a white solid (4.9 g, yield 74%).

The obtained white solid was Compound 4, as a result of mass spectrum analysis (m/e = 676 for molecular weight 676.82).

Synthesis Example 5: Synthesis of Compound 5

[Formula 119]

In Synthesis Example 1, Intermediate A (4.0 g) and 4-(2-dibenzofuranyl)phenylboronic acid were replaced with Intermediate B (2.4 g) synthesized in the same manner as described in International Publication No. 2010/137285. ), the synthesis was performed in the same manner except that ) to obtain a white solid (4.5 g, yield 88%).

The obtained white solid was Compound 5, as a result of mass spectrum analysis (m/e = 650 for molecular weight 650.78).

Synthesis Example 6: Synthesis of Compound 6

[Formula 120]

In Synthesis Example 1, Intermediate A (3.5 g) and 4-(2-dibenzofuranyl)phenylboronic acid were replaced with Intermediate C (2.1 g) synthesized in the same manner as described in International Publication No. 2010/137285. ), the synthesis was performed in the same manner, and a white solid (4.1 g, yield 92%) was obtained.

The obtained white solid was Compound 6, as a result of mass spectrum analysis (m/e = 650 for molecular weight 650.78).

Synthesis Example 7: Synthesis of Compound 7

[Formula 121]

In Synthesis Example 1, intermediate D (2.5 g) was used instead of intermediate (A), and dibenzofuran-2-boronic acid (1.4 g) was used instead of 4-(2-dibenzofuranyl)phenylboronic acid. The synthesis was performed in the same manner except that , a white solid (2.1 g, yield 71%) was obtained.

The obtained white solid was Compound 7, as a result of mass spectrum analysis (m/e = 600 for molecular weight 600.72).

Synthesis Example 8: Synthesis of Compound 8

[Formula 122]

Synthesis was performed in the same manner as in Synthesis Example 1, except that dibenzothiophene-2-boronic acid (1.3 g) was used instead of intermediate A (2.5 g) and 4-(2-dibenzofuranyl)phenylboronic acid. , a white solid (2.0 g, yield 67%) was obtained.

The obtained white solid was Compound 8, as a result of mass spectrum analysis (m/e = 616 for molecular weight 616.78).

Synthesis Example 9: Synthesis of Compound 9

[Formula 123]

The synthesis was performed in the same manner as in Synthesis Example 1, except that Intermediate E (2.3 g) was used instead of Intermediate A (5.0 g) and 4-(2-dibenzofuranyl)phenylboronic acid, and a white solid (3.2 g, Yield 55%) was obtained.

The obtained white solid was compound 9, as a result of mass spectrum analysis (m/e = 601 for molecular weight 600.7).

Synthesis Example 10: Synthesis of Compound 10

[Formula 124]

The synthesis was carried out in the same manner as in Synthesis Example 1, except that Intermediate F (2.3 g) was used instead of Intermediate A (5.0 g) and 4-(2-dibenzofuranyl)phenylboronic acid, and a white solid (5.3 g, Yield 91%) was obtained.

The obtained white solid was Compound 10, as a result of mass spectrum analysis (m/e = 601 for molecular weight 600.7).

Synthesis Example 11: Synthesis of Compound 11

[Formula 125]

Synthesis was carried out in the same manner as in Synthesis Example 1, except that Intermediate G (2.2 g) was used instead of Intermediate A (5.0 g) and 4-(2-dibenzofuranyl)phenylboronic acid, and a white solid (2.2 g, Yield 38%) was obtained.

The obtained white solid was Compound 11, as a result of mass spectrum analysis (m/e = 651 for molecular weight 650.7).

Synthesis Example 12: Synthesis of Compound 12

[Formula 126]

The synthesis was carried out in the same manner as in Synthesis Example 1, except that Intermediate H (6.6 g) was used instead of Intermediate A (7.0 g) and 4-(2-dibenzofuranyl)phenylboronic acid, and a white solid (6.2 g, Yield 73%) was obtained.

The obtained white solid was Compound 12, as a result of mass spectrum analysis (m/e = 691 for molecular weight 690.8).

Synthesis Example 13: Synthesis of Compound 13

[Formula 127]

The synthesis was carried out in the same manner as in Synthesis Example 1, except that Intermediate I (4.5 g) was used instead of Intermediate A (5.0 g) and 4-(2-dibenzofuranyl)phenylboronic acid, and a white solid (5.7 g, Yield 85%) was obtained.

The obtained white solid was Compound 13, as a result of mass spectrum analysis (m/e = 691 for molecular weight 690.8).

Synthesis Example 14: Synthesis of Compound 14

[Formula 128]

The synthesis was carried out in the same manner as in Synthesis Example 1, except that Intermediate J (2.8 g) was used instead of Intermediate A (5.0 g) and 4-(2-dibenzofuranyl)phenylboronic acid, and a white solid (4.6 g, Yield 73%) was obtained.

The obtained white solid was compound 14, as a result of mass spectrum analysis (m/e = 651 for molecular weight 650.7).

Synthesis Example 15: Synthesis of Compound 15

[Formula 129]

Synthesis was carried out in the same manner as in Synthesis Example 1, except that intermediate L (5.0 g) was used instead of intermediate A (5.0 g), and intermediate M (5.4 g) was used instead of 4-(2-dibenzofuranyl)phenylboronic acid. This was performed to obtain a white solid (6.3 g, yield 79%).

The obtained white solid was Compound 15, as a result of mass spectrum analysis (m/e = 687 for molecular weight 686.9).

1, 11 Organic EL device
2 substrate
3 anode
4 cathode
5 emitting layer
6 Hole transport zone (hole transport layer)
6a hole injection layer
6b first hole transport layer
6c second hole transport layer
7 Electron transport zone (electron transport layer)
7a first electron transport layer
7b second electron transport layer
10, 20 luminous units

Claims (37)

A compound represented by the following formula (1).

(In equation (1),
Ar ¹ to ^{Ar 3} each independently represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
L ¹ is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, and Ar ² and L ¹ are bonded to each other to form a substituted or unsubstituted arylene group. An unsubstituted ring may be formed.
L ² is a single bond or a 2+p-valent residue of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 25 ring carbon atoms.
p is 0 or 1, when L ² is a single bond, p is 0, and when L ² is a 2+p valent residue of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 25 ring carbon atoms, p is 0 or 1.
R ¹ to R ⁶ and R ¹¹ to ^{R 14} are each independently,
hydrogen atom,
halogen Atom,
Cyanogi,
nitrogi,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
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 group represented by Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),
A group represented by -O-(R ₉₀₄ ),
A group represented by -S-(R ₉₀₅ ),
A group represented by -N(R ₉₀₆ )(R ₉₀₇ ),
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or
It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
R ₉₀₁ to R ₉₀₇ are each independently,
hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or
It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
When two or more R _901s exist, the two or more R _901s are the same as or different from each other,
When two or more R _902s exist, the two or more R _902s are the same as or different from each other,
When two or more R ₉₀₃ exist, the two or more R ₉₀₃ are the same as or different from each other,
When two or more R _904s exist, the two or more R _904s are the same as or different from each other,
When two or more R _905s exist, the two or more R _905s are the same as or different from each other,
When two or more R _906s exist, the two or more R _906s are the same as or different from each other,
When two or more R _907s exist, the two or more R _907s are the same or different from each other,
R ¹ and R ² do not combine with each other to form a ring,
In one or more groups selected from R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ¹¹ and R ¹² , R ¹² and R ¹³ , and R ¹³ and R ¹⁴ , two adjacent ones are bonded to each other Thus, a substituted or unsubstituted ring may be formed.
X ¹ is an oxygen atom or a sulfur atom.
*d is bonded to one carbon atom selected from *a, *b, and *c.) According to claim 1,
A compound represented by any one of the following formulas (1A) to (1C).

(In formulas (1A) to (1C),
R ²¹ to R ²⁵ and R ³¹ to ^{R 38} are each independently,
hydrogen atom,
halogen Atom,
Cyanogi,
nitrogi,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
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 group represented by Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),
A group represented by -O-(R ₉₀₄ ),
A group represented by -S-(R ₉₀₅ ),
A group represented by -N(R ₉₀₆ )(R ₉₀₇ ),
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or
It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
step,
In equation (1A),
When p is 0, the other one selected from R ²¹ to R ²⁵ is a single bond bonded to *f,
When p is 1, one selected from R ²¹ to ^{R 25} is a single bond bonded to *e, and the other bond selected from R ²¹ to R ²⁵ is a single bond bonded to *f,
In equation (1B),
When p is 0, one selected from R ³¹ to ^{R 38} is a single bond bonded to *g, and the other bond selected from R ³¹ to R ³⁸ is a single bond bonded to *i,
When p is 1, one selected from R ³¹ to ^{R 38} is a single bond bonded to *g, the other bond selected from R ³¹ to R ³⁸ is a single bond bonded to *h, and R ³¹ to Another one selected from R ³⁸ is a single bond bonded to *i.
Ar ¹ ∼Ar ³ , L ¹ , p ^, R ¹ ∼R ⁶ _, ^{R 11} ∼R ₁₄ , It is as defined.) The method of claim 1 or 2,
A compound represented by the following formula (1A-1) or (1B-1).

(In formulas (1A-1) and (1B-1),
Ar ¹ , Ar ² , L ¹ , R ¹ to R ⁶ , R ¹¹ to R ¹⁴ , X ¹ , *a, *b, *c, and *d are as defined in formula (1), and R ²¹ to R ²⁶ , and *f are as defined in Formula (1A), and R ³¹ to R ³⁸ , *g, and *i are as defined in Formula (1B).) The method according to any one of claims 1 to 3,
A compound represented by the following formula (1A-1a) or (1A-1b).

(In formulas (1A-1a) and (1A-1b),
Ar ¹ , Ar ² , L ¹ , R ¹ to R ⁶ , R ¹¹ to R ¹⁴ , X ¹ , *a, *b, *c, and *d are as defined in formula (1), and R ²¹ to R ²⁵ is as defined in equation (1A).) The method according to any one of claims 1 to 3,
A compound represented by the following formula (1A-1c).

(In formula (1A-1c),
Ar ¹ , Ar ² , L ¹ , R ¹ to R ⁶ , R ¹¹ to R ¹⁴ , and X ¹ are as defined in formula (1), and R ²¹ to ^{R 25} and *f are as defined in formula (1A). As defined.) The method of claim 1 or 2,
A compound represented by the following formula (1C-1a).

(In formula (1C-1a),
Ar ¹ , Ar ² , L ¹ , R ¹ to R ⁶ , R ¹¹ to R ¹⁴ , and X ¹ are as defined in formula (1).) The method according to any one of claims 1 to 6,
Ar ¹ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. The method according to any one of claims 1 to 7,
A compound in which the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms represented by Ar ¹ is selected from a phenyl group, a biphenyl group, and a naphthyl group. The method according to any one of claims 1 to 7,
Ar ² is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. The method according to any one of claims 1 to 8,
A compound in which the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms represented by Ar ² is selected from a phenyl group, a biphenyl group, and a naphthyl group. The method according to any one of claims 1 to 9,
L ¹ is a compound wherein L 1 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms. The method according to any one of claims 1 to 10,
A compound in which the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms represented by L ¹ is selected from phenylene group, biphenylene group, and naphthylene group. The method according to any one of claims 1 to 11,
A compound in which R ¹ to R ⁶ are all hydrogen atoms. The method according to any one of claims 1 to 12,
A compound in which R ¹¹ to R ¹⁴ are all hydrogen atoms. The method according to any one of claims 1 to 13,
A compound represented by the above formula (1) containing at least one deuterium atom. A compound represented by the following formula (2).

(In equation (2),
Ar ¹¹ to ^{Ar 13} each independently represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
L ¹¹ is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, and Ar ¹² and L ¹² are bonded to each other to form a substituted or unsubstituted arylene group. An unsubstituted ring may be formed.
L ¹² is a 2+q valent residue of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 25 ring carbon atoms.
q is 0 or 1.
R ⁴¹ to R ⁴⁶ and R ⁵¹ to ^{R 54} are each independently,
hydrogen atom,
halogen Atom,
Cyanogi,
nitrogi,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
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 group represented by Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),
A group represented by -O-(R ₉₀₄ ),
A group represented by -S-(R ₉₀₅ ),
A group represented by -N(R ₉₀₆ )(R ₉₀₇ ),
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or
It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
R ₉₀₁ to R ₉₀₇ are each independently,
hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or
It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
When two or more R _901s exist, the two or more R _901s are the same as or different from each other,
When two or more R _902s exist, the two or more R _902s are the same as or different from each other,
When two or more R ₉₀₃ exist, the two or more R ₉₀₃ are the same as or different from each other,
When two or more R _904s exist, the two or more R _904s are the same as or different from each other,
When two or more R _905s exist, the two or more R _905s are the same as or different from each other,
When two or more R _906s exist, the two or more R _906s are the same as or different from each other,
When two or more R _907s exist, the two or more R _907s are the same or different from each other,
R ⁴¹ and R ⁴² do not combine with each other to form a ring,
In one or more groups selected from R ⁴³ and R ⁴⁴ , R ⁴⁴ and R ⁴⁵ , R ⁴⁵ and R ⁴⁶ , R ⁵¹ and R ⁵² , R ⁵² and R ⁵³ , and R ⁵³ and R ⁵⁴ , two adjacent ones are bonded to each other Thus, a substituted or unsubstituted ring may be formed.
X ¹¹ is an oxygen atom or a sulfur atom.) According to claim 16,
A compound represented by the following formula (2A) or (2B).

(In formulas (2A) and (2B),
R ⁶¹ to R ⁶⁵ and R ⁷¹ to ^{R 74} are each independently,
hydrogen atom,
halogen Atom,
Cyanogi,
nitrogi,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
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 group represented by Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),
A group represented by -O-(R ₉₀₄ ),
A group represented by -S-(R ₉₀₅ ),
A group represented by -N(R ₉₀₆ )(R ₉₀₇ ),
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or
It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
step,
In equation (2A),
When q is 0, the other one selected from R ⁶¹ to R ⁶⁵ is a single bond bonded to *k,
When q is 1, one selected from R ⁶¹ to ^{R 65} is a single bond bonded to *j, and the other selected from R ⁶¹ to R ⁶⁵ is a single bond bonded to *k,
In equation (2B),
When q is 0, one selected from R ⁷¹ to R ⁷⁸ is a single bond bonded to *l, and the other bond selected from R ⁷¹ to R ⁷⁸ is a single bond bonded to *m,
When q is 1, one selected from R ⁷¹ to R ⁷⁸ is a single bond bonded to *l, the other bond selected from R ⁷¹ to R ⁷⁸ is a single bond bonded to *m, and R ⁷¹ to Another one selected from R ⁷⁸ is a single bond bonded to *n.
Ar ¹¹ to Ar ¹³ , L ¹¹ , q, R ⁴¹ to R ⁴⁶ , R ⁵¹ to R ⁵⁴ , X ¹¹ , and R ₉₀₁ to R ₉₀₇ are as defined in formula (2).) The method of claim 16 or 17,
A compound represented by the following formula (2A-1) or (2B-1).

(In formulas (2A-1) and (2B-1),
Ar ¹¹ and Ar ¹² , L ¹¹ , R ⁴¹ to R ⁴⁶ , R ⁵¹ to R ⁵⁴ , and X ¹¹ are as defined in formula (2), and R ⁶¹ to ^{R 65} and *k are as defined in formula (2A) As defined, R ⁷¹ to R ⁷⁸ , *l, and *n are as defined in equation (2B).) The method according to any one of claims 16 to 18,
A compound represented by the following formula (2A-1a) or (2A-1b).

(In formulas (2A-1a) and (2B-1b),
Ar ¹¹ and Ar ¹² , L ¹¹ , R ⁴¹ to R ⁴⁶ , R ⁵¹ to ^{R 54} , and X ¹¹ are as defined in Formula (2), and R ⁶¹ to ^{R 66} are as defined in Formula (2A). ) The method according to any one of claims 16 to 19,
Ar ¹¹ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. The method according to any one of claims 16 to 20,
A compound in which the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms represented by Ar ¹¹ is selected from a phenyl group, a biphenyl group, and a naphthyl group. The method according to any one of claims 16 to 21,
Ar ¹² is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. The method according to any one of claims 16 to 22,
A compound in which the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms represented by Ar ¹² is selected from a phenyl group, a biphenyl group, and a naphthyl group. The method according to any one of claims 16 to 23,
L ¹¹ is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms. The method according to any one of claims 16 to 24,
A compound in which the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms represented by L ¹¹ is selected from phenylene group, biphenylene group, and naphthylene group. The method according to any one of claims 16 to 25,
A compound in which R ⁴¹ to R ⁴⁶ are all hydrogen atoms. The method according to any one of claims 16 to 26,
A compound in which R ⁵¹ to R ⁵⁴ are all hydrogen atoms. The method according to any one of claims 16 to 27,
A compound represented by the above formula (2) containing at least one deuterium atom. A material for an organic electroluminescent device comprising the compound according to any one of claims 1 to 28. An organic electroluminescence device having a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer includes a light-emitting layer, and at least one layer of the organic layer is the compound according to any one of claims 1 to 28. An organic electroluminescent device containing a. According to claim 30,
An organic electroluminescent device, wherein the organic layer includes an electron transport zone between the cathode and the light-emitting layer, and the electron transport zone includes the compound. According to claim 31,
An organic electroluminescent device, wherein the electron transport zone includes a first electron transport layer on the cathode side and a second electron transport layer on the cathode side, and the first electron transport layer, the second electron transport layer, or both contain the compound. The method of claim 31 or 32,
An organic electroluminescent device, wherein the electron transport zone further includes a hole blocking layer on the cathode side, and the hole blocking layer includes the compound. According to claim 33,
An organic electroluminescent device, wherein the hole blocking layer is adjacent to the light emitting layer. The method according to any one of claims 30 to 34,
An organic electroluminescent device, wherein the light-emitting layer includes a fluorescent dopant material. The method according to any one of claims 30 to 34,
An organic electroluminescent device, wherein the light-emitting layer includes a phosphorescent dopant material. An electronic device comprising the organic electroluminescent device according to any one of claims 30 to 36.