CN116897605A

CN116897605A - Organic electroluminescent element and electronic device

Info

Publication number: CN116897605A
Application number: CN202280016796.2A
Authority: CN
Inventors: 高桥佑典; 羽毛田匡; 田中将太; 深见拓人; 泽藤司; 糸井裕亮
Original assignee: Idemitsu Kosan Co Ltd
Current assignee: Idemitsu Kosan Co Ltd
Priority date: 2021-02-26
Filing date: 2022-01-07
Publication date: 2023-10-17

Abstract

An organic electroluminescent element, and an electronic device including the same, the organic electroluminescent element having a cathode, an anode, and an organic layer between the cathode and the anode, the organic layer including a light-emitting layer, the organic layer including a compound represented by the following formula (1) and a compound represented by the following formula (2). In the formula (1), N ^＊、R ¹ ～R ⁸ 、R ¹¹ ～R ¹⁸ 、L ¹ ～L ³ 、Ar ¹ 、Ar ² And a to e are as defined in formula (1). In the formula (2), L ¹¹ And L ¹² 、Ar ¹¹ 、R ²¹ ～R ²⁸ 、R ³¹ ～R ³⁸ And f is as defined in formula (2).

Description

Organic electroluminescent element and electronic device

Technical Field

The present invention relates to an organic electroluminescent element and an electronic device including the same.

Background

In general, an organic electroluminescent element (hereinafter, also referred to as an "organic EL element") is composed of an anode, a cathode, and an organic layer interposed between the anode and the cathode. When a voltage is applied between the electrodes, electrons are injected from the cathode side into the light-emitting region, holes are injected from the anode side into the light-emitting region, and the injected electrons and holes recombine in the light-emitting region to generate an excited state, and light is emitted when the excited state returns to the ground state. Therefore, it is important to find a combination of materials that efficiently transport electrons or holes to a light emitting region and allow the electrons and holes to be easily recombined to efficiently generate excitons in order to obtain a high-performance organic EL element.

Patent documents 1 to 5 disclose compounds used as materials for organic electroluminescent elements.

Prior art literature

Patent literature

Patent document 1: international publication No. 2020/075769

Patent document 2: international publication No. 2020/075784

Patent document 3: international publication No. 2016/190600

Patent document 4: chinese publication No. 111440156

Patent document 5: korean laid-open patent publication No. 10-2020-0053284

Disclosure of Invention

Problems to be solved by the invention

Conventionally, many compounds for organic EL elements have been reported, but there is still a need for further improvement in the performance of organic EL elements.

The present invention has been made to solve the above-described problems, and an object of the present invention is to provide an organic EL element having further improved element performance by including a combination of specific compounds, and an electronic device including such an organic EL element.

Means for solving the problems

The present inventors have conducted intensive studies on the performance of an organic EL element comprising the compound described in patent documents 1 to 5, and as a result, have found that an organic EL element comprising the compound represented by the following formula (1) and the compound represented by the following formula (2) exhibits higher performance.

In one embodiment, the present invention provides an organic electroluminescent element having a cathode, an anode, and an organic layer between the cathode and the anode, the organic layer including a light-emitting layer, the organic layer including a compound represented by the following formula (1) and a compound represented by the following formula (2).

[ chemical formula 1]

(in the formula (1),

N ^＊ is a central nitrogen atom.

R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ Each independently is

A hydrogen atom,

Halogen atom,

Cyano group,

Nitro group,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

Substituted or unsubstituted cycloalkyl having 3 to 50 ring members,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ) A group shown,

-O-(R ₉₀₄ ) A group shown,

-S-(R ₉₀₅ ) A group shown,

-N(R ₉₀₆ )(R ₉₀₇ ) A group shown,

Substituted or unsubstituted aryl groups having 6 to 50 ring members, or

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

R ₉₀₁ ～R ₉₀₇ each independently is

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted cycloalkyl having 3 to 50 ring members,

Substituted or unsubstituted aryl groups having 6 to 50 ring members, or

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

At R ₉₀₁ When there are 2 or more, 2 or more R ₉₀₁ Are the same as or different from each other,

at R ₉₀₂ When there are 2 or more, 2 or more R ₉₀₂ Are the same as or different from each other,

at R ₉₀₃ When there are 2 or more, 2 or more R ₉₀₃ Are the same as or different from each other,

at R ₉₀₄ When there are 2 or more, 2 or more R ₉₀₄ Are the same as or different from each other,

at R ₉₀₅ There are 2 or moreIn the case of the above, 2 or more R ₉₀₅ Are the same as or different from each other,

at R ₉₀₆ When there are 2 or more, 2 or more R ₉₀₆ Are the same as or different from each other,

at R ₉₀₇ When there are 2 or more, 2 or more R ₉₀₇ The same or different from each other.

n is 0 or 1.

Wherein,,

when n is 0, the number of the n-type organic electroluminescent element,

R ¹ and R is R ² 、R ² And R is R ³ Or R is ³ One of R4 is a single bond to a bond with a, the other is a single bond to a bond with b,

r is selected from single bonds other than those bound to a and b ¹ ～R ⁴ 、R ⁵ ～R ⁸ And R is ¹¹ ～R ¹⁴ 1 of them is a single bond to the ene bond,

when n is 1, the number of the n-type organic electroluminescent element,

R ¹ and R is R ² 、R ² And R is R ³ Or R is ³ And R is R ⁴ One of them is a single bond to a bond with a, the other is a single bond to a bond with b,

R ⁵ and R is R ⁶ 、R ⁶ And R is R ⁷ Or R is ⁷ And R is R ⁸ One of them is a single bond to the group C and the other is a single bond to the group d,

r is selected from single bonds other than those bound to a and b ¹ ～R ⁴ R is not a single bond to both C and d ⁵ ～R ⁸ 、R ¹¹ ～R ¹⁴ And R is ¹⁵ ～R ¹⁸ 1 of them is a single bond to the ene bond.

X ¹ Is an oxygen atom or a sulfur atom.

Ar ¹ And Ar is a group ² Each independently represents a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming carbon atoms.

L ¹ ～L ³ Each independently is a single bond, substituted or unsubstitutedArylene having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms. )

[ chemical formula 2]

(in the formula (2),

L ¹¹ and L ¹² Each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming carbon atoms.

Ar ¹¹ Is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming carbon atoms.

R ²¹ ～R ²⁸ And R is ³¹ ～R ³⁸ Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

X ² Is an oxygen atom, a sulfur atom, or CR ^a R ^b ，

R ^a And R is ^b Is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, R ^a And R is R ^b May be bonded to each other to form a substituted or unsubstituted ring.

Wherein,,

selected from R ³¹ ～R ³³ 、R ³⁶ ～R ³⁸ 、R ^a And R is ^b 1 of them is a single bond to the f,

selected from R other than the single bonds mentioned ³¹ ～R ³⁸ The adjacent 2 of the two may be bonded to each other to form a ring, or may not form a ring. )

In another aspect, the present invention provides an electronic device comprising the above organic electroluminescent element.

In still another aspect, the present invention provides a composition comprising a compound represented by the above formula (1) and a compound represented by the above formula (2).

ADVANTAGEOUS EFFECTS OF INVENTION

An organic EL element having an organic layer containing a compound represented by the following formula (1) and a compound represented by the following formula (2) exhibits improved element performance.

Drawings

Fig. 1 is a schematic diagram showing an example of a layer structure of an organic EL element according to an embodiment of the present invention.

Fig. 2 is a schematic diagram showing another example of the layer structure of the organic EL element according to the embodiment of the present invention.

Fig. 3 is a schematic view showing another example of the layer structure of the organic EL element according to the embodiment of the present invention.

Detailed Description

[ definition ]

In the present specification, the hydrogen atom means to contain isotopes having different neutron numbers, namely protium (protium), deuterium (deuterium) and tritium (tritium).

In the present specification, in the chemical structural formula, the symbol such as "R" and the bondable position of "D" indicating deuterium atom are not explicitly shown, and are set to be bonded with hydrogen atom, i.e., protium atom, deuterium atom or tritium atom.

In the present specification, the number of ring-forming carbon refers to the number of carbon atoms among atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic compound, a condensed cyclic compound, a bridged cyclic compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbons. The "number of ring-forming carbons" described below is set similarly unless otherwise indicated. For example, the number of ring-forming carbons of the benzene ring is 6, the number of ring-forming carbons of the naphthalene ring is 10, the number of ring-forming carbons of the pyridine ring is 5, and the number of ring-forming carbons of the furan ring is 4. In addition, for example, the ring-forming carbon number of 9, 9-diphenylfluorenyl is 13,9,9' -spirobifluorenyl and the ring-forming carbon number is 25.

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

In the present specification, the number of ring-forming atoms refers to the number of atoms constituting the ring itself of a compound (for example, a monocyclic compound, a condensed compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) having a structure in which atoms are bonded in a ring (for example, a single ring, a condensed ring, and a bridged ring). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate bonds to atoms that constitute a ring), and atoms that are contained in a substituent when the ring is substituted with a substituent are not included in the number of ring-forming atoms. The "number of ring-forming atoms" described below is set similarly unless otherwise indicated. For example, the number of ring-forming atoms of the pyridine ring is 6, the number of ring-forming atoms of the quinazoline ring is 10, and the number of ring-forming atoms of the furan ring is 5. For example, the number of hydrogen atoms bonded to the pyridine ring or atoms constituting the substituent is not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms of the pyridine ring to which the hydrogen atom or the substituent is bonded is 6. In addition, for example, a hydrogen atom bonded to a carbon atom of a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms of the quinazoline ring. Accordingly, the number of ring-forming atoms of the quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

In the present specification, "carbon number XX to YY" in the expression of "a substituted or unsubstituted ZZ group of carbon number XX to YY" means the carbon number when the ZZ group is unsubstituted, and the carbon number of the substituent when the substitution occurs is not included. Here, "YY" is larger than "XX", where "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

In the present specification, "the number of atoms XX to YY" in the expression of "the number of atoms XX to YY of the substituent" is not included, and the number of atoms XX to YY of the substituent when the substituent is unsubstituted is the number of atoms when the substituent is unsubstituted. Here, "YY" is larger than "XX", where "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

In the present specification, an unsubstituted ZZ group means that "a substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group means that "a substituted or unsubstituted ZZ group" is a "substituted ZZ group".

In the present specification, "unsubstituted" when expressed as "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 protium atom, deuterium atom or tritium atom.

In the present specification, "substitution" when referring to "substituted or unsubstituted ZZ group" means that 1 or more hydrogen atoms in the ZZ group are replaced with substituents. The term "substitution" when referring to "BB group substituted with AA group" means that 1 or more hydrogen atoms in BB group are replaced with AA group.

"substituent described in the specification"

Substituents described in the present specification are described below.

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

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

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

The carbon number of the "unsubstituted alkenyl group" described in the present specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise described in the present specification.

The carbon number of the "unsubstituted alkynyl" described in the present specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise described in the present specification.

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

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

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

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

"substituted or unsubstituted aryl"

Specific examples of the "substituted or unsubstituted aryl group" described in the present specification (specific example group G1) include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B). (herein, unsubstituted aryl means that "substituted or unsubstituted aryl" is "unsubstituted aryl", and substituted aryl means that "substituted or unsubstituted aryl" is "substituted aryl"), and in this specification, only "aryl" is referred to, both "unsubstituted aryl" and "substituted aryl" are included.

"substituted aryl" refers to a group in which 1 or more hydrogen atoms of an "unsubstituted aryl" are replaced with a substituent. Examples of the "substituted aryl" include a group obtained by replacing 1 or more hydrogen atoms of the "unsubstituted aryl" of the following specific example group G1A with substituents, and a substituted aryl of the following specific example group G1B. The examples of "unsubstituted aryl" and "substituted aryl" listed herein are only examples, and the "substituted aryl" described in the present specification also includes a group in which a hydrogen atom bonded to a carbon atom of an aryl group itself in the "substituted aryl" of the following specific example group G1B is further substituted with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted aryl" of the following specific example group G1B is further substituted with a substituent.

Unsubstituted aryl (specific example group G1A):

phenyl group,

P-biphenyl group,

M-biphenyl group,

O-biphenyl group,

P-terphenyl-4-yl,

Para-terphenyl-3-yl,

Para-terphenyl-2-yl,

M-terphenyl-4-yl,

M-terphenyl-3-yl,

M-terphenyl-2-yl,

O-terphenyl-4-yl,

O-terphenyl-3-yl,

O-terphenyl-2-yl,

1-naphthyl group,

2-naphthyl group,

Anthracenyl group,

Benzoanthryl radical,

Phenanthryl group,

Benzophenanthryl radical,

Phenalkenyl group,

Pyrenyl group,

A base group,

Benzo (E) benzo (EA base group,

Triphenylene group,

Benzotriphenylene radical,

And tetraphenyl group,

Pentacenyl,

Fluorenyl group,

9,9' -spirobifluorenyl,

Benzofluorenyl group,

Dibenzofluorenyl group,

Fluorescent anthracyl group,

Benzofluoranthenyl group,

Perylene groups

Monovalent aromatic groups derived by removing 1 hydrogen atom from the ring structures represented by the following general formulae (TEMP-1) to (TEMP-15).

[ chemical formula 3]

[ chemical formula 4]

Substituted aryl (specific example group G1B):

o-tolyl group,

M-tolyl group,

P-tolyl group,

P-xylyl radical,

M-xylyl radical,

O-xylyl radical,

P-isopropylphenyl group,

M-isopropylphenyl group,

O-isopropylphenyl group,

P-tert-butylphenyl group,

M-tert-butylphenyl group,

O-tert-butylphenyl group,

3,4, 5-trimethylphenyl group,

9, 9-dimethylfluorenyl group,

9, 9-diphenylfluorenyl

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

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

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

Cyanophenyl group,

Triphenylsilylphenyl radical,

Trimethylsilylphenyl group,

Phenyl naphthyl group,

Naphthyl phenyl

A monovalent group derived from the ring structure represented by the general formulae (TEMP-1) to (TEMP-15) wherein 1 or more hydrogen atoms and substituents are substituted.

"substituted or unsubstituted heterocyclyl"

The "heterocyclic group" described in the present specification is a cyclic group having at least 1 heteroatom as a ring-forming atom. Specific examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.

The "heterocyclic group" described in the present specification is a monocyclic group or a condensed ring group.

The "heterocyclic group" described in the present specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

Specific examples of the "substituted or unsubstituted heterocyclic group" described in the present specification (specific example group G2) include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). (herein, the unsubstituted heterocyclic group means a case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group means a case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group"). In this specification, only the "heterocyclic group" is expressed to include both the "unsubstituted heterocyclic group" and the "substituted heterocyclic group".

"substituted heterocyclic group" means a group in which 1 or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with a substituent. Specific examples of the "substituted heterocyclic group" include a group in which a hydrogen atom of the "unsubstituted heterocyclic group" of the following specific example group G2A is substituted, and examples of the substituted heterocyclic group of the following specific example group G2B. Examples of the "unsubstituted heterocyclic group" and examples of the "substituted heterocyclic group" mentioned herein are only examples, and the "substituted heterocyclic group" described in the present specification includes a group in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic group" of the specific example group G2B is further substituted with a substituent, and a group in which a hydrogen atom of the substituent in the "substituted heterocyclic group" of the specific example group G2B is further substituted with a substituent.

Specific examples of the group G2A include, for example, the following unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A 1), an unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A 2), an unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A 3), and a monovalent heterocyclic group derived by removing 1 hydrogen atom from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A 4).

Specific examples of the group G2B include, for example, the following substituted heterocyclic group containing a nitrogen atom (specific example group G2B 1), substituted heterocyclic group containing an oxygen atom (specific example group G2B 2), substituted heterocyclic group containing a sulfur atom (specific example group G2B 3), and a group obtained by substituting 1 or more hydrogen atoms and substituents of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2B 4).

Unsubstituted heterocyclyl containing a nitrogen atom (specific example group G2 A1):

pyrrole group,

Imidazolyl group,

Pyrazolyl radical,

Triazolyl radical,

Tetrazolyl group,

Oxazolyl group,

Isoxazolyl radical,

Oxadiazolyl group,

Thiazolyl group,

Isothiazolyl group,

Thiadiazolyl group,

A pyridyl group,

Pyridazinyl group,

Pyrimidinyl group,

Pyrazinyl group,

Triazinyl group,

Indolyl group,

Isoindolyl group,

An indolizinyl group,

Quinolizinyl group,

Quinolinyl radical,

Isoquinolinyl radical,

Cinnolinyl radical,

Phthalazinyl radical,

Quinazolinyl group,

Quinoxalinyl group,

Benzimidazolyl group,

Indazolyl group,

Phenanthroline group,

Phenanthridinyl group,

Acridinyl group,

Phenazinyl group,

Carbazolyl group,

Benzocarbazolyl group,

Morpholinyl group,

Phenoxazinyl group,

Phenothiazinyl group,

Azacarbazolyl, and diazacarbazolyl.

Unsubstituted heterocyclyl containing an oxygen atom (specific example group G2 A2):

Furyl group,

Oxazolyl group,

Isoxazolyl radical,

Oxadiazolyl group,

Xanthenyl,

Benzofuranyl group,

Isobenzofuranyl group,

Dibenzofuranyl group,

Naphthobenzofuranyl group,

Benzoxazolyl group,

Benzisoxazolyl group,

Phenoxazinyl group,

Morpholinyl group,

Dinaphthofuranyl group,

Azadibenzofuranyl radical,

Diazadibenzofuranyl radical,

Azanaphthobenzofuranyl groups

Naphthyridobenzofuranyl.

Unsubstituted heterocyclyl containing a sulfur atom (specific example group G2 A3):

thienyl group,

Thiazolyl group,

Isothiazolyl group,

Thiadiazolyl group,

Benzothienyl (benzothienyl),

Isobenzothienyl (isobenzothienyl),

Dibenzothienyl (dibenzothienyl),

Naphthobenzothienyl (naphthobenzothienyl),

Benzothiazolyl group,

Benzisothiazolyl group,

Phenothiazinyl group,

Dinaphthiophenyl (dinaphthothienyl),

Azadibenzothienyl (azadibenzothienyl),

Diazadibenzothienyl (diazadibenzothienyl),

Azanaphthacenebenzothienyl (azanapthobenzothiadienyl), and

naphthyridobenzothienyl (diazaphthibenzoienyl).

Monovalent heterocyclic groups derived by removing 1 hydrogen atom from the ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (concrete example group G2A 4):

[ chemical formula 5]

[ chemical formula 6]

In the above general formulae (TEMP-16) to (TEMP-33), X _A And Y _A Each independently is an oxygen atom, a sulfur atom, NH or CH ₂ . Wherein X is _A And Y _A At least 1 of them is an oxygen atom, a sulfur atomOr NH.

In the above general formulae (TEMP-16) to (TEMP-33), X _A And Y _A At least any one of (C) is NH or CH ₂ In the case where the monovalent heterocyclic groups derived from the ring structures represented by the above general formulae (TEMP-16) to (TEMP-33) include those derived from NH or CH ₂ A monovalent group obtained by removing 1 hydrogen atom.

Substituted heterocyclyl containing a nitrogen atom (specific example group G2B 1):

(9-phenyl) carbazolyl group,

(9-biphenylyl) carbazolyl group,

(9-phenyl) phenylcarbazolyl group,

(9-naphthyl) carbazolyl group,

Diphenylcarbazol-9-yl,

Phenylcarbazol-9-yl,

Methyl benzimidazolyl group,

Ethylbenzimidazolyl group,

Phenyl triazinyl radical,

Biphenyl triazinyl radical,

Diphenyl triazinyl radical,

Phenyl quinazolinyl

Biphenylquinazolinyl.

Substituted heterocyclyl containing an oxygen atom (specific example group G2B 2):

phenyl dibenzofuranyl group,

Methyl dibenzofuranyl group,

Tert-butyldibenzofuranyl group

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

Substituted heterocyclyl containing a sulfur atom (specific example group G2B 3):

Phenyl dibenzothienyl,

Methyl dibenzothienyl,

Tert-butyldibenzothienyl

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

A monovalent heterocyclic group derived from the ring structures represented by the general formulae (TEMP-16) to (TEMP-16) above, wherein 1 or more hydrogen atoms and substituents are substituted (concrete example group G2B 4):

the above-mentioned "1 or more hydrogen atoms of the monovalent heterocyclic group" means a hydrogen atom or X bonded to a ring-forming carbon atom selected from the monovalent heterocyclic group _A And Y _A At least one of the nitrogen atoms bonded to the nitrogen atom when NH is selected from the group consisting of _A And Y _A One of them is CH ₂ More than 1 hydrogen atom in the methylene hydrogen atoms.

"substituted or unsubstituted alkyl"

Specific examples of the "substituted or unsubstituted alkyl group" described in the present specification (specific example group G3) include the following unsubstituted alkyl group (specific example group G3A) and substituted alkyl group (specific example group G3B). (herein, unsubstituted alkyl means that "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl means that "substituted or unsubstituted alkyl" is "substituted alkyl") hereinafter, when only "alkyl" is expressed, both "unsubstituted alkyl" and "substituted alkyl" are included.

"substituted alkyl" refers to a group in which 1 or more hydrogen atoms in the "unsubstituted alkyl" are replaced with a substituent. Specific examples of the "substituted alkyl" include the following "unsubstituted alkyl" (specific example group G3A), a group in which 1 or more hydrogen atoms and substituents have been replaced, and a substituted alkyl (specific example group G3B). In the present specification, an alkyl group in "unsubstituted alkyl group" means a chain-like alkyl group. Thus, "unsubstituted alkyl" includes "unsubstituted alkyl" as a straight chain and "unsubstituted alkyl" as a branched chain. The examples of "unsubstituted alkyl" and "substituted alkyl" mentioned herein are only examples, and the "substituted alkyl" described in the present specification includes a group in which a hydrogen atom of an alkyl group itself in the "substituted alkyl" of the specific example group G3B is further substituted with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkyl" of the specific example group G3B is further substituted with a substituent.

Unsubstituted alkyl (specific example group G3A):

methyl group,

Ethyl group,

N-propyl group,

Isopropyl group,

N-butyl group,

Isobutyl group,

Sec-butyl, and

and (3) tert-butyl.

Substituted alkyl (specific example group G3B):

heptafluoropropyl (including isomers),

Pentafluoroethyl group,

2, 2-trifluoroethyl group, and

trifluoromethyl.

"substituted or unsubstituted alkenyl"

Specific examples of the "substituted or unsubstituted alkenyl group" described in the present specification (specific example group G4) include the following unsubstituted alkenyl group (specific example group G4A) and substituted alkenyl group (specific example group G4B). (herein, unsubstituted alkenyl means that "substituted or unsubstituted alkenyl" is "unsubstituted alkenyl", and "substituted alkenyl" means that "substituted or unsubstituted alkenyl" is "substituted alkenyl"), and in this specification, only expression of "alkenyl" includes both "unsubstituted alkenyl" and "substituted alkenyl".

"substituted alkenyl" refers to a group in which 1 or more hydrogen atoms in the "unsubstituted alkenyl" 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 examples of the substituted alkenyl group (specific example group G4B). The examples of "unsubstituted alkenyl" and "substituted alkenyl" listed herein are only examples, and the "substituted alkenyl" described in this specification includes a group in which a hydrogen atom of an alkenyl group itself in the "substituted alkenyl" of the specific example group G4B is further substituted with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkenyl" of the specific example group G4B is further substituted with a substituent.

Unsubstituted alkenyl (specific example group G4A):

vinyl group,

Allyl group,

1-butenyl,

2-butenyl

3-butenyl.

Substituted alkenyl (specific example group G4B):

1, 3-butadienyl,

1-methyl vinyl group,

1-methylallyl,

1, 1-dimethylallyl group,

2-methylallyl

1, 2-dimethylallyl.

"substituted or unsubstituted alkynyl"

Specific examples of the "substituted or unsubstituted alkynyl group" described in the present specification (specific example group G5) include the following unsubstituted alkynyl group (specific example group G5A) and the like. (herein, unsubstituted alkynyl refers to the case where "substituted or unsubstituted alkynyl" is "unsubstituted alkynyl"), and when only "alkynyl" is described below, both "unsubstituted alkynyl" and "substituted alkynyl" are included.

"substituted alkynyl" refers to a group in which 1 or more hydrogen atoms in "unsubstituted alkynyl" are replaced with substituents. Specific examples of the "substituted alkynyl" include an "unsubstituted alkynyl" described below (specific examples group G5A) in which 1 or more hydrogen atoms and substituents are replaced.

Unsubstituted alkynyl (concrete example group G5A):

Ethynyl group

"substituted or unsubstituted cycloalkyl"

Specific examples of the "substituted or unsubstituted cycloalkyl group" described in the present specification (specific example group G6) include an unsubstituted cycloalkyl group (specific example group G6A) and a substituted cycloalkyl group (specific example group G6B) described below. (herein, unsubstituted cycloalkyl means that "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and substituted cycloalkyl means that "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl"). In this specification, only "cycloalkyl" is expressed, and both "unsubstituted cycloalkyl" and "substituted cycloalkyl" are included.

"substituted cycloalkyl" refers to a group in which 1 or more hydrogen atoms in the "unsubstituted cycloalkyl" have been replaced with a substituent. Specific examples of the "substituted cycloalkyl group" include an "unsubstituted cycloalkyl group" (specific example group G6A) in which 1 or more hydrogen atoms and substituents are replaced, and a substituted cycloalkyl group (specific example group G6B) described below. The examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" mentioned herein are only examples, and the term "substituted cycloalkyl" as used herein includes a group in which 1 or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl" of the specific example group G6B are replaced with a substituent, and a group in which the hydrogen atom of the substituent in the "substituted cycloalkyl" of the specific example group G6B is further replaced with a substituent.

Unsubstituted cycloalkyl (specific example group G6A):

cyclopropyl group,

Cyclobutyl group,

Cyclopentyl group,

Cyclohexyl group,

1-adamantyl group,

2-adamantyl group,

1-norbornyl group

2-norbornyl.

Substituted cycloalkyl (specific example group G6B):

4-methylcyclohexyl.

·“-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ) The radicals shown are'

As-Si described in the present specification(R ₉₀₁₎ (R ₉₀₂ )(R ₉₀₃ ) Specific examples of the group (specific examples group G7) shown may be given

-Si(G1)(G1)(G1)、

-Si(G1)(G2)(G2)、

-Si(G1)(G1)(G2)、

-Si(G2)(G2)(G2)、

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

-Si (G6). Here the number of the elements is the number,

g1 is "substituted or unsubstituted aryl" as described in the concrete example group G1.

G2 is a "substituted or unsubstituted heterocyclic group" as described in the concrete example group G2.

G3 is "substituted or unsubstituted alkyl group" described in the concrete example group G3.

G6 is "substituted or unsubstituted cycloalkyl" as described in the concrete example group G6.

-a plurality of G1 in Si (G1) being the same or different from each other.

-a plurality of G2 of Si (G1) (G2) being the same or different from each other.

-a plurality of G1 s of Si (G1) (G2) being the same or different from each other.

-a plurality of G2 in Si (G2) being the same or different from each other.

-a plurality of G3 in Si (G3) being the same or different from each other.

-a plurality of G6 of Si (G6) being the same or different from each other.

·“-O-(R ₉₀₄ ) The radicals shown are'

As-O- (R) s described in the specification ₉₀₄ ) Specific examples of the group (specific examples group G8) shown may be given

-O(G1)、

-O(G2)、

-O (G3) and

-O(G6)。

here the number of the elements is the number,

·“-S-(R ₉₀₅ ) The radicals shown are'

As described in the specification, S- (R) ₉₀₅ ) Specific examples of the group (specific examples group G9) shown may be given

-S(G1)、

-S(G2)、

-S (G3) and

-S(G6)。

here the number of the elements is the number,

·“-N(R ₉₀₆ )(R ₉₀₇ ) The radicals shown are'

As-N (R) described in the present specification ₉₀₆ )(R ₉₀₇ ) Specific examples of the group (group G10) shown may be given

-N(G1)(G1)、

-N(G2)(G2)、

-N(G1)(G2)、

-N (G3) (G3) and

-N(G6)(G6)。

here the number of the elements is the number,

-a plurality of G1 in N (G1) being the same or different from each other.

-a plurality of G2 in N (G2) being the same or different from each other.

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

-a plurality of G6 in N (G6) being the same or different from each other.

"halogen atom"

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

"substituted or unsubstituted fluoroalkyl"

The term "substituted or unsubstituted fluoroalkyl" as used herein refers to a group in which at least 1 hydrogen atom bonded to a carbon atom constituting an alkyl group in the term "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and includes a group (perfluoro group) in which all hydrogen atoms bonded to a carbon atom constituting an alkyl group in the term "substituted or unsubstituted alkyl group" are replaced with a fluorine atom. Unless otherwise indicated in the present specification, the carbon number of the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, more preferably 1 to 18. "substituted fluoroalkyl" refers to a radical obtained by replacing 1 or more hydrogen atoms of "fluoroalkyl" with substituents. The term "substituted fluoroalkyl" as used herein includes a group in which 1 or more hydrogen atoms bonded to a carbon atom of an alkyl chain in the term "substituted fluoroalkyl" are further substituted with a substituent, and a group in which 1 or more hydrogen atoms of a substituent in the term "substituted fluoroalkyl" are further substituted with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include those obtained by replacing 1 or more hydrogen atoms and fluorine atoms in the "alkyl group" (specific example group G3).

"substituted or unsubstituted haloalkyl"

The term "substituted or unsubstituted haloalkyl" as used herein refers to a group in which at least 1 hydrogen atom bonded to a carbon atom constituting an alkyl group in the term "substituted or unsubstituted alkyl" is replaced with a halogen atom, and includes a group in which all hydrogen atoms bonded to a carbon atom constituting an alkyl group in the term "substituted or unsubstituted alkyl" are replaced with a halogen atom. The carbon number of the "unsubstituted haloalkyl" is 1 to 50, preferably 1 to 30, more preferably 1 to 18, unless otherwise stated in the specification. "substituted haloalkyl" refers to a radical obtained by substituting 1 or more hydrogen atoms of "haloalkyl" with substituents. The term "substituted haloalkyl" as used herein also includes a group in which 1 or more hydrogen atoms bonded to a carbon atom of an alkyl chain in the term "substituted haloalkyl" are further substituted with a substituent, and a group in which 1 or more hydrogen atoms of a substituent in the term "substituted haloalkyl" are further substituted with a substituent. Specific examples of the "unsubstituted haloalkyl group" include those wherein 1 or more hydrogen atoms and halogen atoms in the above-mentioned "alkyl group" (specific example group G3) have been replaced. Haloalkyl is sometimes referred to as haloalkyl.

"substituted or unsubstituted alkoxy"

Specific examples of the "substituted or unsubstituted alkoxy group" described in the present specification are groups represented by-O (G3), and G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3. The carbon number of the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, more preferably 1 to 18, unless otherwise stated in the present specification.

"substituted or unsubstituted alkylthio"

Specific examples of the "substituted or unsubstituted alkylthio group" described in the present specification are groups represented by-S (G3), and G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3. The carbon number of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, more preferably 1 to 18, unless otherwise described in the present specification.

"substituted or unsubstituted aryloxy"

Specific examples of the "substituted or unsubstituted aryloxy group" described in the present specification are groups represented by-O (G1), and G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. The number of ring-forming carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise described in the present specification.

"substituted or unsubstituted arylthio"

Specific examples of the "substituted or unsubstituted arylthio group" described in the present specification are groups represented by-S (G1), and G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. The number of ring-forming carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise stated in the specification.

"substituted or unsubstituted trialkylsilyl"

Specific examples of the "trialkylsilyl group" described in the present specification are groups represented by-Si (G3) (G3) (G3), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3. -a plurality of G3 in Si (G3) being the same or different from each other. The carbon number of each alkyl group of the "trialkylsilyl" is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise stated in the present specification.

"substituted or unsubstituted aralkyl"

Specific examples of the "substituted or unsubstituted aralkyl group" described in the present specification are groups represented by- (G3) to (G1), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. Accordingly, the "aralkyl" is a group obtained by replacing a hydrogen atom of the "alkyl" with the "aryl" as a substituent, and is one embodiment of the "substituted alkyl". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group substituted with" unsubstituted aryl group ", and the carbon number of the" unsubstituted aralkyl group "is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise described in the present specification.

Specific examples of the "substituted or unsubstituted aralkyl group" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyltert-butyl, α -naphthylmethyl, 1- α -naphthylethyl, 2- α -naphthylethyl, 1- α -naphthylisopropyl, 2- α -naphthylisopropyl, β -naphthylmethyl, 1- β -naphthylethyl, 2- β -naphthylethyl, 1- β -naphthylisopropyl, and 2- β -naphthylisopropyl.

The substituted or unsubstituted aryl group described in the present specification is preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthracenyl, phenanthryl, pyrenyl,Phenyl, triphenylenyl, fluorenyl, 9' -spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, and the like.

The substituted or unsubstituted heterocyclic group described in the present specification is preferably pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, phenanthrolinyl, carbazolyl (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl or 9-carbazolyl), benzocarbazolyl, azacarbazolyl, diazacarbazolyl, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothienyl, naphthobenzothienyl, azadibenzothienyl, (9-phenyl) carbazolyl ((9-phenyl) carbazol-1-yl, (9-phenyl) carbazol-2-yl, (9-phenyl) carbazol-3-yl or (9-phenyl) carbazol-4-yl), (9-phenyl) phenylcarbazolyl, diphenylcarbazolyl, phenylcarbazolyl, phenyltriazinyl, dibenzotriazinyl, dibenzofuranyl, etc., unless otherwise specified.

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

[ chemical formula 7]

In the present specification, (9-phenyl) carbazolyl is specifically any of the following unless otherwise specified in the present specification.

[ chemical formula 8]

In the general formulae (TEMP-Cz 1) to (TEMP-Cz 9), the bonding position is represented.

In the present specification, dibenzofuranyl and dibenzothiophenyl are specifically any of the following unless otherwise specified in the present specification.

[ chemical formula 9]

In the above general formulae (TEMP-34) to (TEMP-41), the bonding position is represented.

The substituted or unsubstituted alkyl group described in the present specification is preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl or the like unless otherwise specified in the present specification.

"substituted or unsubstituted arylene"

The "substituted or unsubstituted arylene group" described in the present specification is a divalent group derived from the "substituted or unsubstituted aryl group" by removing 1 hydrogen atom from the aryl ring unless otherwise specified. Specific examples of the "substituted or unsubstituted arylene group" (concrete example group G12) include a divalent group derived from the "substituted or unsubstituted aryl group" described in concrete example group G1 by removing 1 hydrogen atom from the aryl ring.

"substituted or unsubstituted divalent heterocyclic radical"

The "substituted or unsubstituted divalent heterocyclic group" described in the present specification is a divalent group derived from the above-mentioned "substituted or unsubstituted heterocyclic group" by removing 1 hydrogen atom from the heterocyclic ring unless otherwise specified. Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (concrete example group G13) include a divalent group derived from the "substituted or unsubstituted heterocyclic group" described in concrete example group G2 by removing 1 hydrogen atom from the heterocycle.

"substituted or unsubstituted alkylene"

The "substituted or unsubstituted alkylene group" described in the present specification is a divalent group derived by removing 1 hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" unless otherwise specified. Specific examples of the "substituted or unsubstituted alkylene group" (concrete example group G14) include a divalent group derived from the "substituted or unsubstituted alkyl group" described in concrete example group G3 by removing 1 hydrogen atom from the alkyl chain.

The substituted or unsubstituted arylene group described in the present specification is preferably any one of the following general formulae (TEMP-42) to (TEMP-68) unless otherwise described in the present specification.

[ chemical formula 10]

[ chemical formula 11]

In the general formulae (TEMP-42) to (TEMP-52), Q ₁ ～Q ₁₀ Each independently is a hydrogen atom or a substituent.

In the above general formulae (TEMP-42) to (TEMP-52), the bonding position is represented.

[ chemical formula 12]

In the general formulae (TEMP-53) to (TEMP-62), Q ₁ ～Q ₁₀ Each independently is a hydrogen atom or a substituent.

Q is as follows ₉ And Q ₁₀ The rings may be formed by bonding to each other via single bonds.

In the above general formulae (TEMP-53) to (TEMP-62), the bonding position is represented.

[ chemical formula 13]

In the general formulae (TEMP-63) to (TEMP-68), Q ₁ ～Q ₈ Each independently is a hydrogen atom or a substituent.

In the above general formulae (TEMP-63) to (TEMP-68), the bonding position is represented.

The substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the following general formulae (TEMP-69) to (TEMP-102) unless otherwise described in the present specification.

[ chemical formula 14]

[ chemical formula 15]

[ chemical formula 16]

In the general formulae (TEMP-69) to (TEMP-82), Q ₁ ～Q ₉ Each independently is a hydrogen atom orA substituent.

[ chemical formula 17]

[ chemical formula 18]

[ chemical formula 19]

[ chemical formula 20]

In the general formulae (TEMP-83) to (TEMP-102), Q ₁ ～Q ₈ Each independently is a hydrogen atom or a substituent.

The above is a description of "substituents described in the present specification".

"case of bonding to form a Ring"

In the present specification, the expression "1 or more groups of 2 or more adjacent to … are bonded to each other to form a substituted or unsubstituted single ring, or are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other" refers to the "1 or more groups of 2 or more adjacent to … are bonded to each other to form a substituted or unsubstituted single ring", the "1 or more groups of 2 or more adjacent to … are bonded to each other to form a substituted or unsubstituted condensed ring", and the "1 or more groups of 2 or more adjacent to … are not bonded to each other".

Hereinafter, description will be made of a case where "1 or more groups of 2 or more adjacent to … are bonded to each other to form a substituted or unsubstituted single ring" and a case where "1 or more groups of 2 or more adjacent to … are bonded to each other to form a substituted or unsubstituted condensed ring" in this specification (hereinafter, these cases are sometimes referred to as "cases of bonding to form a ring"). The case of an anthracene compound represented by the following general formula (TEMP-103) having a parent skeleton as an anthracene ring will be described as an example.

[ chemical formula 21]

For example, in the case of R ₉₂₁ ～R ₉₃₀ In the case where 1 or more groups among "adjacent 2 or more groups are bonded to each other to form a ring", the group consisting of the adjacent 2 groups which are 1 groups means that R ₉₂₁ And R is R ₉₂₂ R is a group of (2) ₉₂₂ And R is R ₉₂₃ R is a group of (2) ₉₂₃ And R is R ₉₂₄ R is a group of (2) ₉₂₄ And R is R ₉₃₀ R is a group of (2) ₉₃₀ And R is R ₉₂₅ R is a group of (2) ₉₂₅ And R is R ₉₂₆ R is a group of (2) ₉₂₆ And R is R ₉₂₇ R is a group of (2) ₉₂₇ And R is R ₉₂₈ R is a group of (2) ₉₂₈ And R is R ₉₂₉ Group(s) of (2), and R ₉₂₉ And R is R ₉₂₁ Is a group of (a).

The "1 or more groups" means that 2 or more groups of the adjacent 2 or more groups can simultaneously form a ring. For example, at R ₉₂₁ And R is R ₉₂₂ Are bonded to each other to form a ring Q _A And at the same time R ₉₂₅ And R is R ₉₂₆ Are bonded to each other to form a ring Q _B In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[ chemical formula 22]

The case where "a group consisting of 2 or more adjacent" forms a ring includes not only the case where bonding occurs in a group consisting of 2 adjacent "as in the foregoing example,also included are cases where bonding occurs from groups of adjacent "3 or more". For example, refer to R ₉₂₁ And R is R ₉₂₂ Are bonded to each other to form a ring Q _A And R is ₉₂₂ And R is R ₉₂₃ Are bonded to each other to form a ring Q _C Is composed of 3 (R ₉₂₁ 、R ₉₂₂ And R is ₉₂₃ ) In the case where the group constituted is bonded to each other to form a ring and condensed to the anthracene skeleton, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following formula (TEMP-105), ring Q _A And ring Q _C Sharing R ₉₂₂ 。

[ chemical formula 23]

In the "single ring" or "condensed ring" formed, the ring formed may have a saturated ring or an unsaturated ring as a structure of the ring itself. Even in the case where "1 group of adjacent 2 groups" forms a "single ring" or "condensed ring", the "single ring" or "condensed ring" may form a saturated ring or an unsaturated ring. For example, the ring Q formed in the above general formula (TEMP-104) _A And ring Q _B Each is a "single ring" or a "fused ring". In addition, the ring Q formed in the above general formula (TEMP-105) _A Ring Q _C Is a "fused ring". Ring Q of the above general formula (TEMP-105) _A And ring Q _C Through ring Q _A And ring Q _C Fused to form a fused ring. Ring Q of the above general formula (TEMP-104) _A In the case of benzene rings, ring Q _A Is a single ring. Ring Q of the above general formula (TEMP-104) _A In the case of naphthalene ring, ring Q _A Is a condensed ring.

"unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocycle. "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.

Specific examples of the aromatic hydrocarbon ring include a structure in which a group specifically exemplified as group G1 is blocked with a hydrogen atom.

Specific examples of the aromatic heterocyclic ring include a structure in which an aromatic heterocyclic group specifically exemplified as group G2 is blocked with a hydrogen atom.

Specific examples of the aliphatic hydrocarbon ring include structures in which a group specifically exemplified as group G6 is blocked with a hydrogen atom.

"forming a ring" means forming a ring from only multiple atoms of the parent skeleton or from multiple atoms of the parent skeleton with 1 or more additional optional elements. For example, R is represented by the above general formula (TEMP-104) ₉₂₁ And R is R ₉₂₂ Ring Q formed by bonding _A Is defined as R ₉₂₁ Carbon atom of bound anthracene skeleton, R ₉₂₂ The carbon atoms of the bound anthracene skeleton form a ring with 1 or more optional elements. As a specific example, R is ₉₂₁ And R is R ₉₂₂ Forming a ring Q _A In the case of (C), R ₉₂₁ Carbon atom of bound anthracene skeleton, R ₉₂₂ Where the carbon atoms of the bound anthracene skeleton and 4 carbon atoms form a monocyclic unsaturated ring, R ₉₂₁ And R is R ₉₂₂ The ring formed is a benzene ring.

Here, the "optional element" is preferably at least 1 element selected from the group consisting of a carbon element, a nitrogen element, an oxygen element, and a sulfur element unless otherwise described in the present specification. In the optional element (for example, in the case of a carbon element or a nitrogen element), the bond which does not form a ring may be blocked by a hydrogen atom or the like, or may be substituted by an "optional substituent" described later. When an optional element other than carbon is included, the ring formed is a heterocyclic ring.

If not otherwise described in the present specification, "1 or more optional elements" constituting a single ring or a condensed ring are preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and still more preferably 3 or more and 5 or less.

In the present specification, unless otherwise stated, the term "monocyclic ring" and the term "condensed ring" are preferably "monocyclic ring".

In the present specification, unless otherwise stated, the "saturated ring" and the "unsaturated ring" are preferably "unsaturated ring".

In the present specification, unless otherwise stated, the "monocyclic ring" is preferably a benzene ring.

In the present specification, unless otherwise stated, the "unsaturated ring" is preferably a benzene ring.

In the case where "1 or more groups of 2 or more adjacent groups" are bonded to each other to form a substituted or unsubstituted single ring "or" are bonded to each other to form a substituted or unsubstituted condensed ring "unless otherwise described in the present specification, it is preferable that 1 or more groups of 2 or more adjacent groups are bonded to each other to form a substituted or unsubstituted" unsaturated ring "formed of a plurality of atoms of a parent skeleton and 1 or more and 15 or less elements selected from at least 1 element selected from the group consisting of carbon element, nitrogen element, oxygen element and sulfur element.

The substituent when the "single ring" or "condensed ring" has a substituent is, for example, an "optional substituent" described later. Specific examples of the substituent when the "single ring" or "condensed ring" has a substituent are the substituents described in the above item of "substituent described in the present specification".

The substituent when the "saturated ring" or "unsaturated ring" has a substituent is, for example, an "optional substituent" described later. Specific examples of the substituent when the "single ring" or "condensed ring" has a substituent are the substituents described in the above item of "substituent described in the present specification".

The above description is for the case of "a substituted or unsubstituted single ring is formed by bonding 1 or more groups of 2 or more adjacent groups" and the case of "a substituted or unsubstituted condensed ring is formed by bonding 1 or more groups of 2 or more adjacent groups" (the case of "a ring is formed by bonding").

Substituents when expressed as "substituted or unsubstituted

In one embodiment of the present specification, the substituent (in the present specification, sometimes referred to as "optional substituent") when expressed as "substituted or unsubstituted" is, for example, an alkyl group having 1 to 50 carbon atoms selected from unsubstituted,

Unsubstituted alkenyl of 2 to 50 carbon atoms,

Unsubstituted alkynyl of 2 to 50 carbon atoms,

Unsubstituted cycloalkyl having 3 to 50 ring-forming carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ )、

-O-(R ₉₀₄ )、

-S-(R ₉₀₅ )、

-N(R ₉₀₆ )(R ₉₀₇ )、

Halogen atom, cyano group, nitro group,

Unsubstituted aryl groups of 6 to 50 ring carbon atoms and

unsubstituted heterocyclic group having 5 to 50 ring members

A group in the group consisting of, and the like,

here, R is ₉₀₁ ～R ₉₀₇ Each independently is

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted cycloalkyl having 3 to 50 ring members,

Substituted or unsubstituted aryl groups having 6 to 50 ring members, or

A heterocyclic group having 5 to 50 ring members which may be substituted or unsubstituted.

at R ₉₀₅ When there are 2 or more, 2 or more R ₉₀₅ Are the same as or different from each other,

At R ₉₀₇ When there are 2 or more, 2 or more R ₉₀₇ The same as or different from each other.

In one embodiment, the substituents described above as "substituted or unsubstituted" are selected from the group consisting of

Alkyl group having 1 to 50 carbon atoms,

Aryl groups having 6 to 50 ring-forming carbon atoms and

heterocyclic groups having 5 to 50 ring members

Groups in the group consisting of.

Alkyl group having 1 to 18 carbon atoms,

Aryl groups having 6 to 18 ring-forming carbon atoms and

heterocyclic groups having 5 to 18 ring-forming atoms

Groups in the group consisting of.

Specific examples of the groups of the above-mentioned optional substituents are specific examples of the substituents described in the item of "substituents described in the present specification" above.

Unless otherwise indicated herein, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring", and preferably form a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, and more preferably form a benzene ring.

The optional substituent may further have a substituent unless otherwise stated in the specification. The substituent further included as an optional substituent is the same as the above optional substituent.

In the present specification, the numerical range indicated by "AA to BB" means a range including the numerical value AA described in the front of "AA to BB" as a lower limit value and the numerical value BB described in the rear of "AA to BB" as an upper limit value.

The organic EL element of the present invention is an organic electroluminescent element having a cathode, an anode, and an organic layer located between the cathode and the anode, wherein the organic layer includes a light-emitting layer, and the organic layer includes a compound represented by formula (1) and a compound represented by formula (2).

Hereinafter, the compound represented by the formula (1) may be referred to as "compound (1)", and the compound represented by the formula (2) may be referred to as "compound (2)".

The composition of the present invention contains a compound represented by formula (1) and a compound represented by formula (2).

< Compound (1) >)

The compound (1) is a compound represented by the following formula (1).

The compound (1) is contained in the organic layer of the organic EL element of the present invention.

In addition, the compound (1) is contained in the composition of the present invention.

[ chemical formula 24]

In the formula (1), the components are as follows,

N ^＊ is a central nitrogen atom.

R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ Each independently is

A hydrogen atom,

Halogen atom,

Cyano group,

Nitro group,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

Substituted or unsubstituted cycloalkyl having 3 to 50 ring members,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ) A group shown,

-O-(R ₉₀₄ ) A group shown,

-S-(R ₉₀₅ ) A group shown,

-N(R ₉₀₆ )(R ₉₀₇ ) A group shown,

Substituted or unsubstituted aryl groups having 6 to 50 ring members, or

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

R ₉₀₁ ～R ₉₀₇ each independently is

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted cycloalkyl having 3 to 50 ring members,

Substituted or unsubstituted aryl groups having 6 to 50 ring members, or

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

R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ Each independently is preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming carbon atoms, more preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, still more preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, still more preferably a hydrogen atom.

R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ The details of the halogen atom are the same as those described in the above description of the substituent "described in the present specification, and are preferably fluorine atoms.

R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ The details of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms are the same as those described in the above description of the "substituent" described in the present specification.

R ¹ ～R ⁶ And R is ¹¹ ～R ¹⁴ The unsubstituted alkyl group represented is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group, more preferably a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group, and still more preferably a methyl group or a tert-butyl group.

R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ Details of the substituted or unsubstituted alkenyl group having 2 to 50 ring-forming carbon atoms are the same as those described in the above description of the substituent group described in the present specification.

R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ The details of the substituted or unsubstituted alkynyl group having 2 to 50 ring-forming carbon atoms are the same as those described in the above description of the substituent group described in the present specification.

R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ Details of the substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms shown above and the references described hereinabove in the specificationThe description of the terms of the "substituent" is the same.

R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ The unsubstituted cycloalkyl group represented is preferably cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, or 2-norbornyl, more preferably cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl, and still more preferably cyclopentyl or cyclohexyl.

R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ Represented by the above-mentioned-Si (R) ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ) above-mentioned-O- (R) ₉₀₄ ) The radicals indicated, -S- (R) ₉₀₅ ) The radicals shown, and-N (R ₉₀₆ )(R ₉₀₇ ) The details of the groups shown are the same as those described in the "substituents described in the present specification".

R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ The details of the substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms are the same as those described in the "substituents described in the present specification".

R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ The unsubstituted aryl group represented is preferably a phenyl group, a biphenyl group, a naphthyl group, or a phenanthryl group, more preferably a phenyl group, a biphenyl group, or a naphthyl group, and still more preferably a phenyl group.

R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ The details of the substituted or unsubstituted heterocyclic group having 5 to 50 ring members are the same as those described in the "substituents described in the present specification".

R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ The unsubstituted heterocyclic group represented above is preferably dibenzofuranyl or dibenzothienyl.

R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ May be a hydrogen atom.

n is 0 or 1.

In one embodiment of the invention, n is preferably 0.

Wherein,,

when n is 0, the number of the n-type organic electroluminescent element,

when n is 1, the number of the n-type organic electroluminescent element,

In one embodiment of the invention, R is preferably ¹ Or R is ⁸ Is a single bond to One, more preferably R ⁸ Is a single bond to the ene.

X ¹ Is an oxygen atom or a sulfur atom.

In one aspect of the invention, X ¹ Preferably an oxygen atom.

In another aspect of the invention, X ¹ Sulfur atoms are preferred.

Ar ¹ And Ar is a group ² Details of the substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms represented by the above description and "substitution as described in the present specificationThe description of the "base" is the same.

Ar ¹ And Ar is a group ² The unsubstituted aryl group represented is preferably a phenyl group, a biphenyl group, a naphthyl group, or a phenanthryl group, more preferably a phenyl group, a biphenyl group, or a naphthyl group, and still more preferably a phenyl group.

Ar ¹ And Ar is a group ² The details of the substituted or unsubstituted heterocyclic group having 5 to 50 ring members are the same as those described in the "substituents described in the present specification".

Ar ¹ And Ar is a group ² The unsubstituted heterocyclic group represented above is preferably dibenzofuranyl or dibenzothienyl.

Ar ¹ And Ar is a group ² Each independently is preferably a group represented by any one of the following formulas (1-a) to (1-f).

Wherein in Ar ¹ In the case of the following formula (1-a), L2 is a single bond,

in Ar ² In the case of the following formula (1-a), L ³ Is a single bond,

in Ar ¹ When the compound is represented by any one of the following formulas (1-b) to (1-f), L ² Is a single bond or an unsubstituted arylene group having 6 to 30 ring members,

in Ar ² When the compound is represented by any one of the following formulas (1-b) to (1-f), L ³ Is a single bond or an unsubstituted arylene group having 6 to 30 ring members.

[ chemical formula 25]

In the formula (1-a),

R ⁴¹ ～R ⁴⁵ each independently represents a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms,

represents a central nitrogen atom N ^＊ Is used for the bonding position of the substrate.

R ⁴¹ ～R ⁴⁵ The unsubstituted alkyl group having 1 to 6 carbon atoms is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl or isobutylThe group, sec-butyl group, or tert-butyl group is more preferably methyl group, ethyl group, isopropyl group, or tert-butyl group, and still more preferably methyl group or tert-butyl group.

R ⁴¹ ～R ⁴⁵ May be a hydrogen atom.

[ chemical formula 26]

In the formula (1-b),

R ⁵¹ ～R ⁵⁸ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms.

Wherein,,

selected from the group consisting of R ⁵¹ ～R ⁵⁸ 1 of them is a single bond to the f,

selected from R other than the single bonds mentioned ⁵¹ ～R ⁵⁸ The adjacent 2 of the two are not bonded to each other and thus form a ring structure.

Representation and L ² Or L ³ Is used for the bonding position of the substrate.

Wherein,,

at L ² When a single bond is used as Ar ¹ The radicals of the formula (1-b) are represented by the general formula (I) and the central nitrogen atom N ^＊ Is used for the bonding position of the (c) and (d),

at L ³ When a single bond is used as Ar ² The radicals of the formula (1-b) are represented by the general formula (I) and the central nitrogen atom N ^＊ Is used for the bonding position of the substrate.

R ⁵¹ ～R ⁵⁸ Details of the unsubstituted alkyl group having 1 to 6 carbon atoms shown above, preferred examples thereof, and the specific meaning of R ⁴¹ ～R ⁴⁵ The same applies to the description of (2).

R ⁵¹ ～R ⁵⁸ The unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by the above formula is preferably phenyl, biphenyl, or naphthyl, more preferably phenyl or naphthyl, and still more preferably phenyl.

In one embodiment of the present invention, it is preferable that R is selected from ⁵¹ 、R ⁵⁴ 、R ⁵⁵ And R is ⁵⁸ 1 of them is a single bond to the f bond.

R ⁵¹ ～R ⁵⁸ May be a hydrogen atom.

[ chemical formula 27]

In the formula (1-c),

R ⁶¹ ～R ⁷⁰ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms.

Wherein,,

selected from the group consisting of R ⁶¹ ～R ⁷⁰ 1 of them is a single bond to g,

selected from R other than the single bonds mentioned ⁶¹ ～R ⁷⁰ The adjacent 2 of the two are not bonded to each other and thus form a ring structure.

Wherein,,

at L ² When a single bond is used as Ar ¹ The radicals of the formula (1-c) are represented by the general formula (I) and the central nitrogen atom N ^＊ Is used for the bonding position of the (c) and (d),

at L ³ When a single bond is used as Ar ² The radicals of the formula (1-c) are represented by the general formula (I) and the central nitrogen atom N ^＊ Is used for the bonding position of the substrate.

R ⁶¹ ～R ⁷⁰ Details of the unsubstituted alkyl group having 1 to 6 carbon atoms shown above, preferred examples thereof, and the specific meaning of R ⁴¹ ～R ⁴⁵ The same applies to the description of (2).

R ⁶¹ ～R ⁷⁰ The unsubstituted aryl group having 6 to 12 carbon atoms in the ring and R are as defined above ⁵¹ ～R ⁵⁸ The description is the same, and preferably the groups and the like are the same.

In one embodiment of the invention, it is preferably selected from R ⁶¹ 、R ⁶² And R is ⁷⁰ 1 of them is a bond with gA single bond, more preferably selected from R ⁶² And R is ⁷⁰ Wherein 1 is a single bond to g, more preferably R ⁷⁰ Is a single bond to the onium g.

R is not a single bond to g ⁶¹ ～R ⁷⁰ May be a hydrogen atom.

[ chemical formula 28]

In the formula (1-d),

R ⁸¹ ～R ⁹² each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms.

Wherein,,

selected from the group consisting of R ⁸¹ ～R ⁹² 1 of them is a single bond to an oh,

selected from R other than the single bonds mentioned ⁸¹ ～R ⁹² The adjacent 2 of the two are not bonded to each other and thus form a ring structure.

Wherein,,

at L ² When a single bond is used as Ar ¹ The radicals of the formula (1-d) are represented by the general formula (I) and the central nitrogen atom N ^＊ Is used for the bonding position of the (c) and (d),

at L ³ When a single bond is used as Ar ² The radicals of the formula (1-d) are represented by the general formula (I) and the central nitrogen atom N ^＊ Is used for the bonding position of the substrate.

R ⁸¹ ～R ⁹² Details of the unsubstituted alkyl group having 1 to 6 carbon atoms shown above, preferred examples thereof, and the specific meaning of R ⁴¹ ～R ⁴⁵ The same applies to the description of (2).

R ⁸¹ ～R ⁹² The unsubstituted aryl group having 6 to 12 carbon atoms in the ring and R are as defined above ⁵¹ ～R ⁵⁸ The description is the same, and preferably the groups and the like are the same.

In one of the present inventionIn the scheme, R ⁸¹ Is a single bond to Oh, in another embodiment R ⁸² Is a single bond to zh.

R is not a single bond to Oh ⁸¹ ～R ⁹² May be a hydrogen atom.

[ chemical formula 29]

In the formula (1-e),

R ¹⁰¹ ～R ¹⁰⁸ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 13 ring-forming carbon atoms.

X ³ Is an oxygen atom, a sulfur atom, NR ^c Or CR ^d R ^e ，

R ^c Is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 13 ring-forming atoms,

R ^d And R is ^e Each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, R ^d And R is R ^e May be bonded to each other to form a substituted or unsubstituted ring.

Wherein,,

selected from the group consisting of R ¹⁰¹ ～R ¹⁰⁸ And R is ^c 1 of them is a single bond to the O/I bond,

selected from R other than the single bonds mentioned ¹⁰¹ ～R ¹⁰⁸ Adjacent ones of the two groups may be bonded to each other to form a substituted or unsubstituted benzene ring.

Wherein,,

at L ² When a single bond is used as Ar ¹ The radicals of the formula (1-e)Meaning N with the central nitrogen atom ^＊ Is used for the bonding position of the (c) and (d),

at L ³ When a single bond is used as Ar ² The radicals of the formula (1-e) are represented by the general formula (I) and the central nitrogen atom N ^＊ Is used for the bonding position of the substrate.

R ¹⁰¹ ～R ¹⁰⁸ Preferably a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, more preferably a hydrogen atom.

R ¹⁰¹ ～R ¹⁰⁸ Details of the unsubstituted alkyl group having 1 to 6 carbon atoms shown above, preferred examples thereof, and the specific meaning of R ⁴¹ ～R ⁴⁵ The same applies to the description of (2).

R ¹⁰¹ ～R ¹⁰⁸ Details and preferred examples of the unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by the above formula are as described in R ⁵¹ ～R ⁵⁸ The description is the same, and preferably the groups and the like are the same.

R ¹⁰¹ ～R ¹⁰⁸ The unsubstituted aromatic heterocyclic group having 5 to 13 ring members is preferably a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a benzofuryl group, a benzothienyl group (benzothienyl group), a carbazolyl group, a dibenzofuryl group, or a dibenzothienyl group (dibenzothienyl group).

X ³ Preferably oxygen atom, NR ^c Or CR ^d R ^e 。

R ^c 、R ^d And R is ^e Preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms.

R ^c 、R ^d And R is ^e The unsubstituted alkyl group having 1 to 6 carbon atoms represented is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group, more preferably a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group, and still more preferably a methyl group or a tert-butyl group.

R ^c 、R ^d And R is ^e The unsubstituted aryl group represented by the above is preferably phenyl, biphenyl, or naphthylMore preferably phenyl.

R ^c The unsubstituted aromatic heterocyclic group represented is preferably a pyridyl group or a quinazolinyl group.

From R ^d And R is ^e The unsubstituted monocyclic ring formed is, for example, a benzene ring, a cyclopentane ring, a cyclohexane ring.

From R ^d And R is ^e The unsubstituted condensed ring formed is, for example, a naphthalene ring or an anthracene ring.

In addition, at R ^d And R is R ^e In the case of bonding to each other to form an unsubstituted monocyclic ring or an unsubstituted condensed ring, R ^d And R is ^e Together with the fluorene skeleton to which they are bonded form a ring, for example, a spirobifluorene skeleton, spiro [ 9H-fluorene-9, 1' -cyclopentane can be formed]And (3) a framework.

R is not a single bond to pi ¹⁰¹ ～R ¹⁰⁸ May be a hydrogen atom.

[ chemical formula 30]

In the formula (1-f),

R ¹¹¹ ～R ¹¹⁵ each independently represents a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted phenyl group,

R ¹²¹ ～R ¹²⁵ and R is ¹³¹ ～R ¹³⁵ Each independently represents a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms.

Wherein,,

selected from the group consisting of R ¹¹¹ ～R ¹¹⁵ 1 of them is a single bond to j,

selected from the group consisting of R ¹¹¹ ～R ¹¹⁵ The other 1 of them is a single bond to k,

selected from R other than the single bonds mentioned ¹¹¹ ～R ¹¹⁵ The adjacent 2 of the two are not bonded to each other and thus do not form a ring structure,

selected from R ¹²¹ ～R ¹²⁵ And R is ¹³¹ ～R ¹³⁵ Adjacent 2 of (a)To bond with each other to form a substituted or unsubstituted benzene ring.

Wherein,,

at L ² When a single bond is used as Ar ¹ The radicals of the formula (1-f) are represented by the general formula (I) and the central nitrogen atom N ^＊ Is used for the bonding position of the (c) and (d),

at L ³ When a single bond is used as Ar ² The radicals of the formula (1-f) are represented by the general formula (I) and the central nitrogen atom N ^＊ Is used for the bonding position of the substrate.

R ¹¹¹ ～R ¹¹⁵ 、R ¹²¹ ～R ¹²⁵ And R is ¹³¹ ～R ¹³⁵ Details of the unsubstituted alkyl group having 1 to 6 carbon atoms shown above, preferred examples thereof, and the specific meaning of R ⁴¹ ～R ⁴⁵ The same applies to the description of (2).

In one embodiment of the invention, R is selected from ¹²¹ ～R ¹²⁵ Is bonded to each other to form a substituted or unsubstituted benzene ring. In another aspect of the invention, R is selected from ¹²¹ ～R ¹²⁵ The adjacent 2 of the two are not bonded to each other and thus do not form a ring structure.

In one embodiment of the invention, R is selected from ¹³¹ ～R ¹³⁵ Is bonded to each other to form a substituted or unsubstituted benzene ring. In another aspect of the invention, R is selected from ¹³¹ ～R ¹³⁵ The adjacent 2 of the two are not bonded to each other and thus do not form a ring structure.

R is not a single bond to both Ivj and Ivk ¹¹¹ ～R ¹¹⁵ All can be hydrogen atom, R ¹²¹ ～R ¹²⁵ All can be hydrogen atom, R ¹³¹ ～R ¹³⁵ May be a hydrogen atom.

L ¹ ～L ³ Each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming carbon atoms.

L ¹ ～L ³ Preferably a single bond, a substituted or unsubstituted arylene group having 6 to 12 ring members, orThe substituted or unsubstituted divalent heterocyclic group having 5 to 13 ring-forming atoms is more preferably a single bond or a substituted or unsubstituted arylene group having 6 to 12 ring-forming carbon atoms.

L ¹ ～L ³ Details of the unsubstituted arylene group having 6 to 30 ring members are the same as those described in the above description of the "substituent described in the present specification".

L ¹ ～L ³ The unsubstituted arylene group having 6 to 30 ring members is preferably phenylene, biphenylene, terphenylene or naphthylene.

L ¹ ～L ³ The details of the substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring members are the same as those described in the above description of the "substituent described in the present specification".

L ¹ Preferably a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group, more preferably a substituted or unsubstituted phenylene group, further preferably an o-phenylene group, or a p-phenylene group.

L ² And L ³ Each independently is preferably a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group, more preferably a single bond, or a substituted or unsubstituted phenylene group, further preferably an unsubstituted phenylene group, still further preferably an o-phenylene group, or a p-phenylene group.

In one embodiment of the present invention, the compound (1) is preferably a compound represented by any one of the following formulas (1A) to (1C), more preferably a compound represented by the following formula (1C).

[ chemical formula 31]

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

N ^＊、R ¹ ～R ⁸ 、R ¹¹ ～R ¹⁴ 、X ¹ 、Ar ¹ 、Ar ² and L ¹ ～L ³ The definition is the same as in formula (1).

Wherein,,

when the compound represented by the formula (1) is represented by the formula (1A), R is selected from ³ ～R ⁸ And R is ¹¹ ～R ¹⁴ 1 of them is a single bond to 1,

when the compound represented by the formula (1) is represented by the formula (1B), R is selected from ¹ 、R ⁴ ～R ⁸ And R is ¹¹ ～R ¹⁴ 1 of them is a single bond to an am,

when the compound represented by the formula (1) is represented by the formula (1C), R is selected from ¹ 、R ² 、R ⁵ ～R ⁸ And R is ¹¹ ～R ¹⁴ 1 of them is a single bond to an n.

In one embodiment of the present invention, the compound represented by formula (1) is preferably a compound represented by formula (1 c).

[ chemical formula 32]

In the formula (1 c), the amino acid sequence,

N ^＊、R ¹ 、R ² 、R ⁵ ～R ⁷ 、R ¹¹ ～R ¹⁴ 、X ¹ 、Ar ¹ 、Ar ² and L ¹ ～L ³ The definition is the same as in formula (1).

As described above, the term "hydrogen atom" used in the present specification includes protium atom, deuterium atom, and tritium atom. Thus, compound (1) may also contain deuterium atoms of natural origin.

In addition, deuterium atoms can be intentionally introduced into the compound (1) by using a deuterated compound as part or all of the starting compound. Thus, in one embodiment of the invention, compound (1) comprises at least 1 deuterium atom. That is, the compound (1) may be a compound represented by the formula (1), at least one of the hydrogen atoms contained in the compound being a deuterium atom.

At least one hydrogen atom selected from the following hydrogen atoms may be a deuterium atom. Hereinafter, "substituted or unsubstituted", carbon number and atomic number are omitted.

R of formula (1) is not a single bond to a, b, c and d ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ A hydrogen atom represented by any one of the above;

r in formula (1) is not a single bond to a, b, c and d ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ Any one of which is alkyl, alkenyl, alkynyl, cycloalkyl, -Si (R) ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ) The radicals indicated, -O- (R) ₉₀₄ ) The radicals indicated, -S- (R) ₉₀₅ ) The radicals indicated, -N (R ₉₀₆ )(R ₉₀₇ ) In the case of the radicals, aryl or heterocyclic radicals indicated, the alkyl radicals, the alkynyl radicals, the cycloalkyl radicals, the-Si (R) ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ) A group of the formula, the-O- (R) ₉₀₄ ) The radicals shown, the-S- (R) ₉₀₅ ) A group represented by the formula-N (R ₉₀₆ )(R ₉₀₇ ) A hydrogen atom of the group shown, the aryl group or the heterocyclic group;

ar of formula (1) ¹ And Ar is a group ² In the case of an aryl group or a heterocyclic group, the aryl group or the heterocyclic group has a hydrogen atom;

l in formula (1) ¹ ～L ³ In the case of an arylene group or a divalent heterocyclic group, the arylene group or the divalent heterocyclic group has a hydrogen atom.

The deuteration rate of the compound (1) depends on the deuteration rate of the raw material compound used. Even if a raw material having a predetermined deuteration rate is used, the protium isotope may be contained in a constant ratio from a natural source. Accordingly, the following schemes of deuteration rates of the inventive compounds include ratios in which the natural-derived trace isotopes are considered, relative to ratios obtained by counting only the number of deuterium atoms represented by the chemical formula.

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

The compound (1) may be a mixture containing a deuterated compound and a non-deuterated compound, a mixture of 2 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, still more preferably 10% or more, still more preferably 50% or more, and less than 100%.

The ratio of the number of deuterium atoms in the compound (1) to the total number of hydrogen atoms is preferably 1% or more, more preferably 3% or more, still more preferably 5% or more, still more preferably 10% or more and 100% or less.

In the case where the "substituted or unsubstituted XX group" contained in the above-mentioned definition of each formula is a substituted XX group, details of the substituent are the same as those described in the description of the "substituted or unsubstituted" substituent ", and are preferably an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring atoms, or an aromatic heterocyclic group having 5 to 13 ring atoms, more preferably an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 12 ring atoms. The details of each group are as described above.

The compound (1) can be easily produced by those skilled in the art with reference to the following synthesis examples and known synthesis methods.

Specific examples of the compound (1) are shown below, and are not limited to the following exemplified compounds.

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

[ chemical formula 33]

[ chemical formula 34]

[ chemical formula 35]

[ chemical formula 36]

[ chemical formula 37]

[ chemical formula 38]

[ chemical formula 39]

[ chemical formula 40]

[ chemical formula 41]

[ chemical formula 42]

[ chemical formula 43]

[ chemical formula 44]

[ chemical formula 45]

[ chemical formula 46]

[ chemical formula 47]

[ chemical formula 48]

[ chemical formula 49]

[ chemical formula 50]

[ chemical formula 51]

[ chemical formula 52]

[ chemical formula 53]

[ chemical formula 54]

[ chemical formula 55]

[ chemical formula 56]

[ chemical formula 57]

[ chemical formula 58]

[ chemical formula 59]

[ chemical formula 60]

[ chemical formula 61]

[ chemical formula 62]

[ chemical formula 63]

[ chemical formula 64]

[ chemical formula 65]

[ chemical formula 66]

[ chemical formula 67]

[ chemical formula 68]

[ chemical formula 69]

[ chemical formula 70]

[ chemical formula 71]

[ chemical formula 72]

[ chemical formula 73]

[ chemical formula 74]

[ chemical formula 75]

[ chemical formula 76]

[ chemical formula 77]

[ chemical formula 78]

[ chemical formula 79]

[ chemical formula 80]

[ chemical formula 81]

[ chemical formula 82]

[ chemical formula 83]

[ chemical formula 84]

[ chemical formula 85]

[ chemical formula 86]

[ chemical formula 87]

[ chemical formula 88]

[ chemical formula 89]

[ chemical formula 90]

[ chemical formula 91]

[ chemical formula 92]

[ chemical formula 93]

[ chemical formula 94]

[ chemical formula 95]

[ chemical formula 96]

[ chemical formula 97]

[ chemical formula 98]

[ chemical formula 99]

[ chemical formula 100]

[ chemical formula 101]

[ chemical formula 102]

[ chemical formula 103]

[ chemical formula 104]

[ chemical formula 105]

[ chemical formula 106]

[ chemical formula 107]

[ chemical formula 108]

[ chemical formula 109]

[ chemical formula 110]

[ chemical formula 111]

[ chemical formula 112]

[ chemical formula 113]

[ chemical formula 114]

[ chemical formula 115]

[ chemical formula 116]

[ chemistry 117]

[ chemical formula 118]

[ chemical formula 119]

[ chemical formula 120]

[ chemical formula 121]

[ chemical formula 122]

[ chemical formula 123]

[ chemical formula 124]

[ chemical formula 125]

[ chemical formula 126]

[ chemical formula 127]

[ chemical formula 128]

[ chemical formula 129]

[ chemistry 130]

[ chemical formula 131]

[ chemical formula 132]

[ chemical formula 133]

[ chemical formula 134]

[ chemical formula 135]

[ chemical formula 136]

[ chemical formula 137]

[ chemical formula 138]

[ chemical formula 139]

[ chemical formula 140]

[ chemical formula 141]

[ chemical formula 142]

[ chemical formula 143]

[ chemical formula 144]

[ chemical formula 145]

[ chemical formula 146]

[ chemical formula 147]

[ chemical formula 148]

[ chemical formula 149]

[ chemical formula 150]

[ chemical formula 151]

[ chemical formula 152]

[ chemical formula 153]

[ chemical formula 154]

[ chemical formula 155]

[ chemical formula 156]

[ chemical formula 157]

[ chemical formula 158]

[ chemical formula 159]

[ chemical formula 160]

[ chemical formula 161]

[ chemical formula 162]

[ chemical formula 163]

[ chemical formula 164]

[ chemical formula 165]

[ chemical formula 166]

[ chemical formula 167]

[ chemical formula 168]

[ chemical formula 169]

[ chemical formula 170]

[ chemical formula 171]

[ chemical formula 172]

[ chemical formula 173]

[ chemical formula 174]

[ chemical formula 175]

[ chemical formula 176]

[ chemical formula 177]

[ chemical formula 178]

[ chemical formula 179]

[ chemical formula 180]

[ chemical formula 181]

[ chemical formula 182]

[ chemical formula 183]

[ chemical formula 184]

[ chemical formula 185]

[ chemical formula 186]

[ chemical formula 187]

[ chemical formula 188]

[ chemical formula 189]

[ chemical formula 190]

[ chemical formula 191]

[ chemical formula 192]

[ chemical formula 193]

[ chemical formula 194]

[ chemical formula 195]

[ chemical formula 196]

[ chemical formula 197]

[ chemical formula 198]

[ chemical formula 199]

[ chemical formula 200]

[ chemical formula 201]

[ chemical formula 202]

[ chemical formula 203]

[ chemical formula 204]

[ chemical formula 205]

[ chemical formula 206]

[ chemical formula 207]

[ chemical formula 208]

[ chemical formula 209]

[ chemical formula 210]

[ chemical formula 211]

[ chemical formula 212]

[ chemical formula 213]

[ chemical formula 214]

[ chemical formula 215]

[ chemical formula 216]

[ chemical formula 217]

[ chemical formula 218]

[ chemical formula 219]

[ chemical formula 220]

[ chemical formula 221]

[ chemical formula 222]

[ chemical formula 223]

[ chemical formula 224]

[ chemical formula 225]

[ chemical formula 226]

[ chemical formula 227]

[ chemical formula 228]

[ chemical formula 229]

[ chemical formula 230]

[ chemical formula 231]

[ chemical formula 232]

[ chemical formula 233]

[ chemical formula 234]

[ chemical formula 235]

[ chemical formula 236]

[ chemical formula 237]

[ chemical formula 238]

[ chemical formula 239]

[ chemical formula 240]

[ chemical formula 241]

[ chemical formula 242]

[ chemical formula 243]

[ chemical formula 244]

[ chemical formula 245]

[ chemical formula 246]

[ chemical formula 247]

[ chemical formula 248]

[ chemical formula 249]

[ chemical formula 250]

[ chemical formula 251]

[ chemical formula 252]

[ chemistry 253]

[ chemical formula 254]

[ chemical formula 255]

[ chemical formula 256]

[ chemistry type 257]

[ chemical formula 258]

[ chemical formula 259]

[ chemical formula 260]

[ chemical formula 261]

[ chemical formula 262]

[ chemical formula 263]

[ chemical formula 264]

[ chemical formula 265]

[ chemical formula 266]

[ chemical formula 267]

[ chemical formula 268]

[ chemical formula 269]

[ chemical formula 270]

[ chemical formula 271]

[ chemical formula 272]

[ chemical formula 273]

[ chemical formula 274]

[ chemical formula 275]

[ chemical formula 276]

[ chemical formula 277]

[ chemical formula 278]

[ chemical formula 279]

[ chemical formula 280]

[ chemical formula 281]

[ chemical formula 282]

[ chemical formula 283]

[ chemical formula 284]

[ chemical formula 285]

[ chemical formula 286]

[ chemical formula 287]

[ chemical formula 288]

[ chemical formula 289]

[ chemical formula 290]

[ chemical formula 291]

[ chemical formula 292]

Chemical formula 293

[ chemical formula 294]

[ chemical formula 295]

[ chemistry 296]

[ chemical formula 297]

[ chemical formula 298]

[ chemical formula 299]

[ chemical formula 300]

[ chemical formula 301]

[ chemical formula 302]

[ chemical formula 303]

[ chemical formula 304]

[ chemical formula 305]

[ chemical formula 306]

[ chemical formula 307]

[ chemical formula 308]

[ chemical formula 309]

[ chemical formula 310]

[ chemical formula 311]

[ chemical formula 312]

[ chemical formula 313]

[ chemical formula 314]

[ chemical formula 315]

[ chemical formula 316]

[ chemical formula 317]

[ chemical formula 318]

[ chemical formula 319]

[ chemical formula 320]

[ chemical formula 321]

[ chemical formula 322]

/>

[ chemical formula 323]

[ chemical formula 324]

[ chemical formula 325]

[ chemical formula 326]

[ chemical formula 327]

[ chemical formula 328]

[ chemistry 329]

[ chemical formula 330]

[ chemistry 331]

[ chemical formula 332]

[ chemical formula 333]

[ chemical formula 334]

[ chemical formula 335]

[ chemical formula 336]

[ chemical formula 337]

[ chemical formula 338]

[ chemical formula 339]

[ chemical formula 340]

[ chemical formula 341]

[ chemical formula 342]

[ chemical formula 343]

[ chemical formula 344]

[ chemical formula 345]

[ chemical formula 346]

[ chemical formula 347]

[ chemical formula 348]

[ chemical formula 349]

[ chemical formula 350]

[ chemical formula 351]

[ chemical formula 352]

[ chemical formula 353]

[ chemical formula 354]

[ chemical formula 355]

[ chemical formula 356]

[ chemistry 357]

[ chemical formula 358]

[ chemical formula 359]

[ chemical formula 360]

[ chemical formula 361]

[ chemical formula 362]

[ chemical formula 363]

[ chemical formula 364]

[ chemical formula 365]

[ chemical formula 366]

[ chemical formula 367]

[ chemical formula 368]

[ chemical formula 369]

[ chemical formula 370]

[ chemical formula 371]

[ chemical formula 372]

[ chemical formula 373]

[ chemical formula 374]

[ chemical formula 375]

[ chemical formula 376]

[ chemical formula 377]

[ chemical formula 378]

[ chemical formula 379]

[ chemical formula 380]

[ chemical formula 381]

[ chemical formula 382]

[ chemical formula 383]

[ chemical formula 384]

[ chemical formula 385]

[ chemical formula 386]

[ chemical formula 387]

[ chemical formula 388]

[ chemical formula 389]

[ chemical formula 390]

[ chemical formula 391]

[ chemical formula 392]

[ chemical formula 393]

[ chemical formula 394]

[ chemical formula 395]

[ chemical formula 396]

[ chemical formula 397]

[ chemical formula 398]

[ chemical formula 399]

[ chemical formula 400]

[ chemical formula 401]

/>

[ chemical formula 402]

[ chemical formula 403]

[ chemical formula 404]

[ chemical formula 405]

[ chemical formula 406]

[ chemical formula 407]

[ chemical formula 408]

[ chemical formula 409]

[ chemical formula 410]

[ chemical formula 411]

/>

[ chemical formula 412]

[ chemical formula 413]

[ chemical formula 414]

[ chemical formula 415]

[ chemical formula 416]

[ chemical formula 417]

[ chemical formula 418]

[ chemical formula 419]

[ chemical formula 420]

[ chemical formula 421]

[ chemical formula 422]

[ chemistry 423]

[ chemical formula 424]

[ chemical formula 425]

[ chemical formula 426]

[ chemical formula 427]

[ chemical formula 428]

[ chemical formula 429]

[ chemical formula 430]

[ chemical formula 431]

[ chemical formula 432]

[ chemical formula 433]

[ chemical formula 434]

[ chemistry 435]

[ chemical formula 436]

[ chemical formula 437]

[ chemical formula 438]

[ chemistry 439]

[ chemical formula 440]

[ chemical formula 441]

[ chemical formula 442]

[ chemical formula 443]

[ chemical formula 444]

[ chemical formula 445]

[ chemical formula 446]

[ chemical formula 447]

[ chemical formula 448]

[ chemical formula 449]

[ chemical formula 450]

[ chemical formula 451]

[ chemical formula 452]

[ chemical formula 453]

[ chemical formula 454]

[ chemical formula 455]

[ chemical formula 456]

/>

[ chemistry formula 457]

[ chemical formula 458]

[ chemical formula 459]

[ chemical formula 460]

[ chemical formula 461]

[ chemical formula 462]

[ chemical formula 463]

[ chemical formula 464]

[ chemical formula 465]

[ chemical formula 466]

[ chemical formula 467]

[ chemistry type 468]

[ chemical formula 469]

[ chemical formula 470]

[ chemistry 471]

[ chemical formula 472]

[ chemical formula 473]

[ chemical formula 474]

[ chemical formula 475]

[ chemical formula 476]

[ chemical formula 477]

[ chemical formula 478]

[ chemical formula 479]

[ chemical formula 480]

[ chemical formula 481]

[ chemical formula 482]

[ chemical formula 483]

[ chemical formula 484]

[ chemical formula 485]

[ chemical formula 486]

[ chemical formula 487]

[ chemical formula 488]

[ chemical formula 489]

[ chemical formula 490]

[ chemical formula 491]

[ chemical formula 492]

[ chemical formula 493]

[ chemical formula 494]

[ chemical formula 495]

[ chemical formula 496]

[ chemical formula 497]

[ chemical formula 498]

[ chemical formula 499]

[ chemical formula 500]

[ chemical formula 501]

[ chemical formula 502]

[ chemical formula 503]

/>

[ chemical formula 504]

[ chemical formula 505]

[ chemical formula 506]

[ chemical formula 507]

[ chemical formula 508]

[ chemical formula 509]

[ chemical formula 510]

[ chemical formula 511]

[ chemical formula 512]

[ chemical formula 513]

[ chemical formula 514]

[ chemical formula 515]

[ chemical formula 516]

[ chemical formula 517]

/>

[ chemical formula 518]

[ chemical formula 519]

[ chemical formula 520]

[ chemical formula 521]

[ chemical formula 522]

[ chemical formula 523]

[ chemical formula 524]

[ chemical formula 525]

[ chemical formula 526]

[ chemical formula 527]

[ chemical formula 528]

[ chemical formula 529]

[ chemical formula 530]

[ chemical formula 531]

[ chemical formula 532]

[ chemical formula 533]

[ chemical formula 534]

[ chemical formula 535]

[ chemical formula 536]

[ chemical formula 537]

[ chemical formula 538]

[ chemical formula 539]

[ chemical formula 540]

[ chemical formula 541]

[ chemical formula 542]

[ chemical formula 543]

[ chemical formula 544]

[ chemical formula 545]

[ chemical formula 546]

[ chemical formula 547]

[ chemistry 548]

[ chemical formula 549]

[ chemical formula 550]

[ chemical formula 551]

[ chemical formula 552]

[ chemical formula 553]

[ chemistry 554]

[ chemical formula 555]

[ chemical formula 556]

[ chemical formula 557]

[ chemical formula 558]

[ chemical formula 559]

[ chemical formula 560]

[ chemical formula 561]

[ chemical formula 562]

[ chemical formula 563]

[ chemical formula 564]

[ chemical formula 565]

[ chemical formula 566]

[ chemical formula 567]

[ chemical formula 568]

[ chemical formula 569]

[ chemical formula 570]

[ chemical formula 571]

[ chemical formula 572]

[ chemistry 573]

[ chemical formula 574]

[ chemical formula 575]

[ chemical formula 576]

[ chemical formula 577]

[ chemical formula 578]

[ chemical formula 579]

[ chemical formula 580]

[ chemical formula 581]

[ chemical formula 582]

[ chemical formula 583]

[ chemical formula 584]

[ chemical formula 585]

[ chemical formula 586]

[ chemical formula 587]

[ chemical formula 588]

[ chemical formula 589]

[ chemical formula 590]

[ chemical formula 591]

[ chemical formula 592]

[ chemical formula 593]

[ chemical formula 594]

[ chemical formula 595]

[ chemical formula 596]

[ chemical formula 597]

[ chemical formula 598]

[ chemical formula 599]

[ chemical formula 600]

[ chemical formula 601]

[ chemical formula 602]

[ chemical formula 603]

[ chemical formula 604]

[ chemical formula 605]

[ chemical formula 606]

[ chemical formula 607]

[ chemical formula 608]

[ chemical formula 609]

[ chemical formula 610]

[ chemical formula 611]

[ chemical formula 612]

[ chemical formula 613]

[ chemical formula 614]

[ chemical formula 615]

[ chemical formula 616]

[ chemical formula 617]

[ chemical formula 618]

[ chemical formula 619]

[ chemical formula 620]

[ chemical formula 621]

[ chemical formula 622]

[ chemical formula 623]

[ chemical formula 624]

[ chemical formula 625]

[ chemical formula 626]

[ chemical formula 627]

[ chemical formula 628]

[ chemical formula 629]

[ chemical formula 630]

[ chemical formula 631]

[ chemical formula 632]

[ chemical formula 633]

[ chemical formula 634]

[ chemical formula 635]

[ chemical formula 636]

[ chemical formula 637]

[ chemical formula 638]

[ chemical formula 639]

[ chemical formula 640]

[ chemical formula 641]

[ chemical formula 642]

[ chemical formula 643]

[ chemical formula 644]

[ chemical formula 645]

[ chemical formula 646]

[ chemical formula 647]

[ chemical formula 648]

[ chemical formula 649]

[ chemical formula 650]

[ chemical formula 651]

[ chemical formula 652]

[ chemistry 653]

[ chemistry 654]

[ chemical formula 655]

[ chemical 656]

[ chemical formula 657]

[ chemical formula 658]

[ chemical formula 659]

[ chemical formula 660]

[ chemical formula 661]

[ chemical formula 662]

[ chemical formula 663]

[ chemical formula 664]

[ chemical formula 665]

[ chemical formula 666]

[ chemical formula 667]

[ chemical formula 668]

[ chemical formula 669]

[ chemical formula 670]

[ chemical formula 671]

[ chemical formula 672]

[ chemical formula 673]

[ chemical formula 674]

[ chemical formula 675]

[ chemical formula 676]

[ chemical formula 677]

[ chemical formula 678]

[ chemical formula 679]

[ chemistry 680]

[ chemical formula 681]

[ chemical formula 682]

[ chemical formula 683]

[ chemical formula 684]

[ chemical formula 685]

[ chemical formula 686]

[ chemical formula 687]

[ chemical formula 688]

[ chemical formula 689]

[ chemistry 690]

[ chemical formula 691]

[ chemical formula 692]

[ chemical formula 693]

[ chemical formula 694]

[ chemical formula 695]

[ chemical formula 696]

[ chemical formula 697]

[ chemical formula 698]

[ chemical formula 699]

[ chemical formula 700]

[ chemical formula 701]

[ chemical formula 702]

[ chemical formula 703]

[ chemical formula 704]

[ chemical formula 705]

[ chemical formula 706]

[ chemical formula 707]

[ chemical formula 708]

[ chemical formula 709]

[ chemical formula 710]

[ chemical formula 711]

[ chemical formula 712]

[ chemical formula 713]

[ chemical formula 714]

[ chemical formula 715]

[ chemical formula 716]

[ chemical formula 717]

[ chemical formula 718]

[ chemical formula 719]

[ chemical formula 720]

[ chemical formula 721]

[ chemical formula 722]

[ chemical formula 723]

[ chemical formula 724]

[ chemical formula 725]

[ chemical formula 726]

[ chemical formula 727]

[ chemical formula 728]

[ chemical formula 729]

[ chemical formula 730]

[ chemical formula 731]

/>

[ chemical formula 732]

[ chemical formula 733]

[ chemical formula 734]

[ chemical formula 735]

[ chemical formula 736]

/>

[ chemical formula 737]

[ chemical formula 738]

[ chemical formula 739]

[ chemical formula 740]

[ chemical formula 741]

[ chemical formula 742]

[ chemical formula 743]

[ chemical formula 744]

[ chemical formula 745]

[ chemical formula 746]

[ chemical formula 747]

[ chemical formula 748]

[ chemical formula 749]

[ chemical formula 750]

[ chemical formula 751]

[ chemical formula 752]

[ chemical formula 753]

/>

< Compound (2) >)

The compound (2) is a compound represented by the following formula (2).

The compound (2) is contained in the organic layer of the organic EL element of the present invention.

In addition, the compound (2) is contained in the composition of the present invention.

[ chemical formula 754]

In the formula (2), the amino acid sequence of the compound,

L ¹¹ And L ¹² Each independently is preferably a single bond, Or a substituted or unsubstituted arylene group having 6 to 14 ring members. Preferably L ¹¹ And L ¹² At least 1 of which is a single bond.

Ar ¹¹ Preferably a substituted or unsubstituted aryl group having 6 to 30 ring members.

Ar ¹¹ More preferably, the group represented by the following formulas (a 1) to (a 4) is selected.

[ chemical formula 755]

In the formulae (a 1) to (a 4), the formula (A) represents a group represented by formula (A) and (B) ¹¹ Is used for the bonding position of the substrate.

R ¹⁴⁰ Is that

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

Substituted or unsubstituted cycloalkyl having 3 to 50 ring members,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ )、

-O-(R ₉₀₄ )、

-S-(R ₉₀₅ )、

-N(R ₉₀₆ )(R ₉₀₇ )、

Halogen atom, cyano group, nitro group,

Substituted or unsubstituted aryl groups having 6 to 50 ring members, or

A monovalent heterocyclic group having 5 to 50 ring members which may be substituted or unsubstituted.

R ₉₀₁ ～R ₉₀₇ The definition of the "substituent described in the present specification" is the same as that of the "substituent described in the present specification".

p1 is an integer of 0 to 4.

p2 is an integer of 0 to 5.

p3 is an integer of 0 to 7.

When p1 to p3 are each 2 or more, a plurality of R ¹⁴⁰ May be the same or different from each other.

When p1 to p3 are 2 or more, a plurality of R's are adjacent ¹⁴⁰ Are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or are not bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring.

R ²¹ ～R ²⁸ And R is ³¹ ～R ³⁸ Each independently is preferably a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, more preferably a hydrogen atom.

R ²¹ ～R ²⁸ And R is ³¹ ～R ³⁸ Details and preferred examples of the unsubstituted, cyclic C1-50 alkyl group shown above are as described above for R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ The same applies to the description of (2).

R ²¹ ～R ²⁸ And R is ³¹ ～R ³⁸ Details and preferred examples of the unsubstituted aryl group having 6 to 50 ring-forming carbon atoms shown above are as described above for R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ The same applies to the description of (2).

R ²¹ ～R ²⁸ R being a hydrogen atom, other than a single bond to the onium f ³¹ ～R ³⁸ May be a hydrogen atom.

X ² Is an oxygen atom, a sulfur atom, or CR ^a R ^b ，

Wherein,,

selected from R other than the single bonds mentioned ³¹ ～R ³⁸ The adjacent 2 of the two may be bonded to each other to form a ring, or may not form a ring.

X ² Preferably an oxygen atom or a sulfur atom, more preferably an oxygen atom.

R ^a And R is ^b Details and preferred examples of the unsubstituted, cyclic C1-50 alkyl group shown above are as described above for R ^d And R is ^e The same applies to the description of (2).

R ^a And R is ^b Details and preferred examples of the unsubstituted aryl group having 6 to 50 ring-forming carbon atoms shown above are as described above for R ^d And R is ^e The same applies to the description of (2).

From R ^a And R is R ^b Details of the unsubstituted ring formed and those described above for R ^d And R is ^e The same applies to the description of (2).

In one embodiment of the present invention, the compound (2) is preferably a compound represented by the following formula (2A).

[ chemical formula 756]

In the formula (2A), the amino acid sequence of the formula (2A),

L ¹¹ 、Ar ¹¹ 、R ²¹ ～R ²⁸ 、R ³¹ ～R ³⁸ 、X ² and f is as defined in formula (2).

In one embodiment of the present invention, the compound (2) is preferably a compound represented by any one of the following formulas (2B) to (2D), and more preferably a compound represented by the following formula (2D).

[ chemical formula 757]

In the formula (2B), the amino acid sequence,

R ^33b ～R ^38b and R is ¹⁴¹ ～R ¹⁴⁴ Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

L ¹¹ 、L ¹² 、Ar ¹¹ 、R ²¹ ～R ²⁸ And X ² The definition is the same as in formula (2).

Wherein,,

selected from R ^33b 、R ^36b ～R ^38b 、R ¹⁴¹ ～R ¹⁴⁴ 、R ^a And R is ^b 1 of them is a single bond to O.

R ^33b ～R ^38b And R is ¹⁴¹ ～R ¹⁴⁴ Details and preferred examples of the unsubstituted, cyclic C1-50 alkyl group shown above are as described above for R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ The same applies to the description of (2).

R ^33b ～R ^38b And R is ¹⁴¹ ～R ¹⁴⁴ Details and preferred examples of the unsubstituted aryl group having 6 to 50 ring-forming carbon atoms shown above are as described above for R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ The same applies to the description of (2).

In one embodiment of the invention, R is preferably ^38b Is a single bond to o.

R is not a single bond to O ^33b ～R ^38b And R is ¹⁴¹ ～R ¹⁴⁴ May be a hydrogen atom.

[ chemical formula 758]

In the formula (2C), the amino acid sequence,

R ^31c 、R ^36c ～R ^38c and R is ¹⁵¹ ～R ¹⁵⁴ Each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted alkyl groupAryl with ring carbon number of 6-50.

Wherein,,

selected from R ^31c 、R ^36c ～R ^38c 、R ¹⁵¹ ～R ¹⁵⁴ 、R ^a And R is ⁶ 1 of them is a single bond to p.

R ^31c 、R ^36c ～R ^38c And R is ¹⁵¹ ～R ¹⁵⁴ Details and preferred examples of the unsubstituted, cyclic C1-50 alkyl group shown above are as described above for R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ The same applies to the description of (2).

R ^31c 、R ^36c ～R ^38c And R is ¹⁵¹ ～R ¹⁵⁴ Details and preferred examples of the unsubstituted aryl group having 6 to 50 ring-forming carbon atoms shown above are as described above for R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ The same applies to the description of (2).

In one embodiment of the invention, R is preferably ^38c Is a single bond to p.

R is not a single bond to p ^31c 、R ^36c ～R ^38c And R is ¹⁵¹ ～R ¹⁵⁴ May be a hydrogen atom.

[ chemical formula 759]

In the formula (2D), the amino acid sequence,

R ^31d 、R ^32d 、R ^36d ～R ^38d and R is ¹⁶¹ ～R ¹⁶⁴ Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

Wherein,,

selected from R ^31d 、R ^32d 、R ^36d ～R ^38d 、R ¹⁶¹ ～R ¹⁶⁴ 、R ^a And R is ^b 1 of them is a single bond to an n.

R ^31d 、R ^32d 、R ^36d ～R ^38d And R is ¹⁶¹ ～R ¹⁶⁴ Details and preferred examples of the unsubstituted, cyclic C1-50 alkyl group shown above are as described above for R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ The same applies to the description of (2).

R ^31d 、R ^32d 、R ^36d ～R ^38d And R is ¹⁶¹ ～R ¹⁶⁴ Details and preferred examples of the unsubstituted aryl group having 6 to 50 ring-forming carbon atoms shown above are as described above for R ¹ ～R ⁸ And R is ¹¹ ～R ¹⁸ The same applies to the description of (2).

In one embodiment of the invention, R is preferably ^38d Is a single bond to q.

R is not a single bond to q ^31d 、R ^32d 、R ^36d ～R ^38d And R is ¹⁶¹ ～R ¹⁶⁴ May be a hydrogen atom.

In one embodiment of the present invention, the compound (2) is preferably a compound represented by the following formula (2 d).

[ chemical formula 760]

In the formula (2 d), the amino acid sequence of the compound,

L ¹¹ 、Ar ¹¹ 、R ²¹ ～R ²⁸ and X ² As defined in the formula (2),

R ^31d 、R ^32d 、R ^35d ～R ^37d and R is ¹⁶¹ ～R ¹⁶⁴ As defined in formula (2D).

In one embodiment of the present invention, the organic EL element of the present invention comprises the compound represented by the above formula (1) in the formula (1),

n is 0, and the number of the n is 0,

r is selected from single bonds other than those bound to a and b ² ～R ⁴ And R is ⁵ ～R ⁷ 1 of them is a single bond to the ene bond,

L ¹ is a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming carbon atoms,

N ^＊、R ¹ ～R ⁸ 、R ¹¹ ～R ¹⁴ 、X ¹ 、Ar ¹ 、Ar ² 、L ² and L ³ In the case where the definition is the same as in formula (1),

the compound represented by the above formula (2) is preferably a compound represented by the above formula (2A).

In another embodiment of the present invention, the organic EL element of the present invention comprises the compound represented by the above formula (1) in the formula (1),

n is 0, and the number of the n is 0,

N ^＊、R ¹ ～R ⁸ 、R ¹¹ ～R ¹⁴ 、＊e、X ¹ 、Ar ¹ 、Ar ² 、L ² and L ³ In the case where the definition is the same as in formula (1),

the compound represented by the formula (2) is preferably a compound represented by any one of the formulas (2B) to (2D).

In still another embodiment of the present invention, the organic EL element of the present invention comprises the compound represented by the above formula (1) in formula (1),

L ¹ is a single bond,

the compound represented by the formula (2) is preferably a compound represented by any one of the formulas (2A) to (2D).

As described above, the term "hydrogen atom" used in the present specification includes protium atom, deuterium atom, and tritium atom. Thus, compound (2) may also contain deuterium atoms of natural origin.

In addition, deuterium atoms can be intentionally introduced into the compound (2) by using a deuterated compound as part or all of the starting compound. Thus, in one embodiment of the invention, compound (2) comprises at least 1 deuterium atom. That is, the compound (2) may be a compound represented by the formula (2), and at least one of hydrogen atoms contained in the compound is a deuterium atom.

L in formula (2) ¹¹ And L ¹² In the case of an arylene group or a divalent heterocyclic group, the arylene group or the divalent heterocyclic group has a hydrogen atom;

ar of formula (2) ¹¹ In the case of an aryl group or a heterocyclic group, the aryl group or the heterocyclic group has a hydrogen atom;

r of formula (2) ²¹ ～R ²⁸ And R is not a single bond to the onium f ³¹ ～R ³⁸ A hydrogen atom represented by any one of the above;

r in formula (2) ²¹ ～R ²⁸ And R is not a single bond to the onium f ³¹ ～R ³⁸ Any one of the above is an alkyl group or an aryl group, and the alkyl group or the aryl group has a hydrogen atom;

r of formula (2) ^a And R is ^b A hydrogen atom represented by any one of the above;

r in formula (2) ^a And R is ^b In the case of an alkyl group or an aryl group, the alkyl group or the aryl group has a hydrogen atom;

R of formula (2B) is not a single bond to O ^33b 、R ^36b ～R ^38b And R is ¹⁴¹ ～R ¹⁴⁴ And R is ^34b And R is ^35b A hydrogen atom represented by any one of the above;

r of formula (2C) is not a single bond to p ^31c 、R ^36c ～R ^38c And R is ¹⁵¹ ～R ¹⁵⁴ And R is ^34c And R is ^35c A hydrogen atom represented by any one of the above;

r of formula (2D) is not a single bond to q ^31d 、R ^32d 、R ^36d ～R ^38d And R is ¹⁶¹ ～R ¹⁶⁴ And R is ^35d Any one of the hydrogen atoms represented by the formula (I).

The deuteration rate of the compound (2) depends on the deuteration rate of the raw material compound used. Even if a raw material having a predetermined deuteration rate is used, the protium isotope may be contained in a constant ratio from a natural source. Accordingly, the following schemes of deuteration rates of the inventive compounds include ratios in which the natural-derived trace isotopes are considered, relative to ratios obtained by counting only the number of deuterium atoms represented by the chemical formula.

The deuteration rate of the compound (2) is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, still more preferably 10% or more, and still more preferably 50% or more.

The compound (2) may be a mixture containing a deuterated compound and a non-deuterated compound, a mixture of 2 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, still more preferably 10% or more, still more preferably 50% or more, and less than 100%.

The ratio of the number of deuterium atoms in the compound (2) to the total number of hydrogen atoms is preferably 1% or more, more preferably 3% or more, still more preferably 5% or more, still more preferably 10% or more and 100% or less.

The compound (2) can be easily produced by those skilled in the art with reference to the following synthesis examples and known synthesis methods.

Specific examples of the compound (2) are shown below, but are not limited to the following exemplified compounds.

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

[ chemical formula 761]

[ chemical formula 762]

[ chemical formula 763]

[ chemical formula 764]

[ chemical formula 765]

[ chemical formula 766]

[ chemical formula 767]

[ chemical formula 768]

[ chemical formula 769]

[ chemical formula 770]

[ chemical formula 771]

[ chemical 772]

[ chemical formula 773]

[ chemical formula 774]

[ chemical formula 775]

[ chemical formula 776]

[ chemical formula 777]

[ chemical formula 778]

[ chemical formula 779]

[ chemical formula 780]

[ chemical formula 781]

[ chemical formula 782]

[ chemical formula 783]

[ chemical formula 784]

[ chemical formula 785]

[ chemical formula 786]

[ chemical formula 787]

[ chemical formula 788]

[ chemical formula 789]

[ chemical formula 790]

[ chemical formula 791]

[ chemical formula 792]

[ chemical formula 793]

[ chemical formula 794]

[ chemical formula 795]

[ chemical formula 796]

[ chemical formula 797]

[ chemical formula 798]

[ chemical formula 799]

[ chemical formula 800]

[ chemical formula 801]

[ chemical formula 802]

[ chemical formula 803]

[ chemical formula 804]

[ chemical formula 805]

[ chemical formula 806]

[ chemical formula 807]

[ chemical formula 808]

[ chemical formula 809]

[ chemical formula 810]

[ chemical formula 811]

[ chemical formula 812]

[ chemical formula 813]

[ chemical formula 814]

[ chemical formula 815]

[ chemical formula 816]

[ chemical formula 817]

[ chemical formula 818]

[ chemical formula 819]

[ chemical formula 820]

[ chemical formula 821]

[ chemical formula 822]

[ chemical formula 823]

[ chemical formula 824]

[ chemical formula 825]

[ chemical formula 826]

[ chemical formula 827]

[ chemical formula 828]

[ chemical formula 829]

[ chemical formula 830]

[ chemical formula 831]

[ chemical formula 832]

[ chemical formula 833]

[ chemical formula 834]

[ chemical formula 835]

[ chemical formula 836]

[ chemical formula 837]

[ chemical formula 838]

[ chemical formula 839]

[ chemical formula 840]

[ chemical formula 841]

[ chemical formula 842]

[ chemical formula 843]

[ chemical formula 844]

[ chemical formula 845]

[ chemical formula 846]

[ chemical formula 847]

[ chemical formula 848]

[ chemical formula 849]

[ chemical formula 850]

[ chemical formula 851]

[ chemical formula 852]

[ chemical formula 853]

[ chemical formula 854]

[ chemical formula 855]

[ chemical formula 856]

[ chemical formula 857]

[ chemical formula 858]

[ chemical formula 859]

[ chemical formula 860]

[ chemical formula 861]

[ chemical formula 862]

[ chemical formula 863]

[ chemical formula 864]

[ chemical formula 865]

[ chemical formula 866]

[ chemical formula 867]

[ chemical formula 868]

[ chemical formula 869]

[ chemical formula 870]

[ chemical formula 871]

[ chemical formula 872]

[ chemical formula 873]

[ chemical formula 874]

[ chemical formula 875]

[ chemical formula 876]

[ chemical formula 877]

[ chemical formula 878]

[ chemical formula 879]

[ chemical formula 880]

[ chemical formula 881]

[ chemical formula 882]

[ chemical formula 883]

[ chemical formula 884]

[ chemical formula 885]

[ chemical formula 886]

[ chemical formula 887]

[ chemical formula 888]

[ chemical formula 889]

[ chemical formula 890]

[ chemical formula 891]

[ chemical formula 892]

[ chemical formula 893]

[ chemical formula 894]

[ chemical formula 895]

[ chemical formula 896]

[ chemical formula 897]

[ chemical formula 898]

[ chemical formula 899]

[ chemical formula 900]

[ chemical formula 901]

[ chemical formula 902]

< organic EL element >)

An organic EL element of the present invention has a cathode, an anode, and an organic layer located between the cathode and the anode, wherein the organic layer contains a light-emitting layer, and the organic layer contains a compound represented by formula (1) and a compound represented by formula (2).

Examples of the organic layer included in the organic EL element include, but are not limited to, a hole transport region (a hole injection layer, a hole transport layer, an electron blocking layer, an exciton blocking layer, and the like) provided between the anode and the light emitting layer, a spacer layer, an electron transport region (an electron injection layer, an electron transport layer, a hole blocking layer, and the like) provided between the cathode and the light emitting layer, and the like.

In one embodiment of the present invention, the organic layer includes a hole transport region located between the anode and the light-emitting layer, and the hole transport region includes a compound (1)) represented by the formula (1).

In addition, in one embodiment of the present invention, the light-emitting layer contains a compound represented by the above formula (2).

The organic EL element of the present invention may be a fluorescent or phosphorescent single-color light-emitting element, a fluorescent/phosphorescent hybrid white light-emitting element, a simple type having a single light-emitting unit, or a tandem type having a plurality of light-emitting units, and among these, a fluorescent light-emitting element is preferable. Here, the "light emitting unit" means: comprises an organic layer, wherein at least one layer is a light-emitting layer and the injected holes and electrons are recombined to emit light by the least unit.

For example, the following element configuration is typical of a simple organic EL element.

(1) Anode/light emitting unit/cathode

In addition, the light-emitting unit may be a multilayer structure having a plurality of phosphorescent light-emitting layers and fluorescent light-emitting layers, and in this case, a spacer layer may be provided between the light-emitting layers for the purpose of preventing excitons generated in the phosphorescent light-emitting layers from diffusing into the fluorescent light-emitting layers. A typical layer configuration of the simple light emitting unit is shown below. The layers in brackets are optional.

(a) (hole injection layer /) hole transport layer/fluorescent light emitting layer/electron transport layer (/ electron injection layer)

(b) (hole injection layer /) hole transport layer/1 st fluorescent light-emitting layer/2 nd fluorescent light-emitting layer/electron transport layer (/ electron injection layer)

(c) (hole injection layer /) hole transport layer/phosphorescent light emitting layer/spacer layer/fluorescent light emitting layer/electron transport layer (/ electron injection layer)

(d) (hole injection layer /) hole transport layer/1 st phosphorescent light emitting layer/2 nd phosphorescent light emitting layer/spacer layer/fluorescent light emitting layer/electron transport layer (/ electron injection layer)

(e) (hole injection layer /) hole transport layer/phosphorescent light emitting layer/spacer layer/1 st fluorescent light emitting layer/2 nd fluorescent light emitting layer/electron transport layer (/ electron injection layer)

(f) (hole injection layer /) hole transport layer/electron blocking layer/fluorescent light emitting layer/electron transport layer (/ electron injection layer)

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

(h) (hole injection layer /) 1 st hole transport layer/2 nd hole transport layer/fluorescent light-emitting layer/electron transport layer (/ electron injection layer)

(i) (hole injection layer /) 1 st hole transport layer/2 nd hole transport layer/fluorescent light-emitting layer/1 st electron transport layer/2 nd electron transport layer (/ electron injection layer)

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

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

(l) (hole injection layer /) 1 st hole transport layer/2 nd hole transport layer/1 st fluorescent light-emitting layer/2 nd fluorescent light-emitting layer/1 st electron transport layer/2 nd electron transport layer (/ electron injection layer)

(m) (hole injection layer /) 1 st hole transport layer/2 nd hole transport layer/3 rd hole transport layer/1 st fluorescent light-emitting layer/2 nd fluorescent light-emitting layer/1 st electron transport layer/2 nd electron transport layer (/ electron injection layer)

The phosphorescent or fluorescent light-emitting layers may be light-emitting layers each of which exhibits a different light-emitting color. Specifically, the light-emitting unit (f) includes a layer structure such as a hole transport layer (hole injection layer /) a 1 st phosphorescent light-emitting layer (red light emission)/a 2 nd phosphorescent light-emitting layer (green light emission)/a spacer layer/a fluorescent light-emitting layer (blue light emission)/an electron transport layer.

An electron blocking layer may be provided between each light emitting layer and the hole transport layer or the spacer layer as appropriate. In addition, a hole blocking layer may be provided between each light emitting layer and the electron transport layer as appropriate. By providing the electron blocking layer and the hole blocking layer, electrons or holes can be enclosed in the light emitting layer, and the recombination probability of charges in the light emitting layer can be improved, thereby improving the light emitting efficiency.

Typical element configurations of the tandem organic EL element include the following.

(2) Anode/1 st light-emitting unit/intermediate layer/2 nd light-emitting unit/cathode

Here, the 1 st light-emitting unit and the 2 nd light-emitting unit may be, for example, each independently selected from the light-emitting units described above.

The intermediate layer is also generally referred to as an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, or an intermediate insulating layer, and may be formed using a known material that supplies electrons to the 1 st light-emitting cell and holes to the 2 nd light-emitting cell.

Fig. 1 is a schematic diagram showing an example of the structure of an organic EL element of the present invention. The organic EL element 1 includes 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 region 6 (hole injection layer, hole transport layer, etc.) is provided between the light-emitting layer 5 and the anode 3, and an electron transport region 7 (electron injection layer, electron transport layer, etc.) is provided between the light-emitting layer 5 and the cathode 4. 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. This can further improve the efficiency of generating excitons in the light-emitting layer 5 by blocking electrons and holes in the light-emitting layer 5.

Fig. 2 is a schematic diagram showing another configuration of the organic EL element of the present invention. The organic EL element 11 includes 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 1 st light emitting layer 5a and a 2 nd light emitting layer 5b. The hole transport region disposed between the anode 3 and the 1 st light-emitting layer 5a is formed of a hole injection layer 6a, a 1 st hole transport layer 6b, and a 2 nd hole transport layer 6 c. The electron transport region disposed between the 2 nd light-emitting layer 5b and the cathode 4 is formed by the 1 st electron transport layer 7a and the 2 nd electron transport layer 7 b.

Fig. 3 is a schematic diagram showing another configuration of the organic EL element of the present invention. The organic EL element 12 includes a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 30 disposed between the anode 3 and the cathode 4. The light emitting unit 30 has a 1 st light emitting layer 5a and a 2 nd light emitting layer 5b. The hole transport region disposed between the anode 3 and the 1 st light-emitting layer 5a is formed of a hole injection layer 6a, a 1 st hole transport layer 6b, a 2 nd hole transport layer 6c, and a 3 rd hole transport layer 6 d. The electron transport region disposed between the 2 nd light-emitting layer 5b and the cathode 4 is formed by the 1 st electron transport layer 7a and the 2 nd electron transport layer 7 b.

In the present invention, a host combined with a fluorescent dopant material (fluorescent light-emitting material) is referred to as a fluorescent host, and a host combined with a phosphorescent dopant material is referred to as a phosphorescent host. Fluorescent and phosphorescent hosts are not distinguished solely by molecular structure. That is, the phosphorescent host means a material forming a phosphorescent light emitting layer containing a phosphorescent dopant, and does not mean that the material cannot be used as a material forming a fluorescent light emitting layer. The same applies to the fluorescent body.

(substrate)

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

(anode)

The anode formed on the substrate is preferably made of a metal, an alloy, a conductive compound, or a mixture thereof having a large work function (specifically, 4.0eV or more). Specifically, examples thereof include: indium Tin Oxide (ITO), indium Tin Oxide containing silicon or silicon Oxide, indium zinc Oxide, indium Oxide containing tungsten Oxide and zinc Oxide, graphene, and the like. Examples of the metal include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), and nitrides thereof (for example, titanium nitride). And (5) outputting.

These materials are typically formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target in which zinc oxide is added in an amount of 1 to 10wt% relative to indium oxide, and indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target in which tungsten oxide is added in an amount of 0.5 to 5wt% and zinc oxide is added in an amount of 0.1 to 1wt% relative to indium oxide. The composition may be produced by vacuum vapor deposition, coating, ink jet, spin coating, or the like.

(hole transporting region)

As described above, the organic layer may include a hole transport region between the anode and the light emitting layer. The hole transport region is composed of a hole injection layer, a hole transport layer, an electron blocking layer, and the like. The hole transport region preferably contains the compound (1). Preferably, at least one of the layers constituting the hole transport region contains the compound (1), and even more preferably, the hole transport layer contains the compound (1).

The hole injection layer formed adjacent to the anode is formed using a material that is easily subjected to hole injection regardless of the work function of the anode, and therefore, a material that is generally used as an electrode material (for example, a metal, an alloy, a conductive compound, and a mixture thereof, an element belonging to the first group or the second group of the periodic table) can be used.

An alkali metal such as lithium (Li) and cesium (Cs), an alkaline earth metal such as magnesium (Mg), calcium (Ca) and strontium (Sr), an alloy containing the same (for example, mgAg, alLi), a rare earth metal such as europium (Eu) and ytterbium (Yb), an alloy containing the same, and the like can be used as the material having a small work function. In the case of forming the anode using an alkali metal, an alkaline earth metal, or an alloy containing them, a vacuum vapor deposition method or a sputtering method may be used. In addition, when silver paste or the like is used, a coating method, an inkjet method, or the like may be used.

(hole injection layer)

The hole injection layer is a layer containing a material having high hole injection property (hole injection material), and is formed between the anode and the light-emitting layer, or between the hole transport layer and the anode in the presence of the hole transport layer.

As the hole injecting material, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, or the like can be used.

Examples of the hole injection layer material include 4,4',4 "-tris (N, N-diphenylamino) triphenylamine (abbreviated as TDATA), 4',4" -tris [ N- (3-methylphenyl) -N-phenylamino ] triphenylamine (abbreviated as MTDATA), 4 '-bis [ N- (4-diphenylaminophenyl) -N-phenylamino ] biphenyl (abbreviated as DPAB), 4' -bis (N- {4- [ N '- (3-methylphenyl) -N' -phenylamino ] phenyl } -N-phenylamino) biphenyl (abbreviated as DNTPD), 1,3, 5-tris [ N- (4-diphenylaminophenyl) -N-phenylamino ] benzene (abbreviated as DPA 3B), 3- [ N- (9-phenylcarbazole-3-yl) -N-phenylamino ] -9-phenylcarbazole (abbreviated as PCzPCA 1), 3, 6-bis [ N- (9-phenylcarbazole-3-yl) -N-phenylamino ] -9-phenylcarbazole (abbreviated as PCA (abbreviated as PCzPCC 2), aromatic amine compounds such as 3- [ N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) amino ] -9-phenylcarbazole (abbreviated as PCzPCN 1).

Polymer compounds (oligomers, dendrimers, polymers, etc.) may also be used. Examples thereof include: and polymer compounds such as Poly (N-vinylcarbazole) (PVK), poly (4-vinyltriphenylamine) (PVTPA), poly [ N- (4- { N '- [4- (4-diphenylamino) phenyl ] phenyl-N' -phenylamino } phenyl) methacrylamide ] (PTPDMA), and Poly [ N, N '-bis (4-butylphenyl) -N, N' -bis (phenyl) benzidine ] (Poly-TPD). In addition, acid-added polymer compounds such as poly (3, 4-ethylenedioxythiophene)/poly (styrenesulfonic acid) (PEDOT/PSS) and polyaniline/poly (styrenesulfonic acid) (PAni/PSS) may be used.

In addition, an acceptor material such as a Hexaazatriphenylene (HAT) compound represented by the following formula (K) is also preferably used.

[ chemical formula 903]

(in the above formula, R ²²¹ ～R ²²⁶ Each independently represents cyano, -CONH ₂ Carboxyl, or-COOR ²²⁷ (R ²²⁷ Represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms). In addition, is selected from R ²²¹ And R is R ²²² 、R ²²³ And R is R ²²⁴ R is as follows ²²⁵ And R is R ²²⁶ Adjacent ones of the two groups may be bonded to each other to form a group represented by-CO-O-CO-. )

As R ²²⁷ Examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl and the like.

(hole transporting layer)

The hole-transporting layer is a layer containing a material having high hole-transporting property (hole-transporting material), and is formed between the anode and the light-emitting layer, or between the hole-injecting layer and the light-emitting layer in the presence of the hole-injecting layer. The compound (1) may be used alone or in combination with the following compound for the hole transport layer, the compound (2) may be used alone or in combination with the following compound for the hole transport layer, and the compound (1) alone or in combination with the following compound for the hole transport layer is preferable.

The hole transport layer may have a single-layer structure or a multilayer structure including 2 or more layers. For example, the hole transport layer may be a 2-layer structure including a 1 st hole transport layer (anode side) and a 2 nd hole transport layer (cathode side). That is, the hole transport region may include a 1 st hole transport layer on the anode side and a 2 nd hole transport layer on the cathode side. In addition, the hole transport layer may have a 3-layer structure including a 1 st hole transport layer, a 2 nd hole transport layer, and a 3 rd hole transport layer in this order from the anode side. That is, a 3 rd hole transport layer may be disposed between the 2 nd hole transport layer and the light-emitting layer.

In one embodiment of the present invention, the hole transport layer of the single layer structure is preferably adjacent to the light emitting layer, or a hole transport layer closest to the cathode, for example, a 2 nd hole transport layer of the 2-layer structure and a 3 rd hole transport layer of the 3-layer structure, among the hole transport layers of the multilayer structure are preferably adjacent to the light emitting layer. In another embodiment of the present invention, an electron blocking layer or the like described below is interposed between the hole transporting layer and the light emitting layer having the single-layer structure or between the hole transporting layer and the light emitting layer closest to the light emitting layer in the multilayer structure.

In one embodiment of the present invention, the hole transport region preferably includes 2 or more hole transport layers, and at least 1 layer of the hole transport layers includes the compound (1). That is, in the case where the hole transport layer has a 2-layer structure, at least one of the 1 st hole transport layer and the 2 nd hole transport layer contains the compound (1). The compound (1) may be contained in one or both of the 1 st hole transport layer and the 2 nd hole transport layer. In one embodiment of the present invention, it is preferable that the hole transport region includes a 1 st hole transport layer on the anode side and a 2 nd hole transport layer on the cathode side, and the compound (1) is included in the 2 nd hole transport layer. That is, it is preferable that the compound (1) is contained only in the 2 nd hole transport layer, or that the compound (1) is contained in both of the 1 st hole transport layer and the 2 nd hole transport layer.

In another embodiment of the present invention, it is preferable that the hole transport region contains 3 or more hole transport layers, and at least 1 layer of the hole transport layers contains the compound (1). That is, in the case where the hole transport layer has a 3-layer structure, at least one of the 1 st to 3 rd hole transport layers contains the compound (1). The compound (1) may be contained in only one of the 1 st to 3 rd hole transport layers, may be contained in only any 2 layers, or may be contained in all layers. In one embodiment of the present invention, it is preferable that the compound (1) is contained in the 3 rd hole transport layer. That is, it is preferable that the compound (1) is contained only in the 3 rd hole transport layer, or that the compound (1) is contained in one or both of the 3 rd hole transport layer, the 1 st hole transport layer, and the 2 nd hole transport layer.

In one embodiment of the present invention, it is preferable that the hole transport layer closest to the cathode side among the hole transport layers contains the compound (1).

In one embodiment of the present invention, the compound (1) contained in each of the transport layers is preferably a protium body from the viewpoint of manufacturing cost. The protium is the compound (1) in which all hydrogen atoms in the compound of the present invention are protium atoms.

Accordingly, the present invention includes an organic EL element in which at least one of the 1 st hole transport layer and the 2 nd hole transport layer (in the case of a 2-layer structure) and at least one of the 1 st to 3 rd hole transport layers contains compound (1) substantially containing only a protium. The expression "compound (1) substantially containing only protium" means that the protium content is 90 mol% or more, preferably 95 mol% or more, more preferably 99 mol% or more (each including 100%) based on the total amount of compound (1).

Examples of the hole transport layer material other than the compound (1) include an aromatic amine compound, a carbazole derivative, and an anthracene derivative.

Examples of the aromatic amine compound include: 4,4' -bis [ N- (1-naphthyl) -N-phenylamino ]]Biphenyl (NPB), N ' -bis (3-methylphenyl) -N, N ' -diphenyl- [1,1' -biphenyl ]-4,4' -diamine (abbreviated as TPD), 4-phenyl-4 ' - (9-phenylfluoren-9-yl) triphenylamine (abbreviated as BAFLP), 4' -bis [ N- (9, 9-dimethylfluoren-2-yl) -N-phenylamino]Biphenyl (abbreviation: DFLDPBi), 4',4″ -tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4',4 "-tris [ N- (3-methylphenyl) -N-phenylamino]Triphenylamine (MTDATA for short), 4 '-bis [ N- (spiro-9, 9' -bifluorene-2-yl) -N-phenylamino ]]Biphenyl (for short: BSPB). The above compound has 10 ^-6 cm ² Hole mobility above/Vs.

Examples of carbazole derivatives include 4,4' -bis (9-carbazolyl) biphenyl (abbreviated as CBP), 9- [4- (9-carbazolyl) phenyl ] -10-phenylanthracene (abbreviated as CzPA), and 9-phenyl-3- [4- (10-phenyl-9-anthryl) phenyl ] -9H-carbazole (abbreviated as PCzPA).

Examples of the anthracene derivative include 2-t-butyl-9, 10-bis (2-naphthyl) anthracene (abbreviated as t-BuDNA), 9, 10-bis (2-naphthyl) anthracene (abbreviated as DNA), and 9, 10-diphenylanthracene (abbreviated as DPAnth).

Polymer compounds such as poly (N-vinylcarbazole) (PVK) and poly (4-vinyltriphenylamine) (PVTPA) may also be used.

Among them, compounds other than the above compounds may be used as long as they have a higher hole-transporting property than electron-transporting property.

In one embodiment of the organic EL element having a 2-layer structure or a hole transport layer of 2 or more layers according to the present invention, the 1 st hole transport layer preferably contains a compound represented by the following formula (11) or (12).

In the organic EL element having the hole transport layer of the 3-layer structure of the present invention, it is preferable that one or both of the 1 st hole transport layer and the 2 nd hole transport layer contain 1 or two or more compounds represented by the following formula (11) or (12).

In the organic EL element having the hole transport layer of the n-layer structure (n is an integer of 4 or more) of the present invention, it is preferable that at least 1 layer of the 1 st hole transport layer to the (n-1) th hole transport layer contains 1 or two or more compounds represented by the following formula (11) or formula (12).

[ chemical formula 904]

[ in the above-mentioned formula (11) and formula (12),

L ^A1 、L ^B1 、L ^C1 、L ^A2 、L ^B2 、L ^C2 and L ^D2 Each independently is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming carbon atoms,

k is 1, 2, 3 or 4,

in the case where k is 1, L ^E2 Is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming carbon atoms,

In the case where k is 2, 3 or 4, 2, 3 or 4L ^E2 Are the same as or different from each other,

in the case where k is 2, 3 or 4, a plurality of L ^E2 Are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other,

l not forming the single ring and not forming the condensed ring ^E2 Is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming carbon atoms,

A ¹ 、B ¹ 、C ¹ 、A ² 、B ² 、C ² and D ² Each independently is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming carbon atoms, or-Si (R '' ₉₀₁ )(R’ ₉₀₂ )(R’ ₉₀₃ )，

R’ ₉₀₁ 、R’ ₉₀₂ And R'. ₉₀₃ Each independently is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms,

at R' ₉₀₁ Where there are plural, plural R's' ₉₀₁ Are the same as or different from each other,

at R' ₉₀₂ Where there are plural, plural R's' ₉₀₂ Are the same as or different from each other,

at R' ₉₀₃ Where there are plural, plural R's' ₉₀₃ The same or different from each other.

R ₉₀₁ ～R ₉₀₇ Each independently is a hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted cycloalkyl having 3 to 50 ring members,

Substituted or unsubstituted aryl groups having 6 to 50 ring members, or

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

at R ₉₀₁ Where there are plural, plural R' s ₉₀₁ Are the same as or different from each other,

at R ₉₀₂ Where there are plural, plural R' s ₉₀₂ Are the same as or different from each other,

at R ₉₀₃ Where there are plural, plural R' s ₉₀₃ Are the same as or different from each other,

at R ₉₀₄ Where there are plural, plural R' s ₉₀₄ Are the same as or different from each other,

at R ₉₀₅ Where there are plural, plural R' s ₉₀₅ Are the same as or different from each other,

at R ₉₀₆ Where there are plural, plural R' s ₉₀₆ Are the same as or different from each other,

at R ₉₀₇ Where there are plural, plural R' s ₉₀₇ The same or different from each other.]

In the formula (11) and the formula (12), A1, B1, C1, A2, B2, C2, and D2 are preferably each independently selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, and a substituted or unsubstituted carbazolyl group.

In addition, more preferably, in the formula (11), at least one of A1, B1 and C1, and in the formula (12), at least one of A2, B2, C2 and D2 is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

The fluorenyl group preferable for A1, B1, C1, A2, B2, C2, and D2 may have a substituent at the 9-position, and may be, for example, 9-dimethylfluorenyl group, 9-diphenylfluorenyl group. In addition, a ring may be formed by substituents at the 9-position, and for example, a fluorene skeleton or a xanthene skeleton may be formed by substituents at the 9-position.

L ^A1 、L ^B1 、L ^C1 、L ^A2 、L ^B2 、L ^C2 And L ^D2 Preferably each independently is a single bond, a substituted or unsubstituted arylene group having 6 to 12 ring-forming carbon atoms.

Specific examples of the compounds represented by the formulas (11) and (12) include the following compounds.

[ chemical formula 905]

(light-emitting region)

The light-emitting region is composed of a single light-emitting layer, a plurality of light-emitting layers, a spacer layer between the plurality of light-emitting layers and each light-emitting layer, and the like. In one embodiment of the present invention, the light-emitting layer preferably contains 2 or more layers. Preferably, any one of these layers contains the compound (2), and even more preferably, the light-emitting layer contains the above-mentioned compound 2.

(dopant material of light-emitting layer)

The light-emitting layer is a layer containing a material having high light-emitting properties (dopant material), and various materials can be used. For example, a fluorescent light-emitting material, a phosphorescent light-emitting material may be used as the dopant material. The fluorescent light-emitting material is a compound that emits light in a singlet excited state, and the phosphorescent light-emitting material is a compound that emits light in a triplet excited state.

As a blue-based fluorescent light-emitting material which can be used for the light-emitting layer, a pyrene derivative, a styrylamine derivative, a,Derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, and the like. Specifically, N' -bis [4- (9H-carbazol-9-yl) phenyl ] can be mentioned]-N, N '-diphenylstilbene-4, 4' -diamine (abbreviated as YGA 2S), 4- (9H-carbazol-9-yl) -4'- (10-phenyl-9-anthryl) triphenylamine (abbreviated as YGAPA), 4- (10-phenyl-9-anthryl) -4' - (9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviated as PCBAPA), and the like.

As a green-based fluorescent light-emitting material that can be used for 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 as: 2 PCAPA), N- [9, 10-bis (1, 1' -biphenyl-2-yl) -2-anthryl ] -N, 9-diphenyl-9H-carbazol-3-amine (abbreviated as: 2 PCABPhA), N- (9, 10-diphenyl-2-anthryl) -N, N ', N ' -triphenyl-1, 4-phenylenediamine (abbreviated as: 2 DPAPA), N- [9, 10-bis (1, 1' -biphenyl-2-yl) -2-anthryl ] -N, N ', N ' -triphenyl-1, 4-phenylenediamine (abbreviated as: 2 DPABPhA), N- [9, 10-bis (1, 1' -biphenyl-2-yl) ] -N- [4- (9H-carbazol-9-yl) phenyl ] -N-phenylanthracene-2-amine (abbreviated as: 2 DPPhA), N, 9-triphenylanthracene-9-amine (abbreviated as: DPPhA) and the like can be mentioned.

As a red-based fluorescent light-emitting material that can be used for the light-emitting layer, a naphthacene derivative, a diamine derivative, or the like can be used. Specifically, N, N, N ', N' -tetrakis (4-methylphenyl) tetracene-5, 11-diamine (abbreviated as p-mPHTD), 7, 14-diphenyl-N, N, N ', N' -tetrakis (4-methylphenyl) acenaphtho [1,2-a ] fluoranthene-3, 10-diamine (abbreviated as p-mPHIFD) and the like are exemplified.

In one embodiment of the invention, the light-emitting layer preferably comprises a fluorescent light-emitting material (fluorescent dopant material).

As a blue-based phosphorescent light-emitting material that can be used for the light-emitting layer, a metal complex such as an iridium complex, an osmium complex, or a platinum complex can be used. Specifically, bis [2- (4 ',6' -difluorophenyl) pyridine-N, C2'] iridium (III) tetrakis (1-pyrazolyl) borate (abbreviated as Fir 6), bis [2- (4', 6 '-difluorophenyl) pyridine-N, C2' ] iridium (III) pyridine formate (abbreviated as FIrpic), bis [2- (3 ',5' -bistrifluoromethylphenyl) pyridine-N, C2'] iridium (III) pyridine formate (abbreviated as Ir (CF 3 ppy) 2 (pic)), bis [2- (4', 6 '-difluorophenyl) pyridine-N, C2' ] iridium (III) acetylacetonate (abbreviated as FIracac) and the like can be cited.

As a green-based phosphorescent light-emitting material that can be used for the light-emitting layer, iridium complex or the like can be used. Examples thereof include tris (2-phenylpyridine-N, C2 ') iridium (III) (abbreviated as Ir (ppy) 3), bis (2-phenylpyridine-N, C2') iridium (III) acetylacetonate (abbreviated as Ir (ppy) 2 (acac)), bis (1, 2-diphenyl-1H-benzimidazole) iridium (III) acetylacetonate (abbreviated as Ir (pbi) 2 (acac)), and bis (benzo [ H ] quinoline) iridium (III) acetylacetonate (abbreviated as Ir (bzq) 2 (acac)).

As a red-based phosphorescent material that can be used for the light-emitting layer, a metal complex such as iridium complex, platinum complex, terbium complex, or europium complex can be used. Specifically, there may be mentioned organometallic complexes such as bis [2- (2 ' -benzo [4,5- α ] thienyl) pyridine-N, C3' ] iridium (III) acetylacetonate (abbreviated as Ir (btp) 2 (acac)), bis (1-phenylisoquinoline-N, C2 ') iridium (III) acetylacetonate (abbreviated as Ir (piq) 2 (acac)), (acetylacetonate) bis [2, 3-bis (4-fluorophenyl) quinoxaline ] iridium (III) (abbreviated as Ir (Fdpq) 2 (acac)), 2,3,7,8, 12, 13, 17, 18-octaethyl-21H, 23H-porphyrin platinum (II) (abbreviated as PtOEP).

In addition, rare earth metal complexes such as tris (acetylacetonate) (Shan Feige in) terbium (III) (abbreviated as Tb (acac) 3 (Phen)), tris (1, 3-diphenyl-1, 3-acetonyl) (Shan Feige in) europium (III) (abbreviated as Eu (DBM) 3 (Phen)), tris [1- (2-thenoyl) -3, 3-trifluoroacetonyl) (Shan Feige in) europium (III) (abbreviated as Eu (TTA) 3 (Phen)) are useful as phosphorescent materials because they emit light from rare earth metal ions (electron transitions between different multiple degrees).

In one aspect of the invention, the light emitting layer preferably comprises a phosphorescent light emitting material (phosphorescent dopant material).

(host material of light-emitting layer)

The light-emitting layer may be formed by dispersing the dopant material in another material (host material). Preferably, a material is used that has a lowest unoccupied orbital level (LUMO level) higher than the dopant material and a highest occupied orbital level (HOMO level) lower than the dopant material.

In one embodiment of the present invention, the compound (2) is used as a host material for a light-emitting layer.

Other host materials may be used in addition to the compound (2). As other host materials, for example, use is made of

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

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

(3) Carbazole derivative, anthracene derivative, phenanthrene derivative, pyrene derivative, orCondensed aromatic compounds such as derivatives,

(4) Aromatic amine compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives.

For example, it is possible to use: metal complexes such as tris (8-hydroxyquinoline) aluminum (III) (abbreviated as Alq), tris (4-methyl-8-hydroxyquinoline) aluminum (III) (abbreviated as Almq 3), bis (10-hydroxybenzo [ h ] quinoline) beryllium (II) (abbreviated as BeBq 2), bis (2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (abbreviated as BAlq), bis (8-hydroxyquinoline) zinc (II) (abbreviated as Znq), bis [2- (2-benzoxazolyl) phenol ] zinc (II) (abbreviated as ZnPBO), and bis [2- (2-benzothiazolyl) phenol ] zinc (II) (abbreviated as ZnBTZ);

Heterocyclic compounds such as 2- (4-biphenyl) -5- (4-tert-butylphenyl) -1,3, 4-oxadiazole (abbreviated as PBD), 1, 3-bis [5- (p-tert-butylphenyl) -1,3, 4-oxadiazol-2-yl ] benzene (abbreviated as OXD-7), 3- (4-biphenyl) -4-phenyl-5- (4-tert-butylphenyl) -1,2, 4-triazole (abbreviated as TAZ), 2' - (1, 3, 5-trimethoyl) tris (1-phenyl-1H-benzimidazole) (abbreviated as TPBI), bathophenanthroline (abbreviated as BPhen), bathocuproine (abbreviated as BCP);

9- [4- (10-phenyl-9-anthracenyl) phenyl group]-9H-carbazole (abbreviated as CzPA), 3, 6-diphenyl-9- [4- (10-phenyl-9-anthryl) phenyl group]-9H-carbazole (abbreviated as DPCzPA), 9, 10-bis (3, 5-diphenylphenyl) anthracene (abbreviated as DPPA), 9, 10-bis (2-naphthyl) anthracene (abbreviated as DNA), 2-tert-butyl-9, 10-bis (2-naphthyl) anthracene (abbreviated as: t-BuDNA), 9' -dianthracene (abbreviation: BANT), 9'- (stilbene-3, 3' -diyl) phenanthrene (abbreviation: DPNS), 9'- (stilbene-4, 4' -diyl) phenanthrene (abbreviation: DPNS 2), 3',3"- (benzene-1, 3, 5-triyl) tripyrene (abbreviation: TPB 3), 9, 10-diphenylanthracene (abbreviation: DPAnth), 6, 12-dimethoxy-5, 11-diphenylAnd the like condensed aromatic compounds; and

n, N-diphenyl-9- [4- (10-phenyl-9-anthryl) phenyl ] -9H-carbazol-3-amine (abbreviated as CzA PA), 4- (10-phenyl-9-anthryl) triphenylamine (abbreviated as DPhPA), N, 9-diphenyl-N- [4- (10-phenyl-9-anthryl) phenyl ] -9H-carbazol-3-amine (abbreviated as PCAPA), N, 9-diphenyl-N- {4- [4- (10-phenyl-9-anthryl) phenyl ] phenyl } -9H-carbazol-3-amine (abbreviated as PCAPBA), N- (9, 10-diphenyl-2-anthryl) -N, 9-diphenyl-9H-carbazol-3-amine (abbreviated as 2 PCAPA), 4' -bis [ N- (1-naphthyl) -N-phenylamino ] biphenyl (abbreviated as NPB or alpha-NPD), N ' -bis (3-methylphenyl) -N, N ' -diphenyl- [1,1' -biphenyl ] -4,4' -diamine (abbreviated as PCAPBA), 4' -bis [4, 4' -dimethyl-4-fluorenyl ] -4 (abbreviated as DFi), aromatic amine compounds such as 4 '-bis [ N- (spiro-9, 9' -bifluorene-2-yl) -N-phenylamino ] biphenyl (abbreviated as BSPB). Two or more kinds of host materials may be used.

In particular, in the case of a blue fluorescent element, the anthracene compound described below is preferably used as a host material.

[ chemical formula 906]

[ chemical formula 907]

[ chemical formula 908]

In one embodiment of the organic EL element according to the present invention, when the light-emitting layer includes the 1 st light-emitting layer and the 2 nd light-emitting layer, at least one of the components constituting the 1 st light-emitting layer is different from the component constituting the 2 nd light-emitting layer. For example, there may be mentioned: the dopant material contained in the 1 st light-emitting layer is different from the dopant material contained in the 2 nd light-emitting layer, and the host material contained in the 1 st light-emitting layer is different from the host material contained in the 2 nd light-emitting layer.

The film thickness of the light-emitting region in the organic EL element is preferably 5nm to 50nm, more preferably 7nm to 50nm, and even more preferably 10nm to 50 nm. If the film thickness of the light-emitting region is 5nm or more, the light-emitting region is easily formed, and chromaticity is easily adjusted. If the film thickness of the light-emitting region is 50nm or less, the rise of the driving voltage is easily suppressed.

When the light-emitting region of the organic EL element contains the compound (2), the content thereof is preferably 10% by mass or more, more preferably 20% by mass or more, and still more preferably 30% by mass or more. The present embodiment does not exclude materials other than the compound (2) from being included in the light-emitting region.

(Electron transport region)

The electron transport region is composed of an electron injection layer, an electron transport layer, a hole blocking layer, and the like. Any one of the electron transport regions, particularly the electron transport layer, preferably contains 1 or more selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes containing alkali metals, organic complexes containing alkaline earth metals, and organic complexes containing rare earth metals.

(Electron transport layer)

The electron transport layer is a layer containing a material having high electron transport properties (electron transport material). As the electron-transporting material for the electron-transporting layer, for example, it is possible to use

(1) Metal complexes such as aluminum complex, beryllium complex, zinc complex, etc,

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

(3) A polymer compound.

Examples of the metal complex include: tris (8-hydroxyquinoline) aluminum (III) (abbreviated as Alq), tris (4-methyl-8-hydroxyquinoline) aluminum (abbreviated as Almq 3), bis (10-hydroxybenzo [ h ] ]Quinoline) beryllium (abbreviation: beBq ₂ ) Bis (2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (abbreviation: BAlq), bis (8-hydroxyquinoline) zinc (II) (abbreviation: znq), bis [2- (2-benzoxazolyl) phenol]Zinc (II) (ZnPBO) and bis [2- (2-benzothiazolyl) phenol]Zinc (II) (abbreviated as ZnBTZ).

Examples of the heteroaromatic compound include: 2- (4-Biphenyl) -5- (4-tert-butylphenyl) -1,3, 4-oxadiazole (abbreviated as PBD), 1, 3-bis [5- (p-tert-butylphenyl) -1,3, 4-oxadiazol-2-yl ] benzene (abbreviated as OXD-7), 3- (4-tert-butylphenyl) -4-phenyl-5- (4-biphenyl) -1,2, 4-triazole (abbreviated as TAZ), 3- (4-tert-butylphenyl) -4- (4-ethylphenyl) -5- (4-biphenyl) -1,2, 4-triazole (abbreviated as p-EtTAZ), bathophenanthroline (abbreviated as BPhen), bathocuproine (abbreviated as BCP), 4' -bis (5-methylbenzoxazol-2-yl) stilbene (abbreviated as BzOs).

Examples of the polymer compound include poly [ (9, 9-dihexylfluorene-2, 7-diyl) -co- (pyridine-3, 5-diyl) ] (abbreviated as PF-Py), and poly [ (9, 9-dioctylfluorene-2, 7-diyl) -co- (2, 2 '-bipyridine-6, 6' -diyl) ] (abbreviated as PF-BPy).

The above material has a composition of 10 ^-6 cm ² Electron mobility above/VS. The electron transport layer may be made of a material other than the above materials as long as the electron transport property is higher than the hole transport property.

The electron transport layer may be a single layer or a plurality of layers including 2 or more layers. For example, the electron transport layer may be a layer including a 1 st electron transport layer (anode side) and a 2 nd electron transport layer (cathode side). Each of the 2 or more electron transport layers is formed of the electron transport material.

(Electron injection layer)

The electron injection layer is a layer containing a material having high electron injection properties. As the electron injection layer, alkali metal, alkaline earth metal, or a compound thereof such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2), lithium oxide (LiOx), or the like can be used. In addition, a material having electron-transporting properties may be used, such as a material containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a material containing magnesium (Mg) in Alq. In this case, electron injection from the cathode can be performed more efficiently.

Alternatively, a composite material in which an organic compound and an electron donor (donor) are mixed may be used for the electron injection layer. Such a composite material is excellent in electron injection property and electron transport property because the organic compound accepts electrons from the electron donor. In this case, the organic compound is preferably a material excellent in the transport of the received electrons, and specifically, for example, the above-mentioned material (metal complex, heteroaromatic compound, or the like) constituting the electron transport layer can be used. The electron donor may be any material that exhibits electron donating properties to an organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferable, and examples thereof include lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like. The alkali metal oxide and alkaline earth metal oxide are preferable, and examples thereof include lithium oxide, calcium oxide, and barium oxide. In addition, a Lewis base such as magnesium oxide may be used. In addition, an organic compound such as tetrathiafulvalene (abbreviated as TTF) may be used.

(cathode)

The cathode preferably uses a metal, an alloy, a conductive compound, a mixture thereof, or the like having a small work function (specifically, 3.8eV or less). Specific examples of such cathode materials include alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca) and strontium (Sr), alloys containing the same (for example, mgAg and AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), alloys containing the same, and the like, which belong to the first group or the second group of the periodic table.

When forming a cathode using an alkali metal, an alkaline earth metal, or an alloy containing these metals, a vacuum vapor deposition method or a sputtering method may be used. In addition, when silver paste or the like is used, a coating method, an inkjet method, or the like may be used.

By providing the electron injection layer, the cathode can be formed using a variety of conductive materials such as A1, ag, ITO, graphene, and indium oxide-tin oxide containing silicon or silicon oxide, regardless of the magnitude of the work function. These conductive materials may be formed into films by sputtering, inkjet, spin coating, or the like.

(insulating layer)

Since an electric field is applied to an ultrathin film, a pixel defect due to leakage or short circuit is likely to occur in an organic EL element. In order to prevent this, an insulating layer formed of an insulating thin film layer may be interposed between the pair of electrodes.

Examples of materials that can be used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, and vanadium oxide. It is to be noted that a mixture or a laminate of these may be used.

(spacer layer)

For example, when the fluorescent light-emitting layer and the phosphorescent light-emitting layer are laminated, the spacer layer is a layer provided between the fluorescent light-emitting layer and the phosphorescent light-emitting layer for the purpose of preventing excitons generated in the phosphorescent light-emitting layer from diffusing into the fluorescent light-emitting layer or adjusting carrier balance. In addition, a spacer layer may be disposed between the plurality of phosphorescent light emitting layers. The term "carrier" as used herein means a charge carrier in a substance.

The spacer layer is preferably a material having both electron transport property and hole transport property because it is provided between the light emitting layers. In order to prevent diffusion of triplet energy in adjacent phosphorescent light emitting layers, the triplet energy is preferably 2.6eV or more. As a material for the spacer layer, the same materials as those described above for the hole transport layer can be mentioned.

(Barrier layer)

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 refers to a layer that prevents electrons from leaking from the light emitting layer to the hole transporting layer, and the hole blocking layer refers to a layer that prevents holes from leaking from the light emitting layer to the electron transporting layer. The exciton blocking layer has a function of preventing excitons generated in the light emitting layer from diffusing to a peripheral layer to block the excitons in the light emitting layer.

The film thickness of each layer is not particularly limited, and in general, defects such as pinholes tend to be generated when the film thickness is too small, whereas when the film thickness is too large, a high driving voltage is required and efficiency tends to be poor, and therefore, the film thickness is usually 5nm to 10 μm, more preferably 10nm to 0.2 μm. The thickness of the light-emitting region is as described above.

(layer Forming method)

The method for forming each layer of the organic EL element according to the embodiment of the present invention is not particularly limited, and for example, a known method such as a dry film forming method, e.g., a vacuum vapor deposition method, a molecular beam vapor deposition method (MBE method), a sputtering method, a plasma method, or an ion plating method, a spin coating method, a dip coating method, a flow coating method, a bar coating method, a roll coating method, or an inkjet method, may be used.

< electronic device >)

The organic EL element according to one embodiment of the present invention can be used for electronic devices such as a display device and a light-emitting device. Examples of the display device include a display member such as an organic EL panel module, a television, a mobile phone, a tablet pc, a personal computer, and the like. Examples of the light emitting device include illumination, a vehicle lamp, and the like.

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

< composition >)

The composition of the present invention comprises a compound represented by the above formula (1) and a compound represented by the above formula (2).

The form of the compound represented by the above formula (1) and the compound represented by the above formula (2) is not particularly limited, and examples thereof include solid, powder, solution, film (layer) and the like. Examples of the film (layer) include an organic layer (e.g., a hole injection layer, a hole transport layer, and an electron blocking layer) constituting an organic EL element. In the case where the composition according to an embodiment of the present invention is in a solid or powder form, it may be formed into a pellet form.

When the composition is in the form of powder (mixed powder), the compound represented by the formula (1) and the compound represented by the formula (2) may be contained in one pellet, or the compound may be mixed with the pellet containing the compound represented by the formula (1) and the pellet containing the compound represented by the formula (2).

As a method for producing the mixed powder, for example, the compound represented by the above formula (1) and the compound represented by the above formula (2) may be pulverized and mixed by a mortar or the like, or the compound represented by the above formula (1) and the compound represented by the above formula (2) may be added to a container or the like, heated and melted in a chemically inert atmosphere, cooled to an ambient temperature, and the obtained mixture may be pulverized by a mixer or the like to obtain the powder. In the latter method, the compound represented by the formula (1) and the compound represented by the formula (2) can be mixed at a molecular level, and more uniform vapor deposition can be performed. In addition, mixing unevenness and other defects which may occur during the transfer of the mixed powder can be prevented.

The mixed powder may be formed into a pellet by compression molding.

In one embodiment of the present invention, the composition of the present invention can be used in vapor deposition methods (including vacuum vapor deposition methods), that is, can be applied to all technical fields including vapor deposition of organic compounds into films. The term "usable for vapor deposition (including vacuum vapor deposition)" may be used interchangeably with "vapor deposition (or vacuum vapor deposition)".

Examples

The present invention will be described in further detail with reference to the following examples, which are not intended to limit the scope of the invention.

Compounds (1-1) to (1-6) used in the production of the organic EL elements of examples 1 to 10

[ chemical formula 909]

Compounds (2-1) and (2-3) used in the production of organic EL elements of examples 1 to 10

[ chemical formula 910]

Compounds (1-2) to (1-5) and comparative compounds (1-1) to (1-3) used in the production of the organic EL elements of comparative examples 1 to 7

[ chemical formula 911]

Compound (2-2) and comparative compound (2-1) used in the production of organic EL elements of comparative examples 1 to 7

[ chemical formula 912]

Other Compounds used in the manufacture of organic EL elements of example 1 and comparative example 1

[ chemical formula 913]

Other Compounds used in the manufacture of organic EL elements of examples 2 to 10 and comparative examples 2 to 7

[ chemical formula 914]

[ production of organic EL element ]

Example 1 >

A glass substrate (manufactured by Geomatec Co., ltd.) having an ITO transparent electrode (anode) of 25 mm. Times.75 mm. Times.1.1 mm was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, and then to UV ozone cleaning for 30 minutes. The film thickness of ITO was 130nm.

The cleaned glass substrate with the ITO transparent electrode was mounted on a substrate holder of a vacuum vapor deposition apparatus, and first, a compound HT and a compound HI were co-deposited so as to cover the transparent electrode on the surface on the side where the transparent electrode was formed, thereby forming a hole injection layer having a film thickness of 10 nm. The mass ratio of compound HT to compound HI (HT: HI) was 97:3.

next, a compound HT was deposited on the hole injection layer to form a 1 st hole transport layer having a film thickness of 80 nm.

Then, a compound (1-1) was deposited on the 1 st hole transport layer to form a 2 nd hole transport layer having a film thickness of 10 nm.

Next, a light-emitting layer with a film thickness of 25nm was formed by co-evaporating a compound (2-1) (host material) and a compound BD1 (dopant material) on the 2 nd hole transport layer. The mass ratio of the compound (2-1) to the compound BD1 (compound (2-1): BD 1) was 98:2.

next, a 1 st electron transport layer having a film thickness of 5nm was formed by vapor deposition of a compound HBL on the light-emitting layer.

Next, the 2 nd electron transport layer having a film thickness of 20nm was formed by co-depositing the compounds ET1 and Liq on the 1 st electron transport layer. The mass ratio of the compound ET1 to Liq (ET: liq) is 50:50.

next, liF was deposited on the 2 nd electron transport layer to form an electron injecting electrode having a film thickness of 1 nm.

Then, metal A1 was deposited on the electron-injecting electrode to form a metal cathode having a film thickness of 50 nm.

The layer structure of the organic EL element of example 1 thus obtained is shown below.

ITO (130)/HT: hi=97: 3 (10)/HT (80)/compound (1-1) (10)/compound (2-1): BD1 = 98:2 (25)/HBL (5)/ET 1: liq=50: 50 (20)/LiF (1)/Al (50)

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

Comparative example 1 >

An organic EL device was produced in the same manner as in example 1, except that the compounds (1-1) and (2-1) were used instead of the compounds described in table 1.

Example 2 >

Next, a 1 st hole transport layer having a film thickness of 85nm was formed by vapor deposition of a compound HT on the hole injection layer.

Then, a compound (1-2) was deposited on the 1 st hole transport layer to form a 2 nd hole transport layer having a film thickness of 5 nm.

Next, a light-emitting layer having a film thickness of 20nm was formed by co-vapor deposition of compound (2-1) (host material) and compound BD2 (dopant material) on the 2 nd hole transport layer. The mass ratio of the compound (2-1) to the compound BD2 (compound (2-1): BD 2) was 99:1.

Then, the 2 nd electron transport layer having a film thickness of 31nm was formed by co-depositing the compounds ET2 and Liq on the 1 st electron transport layer. The mass ratio of the compound ET2 to Liq (ET 2: liq) is 50:50.

subsequently, liq was deposited on the 2 nd electron transport layer to form an electron-injecting electrode having a film thickness of 1 nm.

Then, metal Al was deposited on the electron-injecting electrode to form a metal cathode having a film thickness of 80 nm.

ITO (130)/HT: hi=97: 3 (10)/HT (85)/compound (1-2) (5)/compound (2-1): BD2 = 99:1 (20)/HBL (5)/ET 2: liq=50: 50 (31)/Liq (1)/Al (80)

Examples 2 to 10 and comparative examples 2 to 7 >, respectively

An organic EL device was produced in the same manner as in example 2, except that the compounds (1-2) and (2-1) were used instead of the compounds described in table 2.

[ evaluation of organic EL element ]

The external quantum efficiency, driving voltage, and 95% lifetime of the obtained organic EL element were measured.

< determination of External Quantum Efficiency (EQE) >)

The obtained organic EL element was subjected to a current density of 10mA/cm at room temperature ² And performing direct current constant current driving. The external quantum efficiency (%) was obtained from the result of measurement of luminance by a luminance meter (a spectroluminance emitter CS-1000 manufactured by Minolta corporation). The results are shown in tables 1 and 2.

< measurement of drive Voltage >)

For applying a voltage to the organic EL element to have a current density of 10mA/cm ² The voltage (unit: V) at that time was measured. The results are shown in tables 1 and 2.

< determination of 95% lifetime >

The obtained organic EL element was subjected to a current density of 50mA/cm ² Direct current constant current driving is carried out for brightness reductionThe time as short as 90% or 95% of the initial luminance was measured, and the time was set to 90% lifetime (LT 90) or 95% lifetime (LT 95). The results are shown in tables 1 and 2.

TABLE 1

TABLE 2

As is clear from the results of tables 1 and 2, the organic EL element of the present invention including the compound represented by formula (1) and the compound represented by formula (2) in the organic layer exhibits excellent efficiency, low driving voltage, and long life, compared with the organic EL element including the compound that does not satisfy the structural conditions of the present invention.

Compounds (1-1) to (1-6) synthesized in Synthesis examples 1-1 to 1-6

[ chemical formula 915]

/>

Compounds (2-1) and (2-3) synthesized in Synthesis examples 2-1 and 2-2

[ chemical formula 916]

Intermediate synthesis example 1: synthesis of intermediate A

[ chemical formula 917]

(1) Synthesis of intermediate A-1

7.2g of 2, 6-tetramethylpiperidine and 60mL of tetrahydrofuran (dehydrated) were added to the flask under argon atmosphere, and cooled to-43 ℃. 33mL of n-BuLi (1.55M in hexane) was added thereto, followed by stirring at-40℃for 30 minutes. Then cooling to-69 deg.C, adding ⁱ PrO) ₃ After stirring for 5 minutes at-78 ℃, 20mL of a THF solution in which 5.00g of 1-fluoronaphthalene was dissolved was added dropwise thereto, and the mixture was stirred in an ice bath for 10 hours. After the reaction was completed, 1N HCl aq. (100 mL) was added and stirred at room temperature for 1 hour. Then transferred to a separating funnel and extracted with ethyl acetate. The solution was dried over anhydrous magnesium sulfate, concentrated, and washed with hexane to obtain 6.13g (yield: 71%) of (1-fluoronaphthalen-2-yl) boronic acid (intermediate a-1) as a white solid.

(2) Synthesis of intermediate A-2

4.52g of (1-fluoronaphthalen-2-yl) boric acid (intermediate A-1), 4.30g of 2-bromo-1, 3-dimethoxybenzene, 0.91g of tris (dibenzylideneacetone) dipalladium (0), 0.81g of 2-dicyclohexylphosphino-2 ',6' -dimethoxybiphenyl (SPhos), 12.6g of tripotassium phosphate and 10mL of toluene (dehydrated) were charged into a flask under argon atmosphere, and the mixture was heated under reflux and stirred for 7 hours. After cooling to room temperature, the reaction solution was extracted with toluene, and after removing the aqueous layer, the organic layer was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, concentrated, and the residue was purified by silica gel column chromatography to give 4.70g (yield 84%) of 2- (2, 6-dimethoxyphenyl) -1-fluoronaphthalene (intermediate A-2).

(3) Synthesis of intermediate A-3

4.70g of 2- (2, 6-dimethoxyphenyl) -1-fluoronaphthalene (intermediate A-2) and 210mL of methylene chloride (dehydrated) were added to the flask under argon atmosphere, and cooled to 0 ℃. 41mL of a 1.0mol/l boron tribromide methylene chloride solution was added thereto, followed by stirring at room temperature for 4 hours. After the reaction was completed, the solution was cooled to-78℃and carefully deactivated by methanol and further by a sufficient amount of water. The solution was transferred to a separating funnel, extracted with methylene chloride, dried with anhydrous sodium sulfate, and then removed of the original impurities through a short column of silica gel, the solution was concentrated, and the obtained sample was dried at room temperature for 3 hours under vacuum to give 4.00g (94%) of 2- (3-fluoronaphthalen-2-yl) benzene-1, 3-diol (intermediate a-3) as a transparent oil.

(4) Synthesis of intermediate A-4

4.00g of 2- (3-fluoronaphthalen-2-yl) benzene-1, 3-diol (intermediate A-3), 15mL of N-methyl-2-pyrrolidone (dehydrated) and K2CO under argon ₃ 3.26g was added to the flask, followed by stirring at 150℃for 2 hours. After the completion of the reaction, the solution was cooled to room temperature, ethyl acetate (200 mL) was added thereto, and the mixture was transferred to a separating funnel and washed with water. Drying the solution with anhydrous sodium sulfate, and refining with silica gel column chromatography to obtain naphtho [1,2-b ]]1.25g (34% yield) of benzofuran-7-ol (intermediate A-4) as a white solid.

(5) Synthesis of intermediate A

1.25g of naphtho [1,2-b ] benzofuran-7-ol (intermediate A-4), 65mg of N, N-dimethyl-4-aminopyridine, 1.08mL of trifluoromethanesulfonic anhydride, and 27mL of dichloromethane (dehydrated) were added to the flask under argon atmosphere, and the mixture was cooled to 0 ℃. Pyridine (dehydrated) 10.6mL was added dropwise, followed by stirring at room temperature for 2 hours. After the reaction, the reaction mixture was deactivated by a sufficient amount of water. The solution was transferred to a separating funnel, extracted with methylene chloride, dried with anhydrous sodium sulfate, and then removed of the original impurities through a short column of silica gel, the solution was concentrated, and the obtained sample was dried at room temperature for 3 hours under vacuum to give 1.50g (77%) of naphtho [1,2-b ] benzofuran-7-yl triflate (intermediate a) as a white solid.

Intermediate synthesis example 2: synthesis of intermediate B

[ chemical formula 918]

A mixture of 7.33g (20.0 mmol) of intermediate A, 3.75g (24.0 mmol) of 4-chlorophenylboronic acid, [1,1' -bis (diphenylphosphino) ferrocene ] palladium (II) dichloride dichloromethane adduct 0.327g (0.400 mmol), 20mL (40.0 mmol) of 2M aqueous sodium carbonate solution and 66.7mL of DME was stirred at 80℃for 2 hours under argon. The reaction mixture was cooled to room temperature, and water was then added thereto, followed by filtration. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 6.07g of a white solid. The yield was 92%.

Intermediate synthesis example 3: synthesis of intermediate C

[ chemical formula 919]

The same procedure was conducted as in Synthesis example 2, except that 2-chlorobenzoic acid was used instead of 4-chlorobenzoic acid, to obtain a white solid. The yield was 90%.

Intermediate synthesis example 4: synthesis of intermediate D

[ chemical formula 920]

2.9g (16.18 mmol) of intermediate ■ -1 and DMF (55 ml) were mixed under argon and 5.76g (32.4 mmol) of N-bromosuccinimide was added at 0 ℃. Water and ethyl acetate were added to conduct extraction, and the obtained organic layer was distilled under reduced pressure to obtain intermediate ■ -2. Intermediate ■ -2 was used in the next reaction without purification.

6.41g (19.12 mmol) of intermediate ■ -2, 8.22g (47.8 mmol) of 1-naphthylboric acid, 406mg (0.574 mmol) of bis (di-tert-butyl (4-dimethylaminophenyl) phosphine) palladium (II) dichloride and 100ml of 1, 4-dioxane were mixed under argon atmosphere, and an aqueous potassium phosphate solution was added. After heating and stirring at 110℃for 7 hours and cooling, the mixture was filtered and purified by column chromatography and recrystallization to give intermediate ■ (4.9 g). The yield was 71% (2 steps).

Synthesis example 1-1: synthesis of Compound (1-1)

[ chemical formula 921]

A mixture of 2.25g (7.00 mmol) of 4- (1-naphthyl) -N- [4- (1-naphthyl) phenyl ] aniline, 2.53g (7.70 mmol) of intermediate B, 0.128g (0.140 mmol) of tris (dibenzylideneacetone) dipalladium (0), 0.162g (0.56 mmol) of tris (t-butylphosphonium tetrafluoroborate, 0.942g (9.80 mmol) of sodium t-butoxide and 70mL of xylene was stirred at 130℃for 2 hours under argon. The reaction mixture was cooled to room temperature, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 3.51g of a white solid. The yield thereof was found to be 61%.

The mass spectrometry analysis of the obtained substance gave compound (1-1), m/e=714 to molecular weight 713.88.

Synthesis examples 1 to 2: synthesis of Compound (1-2)

[ chemical formula 922]

A mixture of 2.25g (7.00 mmol) of N- [1,1 '-biphenyl ] -4-yl- [1,1' -biphenyl ] -4-amine, 2.53g (7.70 mmol) of intermediate C, 0.128g (0.140 mmol) of tris (dibenzylideneacetone) dipalladium (0), 0.162g (0.56 mmol) of SPhos, 0.942g (9.80 mmol) of sodium tert-butoxide, 70mL of xylene was stirred at 110℃for 2 hours under argon. The reaction mixture was cooled to room temperature, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 3.51g of a white solid. The yield thereof was found to be 82%.

The mass spectrometry analysis of the obtained substance gave compound (1-2), m/e=614, relative to the molecular weight of 613.76.

Synthesis examples 1 to 3: synthesis of Compound (1-3)

[ chemical formula 923]

The same operations were conducted except that N- [4- (1-naphthyl) phenyl ] [1,1' -biphenyl ] -4-amine was used instead of N- [1,1' -biphenyl ] -4-yl- [1,1' -biphenyl ] -4-amine in Synthesis example 1-2, whereby a white solid was obtained. The yield was 89%.

The mass spectrum of the obtained substance showed that compound (1-3) had a molecular weight of 663.82, m/e=664.

Synthesis examples 1 to 4: synthesis of Compound (1-4)

[ chemical formula 924]

The same procedure was repeated except for using 4- (1-naphthyl) -N- [4- (1-naphthyl) phenyl ] aniline instead of N- [1,1 '-biphenyl ] -4-yl- [1,1' -biphenyl ] -4-amine in Synthesis example 1-2 to obtain a white solid. The yield was 64%.

The mass spectrometry analysis of the obtained material gave compound (1-4), m/e=714, relative to the molecular weight 713.88.

Synthesis examples 1 to 5: synthesis of Compound (1-5)

[ chemical formula 925]

A mixture of 4.88g (10.0 mmol) of 4- (1-naphthyl) -N- [4- (1-naphthyl) phenyl ] aniline, 4.03g (11.0 mmol) of intermediate A, 0.183g (0.200 mmol) of tris (dibenzylideneacetone) dipalladium (0), 0.264 g (0.764 mmol) of XPhos, 1.35g (14.0 mmol) of sodium t-butoxide, and 100mL of toluene was stirred at 100℃for 7 hours under argon. The reaction mixture was cooled to room temperature, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 6.41g of a white solid. The yield was 91%.

The mass spectrometry analysis of the obtained material gave compound (1-5), m/e=638, relative to molecular weight 637.78.

Synthesis examples 1 to 6: synthesis of Compound (1-6)

[ chemical formula 926]

The same operations were conducted except that in synthesis examples 1 to 5, intermediate ■ was used instead of 4- (1-naphthyl) -N- [4- (1-naphthyl) phenyl ] aniline, to obtain a white solid.

The mass spectrum of the obtained substance was analyzed to obtain compound (1-6), m/e=646, relative to molecular weight 645.83.

Synthesis example 2-1: synthesis of Compound (2-1)

[ chemical formula 927]

4.09g of [1,2-b ] benzofuran-7-yl triflate (intermediate A), 4.09g of 10-phenylanthracene-9-boric acid, 0.19g of tetrakis (triphenylphosphine) palladium (0), 0.87g of sodium carbonate, 30mL of 1, 4-dioxane and 10mL of ion-exchanged water were added to the flask under argon atmosphere, and the mixture was refluxed and stirred for 4 hours. After cooling to room temperature, the precipitated solid was collected by filtration. The obtained solid was washed with water, then washed with acetone, and recrystallized from a mixed solvent of acetonitrile and hexane to obtain 1.41g of a white solid.

The mass spectrometry analysis of the obtained substance gave compound (2-1), m/e=714 to molecular weight 713.88.

Synthesis example 2-2: synthesis of Compound (2-3)

Methods for synthesizing the compound (2-3) are known from, for example, synthesis examples 1- (7) of International publication No. 2020/153650. Since synthesis can be performed according to a known synthesis technique, a detailed description of a synthesis method is omitted.

Symbol description

1. 11 organic EL element

2. Substrate board

3. Anode

4. Cathode electrode

5. Light-emitting layer

6. Hole transport region (hole transport layer)

6a hole injection layer

6b 1 st hole transport layer

6c No. 2 hole transport layer

7. Electron transport region (electron transport layer)

7a 1 st electron transport layer

7b 2 nd electron transport layer

10. 20 luminous unit

Claims

1. An organic electroluminescent element having a cathode, an anode, and an organic layer between the cathode and the anode, the organic layer comprising a light-emitting layer, the organic layer comprising a compound represented by the following formula (1) and a compound represented by the following formula (2),

in the formula (1), the components are as follows,

N ^＊ is the central nitrogen atom of the silicon atom,

R ¹ ～R ⁸ and R is ¹¹ ～R ¹⁸ Each independently is

A hydrogen atom,

Halogen atom,

Cyano group,

Nitro group,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

Substituted or unsubstituted cycloalkyl having 3 to 50 ring members,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ) A group shown,

-O-(R ₉₀₄ ) A group shown,

-S-(R ₉₀₅ ) A group shown,

-N(R ₉₀₆ )(R ₉₀₇ ) A group shown,

Substituted or unsubstituted aryl groups having 6 to 50 ring members, or

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

R ₉₀₁ ～R ₉₀₇ Each independently is

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted cycloalkyl having 3 to 50 ring members,

Substituted or unsubstituted aryl groups having 6 to 50 ring members, or

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

at R ₉₀₇ When there are 2 or more, 2 or more R ₉₀₇ Are the same as or different from each other,

n is 0 or 1, and the number of the N is not limited,

wherein,,

when n is 0, the number of the n-type organic electroluminescent element,

when n is 1, the number of the n-type organic electroluminescent element,

r is selected from single bonds other than those bound to a and b ¹ ～R ⁴ R is not a single bond to both C and d ⁵ ～R ⁸ 、R ¹¹ ～R ¹⁴ And R is ¹⁵ ～R ¹⁸ 1 of them is a single bond to the ene bond,

X ¹ is an oxygen atom or a sulfur atom,

Ar ¹ and Ar is a group ² Each independently represents a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming carbon atoms,

L ¹ ～L ³ each independently is a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming carbon atoms,

in the formula (2), the amino acid sequence of the compound,

L ¹¹ and L ¹² Each independently is a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming carbon atoms,

Ar ¹¹ is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming carbon atoms,

R ²¹ ～R ²⁸ and R is ³¹ ～R ³⁸ Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms,

X ² Is an oxygen atom, a sulfur atom, or CR ^a R ^b ，

R ^a And R is ^b Is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, R ^a And R is R ^b Optionally bonded to each other to form a substituted or unsubstituted ring,

wherein,,

selected from R other than said single bond ³¹ ～R ³⁸ The adjacent 2 of the two are bonded to each other to form a ring or not.

2. The organic electroluminescent element according to claim 1, wherein,

the organic layer includes a hole transport region between the anode and the light emitting layer, the hole transport region including the compound represented by the formula (1).

3. The organic electroluminescent element according to claim 2, wherein,

the hole transport region includes 2 or more hole transport layers, and at least 1 layer of the hole transport layers includes the compound represented by the formula (1).

4. The organic electroluminescent element as claimed in claim 2 or 3, wherein,

the hole transport region includes 3 or more hole transport layers, and at least 1 layer of the hole transport layers includes the compound represented by the formula (1).

5. The organic electroluminescent element as claimed in claim 3 or 4, wherein,

The layer located at the position closest to the cathode side among the hole transport layers contains the compound represented by the formula (1).

6. The organic electroluminescent element as claimed in any one of claims 1 to 5, wherein,

the compound represented by the formula (1) is a compound represented by any one of the following formulas (1A) to (1C),

in the formulas (1A) to (1C),

N ^＊、R ¹ ～R ⁸ 、R ¹¹ ～R ¹⁴ 、X ¹ 、Ar ¹ 、Ar ² and L ¹ ～L ³ As defined in the formula (1),

wherein,,

when the compound represented by the formula (1) is the formula (1A), R is selected from ³ ～R ⁸ And R is ¹¹ ～R ¹⁴ 1 of them is a single bond to 1,

when the compound represented by the formula (1) is the formula (1B), R is selected from ¹ 、R ⁴ ～R ⁸ And R is ¹¹ ～R ¹⁴ 1 of them is a single bond to an am,

when the compound represented by the formula (1) is the formula (1C), R is selected from ¹ 、R ² 、R ⁵ ～R ⁸ And R is ¹¹ ～R ¹⁴ 1 of them is a single bond to an n.

7. The organic electroluminescent element according to claim 6, wherein,

the compound represented by the formula (1) is a compound represented by the formula (1C).

8. The organic electroluminescent element as claimed in any one of claims 1 to 7, wherein,

the R is ⁸ Is a single bond to the ene.

9. The organic electroluminescent element as claimed in any one of claims 1 to 8, wherein,

L ¹ is a substituted or unsubstituted phenylene group.

10. The organic electroluminescent element as claimed in any one of claims 1 to 9, wherein,

L ¹ is unsubstituted phenylene.

11. The organic electroluminescent element as claimed in any one of claims 1 to 10, wherein,

L ¹ is o-phenylene or p-phenylene.

12. The organic electroluminescent element as claimed in any one of claims 1 to 11, wherein,

the compound represented by the formula (1) is a compound represented by the following formula (1 c),

in the formula (1C), the amino acid sequence,

13. The organic electroluminescent element as claimed in any one of claims 1 to 12, wherein,

X ¹ is an oxygen atom.

14. The organic electroluminescent element as claimed in any one of claims 1 to 13, wherein,

ar of the formula (1) ¹ And Ar is a group ² Each independently is a group represented by any one of the following formulas (1-a) to (1-f),

in Ar ¹ In the case of the following formula (1-a), L ² Is a single bond,

in Ar ² In the case of the following formula (1-a), L ³ Is a single bond,

in Ar ² When the compound is represented by any one of the following formulas (1-b) to (1-f), L ³ Is a single bond or an unsubstituted arylene group having 6 to 30 ring members,

In the formula (1-a),

represents a central nitrogen atom N ^＊ Is used for the bonding position of the (c) and (d),

in the formula (1-b),

R ⁵¹ ～R ⁵⁸ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms,

wherein,,

selected from not said singleR of bond ⁵¹ ～R ⁵⁸ The adjacent 2 of the two are not bonded to each other and thus do not form a ring structure,

representation and L ² Or L ³ Is used for the bonding position of the (c) and (d),

wherein,,

at L ³ When a single bond is used as Ar ² The radicals of the formula (1-b) are represented by the general formula (I) and the central nitrogen atom N ^＊ Is used for the bonding position of the (c) and (d),

in the formula (1-c),

R ⁶¹ ～R ⁷⁰ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms,

wherein,,

selected from R other than said single bond ⁶¹ ～R ⁷⁰ The adjacent 2 of the two are not bonded to each other and thus do not form a ring structure,

wherein,,

at L ³ When a single bond is used as Ar ² The radicals of the formula (1-c) are represented by the general formula (I) and the central nitrogen atom N ^＊ Is used for the bonding position of the (c) and (d),

in the formula (1-d),

R ⁸¹ ～R ⁹² each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms,

wherein,,

selected from R other than said single bond ⁸¹ ～R ⁹² The adjacent 2 of the two are not bonded to each other and thus do not form a ring structure,

wherein,,

at L ³ When a single bond is used as Ar ² The radicals of the formula (1-a) are represented by the general formula (I) and the central nitrogen atom N ^＊ Is used for the bonding position of the (c) and (d),

in the formula (1-e),

R ¹⁰¹ ～R ¹⁰⁸ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 13 ring-forming carbon atoms,

X ³ Is an oxygen atom, a sulfur atom, NR ^c Or CR ^d R ^e ，

R ^d and R is ^e Each independently is a hydrogen atom, a substituted or unsubstituted carbonAlkyl of 1 to 50 or substituted or unsubstituted aryl of 6 to 50 ring-forming carbon atoms, R ^d And R is R ^e Optionally bonded to each other to form a substituted or unsubstituted ring,

wherein,,

selected from R other than said single bond ¹⁰¹ ～R ¹⁰⁸ Optionally bonded to each other to form a substituted or unsubstituted benzene ring,

wherein,,

at L ² When a single bond is used as Ar ¹ The radicals of the formula (1-e) are represented by the general formula (I) and the central nitrogen atom N ^＊ Is used for the bonding position of the (c) and (d),

at L ³ When a single bond is used as Ar ² The radicals of the formula (1-e) are represented by the general formula (I) and the central nitrogen atom N ^＊ Is used for the bonding position of the (c) and (d),

in the formula (1-f),

R ¹²¹ ～R ¹²⁵ and R is ¹³¹ ～R ¹³⁵ Each independently represents a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms,

Wherein,,

selected from R other than said single bond ¹¹¹ ～R ¹¹⁵ The adjacent 2 of the two are not bonded to each other and thus do not form a ring structure,

selected from R ¹²¹ ～R ¹²⁵ And R is ¹³¹ ～R ¹³⁵ Optionally bonded to each other to form a substituted or unsubstituted benzene ring,

wherein,,

15. The organic electroluminescent element as claimed in any one of claims 1 to 13, wherein,

L ² and L ³ Each independently is a single bond, or phenylene.

16. The organic electroluminescent element as claimed in any one of claims 1 to 15, wherein,

the light-emitting layer contains the compound represented by the formula (2).

17. The organic electroluminescent element as claimed in any one of claims 1 to 16, wherein,

the light emitting layer includes 2 or more layers.

18. The organic electroluminescent element as claimed in any one of claims 1 to 17, wherein,

The compound represented by the formula (2) is a compound represented by the following formula (2A),

in the formula (2A), the amino acid sequence of the formula (2A),

19. The organic electroluminescent element as claimed in any one of claims 1 to 17, wherein,

the compound represented by the formula (2) is a compound represented by any one of the following formulas (2B) to (2D),

in the formula (2B), the amino acid sequence,

R ^33b ～R ^38b and R is ¹⁴¹ ～R ¹⁴⁴ Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms,

L ¹¹ 、L ¹² 、Ar ¹¹ 、R ²¹ ～R ²⁸ and X ² As defined in the formula (2),

wherein,,

selected from R ^33b 、R ^36b ～R ^38b 、R ¹⁴¹ ～R ¹⁴⁴ 、R ^a And R is ^b 1 of them is a single bond to 1,

in the formula (2C), the amino acid sequence,

R ^31c 、R ^34c ～R ^38c and R is ¹⁵¹ ～R ¹⁵⁴ Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms,

wherein,,

selected from R ^31c 、R ^34c ～R ^38c 、R ¹⁵¹ ～R ¹⁵⁴ 、R ^a And R is ^b 1 of them is a single bond to an am,

in the formula (2D), the amino acid sequence,

R ^31d 、R ^32d 、R ^36d ～R ^38d and R is ¹⁶¹ ～R ¹⁶⁴ Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms,

wherein,,

20. The organic electroluminescent element according to claim 19, wherein,

the compound represented by the formula (2) is the compound represented by the formula (2D).

21. The organic electroluminescent element according to any one of claims 1 to 20, wherein,

the compound shown in the formula (2) is the compound shown in the formula (2 d),

in the formula (2 d), the amino acid sequence of the compound,

L ¹¹ 、Ar ¹¹ 、R ²¹ ～R ²⁸ and X ² As defined in the formula (2),

22. The organic electroluminescent element according to any one of claims 1 to 21, wherein,

Ar ¹¹ is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

23. The organic electroluminescent element as claimed in any one of claims 1 to 22, wherein,

X ² is an oxygen atom or a sulfur atom.

24. The organic electroluminescent element according to any one of claims 1 to 23, wherein,

X ² is an oxygen atom.

25. The organic electroluminescent element according to any one of claims 1 to 24, wherein,

the compound represented by the formula (1) contains at least 1 deuterium atom.

26. The organic electroluminescent element according to any one of claims 1 to 25, wherein,

the compound represented by the formula (2) contains at least 1 deuterium atom.

27. The organic electroluminescent element according to any one of claims 2 to 26, wherein,

the hole transport region includes a 1 st hole transport layer on the anode side and a 2 nd hole transport layer on the cathode side, and the 2 nd hole transport layer includes the compound represented by the formula (1).

28. The organic electroluminescent element according to any one of claims 1 to 27, wherein,

the light emitting layer includes a fluorescent dopant material.

29. The organic electroluminescent element according to any one of claims 1 to 27, wherein,

the light emitting region includes a phosphorescent dopant material.

30. An electronic device comprising the organic electroluminescent element according to any one of claims 1 to 29.

31. A composition comprising a compound represented by the following formula (1) and a compound represented by the following formula (2),

in the formula (1), the components are as follows,

N ^＊ is the central nitrogen atom of the silicon atom,

R ¹ ～R ⁸ and R is ¹¹ ～R ¹⁸ Each independently is

A hydrogen atom,

Halogen atom,

Cyano group,

Nitro group,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

Substituted or unsubstituted cycloalkyl having 3 to 50 ring members,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ) A group shown,

-O-(R ₉₀₄ ) A group shown,

-S-(R ₉₀₅ ) A group shown,

-N(R ₉₀₆ )(R ₉₀₇ ) A group shown,

Substituted or unsubstituted aryl groups having 6 to 50 ring members, or

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

R ₉₀₁ ～R ₉₀₇ each independently is

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted cycloalkyl having 3 to 50 ring members,

Substituted or unsubstituted aryl groups having 6 to 50 ring members, or

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

n is 0 or 1, and the number of the N is not limited,

wherein,,

when n is 0, the number of the n-type organic electroluminescent element,

when n is 1, the number of the n-type organic electroluminescent element,

X ¹ is an oxygen atom or a sulfur atom,

in the formula (2), the amino acid sequence of the compound,

R ²¹ ～R ²⁸ And R is ³¹ ～R ³⁸ Each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, orSubstituted or unsubstituted aryl groups having 6 to 50 ring-forming carbon atoms,

X ² is an oxygen atom, a sulfur atom, or CR ^a R ^b ，

wherein,,