CN118922399A

CN118922399A - Compound, material for organic electroluminescent element, and electronic device

Info

Publication number: CN118922399A
Application number: CN202380028727.8A
Authority: CN
Inventors: 泽藤司; 糸井裕亮; 高桥佑典; 田中将太; 深见拓人
Original assignee: Idemitsu Kosan Co Ltd
Current assignee: Idemitsu Kosan Co Ltd
Priority date: 2022-03-25
Filing date: 2023-03-22
Publication date: 2024-11-08
Also published as: KR20240165945A; WO2023182323A1

Abstract

A compound represented by the following formula (1), an organic electroluminescent element comprising the compound, and an electronic device comprising the organic electroluminescent element. The symbols in the formula (1) are as defined in the specification.

Description

Compound, material for organic electroluminescent element, and electronic device

Technical Field

The present invention relates to a compound, a material for an organic electroluminescent element, and an electronic device including the organic electroluminescent element.

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 develop a material that efficiently transports electrons or holes to a light-emitting region and allows electrons and holes to be easily recombined, 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: japanese patent application laid-open No. 2017-022195

Patent document 2: U.S. patent application publication No. 2018/0331290 specification

Patent document 3: U.S. patent application publication No. 2019/0237688 specification

Patent document 4: U.S. patent application publication No. 2019/0237676 specification

Patent document 5: U.S. patent application publication 2020/0303647 specification

Patent document 6: chinese patent application publication No. 113683519

Patent document 7: chinese patent application publication No. 113683603

Patent document 8: chinese patent application publication No. 113717059

Patent document 9: chinese patent application publication No. 113735719

Patent document 10: korean patent laid-open publication No. 10-2292406

Disclosure of Invention

Problems to be solved by the invention

A large number of compounds for organic EL elements have been reported in the past, but compounds for further improving the performance of organic EL elements have been still sought.

The present invention has been made to solve the above-described problems, and an object of the present invention is to provide a compound that further improves the performance of an organic EL element, an organic EL element with further improved element performance, 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 novel compounds disclosed in patent documents 1 to 10, and as a result, have found that the performance of an organic EL element comprising a compound represented by the following formula (1) is further improved.

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

[ Chemical formula 1]

In the formula (1) of the formula (I),

N is a central nitrogen atom.

R ¹～R⁶ is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms, or an unsubstituted aryl group having 6 to 18 ring-forming carbon atoms. Wherein 1 or more groups selected from the group consisting of 2 or more adjacent groups of R ¹～R⁶ may be bonded to each other to form 1 or more unsubstituted benzene rings, or may not be bonded to each other to form a ring.

Ar ³ is an aryl group having 6 to 18 ring-forming carbon atoms which is substituted or unsubstituted, an alkyl group having 1 to 10 carbon atoms which is unsubstituted, or a cycloalkyl group having 3 to 10 ring-forming carbon atoms which is substituted or unsubstituted.

R ¹¹～R¹⁴ is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms, or an unsubstituted aryl group having 6 to 18 ring-forming carbon atoms. Wherein 1 or more groups selected from the group consisting of 2 or more adjacent groups of R ¹¹～R¹⁴ may be bonded to each other to form 1 or more unsubstituted benzene rings, or may not be bonded to each other to form a ring.

L ¹ and L ² are each independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group. Wherein the substituent of the substituted phenylene group, the substituted naphthylene group, and the substituted biphenylene group is an unsubstituted alkyl group having 1 to 6 carbon atoms or an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, and a ring is not fused to the phenylene group, the biphenylene group, and the naphthylene group.

Ar ¹ and Ar ² are each independently a group represented by the following formula (1 a), or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, the aryl group having 6 to 30 ring-forming carbon atoms containing only a six-membered ring, and the substituent in the substituted aryl group having 6 to 30 ring-forming carbon atoms is at least 1 selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms and a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms.

Wherein, when 2 or more atoms of the ring-forming carbon atoms of the aryl group having 6 to 30 ring-forming carbon atoms are substituted with an alkyl group, the 2 or more alkyl groups are not bonded to each other and thus do not form a ring.

[ Chemical formula 2]

(In the formula (1 a),

*1 Is a bonding position to one or both of L ¹ and L ²;

x is an oxygen atom, a sulfur atom, NRa, or CRbRc;

Ra 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;

Rb and Rc are each independently 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;

Wherein Rb and Rc may be bonded to each other to form a ring structure having 8 or more ring atoms, or may not be bonded to each other to form a ring structure;

R21 to R ²⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms;

Wherein 1 selected from the group consisting of R21 to R ²⁸, rb, and Rc is a single bond to a, ra is not bonded to a;

Adjacent 2 of R21 to R ²⁸ selected from the group consisting of single bonds other than the above-mentioned bond with a are not bonded to each other and thus do not form a ring. ) ]

In another embodiment, the present invention provides a material for an organic EL element comprising the compound represented by the above formula (1).

In still another aspect, the present invention provides an organic electroluminescent element comprising an anode, a cathode, and an organic layer between the anode and the cathode, the organic layer comprising a light-emitting layer, at least 1 layer of the organic layer comprising a compound represented by the above formula (1).

In still another aspect, the present invention provides an electronic device including the above-described organic electroluminescent element.

ADVANTAGEOUS EFFECTS OF INVENTION

The organic EL element containing the compound represented by the above formula (1) 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 diagram 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. Unless otherwise indicated, each substituent described in the present specification is defined as follows.

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,

Naphthylphenyl group

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 containing at least 1 hetero atom in the 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 this 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, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, indolizinyl, quinolizinyl, quinolinyl, and isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, indazolyl, phenanthroline yl phenanthridinyl, acridinyl, phenazinyl, carbazolyl, benzocarbazolyl, morpholinyl, phenoxazinyl,

Phenothiazinyl group,

Azacarbazolyl group and diazacarbazolyl.

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

Oxazolyl group,

Isoxazolyl radical,

Oxadiazolyl group,

Xanthyl group,

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), dibenzothiophene (dibenzothienyl),

Naphthacene thienyl (naphthobenzothienyl),

Benzothiazolyl group,

Benzisothiazolyl group,

Phenothiazinyl group,

Dinaphthiophene radical (dinaphthothienyl),

Azadibenzo-p thienyl (azadibenzothienyl),

Diazadibenzo-based compounds thienyl (diazadibenzothienyl),

Azanaphthobenzo thienyl (azanaphthobenzothienyl)

Naphthyridine benzofurans and thienyl (diazanaphthobenzothienyl).

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 are each independently an oxygen atom, a sulfur atom, NH or CH ₂. Wherein at least 1 of X _A and Y _A is an oxygen atom, a sulfur atom or NH.

In the general formulae (TEMP-16) to (TEMP-33), when at least one of X _A and Y _A is NH or CH ₂, the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing 1 hydrogen atom from the NH or CH ₂.

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 and

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 "1 or more hydrogen atoms of a monovalent heterocyclic group" means 1 or more hydrogen atoms selected from the group consisting of hydrogen atoms bonded to ring-forming carbon atoms of the monovalent heterocyclic group, hydrogen atoms bonded to nitrogen atoms when at least one of X _A and Y _A is NH, and hydrogen atoms of a methylene group when one of X _A and Y _A is CH ₂.

"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.

Radicals "shown in" -Si (R ₉₀₁₎(R₉₀₂)(R₉₀₃) "

Specific examples of the group represented by-Si (R ₉₀₁₎(R₉₀₂)(R₉₀₃) described in the present specification (group G7) include

-Si(G1)(G1)(G1)、

-Si(G1)(G2)(G2)、

-Si(G1)(G1)(G2)、

-Si(G2)(G2)(G2)、

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

Si (G6) (G6) (G6). 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.

Radical "-O- (R ₉₀₄)" as indicated "

Specific examples of the group represented by-O- (R ₉₀₄) described in the present specification (group G8) include

-O(G1)、

-O(G2)、

-O (G3) and

-O(G6)。

Here the number of the elements is the number,

"Group represented by S- (R ₉₀₅)":

Specific examples of the group represented by-S- (R ₉₀₅) described in the present specification (group G9) include

-S(G1)、

-S(G2)、

-S (G3) and

-S(G6)。

Here the number of the elements is the number,

"Group represented by N (R ₉₀₆)(R₉₀₇)":

Specific examples of the group represented by-N (R ₉₀₆)(R₉₀₇) described in the present specification (group G10) include

-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～Q1₀ is each independently 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～Q1₀ is each independently a hydrogen atom or a substituent.

Formulas Q ₉ and Q1 ₀ may be bonded to each other via a single bond to form a ring.

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～Q₈ is each independently 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～Q₉ is each independently a hydrogen atom or a substituent.

[ Chemical formula 17]

[ Chemical formula 18]

[ Chemical formula 19]

[ Chemical formula 20]

In the general formulae (TEMP-83) to (TEMP-102), Q ₁～Q₈ is each independently 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 … adjacent 2 or more 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, or are not bonded to each other" refers to the "1 or more groups of … adjacent 2 or more groups are bonded to each other to form a substituted or unsubstituted single ring", the "1 or more groups of … adjacent 2 or more groups are bonded to each other to form a substituted or unsubstituted condensed ring", and the "1 or more groups of … adjacent 2 or more groups 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 where 1 or more groups of "adjacent 2 or more groups of R ₉₂₁～R₉₃₀ are bonded to each other to form a ring", the group of 2 adjacent groups of 1 means that the group of R ₉₂₁ and R ₉₂₂, the group of R ₉₂₂ and R ₉₂₃, a group of R ₉₂₃ and R ₉₂₄, a group of R ₉₂₄ and R ₉₃₀, a group of R ₉₃₀ and R ₉₂₅, A group of R ₉₂₅ and R ₉₂₆, a group of R ₉₂₆ and R ₉₂₇, a group of R ₉₂₇ and R ₉₂₈, A group of R ₉₂₈ and R ₉₂₉, and a group of R ₉₂₉ and R ₉₂₁.

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

[ Chemical formula 22]

The case where "a group of 2 or more adjacent groups" forms a ring includes not only the case where a group of 2 or more adjacent groups is bonded as in the foregoing example, but also the case where a group of 3 or more adjacent groups is bonded. For example, R ₉₂₁ and R ₉₂₂ are bonded to each other to form a ring Q _A, and R ₉₂₂ and R ₉₂₃ are bonded to each other to form a ring Q _v, and 3 groups (R ₉₂₁、R₉₂₂ and R ₉₂₃) adjacent to each other are bonded to each other to form a ring and condensed on an anthracene skeleton, and in this case, an anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), R ₉₂₂ is shared by the ring Q _A and the ring Q _C.

[ 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 _A and the ring Q _B formed in the above general formula (TEMP-104) are each a "single ring" or a "condensed ring". In addition, the ring Q _A and the ring Q _C formed in the above general formula (TEMP-105) are "condensed rings". The rings Q _A and Q _C of the general formula (TEMP-105) are fused to form a fused ring by the ring Q _A and the ring Q _C. If ring Q _A of the above general formula (TEMP-104) is a benzene ring, ring Q _A is a single ring. If the ring Q _A of the general formula (TEMP-104) is a naphthalene ring, the 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, the ring Q _A formed by bonding R ₉₂₁ and R ₉₂₂ shown by the general formula (TEMP-104) refers to a ring formed by the carbon atom of the anthracene skeleton bonded by R ₉₂₁ and the carbon atom of the anthracene skeleton bonded by R ₉₂₂ and 1 or more optional elements. Specifically, in the case where R ₉₂₁ and R ₉₂₂ form a ring Q _A, when a monocyclic unsaturated ring is formed by a carbon atom of an anthracene skeleton to which R ₉₂₁ is bonded, a carbon atom of an anthracene skeleton to which R ₉₂₂ is bonded, and 4 carbon atoms, the ring formed by R ₉₂₁ and R ₉₂₂ 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(R₉₀₁)(R₉₀₂)(R₉₀₃)、

-O-(R₉₀₄)、

-S-(R₉₀₅)、

-N(R₉₀₆)(R₉₀₇)、

Halogen atom, cyano group, nitro group,

Unsubstituted aryl group having 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 ₉₀₁～R₉₀₇ are each independently

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.

In the case where R ₉₀₁ is present in an amount of 2 or more, 2 or more R ₉₀₁ are the same or different from each other,

In the case where R ₉₀₂ is present in an amount of 2 or more, 2 or more R ₉₀₂ are the same or different from each other,

In the case where R ₉₀₃ is present in an amount of 2 or more, 2 or more R ₉₀₃ are the same or different from each other,

In the case where R ₉₀₄ is present in an amount of 2 or more, 2 or more R ₉₀₄ are the same or different from each other,

In the case where R ₉₀₅ is present in an amount of 2 or more, 2 or more R ₉₀₅ are the same or different from each other,

In the case where R ₉₀₆ is present in an amount of 2 or more, 2 or more R ₉₀₆ are the same or different from each other,

In the case where there are 2 or more R ₉₀₇, 2 or more R ₉₀₇ are the same 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 compounds of the present invention will be described below.

As described above, the compound according to one embodiment of the present invention is represented by the following formula (1).

The compound of the present invention represented by the following formula contained in formula (1) may be referred to as an "invention compound".

[ Chemical formula 24]

The following description will be given of the symbols in the formula (1) and the formulae included in the formula (1) described below. Like symbols have the same meaning as long as they are not specifically mentioned.

In formula (1), N is a central nitrogen atom.

In the formula (1), R ¹～R⁶ is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms, or an unsubstituted aryl group having 6 to 18 ring-forming carbon atoms. Wherein 1 or more groups selected from the group consisting of 2 or more adjacent groups of R ¹～R⁶ may be bonded to each other to form 1 or more unsubstituted benzene rings, or may not be bonded to each other to form a ring.

Examples of the unsubstituted alkyl group having 1 to 10 carbon atoms which may be represented by R ¹～R⁶ include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl; preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl or hexyl; more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl; further preferred is methyl or tert-butyl; still more preferably t-butyl.

Examples of the unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms which may be represented by R ¹～R⁶ include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-norbornyl, 2-norbornyl, 1-adamantyl and 2-adamantyl; preferably cyclohexyl, 1-norbornyl, 2-norbornyl, 1-adamantyl or 2-adamantyl; more preferably cyclohexyl, 1-adamantyl or 2-adamantyl; further preferred is a cyclohexyl group or a 1-adamantyl group.

Examples of the unsubstituted aryl group having 6 to 18 ring-forming carbon atoms which may be represented by R ¹～R⁶ include phenyl, biphenyl, terphenyl, biphenylenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, benzophenanthryl, phenalenenyl, pyrenyl, and,A group, fluorenyl, fluoranthenyl, or triphenylenyl group; preferably phenyl, biphenyl, terphenyl or naphthyl; more preferably phenyl, 2-biphenyl, 3-biphenyl or 4-biphenyl, 2-o-terphenyl, 3-o-terphenyl or 4-o-terphenyl, 2-m-terphenyl, 3-m-terphenyl or 4-m-terphenyl, 2-p-terphenyl, 3-p-terphenyl or 4-p-terphenyl, or 1-naphthyl or 2-naphthyl; further preferred is phenyl, 2-biphenyl, 3-biphenyl or 4-biphenyl, or 1-naphthyl or 2-naphthyl; even more preferred is phenyl.

In the formula (1), ar ³ is an aryl group having 6 to 18 ring-forming carbon atoms which is substituted or unsubstituted by an alkyl group, an alkyl group having 1 to 10 carbon atoms which is unsubstituted or a cycloalkyl group having 3 to 10 ring-forming carbon atoms which is substituted or unsubstituted.

Examples of the unsubstituted aryl group having 6 to 18 ring-forming carbon atoms which may be represented by Ar ³ include the same groups as the unsubstituted aryl group having 6 to 18 ring-forming carbon atoms which may be represented by R ¹～R⁶; preferably phenyl, biphenyl, terphenyl, or naphthyl; more preferably phenyl, 2-biphenyl, 3-biphenyl or 4-biphenyl, 2-o-terphenyl, 3-o-terphenyl or 4-o-terphenyl, 2-m-terphenyl, 3-m-terphenyl or 4-m-terphenyl, 2-p-terphenyl, 3-p-terphenyl or 4-p-terphenyl, or 1-naphthyl or 2-naphthyl; further preferred is phenyl, 2-biphenyl, 3-biphenyl or 4-biphenyl, or 1-naphthyl or 2-naphthyl; even more preferred is phenyl.

Examples of the alkyl group which may be substituted on the unsubstituted aryl group having 6 to 18 ring-forming carbon atoms represented by Ar ³ include the same groups as the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R ¹～R⁶; preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or pentyl; more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl; further preferred is methyl or tert-butyl; still more preferably t-butyl.

Examples of the unsubstituted alkyl group having 1 to 10 carbon atoms which may be represented by Ar ³ include the same groups as the unsubstituted alkyl group having 1 to 10 carbon atoms which may be represented by R ¹～R⁶; preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl or hexyl; more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl; methyl or tert-butyl is further preferred.

Examples of the unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms which may be represented by Ar ³ include the same groups as the unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms which may be represented by R ¹～R⁶; preferably cyclohexyl, 1-norbornyl, 2-norbornyl, 1-adamantyl or 2-adamantyl; more preferably cyclohexyl, 1-adamantyl or 2-adamantyl; further preferred is a cyclohexyl group or a 1-adamantyl group.

In the formula (1), R ¹¹～R¹⁴ is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms, or an unsubstituted aryl group having 6 to 18 ring-forming carbon atoms. Wherein 1 or more groups selected from the group consisting of 2 or more adjacent groups of R ¹¹～R¹⁴ may be bonded to each other to form 1 or more unsubstituted benzene rings, or may not be bonded to each other to form a ring.

Examples of the unsubstituted alkyl group having 1 to 10 carbon atoms which may be represented by R ¹¹～R¹⁴ include the same groups as the unsubstituted alkyl group having 1 to 10 carbon atoms which may be represented by R ¹～R⁶; preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl or hexyl; more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl; further preferred is methyl or tert-butyl; still more preferably t-butyl.

Examples of the unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms which may be represented by R ¹¹～R¹⁴ include the same groups as the unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms which may be represented by R ¹～R⁶; preferably cyclohexyl, 1-norbornyl, 2-norbornyl, 1-adamantyl or 2-adamantyl; more preferably cyclohexyl, 1-adamantyl or 2-adamantyl; further preferred is a cyclohexyl group or a 1-adamantyl group.

Examples of the unsubstituted aryl group having 6 to 18 ring-forming carbon atoms which may be represented by R ¹¹～R¹⁴ include the same groups as the unsubstituted aryl group having 6 to 18 ring-forming carbon atoms which may be represented by R ¹～R⁶; preferably phenyl, biphenyl, terphenyl, or naphthyl; more preferably phenyl, 2-biphenyl, 3-biphenyl or 4-biphenyl, 2-o-terphenyl, 3-o-terphenyl or 4-o-terphenyl, 2-m-terphenyl, 3-m-terphenyl or 4-m-terphenyl, 2-p-terphenyl, 3-p-terphenyl or 4-p-terphenyl, or 1-naphthyl or 2-naphthyl; further preferred is phenyl, 2-biphenyl, 3-biphenyl or 4-biphenyl, or 1-naphthyl or 2-naphthyl; even more preferred is phenyl.

In formula (1), L ¹ and L ² are each independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group. Wherein the substituent of the substituted phenylene group, the substituted naphthylene group, and the substituted biphenylene group is an unsubstituted alkyl group having 1 to 6 carbon atoms or an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, and a ring is not fused to the phenylene group, the biphenylene group, and the naphthylene group.

The above unsubstituted phenylene groups that L ¹ and L ² may represent are ortho-phenylene, meta-phenylene or para-phenylene.

The above unsubstituted naphthylene group which L ¹ and L ² may represent is preferably a 1, 4-naphthylene group or a 2, 6-naphthylene group.

The above unsubstituted biphenylene group which L ¹ and L ² may represent is preferably 4,4 '-biphenylene group or 3,4' -biphenylene group.

The unsubstituted alkyl group having 1 to 6 carbon atoms which can be used as the substituent of the substituted phenylene group, the substituted naphthylene group or the substituted biphenylene group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl; more preferably methyl, ethyl, isopropyl or tert-butyl; further preferred is methyl or tert-butyl; still more preferably t-butyl.

The aryl group having 6 to 12 unsubstituted ring-forming carbon atoms which can be the substituent of the substituted phenylene group, the substituted naphthylene group or the substituted biphenylene group is preferably phenyl group, biphenyl group or naphthyl group; more preferably phenyl or naphthyl; further preferred is phenyl.

In the formula (1), ar ¹ and Ar ² are each independently a group represented by the following formula (1 a), or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, the aryl group having 6 to 30 ring-forming carbon atoms containing only a six-membered ring, and the substituent in the substituted aryl group having 6 to 30 ring-forming carbon atoms is at least 1 selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms and a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms. Wherein, when 2 or more atoms of the ring-forming carbon atoms of the aryl group having 6 to 30 ring-forming carbon atoms are substituted with an alkyl group, the 2 or more alkyl groups are not bonded to each other and thus do not form a ring.

[ Chemical formula 25]

In formula (1 a), x1 is a bonding position to one or both of L ¹ and L ²;

In the formula (1 a), X is an oxygen atom, a sulfur atom, NRa, or CRbRc;

The unsubstituted alkyl group having 1 to 6 carbon atoms which Ra may represent is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl; more preferably methyl, ethyl, isopropyl or tert-butyl; methyl or tert-butyl is further preferred.

The unsubstituted aryl group having 6 to 12 ring-forming carbon atoms which Ra may represent is preferably phenyl, biphenyl or naphthyl; more preferably phenyl or naphthyl; further preferred is phenyl.

The unsubstituted aromatic heterocyclic group having 5 to 13 ring members which Ra may represent 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), a dibenzofuryl group or a dibenzothienyl group (dibenzothienyl).

Among them, ra is more preferably an unsubstituted phenyl group or an unsubstituted naphthyl group (1-naphthyl group or 2-naphthyl group).

Examples of the unsubstituted alkyl group having 1 to 30 carbon atoms which may be represented by Rb and Rc include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl; preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl or hexyl; more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl; methyl or tert-butyl is further preferred.

Examples of the unsubstituted aryl group having 6 to 30 ring-forming carbon atoms which may be represented by Rb and Rc include phenyl, biphenyl, terphenyl, biphenylenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, benzophenanthryl, phenalenenyl, alizarin, pentylphenyl, pyrenyl,Radical, benzoA group, fluorenyl, fluoranthenyl, perylenyl or triphenylenyl; preferably phenyl, biphenyl, terphenyl, or naphthyl; more preferably phenyl, 2-biphenyl, 3-biphenyl or 4-biphenyl, 2-o-terphenyl, 3-o-terphenyl or 4-o-terphenyl, 2-m-terphenyl, 3-m-terphenyl or 4-m-terphenyl, 2-p-terphenyl, 3-p-terphenyl or 4-p-terphenyl, or 1-naphthyl or 2-naphthyl; further preferred is phenyl, 2-biphenyl, 3-biphenyl or 4-biphenyl, or 1-naphthyl or 2-naphthyl; even more preferred is phenyl.

Examples of the substituent of the unsubstituted alkyl group having 1 to 30 carbon atoms which may be represented by Rb and Rc include optional substituents described below.

Examples of the substituent of the unsubstituted aryl group having 6 to 30 ring-forming carbon atoms which may be represented by Rb and Rc include optional substituents described below, and among these, an alkyl group having 1 to 6 carbon atoms is preferable; more preferably t-butyl.

In other words, when at least one of Rb and Rc is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, rb and Rc may be bonded to each other to form a ring, or may not be bonded to each other to form a ring structure; when Rb and Rc are both a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or any one of Rb and Rc is a hydrogen atom and the other is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, rb and Rc may be bonded to each other to form a ring structure having 8 or more ring atoms, or may not be bonded to each other to form a ring structure;

Here, when Rb and Rc are bonded to each other to form a ring structure having 8 or more ring atoms, the number of ring atoms also includes the carbon atom at the 9-position of the fluorene skeleton. In addition, for example, when the ring structure formed is an adamantane ring structure, the number of ring-forming atoms is 10. That is, the number of ring-forming atoms of the above-described ring structure formed by bonding Rb and Rc to each other also includes atoms which crosslink atoms in 1 ring or in a plurality of rings with each other and which themselves are part of atoms forming one closed ring. On the other hand, atoms which do not form a closed ring and are not incorporated in the ring structure, for example, atoms included in substituents which any one of the atoms forming the ring has are not included in the number of ring-forming atoms described above.

Examples of the ring structure having 8 or more ring atoms, which may be formed by bonding Rb and Rc to each other, include the ring structures shown below, but are not limited to. In the following ring structures, the bonding positions to the benzene rings of the fluorene skeleton are shown.

[ Chemical formula 26]

In the formula (1 a), R ²¹～R²⁸ is independently a hydrogen atom, a substituted or unsubstituted alkyl group with 1 to 10 carbon atoms or a substituted or unsubstituted aryl group with 6 to 12 ring-forming carbon atoms;

Examples of the unsubstituted alkyl group having 1 to 10 carbon atoms which may be represented by R ²¹～R2⁸ include the same groups as the unsubstituted alkyl group having 1 to 10 carbon atoms which may be represented by R ¹～R⁶; preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl or hexyl; more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl; methyl or tert-butyl is further preferred.

The above-mentioned unsubstituted aryl group having 6 to 12 ring-forming carbon atoms which R ²¹～R²⁸ may represent is preferably phenyl, biphenyl or naphthyl; more preferably phenyl or naphthyl; further preferred is phenyl.

The biphenyl group includes an o-biphenyl group, an m-biphenyl group and a p-biphenyl group; preferably m-biphenyl or p-biphenyl; more preferably p-biphenyl.

The above naphthyl group includes 1-naphthyl group and 2-naphthyl group; 1-naphthyl is preferred.

Wherein 1 selected from the above R ²¹～R²⁸, rb and Rc is a single bond to a, ra is not bonded to a;

Adjacent 2 of R ²¹～R²⁸ selected from those other than the single bond with a are not bonded to each other and thus do not form a ring.

In one embodiment of the above-described inventive compound, the group represented by the formula (1 a) is more specifically a group represented by the following formula (1 a-1), formula (1 a-2), formula (1 a-3), or formula (1 a-4).

[ Chemical formula 27]

[ Chemical formula 28]

[ Chemical formula 29]

[ Chemical formula 30]

In the formulae (1 a-1), (1 a-2), (1 a-3) and (1 a-4), 1, a, ra, rb, rc and R ²¹～R²⁸ are as defined in the above formula (1 a), and preferred embodiments thereof are the same.

Among the above-mentioned substituted or unsubstituted aryl groups of 6 to 30 ring-forming carbon atoms which Ar ¹ and Ar ² may represent, the aryl group of 6 to 30 ring-forming carbon atoms contains only a six-membered ring, and the above-mentioned substituent in the above-mentioned substituted aryl group of 6 to 30 ring-forming carbon atoms is at least 1 selected from the group consisting of a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms and a substituted or unsubstituted aryl group of 6 to 12 ring-forming carbon atoms. Wherein, when 2 or more atoms of the ring-forming carbon atoms of the aryl group having 6 to 30 ring-forming carbon atoms are substituted with an alkyl group, the 2 or more alkyl groups are not bonded to each other and thus do not form a ring.

Examples of the unsubstituted aryl group having 6 to 30 ring-forming carbon atoms which may be represented by Ar ¹ and Ar ² include the same groups as the unsubstituted aryl group having 6 to 30 ring-forming carbon atoms which may be represented by Rb and Rc; preferably phenyl, biphenyl, terphenyl, naphthyl, or phenanthryl.

Examples of the unsubstituted alkyl group having 1 to 10 carbon atoms which may be substituted on the unsubstituted aryl group having 6 to 30 carbon atoms having a ring formation which may be represented by Ar ¹ and Ar ² include the same groups as the unsubstituted alkyl group having 1 to 10 carbon atoms which may be represented by R ¹～R⁶; preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl or hexyl; more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl; more preferably a methyl group or a tert-butyl group, and still more preferably a tert-butyl group.

The aryl group having 6 to 12 unsubstituted ring-forming carbon atoms substituted on the aryl group having 6 to 30 unsubstituted ring-forming carbon atoms which may be represented by Ar ¹ and Ar ² is preferably phenyl, biphenyl or naphthyl; more preferably phenyl or naphthyl; further preferred is phenyl.

In one embodiment of the above-described inventive compound, in the formula (1), ar ¹ and Ar ² are each independently preferably a group represented by the following formula (1 a), a group represented by (1 b), a group represented by (1 c), a group represented by (1 d), or a group represented by (1 e).

[ Chemical formula 31]

In formula (1 a), 1, a, X and R ²¹～R²⁸ are as defined in formula (1 a), and the preferred embodiments are the same.

[ Chemical formula 32]

In formula (1 b), x 21 is a bonding position to one or both of L ¹ and L ²;

In formula (1 b), 1 selected from R ¹⁰¹～R¹⁰⁵ is a single bond with x 22, and 1 selected from R ¹⁰⁶～R¹¹⁰ is a single bond with x 23;

R ¹⁰¹～R¹⁰⁵ and R ¹⁰⁶～R¹¹⁰ which are not the above single bonds are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms;

Adjacent 2 selected from R ¹⁰¹～R¹⁰⁵ which is not the above single bond are not bonded to each other and thus do not form a ring;

Adjacent 2 selected from R ¹⁰⁶～R¹¹⁰ which is not the above single bond are not bonded to each other and thus do not form a ring;

Examples of the unsubstituted alkyl group having 1 to 10 carbon atoms which may be represented by R ¹⁰¹～R¹⁰⁵ and R ¹⁰⁶～R¹¹⁰ other than the single bond include the same groups as the unsubstituted alkyl group having 1 to 10 carbon atoms which may be substituted on the unsubstituted aryl group having 6 to 30 ring-forming carbon atoms which may be represented by Ar ¹ and Ar ²; the preferred embodiment is also the same.

Examples of the aryl group having 6 to 12 unsubstituted ring-forming carbon atoms which may be represented by R ¹⁰¹～R¹⁰⁵ and R ¹⁰⁶～R¹¹⁰ other than the single bond include the same aryl groups having 6 to 12 unsubstituted ring-forming carbon atoms which may be substituted on the aryl group having 6 to 30 unsubstituted ring-forming carbon atoms which may be represented by Ar ¹ and Ar ²; the preferred embodiment is also the same.

In the formula (1 b), R ¹¹¹～R¹¹⁵ is independently a hydrogen atom, a substituted or unsubstituted alkyl group with 1 to 10 carbon atoms or a substituted or unsubstituted aryl group with 6 to 12 ring-forming carbon atoms;

Wherein adjacent 2 selected from R ¹¹¹～R¹¹⁵ are not bonded to each other and thus do not form a ring;

Examples of the unsubstituted alkyl group having 1 to 10 carbon atoms which may be represented by the above R ¹¹¹～R¹¹⁵ include the same groups as the unsubstituted alkyl group having 1 to 10 carbon atoms which may be substituted on the unsubstituted aryl group having 6 to 30 ring-forming carbon atoms which may be represented by Ar ¹ and Ar ²; the preferred embodiment is also the same.

Examples of the aryl group having 6 to 12 unsubstituted ring-forming carbon atoms which may be represented by the above-mentioned R ¹¹¹～R¹¹⁵ include the same groups as the aryl group having 6 to 12 unsubstituted ring-forming carbon atoms which may be substituted on the aryl group having 6 to 30 unsubstituted ring-forming carbon atoms which may be represented by Ar ¹ and Ar ²; the preferred embodiment is also the same.

In the formula (1 b), m is 0 or 1, and n is 0 or 1;

wherein,

When m and n are 0, 23 represents a bonding position to one or both of L ¹ and L ²,

Where m is 0 and n is 1, 22 represents a bonding position to one or both of L ¹ and L ²,

When m is 1 and n is 0, 1 selected from R ¹⁰¹～R¹⁰⁵ is a single bond to 23.

The group represented by the above formula (1 b) includes each group represented by the following formula. Wherein, in the following formula, R ¹⁰¹～R¹⁰⁵、R¹⁰⁶～R¹¹⁰ and R ¹¹¹～R¹¹⁵ which are not single bonds are omitted for simplicity.

[ Chemical formula 33]

[ Chemical formula 34]

In formula (1 c), 24 is a bonding position to one or both of L ¹ and L ²;

in the formula (1 c), R ¹²¹～R¹²⁸ is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms;

wherein 1 selected from R ¹²¹～R¹²⁸ is a single bond with x 25, and 2 adjacent selected from R ¹²¹～R¹²⁸ which is not a single bond with x 25 are not bonded to each other, and thus do not form a ring.

Examples of the unsubstituted alkyl group having 1 to 10 carbon atoms which may be represented by R ¹²¹～R¹²⁸ other than the single bond include the same groups as the unsubstituted alkyl group having 1 to 10 carbon atoms which may be substituted on the unsubstituted aryl group having 6 to 30 ring-forming carbon atoms which may be represented by Ar ¹ and Ar ²; the preferred embodiment is also the same.

Examples of the aryl group having 6 to 12 unsubstituted ring-forming carbon atoms which may be represented by R ¹²¹～R¹²⁸ other than the single bond include the same aryl groups having 6 to 12 unsubstituted ring-forming carbon atoms which may be substituted on the aryl group having 6 to 30 unsubstituted ring-forming carbon atoms which may be represented by Ar ¹ and Ar ²; the preferred embodiment is also the same.

[ Chemical formula 35]

In formula (1 d), 26 is a bonding position to one or both of L ¹ and L ²;

In the formula (1 d), R ¹³¹～R¹⁴⁰ is independently a hydrogen atom, a substituted or unsubstituted alkyl group with 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 12 ring-forming carbon atoms;

Wherein 1 selected from R ¹³¹～R¹⁴⁰ is a single bond with 27, and 2 adjacent selected from R ¹³¹～R¹⁴⁰ which is not the single bond with 27 are not bonded to each other, and thus do not form a ring.

Examples of the unsubstituted alkyl group having 1 to 10 carbon atoms which may be represented by R ¹³¹～R¹⁴⁰ other than the single bond include the same groups as the unsubstituted alkyl group having 1 to 10 carbon atoms which may be substituted on the unsubstituted aryl group having 6 to 30 ring-forming carbon atoms which may be represented by Ar ¹ and Ar ²; the preferred embodiment is also the same.

Examples of the aryl group having 6 to 12 unsubstituted ring-forming carbon atoms which may be represented by R ¹³¹～R¹⁴⁰ other than the single bond include the same aryl groups having 6 to 12 unsubstituted ring-forming carbon atoms which may be substituted on the aryl group having 6 to 30 unsubstituted ring-forming carbon atoms which may be represented by Ar ¹ and Ar ²; the preferred embodiment is also the same.

[ Chemical formula 36]

In formula (1 e), 30 is a bonding position to one or both of L ¹ and L ²;

In the formula (1 e), R ¹⁵¹～R¹⁵⁵ is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group;

Wherein 1 selected from R ¹⁵¹～R¹⁵⁵ is a single bond with x 31 and the other 1 selected from R ¹⁵¹～R¹⁵⁵ is a single bond with x 32;

adjacent 2 selected from R ¹⁵¹～R¹⁵⁵ which is not the above single bond with x 31 nor the above single bond with x 32 are not bonded to each other and thus do not form a ring;

Examples of the unsubstituted alkyl group having 1 to 10 carbon atoms which may be represented by R ¹⁵¹～R¹⁵⁵ other than the single bond include the same groups as the unsubstituted alkyl group having 1 to 10 carbon atoms which may be substituted on the unsubstituted aryl group having 6 to 30 ring-forming carbon atoms which may be represented by Ar ¹ and Ar ²; the preferred embodiment is also the same.

In the formula (1 e), R ¹⁶¹～R¹⁶⁵ and R ¹⁷¹～R¹⁷⁵ are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms;

Wherein 1 or more groups selected from the group consisting of 2 or more adjacent groups of R ¹⁶¹～R¹⁶⁵ may be bonded to each other to form 1 or more unsubstituted benzene rings, or may not be bonded to each other to form a ring;

More than 1 group selected from the group consisting of 2 adjacent or more of R ¹⁷¹～R¹⁷⁵ may be bonded to each other to form 1 or more unsubstituted benzene rings, or may not be bonded to each other to form a ring.

Examples of the unsubstituted alkyl group having 1 to 10 carbon atoms which may be represented by the above-mentioned R ¹⁶¹～R¹⁶⁵ and R ¹⁷¹～R¹⁷⁵ include the same groups as the unsubstituted alkyl group having 1 to 10 carbon atoms which may be substituted on the unsubstituted aryl group having 6 to 30 ring-forming carbon atoms which may be represented by the above-mentioned Ar ¹ and Ar ²; the preferred embodiment is also the same.

The group represented by the above formula (1 e) includes groups represented by the following formulas (1 e-1) to (1 e-5).

[ Chemical formula 37]

In formula (1 e-1), formula (1 e-2), formula (1 e-3), formula (1 e-4) and formula (1 e-5), 30, R ¹⁵¹～R¹⁵⁵、R¹⁶¹～R¹⁶⁵ and R ¹⁷¹～R¹⁷⁵ are as defined above for formula (1 e), and preferred embodiments are the same.

In one embodiment of the above inventive compound, in formula (1),

In the case where Ar ¹ and Ar ² are each represented by the above formula (1 a), they may be the same or different from each other;

In the case where Ar ¹ and Ar ² are each represented by the above formula (1 b), they may be the same or different from each other;

in the case where Ar ¹ and Ar ² are each represented by the above formula (1 c), they may be the same or different from each other;

In the case where Ar ¹ and Ar ² are each represented by the above formula (1 d), they may be the same or different from each other;

In the case where Ar ¹ and Ar ² are each represented by the above formula (1 f), they may be the same or different from each other.

In one embodiment of the above inventive compound, in formula (1),

(1-1) R ¹～R⁶ may be each a hydrogen atom;

(1-2) R ¹¹～R¹⁴ may be each a hydrogen atom;

(1-3) R ²¹～R²⁸ which are not single bonds to a may each be a hydrogen atom;

(1-4) R ¹⁰¹～R¹⁰⁵, which are not single bonds to x 22, may each be a hydrogen atom;

(1-5) R ¹⁰⁶～R¹¹⁰, which are not single bonds to x 23, may each be a hydrogen atom;

(1-6) R ¹¹¹～R¹¹⁵ may be each a hydrogen atom;

(1-7) R ¹²¹～R¹²⁸, which are not single bonds to x 25, may each be a hydrogen atom;

(1-8) R ¹³¹～R¹⁴⁰ which are not single bonds to the 27 th bond may each be a hydrogen atom;

(1-9) R ¹⁵¹～R¹⁵, which is not a single bond to x 31 nor a single bond to x 32, may be each a hydrogen atom;

(1-10) R ¹⁶¹～R¹⁶⁵ may be each a hydrogen atom;

(1-11) R ¹⁷¹～R¹⁷⁵ may be each a hydrogen atom.

In one embodiment of the above-described inventive compound, in the formula (1), at least 1 of Ar ¹ and Ar ² is preferably a group represented by the above formula (1 a), and more preferably Ar ¹ and Ar ² are both groups represented by the above formula (1 a).

In one embodiment of the above-described inventive compound, in the formula (1), it is preferable that 1 of Ar ¹ or Ar ² is a group represented by the above-described formula (1 a), and the other 1 is a group represented by the above-described formula (1 b).

In one embodiment of the above-described compound of the invention, in the above-described formula (1 a), X is preferably CRbRc. That is, the group represented by the above formula (1 a) is preferably a group represented by the above formula (1 a-4).

The group represented by the above formula (1 a-4) is preferably represented by the following formula. In the following formulae, 1 representing a bonding position to one or both of L ¹ and L ², a single bond bonded to a, and R ²¹～R²⁸ are omitted for simplicity.

[ Chemical formula 38]

In one embodiment of the above-described inventive compound, in the above formula (1 a), more preferably, X is CRbRc and at least 1 of Rb and Rc is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

In one embodiment of the above inventive compound, in the above formula (1 a), R ²⁶ is preferably a single bond to a.

Wherein, as described above, in the formula (1), in the case where Ar ¹ and Ar ² are both represented by the above formula (1 a), they may be the same or different from each other.

In one embodiment of the above inventive compound, in the above formula (1 b), it is preferable that R ¹⁰¹ or R ¹⁰⁵ is a single bond to x 23 when m is 1 and n is 0, or R ¹⁰⁶ or R ¹¹⁰ is a single bond to x 23 when m is 0 and n is 1.

Wherein, as described above, in the formula (1), in the case where Ar ¹ and Ar ² are both represented by the above formula (1 b), they may be the same or different from each other.

In one embodiment of the above-described compound of the present invention, ar ³ is preferably cyclohexyl, adamantyl, phenyl or naphthyl substituted or unsubstituted with an alkyl group having 1 to 4 carbon atoms. The phenyl group substituted with an alkyl group having 1 to 4 carbon atoms is preferably a phenyl group substituted with 1 or 2 or more tertiary butyl groups; more preferably 3, 5-di-tert-butylphenyl.

In one embodiment of the above inventive compound, preferably one or both of L ¹ and L ² is a single bond.

In one embodiment of the above-described inventive compound, it is preferable that R ¹～R⁶ and R ¹¹～R¹⁴ are each a hydrogen atom.

In one embodiment of the above-described invention compound, 1 or more selected from the above-described preferred embodiments may be combined, and this embodiment is also a preferred embodiment of the above-described invention compound.

For example, in one embodiment of the above-described inventive compound, in the formula (1), 1 of Ar ¹ or Ar ² may be a group represented by the above formula (1 a), and the other 1 may be a group represented by the above formula (1 b); in the above formula (1 a), X is CRbRc, at least 1 of Rb and Rc is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms and R ²⁶ is a single bond to a; in the above formula (1 b), when m is 1 and n is 0, R ¹⁰¹ or R ¹⁰⁵ is a single bond to 23, or when m is 0 and n is 1, R ¹⁰⁶ or R ¹¹⁰ is a single bond to 23; ar ³ is cyclohexyl, adamantyl, phenyl or naphthyl substituted or unsubstituted by alkyl of 1 to 4 carbon atoms; one or both of L ¹ and L ² are single bonds; r ¹～R⁶ and R ¹¹～R¹⁴ are each a hydrogen atom.

As described above, the "hydrogen atom" used in the present specification includes protium atom, deuterium atom and tritium atom. Thus, the inventive compounds may contain deuterium atoms of natural origin.

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

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

A hydrogen atom represented by any one of R ¹～R⁶ of formula (1);

an alkyl group, a cycloalkyl group or an aryl group which any one of R ¹～R⁶ of the formula (1) may represent has a hydrogen atom;

a hydrogen atom represented by any one of R ¹¹～R¹⁴ of formula (1);

An alkyl group, a cycloalkyl group or an aryl group which any one of R ¹¹～R¹⁴ of the formula (1) may represent has a hydrogen atom;

aryl (also including alkyl groups which may be substituted thereon), cycloalkyl groups or hydrogen atoms which cycloalkyl groups have represented by Ar ³ of formula (1);

L ¹ of the formula (1) may represent a hydrogen atom of a phenylene group, a naphthylene group or a biphenylene group;

l ² of the formula (1) may represent a hydrogen atom of a phenylene group, a naphthylene group or a biphenylene group;

ar ¹ of the formula (1) may represent a hydrogen atom of an aryl group;

Ar ² of the formula (1) may represent a hydrogen atom of an aryl group;

A hydrogen atom represented by any one of R ²¹～R²⁸ of formula (1 a) which is not a single bond to a;

An alkyl group, a cycloalkyl group, or an aryl group of formula (1 a) which is not a single bond to a, and which may be represented by any one of R ²¹～R2⁸;

a hydrogen atom represented by Ra of formula (1 a);

an alkyl group, an aryl group or an aromatic heterocyclic group which may be represented by Ra of the formula (1 a) has a hydrogen atom;

rb, which is not a single bond to a, of formula (1 a), is a hydrogen atom represented by Rb;

an alkyl or aryl group of formula (1 a) that is not a single bond to a has a hydrogen atom that Rb can represent;

A hydrogen atom represented by Rc of formula (1 a) which is not a single bond to a;

An alkyl or aryl group of formula (1 a) which may be represented by Rc which is not a single bond to a has a hydrogen atom;

A hydrogen atom represented by any one of R ¹⁰¹～R¹⁰⁵ of formula (1 b) that is not a single bond to x 22;

an alkyl, cycloalkyl or aryl group of formula (1 b) having a hydrogen atom that is represented by any one of R ¹⁰¹～R¹⁰⁵ that is not a single bond to x 22;

A hydrogen atom represented by any one of R ¹⁰⁶～R¹¹⁰ of formula (1 b) which is not a single bond to x 23;

an alkyl, cycloalkyl or aryl group of formula (1 b) having a hydrogen atom that is represented by any one of R ¹⁰⁶～R¹¹⁰ that is not a single bond to x 23;

A hydrogen atom represented by any one of R ¹¹¹～R¹¹⁵ of formula (1 b);

A hydrogen atom of an alkyl group, a cycloalkyl group or an aryl group which any one of R ¹¹¹～R¹¹ of formula (1 b) may represent;

A hydrogen atom represented by any one of R ¹²¹～R¹²⁸ of formula (1 c) which is not a single bond to x 25;

an alkyl, cycloalkyl or aryl group of formula (1 c) having a hydrogen atom that is represented by any one of R ¹²¹～R¹²⁸ that is not a single bond to x 25;

a hydrogen atom represented by any one of R ¹³¹～R¹⁴⁰ of formula (1 d) which is not a single bond to x 27;

an alkyl, cycloalkyl or aryl group of formula (1 d) having a hydrogen atom that is represented by any one of R ¹³¹～R¹⁴⁰ that is not a single bond to x 27;

A hydrogen atom represented by any one of R ¹⁵1～R¹⁵⁵ of formula (1 e) which is not a single bond with x 31 nor a single bond with x 32;

A hydrogen atom of an alkyl, cycloalkyl or phenyl group represented by any one of R ¹⁵1～R¹⁵⁵ of formula (1 e) which is not a single bond with x 31 nor a single bond with x 32;

a hydrogen atom represented by any one of R ¹⁶¹～R¹⁶⁵ of formula (1 e);

An alkyl group or a cycloalkyl group which any one of R ¹⁶¹～R¹⁶⁵ of the formula (1 e) may represent has a hydrogen atom;

A hydrogen atom represented by any one of R ¹⁷¹～R¹⁷⁵ of formula (1 e);

an alkyl group or a cycloalkyl group represented by any one of R ¹⁷¹～R¹⁷⁵ of the formula (1 e) has a hydrogen atom.

The deuteration rate of the inventive compounds depends on the deuteration rate of the starting compounds 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 examples of the deuteration ratio of the compound of the present invention include ratios obtained by counting only the number of deuterium atoms represented by the chemical formula, and include ratios in which trace isotopes of natural origin are considered.

The deuteration ratio of the compound of the present invention 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 deuteration rate of the compound of the present invention is 100% or less. In other words, in one embodiment of the present invention, the deuteration ratio of the above-mentioned compound of the present invention is preferably 1 to 100%, more preferably 3 to 100%, further preferably 5 to 100%, still more preferably 10 to 100%, still more preferably 50 to 100%.

The inventive compound may be a mixture comprising a deuterated compound and a non-deuterated compound, a mixture of more than 2 compounds having different deuteration rates. The deuteration rate of such a mixture is preferably 1% or more, more preferably 3% or more, still more preferably 5% or more, still more preferably 10% or more, still more preferably 50% or more, and less than 100%. In other words, in one embodiment of the present invention, the deuteration ratio of the mixture is preferably 1% or more and less than 100%, more preferably 3% or more and less than 100%, still more preferably 5% or more and less than 100%, still more preferably 10% or more and less than 100%, still more preferably 50% or more and less than 100%.

The ratio of the number of deuterium atoms to the total number of hydrogen atoms in the compound of the present invention 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 other words, in one embodiment of the present invention, the ratio of the number of deuterium atoms in the above-mentioned inventive compound to the total number of hydrogen atoms is preferably 1 to 100%, more preferably 3 to 100%, still more preferably 5 to 100%, still more preferably 10 to 100%.

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 (optional substituent) are not particularly mentioned in the above description, and the substituent is the same as the description of the "substituent when expressed as" substituted or unsubstituted ", and is preferably an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 12 ring-forming carbon atoms. The details of each group are as described above. For example, the alkyl group having 1 to 6 carbon atoms is preferably methyl or tert-butyl. For example, the aryl group having 6 to 12 ring-forming carbon atoms is preferably a phenyl group.

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

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

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

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[ 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]

Material for organic EL element

The material for an organic EL element as an embodiment of the present invention contains the compound of the present invention. The content of the inventive compound in the material for an organic EL element is 1% by mass or more (including 100% by mass), preferably 10% by mass or more (including 100% by mass), more preferably 50% by mass or more (including 100% by mass), still more preferably 80% by mass or more (including 100% by mass), and particularly preferably 90% by mass or more (including 100% by mass). In other words, in one embodiment of the present invention, the content of the inventive compound in the material for an organic EL element is 1 to 100% by mass, preferably 10 to 100% by mass, more preferably 50 to 100% by mass, still more preferably 80 to 100% by mass, and particularly preferably 90 to 100% by mass.

The material for an organic EL element, which is one embodiment of the present invention, is useful for manufacturing an organic EL element.

In one embodiment of the present invention, the material for an organic EL element is preferably a hole transport layer material.

Organic EL element

An organic EL element as an embodiment of the present invention includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer comprises a light emitting layer, at least one layer of the organic layer comprising an inventive compound.

Examples of the organic layer containing the compound of the present invention 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. The compound of the present invention is preferably used as a material for a hole transporting region or a light emitting layer of a fluorescent or phosphorescent EL element, more preferably used as a material for a hole transporting region, further preferably used as a material for a hole injecting layer, a hole transporting layer, an electron blocking layer, or an exciton blocking layer, particularly preferably used as a material for a hole injecting layer or a hole transporting layer.

The organic EL element of the present invention may be a fluorescent or phosphorescent single-color light-emitting element, a fluorescent/phosphorescent mixed white light-emitting element, a simple type having a single light-emitting unit, or a Tandem type (Tandem) having a plurality of light-emitting units, and among these, a fluorescent light-emitting element is preferable. Here, the "light emitting unit" means: a minimum unit which includes an organic layer and at least one of which is a light emitting layer and in which injected holes and electrons are recombined to thereby emit light.

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 multi-layer type having a plurality of phosphorescent light emitting layers or 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 to 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)

(Jj) (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)

(N) (hole injection layer /) 1 st hole transport layer/2 nd hole transport layer/3 rd hole transport layer/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 /) a1 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. In addition, 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, respectively. 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 light emitting layer 5. The hole transport region disposed between the anode 3 and the light-emitting layer 5 is formed of a hole injection layer 6a, a1 st hole transport layer 6b, and a 2 nd hole transport layer 6 c. The electron transport region disposed between the light-emitting layer 5 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 light emitting layer 5. The hole transport region disposed between the anode 3 and the light-emitting layer 5 is formed of a hole injection layer 6a, a1 st hole transport layer 6b, a2 nd hole transport layer 6c, and a 3 rd hole transport layer 6 d. The electron transport region disposed between the light-emitting layer 5 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 only 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 board

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 polyimide, 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 a metal, an alloy, a conductive compound, a mixture thereof, or the like 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).

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 transport 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 comprises an inventive compound. The inventive compound is preferably contained in at least one of these layers constituting the hole transport layer, and the inventive compound is particularly preferably contained in the hole transport layer.

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 other than the inventive compound, 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 846]

(In the above formula, R ²²¹～R²²⁶ independently represents cyano, -CONH ₂, carboxyl, or-COOR ²²⁷(R²²⁷ represents alkyl group having 1 to 20 carbon atoms or cycloalkyl group having 3 to 20 carbon atoms). In addition, adjacent 2 selected from R ²²¹ and R ²²²、R²²³ and R ²²⁴, and R ²²⁵ and R ²²⁶ may be bonded to each other to form a group represented by-CO-O-CO-. )

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

Hole transport 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 inventive compound may be used for the hole transport layer alone or in combination with the following compound.

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 a1 st hole transport layer (anode side) and a2 nd hole transport layer (cathode side). That is, the hole transport region may include a1 st hole transport layer on the anode side and a2 nd hole transport layer on the cathode side. In addition, the hole transport layer may have a 3-layer structure including a1 st hole transport layer, a2 nd hole transport layer, and a3 rd hole transport layer in this order from the anode side. That is, the 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, and the hole transport layer closest to the cathode in the multi-layer structure, for example, the 2 nd hole transport layer of the 2-layer structure or the 3 rd hole transport layer of the 3-layer structure is preferably adjacent to the light emitting layer. In another embodiment of the present invention, an electron blocking layer or the like described below may be 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, in the case where the hole transport layer has a 2-layer structure, as described above, it is preferable that the 2 nd hole transport layer is adjacent to the light-emitting layer. That is, in the case where the organic layer includes a hole transport region located between the anode and the light-emitting layer, and the hole transport region has a 2-layer structure including a1 st hole transport layer on the anode side and a2 nd hole transport layer on the cathode side, it is preferable that the light-emitting layer and the 2 nd hole transport layer are in direct contact with each other.

In one embodiment of the present invention, in the case where the hole transport layer has a 2-layer structure, it is preferable that at least one of the 1 st hole transport layer and the 2 nd hole transport layer contains the compound of the present invention. That is, the inventive compound is preferably contained in only the 1 st hole transport layer, only the 2 nd hole transport layer, or both the 1 st hole transport layer and the 2 nd hole transport layer.

In one embodiment of the present invention, more preferably, the inventive compound is contained in the 2 nd hole transport layer. That is, it is more preferable that the inventive compound is contained only in the 2 nd hole transport layer, and that the inventive compound is contained in both the 1 st hole transport layer and the 2 nd hole transport layer.

In one embodiment of the present invention, in the case where the hole transport layer has a 3-layer structure, as described above, it is preferable that the 3 rd hole transport layer is adjacent to the light-emitting layer. That is, in the case where the organic layer includes a hole transport region located between the anode and the light-emitting layer, and the hole transport region has a 3-layer structure including, in order from the anode side, a1 st hole transport layer, a 2 nd hole transport layer, and a 3 rd hole transport layer, it is preferable that the light-emitting layer and the 3 rd hole transport layer are in direct contact with each other.

In one embodiment of the present invention, in the case where the hole transport layer has a 3-layer structure, it is preferable that at least one of the 1 st to 3 rd hole transport layers contains the compound of the present invention. That is, the inventive compound is preferably contained in only 1 st layer (only 1 st hole transport layer, only 2 nd hole transport layer, or only 3 rd hole transport layer) selected from the 1 st to 3 rd hole transport layers, only 2 nd layer (only 1 st and 2 nd hole transport layers, only 1 st and 3 rd hole transport layers, or only 2 nd and 3 rd hole transport layers), or all of the 1 st to 3 rd hole transport layers.

In one embodiment of the present invention, it is more preferable that the inventive compound is contained in the 3 rd hole transport layer. That is, it is more preferable that the inventive compound is contained only in the 3 rd hole transport layer, or that the inventive compound is contained in either one or both of the 3 rd hole transport layer and the 1 st hole transport layer and the 2 nd hole transport layer.

In one embodiment of the present invention, the inventive compound contained in each of the hole transport layers is preferably a protium from the standpoint of manufacturing cost. The protium is an inventive compound in which all hydrogen atoms in the inventive compound are protium atoms.

Accordingly, in one aspect of the present invention, it is preferable to include: one or both of the 1 st hole transport layer and the 2 nd hole transport layer (in the case of a 2-layer structure) includes an organic EL element of an inventive compound formed substantially only from protium, and at least one of the 1 st to 3 rd hole transport layers includes an organic EL element of an inventive compound formed substantially only from protium. The meaning of "an inventive compound formed substantially only from 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 mol%) based on the total amount of the inventive compound. In other words, in one embodiment of the present invention, the expression "an inventive compound substantially formed only of protium" means that the content of protium is 90 to 100 mol%, preferably 95 to 100 mol%, more preferably 99 to 100 mol% based on the total amount of the inventive compound.

Examples of the hole transporting layer material other than the inventive compound 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 (abbreviation: 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 (abbreviated as DFLDPBi), 4',4 "-tris (N, N-diphenylamino) triphenylamine (abbreviated as TDATA), 4',4" -tris [ N- (3-methylphenyl) -N-phenylamino ] triphenylamine (abbreviated as MTDATA), and 4,4' -bis [ N- (spiro-9, 9' -bifluor-2-yl) -N-phenylamino ] biphenyl (abbreviated as BSPB). The compound has hole mobility of more than 10 ^-6cm²/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 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 the organic EL element having the hole transport layer of the 2-layer structure of the present invention, it is preferable that the 1 st hole transport layer contains 1 or two or more compounds represented by the following formula (11) or formula (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 847]

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

L ^A1、L^B1、L^C1、L^A2、L^B2、L^C2 and L ^D2 are each independently 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 identical to 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 ^E2 which does not form the above single ring and does not form the above condensed ring 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、B¹、C¹、A²、B²、C² and D ² are each independently 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 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms,

Where there are plural R '₉₀₁, plural R' ₉₀₁ are the same or different from each other,

Where there are plural R '₉₀₂, plural R' ₉₀₂ are the same or different from each other,

Where there are plural R '₉₀₃, plural R' ₉₀₃ are the same or different from each other. ]

In the formula (11) and the formula (12), it is preferable that A1, B1, C1, A2, B2, C2, and D2 are 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, at least one of A1, B1, and C1 in formula (11), and at least one of A2, B2, C2, and D2 in formula (12) 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 selected from A ¹、B¹、C¹、A²、B²、C² and D ² may have a substituent at the 9-position, and may be, for example, 9-dimethylfluorenyl or 9, 9-diphenylfluorenyl. In addition, a ring may be formed by substituents at the 9-position with each other, and for example, a fluorene skeleton or a xanthene skeleton may be formed by substituents at the 9-position with each other.

L ^A1、L^B1、L^C1、L^A2、L^B2、L^C2 and L ^D2 are preferably each independently 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 848]

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.

In one embodiment of the organic EL element according to the present invention, the light-emitting layer is preferably a single layer.

In another embodiment of the organic EL element according to the present invention, the light-emitting layer preferably includes a1 st light-emitting layer and a2 nd light-emitting layer.

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 ] -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 can be mentioned.

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 YGABPhA), N, 9-triphenylanthracene-9-amine (abbreviated as: 34) and the like can be cited.

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) naphthacene-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-mPhAFD) and the like are exemplified.

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

As a blue-based phosphorescent 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 (acetylacetonato) (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 are luminescent (electron transitions between different multiple degrees) from rare earth metal ions.

Host material for 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.

As the host material, for example, there is used

(1) Aluminum Lv Laoge complex, beryllium complex, zinc complex, or other metal complex,

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

N, N-diphenyl-9- [4- (10-phenyl-9-anthryl) phenyl ] -9H-carbazol-3-amine (abbreviation: czA PA), 4- (10-phenyl-9-anthryl) triphenylamine (abbreviation: DPhPA), N, 9-diphenyl-N- [4- (10-phenyl-9-anthryl) phenyl ] -9H-carbazol-3-amine (abbreviation: PCAPA), N, 9-diphenyl-N- {4- [4- (10-phenyl-9-anthryl) phenyl ] phenyl) -9H-carbazol-3-amine (abbreviation: PCAPBA), N- (9, 10-diphenyl-2-anthryl) -N, 9-diphenyl-9H-carbazol-3-amine (abbreviation: 2 PCAPA), 4' -bis [ N- (1-naphthyl) -N-phenylamino ] biphenyl (abbreviation: NPB or α -NPD), N '-bis (3-methylphenyl) -N, N' -diphenyl- [1,1 '-biphenyl ] -4,4' -diamine (abbreviation: TPD), 4' -bis [ N- (9, 9-dimethylfluoren-2-yl) -N-phenylamino ] biphenyl (abbreviation: DFLDPBi), 4 '-bis [ N- (spiro-9, 9' -bifluorene-2-yl) -N-phenylamino ] biphenyl (abbreviation: BSPB), and the like. 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 849]

[ Chemical formula 850]

[ Chemical formula 851]

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, 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.

In the organic EL element of the present invention, the light-emitting layer may contain a luminescent compound (hereinafter, may be simply referred to as "luminescent compound") that emits fluorescence having a main peak wavelength of 500nm or less. The lower limit value of the main peak wavelength is not particularly limited as long as the effect of the present invention is exhibited, and in one embodiment of the organic EL element, for example, the lower limit value of the main peak wavelength may be 400nm. Accordingly, in one embodiment of the organic EL element, the main peak wavelength may be, for example, 400 to 500nm.

The main peak to peak wavelength of the compound was measured as follows. A5. Mu. Mol/L toluene solution of the compound to be measured was prepared and placed in a quartz cuvette, and the luminescence spectrum of the sample was measured at room temperature (300K) (the vertical axis represents the luminescence intensity, and the horizontal axis represents the wavelength). The luminescence spectrum can be measured by a spectrophotometer (apparatus name: F-7000) manufactured by Hitachi, inc. of Hitachi, new technology. The light emission spectrum measuring device is not limited to the device used herein.

In the emission spectrum, the peak wavelength of the emission spectrum at which the emission intensity reaches the maximum is set as the main peak-to-peak wavelength. In the present specification, the main peak-to-peak wavelength may be referred to as a fluorescence emission main peak-to-peak wavelength (FL-peak).

The fluorescent compound may be the dopant material or the host material.

In the case where the light-emitting layer is a single layer, only one of the dopant material and the host material may be the fluorescent compound, or both may be the fluorescent compound.

In the case where the light-emitting layer includes the 1 st light-emitting layer (anode side) and the 2 nd light-emitting layer (cathode side), only one of the 1 st light-emitting layer and the 2 nd light-emitting layer may include the fluorescent compound, or both of the light-emitting layers may include the fluorescent compound. When the 1 st light-emitting layer contains the above-mentioned fluorescent compound, only one of the dopant material and the host material contained in the 1 st light-emitting layer may be the above-mentioned fluorescent compound, or both may be the above-mentioned fluorescent compound. In the case where the 2 nd light-emitting layer contains the above-mentioned fluorescent compound, only one of the dopant material and the host material contained in the 2 nd light-emitting layer may be the above-mentioned fluorescent compound, or both may be the above-mentioned fluorescent compound.

Electron transport layer

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

The electron transport layer may have a single-layer structure or a multilayer structure including 2 or more layers. For example, the electron transport layer may be a 2-layer structure including a 1st electron transport layer (anode side) and a 2nd electron transport layer (cathode side). In one embodiment of the present invention, the electron transport layer of the single-layer structure is preferably adjacent to the light emitting layer, or the electron transport layer closest to the anode in the multi-layer structure, for example, the 1st electron transport layer of the 2-layer structure is preferably adjacent to the light emitting layer. In another embodiment of the present invention, a hole blocking layer or the like described below may be interposed between the electron transport layer and the light emitting layer having the single-layer structure or between the electron transport layer and the light emitting layer closest to the light emitting layer in the multilayer structure.

The electron transport layer may be used, for example

(1) Metal complexes such as aluminum Lv Laoge 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 (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), bis [2- (2-benzothiazolyl) phenol ] zinc (II) (abbreviated as ZnBTZ), and lithium (8-hydroxyquinoline) (abbreviated as Liq).

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 material has an electron mobility of 10 ^-6cm²/Vs or more. 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.

Electron injection layer

The electron injection layer is a layer containing a material having high electron injection properties. Examples of the electron injection layer include alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca) and strontium (Sr), rare earth metals such as europium (Eu) and ytterbium (Yb), and compounds containing these metals. Examples of such a compound include: alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes, alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, rare earth metal oxides, rare earth metal halides, and rare earth metal-containing organic complexes. In addition, a plurality of these compounds may be used in combination.

In addition, a material containing an alkali metal, an alkaline earth metal, or a compound thereof in a material having electron-transporting property, specifically, a material containing magnesium (Mg) in Alq, or the like can be used. 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 electrode

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 Al, ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, or other various conductive materials, 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 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, thereby blocking the excitons within the light emitting layer.

The layers of the organic EL element can be formed by a conventionally known vapor deposition method, a coating method, or the like. For example, the film can be formed by a vapor deposition method such as a vacuum vapor deposition method or a molecular beam vapor deposition method (MBE method), or a known method using a solution of a compound forming a layer, such as a coating method such as a dip coating method, a spin coating method, a casting method, a bar coating method, or a roll coating method.

The film thickness of each layer is not particularly limited, and in general, if the film thickness is too small, defects such as pinholes tend to occur, whereas if it is too large, high driving voltage is required and efficiency is deteriorated, so that it is usually 5nm to 10 μm, more preferably 10nm to 0.2 μm.

In the organic EL element having the hole transport layer having the 2-layer structure or the 3-layer structure of the present invention, the total thickness of the 1 st hole transport layer and the thickness of the 2 nd hole transport layer is preferably 30nm or more and 150nm or less, more preferably 40nm or more and 130nm or less.

In one embodiment of the present invention, the thickness of the 2 nd hole transport layer having a 2-layer structure or a 3-layer structure is preferably 5nm or more, more preferably 20nm or more, still more preferably 25nm or more, particularly preferably 35nm or more, and further preferably 100nm or less. In other words, in one embodiment of the present invention, the thickness of the 2 nd hole transport layer having a 2-layer structure or a 3-layer structure is, for example, preferably 5 to 100nm, more preferably 20 to 100nm, still more preferably 25 to 100nm, and particularly preferably 35 to 100nm.

In one embodiment of the present invention, the thickness of the hole transport layer adjacent to the light-emitting layer is preferably 5nm or more, more preferably 20nm or more, still more preferably 25nm or more, particularly preferably 30nm or more, and further preferably 100nm or less. In other words, in one embodiment of the present invention, the thickness of the 2 nd hole transport layer having a 2-layer structure or a 3-layer structure is, for example, preferably 5 to 100nm, more preferably 20 to 100nm, still more preferably 25 to 100nm, and particularly preferably 30 to 100nm.

In the organic EL element having the hole transport layer having the 2-layer structure or the 3-layer structure of the present invention, the ratio of the film thickness D2 of the 2 nd hole transport layer to the film thickness D1 of the 1 st hole transport layer is preferably 0.3 < D2/D1<4.0, more preferably 0.5< D2/D1<3.5, still more preferably 0.75< D2/D1<3.0.

A preferred embodiment of the organic EL element of the present invention includes, for example:

(1) Organic EL element having hole transport layer of 2-layer structure

Embodiment 1 wherein the 2 nd hole transport layer contains an inventive compound and the 1 st hole transport layer does not contain an inventive compound;

embodiment 2 wherein the 1 st hole transport layer and the 2 nd hole transport layer each contain the inventive compound;

Embodiment 3 wherein the 1 st hole transport layer contains an inventive compound and the 2 nd hole transport layer does not contain an inventive compound;

(2) Organic EL element having hole transport layer of 3-layer structure

Embodiment 4 wherein the 1 st hole transport layer contains an inventive compound, the 2 nd hole transport layer, and the 3 rd hole transport layer do not contain an inventive compound;

embodiment 5 wherein the 2 nd hole transport layer contains an inventive compound, the 1 st hole transport layer, and the 3 rd hole transport layer do not contain an inventive compound;

embodiment 6 wherein the 3 rd hole transport layer contains an inventive compound, the 1 st hole transport layer, and the 2 nd hole transport layer do not contain an inventive compound;

Embodiment 7 wherein the 1 st hole transport layer and the 2 nd hole transport layer contain an inventive compound and the 3 rd hole transport layer does not contain an inventive compound;

embodiment 8 wherein the 1 st hole transport layer and the 3 rd hole transport layer contain an inventive compound and the 2 nd hole transport layer does not contain an inventive compound;

Embodiment 10 wherein the 2 nd hole transport layer and the 3 rd hole transport layer contain an inventive compound and the 1 st hole transport layer does not contain an inventive compound;

Embodiment 10 wherein the 1 st to 3 rd hole transport layers each contain the compound of the present invention; etc.

Electronic equipment

The organic EL element can be used for, for example, display members such as an organic EL panel module, display devices such as televisions, mobile phones, personal computers, and electronic devices such as lighting devices and light emitting devices for vehicle lamps. That is, an electronic device according to an embodiment of the present invention includes the organic EL element described above.

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.

Inventive Compounds used in the manufacture of organic EL elements of examples 1 to 5

[ Chemical formula 852]

[ Chemical formula 853]

Comparative compound used for producing organic EL element of comparative example 1

[ Chemical formula 854]

Other compounds used in the production of the organic EL elements of examples and comparative examples

[ Chemical formula 855]

Fabrication of organic EL element

Example 1

A glass substrate (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 subjected to UV ozone cleaning for 30 minutes. The film thickness of ITO was 130nm.

The cleaned glass substrate with the ITO transparent electrode is arranged on a substrate frame of a vacuum evaporation device.

First, a hole injection layer having a film thickness of 10nm was formed by co-evaporating a compound HT-1 and a compound HI-1 on a surface on which a transparent electrode was formed so as to cover the transparent electrode. The mass ratio of compound HT-1 to compound HI-1 (HT-1: HI-1) was 97:3.

Then, a1 st hole transport layer having a film thickness of 40nm was formed by vapor deposition of the compound HT-1 on the hole injection layer.

Next, the inventive compound Inv-1 was vapor deposited on the 1 st hole transport layer to form a2 nd hole transport layer having a film thickness of 40 nm.

Then, a 3 rd hole transport layer having a film thickness of 5nm was formed by vapor deposition of a compound HT-2 on the 2 nd hole transport layer.

Next, a light-emitting layer having a film thickness of 20nm was formed by co-vapor deposition of a compound BH-1 (host material) and a compound BD-1 (dopant material) on the 3 rd hole transport layer. The mass ratio of the compound BH-1 to the compound BD-1 (BH-1: BD-1) was 99:1.

Then, a1 st electron transport layer having a film thickness of 5nm was formed by vapor deposition of the compound ET-1 on the light-emitting layer.

Then, the 2 nd electron transport layer having a film thickness of 25nm was formed by co-depositing the compounds ET-2 and Liq on the 1 st electron transport layer. The mass ratio of the compound ET-2 to Liq (ET-2: liq) is 50:50.

Next, yb 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 50 nm.

The layer constitution of the organic EL element thus obtained is shown below.

ITO(130)/HT-1：HI-1＝97：3(10)/HT-1(40)/Inv-1(40)/HT-2(5)/BH-1：

BD-1＝99：1(20)/ET-1(5)/ET-2：Liq＝50：50(25)/Yb(1)/A1(50)

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

Examples 2 to 5

An organic EL device was fabricated in the same manner as in example 1, except that the inventive compounds shown in table 1 below were used as the hole transport layer material 2 instead of the inventive compound Inv-1.

Comparative example 1

An organic EL element was produced in the same manner as in example 1, except that the comparative compound Ref-1 was used instead of the inventive compound Inv-1.

Evaluation of organic EL element

(1) Measurement of drive Voltage

The voltage (V) was measured by applying a voltage to the organic EL element so that the current density was 10mA/cm ². The results are shown in Table 1.

(2) Determination of External Quantum Efficiency (EQE)

The obtained organic EL element was subjected to DC constant current driving at a current density of 10mA/cm ² at room temperature. 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 Table 1.

TABLE 1

As is clear from the results of Table 1, each of the inventive compound Inv-1, the inventive compound Inv-2, the inventive compound Inv-4, the inventive compound Inv-7 and the inventive compound Inv-8 was capable of providing an organic EL element with high external quantum efficiency driven at a low voltage, as compared to the comparative compound Ref-1.

Inventive compounds synthesized in synthesis examples

[ Chemical formula 856]

[ Chemical formula 857]

Intermediate synthesis example 1: synthesis of intermediate A

[ Chemical formula 858]

A mixture of 1, 8-dibromonaphthalene (22.18 g, 78.00 mmol), phenylboronic acid (9.93 g, 81.00 mmol), tetrakis (triphenylphosphine) palladium (0) (4.48 g, 3.88 mmol), potassium carbonate (12.86 g, 93.00 mmol), toluene (78 mL) and water (19 mL) was stirred at 90℃for 3 hours under argon. The reaction mixture was cooled to room temperature, extracted with toluene, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain intermediate A as a yellow oil (17.8 g). The yield was 81%.

Intermediate synthesis example 2: synthesis of intermediate B

[ Chemical formula 859]

A mixture of intermediate A (4.25 g, 15.00 mmol), 2-chlorobenzeneboronic acid (2.81 g, 18.00 mmol), bis [ di-tert-butyl (4-dimethylaminophenyl) phosphine ] dichloropalladium (II) (0.319 g, 0.450 mmol), sodium carbonate (4.77 g, 45.00mm I1), DME (75 mL) and water (23 mL) was stirred at 80℃for 2 hours under argon. The reaction solution was cooled to room temperature, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain intermediate B as a white solid (3.60 g). The yield was 76%.

Intermediate synthesis example 3: synthesis of intermediate C

[ Chemical formula 860]

The same operation as in intermediate synthesis example 2 was performed using (3, 5-di-t-butylphenyl) boronic acid (boric acid) instead of phenylboronic acid used in intermediate synthesis example 1 to obtain intermediate C as a white solid, instead of intermediate a.

Intermediate synthesis example 4: synthesis of intermediate D

[ Chemical formula 861]

The same operation as in intermediate synthesis example 2 was performed except that the intermediate obtained by using cyclohexylboric acid instead of phenylboric acid in intermediate synthesis example 1 was used instead of intermediate a, to obtain intermediate D as a white solid.

Intermediate synthesis example 5: synthesis of intermediate E

[ Chemical formula 862]

A mixture of 9, 9-diphenyl-9H-fluoren-2-amine (5.00 g, 15.00 mmol), intermediate B (4.72 g, 15.00 mmol), tris (dibenzylideneacetone) dipalladium (0) (0.274 g, 0.300 mmol), tri-tert-butylscaly tetrafluoroborate (0.348 g, 2.25 mmol), sodium tert-butoxide (2.16 g, 9.36 mmol), toluene (75 mL) was stirred at 100deg.C for 3 hours under argon. The reaction solution was cooled to room temperature, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain intermediate E as a white solid (5.69 g). The yield was 93%.

Intermediate synthesis example 6: synthesis of intermediate F

[ Chemical formula 863]

The same procedures as in intermediate synthesis example 5 were repeated except for using 2-bromo-1, 1' -biphenylene instead of intermediate B in intermediate synthesis example 5, to obtain intermediate F as a white solid.

Intermediate synthesis example 7: synthesis of intermediate G

[ Chemical formula 864]

The same operations as in intermediate synthesis example 5 were performed in place of 9, 9-diphenyl-9H-fluoren-2-amine in intermediate synthesis example 5, except that 9, 9-dimethyl-9H-fluoren-2-amine was used and 2-bromo-9, 9-dimethyl-9H-fluorene was used in place of intermediate B, to obtain intermediate G as a white solid.

Intermediate synthesis example 8: synthesis of intermediate H

[ Chemical formula 865]

The same operations as in intermediate synthesis example 5 were performed in the same manner as in intermediate synthesis example 6 except that 9-methyl-9-phenyl-9H-fluoren-2-amine was used instead of 9, 9-diphenyl-9H-fluoren-2-amine, to obtain intermediate H as a white solid.

Synthesis example 1: synthesis of inventive Compound Inv-1

[ Chemical formula 866]

A mixture of intermediate E (6.12 g, 10.00 mmol), bromobenzene (1.57 g, 10.00 mmol), tris (dibenzylideneacetone) dipalladium (0) (0.183 g, 0.200 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.232 g, 0.800 mmol), sodium tert-butoxide (1.44 g, 15.00 mmol), xylene (50 mL) was stirred at 130℃for 3 hours under argon. After cooling the reaction solution to room temperature, concentration was performed under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 3.65g of a white solid. The yield was 53%.

The result of mass spectrometry of the obtained white solid was that of the compound Inv-1 of the invention, m/e=688 with respect to molecular weight 687.89.

Synthesis example 2: synthesis of inventive Compound Inv-2

[ Chemical formula 867]

The same operations as in Synthesis example 1 were performed except that 2-bromo-1, 1' -biphenyl was used instead of bromobenzene used in Synthesis example 1, to obtain a white solid.

The result of mass spectrometry of the obtained white solid was that of the compound Inv-2 of the invention, m/e=764 with respect to molecular weight 763.98.

Synthesis example 3: synthesis of inventive Compound Inv-3

[ Chemical formula 868]

The same operations as in Synthesis example 1 were conducted except that 1-bromobenzene-2, 3,4,5,6-d5 was used instead of bromobenzene used in Synthesis example 1, to obtain a white solid.

The result of mass spectrometry of the obtained white solid was that of the inventive compound Inv-3, m/e=693 with respect to molecular weight 692.92.

Synthesis example 4: synthesis of inventive Compound Inv-4

[ Chemical formula 869]

The same operations as in Synthesis example 1 were conducted except that 1-bromo-3, 5-di-t-butylbenzene was used instead of bromobenzene used in Synthesis example 1, to obtain a white solid.

The result of mass spectrometry of the obtained white solid was that of the inventive compound Inv-4, m/e=800 with respect to molecular weight 800.10.

Synthesis example 5: synthesis of inventive Compound Inv-5

[ Chemical formula 870]

The same procedure as in Synthesis example 1 was repeated except that in Synthesis example 1, intermediate F and intermediate C were used instead of intermediate E and bromobenzene, to obtain a white solid.

The result of mass spectrometry of the obtained white solid was that of the inventive compound Inv-5, m/e=876 with respect to molecular weight 876.20.

Synthesis example 6: synthesis of inventive Compound Inv-6

[ Chemical formula 871]

The same operation as in Synthesis example 1 was performed except that in Synthesis example 1, intermediate F and intermediate D were used instead of intermediate E and bromobenzene, and a white solid was obtained.

The result of mass spectrometry of the obtained white solid was that of the inventive compound Inv-6, m/e=770 with respect to the molecular weight of 770.03.

Synthesis example 7: synthesis of inventive Compound Inv-7

[ Chemical formula 872]

The same operation as in Synthesis example 1 was performed except that in Synthesis example 1, intermediate G and intermediate B were used instead of intermediate E and bromobenzene, and a white solid was obtained.

The result of mass spectrometry of the obtained white solid was that of the inventive compound Inv-7, m/e=680 with respect to molecular weight 679.91.

Synthesis example 8: synthesis of inventive Compound Inv-8

[ Chemical formula 873]

The same operation as in Synthesis example 1 was performed except that in Synthesis example 1, intermediate H and intermediate B were used instead of intermediate E and bromobenzene, and a white solid was obtained.

The result of mass spectrometry of the obtained white solid was that of the inventive compound Inv-8, m/e=702 with respect to molecular weight 701.91.

Symbol description

1. 11, 12 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

6D 3 rd hole transport layer

7. Electron transport region (electron transport layer)

7A 1 st electron transport layer

7B 2 nd electron transport layer

10. 20, 30 Light emitting unit

Claims

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

In formula (1),

N* is the central nitrogen atom,

R ¹ to R ⁶ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or an unsubstituted aryl group having 6 to 18 ring carbon atoms, wherein one or more groups of two or more adjacent groups selected from R ¹ to R ⁶ may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form no ring,

Ar ³ is an aryl group having 6 to 18 ring carbon atoms and substituted or unsubstituted by an alkyl group, an unsubstituted alkyl group having 1 to 10 ring carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms,

R ¹¹ to R ¹⁴ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or an unsubstituted aryl group having 6 to 18 ring carbon atoms, wherein one or more groups consisting of two or more adjacent groups selected from R ¹¹ to R ¹⁴ may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form no ring,

^L1 and ^L2 are each independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group, wherein the substituent of the substituted phenylene group, the substituted naphthylene group, or the substituted biphenylene group is an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms, and the phenylene group, the biphenylene group, and the naphthylene group do not have a condensed ring.

^Ar1 and ^Ar2 are each independently a group represented by the following formula (1a), or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, wherein the aryl group having 6 to 30 ring carbon atoms only contains a six-membered ring, and the substituent in the substituted aryl group having 6 to 30 ring carbon atoms is at least one selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms and a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms,

In the case where two or more of the ring-forming carbon atoms of the aryl group having 6 to 30 ring carbon atoms are substituted with alkyl groups, the two or more alkyl groups are not bonded to each other to form a ring,

In formula (1a),

*1 is the bonding position to one or both of ^L1 and ^L2 ;

X is an oxygen atom, a sulfur atom, NRa, or CRbRc;

Ra 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 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 13 ring atoms;

Rb and Rc are each independently 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 carbon atoms;

Among them, Rb and Rc are optionally bonded to each other to form a ring structure with 8 or more ring atoms, or are not bonded to each other to form no ring structure;

R ²¹ to R ²⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms;

wherein one selected from R ²¹ to R ²⁸ , Rb and Rc is a single bond bonded to *a, and Ra is not bonded to *a;

Two adjacent ones selected from R ²¹ to R ²⁸ that are not the single bond bonding to *a are not bonded to each other and thus do not form a ring.

2. The compound according to claim 1, wherein

Ar ¹ and Ar ² are each independently a group represented by the following formula (1a), a group represented by the following formula (1b), a group represented by the following formula (1c), a group represented by the following formula (1d), or a group represented by the following formula (1e),

In formula (1a),

*1, *a, X and R ²¹ to R ²⁸ are the same as those defined in the formula (1a).

In formula (1b),

*21 is the bonding position to one or both of ^L1 and ^L2 ;

One selected from R ¹⁰¹ to R ¹⁰⁵ is a single bond bonded to *22, and one selected from R ¹⁰⁶ to R ¹¹⁰ is a single bond bonded to *23;

R ¹⁰¹ to R ¹⁰⁵ and R ¹⁰⁶ to R ¹¹⁰ which are not single bonds are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms;

Adjacent two selected from R ¹⁰¹ to R ¹⁰⁵ that are not the single bond are not bonded to each other and thus do not form a ring;

Adjacent two selected from R ¹⁰⁶ to R ¹¹⁰ that are not the single bond are not bonded to each other and thus do not form a ring;

R ¹¹ 1 to R ¹¹ 5 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms;

wherein two adjacent ones selected from R ¹¹ 1 to R ¹¹ 5 are not bonded to each other and thus do not form a ring;

m is 0 or 1, n is 0 or 1;

in,

When m and n are 0, *23 represents the bonding position to one or both of ^L1 and ^L2 ,

When m is 0 and n is 1, *22 represents the bonding position to one or both of ^L1 and ^L2 ,

When m is 1 and n is 0, one selected from R ¹⁰¹ to R ¹⁰⁵ is a single bond bonded to *23,

In formula (1c),

*24 is the bonding position to one or both of ^L1 and ^L2 ;

R ¹²¹ to R ¹²⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms;

wherein one selected from R ¹²¹ to R ¹²⁸ is a single bond bonded to *25, and two adjacent selected from R ¹²¹ to R ¹²⁸ that are not the single bond bonded to *25 are not bonded to each other and thus do not form a ring,

In formula (1d),

*26 is the bonding position to one or both of ^L1 and ^L2 ;

R ¹³¹ to R ¹⁴⁰ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms;

wherein one selected from R ¹³¹ to R ¹⁴⁰ is a single bond bonded to *27, and two adjacent selected from R ¹³¹ to R ¹⁴⁰ that are not the single bond bonded to *27 are not bonded to each other to form a ring,

In formula (1e),

*30 is the bonding position to one or both of ^L1 and ^L2 ;

R ¹⁵¹ to R ¹⁵⁵ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group;

wherein one selected from R ¹⁵¹ to R ¹⁵⁵ is a single bond bonded to *31, and another one selected from R ¹⁵¹ to R ¹⁵⁵ is a single bond bonded to *32;

Two adjacent ones selected from R ¹⁵¹ to R ¹⁵⁵ that are neither the single bond bonding to *31 nor the single bond bonding to *32 are not bonded to each other and thus do not form a ring;

R ¹⁶¹ to R ¹⁶⁵ and R ¹⁷¹ to R ¹⁷⁵ are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms;

wherein one or more groups of two or more adjacent groups selected from R ¹⁶¹ to R ¹⁶⁵ may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form no ring;

One or more groups of the group consisting of two or more adjacent groups selected from R ¹⁷¹ to R ¹⁷⁵ may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form no ring.

3. The compound according to claim 2, wherein

One of Ar ¹ and Ar ² is a group represented by the above formula (1a), and the other is a group represented by the above formula (1b).

4. The compound according to claim 2 or 3, wherein

In the formula (1b), when m is 1 and n is 0, R ¹⁰¹ or R ¹⁰⁵ is a single bond bonding to *23, or when m is 0 and n is 1, R ¹⁰⁶ or R ¹¹⁰ is a single bond bonding to *23.

5. The compound according to any one of claims 1 to 4, wherein

At least one of Ar ¹ and Ar ² is a group represented by the above formula (1a).

6. The compound according to any one of claims 1 to 5, wherein

In the above formula (1a), X is CRbRc, and at least one of Rb and Rc is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

7. The compound according to any one of claims 1 to 6, wherein

In the above formula (1a), R2 ^to R6 are single bonds bonded to *a.

8. The compound according to any one of claims 1 to 7, wherein

Ar ³ is cyclohexyl, adamantyl, phenyl which may be substituted or unsubstituted by an alkyl group having 1 to 4 carbon atoms, or naphthyl.

9. The compound according to any one of claims 1 to 8, wherein

One or both of ^L1 and ^L2 are a single bond.

10. The compound according to any one of claims 1 to 9, wherein

R ¹ to R ⁶ and R ¹¹ to R ¹⁴ are all hydrogen atoms.

11 . The compound according to any one of claims 1 to 10 , comprising at least one deuterium atom.

12 . A material for an organic electroluminescent device, comprising the compound according to claim 1 .

13 . A hole transport layer material comprising the compound according to claim 1 .

14 . An organic electroluminescent device comprising an anode, a cathode, and an organic layer located between the anode and the cathode, wherein the organic layer comprises a light-emitting layer, and at least one layer of the organic layer comprises the compound according to claim 1 .

15. The organic electroluminescent element according to claim 14, wherein

The organic layer includes a hole transport region between the anode and the light emitting layer, and the hole transport region includes the compound.

16. The organic electroluminescent element according to claim 15, wherein

The hole transport region includes a first hole transport layer on the anode side and a second hole transport layer on the cathode side, and one or both of the first hole transport layer and the second hole transport layer include the compound.

17. The organic electroluminescent element according to claim 16, wherein:

The light-emitting layer is directly in contact with the second hole transport layer.

18. The organic electroluminescent element according to claim 16 or 17, wherein:

The total thickness of the first hole transport layer and the second hole transport layer is greater than or equal to 30 nm and less than or equal to 150 nm.

19. The organic electroluminescent element according to claim 15, wherein

The hole transport region includes a first hole transport layer, a second hole transport layer, and a third hole transport layer in order from the anode side.

Only one layer selected from the first to third hole transport layers contains the compound, only two layers selected from the first to third hole transport layers contain the compound, or all of the first to third hole transport layers contain the compound.

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

The light-emitting layer is directly in contact with the third hole transport layer.

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

22. The organic electroluminescent element according to any one of claims 14 to 21, wherein

The light-emitting layer is a single layer.

23. The organic electroluminescent element according to any one of claims 14 to 22, wherein

The light-emitting layer contains a light-emitting compound that emits fluorescence with a main peak wavelength of 500 nm or less.

24. The organic electroluminescent element according to any one of claims 14 to 23, wherein

The light-emitting layer includes a fluorescent dopant material.

25 . An electronic device comprising the organic electroluminescent element according to claim 14 .