KR20250007515A - Compounds, materials for organic electroluminescent devices, organic electroluminescent devices, and electronic devices - Google Patents

Abstract

(식(1) 또는 (2) 중의 각 기호는 명세서에 있어서 정의한 대로이다.), 상기 식(1) 또는 (2)로 표시되는 화합물을 포함하는 유기 전기발광 소자, 및 해당 유기 전기발광 소자를 포함하는 전자 기기에 관한 것이다.A compound represented by the following formula (1) or (2):

(Each symbol in formula (1) or (2) is as defined in the specification.), relates to an organic electroluminescent device comprising a compound represented by formula (1) or (2), and an electronic device comprising the organic electroluminescent device.

Description

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

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

In general, an organic electroluminescence device (hereinafter, sometimes referred to as an "organic EL device") is composed of an anode, a cathode, and an organic layer sandwiched between the anode and the cathode. When a voltage is applied between the two electrodes, electrons are injected from the cathode side and 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, the development of a material that efficiently transports electrons or holes to the light-emitting region and facilitates the recombination of electrons and holes is important for obtaining a high-performance organic EL device.

Patent documents 1 to 13 disclose compounds used as materials for organic electroluminescence devices.

International Publication No. 2016/006708 International Publication No. 2015/174640 Specification of United States Patent Application Publication No. 2016/0359113 International Publication No. 2010/137601 Korean Patent Publication No. 10-2017-0088650 International Publication No. 2021/025371 International Publication No. 2019/151682 International Publication No. 2015/050391 Specification of Chinese Patent Application Publication No. 108033886 International Publication No. 2015/084114 International Publication No. 2021/149998 Specification of Chinese Patent Application Publication No. 113045434 Specification of Chinese Patent Application Publication No. 112250585

Although many compounds for organic EL devices have been reported, compounds that further improve the performance of organic EL devices are still in demand.

The present invention has been made to solve the above problems, and has as its object the provision of a compound that further improves the performance of an organic EL device, an organic EL device having further improved device performance, and an electronic device including such an organic EL device.

The present inventors have conducted extensive studies on the performance of organic EL devices including novel compounds not disclosed in Patent Documents 1 to 13, and as a result, have found that an organic EL device including a compound represented by the following formula (1) has further improved performance. Furthermore, they have found that an organic EL device including a compound represented by the following formula (2) also has further improved performance.

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

[Chemical Formula 1]

[In equation (1),

N* is the central nitrogen atom.

Ra and Rb are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

However, Ra and Rb may be combined with each other to form a ring structure, or may not be combined with each other to form a ring structure;

When Ra and Rb do not bond to each other to form a ring structure, at least one selected from Ra and Rb is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

R ¹ to R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.

However, one selected from R ¹ to R ⁸ is a single bond bonding to *1;

At least one group of two or more adjacent groups selected from R ¹ to ^{R 8} , which are not single bonds bonded to the above *1, may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may not be bonded to each other to form a ring.

Rc is 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.

R ¹¹ to R ¹⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.

However, at least one group of two or more adjacent groups selected from R ¹¹ to R ¹⁸ may be combined with each other to form one or more substituted or unsubstituted benzene rings, or may not be combined with each other to form a ring.

R ²¹ to R ²⁴ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.

However, at least one group of two or more adjacent groups selected from R ²² to R ²⁴ may be combined with each other to form one or more substituted or unsubstituted benzene rings, or may not be combined with each other to form a ring.

L ¹ , L ² , and L ³ are each independently a single bond or an unsubstituted ring-forming arylene group having 6 to 12 carbon atoms.

Ar is a group represented by the following formula (1a), (1b), (1c), (1d), (1e), or (1f).

[Chemical formula 2]

(In equation (1a),

*11 is the binding position to L ³ .

Rd and Rf are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;

However, Rd and Rf may be combined with each other to form a ring structure, or may not be combined with each other to form a ring structure.

R ³¹ to R ³⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms;

However, one selected from R ³¹ to R ³⁸ is a single bond bonding to *12;

At least one group of two or more adjacent groups selected from R ³¹ to R ³⁸ , which are not single bonds bonded to the above *12, may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may not be bonded to each other to form a ring.)

[Chemical Formula 3]

(In equation (1b),

*21 is the binding position to L ³ .

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

R ¹⁰¹ to ^{R 105} , which are not single bonds bonding to the above *22, and R ¹⁰⁶ to R ¹¹⁰ , which are not single bonds bonding to the above *23, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

Two adjacent groups selected from R ¹⁰¹ to R ¹⁰⁵ that are not single bonds bonding to the above *22 do not bond to each other and therefore do not form a ring;

Two adjacent groups selected from R ¹⁰⁶ to R ¹¹⁰ that are not single bonds bonded to the above *23 do not bond to each other and therefore do not form a ring.

R ¹¹¹ to R ¹¹⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, two adjacent groups selected from R ¹¹¹ to ^{R 115} do not bind to each other and therefore do not form a ring.)

[Chemical Formula 4]

(In equation (1c),

*24 is the binding position to L ³ .

R ¹²¹ to R ¹²⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, one selected from R ¹²¹ to ^{R 128} is a single bond bonding to *25, and two adjacent ones selected from R ¹²¹ to R ¹²⁸ that are not single bonds bonding to *25 do not bond to each other and therefore do not form a ring.)

[Chemical Formula 5]

(In equation (1d),

*26 is the binding position to L ³ .

R ¹³¹ to R ¹⁴⁰ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, one selected from R ¹³¹ to ^{R 140} is a single bond bonding to *27, and two adjacent ones selected from R ¹³¹ to R ¹⁴⁰ that are not single bonds bonding to *27 do not bond to each other and therefore do not form a ring.)

[Chemical formula 6]

(In equation (1e),

*28 is the binding position to L ³ .

R ¹⁵¹ to R ¹⁵⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, one selected from R ¹⁵¹ to R ¹⁵⁵ is a single bond bonding to *29, and the other selected from R ¹⁵¹ to R ¹⁵⁵ is a single bond bonding to *30;

Two adjacent groups selected from R ¹⁵¹ to R ¹⁵⁵ , which are neither a single bond bonding to the above *29 nor a single bond bonding to the above *30, do not bond to each other and therefore do not form a ring.

However, if L ³ is a single bond and R ¹⁵² is a single bond bonding to *29, then R ¹⁵¹ , R ¹⁵³ , or R ¹⁵⁴ is a single bond bonding to *30;

If L ³ is a single bond, and also R ¹⁵³ is a single bond bonding to *29, then R ¹⁵² or R ¹⁵⁴ is a single bond bonding to *30;

If L ³ is a single bond and also R ¹⁵⁴ is a single bond bonding to *29, then R ¹⁵² , R ¹⁵³ , or R ¹⁵⁵ is a single bond bonding to *30.

R ¹⁶¹ to ^{R 165} and R ¹⁷¹ to R ¹⁷⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, at least one group of two or more adjacent groups selected from R ¹⁶¹ to R ¹⁶⁵ may be combined with each other to form one or more substituted or unsubstituted benzene rings, or may not be combined with each other to form a ring;

At least one group of two or more adjacent groups selected from R ¹⁷¹ to R ¹⁷⁵ may be combined with each other to form one or more substituted or unsubstituted benzene rings, or may not be combined with each other to form a ring.

[Chemical formula 7]

(In equation (1f),

*31 is the binding position to L ³ .

R ¹⁸¹ to R ¹⁹² are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, one selected from R ¹⁸¹ to ^{R 192} is a single bond bonding to *32, and two adjacent ones selected from R ¹⁸¹ to ^{R 192} that are not single bonds bonding to *32 do not bond to each other and therefore do not form a ring.)]

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

[Chemical formula 8]

[In equation (2),

N* is the central nitrogen atom.

Raa and Rbb are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

However, Raa and Rbb may be combined with each other to form a ring structure, or may not be combined with each other to form a ring structure;

When Raa and Rbb do not bond to each other to form a ring structure, at least one selected from Raa and Rbb is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

R ⁵¹ to R ⁵⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.

However, one selected from R ⁵¹ to R ⁵⁸ is a single bond bonding to *51;

At least one group of two or more adjacent groups selected from R ⁵¹ to R ⁵⁸ , which are not single bonds bonded to the above *51, may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may not be bonded to each other to form a ring.

Rcc is 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.

R ⁶¹ to R ⁶⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.

However, at least one group of two or more adjacent groups selected from R ⁶¹ to R ⁶⁸ may be combined with each other to form one or more substituted or unsubstituted benzene rings, or may not be combined with each other to form a ring.

R ⁷¹ to R ⁷⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.

However, one selected from R ⁷¹ to R ⁷⁵ is a single bond bonding to *52;

At least one group of two or more adjacent groups selected from R ⁷¹ to R ⁷⁵ , which are not single bonds bonded to the above *52, may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may not be bonded to each other to form a ring.

L ²¹ , L ²² , and L ²³ are each independently a single bond or an unsubstituted ring-forming arylene group having 6 to 12 carbon atoms.

Ar ² is a group represented by the following formula (2a), (2b), (2c), (2d), (2e), or (2f).

[Chemical formula 9]

(In equation (2a),

*61 is the binding position to L ²³ .

Rdd and Rff are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;

However, Rdd and Rff may be combined with each other to form a ring structure, or may not be combined with each other to form a ring structure.

R ⁸¹ to R ⁸⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms;

However, one selected from R ⁸¹ to R ⁸⁸ is a single bond bonding to *62;

At least one group of two or more adjacent groups selected from R ⁸¹ to R ⁸⁸ , which are not single bonds bonded to the above *62, may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may not be bonded to each other to form a ring.

[Chemical Formula 10]

(In equation (2b),

*70 is the binding position to L ²³ .

One selected from R ²⁹¹ to R ²⁹⁵ is a single bond bonding to *71, one selected from R ³⁰¹ to R ³⁰⁵ is a single bond bonding to *72, and one selected from R ³⁰⁶ to R ³¹⁰ is a single bond bonding to *73;

R ²⁹¹ to R ²⁹⁵ , which are not single bonds bonding to the above *71, R ³⁰¹ to R ³⁰⁵ , which are not single bonds bonding to the above *72, and R ³⁰⁶ to ^{R 310} , which are not single bonds bonding to the above *73, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

Two adjacent groups selected from R ²⁹¹ to R ²⁹⁵ , which are not single bonds bonding to the above *71, do not bond to each other and therefore do not form a ring;

Two adjacent groups selected from R ³⁰¹ to R ³⁰⁵ , which are not single bonds bonding to the above *72, do not bond to each other and therefore do not form a ring;

Two adjacent groups selected from R ³⁰⁶ to R ³¹⁰ that are not single bonds bonded to the above *73 do not bond to each other and therefore do not form a ring.

R ³¹¹ to R ³¹⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, two adjacent groups selected from R ³¹¹ to ^{R 315} do not bond to each other and therefore do not form a ring;

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

step,

When m, n and p are 0, *73 indicates the binding position to L ²³ ,

When m and n are 0 and also p is 1, *72 indicates the binding position to L ²³ ,

When m is 0 and also n and p are 1, *71 indicates the binding position to L ²³ ,

When m and p are 0 and n is 1, *71 represents a bonding position to L ²³ , and one selected from R ³⁰¹ to R ³⁰⁵ is a single bond bonding to *73,

When m is 1 and also n and p are 0, one selected from R ²⁹¹ to R ²⁹⁵ is a single bond bonding to *73,

When m and n are 1 and p is 0, one selected from R ³⁰¹ to R ³⁰⁵ is a single bond bonding to *73.)

[Chemical Formula 11]

(In equation (2c),

*74 is the binding position to L ²³ .

R ³²¹ to R ³²⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, one selected from R ³²¹ to ^{R 328} is a single bond bonding to *75, and two adjacent ones selected from R ³²¹ to R ³²⁸ that are not single bonds bonding to *75 do not bond to each other and therefore do not form a ring.)

[Chemical Formula 12]

(In equation (2d),

*76 is the binding position to L ²³ .

R ³³¹ to R ³⁴⁰ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, one selected from R ³³¹ to ^{R 340} is a single bond bonding to *77, and two adjacent ones selected from R ³³¹ to R ³⁴⁰ that are not single bonds bonding to *77 do not bond to each other and therefore do not form a ring.)

[Chemical Formula 13]

(In equation (2e),

*78 is the binding position to L ²³ .

R ³⁵¹ to R ³⁵⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, one selected from R ³⁵¹ to R ³⁵⁵ is a single bond binding to *79, and another selected from R ³⁵¹ to R ³⁵⁵ is a single bond binding to *80;

Two adjacent groups selected from R ³⁵¹ to R ³⁵⁵ , which are neither a single bond bonding to the above *79 nor a single bond bonding to the above *80, do not bond to each other and therefore do not form a ring.

R ³⁶¹ to ^{R 365} and R ³⁷¹ to R ³⁷⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, at least one group of two or more adjacent groups selected from R ³⁶¹ to R ³⁶⁵ may be combined with each other to form one or more substituted or unsubstituted benzene rings, or may not be combined with each other to form a ring;

At least one group of two or more adjacent groups selected from R ³⁷¹ to R ³⁷⁵ may be combined with each other to form one or more substituted or unsubstituted benzene rings, or may not be combined with each other to form a ring.

[Chemical Formula 14]

(In equation (2f),

*81 is the binding position to L ²³ .

R ³⁸¹ to R ³⁹² are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, one selected from R ³⁸¹ to ^{R 392} is a single bond bonding to *82, and two adjacent ones selected from R ³⁸¹ to R ³⁹² that are not single bonds bonding to *82 do not bond to each other and therefore do not form a ring.)

However, when L ²¹ is a single bond and Ar ² is represented by formula (2b), the structure having a fluorene skeleton bonded to *51 is not an unsubstituted spirobifluorene;

And, at least one requirement selected from the following requirements (I) and (II) is satisfied;

Requirement (I): R ⁶¹ to R ⁶⁸ , and at least one selected from R ⁷¹ to R ⁷⁵ that is not a single bond bonding to the above *52 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms;

Requirement (II): Rcc is an aryl group having 6 to 30 ring carbon atoms having at least one substituent selected from an alkyl group having 1 to 10 carbon atoms and a cycloalkyl group having 3 to 10 ring carbon atoms.]

In another aspect, the present invention provides a material for an organic EL device comprising a compound represented by the above formula (1) or a compound represented by the above formula (2).

In another aspect, the present invention provides an organic electroluminescence device comprising an anode, a cathode, and an organic layer 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 a compound represented by the formula (1) or a compound represented by the formula (2).

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

An organic EL device comprising a compound represented by the above formula (1) exhibits improved device performance. Similarly, an organic EL device comprising a compound represented by the above formula (2) exhibits improved device performance.

FIG. 1 is a schematic diagram showing an example of the layer configuration of an organic EL device according to one embodiment of the present invention.
FIG. 2 is a schematic diagram showing another example of the layer configuration of an organic EL device according to one embodiment of the present invention.
FIG. 3 is a schematic diagram showing another example of the layer configuration of an organic EL device according to one embodiment of the present invention.

[definition]

In this specification, the term hydrogen atom includes isotopes having different numbers of neutrons, i.e., protium, deuterium, and tritium.

In this specification, in a chemical structural formula, a hydrogen atom, i.e., a light hydrogen atom, a deuterium atom, or a tritium atom, is assumed to be bonded to a bondable position where a symbol such as “R” or “D” representing a deuterium atom is not specified.

In this specification, the number of ring carbon atoms represents the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., a monocyclic compound, a condensed ring compound, a bridged compound, a carbon-carbon ring compound, and a heterocyclic compound). When the ring is substituted by a substituent, the carbon contained in the substituent is not included in the number of ring carbon atoms. The "number of ring carbon atoms" recorded below shall be the same unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. In addition, for example, the number of ring carbon atoms of a 9,9-diphenylfluorenyl group is 13, and the number of ring carbon atoms of a 9,9'-spirobifluorenyl group is 25.

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

In this specification, the number of ring-forming atoms refers to the number of atoms forming the ring itself of a compound (e.g., a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a condensed ring, and a ring set). Atoms that do not form a ring (e.g., a hydrogen atom terminating a bond of atoms forming a ring) or atoms contained in a substituent when the ring is substituted by a substituent are not included in the number of ring-forming atoms. The "number of ring-forming atoms" described below shall be the same unless otherwise specified. For example, the number of ring-forming atoms of a pyridine ring is 6, the number of ring-forming atoms of a quinazoline ring is 10, and the number of ring-forming atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or atoms forming a substituent is not included in the number of pyridine ring-forming atoms. Therefore, the number of ring atoms of the pyridine ring to which the hydrogen atom or the substituent is bonded is 6. In addition, for example, the hydrogen atom bonded to the carbon atom of the quinazoline ring or the atom forming the substituent are not included in the number of ring atoms of the quinazoline ring. Therefore, the number of ring atoms of the quinazoline ring to which the hydrogen atom or the substituent is bonded is 10.

In this specification, in the expression "a substituted or unsubstituted ZZ group having XX to YY carbon atoms", "carbon atoms XX to YY" indicates the carbon number of the ZZ group when it is unsubstituted, and does not include the carbon number of the substituent when it is substituted. Here, "YY" is larger than "XX", "XX" means an integer greater than or equal to 1, and "YY" means an integer greater than or equal to 2.

In this specification, in the expression "ZZ group having a substituted or unsubstituted atomic number XX to YY", "atom number XX to YY" indicates the atomic number of the ZZ group when it is unsubstituted, and does not include the atomic number of the substituent when it is substituted. Here, "YY" is larger than "XX", "XX" means an integer greater than or equal to 1, and "YY" means an integer greater than or equal to 2.

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

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

In addition, in the present specification, in the case of "a substituted or unsubstituted ZZ group", "substitution" means that one or more hydrogen atoms in the ZZ group are substituted with a substituent. In the case of "a BB group substituted with an AA group", "substitution" similarly means that one or more hydrogen atoms in the BB group are substituted with an AA group.

"Substituents described in this specification"

Hereinafter, the substituents described in this specification are described. Unless otherwise specified, each substituent described in this specification is defined as follows.

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

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

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

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

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

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

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

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

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

· "Substituted or unsubstituted aryl group"

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

A "substituted aryl group" means a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with a substituent. As the "substituted aryl group", for example, a group in which one or more hydrogen atoms of the "unsubstituted aryl group" of the following specific example group G1A are replaced with a substituent, and examples of substituted aryl groups of the following specific example group G1B are exemplified. In addition, the examples of the "unsubstituted aryl group" and the examples of the "substituted aryl group" listed herein are merely examples, and the "substituted aryl group" described herein also includes a group in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group" of the following specific example group G1B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted aryl group" of the following specific example group G1B is further replaced with a substituent.

· Unsubstituted aryl group (specific example group G1A):

Phenyl group,

p-biphenyl group,

m-biphenyl group,

o-biphenyl group,

p-terphenyl-4-yl group,

p-terphenyl-3-yl group,

p-terphenyl-2-yl group,

m-terphenyl-4-yl group,

m-terphenyl-3-yl group,

m-terphenyl-2-yl group,

o-terphenyl-4-yl group,

o-terphenyl-3-yl,

o-terphenyl-2-yl group,

1-naphthyl group,

2-naphthyl group,

Antril group,

Benzanthryl group,

Phenanthryl group,

Benzophenanthryl group,

Penalen Diary,

Florence Diary,

Chrysen's Diary,

Benzochreisen Diary,

Triphenylene group,

Benzotriphenylene group,

Tetracen Diary,

Pentacen Diary,

Fluorene diary,

9,9'-spirobifluorene diary,

Benzofluorene diary,

Dibenzofluorene diary,

Fluoranthenium diary,

Benzofluoranthene diary,

Perylene diary, and

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

[Chemical Formula 15]

[Chemical Formula 16]

· Substituted aryl group (specific example group G1B):

o-tolyl group,

m-tolyl group,

p-tolyl group,

Para-xylyl group,

meta-xylyl group,

Ortho-xylyl group,

para-isopropylphenyl group,

meta-isopropylphenyl group,

Ortho-isopropylphenyl group,

para-t-butylphenyl group,

meta-t-butylphenyl group,

ortho-t-butylphenyl group,

3,4,5-trimethylphenyl group,

9,9-Dimethylfluorenyl group,

9,9-Diphenylfluorenyl group

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

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

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

cyanophenyl group,

Triphenylsilylphenyl group,

Trimethylsilylphenyl group,

Phenylnaphthyl group,

naphthylphenyl group, and

A group in which at least one hydrogen atom of a monovalent group derived from a ring structure represented by the above general formulae (TEMP-1) to (TEMP-15) is substituted with a substituent.

· “Substituted or unsubstituted heterocyclic group”

The "heterocyclic group" described herein is a cyclic group containing at least one hetero atom in a ring-forming atom. Specific examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.

The “heterocyclic group” described in this specification is a monocyclic group or a condensed ring group.

The “heterocyclic group” described herein is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

Specific examples (specific examples G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic groups (specific examples G2A), and substituted heterocyclic groups (specific examples G2B). (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when simply referred to as a "heterocyclic group", it includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group".

A "substituted heterocyclic group" means a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with a substituent. Specific examples of the "substituted heterocyclic group" include groups in which the hydrogen atoms of the "unsubstituted heterocyclic group" of the following specific example group G2A are substituted, and examples of substituted heterocyclic groups of the following specific example group G2B, etc. In addition, the examples of the "unsubstituted heterocyclic group" and the examples of the "substituted heterocyclic group" listed herein are merely examples, and the "substituted heterocyclic group" described in this specification also includes groups in which the hydrogen atom bonded to the 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 groups in which the hydrogen atom of the substituent in the "substituted heterocyclic group" of the specific example group G2B is further substituted with a substituent.

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

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

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

pyrrolyl group,

imidazolyl group,

Pyrazolyl group,

Triazolyl group,

Tetrazolyl group,

Oxazolyl group,

Isoxazolyl group,

Oxadiazolyl group,

Cyazolyl group,

isothiazolyl group,

Cyadiazolyl group,

Pyridyl group,

The diary of a piri-da-jin,

Pyrimidine Diary,

The Pirazin Diary,

Triazine Diary,

Indolyl,

Isoindoleyl,

Indolizine Diary,

Quinolizine diary,

Quinolyl group,

Isoquinolyl group,

Playing with new things,

Phthalazine diary,

Quinazolinic acid,

Quinoxaline Diary,

Benzimidazolyl group,

Indazolyl group,

Phenanthroline diary,

Phenanthridine diary,

Acridine Diary,

Phenazine Diary,

Carbazolyl group,

Benzocarbazolyl group,

Morpholino period,

Penok photo diary,

Phenothiazine Diary,

Azacabazolyl group, and

Diazacabazolyl group.

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

Furyl group,

Oxazolyl group,

Isoxazolyl group,

Oxadiazolyl group,

Zanten Diary,

Benzofuran diary,

Isobenzofuran diary,

Dibenzofuran diary,

Naphthobenzofuran diary,

Benzoxazolyl group,

Benzisoxazolyl group,

Penok photo diary,

Morpholino period,

Dynaptofuran diary,

Azadibenzofuran diary,

Diazadibenzofuran diary,

Azanaphthobenzofuran diary, and

Diazanaphthobenzofuran diary.

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

Cyenne Diary,

Cyazolyl group,

isothiazolyl group,

Cyadiazolyl group,

Benzothiophene diary (benzothiene diary),

Isobenzothiophene diary (isobenzothiazine diary),

Dibenzothiophene diary (dibenzothiazide diary),

Naphthobenzothiophene diary (naphthobenzothiazine diary),

Benzothiazolyl group,

Benzisothiazolyl group,

Phenothiazine Diary,

Dynaptothiophene diary (Dynaptothiene diary),

Azadibenzothiophene diary (azadibenzothiazide diary),

Diazadibenzothiophene dihydroxide (diazadibenzothiophene dihydroxide),

Azanaphthobenzothiophene dihydrochloride (azanaphthobenzothiophene dihydrochloride), and

Diazanaphthobenzothiophene dihydrate (diazanaphthobenzothiaenyl dihydrate).

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

[Chemical Formula 17]

[Chemical Formula 18]

In the above general formulas (TEMP-16) to (TEMP-33), X _A and Y _A are each independently an oxygen atom, a sulfur atom, NH, or CH _2. However, at least one of X _A and Y _A is an oxygen atom, a sulfur atom, or NH.

In the general 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 one hydrogen atom from NH or CH ₂ .

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

(9-phenyl)carbazolyl group,

(9-biphenylyl)carbazolyl group,

(9-phenyl)phenylcarbazolyl group,

(9-naphthyl)carbazolyl group,

Diphenylcarbazol-9-yl group,

Phenylcarbazol-9-yl group,

Methylbenzimidazolyl group,

Ethylbenzimidazolyl group,

Phenyltriazine dihydrate,

Biphenylyltriazine diary,

Diphenyltriazine group,

Phenylquinazolinyl group, and

Biphenylylquinazolinyl group.

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

Phenyldibenzofuran group,

Methyl dibenzofuran dibasic group,

t-butyldibenzofuran diaryl, and

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

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

Phenyldibenzothiophene diary,

Methyldibenzothiophene diary,

t-butyldibenzothiophene diary, and

A monovalent moiety of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

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

The above “one or more hydrogen atoms of a monovalent heterocyclic group” means one or more hydrogen atoms selected from a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, a hydrogen atom bonded to a nitrogen atom when at least one of X _A and Y _A is NH, and a hydrogen atom of a methylene group when one of X _A and Y _A is _CH2 .

· "Substituted or unsubstituted alkyl group"

Specific examples (specific examples G3) of the "substituted or unsubstituted alkyl group" described herein include the following unsubstituted alkyl groups (specific examples G3A) and substituted alkyl groups (specific examples G3B). (Here, the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group", and the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group".) Hereinafter, when simply referred to as "alkyl group", both an "unsubstituted alkyl group" and a "substituted alkyl group" are included.

A "substituted alkyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are replaced with a substituent. Specific examples of the "substituted alkyl group" include a group in which one or more hydrogen atoms in the following "unsubstituted alkyl group" (specific example group G3A) are replaced with a substituent, and examples of a substituted alkyl group (specific example group G3B). In the present specification, the alkyl group in the "unsubstituted alkyl group" means a chain alkyl group. Therefore, the "unsubstituted alkyl group" includes a straight-chain "unsubstituted alkyl group" and a branched "unsubstituted alkyl group." Meanwhile, the examples of the "unsubstituted alkyl group" and the examples of the "substituted alkyl group" listed herein are only examples, and the "substituted alkyl group" described in this specification also includes a group in which the hydrogen atom of the alkyl group itself in the "substituted alkyl group" of Specific Example Group G3B is further substituted with a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkyl group" of Specific Example Group G3B is further substituted with a substituent.

· Unsubstituted alkyl group (specific example group G3A):

Methyl group,

Ethyl group,

n-profiler,

Isopropyl group,

n-butyl group,

Isobutyl group,

s-butyl group, and

t-butyl group.

· Substituted alkyl group (specific example group G3B):

Heptafluoropropyl group (including isomers),

pentafluoroethyl group,

2,2,2-trifluoroethyl group, and

Trifluoromethyl group.

· "Substituted or unsubstituted alkenyl group"

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

A "substituted alkenyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are replaced with a substituent. Specific examples of the "substituted alkenyl group" include groups in which the following "unsubstituted alkenyl groups" (specific example group G4A) have a substituent, and examples of substituted alkenyl groups (specific example group G4B). In addition, the examples of the "unsubstituted alkenyl group" and the examples of the "substituted alkenyl group" listed herein are merely examples, and the "substituted alkenyl group" described in this specification also includes groups in which the hydrogen atoms of the alkenyl group itself in the "substituted alkenyl group" of specific example group G4B are further replaced with substituents, and groups in which the hydrogen atoms of the substituent in the "substituted alkenyl group" of specific example group G4B are further replaced with substituents.

· Unsubstituted alkenyl group (specific example group G4A):

Vinyl machine,

Announcement,

1-Viewten Diary,

2-View diary, and

3-Viewten Diary.

· Substituted alkenyl group (specific example group G4B):

1,3-Butanediene diary,

1-Methyl vinyl group,

1-Methylallyl group,

1,1-Dimethylallyl group,

2-Methylallyl group, and

1,2-Dimethylallyl group.

· "Substituted or unsubstituted alkyne group"

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

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

· Unsubstituted alkyne group (specific example group G5A):

Etin Diary

· “Substituted or unsubstituted cycloalkyl group”

Specific examples of the "substituted or unsubstituted cycloalkyl group" described in this specification (specific examples G6) include the following unsubstituted cycloalkyl groups (specific examples G6A), and substituted cycloalkyl groups (specific examples G6B). (Here, the unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group", and the substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group".) In this specification, when simply referred to as a "cycloalkyl group", it includes both an "unsubstituted cycloalkyl group" and a "substituted cycloalkyl group".

A "substituted cycloalkyl group" means a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are replaced with a substituent. Specific examples of the "substituted cycloalkyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted cycloalkyl group" (specific example group G6A) are replaced with a substituent, and examples of substituted cycloalkyl groups (specific example group G6B). In addition, the examples of the "unsubstituted cycloalkyl group" and the examples of the "substituted cycloalkyl group" listed herein are merely examples, and the "substituted cycloalkyl group" described in this specification also includes groups in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl group" of specific example group G6B are replaced with a substituent, and groups in which the hydrogen atom of the substituent in the "substituted cycloalkyl group" of specific example group G6B is further replaced with a substituent.

· Unsubstituted cycloalkyl group (specific example G6A):

Cyclopropyl,

Cyclobutyl group,

Cyclopentyl group,

Cyclohexyl group,

1-Adamantyl group,

2-Adamantyl group,

1-Norbornyl group, and

2-Nobornyl group.

· Substituted cycloalkyl group (specific example G6B):

4-Methylcyclohexyl group.

· A group represented by "-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ )"

Specific examples (specific example group G7) of the group represented by -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ) described in this specification 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)

can be heard. Here,

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

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

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

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

- In Si(G1)(G1)(G1), multiple G1s are identical or different.

- In Si(G1)(G2)(G2), multiple G2s are identical or different.

- In Si(G1)(G1)(G2), multiple G1s are identical or different.

- In Si(G2)(G2)(G2), multiple G2s are identical or different.

- In Si(G3)(G3)(G3), plural G3s are identical or different.

- In Si(G6)(G6)(G6), plural G6s are the same or different.

· Flags indicated by "-O-(R ₉₀₄ )"

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

-O(G1),

-O(G2),

-O(G3), and

-O(G6)

can be heard.

Here,

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

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

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

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

· Flags indicated by "-S-(R ₉₀₅ )"

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

-S(G1),

-S(G2),

-S(G3), and

-S(G6)

can be heard.

Here,

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

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

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

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

· 「-N(R ₉₀₆ )(R ₉₀₇ )」

Specific examples (specific example group G10) of the group represented by -N(R ₉₀₆ )(R ₉₀₇ ) described in this specification include:

-N(G1)(G1),

-N(G2)(G2),

-N(G1)(G2),

-N(G3)(G3), and

-N(G6)(G6)

can be heard.

Here,

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

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

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

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

- In N(G1)(G1), plural G1s are identical or different.

- In N(G2)(G2), plural G2s are identical or different.

- In N(G3)(G3), plural G3s are identical or different.

- In N(G6)(G6), plural G6s are identical or different from each other.

· "Halogen atom"

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

· “Substituted or unsubstituted fluoroalkyl group”

The "substituted or unsubstituted fluoroalkyl group" described herein means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). The carbon number of the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification. The "substituted fluoroalkyl group" means a group in which one or more hydrogen atoms of the "fluoroalkyl group" are replaced with a substituent. Meanwhile, the "substituted fluoroalkyl group" described in this specification includes a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in the "substituted fluoroalkyl group" are further substituted with a substituent, and a group in which one or more hydrogen atoms of the substituent in the "substituted fluoroalkyl group" are further substituted with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include examples of groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are substituted with a fluorine atom.

· “Substituted or unsubstituted haloalkyl group”

The "substituted or unsubstituted haloalkyl group" described herein means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The carbon number of the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification. The "substituted haloalkyl group" means a group in which one or more hydrogen atoms of the "haloalkyl group" are replaced with a substituent. Meanwhile, the "substituted haloalkyl group" described in this specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in the "substituted haloalkyl group" are further substituted with a substituent, and a group in which one or more hydrogen atoms of the substituent in the "substituted haloalkyl group" are further substituted with a substituent. Specific examples of the "unsubstituted haloalkyl group" include examples of groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced with a halogen atom. A haloalkyl group is sometimes called a halogenated alkyl group.

· “Substituted or unsubstituted alkoxy group”

A specific example of the "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), wherein 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, and more preferably 1 to 18, unless otherwise specified in this specification.

· “Substituted or unsubstituted alkylthio group”

A specific example of the "substituted or unsubstituted alkylthio group" described in this specification is a group represented by -S(G3), wherein 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, and more preferably 1 to 18, unless otherwise specified in this specification.

· “Substituted or unsubstituted aryloxy group”

A specific example of the "substituted or unsubstituted aryloxy group" described in this specification is a group represented by -O(G1), wherein 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, and more preferably 6 to 18, unless otherwise specified in this specification.

· "Substituted or unsubstituted aryl thio group"

A specific example of the "substituted or unsubstituted arylthio group" described in this specification is a group represented by -S(G1), wherein 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, and more preferably 6 to 18, unless otherwise specified in this specification.

· “Substituted or unsubstituted trialkylsilyl group”

A specific example of the "trialkylsilyl group" described in this specification is a group represented by -Si(G3)(G3)(G3), wherein G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3. In -Si(G3)(G3)(G3), multiple G3s are the same as or different from each other. The number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in this specification.

· “Substituted or unsubstituted aralkyl group”

A specific example of the "substituted or unsubstituted aralkyl group" described in the present specification is a group represented by -(G3)-(G1), wherein 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. Therefore, the "aralkyl group" is a group in which a hydrogen atom of the "alkyl group" is substituted with an "aryl group" as a substituent, and is one embodiment of the "substituted alkyl group". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group" in which an "unsubstituted aryl group" is substituted, and the number of carbon atoms of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in the present specification.

Specific examples of the “substituted or unsubstituted aralkyl group” include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butyl group, an α-naphthylmethyl group, a 1-α-naphthylethyl group, a 2-α-naphthylethyl group, a 1-α-naphthylisopropyl group, a 2-α-naphthylisopropyl group, a β-naphthylmethyl group, a 1-β-naphthylethyl group, a 2-β-naphthylethyl group, a 1-β-naphthylisopropyl group, and a 2-β-naphthylisopropyl group.

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

The substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an azadibenzothiophenyl group, Examples thereof include a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazol-4-yl group), a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenyldibenzofuranyl group, and a phenyldibenzothiophenyl group.

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

[Chemical Formula 19]

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

[Chemical formula 20]

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

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

[Chemical Formula 21]

In the above general formulas (TEMP-34) to (TEMP-41), * indicates a bonding position.

The substituted or unsubstituted alkyl groups described in this specification are preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, and a t-butyl group, unless otherwise specified in this specification.

· "Substituted or unsubstituted arylene group"

The "substituted or unsubstituted arylene group" described herein, unless otherwise specified, is a divalent group derived from the "substituted or unsubstituted aryl group" by removing one hydrogen atom on the aryl ring. Specific examples of the "substituted or unsubstituted arylene group" (specific example group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in specific example group G1 by removing one hydrogen atom on the aryl ring.

· “Substituted or unsubstituted divalent heterocyclic group”

The “substituted or unsubstituted divalent heterocyclic group” described herein, unless otherwise specified, is a divalent group derived from the “substituted or unsubstituted heterocyclic group” by removing one hydrogen atom on the heterocycle. Specific examples of the “substituted or unsubstituted divalent heterocyclic group” (specific example group G13) include divalent groups derived from the “substituted or unsubstituted heterocyclic group” described in specific example group G2 by removing one hydrogen atom on the heterocycle.

· “Substituted or unsubstituted alkylene group”

The "substituted or unsubstituted alkylene group" described herein, unless otherwise specified, is a divalent group derived from the "substituted or unsubstituted alkyl group" by removing one hydrogen atom on the alkyl chain. Specific examples of the "substituted or unsubstituted alkylene group" (specific example group G14) include divalent groups derived from the "substituted or unsubstituted alkyl group" described in specific example group G3 by removing one hydrogen atom on the alkyl chain.

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

[Chemical Formula 22]

[Chemical Formula 23]

In the above general formulas (TEMP-42) to (TEMP-52), Q ₁ to Q ₁₀ are each independently a hydrogen atom or a substituent.

In the above general formulas (TEMP-42) to (TEMP-52), * indicates a bonding position.

[Chemical Formula 24]

In the above general formulas (TEMP-53) to (TEMP-62), Q ₁ to Q ₁₀ are each independently a hydrogen atom or a substituent.

Formulas Q ₉ and Q ₁₀ may be combined with each other via a single bond to form a ring.

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

[Chemical Formula 25]

In the above general formulas (TEMP-63) to (TEMP-68), Q ₁ to Q ₈ are each independently a hydrogen atom or a substituent.

In the above general formulas (TEMP-63) to (TEMP-68), * indicates a bonding position.

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

[Chemical Formula 26]

[Chemical Formula 27]

[Chemical formula 28]

In the above general formulas (TEMP-69) to (TEMP-82), Q ₁ to Q ₉ are each independently a hydrogen atom or a substituent.

[Chemical formula 29]

[Chemical formula 30]

[Chemical Formula 31]

[Chemical Formula 32]

In the above general formulas (TEMP-83) to (TEMP-102), Q ₁ to Q ₈ are each independently a hydrogen atom or a substituent.

The above is a description of the “substituents described in this specification.”

· "When combined to form a ring"

In the present specification, when it is said that “one or more groups consisting of two or more adjacent groups are combined with each other to form a substituted or unsubstituted monocyclic ring, or are combined with each other to form a substituted or unsubstituted condensed ring, or are not combined with each other”, it means that “one or more groups consisting of two or more adjacent groups are combined with each other to form a substituted or unsubstituted monocyclic ring,” “one or more groups consisting of two or more adjacent groups are combined with each other to form a substituted or unsubstituted condensed ring,” and “one or more groups consisting of two or more adjacent groups are not combined with each other.”

In the present specification, the case where "one or more groups consisting of two or more adjacent groups are combined with each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more groups consisting of two or more adjacent groups are combined with each other to form a substituted or unsubstituted condensed ring" (hereinafter, these cases may be collectively referred to as "cases of combining to form a ring") are described below. The case of an anthracene compound represented by the following general formula (TEMP-103) in which the parent skeleton is an anthracene ring is described as an example.

[Chemical formula 33]

For example, in the case where "at least one group of groups consisting of two or more adjacent groups are combined with each other to form a ring" among R ₉₂₁ to R ₉₃₀ , the groups consisting of two adjacent groups that form group 1 are: the group of R ₉₂₁ and R ₉₂₂ , the group of R ₉₂₂ and R ₉₂₃ , the group of R ₉₂₃ and R ₉₂₄ , the group of R ₉₂₄ and R ₉₃₀ , the group of R ₉₃₀ and R ₉₂₅ , the group of R ₉₂₅ and R ₉₂₆ , the group of R ₉₂₆ and R ₉₂₇ , the group of R ₉₂₇ and R ₉₂₈ , the group of R ₉₂₈ and R ₉₂₉ , and the group of R ₉₂₉ and R ₉₂₁ .

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

[Chemical Formula 34]

The case where "a group composed of two or more adjacent groups" forms a ring includes not only the case where a group composed of "two" adjacent groups combine as in the above-mentioned example, but also the case where a group composed of "three or more" adjacent groups combine. For example, it means the case where R ₉₂₁ and R ₉₂₂ combine with each other to form ring Q _A , furthermore R ₉₂₂ and R ₉₂₃ combine with each other to form ring Q _C , and a group composed of three adjacent groups (R ₉₂₁ , R ₉₂₂ and R ₉₂₃ ) combine with each other to form a ring and condense on an anthracene parent skeleton, and in this case, the 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), ring Q _A and ring Q _C share R ₉₂₂ .

[Chemical Formula 35]

The formed "monocyclic ring" or "fused ring" has a structure of only the formed ring, and may be a saturated ring or an unsaturated ring. Even in the case where "a group of two adjacent rings" forms a "monocyclic ring" or a "fused ring", the "monocyclic ring" or "fused ring" can form a saturated ring or an unsaturated ring. For example, in the general formula (TEMP-104), the formed ring Q _A and the ring Q _B are each a "monocyclic ring" or a "fused ring". In addition, in the general formula (TEMP-105), the formed ring Q _A and the ring Q _C are a "fused ring". The ring Q _A and the ring Q _C of the general formula (TEMP-105) become a fused ring by the condensation of 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 monocyclic ring. If ring Q _A of the above general formula (TEMP-104) is a naphthalene ring, ring Q _A is a condensed ring.

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

As a specific example of an aromatic hydrocarbon ring, a structure in which the group mentioned as a specific example in the specific example group G1 is terminated by a hydrogen atom can be mentioned.

As a specific example of an aromatic heterocycle, a structure in which an aromatic heterocycle group is terminated by a hydrogen atom as a specific example in the specific example group G2 can be mentioned.

As a specific example of an aliphatic hydrocarbon ring, a structure in which the group listed as a specific example in the specific example group G6 is terminated by a hydrogen atom can be mentioned.

"Forming a ring" means forming a ring with only a plurality of atoms of the parent skeleton, or with a plurality of atoms of the parent skeleton and one or more arbitrary elements. For example, the ring Q _A formed by R ₉₂₁ and R ₉₂₂ bonding to each other, shown in the general formula (TEMP-104), means a ring formed by the carbon atom of the anthracene skeleton to which R ₉₂₁ is bonded, the carbon atom of the anthracene skeleton to which R ₉₂₂ is bonded, and one or more arbitrary elements. As a specific example, in the case where ring Q _A is formed by R ₉₂₁ and R ₉₂₂ , when a monocyclic unsaturated ring is formed by the carbon atom of the anthracene skeleton to which R ₉₂₁ is bonded, the carbon atom of the anthracene skeleton to which R ₉₂₂ is bonded, and four carbon atoms, the ring formed by R ₉₂₁ and R ₉₂₂ is a benzene ring.

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

Unless otherwise specified in this specification, the “one or more arbitrary elements” constituting the monocyclic ring or condensed ring are preferably 2 to 15, more preferably 3 to 12, and even more preferably 3 to 5.

Unless otherwise specified in this specification, among “single ring” and “condensed ring”, “single ring” is preferred.

Unless otherwise specified in this specification, among “saturated ring” and “unsaturated ring”, “unsaturated ring” is preferred.

Unless otherwise specified in this specification, “monocyclic” is preferably a benzene ring.

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

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

In the case where the above "single ring" or "fused ring" has a substituent, the substituent is, for example, an "arbitrary substituent" described below. Specific examples of the substituent in the case where the above "single ring" or "fused ring" has a substituent are the substituents described in the above-mentioned "substituents described in the present specification."

In the case where the above "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, an "arbitrary substituent" described below. In the case where the above "monocyclic ring" or "condensed ring" has a substituent, a specific example of the substituent is the substituent described in the above-mentioned "substituent described in the present specification" section.

The above is an explanation of the case where "at least one group consisting of two or more adjacent groups combines with each other to form a substituted or unsubstituted monocyclic ring" and the case where "at least one group consisting of two or more adjacent groups combines with each other to form a substituted or unsubstituted condensed ring" ("when combined to form a ring").

· Substituents in cases where it is said to be “substituted or unsubstituted”

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

Unsubstituted alkenyl group having 2 to 50 carbon atoms,

Unsubstituted alkyne group having 2 to 50 carbon atoms,

An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atom, cyano group, nitro group,

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

Heterocyclic group having 5 to 50 unsubstituted ring atoms

A group selected from the group consisting of, etc.

Here, R ₉₀₁ to R ₉₀₇ are, independently,

hydrogen atom,

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

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

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

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

When two or more R _901s exist, two or more R _901s are identical to each other or different,

When two or more R _902s exist, two or more R _902s are identical to each other or different,

When two or more R _903s exist, two or more R _903s are identical to each other or different,

When two or more R _904s exist, two or more R _904s are identical or different from each other,

When two or more R _905s exist, two or more R _905s are identical or different from each other,

When two or more R _906s exist, two or more R _906s are identical or different from each other,

When two or more R _907s exist, two or more R _907s are identical or different from each other.

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

Alkyl group having 1 to 50 carbon atoms,

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

Heterocyclic ring with 5 to 50 ring atoms

A group selected from the group consisting of .

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

Alkyl group having 1 to 18 carbon atoms,

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

Heterocyclic ring with 5 to 18 ring atoms

A group selected from the group consisting of .

Specific examples of each of the above arbitrary substituents are specific examples of the substituents described in the above-mentioned “Substituents described in the present specification.”

Unless otherwise specified herein, adjacent arbitrary substituents may form a “saturated ring” or an “unsaturated ring”, preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, and more preferably a benzene ring.

Unless otherwise specified in this specification, any substituent may additionally have a substituent. The substituent additionally possessed by the optional substituent is the same as the optional substituent described above.

In this specification, the numerical range indicated using “AA∼BB” means a range that includes the numerical value AA described before “AA∼BB” as the lower limit and the numerical value BB described after “AA∼BB” as the upper limit.

Hereinafter, the compound of the present invention is described.

A compound according to one aspect of the present invention is represented by the following formula (1) or (2), as described above.

In this specification, there are cases where a compound of the present invention represented by the formula described below and included in formula (1) is referred to as "inventive compound (1)". In addition, there are cases where a compound of the present invention represented by the formula described below and included in formula (2) is referred to as "inventive compound (2)".

In this specification, in order to express the meaning of “inventive compound (1) alone, inventive compound (2) alone, or both of inventive compounds (1) and (2),” the term is sometimes simply referred to as “inventive compound.”

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

[Chemical formula 36]

Below, the symbols in formula (1) and each formula described later included in formula (1) are explained. Unless specifically stated otherwise, the same symbols have the same meaning.

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

In formula (1), Ra and Rb are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

However, Ra and Rb may be combined with each other to form a ring structure, or may not be combined with each other to form a ring structure;

When Ra and Rb do not bond to each other to form a ring structure, at least one selected from Ra and Rb is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

The carbon number of the unsubstituted alkyl group having 1 to 30 carbon atoms that Ra and Rb can represent is each independently preferably 1 to 18, more preferably 1 to 6.

As the unsubstituted alkyl group having 1 to 30 carbon atoms that Ra and Rb can represent, examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, or a dodecyl group;

Preferably, it is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, or a hexyl group;

More preferably, it is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, or a t-butyl group;

More preferably, it is a methyl group, an ethyl group, or a t-butyl group;

More preferably, it is a methyl group.

In addition, as a substituent that the unsubstituted alkyl group having 1 to 30 carbon atoms that Ra and Rb can represent may have, for example, any of the substituents described below can be mentioned.

The number of ring carbon atoms of the unsubstituted ring-forming aryl group having 6 to 30 ring carbon atoms that Ra and Rb can represent is each independently preferably 6 to 18, more preferably 6 to 12.

As the unsubstituted aryl group having 6 to 30 ring carbon atoms that Ra and Rb can represent, examples thereof include a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, anthryl group, a benzanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a picenyl group, a pentaphenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a fluorenyl group, a fluoranthenyl group, a perylenyl group, or a triphenylenyl group;

Preferably, it is a phenyl group, a biphenylyl group, a terphenylyl group, or a naphthyl group;

More preferably, it is a phenyl group, a 2-, 3-, or 4-biphenylyl group, a 2-, 3-, or 4-o-terphenylyl group, a 2-, 3-, or 4-m-terphenylyl group, a 2-, 3-, or 4-p-terphenylyl group, or a 1- or 2-naphthyl group;

More preferably, it is a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group;

More preferably, it is a phenyl group.

In addition, as a substituent that the unsubstituted ring-forming aryl group having 6 to 30 carbon atoms that Ra and Rb can represent may have, examples thereof include any of the substituents described below, but among them, an alkyl group having 1 to 6 carbon atoms is preferable; more preferably, a methyl group or a t-butyl group.

As the substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms that Ra and Rb can represent, it is preferably an aromatic heterocyclic group (heteroaryl group) having 5 to 30 ring atoms that is substituted or unsubstituted.

The number of ring atoms of the unsubstituted heterocyclic group having 5 to 30 ring atoms that Ra and Rb can represent is each independently preferably 5 to 20, more preferably 5 to 13.

As the above unsubstituted heterocyclic group having 5 to 30 ring atoms that Ra and Rb can represent, for example, a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, an imidazopyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a pyrazolyl group, an isoxazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a tetrazolyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolizinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, Benzoxazolyl group, benzothiazolyl group, indazolyl group, benzisoxazolyl group, benzisothiazolyl group, phenanthridinyl group, acridinyl group, phenanthrolineyl group, phenazinyl group, phenothiazinyl group, phenoxazinyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, naphthobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group (alias "benzothienyl group", the same applies hereinafter), isobenzothiphenyl group (alias "isobenzothienyl group", the same applies hereinafter), naphthobenzothiphenyl group (alias "naphthobenzothienyl group", the same applies hereinafter), dibenzothiphenyl group (alias "dibenzothienyl group", the same applies hereinafter), or A carbazolyl group (including a 9-carbazolyl group, or a 1-, 2-, 3- or 4-carbazolyl group; the same applies hereinafter) may be mentioned;

Preferably, it is 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 benzofuranyl group, an isobenzofuranyl group, a naphthobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group, an isobenzothiophenyl group, a naphthobenzothiophenyl group, a dibenzothiophenyl group, or a carbazolyl group;

More preferably, it is a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.

In addition, as a substituent that the heterocyclic group having 5 to 30 ring-forming atoms that Ra and Rb can represent may have, for example, any of the substituents described below can be mentioned.

When Ra and Rb are combined with each other to form a ring structure, the ring structure may be a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle, and is selected from, for example, a monocyclic ring, a condensed ring, a bridged bicyclocycle, or a bridged tricyclocycle.

Specific examples of the ring structures that Ra and Rb can form by combining with each other are shown below, but are not limited to these. In the ring structures shown below, * indicates a bonding position to the benzene ring of the fluorene skeleton.

[Chemical Formula 37]

In addition, when Ra and Rb are combined with each other to form a ring structure, the ring structure is preferably a substituted or unsubstituted hydrocarbon ring.

In addition, in one embodiment of the above-described compound (1), as the ring structure that Ra and Rb may form by bonding to each other, for example, among the specific examples described above, the following ring structures are preferable.

[Chemical formula 38]

In formula (1), R ¹ to ^{R 8} are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.

However, one selected from R ¹ to R ⁸ is a single bond bonding to *1;

At least one group of two or more adjacent groups selected from R ¹ to ^{R 8} , which are not single bonds bonded to the above *1, may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may not be bonded to each other to form a ring.

In one embodiment of the above-mentioned inventive compound (1), preferably, one selected from R ² to ^{R 7} is a single bond bonding to *1, and more preferably, R ² or R ⁷ is a single bond bonding to *1.

As the unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R ¹ to R ⁸ , examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, or a decyl group;

Preferably, it is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, or a hexyl group;

More preferably, it is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, or a t-butyl group; even more preferably, it is a methyl group or a t-butyl group;

More preferably, it is a t-butyl group.

As the unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ¹ to R ⁸ , examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-norbornyl group, a 2-norbornyl group, a 1-adamantyl group, or a 2-adamantyl group;

Preferably, it is a cyclohexyl group, a 1-norbornyl group, a 2-norbornyl group, a 1-adamantyl group, or a 2-adamantyl group;

More preferably, it is a cyclohexyl group, a 1-adamantyl group, or a 2-adamantyl group.

As the unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ¹ to R ⁸ , examples thereof include a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, anthryl group, a benzanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a pyrenyl group, a chrysenyl group, a fluorenyl group, a fluoranthenyl group, or a triphenylenyl group;

Preferably, it is a phenyl group, a biphenylyl group, a terphenylyl group, or a naphthyl group;

More preferably, it is a phenyl group, a 2-, 3-, or 4-biphenylyl group, a 2-, 3-, or 4-o-terphenylyl group, a 2-, 3-, or 4-m-terphenylyl group, a 2-, 3-, or 4-p-terphenylyl group, or a 1- or 2-naphthyl group;

More preferably, it is a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group;

More preferably, it is a phenyl group.

As the unsubstituted heterocyclic group having 5 to 13 ring atoms that can be represented by R ¹ to R ⁸ , examples thereof include those exemplified for the heterocyclic group that can be represented by Ra and Rb , except for those having 5 to 13 ring atoms;

Preferably, it is 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 benzofuranyl group, an isobenzofuranyl group, a naphthobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group, an isobenzothiophenyl group, a naphthobenzothiophenyl group, a dibenzothiophenyl group, or a carbazolyl group;

More preferably, it is a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.

In formula (1), Rc is 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.

The details of the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms that can be represented by Rc are the same as those described for the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms that can be represented by Ra and Rb, and suitable embodiments thereof are also the same.

Therefore, suitable examples of the unsubstituted alkyl group having 1 to 30 carbon atoms that Rc can represent are preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, or a hexyl group; more preferably, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, or a t-butyl group; more preferably, a methyl group, an ethyl group, or a t-butyl group; and still more preferably, a methyl group.

In addition, as a substituent that the unsubstituted alkyl group having 1 to 30 carbon atoms that Rc can represent may have, for example, any of the substituents described below can be mentioned.

The details of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms that can be represented by Rc are the same as those described for the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms that can be represented by Ra and Rb, and suitable embodiments thereof are also the same.

Therefore, suitable examples of the unsubstituted aryl group having 6 to 30 ring carbon atoms that Rc can represent are preferably a phenyl group, a biphenylyl group, a terphenylyl group, or a naphthyl group; more preferably, a phenyl group, a 2-, 3-, or 4-biphenylyl group, a 2-, 3-, or 4-o-terphenylyl group, a 2-, 3-, or 4-m-terphenylyl group, a 2-, 3-, or 4-p-terphenylyl group, or a 1- or 2-naphthyl group; more preferably, a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group; still more preferably, a phenyl group.

In addition, as a substituent that the unsubstituted ring-forming aryl group having 6 to 30 carbon atoms that Rc can represent may have, examples thereof include any of the substituents described below, but among them, an alkyl group having 1 to 6 carbon atoms is preferable; more preferably, a methyl group or a t-butyl group.

In formula (1), R ¹¹ to R ¹⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.

However, at least one group of two or more adjacent groups selected from R ¹¹ to R ¹⁸ may be combined with each other to form one or more substituted or unsubstituted benzene rings, or may not be combined with each other to form a ring.

The details of the substituted or unsubstituted alkyl group having ¹ to 10 carbon atoms that can be represented by R ¹¹ to R ¹⁸ are the same as those described for the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by the above R 1 to R ⁸ ;

Accordingly, the types of alkyl groups, preferred alkyl groups, more preferred alkyl groups, more preferred alkyl groups, and even more preferred alkyl groups, which are exemplified as the unsubstituted alkyl groups having 1 to 10 carbon atoms that R ¹¹ to R ¹⁸ can represent, are each the same as those exemplified in the description of R ¹ to R ⁸ .

The details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ¹¹ to R ¹⁸ are the same as those described for the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of cycloalkyl groups, preferred cycloalkyl groups, and more preferred cycloalkyl groups exemplified as the unsubstituted ring-forming cycloalkyl groups having 3 to 10 carbon atoms that can be represented by R ¹¹ to ^{R 18} are each the same as those exemplified in the description of R ¹ to R ⁸ .

The details of the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ¹¹ to R ¹⁸ are the same as those described for the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of aryl groups, preferred aryl groups, more preferred aryl groups, more preferred aryl groups, and even more preferred aryl groups, which are exemplified as the aryl groups having ⁶ to ¹⁸ unsubstituted ring-forming carbon atoms that can be represented by R 11 to R 18, are each the same as those exemplified in the description of R ¹ to R ⁸ .

The details of the substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms that can be represented by R ¹¹ to R ¹⁸ are the same as those described for the substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of heterocyclic groups, preferred heterocyclic groups, and more preferred heterocyclic groups exemplified as the unsubstituted ring-forming heterocyclic groups having 5 to 13 ring atoms that can be represented by R ¹¹ to R ¹⁸ are also the same as those exemplified in the description of R ¹ to R ⁸ , respectively.

In formula (1), R ²¹ to R ²⁴ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.

However, at least one group of two or more adjacent groups selected from R ²² to R ²⁴ may be combined with each other to form one or more substituted or unsubstituted benzene rings, or may not be combined with each other to form a ring.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R ²¹ to R ²⁴ are the same as those described for the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of alkyl groups, preferred alkyl groups, more preferred alkyl groups, more preferred alkyl groups, and even more preferred alkyl groups, which are exemplified as the unsubstituted alkyl groups having 1 to 10 carbon atoms that R ²¹ to R ²⁴ can represent, are each the same as those exemplified in the description of R ¹ to R ⁸ .

The details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ²¹ to R ²⁴ are the same as those described for the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of cycloalkyl groups, preferred cycloalkyl groups, and more preferred cycloalkyl groups exemplified as the unsubstituted ring-forming cycloalkyl groups having 3 to 10 carbon atoms that can be represented by R ²¹ to R ²⁴ are each the same as those exemplified in the description of R ¹ to R ⁸ .

The details of the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ²¹ to R ²⁴ are the same as those described for the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of aryl groups, preferred aryl groups, more preferred aryl groups, more preferred aryl groups, and even more preferred aryl groups, which are exemplified as the aryl groups having ^{6 to 18} unsubstituted ring-forming carbon atoms that can be represented by R 21 to R 24, are each the same as those exemplified in the description of R ¹ to R ⁸ .

The details of the substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms that can be represented by R ²¹ to R ²⁴ are the same as those described for the substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of heterocyclic groups, preferred heterocyclic groups, and more preferred heterocyclic groups exemplified as the unsubstituted ring-forming heterocyclic groups having 5 to 13 ring atoms that can be represented by R ²¹ to R ²⁴ are each the same as those exemplified in the description of R ¹ to R ⁸ .

In formula (1), L ¹ , L ² , and L ³ are each independently a single bond or an unsubstituted ring-forming arylene group having 6 to 12 carbon atoms.

As the unsubstituted arylene group having 6 to 12 ring carbon atoms that can be represented by L ¹ , L ² , and L ^{3 ,} a divalent group obtained by removing one hydrogen atom from the unsubstituted aryl group described for Ra and Rb , except for those having 6 to 12 ring carbon atoms, can be exemplified, and an unsubstituted phenylene group, an unsubstituted naphthylene group, or an unsubstituted biphenylene group can be exemplified; an unsubstituted phenylene group is more preferable.

The unsubstituted phenylene group that L ¹ , L ² , and L ³ can represent is an o-phenylene group, an m-phenylene group, or a p-phenylene group.

The unsubstituted naphthylene group which L ¹ , L ² , and L ³ can represent is preferably a 1,4-naphthylene group or a 2,6-naphthylene group.

The unsubstituted biphenylene group which L ¹ , L ² , and L ³ can represent is preferably a 4,4'-biphenylene group, a 4,3'-biphenylene group (same as "3,4'-biphenylene group"), or a 4,2'-biphenylene group (same as "2,4'-biphenylene group").

In formula (1), Ar is a group represented by formula (1a), (1b), (1c), (1d), (1e), or (1f).

[Chemical Formula 39]

In formula (1a), *11 is the binding position to L ³ .

In formula (1a), Rd and Rf are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;

However, Rd and Rf may be combined with each other to form a ring structure, or may not be combined with each other to form a ring structure.

The details of the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms that can be represented by Rd and Rf are the same as those described for the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms that can be represented by Ra and Rb;

Accordingly, the types of alkyl groups, preferred alkyl groups, more preferred alkyl groups, more preferred alkyl groups, and even more preferred alkyl groups, which are exemplified as the unsubstituted ring-forming alkyl groups having 1 to 30 carbon atoms that can be represented by Rd and Rf, are the same as those exemplified in the description of Ra and Rb, respectively;

In addition, as a substituent that the unsubstituted alkyl group having 1 to 30 carbon atoms that can be represented by Rd and Rf may have, for example, any of the substituents described below can be exemplified.

The details of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms that can be represented by Rd and Rf are the same as those described for the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms that can be represented by the above Ra and Rb;

Accordingly, the types of aryl groups, preferred aryl groups, more preferred aryl groups, more preferred aryl groups, and even more preferred aryl groups, which are exemplified as the unsubstituted aryl groups having 6 to 30 ring carbon atoms that can be represented by Rd and Rf, are the same as those exemplified in the description of Ra and Rb, respectively;

In addition, as a substituent that the unsubstituted ring-forming aryl group having 6 to 30 carbon atoms that can be represented by Rd and Rf may have, examples thereof include any of the substituents described below, but among them, an alkyl group having 1 to 6 carbon atoms is preferable; more preferably, a methyl group or a t-butyl group.

The details of the substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms that can be represented by Rd and Rf are the same as those described for the substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms that can be represented by the above Ra and Rb;

Accordingly, the types of heterocyclic groups exemplified as the unsubstituted ring-forming heterocyclic groups having 5 to 30 ring atoms that can be represented by Rd and Rf, and more preferable heterocyclic groups, are the same as those exemplified in the description of Ra and Rb, respectively;

In addition, as a substituent that the heterocyclic group having 5 to 30 ring-forming atoms that can be represented by Rd and Rf may have, for example, any of the substituents described below can be exemplified.

When Rd and Rf combine with each other to form a ring structure, the details of the ring structure that Rd and Rf may form by combining with each other are the same as those described with respect to the ring structure that Ra and Rb may form by combining with each other;

Accordingly, specific examples of ring structures that can be formed by combining Rd and Rf with each other, and suitable ring structures thereof, are the same as those exemplified in the description of Ra and Rb.

In one embodiment of the above-described compound (1), the group represented by the above-described formula (1a) is preferably represented by the following formula. However, in the following formula, the single bonds bonded to *11 and *12, which indicate bonding positions to L ³ , and R ³¹ to R ³⁸ are omitted for simplicity.

[Chemical formula 40]

In formula (1a), R ³¹ to R ³⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.

However, one selected from R ³¹ to R ³⁸ is a single bond bonding to *12;

At least one group of two or more adjacent groups selected from R ³¹ to R ³⁸ , which are not single bonds bonded to the above *12, may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may not be bonded to each other to form a ring.

In one embodiment of the above-mentioned inventive compound, preferably, one selected from R ³² to ^{R 37} is a single bond bonding to *12, and more preferably, R ³² or R ³⁷ is a single bond bonding to *12.

The details of the substituted or unsubstituted alkyl group having ¹ to 10 carbon atoms that can be represented by R ³¹ to ^{R 38} are the same as those described for the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by the above R 1 to R ⁸ ;

Accordingly, the types of alkyl groups, preferred alkyl groups, more preferred alkyl groups, more preferred alkyl groups, and even more preferred alkyl groups, which are exemplified as the unsubstituted alkyl groups having 1 to 10 carbon atoms that R ³¹ to R ³⁸ can represent, are each the same as those exemplified in the description of R ¹ to R ⁸ .

The details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ³¹ to R ³⁸ are the same as those described for the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of cycloalkyl groups, preferred cycloalkyl groups, and more preferred cycloalkyl groups exemplified as the unsubstituted ring-forming cycloalkyl groups having 3 to 10 carbon atoms that can be represented by R ³¹ to R ³⁸ are each the same as those exemplified in the description of R ¹ to R ⁸ .

The details of the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ³¹ to R ³⁸ are the same as those described for the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of aryl groups, preferred aryl groups, more preferred aryl groups, more preferred aryl groups, and even more preferred aryl groups, which are exemplified as the aryl groups having ⁶ to ¹⁸ unsubstituted ring-forming carbon atoms that can be represented by R 31 to R 38, are each the same as those exemplified in the description of R ¹ to R ⁸ .

The details of the substituted or unsubstituted heterocyclic group having ^{5 to} 13 ring atoms that can be represented by R ³¹ to ^{R 38} are the same as those described for the substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms that can be represented by the above R 1 to R ⁸ ;

Accordingly, the types of heterocyclic groups, preferred heterocyclic groups, and more preferred heterocyclic groups exemplified as the unsubstituted ring-forming heterocyclic groups having 5 to 13 ring atoms that can be represented by R ³¹ to R ³⁸ are also the same as those exemplified in the description of R ¹ to R ⁸ , respectively.

[Chemical Formula 41]

In formula (1b), *21 is the binding position to L ³ .

In formula (1b), one selected from R ¹⁰¹ to R ¹⁰⁵ is a single bond bonding to *22, and one selected from R ¹⁰⁶ to R ¹¹⁰ is a single bond bonding to *23;

R ¹⁰¹ to ^{R 105} , which are not single bonds bonding to the above *22, and R ¹⁰⁶ to R ¹¹⁰ , which are not single bonds bonding to the above *23, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

Two adjacent groups selected from R ¹⁰¹ to R ¹⁰⁵ that are not single bonds bonding to the above *22 do not bond to each other and therefore do not form a ring;

Two adjacent groups selected from R ¹⁰⁶ to R ¹¹⁰ that are not single bonds bonded to the above *23 do not bond to each other and therefore do not form a ring.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R ¹⁰¹ to R ¹⁰⁵ and R ¹⁰⁶ to R ¹¹⁰ are the same as those described for the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of alkyl groups, preferred alkyl groups, more preferred alkyl groups, more preferred alkyl groups, and still more preferred alkyl groups, which are exemplified as ^the unsubstituted alkyl groups having ¹ to ¹⁰ carbon atoms that can be represented by R ¹⁰¹ to R 105 and R 106 to R 110, are the same as those exemplified in the description of R ¹ to R ⁸ , respectively.

The details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ¹⁰¹ to R ¹⁰⁵ and R ¹⁰⁶ to R ¹¹⁰ are the same as those described for the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of cycloalkyl groups, preferred cycloalkyl groups, and more preferred cycloalkyl groups exemplified as the unsubstituted ring-forming cycloalkyl groups having 3 to 10 carbon atoms that can be represented by R ¹⁰¹ to R ¹⁰⁵ and R ¹⁰⁶ to R ¹¹⁰ are also the same as those exemplified in the description of R ¹ to R ⁸ , respectively.

The details of the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ¹⁰¹ to R ¹⁰⁵ and R ¹⁰⁶ to R ¹¹⁰ are the same as those described for the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, ^the types of aryl groups, preferred aryl groups, more preferred aryl groups, ^{more preferred} aryl groups, and even more preferred aryl groups, which are exemplified as the aryl groups having 6 to ¹⁸ unsubstituted ring-forming carbon atoms that can be represented by R 101 to R 105 and R 106 to R 110, are each the same as those exemplified in the description of R ¹ to R ⁸ .

In formula (1b), R ¹¹¹ to R ¹¹⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, two adjacent groups selected from R ¹¹¹ to ^{R 115} do not bond with each other and therefore do not form a ring.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R ¹¹¹ to R ¹¹⁵ are the same as those described for the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of alkyl groups, preferred alkyl groups, more preferred alkyl groups, more preferred alkyl groups, and even more preferred alkyl groups, which are exemplified as the unsubstituted alkyl groups having 1 to 10 carbon atoms that R ¹¹¹ to R ¹¹⁵ can represent, are each the same as those exemplified in the description of R ¹ to R ⁸ .

The details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ¹¹¹ to R ¹¹⁵ are the same as those described for the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of cycloalkyl groups, preferred cycloalkyl groups, and more preferred cycloalkyl groups exemplified as the unsubstituted ring-forming cycloalkyl groups having 3 to 10 carbon atoms that can be represented by R ¹¹¹ to R ¹¹⁵ are each the same as those exemplified in the description of R ¹ to R ⁸ .

The details of the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ¹¹¹ to R ¹¹⁵ are the same as those described for the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of aryl groups, preferred aryl groups, more preferred aryl groups, more preferred aryl groups, and even more preferred aryl groups, which are exemplified as the aryl groups having ⁶ to ¹⁸ unsubstituted ring-forming carbon atoms that can be represented by R 111 to R 115, are each the same as those exemplified in the description of R ¹ to R ⁸ .

The group represented by the above formula (1b) includes each group represented by the following formula. However, in the formula below, R ¹⁰¹ to ^{R 105} , R ¹⁰⁶ to R ¹¹⁰ , and R ¹¹¹ to ^{R 115} , which are not single bonds, are omitted for simplicity.

[Chemical formula 42]

[Chemical formula 43]

In formula (1c), *24 is the binding position to L ³ .

In formula (1c), R ¹²¹ to R ¹²⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, one selected from R ¹²¹ to ^{R 128} is a single bond bonding to *25, and two adjacent selected from R ¹²¹ to R ¹²⁸ that are not single bonds bonding to *25 do not bond to each other and therefore do not form a ring.

The details of the substituted or unsubstituted alkyl group having ¹ to 10 carbon atoms that can be represented by R ¹²¹ to R ¹²⁸ are the same as those described for the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by the above R 1 to R ⁸ ;

Accordingly, the types of alkyl groups, preferred alkyl groups, more preferred alkyl groups, more preferred alkyl groups, and even more preferred alkyl groups, which are exemplified as the unsubstituted alkyl groups having 1 to 10 carbon atoms that R ¹²¹ to R ¹²⁸ can represent, are each the same as those exemplified in the description of R ¹ to ^{R 8} .

The details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ¹²¹ to R ¹²⁸ are the same as those described for the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of cycloalkyl groups, preferred cycloalkyl groups, and more preferred cycloalkyl groups exemplified as the unsubstituted ring-forming cycloalkyl groups having 3 to 10 carbon atoms that can be represented by R ¹²¹ to R ¹²⁸ are each the same as those exemplified in the description of R ¹ to R ⁸ .

The details of the substituted or unsubstituted aryl group having ⁶ to 18 ring carbon atoms that can be represented by R ¹²¹ to R ¹²⁸ are the same as those described for the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by the above R 1 to R ⁸ ;

Accordingly, the types of aryl groups, preferred aryl groups, more preferred aryl groups, more preferred aryl groups, and even more preferred aryl groups, which are exemplified as the aryl groups having ⁶ to ¹⁸ unsubstituted ring-forming carbon atoms that can be represented by R 121 to R 128, are each the same as those exemplified in the description of R ¹ to R ⁸ .

[Chemical Formula 44]

In formula (1d), *26 is the binding position to L ³ .

In formula (1d), R ¹³¹ to R ¹⁴⁰ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, one selected from R ¹³¹ to ^{R 140} is a single bond bonding to *27, and two adjacent selected from R ¹³¹ to R ¹⁴⁰ that are not single bonds bonding to *27 do not bond to each other and therefore do not form a ring.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R ¹³¹ to R ¹⁴⁰ are the same as those described for the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of alkyl groups, preferred alkyl groups, more preferred alkyl groups, more preferred alkyl groups, and even more preferred alkyl groups, which are exemplified as the unsubstituted alkyl groups having 1 to 10 carbon atoms that R ¹³¹ to R ¹⁴⁰ can represent, are each the same as those exemplified in the description of R ¹ to ^{R 8} .

The details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ¹³¹ to R ¹⁴⁰ are the same as those described for the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of cycloalkyl groups, preferred cycloalkyl groups, and more preferred cycloalkyl groups exemplified as the unsubstituted ring-forming cycloalkyl groups having 3 to 10 carbon atoms that can be represented by R ¹³¹ to R ¹⁴⁰ are each the same as those exemplified in the description of R ¹ to R ⁸ .

The details of the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ¹³¹ to R ¹⁴⁰ are the same as those described for the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of aryl groups, preferred aryl groups, more preferred aryl groups, more preferred aryl groups, and even more preferred aryl groups, which are exemplified as the aryl groups having ⁶ to ¹⁸ unsubstituted ring-forming carbon atoms that can be represented by R 131 to R 140, are each the same as those exemplified in the description of R ¹ to R ⁸ .

[Chemical Formula 45]

In formula (1e), *28 is the binding position to L ³ .

In formula (1e), R ¹⁵¹ to R ¹⁵⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, one selected from R ¹⁵¹ to R ¹⁵⁵ is a single bond bonding to *29, and the other selected from R ¹⁵¹ to R ¹⁵⁵ is a single bond bonding to *30;

Two adjacent groups selected from R ¹⁵¹ to R ¹⁵⁵ , which are neither a single bond bonding to the above *29 nor a single bond bonding to the above *30, do not bond to each other and therefore do not form a ring.

However, if L ³ is a single bond and R ¹⁵² is a single bond bonding to *29, then R ¹⁵¹ , R ¹⁵³ , or R ¹⁵⁴ is a single bond bonding to *30;

If L ³ is a single bond, and also R ¹⁵³ is a single bond bonding to *29, then R ¹⁵² or R ¹⁵⁴ is a single bond bonding to *30;

If L ³ is a single bond and also R ¹⁵⁴ is a single bond bonding to *29, then R ¹⁵² , R ¹⁵³ , or R ¹⁵⁵ is a single bond bonding to *30.

In addition, in one embodiment of the present invention, when L ³ is a single bond and R ¹⁵² is a single bond bonding to *29, R ¹⁵¹ , R ¹⁵³ , or R ¹⁵⁴ is a single bond bonding to *30, R ¹⁵⁵ may be a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 10 to 18 ring carbon atoms.

In addition, in one embodiment of the present invention, when L ³ is a single bond and R ¹⁵⁴ is a single bond bonding to *29, one selected from R ¹⁵² , R ¹⁵³ , or R ¹⁵⁴ is a single bond bonding to *30, and R ¹⁵¹ may be a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 10 to 18 ring carbon atoms.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R ¹⁵¹ to R ¹⁵⁵ are the same as those described for the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of alkyl groups, preferred alkyl groups, more preferred alkyl groups, more preferred alkyl groups, and even more preferred alkyl groups, which are exemplified as the unsubstituted alkyl groups having 1 to ¹⁰ carbon atoms that can be represented by R ¹⁵¹ to R 155, are each the same as those exemplified in the description of R ¹ to R ⁸ .

The details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ¹⁵¹ to R ¹⁵⁵ are the same as those described for the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of cycloalkyl groups, preferred cycloalkyl groups, and more preferred cycloalkyl groups exemplified as the unsubstituted ring-forming cycloalkyl groups having 3 to 10 carbon atoms that can be represented by R ¹⁵¹ to R ¹⁵⁵ are each the same as those exemplified in the description of R ¹ to R ⁸ .

The details of the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ¹⁵¹ to R ¹⁵⁵ are the same as those described for the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of aryl groups, preferred aryl groups, more preferred aryl groups, more preferred aryl groups, and even more preferred aryl groups, which are exemplified as the aryl groups having ⁶ to ¹⁸ unsubstituted ring-forming carbon atoms that can be represented by R 151 to R 155, are each the same as those exemplified in the description of R ¹ to R ⁸ .

In one embodiment of the present invention, when L ³ is a single bond, the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that R ¹⁵¹ to R ¹⁵⁵ can represent may be a substituted or unsubstituted aryl group having 10 to 18 ring carbon atoms.

In addition, in one embodiment of the present invention, the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ¹⁵¹ to R ¹⁵⁵ may be a substituted or unsubstituted aryl group having 10 to 18 ring carbon atoms.

In formula (1e), R ¹⁶¹ to ^{R 165} and R ¹⁷¹ to R ¹⁷⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, at least one group of two or more adjacent groups selected from R ¹⁶¹ to R ¹⁶⁵ may be combined with each other to form one or more substituted or unsubstituted benzene rings, or may not be combined with each other to form a ring;

At least one group of two or more adjacent groups selected from R ¹⁷¹ to R ¹⁷⁵ may be combined with each other to form one or more substituted or unsubstituted benzene rings, or may not be combined with each other to form a ring.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R ¹⁶¹ to R ¹⁶⁵ and R ¹⁷¹ to R ¹⁷⁵ are the same as those described for the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of alkyl ^groups , preferred alkyl groups, more preferred alkyl groups, more preferred alkyl groups, and still more preferred alkyl groups, which are exemplified as ^the unsubstituted alkyl groups having 1 to ¹⁰ carbon atoms that can be represented by R ¹⁶¹ to R 165 and R 171 to R 175, are also the same as those exemplified in the description of R ¹ to ^{R 8} , respectively.

The details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ¹⁶¹ to ^{R 165} and R ¹⁷¹ to R ¹⁷⁵ are the same as those described for the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ¹ to R ⁸ ;

Accordingly, the types of cycloalkyl groups, preferred cycloalkyl groups, and more preferred cycloalkyl groups exemplified as the unsubstituted ring-forming cycloalkyl groups having 3 to 10 carbon atoms that can be represented by R ¹⁶¹ to R ¹⁶⁵ and R ¹⁷¹ to R ¹⁷⁵ are also the same as those exemplified in the description of R ¹ to R ⁸ , respectively.

The details of the substituted or unsubstituted aryl group having ^{6 to} 18 ring carbon atoms that can be represented by R ¹⁶¹ to ^{R 165} and R ¹⁷¹ to R ¹⁷⁵ are the same as those described for the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by the above R 1 to R ⁸ ;

Accordingly, the types of aryl groups, preferred aryl groups, more preferred aryl groups, ^more preferred aryl groups, and even more preferred aryl groups, which are exemplified as the aryl groups having ^{6 to 18} unsubstituted ring-forming carbon atoms that can be represented by R 161 to R 165 and R 171 to R 175, are also the same as those exemplified in the description of R ¹ to R ⁸ , respectively.

In one embodiment of the present invention, when L ³ is a single bond, the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ¹⁶¹ to R ¹⁶⁵ and R ¹⁷¹ to R ¹⁷⁵ may be a substituted or unsubstituted aryl group having 10 to 18 ring carbon atoms.

In addition, in one embodiment of the present invention, the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ¹⁶¹ to ^{R 165} and R ¹⁷¹ to R ¹⁷⁵ may be a substituted or unsubstituted aryl group having 10 to 18 ring carbon atoms.

In one embodiment of the present invention, when L ³ is a single bond, in the formula (1e), R ¹⁵¹ to R ¹⁵⁵ , and R ¹⁶¹ to R ¹⁶⁵ and R ¹⁷¹ to R ¹⁷⁵ , which are neither a single bond bonding to *29 nor a single bond bonding to *30, may each independently be a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms.

In addition, in one embodiment of the present invention, in the formula (1e), R ¹⁵¹ to ^{R 155} , and R 161 to R ¹⁶⁵ and R ¹⁷¹ to R ¹⁷⁵ , which are neither a single bond bonding to *29 nor a single bond bonding to * ³⁰ , may each independently be a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms.

The group represented by the above formula (1e) includes groups represented by the following formulas (1e-1) to (1e-5). However, when L ³ is a single bond, the group represented by the above formula (1e) includes groups represented by the following formulas (1e-1), (1e-2), (1e-3), and (1e-5).

[Chemical Formula 46]

In formulas (1e-1), (1e-2), (1e-3), (1e-4) and (1e-5), *28, R ¹⁵¹ to R ¹⁵⁵ , R ¹⁶¹ to ^{R 165} and R ¹⁷¹ to R ¹⁷⁵ are as defined in the above formula (1e), and suitable embodiments thereof are also the same.

[Chemical formula 47]

In formula (1f), *31 is the binding position to L ³ .

In formula (1f), R ¹⁸¹ to ^{R 192} are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, one selected from R ¹⁸¹ to ^{R 192} is a single bond bonding to *32, and two adjacent selected from R ¹⁸¹ to ^{R 192} that are not single bonds bonding to *32 do not bond to each other and therefore do not form a ring.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R ¹⁸¹ to R ¹⁹² are the same as those described for the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of alkyl groups, preferred alkyl groups, more preferred alkyl groups, more preferred alkyl groups, and even more preferred alkyl groups, which are exemplified as the unsubstituted alkyl groups having 1 to ¹⁰ carbon atoms that can be represented by R ¹⁸¹ to R 192, are each the same as those exemplified in the description of R ¹ to R ⁸ .

The details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ¹⁸¹ to R ¹⁹² are the same as those described for the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of cycloalkyl groups, preferred cycloalkyl groups, and more preferred cycloalkyl groups exemplified as the unsubstituted ring-forming cycloalkyl groups having 3 to 10 carbon atoms that can be represented by R ¹⁸¹ to R ¹⁹² are also the same as those exemplified in the description of R ¹ to R ⁸ , respectively.

The details of the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ¹⁸¹ to R ¹⁹² are the same as those described for the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by the above R ¹ to R ⁸ ;

Accordingly, the types of aryl groups, preferred aryl groups, more preferred aryl groups, more preferred aryl groups, and even more preferred aryl groups, which are exemplified as the aryl groups having ⁶ to ¹⁸ unsubstituted ring-forming carbon atoms that can be represented by R 181 to R 192, are each the same as those exemplified in the description of R ¹ to R ⁸ .

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

(1-1) *All of R ¹ to R ⁸ that are not single bonds bonded to 1 may be hydrogen atoms;

(1-2) All of R ¹¹ to ^{R 18} may be hydrogen atoms;

(1-3) All of R ²¹ to ^{R 24} may be hydrogen atoms;

(1-4) *All of R ³¹ to R ^38, which are not single bonds bonding to 12, may be hydrogen atoms;

(1-5) *All of R ¹⁰¹ to R ¹⁰⁵ that are not single bonds bonded to 22 may be hydrogen atoms;

(1-6) *All of R ¹⁰⁶ to R ^110, which are not single bonds bonding to 23, may be hydrogen atoms;

(1-7) All of R ¹¹¹ to ^{R 115} may be hydrogen atoms;

(1-8) *All of R ¹²¹ to R ^128, which are not single bonds bonding to 25, may be hydrogen atoms;

(1-9) *All of R ¹³¹ to R ^140, which are not single bonds bonding to 27, may be hydrogen atoms;

(1-10) *It is not a single bond bonding to 29, nor is it a single bond bonding to 30, but all of R ¹⁵¹ - R ¹⁵⁵ can be hydrogen atoms;

(1-11) All of R ¹⁶¹ to R ¹⁶⁵ may be hydrogen atoms;

(1-12) All of R ¹⁷¹ to R ¹⁷⁵ may be hydrogen atoms;

(1-13) *All of R ¹⁸¹ to R ¹⁹² that are not single bonds bonding to 32 may be hydrogen atoms.

In one embodiment of the above-described compound (1), it is preferable that all of R ¹ to R ⁸ , R ¹¹ to ^{R 18} , and R ²¹ to R ²⁴ , which are not single bonds bonded to *1 in formula (1), are hydrogen atoms.

In one embodiment of the above-described compound (1), in formula (1), it is preferable that Ra and Rb are each independently an unsubstituted aryl group having 6 to 12 ring carbon atoms; it is more preferable that both Ra and Rb are unsubstituted aryl groups having 6 to 12 ring carbon atoms; it is even more preferable that both Ra and Rb are unsubstituted phenyl groups.

In one embodiment of the above-described compound (1), in formula (1), it is preferable that Rc is an unsubstituted aryl group having 6 to 12 ring carbon atoms, and more preferably an unsubstituted phenyl group.

In one embodiment of the above-described compound (1), it is preferable that Ra, Rb and Rc in formula (1) are each independently a substituted or unsubstituted phenyl group; it is more preferable that Ra, Rb and Rc are all substituted or unsubstituted phenyl groups; it is even more preferable that Ra, Rb and Rc are all unsubstituted phenyl groups.

In one embodiment of the above-described compound (1), in formula (1), it is preferable that L ¹ and L ² are each independently a single bond or an unsubstituted phenylene group; it is more preferable that both L ¹ and L ² are a single bond or an unsubstituted phenylene group; it is even more preferable that both L ¹ and L ² are a single bond.

In one embodiment of the above-described compound (1), in formula (1), it is preferable that L ³ is a single bond or an unsubstituted phenylene group; and it is more preferable that L ³ is a single bond.

In one embodiment of the above-described compound (1), it is more preferable that all of L ¹ , L ² and L ³ in formula (1) are single bonds or unsubstituted phenylene groups; it is even more preferable that all of L ¹ , L ² and L ³ are single bonds.

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

In one embodiment of the above-described compound (1), it is preferable that in formula (1), Ar is a group represented by formula (1a), and further, in formula (1a), one selected from R ³² to ^{R 37} is a single bond bonding to *12; it is more preferable that Ar is a group represented by formula (1a), and further, in formula (1a), R ³² or R ³⁷ is a single bond bonding to *12.

In one embodiment of the above-described compound (1), it is preferable that in formula (1), L ³ is a single bond, Ar is a group represented by formula (1b), and further, in formula (1b), R ¹⁰¹ or R ¹⁰⁵ is a single bond bonded to *22.

In one embodiment of the above-described compound (1), in formula (1), when Ar is a group represented by formula (1b) and L ³ is an unsubstituted phenylene group, it is preferable that the unsubstituted phenyl group represented by L ³ is an o-phenylene group.

In addition, in one embodiment of the above-described compound (1), one or more kinds selected from the requirements of each suitable embodiment described above can be appropriately combined.

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

In addition, a deuterium atom may be intentionally introduced into the invention compound (1) by using a compound in which part or all of the raw material compound is deuterated. Therefore, in one embodiment of the present invention, the invention compound (1) contains at least one deuterium atom. That is, the invention compound (1) may be a compound represented by 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 hydrogen atoms below may be a deuterium atom. In the meantime, in the following, "substituted or unsubstituted", the number of carbon atoms and the number of atoms are omitted for simplicity. One hydrogen atom of the corresponding substituent according to the above "substituted or unsubstituted", or at least one hydrogen atom selected from two or more hydrogen atoms may also be the above deuterium atom.

A hydrogen atom possessed by an alkyl group, aryl group, or heterocyclic group that can be represented by Ra in formula (1);

A hydrogen atom possessed by an alkyl group, aryl group, or heterocyclic group that can be represented by Rb in formula (1);

A hydrogen atom having a ring structure that can be formed by combining Ra and Rb of formula (1);

A hydrogen atom that can be represented by any of R ¹ to R ⁸ , but not a single bond bonding to *1 in formula (1);

A hydrogen atom possessed by an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group that is not a single bond bonded to *1 in formula (1) and which can be represented by any of R ¹ to R ⁸ ;

A hydrogen atom of one or more benzene rings which can be formed by combining one or more groups of two or more adjacent groups selected from R ¹ to R ⁸ , which are not single bonds bonded to *1 in formula (1);

A hydrogen atom of an alkyl group or an aryl group that can be represented by Rc in formula (1);

A hydrogen atom that can be represented by any of R ¹¹ to R ¹⁸ in formula (1);

A hydrogen atom possessed by an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group which can be represented by any of R ¹¹ to R ¹⁸ in formula (1);

A hydrogen atom possessed by one or more benzene rings which can be formed by combining at least two adjacent groups selected from R ¹¹ to R ¹⁸ of formula (1);

A hydrogen atom that can be represented by any of R ²¹ to R ²⁴ in formula (1);

A hydrogen atom possessed by an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group which can be represented by any of R ²¹ to R ²⁴ in formula (1);

A hydrogen atom possessed by one or more benzene rings which can be formed by combining at least two adjacent groups selected from R ²² to R ²⁴ of formula (1);

A hydrogen atom possessed by an arylene group that can be represented by L ¹ in formula (1);

A hydrogen atom possessed by an arylene group that can be represented by L ² in formula (1);

Hydrogen atom of an arylene group that can be represented by L ³ in formula (1);

A hydrogen atom possessed by an alkyl group, an aryl group, or a heterocyclic group that can be represented by Rd in formula (1a);

A hydrogen atom possessed by an alkyl group, an aryl group, or a heterocyclic group that can be represented by Rf of formula (1a);

A hydrogen atom having a ring structure that can be formed by combining Rd and Rf of formula (1a);

A hydrogen atom that can be represented by any of R ³¹ to R ³⁸ , but not a single bond bonding to *12 in formula (1a);

A hydrogen atom possessed by an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group that may be represented by any of R ³¹ to R ³⁸ , but which is not a single bond bonded to *12 of formula (1a);

A hydrogen atom of one or more benzene rings which can be formed by combining with each other one or more groups of two or more adjacent groups selected from R ³¹ to R ³⁸ , which are not single bonds bonding to *12 of formula (1a);

A hydrogen atom which can be represented by any of R ¹⁰¹ to ^{R 105} , but not a single bond bonding to *22 of formula (1b);

A hydrogen atom of an alkyl group, cycloalkyl group, or aryl group that can be represented by any of R ¹⁰¹ to R ¹⁰⁵ , but not a single bond bonding to *22 of formula (1b);

A hydrogen atom which can be represented by any of R ¹⁰⁶ to ^{R 110} , but not a single bond bonding to *23 in formula (1b);

A hydrogen atom of an alkyl group, cycloalkyl group, or aryl group that can be represented by any of R ¹⁰⁶ to R ¹¹⁰ , but not a single bond bonding to *23 of formula (1b);

A hydrogen atom which can be represented by any of R ¹¹¹ to R ¹¹⁵ in formula (1b);

A hydrogen atom of an alkyl group, a cycloalkyl group, or an aryl group which can be represented by any of R ¹¹¹ to R ¹¹⁵ in formula (1b);

A hydrogen atom that can be represented by any of R ¹²¹ to R ¹²⁸ , but not a single bond bonding to *25 in formula (1c);

A hydrogen atom of an alkyl group, cycloalkyl group, or aryl group that can be represented by any of R ¹²¹ to R ¹²⁸ , but not a single bond bonding to *25 of formula (1c);

A hydrogen atom which can be represented by any of R ¹³¹ to ^{R 140} , but not a single bond bonding to *27 of formula (1d);

A hydrogen atom of an alkyl group, a cycloalkyl group, or an aryl group that may be represented by any of R ¹³¹ to R ¹⁴⁰ , but is not a single bond bonded to *27 of formula (1d);

A hydrogen atom that can be represented by any of R ¹⁵¹ to R ¹⁵⁵ , which is neither a single bond bonded to *29 of formula (1e) nor a single bond bonded to *30;

A hydrogen atom of an alkyl group, a cycloalkyl group, or an aryl group that is not a single bond bonded to *29 of formula (1e) nor a single bond bonded to *30 and can be represented by any of R ¹⁵¹ to ^{R 155} ;

A hydrogen atom which can be represented by any of R ¹⁶¹ to R ¹⁶⁵ in formula (1e);

A hydrogen atom of an alkyl group, a cycloalkyl group, or an aryl group which can be represented by any of R ¹⁶¹ to R ¹⁶⁵ of formula (1e);

A hydrogen atom of one or more benzene rings which can be formed by combining at least two adjacent groups selected from R ¹⁶¹ to R ¹⁶⁵ of formula (1e);

A hydrogen atom which can be represented by any of R ¹⁷¹ to R ¹⁷⁵ in formula (1e);

A hydrogen atom of an alkyl group, a cycloalkyl group, or an aryl group which can be represented by any of R ¹⁷¹ to R ¹⁷⁵ of formula (1e);

A hydrogen atom possessed by one or more benzene rings which can be formed by combining with each other at least one group of two or more adjacent groups selected from R ¹⁷¹ to R ¹⁷⁵ of formula (1e);

A hydrogen atom that can be represented by any of R ¹⁸¹ to ^{R 192} , but not a single bond bonding to *32 in formula (1f);

A hydrogen atom possessed by an alkyl group, cycloalkyl group, or aryl group that can be represented by any of R ¹⁸¹ to R ¹⁹² , but not a single bond bonding to *32 of formula (1f).

The compound (2) of the invention according to one aspect of the present invention is represented by the following formula (2).

[Chemical formula 48]

Below, the symbols in formula (2) and each formula included in formula (2) are explained. Unless specifically stated otherwise, the same symbols have the same meaning.

In equation (2), N* is the central nitrogen atom.

In formula (2), Raa and Rbb are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

However, Raa and Rbb may be combined with each other to form a ring structure, or may not be combined with each other to form a ring structure;

When Raa and Rbb do not bond to each other to form a ring structure, at least one selected from Raa and Rbb is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

The carbon number of the unsubstituted alkyl group having 1 to 30 carbon atoms that Raa and Rbb can represent is each independently preferably 1 to 18, more preferably 1 to 6.

As the unsubstituted alkyl group having 1 to 30 carbon atoms that Ra and Rb can represent, examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, or a dodecyl group;

Preferably, it is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, or a hexyl group;

More preferably, it is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, or a t-butyl group;

More preferably, it is a methyl group, an ethyl group, or a t-butyl group;

More preferably, it is a methyl group.

In addition, as a substituent that the unsubstituted alkyl group having 1 to 30 carbon atoms that Raa and Rbb can represent may have, for example, any of the substituents described below can be mentioned.

The number of ring carbon atoms of the unsubstituted ring-forming aryl group having 6 to 30 ring carbon atoms that Raa and Rbb can represent is each independently preferably 6 to 18, more preferably 6 to 12.

As the unsubstituted aryl group having 6 to 30 ring carbon atoms that can be represented by Raa and Rbb, examples thereof include a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, anthryl group, a benzanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a picenyl group, a pentaphenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a fluorenyl group, a fluoranthenyl group, a perylenyl group, or a triphenylenyl group;

Preferably, it is a phenyl group, a biphenylyl group, a terphenylyl group, or a naphthyl group;

More preferably, it is a phenyl group, a 2-, 3-, or 4-biphenylyl group, a 2-, 3-, or 4-o-terphenylyl group, a 2-, 3-, or 4-m-terphenylyl group, a 2-, 3-, or 4-p-terphenylyl group, or a 1- or 2-naphthyl group;

More preferably, it is a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group;

More preferably, it is a phenyl group.

In addition, as a substituent that the unsubstituted ring-forming aryl group having 6 to 30 carbon atoms that Raa and Rbb can represent may have, examples thereof include any of the substituents described below, but among them, an alkyl group having 1 to 6 carbon atoms is preferable; more preferably, a methyl group or a t-butyl group.

As the substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms that Raa and Rbb can represent, it is preferably an aromatic heterocyclic group (heteroaryl group) having 5 to 30 ring atoms that is substituted or unsubstituted.

The number of ring atoms of the unsubstituted heterocyclic group having 5 to 30 ring atoms that Raa and Rbb can represent is each independently preferably 5 to 20, more preferably 5 to 13.

As the above unsubstituted ring-forming heterocyclic group having 5 to 30 atoms which Raa and Rbb can represent, for example, a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, an imidazopyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a pyrazolyl group, an isoxazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a tetrazolyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolizinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, Benzoxazolyl group, benzothiazolyl group, indazolyl group, benzisoxazolyl group, benzisothiazolyl group, phenanthridinyl group, acridinyl group, phenanthrolineyl group, phenazinyl group, phenothiazinyl group, phenoxazinyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, naphthobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group (alias "benzothienyl group", the same applies hereinafter), isobenzothiphenyl group (alias "isobenzothienyl group", the same applies hereinafter), naphthobenzothiphenyl group (alias "naphthobenzothienyl group", the same applies hereinafter), dibenzothiphenyl group (alias "dibenzothienyl group", the same applies hereinafter), or A carbazolyl group (including a 9-carbazolyl group, or a 1-, 2-, 3- or 4-carbazolyl group; the same applies hereinafter) may be mentioned;

Preferably, it is 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 benzofuranyl group, an isobenzofuranyl group, a naphthobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group, an isobenzothiophenyl group, a naphthobenzothiophenyl group, a dibenzothiophenyl group, or a carbazolyl group;

More preferably, it is a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.

In addition, as a substituent that the heterocyclic group having 5 to 30 ring atoms that Raa and Rbb can represent may have, for example, any of the substituents described below can be mentioned.

When Raa and Rbb are combined with each other to form a ring structure, the ring structure may be a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle, and is selected from, for example, a monocyclic ring, a condensed ring, a bridged bicyclocycle, or a bridged tricyclocycle.

Specific examples of the ring structures that Raa and Rbb can form by combining with each other are shown below, but are not limited to these. In the ring structures shown below, * indicates a bonding position to the benzene ring of the fluorene skeleton.

[Chemical Formula 49]

In addition, when Raa and Rbb are combined with each other to form a ring structure, the ring structure is preferably a substituted or unsubstituted hydrocarbon ring.

In addition, in one embodiment of the above-described compound (2), as the ring structure that Raa and Rbb may form by combining with each other, for example, among the specific examples described above, the following ring structures are preferable.

[Chemical formula 50]

In formula (2), R ⁵¹ to R ⁵⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.

However, one selected from R ⁵¹ to R ⁵⁸ is a single bond bonding to *51;

At least one group of two or more adjacent groups selected from R ⁵¹ to R ⁵⁸ , which are not single bonds bonded to the above *51, may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may not be bonded to each other to form a ring.

In one embodiment of the above-mentioned inventive compound (2), preferably, one selected from R ⁵² to R ⁵⁷ is a single bond bonding to *51, and more preferably, R ⁵² or R ⁵⁷ is a single bond bonding to *51.

As the unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R ⁵¹ to R ⁵⁸ , examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, or a decyl group;

Preferably, it is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, or a hexyl group;

More preferably, it is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, or a t-butyl group; even more preferably, it is a methyl group or a t-butyl group.

As the unsubstituted ring-forming cycloalkyl group having 3 to 10 carbon atoms that can be represented by R ⁵¹ to R ⁵⁸ , examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-norbornyl group, a 2-norbornyl group, a 1-adamantyl group, or a 2-adamantyl group;

Preferably, it is a cyclohexyl group, a 1-norbornyl group, a 2-norbornyl group, a 1-adamantyl group, or a 2-adamantyl group;

More preferably, it is a cyclohexyl group, a 1-adamantyl group, or a 2-adamantyl group.

As the unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ⁵¹ to R ⁵⁸ , examples thereof include a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, anthryl group, a benzanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a pyrenyl group, a chrysenyl group, a fluorenyl group, a fluoranthenyl group, or a triphenylenyl group;

Preferably, it is a phenyl group, a biphenylyl group, a terphenylyl group, or a naphthyl group;

More preferably, it is a phenyl group, a 2-, 3-, or 4-biphenylyl group, a 2-, 3-, or 4-o-terphenylyl group, a 2-, 3-, or 4-m-terphenylyl group, a 2-, 3-, or 4-p-terphenylyl group, or a 1- or 2-naphthyl group;

More preferably, it is a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group;

More preferably, it is a phenyl group.

As the unsubstituted heterocyclic group having 5 to 13 ring atoms that can be represented by R ⁵¹ to R ⁵⁸ , examples thereof include those exemplified for the heterocyclic group that can be represented by Raa and Rbb, except for those having 5 to 13 ring atoms;

Preferably, it is 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 benzofuranyl group, an isobenzofuranyl group, a naphthobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group, an isobenzothiophenyl group, a naphthobenzothiophenyl group, a dibenzothiophenyl group, or a carbazolyl group;

More preferably, it is a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.

In formula (2), Rcc is 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.

The details of the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms that can be represented by Rcc are the same as those described for the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms that can be represented by Raa and Rbb, and suitable embodiments thereof are also the same.

Therefore, suitable examples of the unsubstituted alkyl group having 1 to 30 carbon atoms that Rcc can represent are preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, or a hexyl group; more preferably, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, or a t-butyl group; more preferably, a methyl group, an ethyl group, or a t-butyl group; and still more preferably, a methyl group.

In addition, as a substituent that the unsubstituted alkyl group having 1 to 30 carbon atoms that can be represented by Rcc may have, for example, any of the substituents described below can be mentioned.

The details of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms that can be represented by Rcc are the same as those described for the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms that can be represented by Raa and Rbb, and suitable embodiments thereof are also the same.

Therefore, suitable examples of the unsubstituted aryl group having 6 to 30 ring carbon atoms that Rcc can represent are preferably a phenyl group, a biphenylyl group, a terphenylyl group, or a naphthyl group; more preferably, a phenyl group, a 2-, 3-, or 4-biphenylyl group, a 2-, 3-, or 4-o-terphenylyl group, a 2-, 3-, or 4-m-terphenylyl group, a 2-, 3-, or 4-p-terphenylyl group, or a 1- or 2-naphthyl group; more preferably, a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group; still more preferably, a phenyl group.

In addition, as a substituent that the unsubstituted ring-forming aryl group having 6 to 30 carbon atoms that can be represented by Rcc may have, examples thereof include any of the substituents described below, but among them, an alkyl group having 1 to 6 carbon atoms is preferable; more preferably, a methyl group or a t-butyl group.

In formula (2), R ⁶¹ to R ⁶⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.

However, at least one group of two or more adjacent groups selected from R ⁶¹ to R ⁶⁸ may be combined with each other to form one or more substituted or unsubstituted benzene rings, or may not be combined with each other to form a ring.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R ⁶¹ to R ⁶⁸ are the same as those described for the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of alkyl groups, preferred alkyl groups, more preferred alkyl groups, more preferred alkyl groups, and even more preferred alkyl groups, which are exemplified as the unsubstituted alkyl groups having 1 to 10 carbon atoms that R ⁶¹ to R ⁶⁸ can represent, are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

The details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ⁶¹ to R ⁶⁸ are the same as those described for the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of cycloalkyl groups, preferred cycloalkyl groups, and more preferred cycloalkyl groups exemplified as the unsubstituted ring-forming cycloalkyl groups having 3 to 10 carbon atoms that can be represented by R ⁶¹ to R ⁶⁸ are also the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ , respectively.

The details of the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ⁶¹ to R 68 are the same as those described for the substituted or unsubstituted aryl group having 6 to ¹⁸ ring carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of aryl groups, preferred aryl groups, more preferred aryl groups, more preferred aryl groups, and even more preferred aryl groups, which are exemplified as the aryl groups having ⁶ to ¹⁸ unsubstituted ring-forming carbon atoms that can be represented by R 61 to R 68, are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

The details of the substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms that can be represented by R ⁶¹ to R ⁶⁸ are the same as those described for the substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of heterocyclic groups, preferred heterocyclic groups, and more preferred heterocyclic groups exemplified as the unsubstituted ring-forming heterocyclic groups having 5 to 13 ring atoms that can be represented by R ⁶¹ to R ⁶⁸ are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

In formula (2), R ⁷¹ to R ⁷⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.

However, one selected from R ⁷¹ to R ⁷⁵ is a single bond bonding to *52;

At least one group of two or more adjacent groups selected from R ⁷¹ to R ⁷⁵ , which are not single bonds bonded to the above *52, may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may not be bonded to each other to form a ring.

In one embodiment of the above-described compound (2), preferably, R ⁷² , R ⁷³ , or R ⁷⁴ is a single bond bonding to *52, and more preferably, R ⁷² , or R ⁷⁴ is a single bond bonding to *52.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R ⁷¹ to R ⁷⁵ are the same as those described for the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of alkyl groups, preferred alkyl groups, more preferred alkyl groups, more preferred alkyl groups, and still more preferred alkyl groups, which are exemplified as the unsubstituted alkyl groups having 1 to 10 carbon atoms that R ⁷¹ to R ⁷⁵ can represent, are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

The details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ⁷¹ to R ⁷⁵ are the same as those described for the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of cycloalkyl groups, preferred cycloalkyl groups, and more preferred cycloalkyl groups exemplified as the unsubstituted ring-forming cycloalkyl groups having 3 to 10 carbon atoms that can be represented by R ⁷¹ to R ⁷⁵ are also the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ , respectively.

The details of the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ⁷¹ to R ⁷⁵ are the same as those described for the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of aryl groups, preferred aryl groups, more preferred aryl groups, more preferred aryl groups, and even more preferred aryl groups, which are exemplified as the aryl groups having ⁶ to ¹⁸ unsubstituted ring-forming carbon atoms that can be represented by R 71 to R 75, are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

The details of the substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms that can be represented by R ⁷¹ to R ⁷⁵ are the same as those described for the substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of heterocyclic groups, preferred heterocyclic groups, and more preferred heterocyclic groups exemplified as the unsubstituted ring-forming heterocyclic groups having 5 to 13 ring atoms that can be represented by R ⁷¹ to R ⁷⁵ are also the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ , respectively.

In formula (2), L ²¹ , L ²² , and L ²³ are each independently a single bond or an unsubstituted ring-forming arylene group having 6 to 12 carbon atoms.

As the unsubstituted arylene group having 6 to 12 ring carbon atoms that can be represented by L ²¹ , L ²² , and L ^{23 ,} a divalent group obtained by removing one hydrogen atom from the unsubstituted aryl group described for Raa and Rbb , except for those having 6 to 12 ring carbon atoms, is preferably an unsubstituted phenylene group, an unsubstituted naphthylene group, or an unsubstituted biphenylene group; more preferably, it is an unsubstituted phenylene group.

The unsubstituted phenylene group that L ²¹ , L ²² , and L ²³ can represent is an o-phenylene group, an m-phenylene group, or a p-phenylene group.

The unsubstituted naphthylene group which can be represented by L ²¹ , L ²² , and L ²³ is preferably a 1,4-naphthylene group or a 2,6-naphthylene group.

The unsubstituted biphenylene group which L ²¹ , L ²² , and L ²³ can represent is preferably a 4,4'-biphenylene group, a 4,3'-biphenylene group (same as "3,4'-biphenylene group"), or a 4,2'-biphenylene group (same as "2,4'-biphenylene group").

In formula (2), Ar ² is a group represented by formula (2a), (2b), (2c), (2d), (2e), or (2f).

[Chemical Formula 51]

In formula (2a), *61 is the binding position to L ²³ .

In formula (2a), Rdd and Rff are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;

However, Rdd and Rff may be combined with each other to form a ring structure, or may not be combined with each other to form a ring structure.

The details of the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms that can be represented by Rdd and Rff are the same as those described for the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms that can be represented by Raa and Rbb;

Accordingly, the types of alkyl groups, preferred alkyl groups, more preferred alkyl groups, more preferred alkyl groups, and more preferred alkyl groups, which are exemplified as the unsubstituted ring-forming alkyl groups having 1 to 30 carbon atoms that can be represented by Rdd and Rff, are also the same as those exemplified in the description of Raa and Rbb, respectively;

In addition, as a substituent that the unsubstituted alkyl group having 1 to 30 carbon atoms that can be represented by Rdd and Rff may have, for example, any of the substituents described below can be mentioned.

The details of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms that can be represented by Rdd and Rff are the same as those described for the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms that can be represented by Raa and Rbb;

Accordingly, the types of aryl groups, preferred aryl groups, more preferred aryl groups, more preferred aryl groups, and even more preferred aryl groups, which are exemplified as the unsubstituted aryl groups having 6 to 30 ring carbon atoms that can be represented by Rdd and Rff, are the same as those exemplified in the description of Raa and Rbb, respectively;

In addition, as a substituent that the unsubstituted ring-forming aryl group having 6 to 30 carbon atoms that can be represented by Rdd and Rff may have, examples thereof include any of the substituents described below, but among them, an alkyl group having 1 to 6 carbon atoms is preferable; more preferably, a methyl group or a t-butyl group.

The details of the substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms that can be represented by Rdd and Rff are the same as those described for the substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms that can be represented by the above Raa and Rbb;

Accordingly, the types of heterocyclic groups exemplified as the unsubstituted ring-forming heterocyclic groups having 5 to 30 ring atoms that can be represented by Rdd and Rff, and more preferable heterocyclic groups, are the same as those exemplified in the description of Raa and Rbb, respectively;

In addition, as a substituent that the heterocyclic group having 5 to 30 ring-forming atoms that can be represented by Rdd and Rff may have, for example, any of the substituents described below can be mentioned.

When Rdd and Rff combine with each other to form a ring structure, the details of the ring structure that Rdd and Rff can form by combining with each other are the same as those described with respect to the ring structure that Raa and Rbb can form by combining with each other;

Accordingly, specific examples of ring structures that can be formed by combining Rdd and Rff, and suitable ring structures thereof, are the same as those exemplified in the description of Raa and Rbb.

In one embodiment of the above-described compound (2), the group represented by the above formula (2a) is preferably represented by the following formula. However, in the following formula, the single bonds bonded to *61 and *62, which indicate bonding positions to L ²³ , and R ⁸¹ to R ⁸⁸ are omitted for simplicity.

However, when L ²³ is a single bond and Ar ² is represented by formula (2b), it is preferable that the group represented by formula (2a) is not unsubstituted spirobifluorene, and when L ²³ is a single bond, it is more preferable that the group represented by formula (2a) is not unsubstituted spirobifluorene.

[Chemical formula 52]

In formula (2a), R ⁸¹ to R ⁸⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.

However, one selected from R ⁸¹ to R ⁸⁸ is a single bond bonding to *62;

At least one group of two or more adjacent groups selected from R ⁸¹ to R ⁸⁸ , which are not single bonds bonded to the above *62, may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may not be bonded to each other to form a ring.

In one embodiment of the above-mentioned inventive compound (2), preferably, one selected from R ⁸² to R ⁸⁷ is a single bond bonding to *62, and more preferably, R ⁸² or R ⁸⁷ is a single bond bonding to *62.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R ⁸¹ to R ⁸⁸ are the same as those described for the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of alkyl groups, preferred alkyl groups, more preferred alkyl groups, more preferred alkyl groups, and still more preferred alkyl groups, which are exemplified as the unsubstituted alkyl groups having 1 to 10 carbon atoms that R ⁸¹ to R ⁸⁸ can represent, are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

The details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ⁸¹ to R ⁸⁸ are the same as those described for the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of cycloalkyl groups, preferred cycloalkyl groups, and more preferred cycloalkyl groups exemplified as the unsubstituted ring-forming cycloalkyl groups having 3 to 10 carbon atoms that can be represented by R ⁸¹ to R ⁸⁸ are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

The details of the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ⁸¹ to R ⁸⁸ are the same as those described for the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of aryl groups, preferred aryl groups, more preferred aryl groups, more preferred aryl groups, and even more preferred aryl groups, which are exemplified as the aryl groups having ⁶ to ¹⁸ unsubstituted ring-forming carbon atoms that can be represented by R 81 to R 88, are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

The details of the substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms that can be represented by R ⁸¹ to R ⁸⁸ are the same as those described for the substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of heterocyclic groups, preferred heterocyclic groups, and more preferred heterocyclic groups exemplified as the unsubstituted ring-forming heterocyclic groups having 5 to 13 ring atoms that can be represented by R ⁸¹ to R ⁸⁸ are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

[Chemical Formula 53]

In formula (2b), *70 is the binding position to L ²³ .

In formula (2b), one selected from R ²⁹¹ to ^{R 295} is a single bond bonding to *71, one selected from R ³⁰¹ to ^{R 305} is a single bond bonding to *72, and one selected from R ³⁰⁶ to R ³¹⁰ is a single bond bonding to *73;

R ²⁹¹ to R ²⁹⁵ , which are not single bonds bonding to the above *71, R ³⁰¹ to R ³⁰⁵ , which are not single bonds bonding to the above *72, and R ³⁰⁶ to ^{R 310} , which are not single bonds bonding to the above *73, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

Two adjacent groups selected from R ²⁹¹ to R ²⁹⁵ , which are not single bonds bonding to the above *71, do not bond to each other and therefore do not form a ring;

Two adjacent groups selected from R ³⁰¹ to R ³⁰⁵ , which are not single bonds bonding to the above *72, do not bond to each other and therefore do not form a ring;

Two adjacent groups selected from R ³⁰⁶ to R ³¹⁰ that are not single bonds bonded to the above *73 do not bond to each other and therefore do not form a ring.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R ²⁹¹ to ^{R 295} , R ³⁰¹ to R ³⁰⁵ and R ³⁰⁶ to R ³¹⁰ are the same as those described for the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of alkyl groups ^, preferred alkyl groups, more ^{preferred alkyl} groups, more preferred alkyl groups, and still ^more preferred alkyl groups, which are exemplified as the unsubstituted alkyl groups having 1 to ¹⁰ carbon atoms that can be represented by R ²⁹¹ to R 295, R 301 to R 305, and R 306 to R 310, are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

The details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ²⁹¹ to ^{R 295} , R ³⁰¹ to R ³⁰⁵ and R ³⁰⁶ to R ³¹⁰ are the same as those described for the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of cycloalkyl groups, preferred cycloalkyl groups, and more preferred cycloalkyl groups exemplified as the unsubstituted ring-forming cycloalkyl groups having 3 to ¹⁰ carbon atoms that can be represented by R ²⁹¹ to ^{R 295} , R ³⁰¹ to R ³⁰⁵ , and R 306 to R 310 are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

The details of the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ²⁹¹ to R ²⁹⁵ , R ³⁰¹ to R ³⁰⁵ and R ³⁰⁶ to R ³¹⁰ are the same as those described for the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types ^of aryl groups, preferred ^aryl groups, more ^preferred aryl groups, ^more preferred aryl groups, and even ^more preferred aryl groups, which are exemplified as the aryl groups having 6 to ¹⁸ unsubstituted ring-forming carbon atoms that can be represented by R 291 to R 295, R 301 to R 305, and R 306 to R 310, are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

In formula (2b), R ³¹¹ to R ³¹⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, two adjacent groups selected from R ³¹¹ to ^{R 315} do not bond to each other and therefore do not form a ring.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R ³¹¹ to R ³¹⁵ are the same as those described for the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of alkyl groups, preferred alkyl groups, more preferred alkyl groups, more preferred alkyl groups, and still more preferred alkyl groups, which are exemplified as the unsubstituted alkyl groups having 1 to 10 carbon atoms that R ³¹¹ to R ³¹⁵ can represent, are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

The details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ³¹¹ to R ³¹⁵ are the same as those described for the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of cycloalkyl groups, preferred cycloalkyl groups, and more preferred cycloalkyl groups exemplified as the unsubstituted ring-forming cycloalkyl groups having 3 to 10 carbon atoms that can be represented by R ³¹¹ to R ³¹⁵ are also the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ , respectively.

The details of the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ³¹¹ to R ³¹⁵ are the same as those described for the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of aryl groups, preferred aryl groups, more preferred aryl groups, more preferred aryl groups, and even more preferred aryl groups, which are exemplified as the aryl groups having ⁶ to ¹⁸ unsubstituted ring-forming carbon atoms that can be represented by R 311 to R 315, are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

In equation (2b), m is 0 or 1, n is 0 or 1, and p is 0 or 1;

step,

When m, n and p are 0, *73 indicates the binding position to L ²³ ,

When m and n are 0 and also p is 1, *72 indicates the binding position to L ²³ ,

When m is 0 and also n and p are 1, *71 indicates the binding position to L ²³ ,

When m and p are 0 and n is 1, *71 represents a bonding position to L ²³ , and one selected from R ³⁰¹ to R ³⁰⁵ is a single bond bonding to *73,

When m is 1 and also n and p are 0, one selected from R ²⁹¹ to R ²⁹⁵ is a single bond bonding to *73,

When m and n are 1 and p is 0, one selected from R ³⁰¹ to R ³⁰⁵ is a single bond binding to *73.

In one embodiment of the above-described compound (2), for example, the group represented by the above formula (2b) can represent each group represented by the following formula. However, in the following formula, R ²⁹¹ to R ²⁹⁵ , R ³⁰¹ to R ³⁰⁵ , R ³⁰⁶ to R ³¹⁰ and R ³¹¹ to R ³¹⁵ , which are not single bonds, are omitted for simplicity.

[Chemical Formula 54]

[Chemical formula 55]

In formula (2c), *74 is the binding position to L ²³ .

In formula (2c), R ³²¹ to R ³²⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, one selected from R ³²¹ to ^{R 328} is a single bond bonding to *75, and two adjacent selected from R ³²¹ to R ³²⁸ that are not single bonds bonding to *75 do not bond to each other and therefore do not form a ring.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R ³²¹ to R ³²⁸ are the same as those described for the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of alkyl groups, preferred alkyl groups, more preferred alkyl groups, more preferred alkyl groups, and even more preferred alkyl groups, which are exemplified as the unsubstituted alkyl groups having 1 to 10 carbon atoms that R ³²¹ to R ³²⁸ can represent, are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

The details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ³²¹ to R ³²⁸ are the same as those described for the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of cycloalkyl groups, preferred cycloalkyl groups, and more preferred cycloalkyl groups exemplified as the unsubstituted ring-forming cycloalkyl groups having 3 to 10 carbon atoms that can be represented by R ³²¹ to R ³²⁸ are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

The details of the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ³²¹ to R ³²⁸ are the same as those described for the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of aryl groups, preferred aryl groups, more preferred aryl groups, more preferred aryl groups, and even more preferred aryl groups, which are exemplified as the aryl groups having ⁶ to ¹⁸ unsubstituted ring-forming carbon atoms that can be represented by R 321 to R 328, are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

[Chemical formula 56]

In formula (2d), *76 is the binding position to L ²³ .

In formula (2d), R ³³¹ to R ³⁴⁰ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, one selected from R ³³¹ to ^{R 340} is a single bond bonding to *77, and two adjacent selected from R ³³¹ to R ³⁴⁰ that are not single bonds bonding to *77 do not bond to each other and therefore do not form a ring.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R ³³¹ to R ³⁴⁰ are the same as those described for the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of alkyl groups, preferred alkyl groups, more preferred alkyl groups, more preferred alkyl groups, and still more preferred alkyl groups, which are exemplified as the unsubstituted alkyl groups having 1 to 10 carbon atoms that R ³³¹ to R ³⁴⁰ can represent, are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

The details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ³³¹ to R ³⁴⁰ are the same as those described for the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of cycloalkyl groups, preferred cycloalkyl groups, and more preferred cycloalkyl groups exemplified as the unsubstituted ring-forming cycloalkyl groups having 3 to 10 carbon atoms that can be represented by R ³³¹ to R ³⁴⁰ are also the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ , respectively.

The details of the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ³³¹ to ^{R 340} are the same as those described for the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of aryl groups, preferred aryl groups, more preferred aryl groups, more preferred aryl groups, and even more preferred aryl groups, which are exemplified as the aryl groups having ⁶ to ¹⁸ unsubstituted ring-forming carbon atoms that can be represented by R 331 to R 340, are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

[Chemical formula 57]

In formula (2e), *78 is the binding position to L ²³ .

In formula (2e), R ³⁵¹ to R ³⁵⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, one selected from R ³⁵¹ to R ³⁵⁵ is a single bond binding to *79, and another selected from R ³⁵¹ to R ³⁵⁵ is a single bond binding to *80;

Two adjacent groups selected from R ³⁵¹ to R ³⁵⁵ , which are neither a single bond bonding to the above *79 nor a single bond bonding to the above *80, do not bond to each other and therefore do not form a ring.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R ³⁵¹ to R ³⁵⁵ are the same as those described for the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of alkyl groups, preferred alkyl groups, more preferred alkyl groups, more preferred alkyl groups, and still more preferred alkyl groups, which are exemplified as the unsubstituted alkyl groups having 1 to 10 carbon atoms that R ³⁵¹ to R ³⁵⁵ can represent, are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

The details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ³⁵¹ to R ³⁵⁵ are the same as those described for the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of cycloalkyl groups, preferred cycloalkyl groups, and more preferred cycloalkyl groups exemplified as the unsubstituted ring-forming cycloalkyl groups having 3 to 10 carbon atoms that can be represented by R ³⁵¹ to R ³⁵⁵ are also the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ , respectively.

The details of the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ³⁵¹ to R ³⁵⁵ are the same as those described for the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of aryl groups, preferred aryl groups, more preferred aryl groups, more preferred aryl groups, and even more preferred aryl groups, which are exemplified as the aryl groups having ⁶ to ¹⁸ unsubstituted ring-forming carbon atoms that can be represented by R 351 to R 355, are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

In formula (2e), R ³⁶¹ to ^{R 365} and R ³⁷¹ to R ³⁷⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, at least one group of two or more adjacent groups selected from R ³⁶¹ to R ³⁶⁵ may be combined with each other to form one or more substituted or unsubstituted benzene rings, or may not be combined with each other to form a ring;

At least one group of two or more adjacent groups selected from R ³⁷¹ to R ³⁷⁵ may be combined with each other to form one or more substituted or unsubstituted benzene rings, or may not be combined with each other to form a ring.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R ³⁶¹ to R ³⁶⁵ and R ³⁷¹ to R ³⁷⁵ are the same as those described for the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of alkyl ^groups , preferred alkyl groups, more preferred alkyl groups, more preferred alkyl groups, and still more preferred alkyl groups, which are exemplified as ^{the unsubstituted alkyl groups having 1 to 10 carbon atoms that can be represented by R 361 to R} 365 and R 371 to R 375, are the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ , respectively.

The details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ³⁶¹ to R ³⁶⁵ and R ³⁷¹ to R ³⁷⁵ are the same as those described for the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of cycloalkyl groups, preferred cycloalkyl groups, and more preferred cycloalkyl groups exemplified as the unsubstituted ring-forming cycloalkyl groups having 3 to 10 carbon atoms that can be represented by R ³⁶¹ to R ³⁶⁵ and R ³⁷¹ to R ³⁷⁵ are the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ , respectively.

The details of the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ³⁶¹ to R ³⁶⁵ and R ³⁷¹ to R ³⁷⁵ are the same as those described for the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of aryl groups, preferred aryl groups, more ^preferred aryl groups, more preferred aryl groups, and ^even more preferred aryl groups, which are exemplified as the aryl groups having 6 to ¹⁸ unsubstituted ring-forming carbon atoms ^that can be represented by R 361 to R 365 and R 371 to R 375, are the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ , respectively.

The group represented by the above formula (2e) includes groups represented by the following formulas (2e-1) to (2e-5).

[Chemical formula 58]

Among formulas (2e-1), (2e-2), (2e-3), (2e-4), and (2e-5), *78, R ³⁵¹ to ^{R 355} , R ³⁶¹ to ^{R 365} , and R ³⁷¹ to R ³⁷⁵ are defined as in the above formula (2e), and suitable embodiments thereof are also the same.

[Chemical formula 59]

In formula (2f), *81 is the binding position to L ²³ .

In formula (2f), R ³⁸¹ to R ³⁹² are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

However, one selected from R ³⁸¹ to ^{R 392} is a single bond bonding to *82, and two adjacent selected from R ³⁸¹ to R ³⁹² that are not single bonds bonding to *82 do not bond to each other and therefore do not form a ring.

The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by R ³⁸¹ to R ³⁹² are the same as those described for the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of alkyl groups, preferred alkyl groups, more preferred alkyl groups, more preferred alkyl groups, and still more preferred alkyl groups exemplified as the unsubstituted alkyl groups having 1 to 10 carbon atoms that can be represented by R ³⁸¹ to R ³⁹² are also the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ , respectively.

The details of the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by R ³⁸¹ to R ³⁹² are the same as those described for the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of cycloalkyl groups, preferred cycloalkyl groups, and more preferred cycloalkyl groups exemplified as the unsubstituted ring-forming cycloalkyl groups having 3 to 10 carbon atoms that can be represented by R ³⁸¹ to R ³⁹² are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

The details of the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by R ³⁸¹ to R ³⁹² are the same as those described for the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms that can be represented by the above R ⁵¹ to R ⁵⁸ ;

Accordingly, the types of aryl groups, preferred aryl groups, more preferred aryl groups, more preferred aryl groups, and even more preferred aryl groups, which are exemplified as the aryl groups having ⁶ to ¹⁸ unsubstituted ring-forming carbon atoms that can be represented by R 381 to R 392, are each the same as those exemplified in the description of R ⁵¹ to R ⁵⁸ .

However, in the above-described compound (2), when L ²¹ in formula (2) is a single bond and Ar ² is represented by formula (2b), the structure having a fluorene skeleton bonded to *51 is not an unsubstituted spirobifluorene.

In other words, when L ²¹ is a single bond, and Ar ² is represented by formula (2b), and all of R ⁵¹ to R ⁵⁸ that are not single bonds bonded to the above *51 are hydrogen atoms, Raa and Rbb are mutually unsubstituted phenyl groups, and further, the two unsubstituted phenyl groups do not bond to each other to form the ring structure below. Meanwhile, * in the ring structure shown below indicates the bonding position of the fluorene skeleton to the benzene ring.

[Chemical formula 60]

In addition, in one embodiment of the present invention, in the compound (2) of the invention, when L ²¹ is represented by a single bond in formula (2), it is preferable that the structure having a fluorene skeleton bonded to *51 is not an unsubstituted spirobifluorene.

In addition, in one embodiment of the present invention, when L ²¹ is an unsubstituted arylene group having 6 to 12 ring carbon atoms, and further, Ar ² is represented by formula (2b), and further, all of R ⁵¹ to R ⁵⁸ that are not single bonds bonded to *51 are hydrogen atoms, there is no particular limitation on the ring structure that Raa and Rbb may form by bonding to each other, but it is preferable that Raa and Rbb are unsubstituted phenyl groups, and further, the two unsubstituted phenyl groups do not form the ring structure by bonding to each other.

In addition, in one embodiment of the present invention, when L ²¹ is an unsubstituted arylene group having 6 to 12 ring carbon atoms, and all of R ⁵¹ to R ⁵⁸ that are not single bonds bonded to *51 are hydrogen atoms, there is no particular limitation on the ring structure that Raa and Rbb may form by bonding to each other, but it is more preferable that Raa and Rbb are unsubstituted phenyl groups, and furthermore, the two unsubstituted phenyl groups do not bond to each other to form the ring structure.

The above-described inventive compound (2) satisfies at least one requirement selected from the following requirements (I) and (II) in formula (2);

Requirement (I): R ⁶¹ to R ⁶⁸ , and at least one selected from R ⁷¹ to R ⁷⁵ that is not a single bond bonding to the above *52 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms;

Requirement (II): Rcc is an aryl group having 6 to 30 ring carbon atoms having at least one substituent selected from an alkyl group having 1 to 10 ring carbon atoms and a cycloalkyl group having 3 to 10 ring carbon atoms.

In one embodiment of the above invention compound (2), in formula (2),

(2-1) All of R ⁵¹ to R ⁵⁸ , which are not single bonds bonded to *51, may be hydrogen atoms;

(2-2) All of R ⁶¹ to R ⁶⁸ may be hydrogen atoms;

(2-3) All of R ⁷¹ to R ⁷⁵ , which are not single bonds bonded to *52, may be hydrogen atoms;

(2-4) *All of R ⁸¹ to R ^88, which are not single bonds bonded to 62, may be hydrogen atoms;

(2-5) *All of R ²⁹¹ to R ^295, which are not single bonds bonded to 71, may be hydrogen atoms;

(2-6) *All of R ³⁰¹ to R ^305, which are not single bonds bonded to 72, may be hydrogen atoms;

(2-7) *All of R ³⁰⁶ to R ^310, which are not single bonds bonding to 73, may be hydrogen atoms;

(2-8) All of R ³¹¹ to ^{R 315} may be hydrogen atoms;

(2-9) *All of R ³²¹ to R ^328, which are not single bonds bonding to 75, may be hydrogen atoms;

(2-10) *All of R ³³¹ to R ^340, which are not single bonds bonding to 77, may be hydrogen atoms;

(2-11) *It is not a single bond bonding to *79, nor is it a single bond bonding to *80, but all of R ³⁵¹ to R ³⁵⁵ can be hydrogen atoms;

(2-12) All of R ³⁶¹ to R ³⁶⁵ may be hydrogen atoms;

(2-13) All of R ³⁷¹ to R ³⁷⁵ may be hydrogen atoms;

(2-14) *All of R ³⁸¹ to R ³⁹² that are not single bonds bonding to 82 may be hydrogen atoms.

In one embodiment of the above-described compound (2), it is preferable that in formula (2), all of R ⁵¹ to R ⁵⁸ that are not single bonds bonded to *51, R ⁶¹ to R ⁶⁸ that are not substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, or substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, and R ⁷¹ to R ⁷⁵ that are not substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, or substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, and further that are not single bonds bonded to *52, are hydrogen atoms.

In one embodiment of the above-mentioned invention compound (2), in formula (2), at least one selected from R ⁶¹ to R ⁶⁸ is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms,

It is more preferable that all of R ⁶¹ to ^{R 66} , which are not the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms and also not the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, R ⁷¹ to R ⁷⁵ , which are not single bonds bonded to *52, and R ⁵¹ to R ⁵⁸ , which are not single bonds bonded to *51, are hydrogen atoms.

In one embodiment of the above-described compound (2), in formula (2), it is preferable that Raa and Rbb are each independently an unsubstituted aryl group having 6 to 12 ring carbon atoms; it is more preferable that both Raa and Rbb are unsubstituted aryl groups having 6 to 12 ring carbon atoms; it is even more preferable that both Raa and Rbb are unsubstituted phenyl groups.

In one embodiment of the above-described compound (2), in formula (2), it is preferable that Rcc is an unsubstituted aryl group having 6 to 12 ring carbon atoms, and more preferably an unsubstituted phenyl group.

In one embodiment of the above-described compound (2), it is preferable that Raa, Rbb and Rcc in formula (2) are each independently a substituted or unsubstituted phenyl group; it is more preferable that Raa, Rbb and Rcc are all substituted or unsubstituted phenyl groups; it is even more preferable that Raa, Rbb and Rcc are all unsubstituted phenyl groups.

In one embodiment of the above-described compound (2), in formula (2), it is preferable that L ²¹ and L ²² are each independently a single bond or an unsubstituted phenylene group; it is more preferable that both of L ²¹ and L ²² are single bonds or unsubstituted phenylene groups; and it is even more preferable that both of L ²¹ and L ²² are single bonds.

In one embodiment of the above-described compound (2), in formula (2), it is preferable that L ²³ is a single bond or an unsubstituted phenylene group; and it is more preferable that L ²³ is a single bond.

In one embodiment of the above-described compound (2), it is more preferable that all of L ²¹ , L ²² and L ²³ in formula (2) are single bonds or unsubstituted phenylene groups; it is even more preferable that all of L ²¹ , L ²² and L ²³ are single bonds.

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

In one embodiment of the above-described compound (2), it is preferable that in formula (2), Ar ² is a group represented by formula (2a), and further, in formula (2a), one selected from R ⁸² to R ⁸⁷ is a single bond bonding to *62; it is more preferable that Ar ² is a group represented by formula (2a), and further, in formula (2a), R ⁸² or R ⁸⁷ is a single bond bonding to *62.

In one embodiment of the above invention compound (2), in formula (2), L ²³ is a single bond, Ar ² is a group represented by formula (2b), and further, in formula (2b), m, n and p are 0, or

L ²³ is a single bond, Ar ² is a group represented by the above formula (2b), and further, in the above formula (2b), m is 1, further, n and p are 0, and R ²⁹¹ or R ²⁹⁵ is a single bond bonded to *73, or

L ²³ is a single bond, Ar ² is a group represented by the above formula (2b), and further, in the above formula (2b), n is 1, further, m and p are 0, and R ³⁰¹ or R ³⁰⁵ is a single bond bonding to *73, or

It is preferable that L ²³ is a single bond, Ar ² is a group represented by the above formula (2b), and furthermore, in the above formula (2b), m and n are 0, furthermore, p is 1, and R ³⁰⁶ or R ³¹⁰ is a single bond bonding to *73.

In addition, in one embodiment of the above-described compound (2), one or more kinds selected from the requirements of each suitable embodiment described above can be appropriately combined.

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

In addition, a deuterium atom may be intentionally introduced into the invention compound (2) by using a compound in which part or all of the raw material compound is deuterated. Therefore, in one embodiment of the present invention, the invention compound (2) contains at least one deuterium atom. That is, the invention compound (2) may be a compound represented by formula (2), and may be a compound in which at least one of the hydrogen atoms contained in the compound is a deuterium atom.

At least one hydrogen atom selected from the hydrogen atoms below may be a deuterium atom. In the following, "substituted or unsubstituted", the number of carbon atoms and the number of atoms are omitted for simplicity. One hydrogen atom of the substituent according to the above "substituted or unsubstituted", or at least one hydrogen atom selected from two or more hydrogen atoms may also be the above deuterium atom.

A hydrogen atom possessed by an alkyl group, an aryl group, or a heterocyclic group that can be represented by Raa in formula (2);

A hydrogen atom possessed by an alkyl group, an aryl group, or a heterocyclic group that can be represented by Rbb in formula (2);

A hydrogen atom having a ring structure that Raa and Rbb of formula (2) can form by combining with each other;

A hydrogen atom that can be represented by any of R ⁵¹ to R ⁵⁸ , but not a single bond bonding to *51 in formula (2);

A hydrogen atom possessed by an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group that can be represented by any of R ⁵¹ to R ⁵⁸ , but not a single bond bonded to *51 in formula (2);

A hydrogen atom of one or more benzene rings which can be formed by combining with each other one or more groups of two or more adjacent groups selected from R ⁵¹ to R ⁵⁸ , which are not single bonds bonding to *51 of formula (2);

A hydrogen atom of an alkyl group or an aryl group that can be represented by Rcc in formula (2);

A hydrogen atom that can be represented by any of R ⁶¹ to R ⁶⁸ in formula (2);

A hydrogen atom possessed by an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group which can be represented by any of R ⁶¹ to R ⁶⁸ in formula (2);

A hydrogen atom possessed by one or more benzene rings which can be formed by combining with each other at least one group of two or more adjacent groups selected from R ⁶¹ to R ⁶⁸ of formula (2);

A hydrogen atom that can be represented by any of R ⁷¹ to ^{R 75,} but not a single bond bonding to *52 in formula (2);

A hydrogen atom possessed by an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group that can be represented by any of R ⁷¹ to R ⁷⁵ , but not a single bond bonded to *52 in formula (2);

A hydrogen atom of one or more benzene rings which can be formed by combining with each other one or more groups of two or more adjacent groups selected from R ⁷¹ to R ⁷⁵ , which are not single bonds bonding to *52 of formula (2);

Hydrogen atom of the arylene group that can be represented by L ²¹ in formula (2);

Hydrogen atom of an arylene group that can be represented by L ²² in formula (2);

Hydrogen atom of the arylene group that can be represented by L ²³ in formula (2);

A hydrogen atom possessed by an alkyl group, an aryl group, or a heterocyclic group that can be represented by Rdd of formula (2a);

A hydrogen atom possessed by an alkyl group, an aryl group, or a heterocyclic group that can be represented by Rff of formula (2a);

A hydrogen atom having a ring structure that can be formed by combining Rdd and Rff of formula (2a);

A hydrogen atom that can be represented by any of R ⁸¹ to R ⁸⁸ , but not a single bond bonding to *62 in formula (2a);

A hydrogen atom possessed by an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group that may be represented by any of R ⁸¹ to R ⁸⁸ , but which is not a single bond bonded to *62 of formula (2a);

A hydrogen atom of one or more benzene rings which can be formed by combining with each other one or more groups of two or more adjacent groups selected from R ⁸¹ to R ⁸⁸ , which are not single bonds bonding to *62 of formula (2a);

A hydrogen atom which can be represented by any of R ²⁹¹ to ^{R 295} , but not a single bond bonding to *71 in formula (2b);

A hydrogen atom of an alkyl group, a cycloalkyl group, or an aryl group that can be represented by any of R ²⁹¹ to R ²⁹⁵ , but not a single bond bonding to *71 of formula (2b);

A hydrogen atom which can be represented by any of R ³⁰¹ to R ³⁰⁵ , but not a single bond bonding to *72 of formula (2b);

A hydrogen atom of an alkyl group, a cycloalkyl group, or an aryl group which may be represented by any of R ³⁰¹ to R ³⁰⁵ , but which is not a single bond bonded to *72 of formula (2b);

A hydrogen atom which can be represented by any of R ³⁰⁶ to R ³¹⁰ , but not a single bond bonding to *73 in formula (2b);

A hydrogen atom of an alkyl group, a cycloalkyl group, or an aryl group which is not a single bond bonded to *73 of formula (2b) and which can be represented by any of R ³⁰⁶ to R ³¹⁰ ;

A hydrogen atom which can be represented by any of R ³¹¹ to R ³¹⁵ in formula (2b);

A hydrogen atom of an alkyl group, a cycloalkyl group, or an aryl group which can be represented by any of R ³¹¹ to R ³¹⁵ of formula (2b);

A hydrogen atom which can be represented by any of R ³²¹ to R ³²⁸ , but not a single bond bonding to *75 in formula (2c);

A hydrogen atom of an alkyl group, a cycloalkyl group, or an aryl group that can be represented by any of R ³²¹ to R ³²⁸ , but not a single bond bonding to *75 in formula (2c);

A hydrogen atom which can be represented by any of R ³³¹ to ^{R 340} , but not a single bond bonding to *77 of formula (2d);

A hydrogen atom of an alkyl group, a cycloalkyl group, or an aryl group which is not a single bond bonded to *77 of formula (2d) and which can be represented by any of R ³³¹ to R ³⁴⁰ ;

A hydrogen atom that can be represented by any of R ³⁵¹ to R ³⁵⁵ , which is neither a single bond bonded to *79 of formula (2e) nor a single bond bonded to *80;

A hydrogen atom of an alkyl group, a cycloalkyl group, or an aryl group that is not a single bond bonded to *79 of formula (2e) nor a single bond bonded to *80 and can be represented by any of R ³⁵¹ to ^{R 355} ;

A hydrogen atom which can be represented by any of R ³⁶¹ to R ³⁶⁵ in formula (2e);

A hydrogen atom of an alkyl group, a cycloalkyl group, or an aryl group which can be represented by any of R ³⁶¹ to R ³⁶⁵ of formula (2e);

A hydrogen atom possessed by one or more benzene rings which can be formed by combining with each other at least one group of two or more adjacent groups selected from R ³⁶¹ to R ³⁶⁵ of formula (2e);

A hydrogen atom which can be represented by any of R ³⁷¹ to R ³⁷⁵ in formula (2e);

A hydrogen atom of an alkyl group, a cycloalkyl group, or an aryl group which can be represented by any of R ³⁷¹ to R ³⁷⁵ of formula (2e);

A hydrogen atom of one or more benzene rings which can be formed by combining with each other at least one group of two or more adjacent groups selected from R ³⁷¹ to R ³⁷⁵ of formula (2e);

A hydrogen atom which can be represented by any of R ³⁸¹ to ^{R 392} , but not a single bond bonding to *82 of formula (2f);

A hydrogen atom possessed by an alkyl group, cycloalkyl group, or aryl group that can be represented by any of R ³⁸¹ to R ³⁹² , but not a single bond bonding to *82 of formula (2f).

The deuteration rate of the inventive compound depends on the deuteration rate of the raw material compound used. Even if a raw material with a predetermined deuteration rate is used, a certain ratio of naturally occurring hydrogen isotopes may be included. Therefore, the aspect of the deuteration rate of the inventive compound shown below includes a ratio that takes into account a trace amount of naturally occurring isotopes, relative to the ratio obtained by simply counting the number of deuterium atoms represented by the chemical formula.

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

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

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

When the "substituted or unsubstituted XX group" included in the definition of each of the above formulas is a substituted XX group, the details of the substituent (any substituent) are as described in "Substituent in the case of "substituted or unsubstituted"" for those not specifically mentioned in the above explanation, and is preferably an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 ring carbon atoms, an aryl group having 6 to 18 ring carbon atoms, or a heterocyclic group having 5 to 13 ring atoms, more preferably an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 ring carbon atoms, or an aryl group having 6 to 18 ring carbon atoms, and even more preferably an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 18 ring carbon atoms. The details of each group are as described above.

Suitable examples of the optional substituent include, for example, the alkyl group having 1 to 10 carbon atoms, preferably a methyl group or a t-butyl group. For example, the aryl group having 6 to 18 ring-forming carbon atoms is preferably a phenyl group.

The invention compound can be easily prepared by those skilled in the art by referring to the following synthetic examples and known synthetic methods.

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

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

[Chemical formula 61]

[Chemical formula 62]

[Chemical formula 63]

[Chemical formula 64]

[Chemical formula 65]

[Chemical formula 66]

[Chemical formula 67]

[Chemical formula 68]

[Chemical formula 69]

[Chemical formula 70]

[Chemical formula 71]

[Chemical formula 72]

[Chemical formula 73]

[Chemical formula 74]

[Chemical formula 75]

[Chemical formula 76]

[Chemical formula 77]

[Chemical formula 78]

[Chemical formula 79]

[Chemical formula 80]

[Chemical formula 81]

[Chemical formula 82]

[Chemical formula 83]

[Chemical formula 84]

[Chemical formula 85]

[Chemical formula 86]

[Chemical formula 87]

[Chemical formula 88]

[Chemical formula 89]

[Chemical formula 90]

[Chemical formula 91]

[Chemical formula 92]

[Chemical formula 93]

[Chemical formula 94]

[Chemical formula 95]

[Chemical formula 96]

[Chemical formula 97]

[Chemical formula 98]

[Chemical formula 99]

[Chemical Formula 100]

[Chemical Formula 101]

[Chemical Formula 102]

[Chemical Formula 103]

[Chemical Formula 104]

[Chemical Formula 105]

[Chemical formula 106]

[Chemical Formula 107]

[Chemical Formula 108]

[Chemical Formula 109]

[Chemical formula 110]

[Chemical formula 111]

[Chemical formula 112]

[Chemical formula 113]

[Chemical Formula 114]

[Chemical formula 115]

[Chemical formula 116]

[Chemical formula 117]

[Chemical formula 118]

[Chemical Formula 119]

[Chemical formula 120]

[Chemical Formula 121]

[Chemical formula 122]

[Chemical formula 123]

[Chemical Formula 124]

[Chemical formula 125]

[Chemical formula 126]

[Chemical formula 127]

[Chemical formula 128]

[Chemical Formula 129]

[Chemical formula 130]

[Chemical Formula 131]

[Chemical formula 132]

[Chemical formula 133]

[Chemical Formula 134]

[Chemical formula 135]

[Chemical formula 136]

[Chemical formula 137]

[Chemical formula 138]

[Chemical Formula 139]

[Chemical formula 140]

[Chemical Formula 141]

[Chemical formula 142]

[Chemical formula 143]

[Chemical Formula 144]

[Chemical formula 145]

[Chemical formula 146]

[Chemical formula 147]

[Chemical formula 148]

[Chemical formula 149]

[Chemical formula 150]

[Chemical Formula 151]

[Chemical formula 152]

[Chemical formula 153]

[Chemical Formula 154]

[Chemical Formula 155]

[Chemical formula 156]

[Chemical formula 157]

[Chemical formula 158]

[Chemical Formula 159]

[Chemical formula 160]

[Chemical Formula 161]

[Chemical formula 162]

[Chemical formula 163]

[Chemical formula 164]

[Chemical formula 165]

[Chemical formula 166]

[Chemical formula 167]

[Chemical formula 168]

[Chemical Formula 169]

[Chemical formula 170]

[Chemical Formula 171]

Materials for organic EL devices

An organic EL device material according to one embodiment of the present invention contains the invention compound. The content of the invention compound in the organic EL device material is 1 mass% or more (including 100 mass%), preferably 10 mass% or more (including 100 mass%), more preferably 50 mass% or more (including 100 mass%), more preferably 80 mass% or more (including 100 mass%), and particularly preferably 90 mass% or more (including 100 mass%). In other words, in one embodiment of the present invention, the content of the invention compound in the organic EL device material is 1 to 100 mass%, preferably 10 to 100 mass%, more preferably 50 to 100 mass%, more preferably 80 to 100 mass%, and particularly preferably 90 to 100 mass%.

A material for an organic EL device, which is one aspect of the present invention, is useful for manufacturing an organic EL device.

In one aspect of the present invention, it is preferable that the material for the organic EL device is a hole transport layer material.

Organic EL devices

An organic EL device according to one aspect of the present invention comprises an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer comprises a light-emitting layer, and at least one layer of the organic layer comprises the invention compound.

Examples of organic layers including the inventive compound include, but are not limited to, a hole transport band (a hole injection layer, a hole transport layer, an electron blocking layer, an exciton blocking layer, etc.) provided between the anode and the light-emitting layer, a light-emitting layer, a space layer, an electron transport band (an electron injection layer, an electron transport layer, a hole blocking layer, etc.) provided between the cathode and the light-emitting layer, and the like. The inventive compound is preferably used as a material for a hole transport band or a light-emitting layer of a fluorescent or phosphorescent EL device, more preferably as a material for a hole transport band, more preferably as a material for a hole injection layer, a hole transport layer, an electron blocking layer, or an exciton blocking layer, and particularly preferably as a material for a hole injection layer or a hole transport layer.

The organic EL device of the present invention may be a single-color light-emitting device of a fluorescent or phosphorescent type, a white light-emitting device of a fluorescent/phosphorescent hybrid type, a simple type having a single light-emitting unit, or a tandem type having a plurality of light-emitting units, and among these, a fluorescent light-emitting device is preferable. Here, the "light-emitting unit" means the smallest unit that includes an organic layer, at least one of which is a light-emitting layer, and that emits light by the recombination of injected holes and electrons.

For example, as a representative device configuration of a simple organic EL device, the following device configuration can be mentioned.

(1) Anode/Light-emitting unit/Cathode

In addition, the above-mentioned light-emitting unit may be a multilayer type having multiple phosphorescent light-emitting layers or fluorescent light-emitting layers, and in that case, a space layer may be provided between each light-emitting layer for the purpose of preventing excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer. A typical layer configuration of a simple type light-emitting unit is shown below. The layers in parentheses are arbitrary.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Each of the above phosphorescent or fluorescent emitting layers can exhibit different emission colors. Specifically, in the above emitting unit (d), a layer configuration such as (hole injection layer/) hole transport layer/first phosphorescent emitting layer (red emission)/second phosphorescent emitting layer (green emission)/space layer/fluorescent emitting layer (blue emission)/electron transport layer can be exemplified.

Meanwhile, an electron blocking layer may be provided appropriately between each light-emitting layer and the hole transport layer or space layer. In addition, a hole blocking layer may be provided appropriately between each light-emitting layer and the electron transport layer. By providing an electron blocking layer or a hole blocking layer, electrons or holes can be confined within the light-emitting layer, thereby increasing the probability of charge recombination in the light-emitting layer, and improving the light-emitting efficiency.

In addition, when the hole transport layer is a multilayer structure including two or more hole transport layers, the hole transport layer adjacent to the emitting layer in the multilayer structure, for example, the second hole transport layer of the two-layer structure or the third hole transport layer of the three-layer structure, may function as an electron blocking layer. That is, when the hole transport layer is a multilayer structure including two or more hole transport layers, the hole transport layer adjacent to the emitting layer in the multilayer structure may also be used as an electron blocking layer.

As representative device configurations of tandem-type organic EL devices, the following device configurations can be cited.

(2) Anode/First light emitting unit/Intermediate layer/Second light emitting unit/Cathode

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

The above intermediate layer is generally also called an intermediate electrode, an intermediate conductive layer, a charge generating layer, an electron extracting layer, a connection layer, or an intermediate insulating layer, and can utilize a known material composition that supplies electrons to the first light-emitting unit and holes to the second light-emitting unit.

Fig. 1 is a schematic diagram showing an example of the configuration of an organic EL device of the present invention. The organic EL device (1) has a substrate (2), an anode (3), a cathode (4), and a light-emitting unit (10) arranged between the anode (3) and the cathode (4). The light-emitting unit (10) has a light-emitting layer (5). A hole transport band (6) (a hole injection layer, a hole transport layer, etc.) is provided between the light-emitting layer (5) and the anode (3), and an electron transport band (7) (an electron injection layer, an 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). As a result, electrons and holes can be confined in the light-emitting layer (5), and the generation efficiency of excitons in the light-emitting layer (5) can be further increased.

FIG. 2 is a schematic diagram showing another configuration of an organic EL device of the present invention. An organic EL device (11) has a substrate (2), an anode (3), a cathode (4), and a light-emitting unit (20) disposed between the anode (3) and the cathode (4). The light-emitting unit (20) has a light-emitting layer (5). A hole transport band disposed between the anode (3) and the light-emitting layer (5) is formed by a hole injection layer (6a), a first hole transport layer (6b), and a second hole transport layer (6c). In addition, an electron transport band disposed between the light-emitting layer (5) and the cathode (4) is formed by a first electron transport layer (7a) and a second electron transport layer (7b).

FIG. 3 is a schematic diagram showing another configuration of an organic EL element of the present invention. An organic EL element (12) has 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). A hole transport band disposed between the anode (3) and the light-emitting layer (5) is formed by a hole injection layer (6a), a first hole transport layer (6b), a second hole transport layer (6c), and a third hole transport layer (6d). In addition, an electron transport band disposed between the light-emitting layer (5) and the cathode (4) is formed by a first electron transport layer (7a) and a second electron transport layer (7b).

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

Substrate

The substrate is used as a support for the organic EL element. As the substrate, for example, a plate of glass, quartz, plastic, etc. can be used. In addition, a flexible substrate may be used. As the flexible substrate, for example, a plastic substrate made of polyimide, polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, etc. can be mentioned. In addition, an inorganic deposition film can also be used.

anode

For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a large work function (specifically, 4.0 eV or more). Specific examples thereof include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, graphene, etc. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the above metals (for example, titanium nitride), etc.

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

Positive transport band

As described above, the organic layer may include a hole transport zone between the anode and the light-emitting layer. The hole transport zone is composed of a hole injection layer, a hole transport layer, an electron blocking layer, etc. It is preferable that the hole transport zone includes the invention compound. It is preferable that at least one of these layers constituting the hole transport layer includes the invention compound, and it is more preferable that the hole transport layer includes the invention compound.

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

It is also possible to use elements belonging to Group 1 or 2 of the Periodic Table of Elements, which are materials with a small work function, namely, alkali metals such as lithium (Li) or cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing them. Meanwhile, when forming an anode using an alkali metal, an alkaline earth metal, or an alloy containing them, a vacuum deposition method or a sputtering method can be used. In addition, when using silver paste or the like, a coating method or an inkjet method can be used.

Hole injection layer

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

As hole-injecting materials 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, and the like can be used.

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

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

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

[Chemical formula 172]

(In the above formula, R ²²¹ to R ²²⁶ each independently represent a cyano group, -CONH ₂ , a carboxyl group, or -COOR ²²⁷ (R ²²⁷ represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms). In addition, two adjacent groups selected from R ²²¹ and R ²²² , R ²²³ 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 a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclopentyl group, and a cyclohexyl group.

hole transport layer

The hole transport layer is a layer containing a material with high hole transport properties (hole transport material), and is formed between the anode and the light-emitting layer, or, if present, between the hole injection layer and the light-emitting layer. The inventive compound may be used alone or in combination with the following compounds in the hole transport layer.

The hole transport layer may have a single-layer structure or a multilayer structure including two or more layers. For example, the hole transport layer may have a two-layer structure including a first hole transport layer (anode side) and a second hole transport layer (cathode side). That is, the hole transport band may include a first hole transport layer on the anode side and a second hole transport layer on the cathode side. In addition, the hole transport layer may have a three-layer structure including a first hole transport layer, a second hole transport layer, and a third hole transport layer in order from the anode side. That is, the third hole transport layer may be arranged between the second 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 furthermore, the hole transport layer closest to the cathode in the multilayer structure, for example, the second hole transport layer of the two-layer structure or the third hole transport layer of the three-layer structure, is preferably adjacent to the light-emitting layer. In another embodiment of the present invention, an electron blocking layer, etc. described later, may be interposed between the hole transport layer of the single-layer structure and the light-emitting layer, or between the hole transport layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer. Furthermore, as described above, when the hole transport layer is a multilayer structure including two or more hole transport layers, the hole transport layer adjacent to the light-emitting layer in the multilayer structure can also be used as an electron blocking layer.

In one embodiment of the present invention, when the hole transport layer has a two-layer structure, as described above, it is preferable that the second hole transport layer is adjacent to the light-emitting layer. That is, when the organic layer includes a hole transport band between the anode and the light-emitting layer, and the hole transport band has a two-layer structure including a first hole transport layer on the anode side and a second hole transport layer on the cathode side, it is preferable that the light-emitting layer and the second hole transport layer are in direct contact.

In one embodiment of the present invention, when the hole transport layer has a two-layer structure, it is preferable that at least one of the first hole transport layer and the second hole transport layer contains the inventive compound. That is, it is preferable that the inventive compound is contained only in the first hole transport layer, only in the second hole transport layer, or in both the first hole transport layer and the second hole transport layer.

In one embodiment of the present invention, it is more preferable that the inventive compound is included in the second hole transport layer. That is, it is more preferable that the inventive compound is included only in the second hole transport layer, or that the inventive compound is included in both the first hole transport layer and the second hole transport layer.

In one embodiment of the present invention, when the hole transport layer has a three-layer structure, as described above, it is preferable that the third hole transport layer is adjacent to the light-emitting layer. That is, when the organic layer includes a hole transport band between the anode and the light-emitting layer, and the hole transport band has a three-layer structure including a first hole transport layer, a second hole transport layer, and a third hole transport layer in order from the anode side, it is preferable that the light-emitting layer and the third hole transport layer are in direct contact.

In one embodiment of the present invention, when the hole transport layer has a three-layer structure, it is preferable that at least one of the first to third hole transport layers contains the inventive compound. That is, the inventive compound is preferably included in only one layer selected from the first to third hole transport layers (only the first hole transport layer, only the second hole transport layer, or only the third hole transport layer), in only two layers selected from the first to third hole transport layers (only the first hole transport layer and the second hole transport layer, only the first hole transport layer and the third hole transport layer, or only the second hole transport layer and the third hole transport layer), or in all layers of the first to third hole transport layers.

In one embodiment of the present invention, it is more preferable that the inventive compound is included in the third hole transport layer. That is, it is more preferable that the inventive compound is included only in the third hole transport layer, or that the inventive compound is included in one or both of the third hole transport layer and the first hole transport layer and the second hole transport layer.

In one embodiment of the present invention, the inventive compound included in each of the above hole transport layers is preferably a light hydrogen body from the viewpoint of manufacturing cost. The light hydrogen body is an inventive compound in which all hydrogen atoms in the inventive compound are light hydrogen atoms.

Therefore, in one embodiment of the present invention, it is preferable to include an organic EL device including an inventive compound in which one or both of the first hole transport layer and the second hole transport layer (in the case of a two-layer structure) and at least one of the first to third hole transport layers substantially consist only of a hydrogenophore. The "inventive compound substantially consisting only of a hydrogenophore" means that the content of the hydrogenophore with respect to the total amount of the inventive compound is 90 mol% or more, preferably 95 mol% or more, more preferably 99 mol% or more (each including 100 mol%). In other words, in one embodiment of the present invention, the "inventive compound substantially consisting only of a hydrogenophore" means that the content of the hydrogenophore with respect to the total amount of the inventive compound is 90 to 100 mol%, preferably 95 to 100 mol%, more preferably 99 to 100 mol%.

As hole transport layer materials other than the inventive compound, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used.

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

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

Examples of anthracene derivatives include 2-t-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and 9,10-diphenylanthracene (abbreviation: DPAnth).

Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) or poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.

However, compounds other than those mentioned above may be used if they have a higher hole transport property than an electron transport property.

In the organic EL device having a two-layer hole transport layer structure of the present invention, it is preferable that the first hole transport layer contains one or more compounds represented by the following formula (11) or formula (12).

In the organic EL device having a three-layer hole transport layer structure of the present invention, it is preferable that one or both of the first hole transport layer and the second hole transport layer include one or more compounds represented by the following formula (11) or (12).

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

[Chemical formula 173]

[Among the above equations (11) and (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 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

k is 1, 2, 3 or 4,

When k is 1, L ^E2 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

When k is 2, 3 or 4, 2, 3 or 4 L ^E2 are equal to or different from each other,

When k is 2, 3 or 4, plural L ^E2 may be combined with each other to form a substituted or unsubstituted monocyclic ring, or may be combined with each other to form a substituted or unsubstituted condensed ring, or may not be combined with each other,

L ^E2 , which does not form the above-mentioned monocyclic ring and also does not form the above-mentioned 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 atoms,

A ¹ , B ¹ , C ¹ , A ² , B ² , C ² , and D ² are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring 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 carbon atoms,

In case there are multiple R' _901s , the multiple R' _901s are identical to each other or different,

When there are multiple R' _902s , the multiple R' _902s are identical or different from each other,

When there are multiple R' _903s , the multiple R' _903s are the same or different from each other.]

In formulas (11) and (12), A ¹ , B ¹ , C ¹ , A ² , B ² , C ² , and D ² are preferably, each independently, selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.

In addition, more preferably, in formula (11), at least one of A ¹ , B ¹ , and C ¹ , and in formula (12), at least one of A ² , B ² , C ² , and D ² 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 that A ¹ , B ¹ , C ¹ , A ² , B ² , C ² , and D ² can have a substituent at position 9, and may be, for example, a 9,9-dimethylfluorenyl group or a 9,9-diphenylfluorenyl group. In addition, the substituents at position 9 may form a ring, and for example, the substituents at position 9 may form a fluorene skeleton or a xanthene skeleton.

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 carbon atoms.

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

[Chemical Formula 174]

Dopant material of the light-emitting layer

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

In one embodiment of the organic EL device according to the present invention, it is preferable that the light-emitting layer is a single layer.

In addition, in another embodiment of the organic EL device according to the present invention, it is preferable that the light-emitting layer includes a first light-emitting layer and a second light-emitting layer.

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

As a green fluorescent emitting material that can be used in the emitting layer, an aromatic amine derivative, etc. can be used. Specifically, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), Examples include N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), etc.

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

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

As a green phosphorescent emitting material that can be used in the emitting layer, iridium complexes, etc. are used. Examples thereof include tris(2-phenylpyridinato-N,C2')iridium(III) (abbreviation: Ir(ppy)3), bis(2-phenylpyridinato-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazolato)iridium(III) acetylacetonate (abbreviation: Ir(pbi)2(acac)), and bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)).

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

In addition, rare earth metal complexes such as tris(acetylacetonate)(monophenanthroline)terbium(III) (abbreviation: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: Eu(DBM)3(Phen)), and tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: Eu(TTA)3(Phen)) can be utilized as phosphorescent emitting materials because the emission is from rare earth metal ions (electron transitions between different multiplicities).

Host material of the luminescent layer

The light-emitting layer may be configured by dispersing the above-described dopant material in another material (host material). It is preferable to use a material that has a lower lowest unoccupied orbital level (LUMO level) and a lower highest occupied orbital level (HOMO level) than the dopant material.

As a host material, for example,

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

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

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

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

For example, metal complexes such as tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ);

Heterocyclic compounds such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), and bathocuproine (abbreviation: 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-di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,9'-bianthrile (abbreviation: BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviation: DPNS), Condensed aromatic compounds such as 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviation: DPNS2), 3,3',3''-(benzene-1,3,5-triyl)tripyrene (abbreviation: TPB3), 9,10-diphenylanthracene (abbreviation: DPAnth), 6,12-dimethoxy-5,11-diphenylchrysene; and

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

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

[Chemical formula 175]

[Chemical formula 176]

[Chemical formula 177]

In one embodiment of the organic EL device according to the present invention, when the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, at least one of the components constituting the first light-emitting layer is different from the components constituting the second light-emitting layer. For example, an embodiment in which a dopant material included in the first light-emitting layer is different from a dopant material included in the second light-emitting layer, or an embodiment in which a host material included in the first light-emitting layer is different from a host material included in the second light-emitting layer may be exemplified.

In the organic EL device of the present invention, the light-emitting layer may contain a light-emitting compound that exhibits fluorescent emission having a main peak wavelength of 500 nm or less (hereinafter, also sometimes simply referred to as a "fluorescent light-emitting compound"). The lower limit of the main peak wavelength is not particularly limited as long as the effect of the present invention is exhibited, but in one embodiment of the organic EL device, for example, the lower limit of the main peak wavelength may be 400 nm. Therefore, in one embodiment of the organic EL device, the main peak wavelength may be, for example, 400 to 500 nm.

The method for measuring the main peak wavelength of a compound is as follows. A 5 μmol/L toluene solution of the compound to be measured is prepared, placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of the sample is measured at room temperature (300 K). The emission spectrum can be measured using a spectrofluorophotometer (device name: F-7000) manufactured by Hitachi High-Tech Science Co., Ltd. In addition, the 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 is maximum is referred to as the main peak wavelength. Meanwhile, in this specification, the main peak wavelength is sometimes referred to as the fluorescence emission main peak wavelength (FL-peak).

The above fluorescent luminescent compound may be either the dopant material or the host material.

When the emitting layer is a single layer, only one of the dopant material and the host material may be the fluorescent emitting compound, or both may be the fluorescent emitting compound.

In addition, when the light-emitting layer includes a first light-emitting layer (anode side) and a second light-emitting layer (cathode side), only one of the first light-emitting layer and the second light-emitting layer may contain the fluorescent luminescent compound, or both light-emitting layers may contain the fluorescent luminescent compound. When the first light-emitting layer includes the fluorescent luminescent compound, only one of the dopant material and the host material included in the first light-emitting layer may be the fluorescent luminescent compound, or both may be the fluorescent luminescent compound. In addition, when the second light-emitting layer includes the fluorescent luminescent compound, only one of the dopant material and the host material included in the second light-emitting layer may be the fluorescent luminescent compound, or both may be the fluorescent luminescent compound.

electron transport layer

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

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

In the electron transport layer, for example,

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

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

(3) Polymer compounds can be used.

As metal complexes, for example, tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: _BeBq2 ), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), Examples include (8-quinolinolato)lithium (abbreviation: Liq).

As heteroaromatic compounds, for example, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), An example is 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs).

As polymer compounds, examples thereof include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).

The above material is a material having an electron mobility of 10 ^-6 cm ² /Vs or more. Meanwhile, a material other than the above may be used in the electron transport layer as long as the material has a higher electron transport property than a hole transport property.

Electron injection layer

The electron injection layer is a layer containing a material having high electron injection properties. The electron injection layer can be used with an alkali metal such as lithium (Li) or cesium (Cs), an alkaline earth metal such as magnesium (Mg), calcium (Ca), or strontium (Sr), a rare earth metal such as europium (Eu), or ytterbium (Yb), or a compound containing these metals. Examples of such compounds 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. Furthermore, a plurality of these compounds can be mixed and used.

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

Alternatively, a composite material formed by mixing an organic compound and an electron donor (donor) may be used in the electron injection layer. Such a composite material has excellent electron injection and electron transport properties because the organic compound receives electrons from the electron donor. In this case, the organic compound is preferably a material having excellent transport properties for the received electrons, and specifically, for example, a material constituting the electron transport layer described above (such as a metal complex or a heteroaromatic compound) can be used. The electron donor may be a material that exhibits electron donating properties to the organic compound. Specifically, an alkali metal, an alkaline earth metal, or a rare earth metal is preferable, and examples thereof include lithium, cesium, magnesium, calcium, erbium, and ytterbium. In addition, an alkali metal oxide or an alkaline earth metal oxide is 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 (abbreviation: TTF) may be used.

cathode

For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or 2 of the periodic table, that is, alkali metals such as lithium (Li) or cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), or strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), or ytterbium (Yb), and alloys containing these.

Meanwhile, when forming a cathode using an alkali metal, an alkaline earth metal, or an alloy containing them, a vacuum deposition method or a sputtering method can be used. In addition, when using silver paste, etc., a coating method or an inkjet method can be used.

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

Insulating layer

Since organic EL elements apply an electric field to an ultra-thin film, pixel defects due to leakage or short-circuiting are likely to occur. To prevent this, an insulating layer made of an insulating thin film may be inserted between a pair of electrodes.

Examples of materials used in the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, and vanadium oxide. Meanwhile, mixtures or laminates thereof may also be used.

space layer

The above space layer is a layer provided between the fluorescent emitting layer and the phosphorescent emitting layer, for example, when laminating a fluorescent emitting layer and a phosphorescent emitting layer, for the purpose of preventing excitons generated in the phosphorescent emitting layer from diffusing into the fluorescent emitting layer or adjusting the carrier balance. In addition, the space layer may also be provided between a plurality of phosphorescent emitting layers.

Since the space layer is provided between the light-emitting layers, it is preferable that it be a material having both electron transport properties and hole transport properties. In addition, in order to prevent the diffusion of triplet energy within the adjacent phosphorescent light-emitting layer, it is preferable that the triplet energy is 2.6 eV or higher. As the material used for the space layer, the same as that used for the hole transport layer described above can be mentioned.

Low floor

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

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

The film thickness of each layer is not particularly limited, but generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and conversely, if the film thickness is too thick, a high driving voltage is required, resulting in poor efficiency. Therefore, it is usually 5 nm to 10 μm, and 10 nm to 0.2 μm is more preferable.

In the organic EL device having a two-layer or three-layer hole transport layer of the present invention, the total thickness of the first hole transport layer and the second hole transport layer is preferably 30 nm or more and 150 nm or less, more preferably 40 nm or more and 130 nm or less.

In addition, in one embodiment of the present invention, the thickness of the second hole transport layer of the two-layer structure or the three-layer structure is preferably 5 nm or more, more preferably 20 nm or more, further preferably 25 nm or more, particularly preferably 35 nm or more, and further preferably 100 nm or less.

In other words, in one embodiment of the present invention, the thickness of the second hole transport layer of the two-layer structure or the three-layer structure is, for example, preferably 5 to 100 nm, more preferably 20 to 100 nm, still more preferably 25 to 100 nm, and particularly preferably 35 to 100 nm.

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

In addition, in the organic EL device having a two-layer structure or a three-layer structure hole transport layer of the present invention, the ratio of the film thickness D2 of the second hole transport layer to the film thickness D1 of the first hole transport layer is preferably 0.3<D2/D1<4.0, more preferably 0.5<D2/D1<3.5, and even more preferably 0.75<D2/D1<3.0.

Preferred embodiments of the organic EL device of the present invention include, for example,

(1) Organic EL device having a two-layer hole transport layer

· A first embodiment, wherein the second hole transport layer comprises the invention compound and the first hole transport layer does not comprise the invention compound;

· A second embodiment, wherein both the first hole transport layer and the second hole transport layer comprise the inventive compound;

· A third embodiment, wherein the first hole transport layer comprises the invention compound and the second hole transport layer does not comprise the invention compound;

(2) Organic EL device having a three-layer hole transport layer

· A fourth embodiment, wherein the first hole transport layer comprises the invention compound, and the second and third hole transport layers do not comprise the invention compound;

· A fifth embodiment, wherein the second hole transport layer comprises the invention compound, and the first and third hole transport layers do not comprise the invention compound;

· A sixth embodiment, wherein the third hole transport layer comprises the invention compound, and the first and second hole transport layers do not comprise the invention compound;

· A seventh embodiment, wherein the first and second hole transport layers comprise the invention compound, and the third hole transport layer does not comprise the invention compound;

· An 8th embodiment, wherein the first and third hole transport layers comprise the invention compound, and the second hole transport layer does not comprise the invention compound;

· A ninth embodiment, wherein the second and third hole transport layers comprise the invention compound, and the first hole transport layer does not comprise the invention compound;

· A 10th embodiment, wherein all of the first to third hole transport layers comprise the inventive compound; etc.

Electronic devices

The above organic EL element can be used in, for example, display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and electronic devices such as light-emitting devices for lighting and vehicle lighting. That is, an electronic device, which is one aspect of the present invention, includes the above organic EL element.

Example

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

Inventive compound used in the manufacture of organic EL device (I) of Example 1

[Chemical formula 178]

Comparative compound used in the manufacture of organic EL device (I) of comparative examples 1 and 2

[Chemical Formula 179]

Other compounds used in the manufacture of organic EL devices (I) of Example 1 and Comparative Examples 1 and 2

[Chemical Formula 180]

Fabrication of organic EL devices (I)

Example 1

A 25 mm × 75 mm × 1.1 mm ITO transparent electrode (anode)-attached glass substrate (manufactured by Geomatech Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.

The glass substrate with ITO transparent electrode attached after cleaning was mounted on the substrate holder of a vacuum deposition device.

First, compound HT-1-1 and compound HA were co-deposited on the surface where the transparent electrode was formed to cover the transparent electrode, thereby forming a hole injection layer with a film thickness of 10 nm. The mass ratio of compound HT-1-1 and compound HA (HT-1-1:HA) was 97:3.

Next, compound HT-1-1 was deposited on the hole injection layer to form a first hole transport layer with a film thickness of 40 nm.

Next, the invention compound Inv-1 was deposited on the first hole transport layer to form a second hole transport layer with a film thickness of 45 nm.

Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited on the second hole transport layer to form a light-emitting layer with a film thickness of 20 nm. The mass ratio of compound BH-1 and compound BD-1 (BH-1:BD-1) was 99:1.

Next, compound ET-1 was deposited on the emitting layer to form a first electron transport layer with a film thickness of 5 nm.

Next, compound ET-2 and Liq were co-deposited on the first electron transport layer to form a second electron transport layer with a film thickness of 25 nm. The mass ratio of compound ET-2 and Liq (ET-2:Liq) was 50:50.

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

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

The layer configuration (device configuration (I)) of the organic EL device (I) obtained in this manner is shown below.

ITO (130)/HT-1-1:HA=97:3 (10)/HT-1-1 (40)/Inv-1 (45)/BH-1:BD-1=99:1 (20) /ET-1 (5)/ET-2:Liq=50:50 (25)/Yb (1)/Al (50)

In the above layer composition, the number in parentheses is the film thickness (nm), and the ratio is the mass ratio.

Comparative examples 1 and 2

An organic EL device (I) was manufactured in the same manner as in Example 1, except that, instead of the inventive compound Inv-1 used as the second hole transport layer material, the comparative compound Ref-1 or the comparative compound Ref-2 was used, respectively, as shown in Table 1 below.

Evaluation of organic EL devices (I)

(1) Measurement of external quantum efficiency (EQE)

The obtained organic EL device (I) was driven by a direct current at room temperature and a current density of 10 mA/cm ² . The luminance was measured using a luminance meter (Minolta Spectrophotometer CS-1000), and the external quantum efficiency (%) was obtained from the results. The results are shown in Table 1 below.

As is clear from the results in Table 1, it can be seen that the inventive compound Inv-1 can provide an organic EL device having a higher external quantum efficiency than the comparative compounds Ref-1 and Ref-2.

Inventive compound used in the manufacture of organic EL device (II) of Example 2

[Chemical Formula 181]

Comparative compound used in the manufacture of organic EL device (II) of Comparative Example 3

[Chemical formula 182]

Other compounds used in the manufacture of organic EL device (II) of Example 2 and Comparative Example 3

[Chemical formula 183]

Fabrication of organic EL devices (II)

Example 2

A 25 mm × 75 mm × 1.1 mm ITO transparent electrode (anode)-attached glass substrate (manufactured by Geomatech Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.

The glass substrate with ITO transparent electrode attached after cleaning was mounted on the substrate holder of a vacuum deposition device.

First, compound HT-1-2 and compound HA were co-deposited on the surface where the transparent electrode was formed to cover the transparent electrode, thereby forming a hole injection layer with a film thickness of 10 nm. The mass ratio of compound HT-1-2 and compound HA (HT-1-2:HA) was 97:3.

Next, compound HT-1-2 was deposited on the hole injection layer to form a first hole transport layer with a film thickness of 40 nm.

Next, the invention compound Inv-2 was deposited on the first hole transport layer to form a second hole transport layer with a film thickness of 40 nm.

Next, compound HT-3 was deposited on the second hole transport layer to form a third hole transport layer with a film thickness of 5 nm.

Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited on the third hole transport layer to form a light-emitting layer with a film thickness of 20 nm. The mass ratio of compound BH-1 and compound BD-1 (BH-1:BD-1) was 99:1.

Next, compound ET-1 was deposited on the emitting layer to form a first electron transport layer with a film thickness of 5 nm.

Next, compound ET-2 and Liq were co-deposited on the first electron transport layer to form a second electron transport layer with a film thickness of 25 nm. The mass ratio of compound ET-2 and Liq (ET-2:Liq) was 50:50.

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

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

The layer configuration (device configuration (II)) of the organic EL device (II) obtained in this manner is shown below.

ITO (130)/HT-1-2:HA=97:3 (10)/HT-1-2 (40)/Inv-2 (40)/HT-3 (5)/BH-1:BD-1 =99:1 (20)/ET-1 (5)/ET-2:Liq=50:50 (25)/Yb (1)/Al (50)

In the above layer composition, the number in parentheses is the film thickness (nm), and the ratio is the mass ratio.

Comparative Example 3

An organic EL device (II) was produced in the same manner as in Example 2, except that, instead of the inventive compound Inv-2 used as the second hole transport layer material, the comparative compound Ref-3 was used, as shown in Table 2 below.

Evaluation of organic EL devices (II)

(1) Measurement of external quantum efficiency (EQE)

The obtained organic EL device (II) was driven by a direct current at room temperature and a current density of 10 mA/cm ² . The luminance was measured using a luminance meter (Minolta Spectrophotometer CS-1000), and the external quantum efficiency (%) was obtained from the results. The results are shown in Table 2 below.

As is clear from the results in Table 2, it can be seen that the inventive compound Inv-2 can provide an organic EL device having a higher external quantum efficiency than the comparative compound Ref-3.

Inventive compound used in the manufacture of organic EL device (III) of examples 3 to 6

[Chemical formula 184]

Comparative compounds used in the manufacture of organic EL devices (III) of Comparative Examples 4 to 6

[Chemical formula 185]

Other compounds used in the production of organic EL devices (III) of Examples 3 to 6 and Comparative Examples 4 to 6

[Chemical formula 186]

Fabrication of organic EL devices (III)

Example 3

A 25 mm × 75 mm × 1.1 mm ITO transparent electrode (anode)-attached glass substrate (manufactured by Geomatech Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.

The glass substrate with ITO transparent electrode attached after cleaning was mounted on the substrate holder of a vacuum deposition device.

First, compound HT-1-3 and compound HA were co-deposited on the surface where the transparent electrode was formed to cover the transparent electrode, thereby forming a hole injection layer with a film thickness of 10 nm. The mass ratio of compound HT-1-3 and compound HA (HT-1-3:HA) was 97:3.

Next, compound HT-1-3 was deposited on the hole injection layer to form a first hole transport layer with a film thickness of 30 nm.

Next, the invention compound Inv-5 was deposited on the first hole transport layer to form a second hole transport layer with a film thickness of 40 nm.

Next, compound HT-4 was deposited on the second hole transport layer to form a third hole transport layer with a film thickness of 15 nm.

Next, compound BH-2 (host material) and compound BD-2 (dopant material) were co-deposited on the third hole transport layer to form a light-emitting layer with a film thickness of 20 nm. The mass ratio of compound BH-2 and compound BD-2 (BH-2:BD-2) was 98:2.

Next, compound ET-3 was deposited on the emitting layer to form a first electron transport layer with a film thickness of 10 nm.

Next, compound ET-4 and Li were co-deposited on the first electron transport layer to form a second electron transport layer with a film thickness of 20 nm. The mass ratio of compound ET-4 and Li (ET-4:Li) was 96:4.

Then, metal Al was deposited on the second electron transport layer to form a metal cathode with a film thickness of 80 nm.

The layer configuration (device configuration (III)) of the organic EL device (III) obtained in this manner is shown below.

ITO (130)/HT-1-3:HA=97:3 (10)/HT-1-3 (30)/Inv-5 (40)/HT-4 (15)/BH-2:BD-2 =98:2 (20)/ET-3 (10)/ET-4:Li=96:4 (20)/Al (80)

In the above layer composition, the number in parentheses is the film thickness (nm), and the ratio is the mass ratio.

Examples 4 to 6

An organic EL device (III) was produced in the same manner as in Example 3, except that instead of the inventive compound Inv-5 used as the second hole transport layer material, the inventive compound Inv-6, the inventive compound Inv-7, or the inventive compound Inv-8 was used, respectively, as shown in Table 3 below.

Comparative examples 4-6

An organic EL device (III) was manufactured in the same manner as in Example 3, except that, instead of the inventive compound Inv-5 used as the second hole transport layer material, comparative compound Ref-4, comparative compound Ref-5, or comparative compound Ref-6 was used, respectively, as shown in Table 3 below.

Evaluation of organic EL devices (III)

(1) Measurement of external quantum efficiency (EQE)

The obtained organic EL device (III) was driven by a direct current at room temperature and a current density of 10 mA/cm ² . The luminance was measured using a luminance meter (Minolta Spectrophotometer CS-1000), and the external quantum efficiency (%) was obtained from the results. The results are shown in Table 3 below.

As is clear from the results in Table 3, it can be seen that the inventive compounds Inv-5 to Inventive compounds Inv-8 can provide organic EL devices having higher external quantum efficiency than the comparative compounds Ref-4 to Ref-6.

Inventive compound synthesized in a synthetic example

[Chemical formula 187]

[Chemical formula 188]

Intermediate Synthesis Example 1: Synthesis of Intermediate A

[Chemical Formula 189]

Under an argon atmosphere, a mixture of 11.9 g (30.0 mmol) of 9-(3-bromophenyl)-9-phenyl-9H-fluorene, 10.5 g (31.5 mmol) of 9,9-diphenyl-9H-fluoren-2-amine, 0.549 g (0.600 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.747 g (1.20 mmol) of 2,2-bis(diphenylphosphino)-1,1'-binaphthyl, 3.17 g (33.0 mmol) of sodium-t-butoxide, and 200 mL of toluene was stirred at 100°C for 6 hours. After cooling the reaction solution to room temperature, it was concentrated under reduced pressure. The obtained solid was purified by silica gel column chromatography to obtain intermediate A as a white solid (19.1 g). The yield was 98%.

Intermediate Synthesis Example 2: Synthesis of Intermediate B

(Synthesis of intermediate B-1)

[Chemical formula 190]

Under an argon atmosphere, a mixture of 10.4 g (30.0 mmol) of 2-bromo-4,4'-di-tert-butyl-1,1'-biphenyl and 150 mL of tetrahydrofuran was cooled to -78°C, 22.5 mL (36.0 mmol) of 1.6 M n-butyllithium hexane solution was added dropwise, and the mixture was stirred for 1 hour. Thereafter, a mixture of 7.83 g (30.0 mmol) of 3-bromophenone and 60 mL of tetrahydrofuran was added dropwise, and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction solution, extracted with ethyl acetate, and washed with saturated brine. The organic layer was dehydrated over magnesium sulfate and concentrated under reduced pressure to obtain 15.7 g of intermediate B-1. Intermediate B-1 was used in the following reaction without purification.

(Synthesis of intermediate B)

[Chemical Formula 191]

A mixture of 15.7 g (29.7 mmol) of intermediate B-1, 11.9 mL of methanesulfonic acid, and 350 mL of dichloromethane was refluxed at the boiling point for 2 hours. After the reaction solution was cooled to room temperature, a saturated aqueous sodium bicarbonate solution was added, and the organic layer was dehydrated with magnesium sulfate and concentrated under reduced pressure. The obtained solid was purified by silica gel column chromatography to obtain intermediate B as a white solid (9.32 g). The yield of the second process was 61%.

Synthesis Example 1: Synthesis of the invention compound Inv-1

[Chemical formula 192]

Under an argon atmosphere, a mixture of 5.26 g (10.0 mmol) of N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine, 3.97 g (10.0 mmol) of 9-(3-bromophenyl)-9-phenyl-9H-fluorene, 0.183 g (0.200 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.232 g (0.800 mmol) of tri-tert-butylphosphonium tetrafluoroborate, 4.2 mL of sodium-t-pentoxide (40% toluene solution), and 67 mL of toluene was refluxed for 6 hours. After cooling the reaction solution to room temperature, it was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 2.76 g of a white solid. The yield was 33%.

The obtained white solid was, as a result of mass spectrum analysis, the inventive compound Inv-1, and had a molecular weight of 842.10 with m/e = 842.

Synthesis Example 2: Synthesis of the invention compound Inv-2

[Chemical formula 193]

Except that N-(9,9-diphenyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine was used instead of N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine used in Synthesis Example 1, the same operation as Synthesis Example 1 was performed to obtain a white solid.

The obtained white solid was, as a result of mass spectrum analysis, the inventive compound Inv-2, and had a molecular weight of 878.13 and m/e=878.

Synthesis Example 3: Synthesis of the invention compound Inv-3

[Chemical Formula 194]

Under an argon atmosphere, a mixture of 2.86 g (4.40 mmol) of intermediate A, 2.46 g (4.84 mmol) of 2'-bromo-2,7-di-tert-butyl-9,9'-spirobi[fluorene], 0.081 g (0.088 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.102 g (0.352 mmol) of tri-tert-butylphosphonium tetrafluoroborate, 0.592 g (6.16 mmol) of sodium-t-butoxide, and 88 mL of xylene was stirred at 110°C for 7 hours. After cooling to room temperature, the reaction solution was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 2.65 g of a white solid. The yield was 56%.

The obtained white solid was, as a result of mass spectrum analysis, the inventive compound Inv-3, and had a molecular weight of 1076.44 and m/e=1076.

Synthesis Example 4: Synthesis of the invention compound Inv-4

[Chemical Formula 195]

Except that 2-bromospyro[adamantane-2,9'-fluorene] was used instead of 2'-bromo-2,7-di-tert-butyl-9,9'-spirobi[fluorene] used in Synthesis Example 3, the same operation as Synthesis Example 3 was performed to obtain a white solid.

The obtained white solid was, as a result of mass spectrum analysis, the inventive compound Inv-4, and had a molecular weight of 934.24 and m/e=934.

Synthesis Example 5: Synthesis of the invention compound Inv-5

[Chemical formula 196]

Except that intermediate B was used instead of 9-(3-bromophenyl)-9-phenyl-9H-fluorene used in Synthesis Example 1, the same operation as in Synthesis Example 1 was performed to obtain a white solid.

The obtained white solid was, as a result of mass spectrum analysis, the inventive compound Inv-5, and had a molecular weight of 954.31 and m/e=954.

Synthesis Example 6: Synthesis of the invention compound Inv-6

[Chemical formula 197]

In Synthesis Example 1, N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine was used instead of N,9,9-triphenyl-9H-fluoren-2-amine, and intermediate B was used instead of 9-(3-bromophenyl)-9-phenyl-9H-fluorene, and the same operation as Synthesis Example 1 was performed to obtain a white solid.

The obtained white solid was, as a result of mass spectrum analysis, the inventive compound Inv-6, and had a molecular weight of 838.15 with m/e = 838.

Synthesis Example 7: Synthesis of the invention compound Inv-7

[Chemical formula 198]

In Synthesis Example 1, N-((1,1'-biphenyl)-2-yl)-9,9-diphenyl-9H-fluoren-2-amine was used instead of N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine, and Intermediate B was used instead of 9-(3-bromophenyl)-9-phenyl-9H-fluorene, except that the same operation as Synthesis Example 1 was performed to obtain a white solid.

The obtained white solid was, as a result of mass spectrum analysis, the inventive compound Inv-7, and had a molecular weight of 914.25 and m/e=914.

Synthesis Example 8: Synthesis of the invention compound Inv-8

[Chemical Formula 199]

In Synthesis Example 1, N-(9,9'-diphenyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine was used instead of N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine, and Intermediate B was used instead of 9-(3-bromophenyl)-9-phenyl-9H-fluorene, except that the same operation as Synthesis Example 1 was performed to obtain a white solid.

The obtained white solid was, as a result of mass spectrum analysis, the inventive compound Inv-8, and had a molecular weight of 1078.46 and m/e=1078.

1, 11, 12 Organic EL devices
2 substrates
3 anode
4 cathode
5 luminous layer
6 Hole transport band (hole transport layer)
6a hole injection layer
6b 1st hole transport layer
6c 2nd hole transport layer
6d 3rd hole transport layer
7 Electron transport band (electron transport layer)
7a 1st electron transport layer
7b Second electron transport layer
10, 20, 30 luminous units

Claims (37)

A compound represented by the following formula (1).

[In equation (1),
N* is the central nitrogen atom.
Ra and Rb are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
However, Ra and Rb may be combined with each other to form a ring structure, or may not be combined with each other to form a ring structure;
When Ra and Rb do not bond to each other to form a ring structure, at least one selected from Ra and Rb is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.
R ¹ to R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
However, one selected from R ¹ to R ⁸ is a single bond bonding to *1;
At least one group of two or more adjacent groups selected from R ¹ to ^{R 8} , which are not single bonds bonded to the above *1, may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may not be bonded to each other to form a ring.
Rc is 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.
R ¹¹ to R ¹⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
However, at least one group of two or more adjacent groups selected from R ¹¹ to R ¹⁸ may be combined with each other to form one or more substituted or unsubstituted benzene rings, or may not be combined with each other to form a ring.
R ²¹ to R ²⁴ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
However, at least one group of two or more adjacent groups selected from R ²² to R ²⁴ may be combined with each other to form one or more substituted or unsubstituted benzene rings, or may not be combined with each other to form a ring.
L ¹ , L ² , and L ³ are each independently a single bond or an unsubstituted ring-forming arylene group having 6 to 12 carbon atoms.
Ar is a group represented by the following formula (1a), (1b), (1c), (1d), (1e), or (1f).

(In equation (1a),
*11 is the binding position to L ³ .
Rd and Rf are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
However, Rd and Rf may be combined with each other to form a ring structure, or may not be combined with each other to form a ring structure.
R ³¹ to R ³⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms;
However, one selected from R ³¹ to R ³⁸ is a single bond bonding to *12;
At least one group of two or more adjacent groups selected from R ³¹ to R ³⁸ , which are not single bonds bonded to the above *12, may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may not be bonded to each other to form a ring.)

(In equation (1b),
*21 is the binding position to L ³ .
One selected from R ¹⁰¹ to R ¹⁰⁵ is a single bond bonding to *22, and one selected from R ¹⁰⁶ to R ¹¹⁰ is a single bond bonding to *23;
R ¹⁰¹ to ^{R 105} , which are not single bonds bonding to the above *22, and R ¹⁰⁶ to R ¹¹⁰ , which are not single bonds bonding to the above *23, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
Two adjacent groups selected from R ¹⁰¹ to R ¹⁰⁵ that are not single bonds bonding to the above *22 do not bond to each other and therefore do not form a ring;
Two adjacent groups selected from R ¹⁰⁶ to R ¹¹⁰ that are not single bonds bonded to the above *23 do not bond to each other and therefore do not form a ring.
R ¹¹¹ to R ¹¹⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
However, two adjacent groups selected from R ¹¹¹ to ^{R 115} do not bind to each other and therefore do not form a ring.)

(In equation (1c),
*24 is the binding position to L ³ .
R ¹²¹ to R ¹²⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
However, one selected from R ¹²¹ to ^{R 128} is a single bond bonding to *25, and two adjacent ones selected from R ¹²¹ to R ¹²⁸ that are not single bonds bonding to *25 do not bond to each other and therefore do not form a ring.)

(In equation (1d),
*26 is the binding position to L ³ .
R ¹³¹ to R ¹⁴⁰ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
However, one selected from R ¹³¹ to ^{R 140} is a single bond bonding to *27, and two adjacent ones selected from R ¹³¹ to R ¹⁴⁰ that are not single bonds bonding to *27 do not bond to each other and therefore do not form a ring.)

(In equation (1e),
*28 is the binding position to L ³ .
R ¹⁵¹ to R ¹⁵⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
However, one selected from R ¹⁵¹ to R ¹⁵⁵ is a single bond bonding to *29, and the other selected from R ¹⁵¹ to R ¹⁵⁵ is a single bond bonding to *30;
Two adjacent groups selected from R ¹⁵¹ to R ¹⁵⁵ , which are neither a single bond bonding to the above *29 nor a single bond bonding to the above *30, do not bond to each other and therefore do not form a ring.
However, if L ³ is a single bond and R ¹⁵² is a single bond bonding to *29, then R ¹⁵¹ , R ¹⁵³ , or R ¹⁵⁴ is a single bond bonding to *30;
If L ³ is a single bond, and also R ¹⁵³ is a single bond bonding to *29, then R ¹⁵² or R ¹⁵⁴ is a single bond bonding to *30;
If L ³ is a single bond and also R ¹⁵⁴ is a single bond bonding to *29, then R ¹⁵² , R ¹⁵³ , or R ¹⁵⁵ is a single bond bonding to *30.
R ¹⁶¹ to ^{R 165} and R ¹⁷¹ to R ¹⁷⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
However, at least one group of two or more adjacent groups selected from R ¹⁶¹ to R ¹⁶⁵ may be combined with each other to form one or more substituted or unsubstituted benzene rings, or may not be combined with each other to form a ring;
At least one group of two or more adjacent groups selected from R ¹⁷¹ to R ¹⁷⁵ may be combined with each other to form one or more substituted or unsubstituted benzene rings, or may not be combined with each other to form a ring.

(In equation (1f),
*31 is the binding position to L ³ .
R ¹⁸¹ to R ¹⁹² are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
However, one selected from R ¹⁸¹ to ^{R 192} is a single bond bonding to *32, and two adjacent ones selected from R ¹⁸¹ to ^{R 192} that are not single bonds bonding to *32 do not bond to each other and therefore do not form a ring.)] In paragraph 1,
A compound wherein Ra and Rb are each independently an unsubstituted aryl group having 6 to 12 ring carbon atoms. In claim 1 or 2,
A compound wherein Rc is an aryl group having 6 to 12 unsubstituted ring carbon atoms. In paragraph 1,
A compound wherein Ra, Rb and Rc are each independently a substituted or unsubstituted phenyl group. In any one of claims 1 to 4,
A compound wherein L ¹ and L ² are each independently a single bond or an unsubstituted phenylene group. In any one of claims 1 to 5,
A compound wherein L ³ is a single bond or an unsubstituted phenylene group. In any one of claims 1 to 6,
A compound in which Ar is a group represented by the above formula (1a) or (1b). In any one of claims 1 to 7,
A compound wherein Ar is a group represented by the above formula (1a), and furthermore, in the above formula (1a), R ³² or R ³⁷ is a single bond bonded to *12. In any one of claims 1 to 7,
A compound wherein L ³ is a single bond, Ar is a group represented by the above formula (1b), and further, in the above formula (1b), R ¹⁰¹ or R ¹⁰⁵ is a single bond bonding to *22. In any one of claims 1 to 9,
*A compound in which all of R ¹ to R ⁸ , R ¹¹ to ^{R 18} , and R ²¹ to R ²⁴ , which are not single bonds bonding to *1, are hydrogen atoms. In any one of claims 1 to 10,
A compound containing at least one deuterium atom. A compound represented by the following formula (2).

[In equation (2),
N* is the central nitrogen atom.
Raa and Rbb are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
However, Raa and Rbb may be combined with each other to form a ring structure, or may not be combined with each other to form a ring structure;
When Raa and Rbb do not bond to each other to form a ring structure, at least one selected from Raa and Rbb is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.
R ⁵¹ to R ⁵⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
However, one selected from R ⁵¹ to R ⁵⁸ is a single bond bonding to *51;
At least one group of two or more adjacent groups selected from R ⁵¹ to R ⁵⁸ , which are not single bonds bonded to the above *51, may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may not be bonded to each other to form a ring.
Rcc is 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.
R ⁶¹ to R ⁶⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
However, at least one group of two or more adjacent groups selected from R ⁶¹ to R ⁶⁸ may be combined with each other to form one or more substituted or unsubstituted benzene rings, or may not be combined with each other to form a ring.
R ⁷¹ to R ⁷⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
However, one selected from R ⁷¹ to R ⁷⁵ is a single bond bonding to *52;
At least one group of two or more adjacent groups selected from R ⁷¹ to R ⁷⁵ , which are not single bonds bonded to the above *52, may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may not be bonded to each other to form a ring.
L ²¹ , L ²² , and L ²³ are each independently a single bond or an unsubstituted ring-forming arylene group having 6 to 12 carbon atoms.
Ar ² is a group represented by the following formula (2a), (2b), (2c), (2d), (2e), or (2f).

(In equation (2a),
*61 is the binding position to L ²³ .
Rdd and Rff are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
However, Rdd and Rff may be combined with each other to form a ring structure, or may not be combined with each other to form a ring structure.
R ⁸¹ to R ⁸⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms;
However, one selected from R ⁸¹ to R ⁸⁸ is a single bond bonding to *62;
At least one group of two or more adjacent groups selected from R ⁸¹ to R ⁸⁸ , which are not single bonds bonded to the above *62, may be bonded to each other to form one or more substituted or unsubstituted benzene rings, or may not be bonded to each other to form a ring.

(In equation (2b),
*70 is the binding position to L ²³ .
One selected from R ²⁹¹ to R ²⁹⁵ is a single bond bonding to *71, one selected from R ³⁰¹ to R ³⁰⁵ is a single bond bonding to *72, and one selected from R ³⁰⁶ to R ³¹⁰ is a single bond bonding to *73;
R ²⁹¹ to R ²⁹⁵ , which are not single bonds bonding to the above *71, R ³⁰¹ to R ³⁰⁵ , which are not single bonds bonding to the above *72, and R ³⁰⁶ to ^{R 310} , which are not single bonds bonding to the above *73, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
Two adjacent groups selected from R ²⁹¹ to R ²⁹⁵ , which are not single bonds bonding to the above *71, do not bond to each other and therefore do not form a ring;
Two adjacent groups selected from R ³⁰¹ to R ³⁰⁵ , which are not single bonds bonding to the above *72, do not bond to each other and therefore do not form a ring;
Two adjacent groups selected from R ³⁰⁶ to R ³¹⁰ that are not single bonds bonded to the above *73 do not bond to each other and therefore do not form a ring.
R ³¹¹ to R ³¹⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
However, two adjacent groups selected from R ³¹¹ to ^{R 315} do not bond to each other and therefore do not form a ring;
m is 0 or 1, n is 0 or 1, and p is 0 or 1;
step,
When m, n and p are 0, *73 indicates the binding position to L ²³ ,
When m and n are 0 and also p is 1, *72 indicates the binding position to L ²³ ,
When m is 0 and also n and p are 1, *71 indicates the binding position to L ²³ ,
When m and p are 0 and n is 1, *71 represents a bonding position to L ²³ , and one selected from R ³⁰¹ to R ³⁰⁵ is a single bond bonding to *73,
When m is 1 and also n and p are 0, one selected from R ²⁹¹ to R ²⁹⁵ is a single bond bonding to *73,
When m and n are 1 and p is 0, one selected from R ³⁰¹ to R ³⁰⁵ is a single bond bonding to *73.)

(In equation (2c),
*74 is the binding position to L ²³ .
R ³²¹ to R ³²⁸ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
However, one selected from R ³²¹ to ^{R 328} is a single bond bonding to *75, and two adjacent ones selected from R ³²¹ to R ³²⁸ that are not single bonds bonding to *75 do not bond to each other and therefore do not form a ring.)

(In equation (2d),
*76 is the binding position to L ²³ .
R ³³¹ to R ³⁴⁰ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
However, one selected from R ³³¹ to ^{R 340} is a single bond bonding to *77, and two adjacent ones selected from R ³³¹ to R ³⁴⁰ that are not single bonds bonding to *77 do not bond to each other and therefore do not form a ring.)

(In equation (2e),
*78 is the binding position to L ²³ .
R ³⁵¹ to R ³⁵⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
However, one selected from R ³⁵¹ to R ³⁵⁵ is a single bond binding to *79, and another selected from R ³⁵¹ to R ³⁵⁵ is a single bond binding to *80;
Two adjacent groups selected from R ³⁵¹ to R ³⁵⁵ , which are neither a single bond bonding to the above *79 nor a single bond bonding to the above *80, do not bond to each other and therefore do not form a ring.
R ³⁶¹ to ^{R 365} and R ³⁷¹ to R ³⁷⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
However, at least one group of two or more adjacent groups selected from R ³⁶¹ to R ³⁶⁵ may be combined with each other to form one or more substituted or unsubstituted benzene rings, or may not be combined with each other to form a ring;
At least one group of two or more adjacent groups selected from R ³⁷¹ to R ³⁷⁵ may be combined with each other to form one or more substituted or unsubstituted benzene rings, or may not be combined with each other to form a ring.

(In equation (2f),
*81 is the binding position to L ²³ .
R ³⁸¹ to R ³⁹² are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;
However, one selected from R ³⁸¹ to ^{R 392} is a single bond bonding to *82, and two adjacent ones selected from R ³⁸¹ to R ³⁹² that are not single bonds bonding to *82 do not bond to each other and therefore do not form a ring.)
However, when L ²¹ is a single bond and Ar ² is represented by formula (2b), the structure having a fluorene skeleton bonded to *51 is not an unsubstituted spirobifluorene;
And, at least one requirement selected from the following requirements (I) and (II) is satisfied;
Requirement (I): R ⁶¹ to R ⁶⁸ , and at least one selected from R ⁷¹ to R ⁷⁵ that is not a single bond bonding to the above *52 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring-forming carbon atoms;
Requirement (II): Rcc is an aryl group having 6 to 30 ring carbon atoms having at least one substituent selected from an alkyl group having 1 to 10 carbon atoms and a cycloalkyl group having 3 to 10 ring carbon atoms.] In Article 12,
A compound wherein Raa and Rbb are each independently an unsubstituted aryl group having 6 to 12 ring carbon atoms. In clause 12 or 13,
A compound wherein Rcc is an unsubstituted aryl group having 6 to 12 ring carbon atoms. In Article 12,
A compound wherein Raa, Rbb and Rcc are each independently a substituted or unsubstituted phenyl group. In any one of paragraphs 12 to 15,
A compound wherein L ²¹ and L ²² are each independently a single bond or an unsubstituted phenylene group. In any one of claims 12 to 16,
L ²³ is a single bond or an unsubstituted phenylene group, a compound. In any one of paragraphs 12 to 17,
Ar ² is a compound represented by the above formula (2a) or (2b). In any one of claims 12 to 18,
A compound wherein Ar ² is a group represented by the above formula (2a), and furthermore, in the above formula (2a), R ⁸² or R ⁸⁷ is a single bond bonded to *62. In any one of claims 12 to 18,
L ²³ is a single bond, Ar ² is a group represented by the above formula (2b), and in the above formula (2b), m, n and p are 0, or
L ²³ is a single bond, Ar ² is a group represented by the above formula (2b), and further, in the above formula (2b), m is 1, further, n and p are 0, and R ²⁹¹ or R ²⁹⁵ is a single bond bonded to *73, or
L ²³ is a single bond, Ar ² is a group represented by the above formula (2b), and further, in the above formula (2b), n is 1, further, m and p are 0, and R ³⁰¹ or R ³⁰⁵ is a single bond bonding to *73, or
A compound wherein L ²³ is a single bond, Ar ² is a group represented by the above formula (2b), and furthermore, in the above formula (2b), m and n are 0, furthermore, p is 1, and R ³⁰⁶ or R ³¹⁰ is a single bond bonding to *73. In any one of paragraphs 12 to 20,
At least one selected from R ⁶¹ to R ⁶⁸ is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms,
A compound wherein all of R ⁶¹ to R ⁶⁶ , which are not the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms and also not the substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, R ⁷¹ to R ⁷⁵ , which are not single bonds bonded to *52, and R ⁵¹ to R ⁵⁸ , which are not single bonds bonded to *51, are hydrogen atoms. In any one of claims 12 to 21,
A compound wherein R ⁷² , R ⁷³ , or R ⁷⁴ is a single bond to *52. In any one of claims 12 to 22,
A compound containing at least one deuterium atom. A material for an organic electroluminescent device comprising a compound according to any one of claims 1 to 23. A hole transport layer material comprising a compound according to any one of claims 1 to 23. An organic electroluminescent device having an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes a light-emitting layer, and at least one layer of the organic layer includes a compound according to any one of claims 1 to 23. In Article 26,
An organic electroluminescent device, wherein the organic layer includes a hole transport band between the anode and the light-emitting layer, and the hole transport band includes the compound. In Article 27,
An organic electroluminescent device, wherein the hole transport band comprises 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 comprise the compound. In paragraph 28,
An organic electroluminescence device, wherein the light-emitting layer and the second hole transport layer are in direct contact. In clause 28 or clause 29,
An organic electroluminescence device, wherein the sum of the thickness of the first hole transport layer and the thickness of the second hole transport layer is 30 nm or more and 150 nm or less. In paragraph 28,
An organic electroluminescence device, wherein the hole transport band includes a first hole transport layer, a second hole transport layer, and a third hole transport layer in order from the anode side, and wherein only the first layer selected from the first to third hole transport layers, only the second layer selected from the first to third hole transport layers, or all layers of the first to third hole transport layers contain the compound. In paragraph 31,
An organic electroluminescence device in which the light-emitting layer and the third hole transport layer are in direct contact. In clause 31 or 32,
An organic electroluminescence device, wherein the sum of the thickness of the first hole transport layer and the thickness of the second hole transport layer is 30 nm or more and 150 nm or less. In any one of paragraphs 26 to 33,
An organic electroluminescent device, wherein the above-mentioned light-emitting layer is a single layer. In any one of paragraphs 26 to 34,
An organic electroluminescent device, wherein the above-mentioned light-emitting layer contains a light-emitting compound that exhibits fluorescence emission having a main peak wavelength of 500 nm or less. In any one of paragraphs 26 to 35,
An organic electroluminescent device, wherein the light-emitting layer comprises a fluorescent dopant material. An electronic device comprising an organic electroluminescent device according to any one of claims 26 to 36.

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