KR20240035723A - Organic electroluminescent element and electronic device - Google Patents

Abstract

The light-emitting layer 5 disposed between the anode 3 and the cathode 4 contains a host material, a sensitizing material, and a fluorescent material, and the host material is a first compound containing a predetermined partial structure in one molecule. and the sensitizing material is one or more compounds selected from the group consisting of phosphorescent metal complexes and delayed fluorescent compounds, and the fluorescent material is selected from the group consisting of a third compound represented by general formula (31) or (32). It is one or more compounds, and the energy gap T _77K (H1) at 77 [K] of the host material and the energy gap T _77K (G2) at 77 [K] of the sensitizing material have the relationship of equation (Equation 1). Satisfactory organic electroluminescence device (1).
T _77K (H1)>T _77K (G2) … (Number 1)

Description

Organic electroluminescent element and electronic device {ORGANIC ELECTROLUMINESCENT ELEMENT AND ELECTRONIC DEVICE}

The present invention relates to organic electroluminescent devices and electronic devices.

When a voltage is applied to an organic electroluminescent element (hereinafter sometimes referred to as an “organic EL element”), holes are injected into the light-emitting layer from the anode, and electrons are also injected into the light-emitting layer from the cathode. And, in the light-emitting layer, the injected holes and electrons recombine to form excitons. At this time, according to the statistical law of electron spin, singlet excitons are generated at a rate of 25%, and triplet excitons are generated at a rate of 75%.

Fluorescent organic EL devices that utilize light emission from singlet excitons are applied to full-color displays such as mobile phones and televisions, but internal quantum efficiency of 25% is considered to be the limit. Therefore, studies are being made to improve the performance of organic EL devices. Performance of organic EL elements includes, for example, luminance, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan.

For example, Document 1 (International Publication No. 2010/134350) discloses an organic EL device using a Triplet-Triplet Fusion (TTF) mechanism, which is one of the mechanisms of delayed fluorescence. The TTF mechanism uses the phenomenon in which a singlet exciton is generated by the collision of two triplet excitons.

It is thought that by using delayed fluorescence by the TTF mechanism described in Document 1, the internal quantum efficiency can be theoretically increased to 40% even in fluorescent light emission. However, in order to improve the performance of electronic devices such as displays, there is a demand to further improve the performance of organic EL elements.

The purpose of the present invention is to provide an organic electroluminescent element that emits light with high efficiency and high color purity, and to provide an electronic device equipped with the organic electroluminescent element.

According to one aspect of the present invention, it includes an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, wherein the light-emitting layer contains a host material, a sensitizing material, and a fluorescent material, and the host material is one A first compound containing in its molecule at least one partial structure selected from the group consisting of partial structures represented by the following general formulas (101) to (118), wherein the sensitizing material is a group consisting of a phosphorescent metal complex and a delayed fluorescent compound. wherein the fluorescent material is one or more compounds selected from the group consisting of a third compound represented by the following general formula (31) or (32), the host material, the sensitizing material, and the fluorescent material. The luminescent materials are different compounds, and the energy gap T _77K (H1) at 77 [K] of the host material and the energy gap T _77K (G2) at 77 [K] of the sensitizing material are expressed by the following formula (Number) An organic electroluminescent device that satisfies the relationship 1) is provided.

T _77K (H1)>T _77K (G2) … (Number 1)

(In the above general formula (101),

A ₁₁ to _{A 16} are each independently a nitrogen atom, CR ₁₁ , or a carbon atom bonded to another atom or other structure in the molecule of the first compound,

However, at least one of A ₁₁ to _{A 16} is a carbon atom bonded to another atom or other structure in the molecule of the first compound,

When there is a plurality of R ₁₁ , the plurality of R ₁₁ are the same or different from each other, and at least one set of two or more adjacent R _11s is present,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

In the general formula (102),

A ₁ to _{A 4} are each independently a nitrogen atom, CR ₁₂ , or a carbon atom bonded to another atom or other structure in the molecule of the first compound,

R ₁₂ is each independently a hydrogen atom or a substituent, or one or more groups of adjacent R ₁₂ are bonded to each other to form a ring,

When there is a plurality of R ₁₂ , the plurality of R ₁₂ are the same or different from each other, and at least one set of two or more adjacent R _12s is present,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

X ₁₀ is NR ₁₃ , C(R ₁₄ )(R ₁₅ ), Si(R ₁₆ )(R ₁₇ ), oxygen atom, sulfur atom, nitrogen bonded to another atom or other structure in the molecule of the first compound. atom, R ₁₈ and a carbon atom each bonding to another atom or other structure in the molecule of the first compound, or R ₁₉ and each bonding to another atom or other structure in the molecule of the first compound It is a silicon atom,

However, at least one of the carbon atom for A ₁ to _{A 4} , the nitrogen atom for X ₁₀ , _{the carbon atom for X 10 and} the silicon atom for combine with other atoms or other structures,

A group consisting of R ₁₄ and R ₁₅ ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

A group consisting of R ₁₆ and R ₁₇ ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

In the general formula (103),

A composition consisting of R ₁₁₅ and R ₁₁₆ ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

In the above general formulas (101) to (104),

R ₁₁ , R ₁₂ , R ₁₄ , R 15 , R ₁₆ , R ₁₇ , _{R 115 and} R ₁₁₆ , and R which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring ₁₃ , R ₁₈ , R ₁₉ and R ₁₁₇ are each independently

hydrogen atom,

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

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

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

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

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

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

A group represented by -O-(R ₉₀₄ ),

A group represented by -S-(R ₉₀₅ ),

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

A group represented by -C(=O)R ₉₀₈ ,

-The group represented by COOR ₉₀₉ ,

A group represented by -P(=O)(R ₉₁₀ )(R ₉₁₁ ),

A group represented by -P(=O)(OR ₉₁₂ )(OR ₉₁₃ ),

A group represented by -Ge(R ₉₁₄ )(R ₉₁₅ )(R ₉₁₆ ),

-A group represented by B(R ₉₁₇ )(R ₉₁₈ ),

Substituted or unsubstituted aralkyl group with 7 to 50 carbon atoms,

halogen Atom,

Cyanogi,

nitro group,

A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or

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

In the above general formulas (103) to (118),

* is a binding site with another atom or other structure in the molecule of the first compound,

When the first compound has a plurality of partial structures each represented by the general formulas (101) to (104),

A plurality of partial structures represented by the general formula (101) are the same or different from each other,

A plurality of partial structures represented by the general formula (102) are the same or different from each other,

A plurality of partial structures represented by the general formula (103) are the same or different from each other,

A plurality of partial structures represented by the general formula (104) are the same or different from each other.)

(In the first compound, R ₉₀₁ to R ₉₁₈ are each independently

hydrogen atom,

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

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

A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or

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

When there is a plurality of R ₉₀₁ , the plurality of R ₉₀₁ are the same or different from each other,

When there is a plurality of R ₉₀₂ , the plurality of R ₉₀₂ are the same or different from each other,

When there is a plurality of R ₉₀₃ , the plurality of R ₉₀₃ are the same or different from each other,

When there is a plurality of R ₉₀₄ , the plurality of R ₉₀₄ are the same or different from each other,

When there is a plurality of R ₉₀₅ , the plurality of R ₉₀₅ are the same or different from each other,

When a plurality of R _906s exist, the plurality of R _906s are the same or different from each other,

When there is a plurality of R ₉₀₇ , the plurality of R ₉₀₇ are the same or different from each other,

When there is a plurality of R ₉₀₈ , the plurality of R ₉₀₈ are the same or different from each other,

When there is a plurality of R ₉₀₉ , the plurality of R ₉₀₉ are the same or different from each other,

When there is a plurality of R ₉₁₀ , the plurality of R ₉₁₀ are the same or different from each other,

When there is a plurality of R ₉₁₁ , the plurality of R ₉₁₁ are the same as or different from each other,

When there is a plurality of R ₉₁₂ , the plurality of R ₉₁₂ are the same or different from each other,

When there is a plurality of R ₉₁₃ , the plurality of R ₉₁₃ are the same or different from each other,

When there is a plurality of R ₉₁₄ , the plurality of R ₉₁₄ are the same or different from each other,

When a plurality of R _915s exist, the plurality of R _915s are the same or different from each other,

When there is a plurality of R ₉₁₆ , the plurality of R ₉₁₆ are the same or different from each other,

When there is a plurality of R ₉₁₇ , the plurality of R ₉₁₇ are the same or different from each other,

When there is a plurality of R ₉₁₈ , the plurality of R ₉₁₈ are the same or different from each other.)

[(In the general formula (31) above,

C ₁ ring and D ₁ ring are,

are joined to each other by a single bond, or

bonded to each other through O, S, NR ₃₃ , Si(R ₃₄ )(R ₃₅ ) or C(R ₃₇ )(R ₃₈ ) or without bonding to each other,

The C 1 ring and the D 1 ring which are not bonded to each other by a single bond and are not bonded to each other through O, S _, NR ₃₃ , Si(R ₃₄ )(R ₃₅ ) or C ₍ R ₃₇ )(R ₃₈ ), And A ₁ ring and B ₁ ring are each independently

A substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 60 carbon atoms, or

It is a substituted or unsubstituted heterocycle with 5 to 60 ring atoms,

The substituent of R _E or R _E is,

It combines with at least one of the A ₁ ring, the substituent of the A ₁ ring, the B ₁ ring, and the substituent of the B ₁ ring to form a substituted or unsubstituted monocycle, or

Combined with at least one of the A ₁ ring, the substituent of the A ₁ ring, the B ₁ ring, and the substituent of the B ₁ ring to form a substituted or unsubstituted condensed ring, or

It does not combine with the A ₁ ring, the substituent of the A ₁ ring, the B ₁ ring, and the substituent of the B ₁ ring.)

(In the above general formula (32),

A ₂ ring, B ₂ ring and C ₂ ring are each independently

A substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 60 carbon atoms, or

It is a substituted or unsubstituted heterocycle with 5 to 60 ring atoms,

The D ₂ ring is a substituted or unsubstituted monocyclic ring having 5 to 7 ring atoms that may be condensed with at least one substituted or unsubstituted non-aromatic ring having 5 to 60 ring atoms,

The C ₂ ring and the D ₂ ring are condensed by sharing a single bond or double bond with each other,

A ₂ ring and D ₂ ring are,

are joined to each other by a single bond, or

bonded to each other through O, S, NR ₃₃ , Si(R ₃₄ )(R ₃₅ ) or C(R ₃₇ )(R ₃₈ ) or without bonding to each other,

The substituent of R _F or R _F is,

It combines with at least one of the A ₂ ring, the substituent of the A ₂ ring, the B ₂ ring, and the substituent of the B ₂ ring to form a substituted or unsubstituted monocycle, or

Combined with at least one of the A ₂ ring, the substituent of the A ₂ ring, the B ₂ ring, and the substituent of the B ₂ ring to form a substituted or unsubstituted condensed ring, or

It does not combine with the A ₂ ring, the substituent of the A ₂ ring, the B ₂ ring, and the substituent of the B ₂ ring.)

(In the above general formula (31) or (32),

R _E which does not combine with the A ₁ ring, the substituents of the A ₁ ring, the B ₁ ring, and the substituents of the B ₁ ring, and the A ₂ ring, the substituents of the A ₂ ring, the B ₂ ring, and the B R _F that is not bonded to the substituent of _{the 2} ring is each independently

hydrogen atom,

A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,

A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,

Substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,

A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 20 carbon atoms,

A substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms,

-CR ₃₉ =Iminyl group represented by N, or

It is a substituted or unsubstituted alkynyl group with 2 to 20 carbon atoms,

Y _E and Y _F are each independently a single bond, O, S, NR ₃₃ , Si(R ₃₄ )(R ₃₅ ) or C(R ₃₇ )(R ₃₈ ),

When Y _E is a single bond, the B ₁ ring and the C ₁ ring are bonded or bonded through O, S, NR ₃₃ , Si(R ₃₄ )(R ₃₅ ) or C(R ₃₇ )(R ₃₈ ) without doing,

When Y _F is a single bond, the B ₂ ring and the C ₂ ring are bonded or bonded through O, S, NR ₃₃ , Si (R ₃₄ ) (R ₃₅ ) or C (R ₃₇ ) (R ₃₈ ) without doing,

R ₃₄ and R ₃₅ are,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

R ₃₇ and R ₃₈ are,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

In the general formula (31), R ₃₃ , R ₃₄ , R ₃₅ , R ₃₇ and R ₃₈ are each independently

Combined with at least one of the A ₁ ring, the B ₁ ring, and the C ₁ ring to form a substituted or unsubstituted monocycle, or

Combined with at least one of the A ₁ ring, the B ₁ ring, and the C ₁ ring to form a substituted or unsubstituted condensed ring, or

Not bonded to the A ₁ ring, the B ₁ ring, and the C ₁ ring,

In the general formula (32), R ₃₃ , R ₃₄ , R ₃₅ , R ₃₇ and R ₃₈ are each independently

Combined with at least one of the A ₂ ring, the B ₂ ring, and the C ₂ ring to form a substituted or unsubstituted monocycle, or

Combined with at least one of the A ₂ ring, the B ₂ ring, and the C ₂ ring to form a substituted or unsubstituted condensed ring, or

Not bonded to the A ₂ ring, the B ₂ ring and the C ₂ ring,

R ₃₉ , and R ₃₃ , R ₃₄ , R ₃₅ , R ₃₇ and R ₃₈ which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently

A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,

A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,

A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or

It is a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,

When there is a plurality of R ₃₃ , the plurality of R ₃₃ are the same or different from each other,

When there is a plurality of R ₃₄ , the plurality of R ₃₄ are the same or different from each other,

When there is a plurality of R ₃₅ , the plurality of R ₃₅ are the same or different from each other,

When there is a plurality of R ₃₇ , the plurality of R ₃₇ are the same or different from each other,

When there is a plurality of R ₃₈ , the plurality of R ₃₈ are the same or different from each other.)]

According to one aspect of the present invention, an electronic device equipped with an organic electroluminescent element according to one aspect of the present invention is provided.

According to one aspect of the present invention, an organic electroluminescent element that emits light with high efficiency and high color purity can be provided, and an electronic device equipped with the organic electroluminescent element can be provided.

1 is a diagram showing the schematic configuration of an example of an organic electroluminescent element according to a first embodiment of the present invention.
Figure 2 is a schematic diagram of an apparatus for measuring transient PL.
Fig. 3 is a diagram showing an example of a transient PL attenuation curve.
4 shows the energy levels and energy transfer relationships of the host material, sensitizing material (delayed fluorescent compound), and fluorescent material in the light-emitting layer of an example of the organic electroluminescence device according to the first embodiment of the present invention. It is a drawing.
Figure 5 shows the energy levels and energy transfer relationships of the host material, sensitizing material (phosphorescence-emitting metal complex), and fluorescent material in the light-emitting layer of an example of the organic electroluminescence device according to the first embodiment of the present invention. This is a drawing.

[Justice]

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

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

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

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

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

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

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

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

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

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

“Substituents described in this specification”

Hereinafter, the substituents described in this specification will be explained.

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

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

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

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

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

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

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

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

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

·「Substituted or unsubstituted aryl group」

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

“Substituted aryl group” means a group in which one or more hydrogen atoms of an “unsubstituted aryl group” are substituted with a substituent. Examples of the “substituted aryl group” include, for example, a group in which one or more hydrogen atoms of the “unsubstituted aryl group” in the specific example group G1A below are substituted with a substituent, and a substituted aryl group in the specific example group G1B below. In addition, the examples of “unsubstituted aryl group” and “substituted aryl group” listed here are only examples, and the “substituted aryl group” described in this specification includes “substituted aryl group” of the specific example group G1B below. Includes groups in which the hydrogen atom bonded to the carbon atom of the aryl group itself in the "aryl group of" is further substituted with a substituent, and groups in which the hydrogen atom of the substituent in the "substituted aryl group" of the specific example group G1B below is further substituted with a substituent. do.

·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 group,

o-terphenyl-2-yl group,

1-naphthyl group,

2-naphthyl group,

anthryl group,

benzoanthryl group,

phenanthryl group,

benzophenanthryl group,

phenalenyl group,

pyrenyl group,

Chrysenyl group,

benzochrysenyl group,

Triphenylenyl group,

Benzotriphenylenyl group,

tetracenyl group,

Pentacenyl group,

fluorenyl group,

9,9'-spirobifluorenyl group,

benzofluorenyl group,

Dibenzofluorenyl group,

fluoranthenyl group,

benzofluoranthenyl group,

perylenyl group, and

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

· Substituted aryl group (specific example group G1B):

o-tolyl group,

m-tolyl group,

p-tolyl group,

para-xylyl group,

meta-xylyl group,

ortho-xylyl group,

para-isopropylphenyl group,

meta-isopropylphenyl group,

ortho-isopropylphenyl group,

para-t-butylphenyl group,

meta-t-butylphenyl group,

ortho-t-butylphenyl group,

3,4,5-trimethylphenyl group,

9,9-dimethylfluorenyl group,

9,9-diphenylfluorenyl group,

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

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

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

cyanophenyl group,

Triphenylsilylphenyl group,

trimethylsilylphenyl group,

phenylnaphthyl group,

a naphthylphenyl group, and

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

·「Substituted or unsubstituted heterocyclic group」

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

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

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

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

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

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

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

·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,

Thiazolyl group,

isothiazolyl group,

thiadiazolyl group,

pyridyl group,

Piri Dajinilgi,

pyrimidinyl group,

Pyrazinyl group,

triazinyl group,

indolyl group,

isoindyl group,

indoliginyl group,

quinolidinyl group,

quinolyl group,

isoquinolyl group,

Shinnolilgi,

Phthalazinyl group,

Quinazolinyl group,

quinoxalinyl group,

benzoimidazolyl group,

indazolyl group,

phenanthrolinyl group,

phenanthridinyl group,

acridinyl group,

phenazinyl group,

carbazolyl group,

benzocarbazolyl group,

morpholino group,

phenoxazinyl group,

phenothiazinyl group,

Azacarbazolyl group, and diazcarbazolyl group.

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

furyl group,

Oxazolyl group,

isoxazolyl group,

Oxadiazolyl group,

xanthenyl group,

benzofuranyl group,

isobenzofuranyl group,

Dibenzofuranyl group,

Naphthobenzofuranyl group,

benzoxazolyl group,

benzoisoxazolyl group,

phenoxazinyl group,

morpholino group,

dinaphthofuranyl group,

Azadibenzofuranyl group,

Diazadibenzofuranyl group,

azanaphthobenzofuranyl group, and

Diazanaphthobenzofuranyl group.

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

thienyl group,

Thiazolyl group,

isothiazolyl group,

thiadiazolyl group,

Benzothiophenyl group (benzothienyl group),

Isobenzothiophenyl group (isobenzothienyl group),

Dibenzothiophenyl group (dibenzothienyl group),

Naphthobenzothiophenyl group (naphthobenzothienyl group),

benzothiazolyl group,

Benzoisothiazolyl group,

phenothiazinyl group,

Dinapthothiophenyl group (dinaphthothienyl group),

Azadibenzothiophenyl group (azadibenzothienyl group),

Diazadibenzothiophenyl group (diazadibenzothienyl group),

Azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and

Diazanaphthobenzothiophenyl group (Diazanaphthobenzothienyl group).

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

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 . Provided that at least one of X _A and Y _A is an oxygen atom, a sulfur atom, or NH.

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

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

(9-phenyl)carbazolyl group,

(9-biphenylyl)carbazolyl group,

(9-phenyl)phenylcarbazolyl group,

(9-naphthyl)carbazolyl group,

diphenylcarbazol-9-yl group,

phenylcarbazole-9-yl group,

Methylbenzoimidazolyl group,

ethylbenzoimidazolyl group,

phenyltriazinyl group,

Biphenyl triazinyl group,

diphenyltriazinyl group,

phenylquinazolinyl group, and

Biphenylyl quinazolinyl group.

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

phenyldibenzofuranyl group,

methyldibenzofuranyl group,

t-butyldibenzofuranyl group, and

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

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

phenyldibenzothiophenyl group,

methyldibenzothiophenyl group,

t-butyldibenzothiophenyl group, and

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

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

The above-mentioned “one or more hydrogen atoms of the monovalent heterocyclic group” refers to 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 When one of X _A and Y _A is CH ₂ , it means one or more hydrogen atoms selected from the hydrogen atoms of the methylene group.

·「Substituted or unsubstituted alkyl group」

Specific examples of the “substituted or unsubstituted alkyl group” (specific example group G3) described in this specification include the following unsubstituted alkyl group (specific example group G3A) and substituted alkyl group (specific example group G3B). (Here, 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”, it includes both “unsubstituted alkyl group” and “substituted alkyl group”.

“Substituted alkyl group” means a group in which one or more hydrogen atoms in the “unsubstituted alkyl group” are substituted with a substituent. Specific examples of the “substituted alkyl group” include a group in which one or more hydrogen atoms in the following “unsubstituted alkyl group” (specific example group G3A) is substituted with a substituent, and examples of a substituted alkyl group (specific example group G3B). . In this specification, the alkyl group in “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”. In addition, the examples of “unsubstituted alkyl group” and “substituted alkyl group” listed here are only examples, and the “substituted alkyl group” described in this specification includes “substituted alkyl group” of specific example group G3B. Includes groups in which the hydrogen atom of the alkyl group itself is also substituted with a substituent, and groups in which the hydrogen atom of the substituent in the “substituted alkyl group” of specific example group G3B is also substituted with a substituent.

·Unsubstituted alkyl group (specific example group G3A):

methyl group,

ethyl group,

n-profile group,

isopropyl group,

n-butyl group,

isobutyl group,

s-butyl group, and

t-butyl group.

· Substituted alkyl group (specific example group G3B):

heptafluoropropyl group (including isomers);

pentafluoroethyl group,

2,2,2-trifluoroethyl group, and

Trifluoromethyl group.

·「Substituted or unsubstituted alkenyl group」

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

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

·Unsubstituted alkenyl group (specific example group G4A):

vinyl machine,

inform,

1-butenyl group,

2-butenyl group, and

3-Butenyl group.

· Substituted alkenyl group (specific example group G4B):

1,3-butanedienyl group,

1-methylvinyl group,

1-methylallyl group,

1,1-dimethylallyl group,

2-methylallyl group, and

1,2-dimethylallyl group.

·「Substituted or unsubstituted alkynyl group」

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

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

·Unsubstituted alkynyl group (specific example group G5A):

Ethynyl group.

·「Substituted or unsubstituted cycloalkyl group」

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

“Substituted cycloalkyl group” means a group in which one or more hydrogen atoms in the “unsubstituted cycloalkyl group” are substituted with a substituent. Specific examples of the “substituted cycloalkyl group” include examples of groups in which one or more hydrogen atoms in the “unsubstituted cycloalkyl group” (specific example group G6A) below are substituted with a substituent, and substituted cycloalkyl groups (specific example group G6B). I can hear it. In addition, the examples of “unsubstituted cycloalkyl group” and “substituted cycloalkyl group” listed here are only examples, and the “substituted cycloalkyl group” described in this specification includes “substituted cycloalkyl group” of specific example group G6B. Groups in which at least one hydrogen atom bonded to the carbon atom of the cycloalkyl group itself in the “alkyl group” is substituted with a substituent and groups in which the hydrogen atom of the substituent in the “substituted cycloalkyl group” of specific example group G6B is further substituted with a substituent are included.

·Unsubstituted cycloalkyl group (specific example group G6A):

cyclopropyl group,

cyclobutyl group,

cyclopentyl group,

cyclohexyl group,

1-adamantyl group,

2-adamantyl group,

1-norbornyl group, and

2-Norbornyl group.

· Substituted cycloalkyl group (specific example group G6B):

4-methylcyclohexyl group.

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

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

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

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

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

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

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

-Si(G6)(G6)(G6)

can be mentioned. here,

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

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

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

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

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

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

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

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

-Si(G3)(G3)(G3) A plurality of G3's are the same or different from each other.

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

·「Group represented by -O-(R ₉₀₄ )」

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

-O(G1),

-O(G2),

-O(G3), and

-O(G6)

can be mentioned.

here,

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

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

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

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

・「Group represented by -S-(R ₉₀₅ )」

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

-S(G1),

-S(G2),

-S(G3), and

-S(G6)

can be mentioned.

here,

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

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

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

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

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

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

-N(G1)(G1),

-N(G2)(G2),

-N(G1)(G2),

-N(G3)(G3), and

-N(G6)(G6)

can be mentioned.

here,

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

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

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

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

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

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

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

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

·「Halogen atom」

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

·「Substituted or unsubstituted fluoroalkyl group」

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

·「Substituted or unsubstituted haloalkyl group」

The “substituted or unsubstituted haloalkyl group” described in this specification means a group in which at least one hydrogen atom bonded to the carbon atom constituting the alkyl group in the “substituted or unsubstituted alkyl group” is substituted with a halogen atom, and “ In “substituted or unsubstituted alkyl group”, groups in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group are substituted with halogen atoms are also included. The carbon number of the “unsubstituted haloalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the specification. “Substituted haloalkyl group” means a group in which one or more hydrogen atoms of the “haloalkyl group” are substituted with a substituent. In addition, in the “substituted haloalkyl group” described in this specification, one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the “substituted haloalkyl group” are also added to the substituent, the substituted group, and the “substituted haloalkyl group”. Also included are groups in which one or more hydrogen atoms of the substituent are substituted with the substituent. Specific examples of the “unsubstituted haloalkyl group” include groups in which one or more hydrogen atoms in the “alkyl group” (specific example group G3) are substituted with a halogen atom. 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), where G3 is a “substituted or unsubstituted alkyl group” described in specific example group G3. The carbon number of the “unsubstituted alkoxy group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the specification.

·「Substituted or unsubstituted alkylthio group」

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

·「Substituted or unsubstituted aryloxy group」

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

·「Substituted or unsubstituted arylthio group」

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

·「Substituted or unsubstituted trialkylsilyl group」

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

·「Substituted or unsubstituted aralkyl group」

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

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

Unless otherwise stated, the substituted or unsubstituted aryl group described in this specification is preferably a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, and p-terphenyl-4-yl group. , p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl -4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, phenanthryl group, pyrenyl group, chrysenyl group, triphenyl group Renyl group, fluorenyl group, 9,9'-spirobifluorenyl group, 9,9-dimethylfluorenyl group, and 9,9-diphenylfluorenyl group.

The substituted or unsubstituted heterocyclic group described in this specification, unless otherwise stated in this specification, is preferably pyridyl group, pyrimidinyl group, triazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, Benzoimidazolyl group, phenanthrolinyl group, carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group or 9-carbazolyl group) , benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group, dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphtho Benzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group or (9-phenyl)carbazol-4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenyl Carbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group.

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

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

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

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

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

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

·「Substituted or unsubstituted arylene group」

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

·「Substituted or unsubstituted divalent heterocyclic group」

Unless otherwise specified, the “substituted or unsubstituted divalent heterocyclic group” described in this specification refers to a divalent group derived by excluding one hydrogen atom on the heterocycle from the “substituted or unsubstituted heterocyclic group” above. am. As a specific example of the “substituted or unsubstituted divalent heterocyclic group” (specific example group G13), 2 is derived by excluding one hydrogen atom on the heterocycle from the “substituted or unsubstituted heterocyclic group” described in specific example group G2. Examples include the group A and the like.

·「Substituted or unsubstituted alkylene group」

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

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

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

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

In the 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 through a single bond to form a ring.

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

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

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

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

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

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

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

·「When combining to form a ring」

In this specification, "one or more sets of two or more adjacent groups combine with each other to form a substituted or unsubstituted monocyclic ring, combine with each other to form a substituted or unsubstituted condensed ring, or do not combine with each other to form a substituted or unsubstituted monocyclic ring. In the case of "one or more sets of two or more adjacent groups combine with each other to form a substituted or unsubstituted monocycle," and "one or more sets of groups consisting of two or more adjacent groups combine with each other." This means a case where “a substituted or unsubstituted condensed ring is formed” and a case where “at least one set of two or more adjacent groups are not bonded to each other.”

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

For example, among R ₉₂₁ to _{R 930} , in the case where “one or more sets of two or more adjacent groups combine with each other to form a ring,” the group consisting of two adjacent groups that constitutes one group, the group of R ₉₂₁ and R ₉₂₂ , R ₉₂₂ and R ₉₂₃ , R ₉₂₃ and R ₉₂₄ , R ₉₂₄ and R ₉₃₀ , R ₉₃₀ and R ₉₂₅ , R ₉₂₅ and R ₉₂₆ , R ₉₂₆ and R ₉₂₇ , R ₉₂₇ and R ₉₂₈ , R ₉₂₈ and R ₉₂₉ , and R ₉₂₉ and R ₉₂₁ .

The above “one or more sets” means that two or more sets of the adjacent two or more sets may 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, when R ₉₂₅ and R ₉₂₆ combine with each other to form ring Q _B , the anthracene compound represented by the general formula (TEMP-103) is It is represented by the following general formula (TEMP-104).

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

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

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

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

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

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

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

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

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

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

Unless otherwise stated in the specification, among “saturated ring” and “unsaturated ring”, “unsaturated ring” is preferable.

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

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

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

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

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

The above is a case in which “one or more sets of two or more adjacent groups combine with each other to form a substituted or unsubstituted monocycle” and “one or more sets of two or more adjacent groups combine with each other to form a substituted or unsubstituted ring” This is an explanation of the case of “forming a condensed ring” (“case of combining to form a ring”).

· Substituents in the case of “substituted or unsubstituted”

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

An unsubstituted alkyl group having 1 to 50 carbon atoms,

An unsubstituted alkenyl group having 2 to 50 carbon atoms,

An unsubstituted alkynyl group having 2 to 50 carbon atoms,

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

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atom, cyano group, nitro group,

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

Unsubstituted heterocyclic group with 5 to 50 ring-forming atoms

A group selected from the group consisting of, etc.

Here, R ₉₀₁ to R ₉₀₇ are each independently

hydrogen atom,

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

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

A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or

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

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

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

When two or more R _903s exist, the two or more R _903s are the same or different from each other,

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

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

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

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

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

An alkyl group with 1 to 50 carbon atoms,

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

It is a group selected from the group consisting of heterocyclic groups having 5 to 50 ring atoms.

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

An alkyl group with 1 to 18 carbon atoms,

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

It is a group selected from the group consisting of heterocyclic groups having 5 to 18 ring atoms.

Specific examples of each group of the above optional substituents are specific examples of the substituents described in the above-mentioned section “Substituents described in this specification.”

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

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

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

In this specification, the formula expressed as “A≥B” means that the value of A and the value of B are the same, or the value of A is greater than the value of B.

In this specification, the formula expressed as “A≤B” means that the value of A and the value of B are the same, or the value of A is smaller than the value of B.

[First Embodiment]

<Organic electroluminescence device>

The organic EL device according to this embodiment will be described.

The organic EL device according to this embodiment has an organic layer between the anode and cathode electrodes. This organic layer includes at least one layer composed of an organic compound. Alternatively, this organic layer is formed by stacking a plurality of layers composed of organic compounds. The organic layer may further contain an inorganic compound.

The organic EL device according to the present embodiment includes an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, the light-emitting layer contains a host material, a sensitizing material, and a fluorescent material, and the host material is one A first compound containing in its molecule at least one partial structure selected from the group consisting of partial structures represented by the following general formulas (101) to (118), wherein the sensitizing material consists of a phosphorescent metal complex and a delayed fluorescent compound. One or more compounds selected from the group, wherein the fluorescent material is one or more compounds selected from the group consisting of a third compound represented by the following general formula (31) or (32), the host material, the sensitizing material, and the above The fluorescent materials are different compounds, and the energy gap T _77K (H1) at 77 [K] of the host material and the energy gap T _77K (G2) at 77 [K] of the sensitizing material are expressed by the following formula ( It satisfies the relationship of number 1).

T _77K (H1)>T _77K (G2) … (Number 1)

According to this embodiment, an organic electroluminescent element that emits light with high efficiency and high color purity can be provided.

In the organic EL device according to this embodiment, the light emitting layer contains a predetermined host material, a sensitizer material, and a fluorescent material. In the emitting layer, recombination of holes and electrons tends to occur not on the fluorescent material but on the molecules of the host material or sensitizing material, and in the sensitizing material, when the sensitizing material is a delayed fluorescent compound, the lowest excitation triplet state is the lowest excitation. It is thought that inverse intersystem crossing occurs in the singlet state, and when the sensitizing material is a phosphorescent metal complex, the lowest singlet excitation state intersystem crossing occurs in the lowest triplet excitation state. In this way, after the energy state transition to the lowest singlet excitation state or lowest triplet excitation state in the sensitizing material occurs efficiently, energy transfer occurs from the sensitizing material to the fluorescent material, and the lowest singlet excitation state of the fluorescent material occurs. It is thought that fluorescence emission from this state occurs. In the present embodiment, the third compound represented by the general formula (31) or (32) used as the fluorescent material has a narrow half width of the emission spectrum, so the fluorescent material that receives energy from the sensitizing material has high efficiency and high color. I think it emits light due to its purity.

(organic layer)

In the organic EL device of the present embodiment, the organic layer may be composed of, for example, one light-emitting layer, or may include a layer that can be employed in the organic EL device. The layer that can be employed in the organic EL device is not particularly limited, but for example, at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron barrier layer, a hole barrier layer, an electron transport layer, and an electron injection layer. I can hear it.

In the organic EL device of this embodiment, a hole transport layer may be disposed between the anode and the light emitting layer.

In the organic EL device of this embodiment, an electron transport layer may be disposed between the cathode and the light emitting layer.

Figure 1 shows a schematic configuration of an example of an organic EL device according to this embodiment.

The organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 is formed by sequentially stacking a hole injection layer 6, a hole transport layer 7, a light emitting layer 5, an electron transport layer 8, and an electron injection layer 9 in this order starting from the anode 3 side. . The present invention is not limited to the configuration of the organic EL device shown in FIG. 1.

(Emitting layer)

In one embodiment, the host material, sensitizing material, and fluorescent material are contained in a single layer. For example, when the organic EL element has one light-emitting layer, the host material, sensitizing material, and fluorescent material are contained in the single light-emitting layer, and when the organic EL element has multiple light-emitting layers, they are contained in a single light-emitting layer among the plurality of light-emitting layers. It is contained within.

In one embodiment, when the light-emitting layer contains a delayed fluorescent compound as a sensitizing material, the light-emitting layer does not contain a phosphorescent metal complex.

[Host Material]

In this embodiment, the host material is a first compound containing one or more partial structures selected from the group consisting of partial structures represented by the following general formulas (101) to (118) in one molecule.

(In the above general formula (101),

A ₁₁ to _{A 16} are each independently a nitrogen atom, CR ₁₁ , or a carbon atom bonded to another atom or other structure in the molecule of the first compound,

However, at least one of A ₁₁ to _{A 16} is a carbon atom bonded to another atom or other structure in the molecule of the first compound,

When there is a plurality of R ₁₁ , the plurality of R ₁₁ are the same or different from each other, and at least one set of two or more adjacent R _11s is present,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

In the general formula (102),

A ₁ to _{A 4} are each independently a nitrogen atom, CR ₁₂ , or a carbon atom bonded to another atom or other structure in the molecule of the first compound,

R ₁₂ is each independently a hydrogen atom or a substituent, or one or more groups of adjacent R ₁₂ are bonded to each other to form a ring,

When there is a plurality of R ₁₂ , the plurality of R ₁₂ are the same or different from each other, and at least one set of two or more adjacent R _12s is present,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

X ₁₀ is NR ₁₃ , C(R ₁₄ )(R ₁₅ ), Si(R ₁₆ )(R ₁₇ ), oxygen atom, sulfur atom, nitrogen bonded to another atom or other structure in the molecule of the first compound. atom, R ₁₈ and a carbon atom each bonding to another atom or other structure in the molecule of the first compound, or R ₁₉ and each bonding to another atom or other structure in the molecule of the first compound It is a silicon atom,

However, at least one of the carbon atom for A ₁ to _{A 4} , the nitrogen atom for X ₁₀ , _{the carbon atom for X 10 and} the silicon atom for combine with other atoms or other structures,

A group consisting of R ₁₄ and R ₁₅ ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

A group consisting of R ₁₆ and R ₁₇ ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

In the general formula (103),

A composition consisting of R ₁₁₅ and R ₁₁₆ ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

In the above general formulas (101) to (104),

R ₁₁ , R ₁₂ , R ₁₄ , R 15 , R ₁₆ , R ₁₇ , _{R 115 and} R ₁₁₆ , and R which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring ₁₃ , R ₁₈ , R ₁₉ and R ₁₁₇ are each independently

hydrogen atom,

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

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

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

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

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

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

A group represented by -O-(R ₉₀₄ ),

A group represented by -S-(R ₉₀₅ ),

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

A group represented by -C(=O)R ₉₀₈ ,

-The group represented by COOR ₉₀₉ ,

A group represented by -P(=O)(R ₉₁₀ )(R ₉₁₁ ),

A group represented by -P(=O)(OR ₉₁₂ )(OR ₉₁₃ ),

A group represented by -Ge(R ₉₁₄ )(R ₉₁₅ )(R ₉₁₆ ),

-A group represented by B(R ₉₁₇ )(R ₉₁₈ ),

Substituted or unsubstituted aralkyl group with 7 to 50 carbon atoms,

halogen Atom,

Cyanogi,

nitro group,

A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or

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

In the general formulas (103) to (118),

* is a binding site with another atom or other structure in the molecule of the first compound,

When the first compound has a plurality of partial structures each represented by the general formulas (101) to (104),

A plurality of partial structures represented by the general formula (101) are the same or different from each other,

A plurality of partial structures represented by the general formula (102) are the same or different from each other,

A plurality of partial structures represented by the general formula (103) are the same or different from each other,

A plurality of partial structures represented by the general formula (104) are the same or different from each other.)

(In the first compound, R ₉₀₁ to R ₉₁₈ are each independently

hydrogen atom,

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

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

A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or

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

When there is a plurality of R ₉₀₁ , the plurality of R ₉₀₁ are the same or different from each other,

When there is a plurality of R ₉₀₂ , the plurality of R ₉₀₂ are the same or different from each other,

When there is a plurality of R ₉₀₃ , the plurality of R ₉₀₃ are the same or different from each other,

When there is a plurality of R ₉₀₄ , the plurality of R ₉₀₄ are the same or different from each other,

When there is a plurality of R ₉₀₅ , the plurality of R ₉₀₅ are the same or different from each other,

When there is a plurality of R ₉₀₆ , the plurality of R ₉₀₆ are the same or different from each other,

When there is a plurality of R ₉₀₇ , the plurality of R ₉₀₇ are the same or different from each other,

When there is a plurality of R ₉₀₈ , the plurality of R ₉₀₈ are the same or different from each other,

When there is a plurality of R ₉₀₉ , the plurality of R ₉₀₉ are the same or different from each other,

When there is a plurality of R ₉₁₀ , the plurality of R ₉₁₀ are the same or different from each other,

When there is a plurality of R ₉₁₁ , the plurality of R ₉₁₁ are the same as or different from each other,

When there is a plurality of R ₉₁₂ , the plurality of R ₉₁₂ are the same or different from each other,

When there is a plurality of R ₉₁₃ , the plurality of R ₉₁₃ are the same or different from each other,

When there is a plurality of R ₉₁₄ , the plurality of R ₉₁₄ are the same or different from each other,

When a plurality of R _915s exist, the plurality of R _915s are the same or different from each other,

When there is a plurality of R ₉₁₆ , the plurality of R ₉₁₆ are the same or different from each other,

When there is a plurality of R ₉₁₇ , the plurality of R ₉₁₇ are the same or different from each other,

When there is a plurality of R ₉₁₈ , the plurality of R ₉₁₈ are the same or different from each other.)

In the general formula ( ₁₀₂ ), when It is displayed as .

_In the general formula ( ₁₀₂ ), when It is displayed as (102-2).

In _the general formula ( ₁₀₂ ), when It is displayed as (102-3).

In general formulas (102-1) to (102-3), A ₁ to _{A 4} are each independently the same as A ₁ to _{A 4} in the general formula (102), and R ₁₈ and R ₁₉ are each independently has the same meaning as R ₁₂ in the general formula (102), and * is a bonding site with another atom or other structure in the molecule of the first compound.

In one embodiment, the host material has at least one partial structure represented by the general formula (101).

In one embodiment, the partial structure represented by the general formula (101) is at least one selected from the group consisting of partial structures represented by the following general formulas (A11) to (A19).

(In the general formulas (A11) to (A16), A ₁₂ to A ₁₆ are each independently a nitrogen atom or CR ₁₁ , R ₁₁ is the same as R ₁₁ in the general formula (101), and * is It is a binding site with another atom or other structure in the molecule of the first compound,

In the general formulas (A17) and (A18), A ₁₁ to A ₂₂ are each independently a nitrogen atom, CR ₁₁ or a carbon atom bonded to another atom or other structure in the molecule of the first compound, and R ₁₁ is each independently the same as R ₁₁ in the general formula (101), and at least one of A ₁₁ to _{A 22} is a carbon atom bonded to another atom or another structure in the molecule of the first compound. ,

In the general formula (A19), A ₁₁ to _{A 18} are each independently a nitrogen atom or CR ₁₁ or a carbon atom bonded to another atom or other structure in the molecule of the first compound, and R ₁₁ is each is independently the same as R ₁₁ in the general formula ( ₁₀₁ ), and X ₁₁ and X ₁₂ are each independently the same as X ₁₀ in the general formula ( ₁₀₂ ), and also At least one of the carbon atom, the nitrogen atom at X ₁₁ and X ₁₂ , the carbon atom at X _{11 and} X ₁₂ , and the silicon atom at X _{11 and} combines with other atoms or other structures)

In one embodiment, the host material has at least one partial structure represented by the general formula (102) above.

In one embodiment, the partial structure represented by the general formula (102) is at least one selected from the group consisting of partial structures represented by the following general formulas (B11) to (B24).

(In the general formulas (B11) to (B16), Ax ₁ to _{Ax 4} are each independently a nitrogen atom or CR ₁₂ , and R ₁₂ is each independently the same as R ₁₂ in the general formula (102). , X ₁₀ has _the same meaning as

In the general formula (B17), Ax ₁ , Ax ₂ and Ay ₁ to _{Ay 4} are each independently a nitrogen atom or CR ₁₂ or a carbon atom bonded to another atom or other structure in the molecule of the first compound. , R ₁₂ is each independently the same as R ₁₂ in the general formula (102), and X ₁₀ is the same as X ₁₀ in the general formula (102), provided that Ax ₁ , Ax ₂ and Ay At least one of the carbon atom for ₁ to Ay ₄ , the nitrogen atom for X ₁₀ , the carbon atom for X ₁₀ , and _the silicon atom for combines with other structures,

In the general formula (B18), Ay ₁ to _{Ay 8} are each independently a nitrogen atom or CR ₁₂ or a carbon atom bonded to another atom or other structure in the molecule of the first compound, and R ₁₂ is each Independently the same as R ₁₂ in _the general formula ( ₁₀₂ ) above, X ₁₀ is _{the same} as At least one of _the nitrogen atom, _the carbon atom for

(In the general formulas (B19) to (B24), Ay ₁ to Ay ₈ and Ay ₉ to _{Ay 12} are each independently a nitrogen atom or CR ₁₂ or another atom or other structure in the molecule of the first compound. is a carbon atom bonded to, R ₁₂ is each independently the same as R ₁₂ in the general formula (102), and X ₉ and X ₁₀ are each independently the same as X ₁₀ in the general formula (102) ego,

Carbon atoms at Ay ₁ to Ay ₈ and Ay ₉ to Ay ₁₂ , nitrogen atoms at X ₉ and X ₁₀ , carbon atoms at X ₉ and X ₁₀ , and silicon atoms at X ₉ and X ₁₀ At least one of them is bonded to another atom or other structure in the molecule of the first compound.)

In the first compound of the present embodiment, R ₁₁ , R ₁₂ and R ₁₁₅ to _{R 117} are each independently a hydrogen atom, a halogen atom, a cyano group, an unsubstituted aryl group having 6 to 30 ring carbon atoms, or an unsubstituted aryl group. Heterocyclic group with 5 to 30 ring atoms, unsubstituted alkyl group with 1 to 30 carbon atoms, unsubstituted halogenated alkyl group with 1 to 30 carbon atoms, unsubstituted alkylsilyl group with 3 to 30 carbon atoms, unsubstituted ring forming carbon number. Arylsilyl group with 6 to 60 carbon atoms, unsubstituted arylphosphoryl group with 6 to 60 ring carbon atoms, unsubstituted alkoxy group with 1 to 30 carbon atoms, unsubstituted aryloxy group with 6 to 30 ring carbon atoms, amino group, Unsubstituted alkylamino group with 2 to 30 carbon atoms, unsubstituted ring-forming arylamino group with 6 to 60 carbon atoms, thiol group, unsubstituted alkylthio group with 1 to 30 carbon atoms, or unsubstituted ring-forming aryl group with 6 to 30 carbon atoms. It is preferable that it is a thio group.

In the first compound of the present embodiment, R ₁₁ , R ₁₂ and R ₁₁₅ to _{R 117} are each independently a hydrogen atom, a halogen atom, a cyano group, an unsubstituted aryl group having 6 to 14 ring carbon atoms, or an unsubstituted aryl group. Heterocyclic group with 5 to 14 ring atoms, unsubstituted alkyl group with 1 to 6 carbon atoms, unsubstituted halogenated alkyl group with 1 to 6 carbon atoms, unsubstituted alkylsilyl group with 3 to 6 carbon atoms, unsubstituted ring forming carbon number. Arylsilyl group with 6 to 60 carbon atoms, unsubstituted arylphosphoryl group with 6 to 60 ring carbon atoms, unsubstituted alkoxy group with 1 to 6 carbon atoms, unsubstituted aryloxy group with 6 to 14 ring carbon atoms, amino group, Unsubstituted alkylamino group with 2 to 12 carbon atoms, unsubstituted ring-forming arylamino group with 6 to 60 carbon atoms, thiol group, unsubstituted alkylthio group with 1 to 6 carbon atoms, or unsubstituted ring-forming aryl group with 6 to 14 carbon atoms. It is more preferable that it is a thio group.

In the first compound of the present embodiment, it is more preferable that R ₁₁ , R ₁₂ and R ₁₁₅ to _{R 117} are hydrogen atoms.

In the first compound of the present embodiment, R ₁₃ to R ₁₉ in X ₁₀ and R ₁₃ to _{R 19} in _{X 9} (same as R ₁₃ to _{R 19} in Atom, unsubstituted aryl group with 6 to 30 ring carbon atoms, unsubstituted heterocyclic group with 5 to 30 ring atoms, unsubstituted alkyl group with 1 to 30 carbon atoms, or unsubstituted halogenated alkyl group with 1 to 30 carbon atoms. It is desirable to be

In the first compound _of the present embodiment, _{R 13 to R 19 for} , an unsubstituted heterocyclic group with 5 to 14 ring atoms, an unsubstituted alkyl group with 1 to 6 carbon atoms, or an unsubstituted halogenated alkyl group with 1 to 6 carbon atoms.

In the first compound _of the present embodiment, _{R 13 to R 19 for} It is more preferable that it is a substituted alkyl group having 1 to 6 carbon atoms.

Examples of partial structures represented by any of the general formulas (101) to (118) above include those represented by the following general formulas (A101) to (A121) and (B101) to (B125).

The first compound preferably contains at least one of the partial structures represented by the following general formulas (A101) to (A121) and (B101) to (B125) in one molecule.

In the general formulas (A101) to (A107), R ₁₀₁ to R ₁₀₆ are each independently the same as R ₁₁ in the general formula (101), and at least one of R ₁₀₁ to _{R 106} is the first It is a single bond that bonds to another atom or other structure in the molecule of a compound.

In the general formulas (A101) to (A107), adjacent groups of R ₁₀₁ and R ₁₀₂ , groups of R ₁₀₂ and R ₁₀₃ , groups of R ₁₀₃ and R ₁₀₄ , groups of R ₁₀₄ and R ₁₀₅ , groups of R ₁₀₅ and The group of R ₁₀₆ and one or more sets of the group of R ₁₀₆ and R ₁₀₁ combine with each other to form a substituted or unsubstituted monocycle, combine with each other to form a substituted or unsubstituted condensed ring, or do not combine with each other. .

In the general formulas (A108) to (A109), R ₁₁₀ is each independently the same as R ₁₁ in the general formula (101), and at least one of R ₁₁₀ is in the molecule of the first compound. It is a single bond bonded to another atom or other structure, the plurality of R ₁₁₀ is the same as or different from each other, and at least one set of the plurality of R ₁₁₀ consisting of two or more adjacent elements is bonded to each other to form a substituted or unsubstituted monocyclic ring. or do not combine with each other to form a substituted or unsubstituted condensed ring, or do not combine with each other.

In the general formulas (A110) to (A114), R ₁₁₀ and R ₁₁₂ to R ₁₁₄ are each independently the same as R ₁₁ in the general formula (101), _{and 102 )} has _{the same meaning} as At least one of the nitrogen atom, carbon atom, and silicon atom is bonded to another atom or other structure in the molecule of the first compound, and the plurality of R ₁₁₀ is the same or different from each other.

In the above general formulas (A110) to (A114), a group consisting of two or more adjacent R ₁₁₀ , a group of R ₁₁₂ and R ₁₁₃ , and a group of R ₁₄ and R ₁₅ in X ₁₁₀ (X _{10 (} agree _{with articles R 14 and} R _{15 in} They form substituted or unsubstituted single rings, combine with each other to form substituted or unsubstituted condensed rings, or do not combine with each other.

In the general formulas (A115) to (A119), R ₁₁₀ and R ₁₁₂ to _{R 114} are each independently the same as R ₁₁ in the general formula (101), provided that R ₁₁₀ and R ₁₁₂ to _{R 114} At least one of them is a single bond that bonds to another atom or other structure in the molecule of the first compound, and the plurality of R ₁₁₀ is the same or different from each other.

In the above general formulas (A115) to (A119), a group consisting of two or more adjacent R ₁₁₀ and one or more groups of R ₁₁₂ and R ₁₁₃ are combined with each other to form a substituted or unsubstituted monocycle. do not form a substituted or unsubstituted condensed ring, or combine with each other.

In the general formulas (A120) to (A121), R ₁₁₀ is each independently the same as R ₁₁ in the general formula (101), provided that at least one of R ₁₁₀ is present in the molecule of the first compound. It is a single bond that bonds to another atom or another structure, and the plurality of R ₁₁₀ is the same or different from each other.

In the general formulas (A120) to (A121), one or more groups of two or more adjacent R _110s combine with each other to form a substituted or unsubstituted monocycle, or combine with each other to form a substituted or unsubstituted ring. They do not form substituted condensed rings or combine with each other.

In the general formulas (B101) to (B109), R ₁₁₄ and R ₁₂₁ to R ₁₃₁ are each independently the same as R ₁₂ in the general formula (102), provided that R ₁₁₄ and R ₁₂₁ to _{R 131} At least one of them is a single bond that bonds to another atom or other structure in the molecule of the first compound.

In the general formulas (B101) to (B102), one or more of the groups of R ₁₂₂ and R ₁₂₃ , the group of R ₁₂₃ and R ₁₁₄ , and the group of R ₁₁₄ and R ₁₂₁ are combined with each other to form a substituted or unsubstituted group. They form single rings, combine with each other to form substituted or unsubstituted condensed rings, or do not combine with each other.

In the general formulas (B105) to (B106), R ₁₂₄ and R ₁₂₅ , R ₁₂₅ and R ₁₂₆ , R ₁₂₆ and R ₁₂₇ , R ₁₂₇ and R ₁₂₈ , and R ₁₂₈ and R One or more sets of ₁₂₉ combine with each other to form a substituted or unsubstituted monocycle, combine with each other to form a substituted or unsubstituted condensed ring, or do not combine with each other.

In the general formula (B107), R ₁₂₄ and R ₁₂₅ , R ₁₂₅ and R ₁₂₆ , R ₁₂₆ and R ₁₂₇ , R ₁₂₇ and R ₁₂₈ , R ₁₂₈ and R ₁₂₉ , R The group of ₁₂₉ and R ₁₁₄ , and one or more groups of R ₁₁₄ and R ₁₂₄ , combine with each other to form a substituted or unsubstituted monocycle, or combine with each other to form a substituted or unsubstituted condensed ring, or combine with each other. I never do that.

In the general formulas (B108) to (B109), one or more of the groups of R ₁₂₄ and R ₁₂₅ , the group of R ₁₂₅ and R ₁₂₆ , the group of R ₁₃₀ and R ₁₃₁ , and the group of R ₁₃₁ and R ₁₂₉ , They combine with each other to form a substituted or unsubstituted single ring, combine with each other to form a substituted or unsubstituted condensed ring, or do not combine with each other.

In the general formulas (B110) to (B117), R ₁₁₀ and R ₁₃₂ to _{R 135} are each independently the same as R ₁₂ in the general formula (102), provided that R ₁₁₀ and R ₁₃₂ to _{R 135} At least one of them is a single bond that bonds to another atom or other structure in the molecule of the first compound, and the plurality of R ₁₁₀ is the same or different from each other.

In the above general formulas (B110) to (B117), a group consisting of two or more adjacent R ₁₁₀ and one or more groups of R ₁₃₂ and R ₁₃₃ are combined with each other to form a substituted or unsubstituted monocycle. They form or combine with each other to form a substituted or unsubstituted condensed ring, or do not combine with each other.

In the general formulas (B118) to (B123), R ₁₁₀ is each independently the same as R ₁₂ in the general formula (102), and Xa and Xb are each independently the same as R 12 in the general formula (102). _The same _as At least one of the atoms is bonded to another atom or another structure in the molecule of the first compound, and the plurality of R ₁₁₀ is the same or different from each other.

In the above general formulas (B118) to (B123), a group consisting of two or more adjacent R _110s , a group of R ₁₄ and R ₁₅ in Xa, and a group of R ₁₄ and R ₁₅ in Xb (same as the combination of R ₁₄ and R ₁₅ in X ₁₀ ), and the combination of R ₁₆ and R ₁₇ in Xa, and the combination of _{R 16} and _{R 17} in One or more sets (synonymous with Article ₁₇ ) combine with each other to form a substituted or unsubstituted single ring, combine with each other to form a substituted or unsubstituted condensed ring, or do not combine with each other.

In the general formulas (B124) to (B125), R ₁₁₀ is each independently the same as R ₁₂ in the general formula (102), and Xa, Xb and Xc are each independently the same as in the general formula (102). has _the same meaning _as At least one of the carbon atom and the silicon atom is bonded to another atom or another structure in the molecule of the first compound, and the plurality of R ₁₁₀ is the same or different from each other.

In the above general formulas (B124) to (B125), a group consisting of two or more adjacent R _110s , a group of R ₁₄ and R ₁₅ in Xa, Xb and Xc (R ₁₄ in X ₁₀ and R ₁₅ ), and one or more sets of R ₁₆ and R ₁₇ in Xa, Xb and Xc (synonymous with R ₁₆ and _{R 17 in} They form unsubstituted single rings, combine with each other to form substituted or unsubstituted condensed rings, or do not combine with each other.

In the general formulas (A101) to (A121) and (B101) to (B125), R ₁₁₀ , R ₁₀₁ to R ₁₀₆ , R ₁₁₂ to R ₁₁₄ , R ₁₂₁ to _{R 131} and R ₁₃₂ to R ₁₃₅ are each independent. a hydrogen atom, an unsubstituted aryl group with 6 to 30 ring carbon atoms, an unsubstituted heterocyclic group with 5 to 30 ring atoms, an unsubstituted alkyl group with 1 to 30 carbon atoms, or an unsubstituted aryl group with 1 to 30 carbon atoms. It is preferably a halogenated alkyl group, and is a hydrogen atom, an unsubstituted aryl group with 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group with 5 to 14 ring atoms, an unsubstituted alkyl group with 1 to 6 carbon atoms, or an unsubstituted alkyl group. It is more preferable that it is a halogenated alkyl group having 1 to 6 carbon atoms, a hydrogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, or an unsubstituted alkyl group having 1 to 6 carbon atoms.

In the general formulas (A101) to (A121) and (B101) to (B125), R ₁₃ to R ₁₉ in Xa, Xb, Xc and X ₁₁₀ (same as R ₁₃ to R ₁₉ in X ₁₀ ) are each independently a hydrogen atom, an unsubstituted aryl group with 6 to 30 ring carbon atoms, an unsubstituted heterocyclic group with 5 to 30 ring atoms, an unsubstituted alkyl group with 1 to 30 carbon atoms, or an unsubstituted carbon number. It is preferably a halogenated alkyl group of 1 to 30 carbon atoms, and includes a hydrogen atom, an unsubstituted aryl group with 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group with 5 to 14 ring carbon atoms, and an unsubstituted alkyl group with 1 to 6 carbon atoms. , or an unsubstituted halogenated alkyl group with 1 to 6 carbon atoms, and even more preferably an unsubstituted aryl group with 6 to 14 ring-forming carbon atoms, or an unsubstituted alkyl group with 1 to 6 carbon atoms.

In this embodiment, the first compound is (I) any one of a cyano group, an amino group, a substituted or unsubstituted alkylamino group with 2 to 30 carbon atoms, and a substituted or unsubstituted arylamino group with 6 to 60 ring carbon atoms. It has at least one group, or (II) substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted indole, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted Or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene, substituted or unsubstituted silafluorene, substituted or unsubstituted triazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridine, substituted or any of unsubstituted pyridazine, substituted or unsubstituted pyrazine, substituted or unsubstituted imidazole, substituted or unsubstituted benzimidazole, substituted or unsubstituted phenanthrene, and substituted or unsubstituted triphenylene. It is preferred to have at least one monovalent or higher residue derived from one.

In this embodiment, the first compound has (III) at least one cyano group, or (IV) substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, or substituted or unsubstituted dibenzo. Thiophene, substituted or unsubstituted fluorene, substituted or unsubstituted silafluorene, substituted or unsubstituted triazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridine, and substituted or unsubstituted triazine. It is more preferable to have at least one monovalent or higher residue derived from any one of phenylene.

In this embodiment, the first compound is substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted triazine, and substituted or unsubstituted triazine. It is more preferable to have at least one monovalent or higher residue derived from any of the substituted pyrimidines.

In this embodiment, the first compound preferably has at least one monovalent or higher residue derived from substituted or unsubstituted carbazole.

In this embodiment, the first compound preferably has at least one partial structure represented by the following general formula (15).

(In the general formula (15), at least one of R ₁₅₀ to _{R 158} is a single bond bonded to another atom or other structure in the molecule of the first compound,

R ₁₅₀ ∼ R ₁₅₈ , which are not single bonds, are each independently

hydrogen atom,

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

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

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

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

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

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

A group represented by -O-(R ₉₀₄ ),

A group represented by -S-(R ₉₀₅ ),

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

A group represented by -C(=O)R ₉₀₈ ,

-The group represented by COOR ₉₀₉ ,

A group represented by -P(=O)(R ₉₁₀ )(R ₉₁₁ ),

A group represented by -Ge(R ₉₁₂ )(R ₉₁₃ )(R ₉₁₄ ),

-A group represented by B(R ₉₁₅ )(R ₉₁₆ ),

Substituted or unsubstituted aralkyl group with 7 to 50 carbon atoms,

halogen Atom,

Cyanogi,

nitro group,

A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or

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

In the general formula (15), R ₁₅₀ is a substituted or unsubstituted aryl group with 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group with 5 to 30 ring carbon atoms, or a substituted or unsubstituted aryl group with 5 to 30 ring carbon atoms. It is preferably an alkyl group with ~30 carbon atoms, or a substituted or unsubstituted halogenated alkyl group with 1 to 30 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted alkyl group with 1 to 30 carbon atoms. It is more preferable that it is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

(First compound represented by general formula (161) or (162))

In this embodiment, the first compound is also preferably a compound represented by the following general formula (161) or the following general formula (162).

(In the general formula (161), Ar ₁₆₁ is,

A substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 30 carbon atoms, or

It is a substituted or unsubstituted heterocycle with 5 to 30 ring atoms,

m1 is 1, 2, 3, 4, 5 or 6,

R ₁₆₁ is an electron donating group, and R ₁₆₁ is each bonded to an element constituting Ar ₁₆₁ ,

When m1 is 2 or more, a plurality of R ₁₆₁ are the same or different from each other,

However, Ar ₁₆₁ is not an electron-accepting aromatic hydrocarbon ring or heterocycle, and when Ar ₁₆₁ has a substituent, the substituent is not an electron acceptor,

In the general formula (162), Ar ₁₆₂ is,

A substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 30 carbon atoms, or

It is a substituted or unsubstituted heterocycle with 5 to 30 ring atoms,

n1 is 1, 2, 3, 4, 5 or 6,

R ₁₆₂ is an electron acceptor, and R ₁₆₂ each binds to an element constituting Ar ₁₆₂ ,

When n1 is 2 or more, a plurality of R ₁₆₂ are the same or different from each other,

However, Ar ₁₆₂ is not an electron-donating aromatic hydrocarbon ring or heterocycle, and when Ar ₁₆₂ has a substituent, the substituent is not an electron-donating group.)

In the general formulas (161) and (162), Ar ₁₆₁ and Ar ₁₆₂ are each independently a monovalent or higher residue derived from any one of the compounds represented by the following general formulas (A61), (A62), and (A63). It is desirable to be

(In the general formula (A63), X _D is an oxygen atom or a sulfur atom, and R _D is a hydrogen atom or a substituent.)

In the general formula (A63), when R _D is a substituent, examples of the substituent include groups such as R ₁₁ in the general formula (101).

In the present embodiment, R ₁₆₁ in the general formula (161) is 1 independently derived from any one of the compounds represented by the following general formulas (DN1) to (DN6) and (DN8) to (DN10). It is preferable that it is a residue of more than or a group represented by the following general formula (DN7).

(In the general formula (DN7), * represents a binding site with the elements constituting Ar ₁₆₁ , respectively.)

In the present embodiment, R ₁₆₂ in the general formula (162) is 1 independently derived from any one of the compounds represented by the following general formulas (AC4) to (AC18) and (AC22) to (AC23). It is preferable that it is one or more residues or one of the groups represented by the following general formulas (AC1) to (AC3), (AC19) to (AC21) and (AC24).

(In the general formula (AC1), n _A is 1, 2, or 3,

In the general formulas (AC22) to (AC23), X ₁ to X ₈ are each independently CR ₁₆₃ or a carbon atom bonded to another atom or other structure in the molecule of the first compound, provided that At least one of the _carbon atoms in _{1 to}

In the general formula ( _{AC24 )} , X _{1 to}

In the above general formulas (AC22) to (AC24), when a plurality of R ₁₆₃ is present, the plurality of R ₁₆₃ is the same as or different from each other, and at least one set of two or more adjacent R 163s among the plurality of R ₁₆₃ is present,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

R ₁₆₃ that does not form the substituted or unsubstituted monocyclic ring or does not form the substituted or unsubstituted condensed ring is each independently the same as R ₁₂ in the general formula (102),

In the general formulas (AC1) to (AC3), (AC19) to (AC21) and (AC24), * represents the binding site with the element constituting Ar ₁₆₂ , respectively.)

In this embodiment, the first compound is also preferably a compound represented by the following general formula (13).

(In the above general formula (13),

X ₁₃ is an oxygen atom, a sulfur atom, or a group represented by N-Rb,

Z ₁ to _{Z 12} are each independently a nitrogen atom or a group represented by C-Rc,

Ar ₁₄ and Ar ₁₅ are each independently

A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or

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

L ₁₄ and L ₁₅ are each independently

single bond,

A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or

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

Rb and Rc are each independently

hydrogen atom,

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

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

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

Substituted or unsubstituted aralkyl group with 7 to 50 carbon atoms,

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

A group represented by -C(=O)R ₉₀₈ ,

-The group represented by COOR ₉₀₉ ,

A group represented by -P(=O)(R ₉₁₀ )(R ₉₁₁ ),

A group represented by -Ge(R ₉₁₂ )(R ₉₁₃ )(R ₉₁₄ ),

Cyanogi,

nitro group,

A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or

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

When there are multiple Rcs, the multiple Rcs are the same or different from each other.)

In the compound represented by the general formula (13), when the group represented by -L ₁₄ -Ar ₁₄ and the group represented by -L ₁₅ -Ar ₁₅ are the same substituent, Z ₁ and Z ₁₂ , Z ₂ and Z ₁₁ , It is also preferable that Z ₃ and Z ₁₀ , Z ₄ and Z ₉ , Z ₅ and Z ₈ and Z ₆ and Z ₇ are not the same group. In this _case , in the general formula ( ₁₃ ), the structure condensed on the right side of the 5-membered ring containing ) is a compound with an asymmetric structure.

In the compound represented by the general formula (13), it is preferable that the group represented by -L ₁₄ -Ar ₁₄ and the group represented by -L ₁₅ -Ar ₁₅ are different groups. In this case, as described above, the compound represented by the general formula (13) is a compound having an asymmetric structure.

In the present embodiment, the first compound is preferably a compound represented by the following general formula (12).

(In the above general formula (12),

Ar ₁₁ and Ar ₁₂ are each independently

A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or

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

L ₁₁ and L ₁₂ are each independently

single bond,

A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or

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

L ₁₃ is,

A substituted or unsubstituted ring-forming monocyclic hydrocarbon group with 6 or less carbon atoms, or

It is a substituted or unsubstituted monocyclic heterocyclic group with 6 or less ring atoms,

m is 0, 1, 2 or 3, and the plurality of L ₁₃ are the same or different from each other,

X ₁ to X ₈ and Y ₁ to _{Y 8} are each independently N or CRa,

However, one of X ₅ to X ₈ and one of Y ₁ to _{Y 4} are a carbon atom bonded through L ₁₃ or a carbon atom bonded directly,

Ra is each independently

hydrogen atom,

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

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

halogen Atom,

A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or

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

When there are multiple Ra's, the multiple Ra's are the same or different from each other,

The compound represented by the general formula (12) satisfies one or both of (i) and (ii) below.

(i) At least one of Ar ₁₁ and Ar ₁₂ is an aryl group having 6 to 50 ring carbon atoms substituted with a cyano group, or a heterocyclic group having 5 to 50 ring atoms substituted with a cyano group.

( _ii ) At least one of X ₁ to _{X 4} and Y ₅ to _{Y 8} is CRa, and at least one of Ra in X ₁ to It is an aryl group of ~50, or a heterocyclic group of 5-50 ring atoms substituted with a cyano group.)

In the compound represented by the general formula (12), the aromatic hydrocarbon group having 6 to 50 ring carbon atoms substituted with a cyano group and the heterocyclic group having 5 to 50 ring atoms substituted with a cyano group are substituents other than the cyano group. It's okay to have more.

In the compound represented by the general formula (12), m is preferably 0, 1, or 2, and more preferably 0 or 1. In the compound represented by the general formula (12), when m is 0, one of X ₅ to X ₈ and one of Y ₁ to _{Y 4} are directly bonded through a single bond.

In the compound represented by the general formula (12), any one group selected from the group consisting of the group of X _{6 and} Y ₃ , the group of X ₆ and Y ₂ , and the group of X ₇ and Y ₃ is It is preferable that it is a bonded carbon atom or a directly bonded carbon atom.

_{When the} combination _of

(In the general formula ( ₁₂₁ ), Ar ₁₁ , Ar _{12 , L 11} , _{L 12 , L 13 , m} , are Ar ₁₁ , _{Ar 12 , L 11 , L 12} , L _{13 , m} , ₍₈ ), and the compound represented by the general formula (121) satisfies at least one of the conditions (i) and (ii) above.)

In the compound represented by the general formula (12), it is preferable that the group represented by -Ar ₁₁ -L ₁₁ and the group represented by -Ar ₁₂ -L ₁₂ are different from each other.

The monocyclic hydrocarbon group having 6 or less ring carbon atoms as L ₁₃ is preferably at least one group selected from the group consisting of, for example, phenylene group, cyclopentenylene group, cyclopentadienylene group, cyclohexylene group and cyclopentylene group, It is more preferable that it is a phenylene group.

The monocyclic heterocyclic group having 6 or less ring atoms as L ₁₃ is preferably at least one group selected from the group consisting of, for example, a pyrrolylene group, a pyrazinylene group, a pyridinylene group, a prilene group, and a thiophenylene group.

In one embodiment, the light-emitting layer may contain two or more types of first compounds having different molecular structures. By mixing compounds with different charge transport properties, the charge balance in the light-emitting layer is improved, and improvement in luminous efficiency is expected. Additionally, when two or more types of first compounds (host materials) form an exciplex, the excitation energy decreases, making lower voltage driving possible than when one type of host material is contained in the light-emitting layer.

(Method for producing first compound)

The first compound can be prepared by a known method. Additionally, the first compound can also be produced by using known substitution reactions and raw materials tailored to the target according to a known method.

(Specific example of the first compound)

Specific examples of the first compound of this embodiment include the following compounds. However, the present invention is not limited to specific examples of these compounds.

[Increasing material]

In this embodiment, the sensitizing material is one or more compounds selected from the group consisting of phosphorescent metal complexes and delayed fluorescent compounds. In this specification, the compound used as a sensitizing material may be called a second compound.

(phosphorescent metal complex)

In this embodiment, it is preferable that the phosphorescent metal complex contains a heavy metal atom.

In this embodiment, the phosphorescent metal complex is platinum (Pt), iridium (Ir), osmium (Os), ruthenium (Ru), rhodium (Rh), palladium (Pd), copper (Cu), and silver (Ag). , gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm). desirable.

In this embodiment, the phosphorescent metal complex is preferably a compound represented by the following general formula (21).

M(L ₁ ) _n1 (L ₂ ) _n2 … (21)

(In the general formulas (21), (211), (212), (213),

M is a transition metal selected from the group consisting of a first transition metal, a second transition metal, and a third transition metal,

L ₁ is at least one type of ligand selected from the group consisting of a ligand represented by the general formula (211), a ligand represented by the general formula (212), and a ligand represented by the general formula (213),

n1 is 1, 2 or 3,

L ₂ is at least one type of ligand selected from the group consisting of monodentate ligands, bidentate ligands, and tridentate ligands,

n2 is 0, 1, 2, 3 or 4,

The CY ₁ ring, CY ₂ ring, CY ₃ ring, and CY ₄ ring are each independently selected from the group consisting of a carbocyclic group having 5 to 30 ring carbon atoms and a heterocyclic group having 1 to 30 ring carbon atoms,

Y ₁ to _{Y 4} are each independently

single bond,

double bond,

A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms,

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

*a-O-*b,

*a-S-*b,

*a-C(=O)-*b,

*a-S(=O)-*b,

*aC(R ₅ )(R ₆ )-*b,

*aC(R ₅ )=C(R ₆ )-*b,

*aC(R ₅ )=*b,

*a-Si(R ₅ )(R ₆ )-*b,

*aB(R ₅ )-*b;

*aN(R ₅ )-*b, and

selected from the group consisting of *aP(R ₅ )-*b,

a1, a2 and a3 are each independently 1, 2 or 3,

a4 is 0, 1, 2, or 3, and when a4 is 0, the CY ₁ ring and the CY ₄ ring are not connected to each other,

T ₁ , T ₂ , T ₃ and T ₄ are each independently

chemical bond,

*a-O-*b,

*a-S-*b,

*aB(R ₇ )-*b;

*aN(R ₇ )-*b;

*aP(R ₇ )-*b;

*aC(R ₇ )(R ₈ )-*b,

*a-Si(R ₇ )(R ₈ )-*b,

*a-Ge(R ₇ )(R ₈ )-*b,

*a-C(=O)-*b and

selected from the group consisting of *a-C(=S)-*b,

*a and *b are each independently bonding positions with adjacent atoms,

*1, *2, *3 and *4 are binding sites with M,

R ₁ to R ₈ are each independently

hydrogen atom,

halogen Atom,

Cyanogi,

nitro group,

amidino group,

hydrazino group,

Hydrazonogi,

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

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

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

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

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

A substituted or unsubstituted ring-forming cycloalkenyl group having 3 to 50 carbon atoms,

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

A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms,

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

Substituted or unsubstituted monovalent non-aromatic condensed polycyclic group,

Substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group,

-A group represented by Si(R ₂₅₁ )(R ₂₅₂ )(R ₂₅₃ ),

A group represented by -O-(R ₂₅₄ ),

A group represented by -S-(R ₂₅₅ ),

A group represented by -N(R ₂₅₆ )(R ₂₅₇ ),

A group represented by -C(=O)R ₂₅₈ ,

A group represented by -C(=O)(OR ₂₅₉ ),

A group represented by -S(=O) ₂ (OR ₂₆₀ ),

A group represented by -OP(=O)(OR ₂₆₁ )(OR ₂₆₂ ),

-A group represented by C(R ₂₆₃ )(R ₂₆₄ )(R ₂₆₅ ),

-A group represented by B(R ₂₆₆ )(R ₂₆₇ ),

-A group represented by P(R ₂₆₈ )(R ₂₆₉ ),

A group represented by -S(=O)(R ₂₇₀ ),

A group represented by -S(=O) ₂ (R ₂₇₁ ),

A group represented by -P(=O)(R ₂₇₂ )(R ₂₇₃ ), and

-P(=S)(R ₂₇₄ )(R ₂₇₅ ) is selected from the group represented by,

One or more sets of groups consisting of two or more adjacent R ₁ to R ₈ ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

One or more sets of adjacent two or more _of R ₁ to R 8 and Y ₁ to _{Y 4} ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

b1, b2, b3 and b4 are each independently

is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10,

R ₂₅₁ to R ₂₇₅ are each independently

hydrogen atom,

halogen Atom,

A group represented by -O-(R ₂₇₆ ),

A group represented by -N(R ₂₇₇ )(R ₂₇₈ ),

Cyanogi,

nitro group,

amidino group,

hydrazino group,

Hydrazonogi,

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

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

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

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

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

A substituted or unsubstituted ring-forming cycloalkenyl group having 3 to 50 carbon atoms,

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

A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms,

A ring-forming aryl group with 6 to 50 carbon atoms substituted with a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms,

An aryl group having 6 to 50 ring carbon atoms substituted with a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

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

Substituted or unsubstituted monovalent non-aromatic condensed polycyclic group,

Substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group,

selected from the group consisting of biphenylyl group and terphenylyl group,

R ₂₇₆ to R ₂₇₈ are each independently

hydrogen atom,

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

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

A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or

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

In this specification, a carbocyclic group having 5 to 30 ring carbon atoms means a monocyclic or polycyclic group having 5 to 30 carbon atoms that contains only carbon as a ring forming atom. The carbocyclic ring having 5 to 30 ring carbon atoms may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. The carbon ring group having 5 to 30 ring carbon atoms may be a ring such as benzene, a monovalent group such as a phenyl group, or a divalent group such as a phenylene group. Alternatively, depending on the number of substituents connected to the carbocyclic ring having 5 to 30 ring carbon atoms, various modifications are possible so that the carbocyclic ring having 5 to 30 ring carbon atoms becomes a trivalent group or a tetravalent group.

In this specification, a heterocyclic group having 1 to 30 ring carbon atoms has the same structure as a carbon ring having 5 to 30 ring carbon atoms, but as ring forming atoms, in addition to carbon (the carbon number may be 1 to 30), N ( refers to a group containing at least one hetero atom selected from carbon atom), O (oxygen atom), Si (silicon atom), P (phosphorus atom), and S (sulfur atom).

In the present specification, the heterocycloalkyl group having 3 to 50 ring atoms is one of 3 to 50 ring atoms containing at least one hetero atom selected from N, O, Si, P and S as a ring forming atom. means a monocyclic group, and specific examples thereof include 1,2,3,4-oxatriazolidinyl group, tetrahydrofuranyl group, and tetrahydrothiophenyl group. In the present specification, a heterocycloalkylene group having 3 to 50 ring atoms means a divalent group having the same structure as a heterocycloalkyl group having 3 to 50 ring atoms.

In the present specification, a cycloalkenyl group having 3 to 50 ring carbon atoms refers to a monovalent monocyclic group having 3 to 50 ring carbon atoms and has at least one double bond in the ring, but does not have aromaticity. And specific examples include cyclopentenyl group, cyclohexenyl group, and cycloheptenyl group. In this specification, a cycloalkenylene group having 3 to 50 ring carbon atoms refers to a divalent group having the same structure as a cycloalkenyl group having 3 to 50 ring carbon atoms.

In the present specification, a heterocycloalkenyl group having 3 to 50 ring forming atoms is a group having 3 to 50 ring forming atoms containing at least one hetero atom selected from N, O, Si, P and S as a ring forming atom. It is a monovalent monocyclic group and has at least one double bond in the ring. Specific examples of heterocycloalkenyl groups having 3 to 50 ring atoms include 4,5-dihydro-1,2,3,4-oxatriazolyl group, 2,3-dihydrofuranyl group, and 2,3- Dihydrothiophenyl group, etc. are included. In this specification, a heterocycloalkenylene group having 3 to 50 ring atoms means a divalent group having the same structure as a heterocycloalkenyl group having 3 to 50 ring atoms.

According to one embodiment, among the compounds represented by the general formula (21), a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms is preferably 3 to 10 ring carbon atoms, and a substituted or unsubstituted cycloalkyl group has 3 to 10 ring carbon atoms. A heterocycloalkyl group having 3 to 50 ring atoms preferably has 3 to 10 ring atoms, and a substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms preferably has 3 to 10 ring carbon atoms. And, a substituted or unsubstituted heterocycloalkenyl group with 3 to 50 ring atoms preferably has 3 to 10 ring atoms.

In the present specification, a monovalent non-aromatic condensed polycyclic group is a monovalent group (e.g. It means having 8 to 60 carbon atoms). In the present specification, a divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as a monovalent non-aromatic condensed polycyclic group.

In the present specification, a monovalent non-aromatic heterocondensed polycyclic group has two or more rings condensed with each other, and includes at least one hetero atom selected from N, O, Si, P and S in addition to carbon as a ring forming atom. , means a monovalent group (for example, having 1 to 60 carbon atoms) in which the entire molecule is non-aromatic. In the present specification, a divalent non-aromatic hetero-condensed polycyclic group refers to a divalent group having the same structure as a monovalent non-aromatic hetero-condensed polycyclic group.

In this specification, “biphenylyl group” means “phenyl group substituted with a phenyl group.” The “biphenylyl group” belongs to the “substituted phenyl group” whose substituent is “an aryl group having 6 to 50 ring carbon atoms.”

In this specification, “terphenylyl group” means “phenyl group substituted with biphenylyl group.” “Terphenylyl group” belongs to the “substituted phenyl group” in which the substituent is “an aryl group having 6 to 50 ring carbon atoms substituted with an aryl group having 6 to 50 ring carbon atoms.”

In the compound represented by the general formula (21), the chemical bonds as T ₁ , T ₂ , T ₃ and T ₄ are preferably single bonds.

In the compound represented by the general formula (21), M is platinum (Pt), iridium (Ir), osmium (Os), ruthenium (Ru), rhodium (Rh), palladium (Pd), copper (Cu), At least one metal atom selected from the group consisting of silver (Ag), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm). It is preferable that it is platinum (Pt) or iridium (Ir).

According to one embodiment, in the compound represented by the general formula (21), the CY ₁ ring to the CY ₄ ring are each independently selected from benzene, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, chrysene, and cyclo Pentadiene, 1,2,3,4-tetrahydronaphthalene, carbene, thiophene, furan, selenophen, indole, benzoborole, benzophosphopol, indene, benzosilol, benzogelmol, benzothiophene, Benzoselenophen, benzofuran, carbazole, dibenzoborole, dibenzophosphole, fluorene, dibenzosilol, dibenzogelmol, dibenzothiophene, dibenzoselenophen, dibenzofuran, dibenzothiophene 5- Oxide, 9H-fluoren-9-one, dibenzothiophene-5,5-dioxide, azaindole, azabenzoborole, azabenzophosphopol, azaindene, azabenzosilol, azabenzogelmol, azabenzothiophene , azabenzoselenophen, azabenzofuran, azacarbazole, azadibenzoborole, azadibenzophosphole, azafluorene, azadibenzosilol, azadibenzogelmol, azadibenzothiophene, azadibenzoselenophen , azadibenzofuran, azadibenzothiophene 5-oxide, aza-9H-fluoren-9-one, azadibenzothiophene 5,5-dioxide, pyridine, pyrimidine, pyrazine, pyridazine, triazine, Quinoline, isoquinoline, quinoxaline, quinazoline, phenanthroline, pyrrole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, thiadiazole, benzopyra Sol, benzoimidazole, benzoxazole, benzothiazole, benzooxadiazole, benzothiadiazole, 5,6,7,8-tetrahydroisoquinoline and 5,6,7,8-tetrahydroquinoline You may be selected from the military.

According to one embodiment, at least one of the CY ₁ ring and the CY ₂ ring in the general formula (211), at least one of the CY ₁ ring to the CY ₃ ring in the general formula (212), and CY in the general formula (213) At least one of rings ₁ to CY ₄ may be carbene.

According to one embodiment, Y ₁ to Y ₄ in general formulas (211) to (213) are each independently a single bond, a double bond, *aO-*b, *aS-*b, *aC(R ₅ ) At least one selected from the group consisting of (R ₆ )-*b and *aN(R ₅ )-*b may be used.

According to one embodiment, at least one of R ₁ and R ₂ in General Formula (211), at least one of R ₁ to R ₃ in General Formula (212), and at least one of R ₁ to _{R 4} in General Formula (213) may also be an electron donating group.

For example, the electron donating group may be an iso-propyl group, a tert-butyl group, or a substituent selected from the group consisting of the following general formulas (10-1) to (10-61).

In the above general formulas (10-1) to (10-61), * is a bonding position with an adjacent atom.

In this specification, a heavy hydrogen atom is denoted as D in the chemical formula, and a light hydrogen atom is denoted as H or the description is omitted. In this specification, in chemical formulas, a methyl group may be denoted as Me, a phenyl group may be denoted as Ph, an isopropyl group may be denoted as i-Pr, and a t-butyl group may be denoted as t-Bu.

According to one embodiment, at least one of R ₁ and R ₂ in the general formula (211) is a substituent other than hydrogen, and/or Y ₁ is *aN(R ₅ )-*b, and R ₅ is substituted An aryl group having 6 to 50 ring carbon atoms may also be used.

According to one embodiment, at least one of R ₁ to _{R 3} in the general formula (212) is a substituent other than hydrogen, and/or at least one of Y ₁ and Y ₂ is *aN(R ₅ )-*b and R ₅ may be a substituted aryl group having 6 to 50 ring carbon atoms.

According to one embodiment, at least one of R ₁ to _{R 4} in the general formula (213) is a substituent other than hydrogen, and/or at least one of Y ₁ to Y ₄ is *aN(R ₅ )-*b and R ₅ may be a substituted aryl group having 6 to 50 ring carbon atoms.

In this embodiment, the compound represented by the general formula (21) is preferably a compound selected from the group consisting of compounds represented by the following general formulas (214) and (215).

(In the above general formulas (214) and (215), M, L ₂ , n1, n2, CY ₁ ring to CY ₄ ring, Y ₁ to Y ₃ , a1 to a3, T ₁ to T ₄ , R ₁ to R ₄ and b ₁ to b ₄ are each the same as described above.)

According to one embodiment, at least one of the CY ₁ ring and the CY ₂ ring in the general formula (214) and at least one of the CY ₁ ring to the _{CY 4} ring in the general formula (215) may be carbene.

For example, either the CY ₁ ring or the CY ₄ ring in general formula (215) may be a carbene.

In the present embodiment, the compound represented by the general formula (21) is preferably at least one compound selected from the group consisting of compounds represented by the following general formulas (215A) and (215B).

(In the general formulas (215A) and (215B),

M ₁ is Pt,

M ₂ is selected from a first transition metal, a second transition metal and a third transition metal,

CY ₁₂ ring, CY ₁₃ ring, CY ₁₄ ring, CY ₂₂ ring, CY ₂₃ ring and CY ₂₄ ring are each independently a carbocyclic group having 5 to 30 ring carbon atoms and a heterocyclic group having 1 to 30 ring carbon atoms. selected,

A ₁₁ , A ₁₂ , A ₂₁ and A ₂₂ are each independently N (nitrogen atom) or P (phosphorus atom),

X ₁₁ , X ₁₂ , X ₁₃ , X ₂₁ , X ₂₂ and X ₂₃ are each independently N (nitrogen atom) or C (carbon atom),

Y ₁₁ to _{Y 13} each independently represent a single bond, a double bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, *aO -*b, *aS-*b, *aC(=O)-*b, *aS(=O)-*b, *aC(R ₁₅ )(R ₁₆ )-*b, *aC(R ₁₅ ) =C(R ₁₆ )-*b, *aC(R ₁₅ )=*b, *a-Si(R ₁₅ )(R ₁₆ )-*b, *aB(R ₁₅ )-*b, *aN(R ₁₅ )-*b, and *aP(R ₁₅ )-*b,

Y ₂₁ to _{Y 23} are each independently a single bond, a double bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, *aO -*b, *aS-*b, *aC(=O)-*b, *aS(=O)-*b, *aC(R ₂₅ )(R ₂₆ )-*b, *aC(R ₂₅ ) =C(R ₂₆ )-*b, *aC(R ₂₅ )=*b, *a-Si(R ₂₅ )(R ₂₆ )-*b, *aB(R ₂₅ )-*b, *aN(R ₂₅ )-*b, and *aP(R ₂₅ )-*b,

a11, a12 and a13 are each independently 1, 2 or 3,

a21, a22 and a23 are each independently 1, 2 or 3,

T ₁₁ , T ₁₂ , T ₁₃ and T ₁₄ are each independently a chemical bond, *aO-*b, *aS-*b, *aB(R ₁₇ )-*b, *aN(R ₁₇ )-*b, *aP(R ₁₇ )-*b, *aC(R ₁₇ )(R ₁₈ )-*b, *a-Si(R ₁₇ )(R ₁₈ )-*b, *a-Ge(R ₁₇ )(R ₁₈ )-*b, *aC(=O)-*b, and *aC(=S)-*b,

T ₂₁ , T ₂₂ , T ₂₃ and T ₂₄ are independently of each other chemical bonds, *aO-*b, *aS-*b, *aB(R ₂₇ )-*b, *aN(R ₂₇ )-*b, *aP(R ₂₇ )-*b, *aC(R ₂₇ )(R ₂₈ )-*b, *a-Si(R ₂₇ )(R ₂₈ )-*b, *a-Ge(R ₂₇ )(R ₂₈ )-*b, *aC(=O)-*b, and *aC(=S)-*b,

*a and *b are each independently bonding positions with adjacent atoms,

R _11a , R _11b , R _11c , R ₁₂ to _{R 18} , R _21a , R _21b , R _21c and R ₂₂ to _{R 28} are each independently hydrogen atom, halogen atom, cyano group, nitro group, amidino group, hydra Zino group, hydrazono group, substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 50 carbon atoms, substituted or unsubstituted alkynyl group with 2 to 50 carbon atoms, substituted or unsubstituted Ring-forming cycloalkyl group with 3 to 50 carbon atoms, substituted or unsubstituted ring-forming heterocycloalkyl group with 3 to 50 carbon atoms, substituted or unsubstituted ring-forming cycloalkenyl group with 3 to 50 carbon atoms, substituted or unsubstituted ring-forming group. Heterocycloalkenyl group with 3 to 50 atoms, substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, substituted or unsubstituted ring-forming heterocyclic group with 5 to 50 atoms, substituted or unsubstituted monovalent ratio Aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, group represented by -Si(R ₂₅₁ )(R ₂₅₂ )(R ₂₅₃ ), group represented by -O-(R ₂₅₄ ), A group represented by -S-(R ₂₅₅ ), a group represented by -N(R ₂₅₆ )(R ₂₅₇ ), a group represented by -C(=O)R ₂₅₈ , -C(=O)(OR ₂₅₉ ) A group represented by -S(=O) ₂ (OR ₂₆₀ ), a group represented by -OP(=O)(OR ₂₆₁ )(OR ₂₆₂ ), -C(R ₂₆₃ )(R ₂₆₄ ) A group represented by (R ₂₆₅ ), a group represented by -B(R ₂₆₆ )(R ₂₆₇ ), a group represented by -P(R ₂₆₈ )(R ₂₆₉ ), a group represented by -S(=O)(R ₂₇₀ ) A group represented by -S(=O) ₂ (R ₂₇₁ ), a group represented by -P(=O)(R ₂₇₂ )(R ₂₇₃ ), and -P(=S)(R ₂₇₄ ). (R ₂₇₅ ) is selected from the group represented by,

One or more sets of adjacent two or more of R _11a , R _11b , R _11c and R ₁₂ to R ₁₈ ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

One or more sets of adjacent two or more of R _21a , R _21b , R _21c and R ₂₂ to R ₂₈ ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

b12, b13, b14, b22, b23 and b24 are each independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10,

R ₂₅₁ to _{R 275} are the same as R ₂₅₁ to R ₂₇₅ in the general formulas (21), (211), (212), and (213) above.)

According to one embodiment, R ₂₅₁ to R ₂₇₅ are each independently

hydrogen atom,

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

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

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

It may be selected from the group consisting of substituted or unsubstituted heterocyclic groups having 5 to 50 ring atoms.

When a plurality of R ₂₅₁ to _{R 275} each exist, a plurality of R ₂₅₁ , a plurality of R ₂₅₂ , a plurality of R ₂₅₃ , a plurality of R ₂₅₄ , a plurality of R ₂₅₅ , a plurality of R ₂₅₆ , a plurality of R ₂₅₇ , a plurality of R ₂₅₈ , plurality of R ₂₅₉ , plurality of R ₂₆₀ , plurality of R ₂₆₁ , plurality of R ₂₆₂ , plurality of R ₂₆₃ , plurality of R ₂₆₄ , plurality of R ₂₆₅ , plurality of R ₂₆₆ , plurality of R ₂₆₇ , plurality of R ₂₆₈ , a plurality of R ₂₆₉ , a plurality of R ₂₇₀ , a plurality of R ₂₇₁ , a plurality of R ₂₇₂ , a plurality of R ₂₇₃ , a plurality of R ₂₇₄ and a plurality of R ₂₇₅ are each the same as or different from each other.

According to one embodiment, one or more of the group of R _11b and R _11c in the general formula (215A) and the group of R _21b and R _21c in the general formula (215B) are combined with each other to form at least one may be substituted or unsubstituted with R _a and form a benzene ring, naphthalene ring, pyridine ring, pyrimidine ring or pyrazine ring, and R _a is the same as R _11a in the general formula (215A), When a plurality of R _a is present, the plurality of R _a is the same as or different from each other.

According to one embodiment, at least one of R _11a , R _11b , R _11c and R ₁₄ in the general formula (215A) may be an electron donating group.

For example, at least one of R _11a and R ₁₄ in the general formula (215A) may be an electron donating group. According to one embodiment, at least one of R _11a and R ₁₄ in the general formula (215A) is an iso-propyl group, a tert-butyl group, and a group represented by the general formulas (10-1) to (10-61). An electron donating group selected from the group consisting of groups may also be used.

According to one embodiment, at least one of R ₂₂ and R ₂₃ in the general formula (215B) is a substituent other than hydrogen, and/or Y ₂₃ is *aN(R ₂₅ )-*b, and R ₂₅ is A substituted aryl group having 6 to 50 ring carbon atoms may also be used.

For example, at least one of R ₂₂ and R ₂₃ is a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group with 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group with 2 to 50 carbon atoms, or a substituted or an unsubstituted cycloalkyl group with 3 to 50 ring carbon atoms, a substituted or unsubstituted heterocycloalkyl group with 3 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkenyl group with 3 to 50 ring carbon atoms, substituted or unsubstituted. Substituted ring-forming heterocycloalkenyl group with 3 to 50 carbon atoms, substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic group with 5 to 50 ring-forming atoms, substituted or unsubstituted. selected from among a monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, a group represented by -O-(R ₂₅₄ ), and a group represented by -S-(R ₂₅₅ ), Additionally, Y ₂₃ may be *aN(R ₂₅ )-*b, and R ₂₅ may be a substituted aryl group having 6 to 50 ring carbon atoms.

For example, at least one of R ₂₂ and R ₂₃ is an alkyl group of 1 to 50 carbon atoms, an alkenyl group of 2 to 50 carbon atoms, an alkynyl group of 2 to 50 carbon atoms, or a cyclo carbon number of 3 to 50 ring carbon atoms, substituted with at least one deuterium. Alkyl group, heterocycloalkyl group with 3 to 50 ring atoms, cycloalkenyl group with 3 to 50 ring carbon atoms, heterocycloalkenyl group with 3 to 50 ring carbon atoms, aryl group with 6 to 50 ring carbon atoms, ring forming Among heterocyclic groups having 5 to 50 atoms, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic heterocondensed polycyclic groups, groups represented by -O-(R ₂₅₄ ) and groups represented by -S-(R ₂₅₅ ) selected, and/or Y ₂₃ may be *aN(R ₂₅ )-*b, and R ₂₅ may be an aryl group having 6 to 50 ring carbon atoms substituted with at least one deuterium.

As another example, at least one of R ₂₂ and R ₂₃ is an electron donating group selected from the group consisting of iso-propyl group, tert-butyl group and groups represented by the general formulas (10-1) to (10-61), In addition,/or Y ₂₃ is *aN(R ₂₅ )-*b, and R ₂₅ is a group consisting of an iso-propyl group, a tert-butyl group, and a group represented by the above general formulas (10-1) to (10-61) It may be an electron donating group selected from .

According to one embodiment, at least one of R _11a , R _11b , R _11c and R ₁₄ in the general formula (215A) is an electron donating group, and at least one of R ₂₂ and R ₂₃ in the general formula (215B) is a substituent other than hydrogen, and/or Y ₂₃ may be *aN(R ₂₅ )-*b, and R ₂₅ may be a substituted aryl group having 6 to 50 ring carbon atoms.

In the present embodiment, the compound represented by the general formula (21) is preferably at least one compound selected from the group consisting of compounds represented by the following general formulas (215C) and (215D).

(In the above general formulas (215C) and (215D),

Z ₁₁ is C(R _12a ) or N,

Z ₁₂ is C(R _12b ) or N,

Z ₁₃ is C(R _12c ) or N,

Z ₁₄ is C(R _13a ) or N,

Z ₁₅ is C(R _13b ) or N,

Z ₁₆ is C(R _13c ) or N,

Z ₁₇ is C(R _14a ) or N,

Z ₁₈ is C(R _14b ) or N,

Z ₁₉ is C(R _14c ) or N,

Z ₂₀ is C(R _14d ) or N,

Z ₃₁ is C(R _15a ) or N,

Z ₃₂ is C(R _15b ) or N,

Z ₃₃ is C(R _15c ) or N,

Z ₃₄ is C(R _15d ) or N,

R _12a , R _12b and R _12c are each independently the same as R ₁₂ in the general formula (215A),

R _13a , R _13b and R _13c are each independently the same as R ₁₃ in the general formula (215A),

R _14a , R _14b , R _14c and R _14d are each independently the same as R ₁₄ in the general formula (215A),

R _15a , R _15b , R _15c and R _15d are each independently the same as R ₁₅ in the general formula (215A),

_{M 1 , A 11 , A 12 , X 11 to (} Synonymous with _{A 11 , A 12 , X 11 ∼}

According to one embodiment, Z ₁₈ in the general formulas (215C) and (215D) is C(R _14b ), and at least one of R _11a to R _11c and R _14b may be an electron donating group. For example, in the general formulas (215C) and (215D), Z ₁₈ is C(R _14b ), and at least one of R _11a and R _14b may be an electron donating group.

According to one embodiment, Z ₁₈ in the general formulas (215C) and (215D) is C(R _14b ), and at least one of R _11a and R _14b is an iso-propyl group, a tert-butyl group, and the general formula An electron donating group selected from the group consisting of groups represented by (10-1) to (10-61) may be used.

In this embodiment, the compound represented by the general formula (21) is also preferably a compound represented by the following general formula (215E).

(In the above general formula (215E),

Z ₂₁ is C(R _22a ) or N, Z ₂₂ is C(R _22b ) or N, Z ₂₃ is C(R _22c ) or N, Z ₂₄ is C(R _23a ) or N, Z ₂₅ is C(R _23b ) or N, Z ₂₇ is C(R _24a ) or N, Z ₂₈ is C(R _24b ) or N, Z ₂₉ is C(R _24c ) or N, Z ₃₀ is C (R _24d ) or N, Z ₄₁ is C(R _25a ) or N, Z ₄₂ is C(R _25b ) or N, Z ₄₃ is C(R _25c ) or N, Z ₄₄ is C(R _25d ) or N,

R _22a , R _22b and R _22c are each independently the same as R ₂₂ in the general formula (215B),

R _23a and R _23b are each independently the same as R ₂₃ in the general formula (215B),

R _24a , R _24b , R _24c and R _24d are each independently the same as R ₂₄ in the general formula (215B),

R _25a , R _25b , R _25c and R _25d are each independently the same as R ₂₅ in the general formula (215B),

_{M 2 , A 21 , A 22 , X 21 to (} Synonymous _with A _{21 , A 22 , X 21 ∼}

According to one embodiment, in the general formula (215E), M ₂ may be Pt.

According to one embodiment, in the general formula (215E), Z ₂₂ is C(R _22b ), Z ₄₂ is C(R _25b ), and at least one of R _22b and R _25b may be a substituent other than hydrogen. . For example, at least one of R _22b and R _25b is a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group with 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group with 2 to 50 carbon atoms, or a substituted or an unsubstituted cycloalkyl group with 3 to 50 ring carbon atoms, a substituted or unsubstituted heterocycloalkyl group with 3 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkenyl group with 3 to 50 ring carbon atoms, substituted or unsubstituted. Substituted ring-forming heterocycloalkenyl group with 3 to 50 carbon atoms, substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic group with 5 to 50 ring-forming atoms, substituted or unsubstituted. may be selected from a monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, a group represented by -O-(R ₂₅₄ ), and a group represented by -S-(R ₂₅₅ ). .

According to one embodiment, in the general formula (215E), Z ₂₂ is C(R _22b ), Z ₄₂ is C(R _25b ), and at least one of R _22b and R _25b is comprised of at least one deuterium. Substituted, alkyl group having 1 to 50 carbon atoms, alkenyl group having 2 to 50 carbon atoms, alkynyl group having 2 to 50 carbon atoms, cycloalkyl group having 3 to 50 ring forming carbon atoms, heterocycloalkyl group having 3 to 50 ring forming atoms, ring forming. Cycloalkenyl group with 3 to 50 carbon atoms, heterocycloalkenyl group with 3 to 50 ring atoms, aryl group with 6 to 50 ring carbon atoms, heterocyclic group with 5 to 50 ring atoms, monovalent non-aromatic condensed polycyclic group. , a monovalent non-aromatic heterocondensed polycyclic group, a group represented by -O-(R ₂₅₄ ), and a group represented by -S-(R ₂₅₅ ).

According to one embodiment, in the general formula (215E), Z ₂₂ is C(R _22b ), Z ₄₂ is C(R _25b ), and at least one of R _22b and R _25b is an iso-propyl group, tert. -An electron donating group selected from the group consisting of a butyl group and groups represented by the above general formulas (10-1) to (10-61) may be used.

In the compound represented by the general formula (21), the chemical bonds at T ₁₁ , T ₁₂ , T ₁₃ , T ₁₄ , T ₂₁ , T ₂₂ , T ₂₃ and T ₂₄ are preferably single bonds.

(Specific examples of phosphorescent metal complex)

Specific examples of the phosphorescent metal complex of the present embodiment include the following compounds. However, the present invention is not limited to specific examples of these compounds.

(Delayed fluorescent compound)

In this embodiment, the delayed fluorescent compound is not a phosphorescent metal complex. In this embodiment, it is preferable that the delayed fluorescent compound is not a metal complex.

In this embodiment, the delayed fluorescent compound is preferably a compound represented by the following general formula (H1).

(In the above general formula (H1),

A _H has the following general formulas (a-1), (a-2), (a-3), (a-4), (a-5), (a-6), (a-7) and (a) -8) is a group having at least one partial structure selected from the group consisting of,

D _H is a group represented by the following general formula (221), (222) or (223),

L _H is,

single bond,

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

It is a substituted or unsubstituted heterocycle with 5 to 50 ring atoms,

m is 1, 2, 3, 4 or 5, and the plurality of A _H is the same or different from each other,

n is 1, 2, 3, 4 or 5, and the plurality of D _H are the same or different from each other.)

(In the general formulas (a-1) to (a-8), * each independently represents a bonding position with another atom in the molecule of the delayed fluorescent compound.)

(At least one set of two or more adjacent R ₂₁ to R ₂₈ in the general formula (221) above,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

One or more groups consisting of two or more adjacent R ₂₂₁ to R ₂₂₈ in the general formula (222) above,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

One or more groups consisting of two or more adjacent R ₂₃₁ to R ₂₃₈ in the general formula (223) above,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

R ₂₁ to _{R 28} that do not form a substituted or unsubstituted monocyclic ring in the general formula (221) and do not form a substituted or unsubstituted condensed ring, and are substituted or unsubstituted in the general formula (222) R ₂₂₁ to _{R 228} , which does not form a monocycle and does not form a substituted or unsubstituted condensed ring, and which does not form a substituted or unsubstituted monocycle in the general formula (223) and does not form a substituted or unsubstituted ring R ₂₃₁ to R ₂₃₈ that do not form a condensed ring are each independently

hydrogen atom,

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

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

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

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

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

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

A group represented by -O-(R ₉₀₄ ),

A group represented by -S-(R ₉₀₅ ),

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

Substituted or unsubstituted aralkyl group with 7 to 50 carbon atoms,

A group represented by -C(=O)R ₉₀₈ ,

-The group represented by COOR ₉₀₉ ,

halogen Atom,

Cyanogi,

nitro group,

A group represented by -P(=O)(R ₉₃₁ )(R ₉₃₂ ),

A group represented by -Ge(R ₉₃₃ )(R ₉₃₄ )(R ₉₃₅ ),

-A group represented by B(R ₉₃₆ )(R ₉₃₇ ),

A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or

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

In the general formula (222) and the general formula (223),

Ring A, Ring B, and Ring C are each independently any one ring structure selected from the group consisting of ring structures represented by the following general formulas (224) and (225),

Ring A, Ring B and Ring C are condensed with adjacent rings at any position,

p, px and py are each independently 1, 2, 3 or 4,

When p is 2, 3 or 4, the plurality of rings A are the same or different from each other,

When px is 2, 3 or 4, the plurality of rings B are the same or different from each other,

When py is 2, 3 or 4, the plurality of rings C are the same or different from each other,

* in the general formulas (221) to (223) indicates the bonding position with L _H. )

(In the above general formula (224),

r is 0, 2 or 4,

A group consisting of a plurality of R ₂₉ ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

In the general formula (225), X _A is a sulfur atom, an oxygen atom, or C(R ₂₉₁ )(R ₂₉₂ ),

A composition consisting of R ₂₉₁ and R ₂₉₂ ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

R ₂₉ , R ₂₉₁ and R ₂₉₂ , which do not form a substituted or unsubstituted single ring and do not form a substituted or unsubstituted condensed ring, each independently

hydrogen atom,

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

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

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

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

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

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

A group represented by -O-(R ₉₀₄ ),

A group represented by -S-(R ₉₀₅ ),

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

Substituted or unsubstituted aralkyl group with 7 to 50 carbon atoms,

-C(=O) A group represented by R ₉₀₈ ,

-The group represented by COOR ₉₀₉ ,

halogen Atom,

Cyanogi,

nitro group,

A group represented by -P(=O)(R ₉₃₁ )(R ₉₃₂ ),

A group represented by -Ge(R ₉₃₃ )(R ₉₃₄ )(R ₉₃₅ ),

-A group represented by B(R ₉₃₆ )(R ₉₃₇ ),

A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or

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

A plurality of R ₂₉ are the same or different from each other,

A plurality of R ₂₉₁ are the same or different from each other,

A plurality of R ₂₉₂ are the same or different from each other,

A plurality of X _A are the same or different from each other.)

(Among the delayed fluorescent compounds, R ₉₀₁ , R ₉₀₂ , R ₉₀₃ , R 904, R ₉₀₅ , R ₉₀₆ , R ₉₀₇ , R ₉₀₈ , R ₉₀₉ , R ₉₃₁ , R ₉₃₂ , R ₉₃₃ , _{R 934 ,} R ₉₃₅ , R ₉₃₆ and R ₉₃₇ , each independently

hydrogen atom,

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

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

A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or

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

When there is a plurality of R ₉₀₁ , the plurality of R ₉₀₁ are the same or different from each other,

When there is a plurality of R ₉₀₂ , the plurality of R ₉₀₂ are the same or different from each other,

When there is a plurality of R ₉₀₃ , the plurality of R ₉₀₃ are the same or different from each other,

When there is a plurality of R ₉₀₄ , the plurality of R ₉₀₄ are the same or different from each other,

When there is a plurality of R ₉₀₅ , the plurality of R ₉₀₅ are the same or different from each other,

When there is a plurality of R ₉₀₆ , the plurality of R ₉₀₆ are the same or different from each other,

When there is a plurality of R ₉₀₇ , the plurality of R ₉₀₇ are the same or different from each other,

When there is a plurality of R ₉₀₈ , the plurality of R ₉₀₈ are the same or different from each other,

When there is a plurality of R ₉₀₉ , the plurality of R ₉₀₉ are the same or different from each other,

When there is a plurality of R ₉₃₁ , the plurality of R ₉₃₁ are the same or different from each other,

When there is a plurality of R ₉₃₂ , the plurality of R ₉₃₂ are the same or different from each other,

When there is a plurality of R ₉₃₃ , the plurality of R ₉₃₃ are the same or different from each other,

When there is a plurality of R ₉₃₄ , the plurality of R ₉₃₄ are the same or different from each other,

When there is a plurality of R ₉₃₅ , the plurality of R ₉₃₅ are the same or different from each other,

When there is a plurality of R ₉₃₆ , the plurality of R ₉₃₆ are the same or different from each other,

When there is a plurality of R ₉₃₇ , the plurality of R ₉₃₇ are the same or different from each other.)

In this embodiment, the delayed fluorescent compound is preferably a compound represented by the following general formula (H10).

(In the above general formula (H10),

CN is a cyano group,

L _H is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms,

D ₁₁ and D ₁₂ are each independently a group represented by the general formula (221), (222) or (223),

m is 1, 2, 3, 4 or 5,

nx is 0, 1, 2, 3, 4 or 5,

ny is 0, 1, 2, 3, 4, or 5,

nx+ny is 1, 2, 3, 4 or 5,

D ₁₁ and D ₁₂ are the same or different from each other,

A plurality of D ₁₁ are the same or different from each other,

A plurality of D ₁₂ are the same or different from each other.)

In this embodiment, the delayed fluorescent compound is preferably a compound represented by the following general formula (H100).

(In the general formula (H100), L _H , D ₁₁ , D ₁₂ , m, nx and ny are respectively L _H , D ₁₁ , D ₁₂ , m, nx and ny in the general formula (H10) I agree,

R, each independently

hydrogen atom,

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

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

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

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

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

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

A group represented by -O-(R ₉₀₄ ),

A group represented by -S-(R ₉₀₅ ),

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

Substituted or unsubstituted aralkyl group with 7 to 50 carbon atoms,

A group represented by -C(=O)R ₉₀₈ ,

-The group represented by COOR ₉₀₉ ,

Cyanogi,

nitro group,

A group represented by -P(=O)(R ₉₃₁ )(R ₉₃₂ ),

A group represented by -Ge(R ₉₃₃ )(R ₉₃₄ )(R ₉₃₅ ),

-A group represented by B(R ₉₃₆ )(R ₉₃₇ ),

A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or

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

However, at least one R is a substituent, and R as at least one substituent is bonded to L _H of the compound represented by the general formula (H100) by a carbon-carbon bond,

k is an integer greater than or equal to 1,

A plurality of R's are the same or different from each other.)

In this embodiment, the delayed fluorescent compound is preferably a compound represented by the following general formula (H101).

(In the above general formula (H101),

D ₁₁ and D ₁₂ are the same as D ₁₁ and D ₁₂ in the above general formula (H10), respectively,

R is each independently the same as R in the above general formula (H100),

m is 1, 2, 3 or 4,

nx is 0, 1, 2, 3 or 4,

ny is 0, 1, 2, 3 or 4,

k is 1, 2, 3 or 4,

nx+ny is 1, 2, 3 or 4,

m+nx+ny+k=6.)

In this embodiment, the delayed fluorescent compound is preferably a compound represented by the following general formula (H110), (H120), or (H130).

(In the general formulas (H110), (H120) and (H130),

D ₁₁ and D ₁₂ are the same as D ₁₁ and D ₁₂ in the above general formula (H10), respectively,

R is each independently the same as R in the above general formula (H100),

nx is 0, 1, 2 or 3,

ny is 0, 1, 2 or 3,

k is 1, 2 or 3,

nx+ny is 1, 2 or 3,

nx+ny+k=4.)

In the present embodiment, the group represented by the general formula (222) in the delayed fluorescent compound is represented by the following general formulas (22A), (22B), (22C), (22D), (22E), and (22F) It is preferable that it is any one group selected from the group consisting of:

(In the general formulas (22A), (22B), (22C), (22D), (22E) and (22F),

R ₂₂₁ to _{R 228} are each the same as R ₂₂₁ to _{R 228} in the general formula (222) above,

R ₂₂₉ and R ₂₃₀ are each independently the same as R ₂₉ in the general formula (224),

X _A is the same as X _A in the above general formula (225),

* in the general formulas (22A), (22B), (22C), (22D), (22E) and (22F) indicates the binding position.)

In the organic EL device according to the present embodiment, when the delayed fluorescent compound is a compound represented by general formula (H101), general formulas (22A), (22B), (22C), (22D), (22E) and ( * in 22F) is bonded to the benzene ring itself, which is explicitly shown in general formula (H101).

In the delayed fluorescent compound of the present embodiment, X _A is also preferably a sulfur atom or an oxygen atom.

In the _delayed fluorescent compound _of the _{present embodiment ,} when Alternatively, it is preferably an unsubstituted cycloalkyl group with 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group with 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 ring carbon atoms, More preferably, it is a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 50 ring carbon atoms.

In the delayed fluorescent compound of the present embodiment, it is also preferable that none of the groups consisting of two or more adjacent R ₂₁ to _{R 28} are bonded to each other.

In the delayed fluorescent compound of the present embodiment, it is also preferable that none of the adjacent two or more groups of R ₂₂₁ to _{R 228} are bonded to each other.

In the delayed fluorescent compound of the present embodiment, it is also preferable that none of the adjacent two or more groups of R ₂₃₁ to _{R 238} are bonded to each other.

R in the delayed fluorescent compound of the present embodiment is each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryl group. It is preferable that it is a heterocyclic group having 5 to 30 substituted ring atoms.

R in the delayed fluorescent compound of the present embodiment is each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted aryl group. It is preferable that it is a heterocyclic group having 5 to 18 substituted ring atoms.

R ₂₁ to _{R 28} , R ₂₂₁ to R ₂₂₈ , R ₂₃₁ to R ₂₃₈ and R ₂₉ in the delayed fluorescent compound of the present embodiment are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, It is preferable that it is a substituted or unsubstituted aryl group with 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 30 ring carbon atoms.

R ₂₁ to _{R 28} , R ₂₂₁ to R ₂₂₈ , R ₂₃₁ to R ₂₃₈ and R ₂₉ in the delayed fluorescent compound of the present embodiment are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, It is preferable that it is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring carbon atoms.

R in the delayed fluorescent compound of the present embodiment is each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryl group. It is a heterocyclic group having 5 to 30 substituted ring atoms,

R ₂₁ to _{R 28} , R ₂₂₁ to R ₂₂₈ , R ₂₃₁ to R ₂₃₈ and R ₂₉ in the delayed fluorescent compound of the present embodiment are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, It is preferable that it is a substituted or unsubstituted aryl group with 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 30 ring carbon atoms.

R in the delayed fluorescent compound of the present embodiment is each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted aryl group. It is a heterocyclic group with 5 to 18 substituted ring atoms,

R ₂₁ to _{R 28} , R ₂₂₁ to R ₂₂₈ , R ₂₃₁ to R ₂₃₈ and R ₂₉ in the delayed fluorescent compound of the present embodiment are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, It is preferable that it is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring carbon atoms.

In the compound according to the present embodiment, the substituent in the case of “substituted or unsubstituted” is,

Unsubstituted alkyl group having 1 to 25 carbon atoms,

An unsubstituted alkenyl group having 2 to 25 carbon atoms,

Unsubstituted alkynyl group having 2 to 25 carbon atoms,

An unsubstituted ring-forming cycloalkyl group having 3 to 25 carbon atoms,

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

A group represented by -O-(R ₉₀₄ ),

A group represented by -S-(R ₉₀₅ ),

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

Unsubstituted aralkyl group with 7 to 50 carbon atoms,

A group represented by -C(=O)R ₉₀₈ ,

-The group represented by COOR ₉₀₉ ,

A group represented by -P(=O)(R ₉₃₁ )(R ₉₃₂ ),

A group represented by -Ge(R ₉₃₃ )(R ₉₃₄ )(R ₉₃₅ ),

-A group represented by B(R ₉₃₆ )(R ₉₃₇ ),

-S(=O) ₂ A group represented by R ₉₃₈ ,

halogen Atom,

Cyanogi,

nitro group,

An unsubstituted aryl group with 6 to 25 ring carbon atoms, or

It is an unsubstituted heterocyclic group with 5 to 25 ring atoms,

R ₉₀₁ to _{R 909} and R ₉₃₁ to _{R 938} are each independently

hydrogen atom,

Unsubstituted alkyl group having 1 to 25 carbon atoms,

An unsubstituted aryl group having 6 to 25 ring carbon atoms, or

It is preferable that it is an unsubstituted heterocyclic group with 5 to 25 ring atoms.

In the compound according to the present embodiment, when “substituted or unsubstituted,” the substituent is a halogen atom, an unsubstituted alkyl group with 1 to 25 carbon atoms, an unsubstituted aryl group with 6 to 25 ring carbon atoms, or unsubstituted. It is preferable that it is a heterocyclic group having 5 to 25 substituted ring atoms.

In the compound according to the present embodiment, the substituent when said to be “substituted or unsubstituted” is an unsubstituted alkyl group with 1 to 10 carbon atoms, an unsubstituted aryl group with 6 to 12 ring carbon atoms, or an unsubstituted ring. It is preferable that it is a heterocyclic group having 5 to 12 atoms.

In the compound according to the present embodiment, it is also preferable that all groups described as “substituted or unsubstituted” are “unsubstituted” groups.

In this specification, the group represented by -O-(R ₉₀₄ ) is a hydroxy group when R ₉₀₄ is a hydrogen atom.

In this specification, the group represented by -S-(R ₉₀₅ ) is a thiol group when R ₉₀₅ is a hydrogen atom.

In this specification, the group represented by -P(=O)(R ₉₃₁ )(R ₉₃₂ ) is a substituted phosphine oxide group when R ₉₃₁ and R ₉₃₂ are substituents.

In this specification, the group represented by -Ge(R ₉₃₃ )(R ₉₃₄ )(R ₉₃₅ ) is a substituted germanium group when R ₉₃₃ , R ₉₃₄ and R ₉₃₅ are substituents.

In this specification, the group represented by -B(R ₉₃₆ )(R ₉₃₇ ) is a substituted boryl group when R ₉₃₆ and R ₉₃₇ are substituents.

(thermal activation delayed fluorescence)

In this specification, thermally activated delayed fluorescence is sometimes referred to as delayed fluorescence.

Delayed fluorescence is explained on pages 261 to 268 of “Device Properties of Organic Semiconductors” (edited by Chihaya Adachi, published by Kodansha). According to that document, if the energy difference ΔE ₁₃ between the singlet excited state and the triplet excited state of a fluorescent material can be reduced, the reverse energy transfer from the triplet excited state, which usually has a low transition probability, to the singlet excited state can be done with high efficiency. It is explained that thermally activated delayed fluorescence (TADF) is generated. Moreover, the generation mechanism of delayed fluorescence is explained in Figure 10.38 of the above document. The TADF mechanism is a mechanism that utilizes the phenomenon that reverse intersystem crossing from a triplet exciton to a singlet exciton occurs thermally when a material with a small energy difference (ΔST) between the singlet level and the triplet level is used. As a compound showing thermally activated delayed fluorescence (TADF property) (hereinafter also referred to as a TADF property compound), for example, a compound in which a donor site and an acceptor site are bonded within the molecule are known.

In general, delayed fluorescence emission can be confirmed by transient PL (Photoluminescence) measurement.

The behavior of delayed fluorescence can also be interpreted based on the decay curve obtained from transient PL measurements. Transient PL measurement is a method of irradiating a pulse laser to a sample to excite it and measuring the attenuation behavior (transient characteristics) of PL emission after irradiation is stopped. PL light emission in a TADF compound is classified into a light emission component from a singlet exciton generated from the first PL excitation and a light emission component from a singlet exciton generated via a triplet exciton. The lifetime of the singlet exciton generated from the first PL excitation is very short, on the order of nanoseconds. Therefore, the light emission from the singlet exciton attenuates quickly after irradiation with a pulse laser.

On the other hand, delayed fluorescence is attenuated gently because it is emitted from a singlet exciton generated via a long-lived triplet exciton. In this way, there is a large temporal difference between the light emission from the singlet exciton generated in the first PL excitation and the light emission from the singlet exciton generated via the triplet exciton. Therefore, the emission intensity derived from delayed fluorescence can be determined.

2, a schematic diagram of an example device for measuring transient PL is shown. An example of a transient PL measurement method and delayed fluorescence behavior analysis using Figure 2 will be explained.

The transient PL measurement device 100 in FIG. 2 includes a pulse laser unit 101 that can irradiate light of a predetermined wavelength, a sample chamber 102 that accommodates a measurement sample, and a device that specifies the light emitted from the measurement sample. It is provided with a spectroscope 103, a streak camera 104 for forming a two-dimensional image, and a personal computer 105 for receiving and analyzing the two-dimensional image. Additionally, measurement of transient PL is not limited to the device shown in Figure 2.

The sample accommodated in the sample chamber 102 is obtained by forming a thin film doped with a doping material at a concentration of 12% by mass relative to the matrix material on a quartz substrate.

A pulse laser is irradiated from the pulse laser unit 101 to the thin film sample stored in the sample chamber 102 to excite the doping material. Light emission is extracted in a direction of 90 degrees with respect to the direction of irradiation of the excitation light, the extracted light is split into a spectroscope 103, and a two-dimensional image is formed within the streak camera 104. As a result, a two-dimensional image can be obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and the bright spot corresponds to light emission intensity. By cutting this two-dimensional image along a predetermined time axis, an emission spectrum can be obtained where the vertical axis is the emission intensity and the horizontal axis is the wavelength. Additionally, by cutting the two-dimensional image along the wavelength axis, an attenuation curve (transient PL) can be obtained where the vertical axis is the logarithm of the emission intensity and the horizontal axis is time.

For example, using the following compound HX1 as a matrix material and the following compound DX1 as a doping material, thin film sample A was produced as described above, and transient PL measurement was performed.

Here, the attenuation curve was analyzed using the thin film sample A and thin film sample B described above. Thin film sample B was produced as described above using the following compound HX2 as a matrix material and the above compound DX1 as a doping material.

In Figure 3, attenuation curves obtained from transient PL measured for thin film sample A and thin film sample B are shown.

As described above, by measuring transient PL, it is possible to obtain a light emission attenuation curve with the vertical axis being the light emission intensity and the horizontal axis being time. Based on these emission decay curves, fluorescence emitting from a singlet excited state generated by photoexcitation and delayed fluorescence emitting from a singlet excited state generated by reverse energy transfer via the triplet excited state. The intensity ratio can be estimated. In delayed fluorescent materials, the ratio of the intensity of slowly decaying delayed fluorescence to the intensity of rapidly decaying fluorescence is somewhat large.

Specifically, light emission from delayed fluorescent materials includes prompt light emission (immediate light emission) and delay light emission (delayed light emission). Prompt light emission (immediate light emission) is light emission that is observed immediately from the excited state after being excited with pulsed light (light irradiated from a pulse laser) of a wavelength absorbed by the delayed fluorescent material. Delay light emission (delayed light emission) is light emission that is not observed immediately after excitation by the pulse light, but is observed thereafter.

The amount and ratio of prompt emission and delay emission can be obtained by the same method as described in “Nature 492, 234-238, 2012” (Reference 1). Additionally, the device used to calculate the amount of prompt light emission and delay light emission is not limited to the device described in Reference 1 or the device described in FIG. 2.

In addition, to measure the delayed fluorescence of the delayed fluorescent compound according to the present embodiment, a sample prepared by the method shown below is used. For example, the delayed fluorescent compound according to the present embodiment is dissolved in toluene to prepare a diluted solution having an absorbance of 0.05 or less at the excitation wavelength to eliminate the contribution of self-absorption. Additionally, in order to prevent quenching by oxygen, the sample solution is frozen and degassed and then enclosed in a cell with a cover under an argon atmosphere, thereby creating an oxygen-free sample solution saturated with argon.

The fluorescence spectrum of the sample solution was measured using a spectrofluorescence photometer FP-8600 (manufactured by Nippon Bunko Co., Ltd.), and the fluorescence spectrum of the ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. Using the fluorescence area intensity of both spectra, Morris et al. J. Phys. Chem. The total fluorescence quantum yield is calculated by equation (1) in 80 (1976) 969.

In this embodiment _, when the amount of prompt emission ₍ immediate emission) of the compound to be measured is X _P and the amount of delay emission (delayed emission) is X _D , it is preferable that the value of do.

Measurement of the amount and ratio of prompt light emission and delay light emission from compounds other than the delayed fluorescent compound in the present specification is the same as the measurement of the amount and ratio of prompt light emission and delay light emission of the delayed fluorescent compound according to the present embodiment.

(ΔST)

In this embodiment, the difference (S ₁ -T _77K ) between the lowest singlet excitation energy S ₁ and the energy gap T _77K at 77[K] is defined as ΔST.

In this embodiment, the difference ΔST(GT2) between the lowest singlet excitation energy S ₁ (GT2) of the delayed fluorescent compound and the energy gap T _77K (GT2) at 77 [K] of the delayed fluorescent compound is preferably It is less than 0.5 eV, more preferably less than 0.3 eV, even more preferably less than 0.2 eV, even more preferably less than 0.1 eV, and even more preferably less than 0.01 eV. That is, ΔST(GT2) preferably satisfies the following equation (Equation 2), (Equation 2A), (Equation 2B), (Equation 2C), or (Equation 2D).

ΔST(GT2)=S ₁ (GT2)-T _77K (GT2)<0.5 eV... (Number 2)

ΔST(GT2)=S ₁ (GT2)-T _77K (GT2)<0.3 eV... (number 2A)

ΔST(GT2)=S ₁ (GT2)-T _77K (GT2)<0.2 eV... (Number 2B)

ΔST(GT2)=S ₁ (GT2)-T _77K (GT2)<0.1 eV... (number 2C)

ΔST(GT2)=S ₁ (GT2)-T _77K (GT2)<0.01 eV... (can be 2D)

(Relationship between triplet energy and energy gap at 77[K])

Here, the relationship between triplet energy and the energy gap at 77[K] will be explained. In this embodiment, the energy gap at 77[K] is different from the triplet energy normally defined.

Triplet energy is measured as follows. First, a sample is prepared in which a solution of the compound to be measured is dissolved in an appropriate solvent and sealed in a quartz glass tube. For this sample, measure the phosphorescence spectrum (ordinate: phosphorescence emission intensity, abscissa: wavelength) at a low temperature (77 [K]), draw a tangent line for the rise on the short wavelength side of this phosphorescence spectrum, and draw a tangent line and the abscissa axis. Based on the wave device of the intersection point, the triplet energy is calculated from a predetermined conversion equation.

Here, among the compounds according to the present embodiment, it is preferable that the thermally activated delayed fluorescent compound is a compound with a small ΔST. When ΔST is small, intersystem crossing and anti-intersystem crossing are likely to occur even at low temperature (77 [K]), and singlet excitation and triplet excitation states coexist. As a result, the spectrum measured in the above manner includes light emission from both the singlet excited state and the triplet excited state, and although it is difficult to distinguish from which state the light is emitted, it is basically triplet energy. The value of is thought to be dominant.

Therefore, in this embodiment, the measurement method is the same as the normal triplet energy T, but in order to distinguish the difference in the strict sense, the value measured as follows is called energy gap T _77K . Dissolve the compound to be measured in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) to a concentration of 10 μmol/L to obtain a solution, and place this solution in a quartz cell as a measurement sample. Do this. For this measurement sample, measure the phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) at a low temperature (77 [K]), draw a tangent line for the rise on the short wavelength side of this phosphorescence spectrum, and draw a tangent line and Based on the wave length λ _edge [nm] of the intersection of the horizontal axes, the amount of energy calculated from the following conversion equation (F1) is set to the energy gap T _77K at 77 [K].

Conversion formula (F1): T _77K [eV]=1239.85/λ _edge

The tangent line for the rise of the short wavelength side of the phosphorescence spectrum is drawn as follows. When moving the spectrum curve from the short wavelength side of the phosphorescence spectrum to the maximum value on the shortest wavelength side among the maximum values of the spectrum, consider the tangent line at each point on the curve toward the long wavelength side. This tangent line increases in slope as the curve rises (i.e., as the longitudinal axis increases). The tangent line drawn at the point where the value of this slope takes the maximum value (that is, the tangent line at the inflection point) is taken as the tangent line to the rise of the short wavelength side of the phosphorescence spectrum.

In addition, the local maximum point with a peak intensity of 15% or less of the maximum peak intensity of the spectrum is not included in the local maximum on the shortest wavelength side described above, and the slope value closest to the local maximum on the shortest wavelength side takes the local maximum. The tangent line drawn is taken as the tangent line to the rise of the short wavelength side of the phosphorescence spectrum.

To measure phosphorescence, the F-4500 type spectrofluorescence meter manufactured by Hitachi High-Technology Co., Ltd. can be used. In addition, the measuring device is not limited to this, and measurement may be performed by combining a cooling device, a low-temperature container, an excitation light source, and a light receiving device.

(lowest excitation singlet energy S ₁ )

A method for measuring the lowest singlet excitation energy S ₁ using a solution (sometimes called a solution method) includes the following method.

Prepare a 10 μmol/L toluene solution of the compound to be measured, place it in a quartz cell, and measure the absorption spectrum of this sample (vertical axis: absorption intensity, abscissa: wavelength) at room temperature (300 K). A tangent line is drawn on the long wavelength side of the absorption spectrum, and the wavelength λedge [nm] at the intersection of the tangent line and the horizontal axis is substituted into the conversion equation (F2) shown below to calculate the lowest singlet excitation energy.

Conversion formula (F2): S ₁ [eV]=1239.85/λedge

Examples of the absorption spectrum measuring device include, but are not limited to, a spectrophotometer (device name: U3310) manufactured by Hitachi Corporation.

The tangent line to the fall on the long wavelength side of the absorption spectrum is drawn as follows. When moving over the spectrum curve in the long-wavelength direction from the maximum value on the longest wavelength side among the maximum values of the absorption spectrum, consider the tangent line at each point on the curve. The slope of this tangent line decreases as the curve descends (i.e., as the value of the vertical axis decreases), and then increases repeatedly. At the point where the slope value takes the minimum value on the longest wavelength side (excluding the case where the absorbance is 0.1 or less), the tangent line drawn is taken as the tangent line to the descent of the long wavelength side of the absorption spectrum.

In addition, the maximum point with an absorbance value of 0.2 or less is not included in the maximum value on the longest wavelength side.

(Method for producing delayed fluorescent compounds)

Delayed fluorescent compounds can be prepared by known methods. Additionally, delayed fluorescent compounds can also be produced by using known substitution reactions and raw materials tailored to the target according to known methods.

(Specific examples of delayed fluorescent compounds)

Specific examples of delayed fluorescent compounds include the following compounds. However, the present invention is not limited to these specific examples.

[Fluorescent material]

In this embodiment, the fluorescent material is preferably a compound that does not exhibit thermally activated delayed fluorescence. In this embodiment, the fluorescent material is not a phosphorescent metal complex. In this embodiment, it is preferable that the fluorescent material is not a metal complex.

In this embodiment, the fluorescent material is one or more compounds selected from the group consisting of third compounds represented by the following general formula (31) or (32). The third compound as the fluorescent material may be a compound represented by the following general formula (31) or may be a compound represented by the following general formula (32).

[(In the general formula (31) above,

C ₁ ring and D ₁ ring are,

are joined to each other by a single bond, or

bonded to each other through O, S, NR ₃₃ , Si(R ₃₄ )(R ₃₅ ) or C(R ₃₇ )(R ₃₈ ) or without bonding to each other,

The C 1 ring and the D 1 ring which are not bonded to each other by a single bond and are not bonded to each other through O, S _, NR ₃₃ , Si(R ₃₄ )(R ₃₅ ) or C ₍ R ₃₇ )(R ₃₈ ), And A ₁ ring and B ₁ ring are each independently

A substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 60 carbon atoms, or

It is a substituted or unsubstituted heterocycle with 5 to 60 ring atoms,

The substituent of R _E or R _E is,

It combines with at least one of the A ₁ ring, the substituent of the A ₁ ring, the B ₁ ring, and the substituent of the B ₁ ring to form a substituted or unsubstituted monocycle, or

Combined with at least one of the A ₁ ring, the substituent of the A ₁ ring, the B ₁ ring, and the substituent of the B ₁ ring to form a substituted or unsubstituted condensed ring, or

It does not combine with the A ₁ ring, the substituent of the A ₁ ring, the B ₁ ring, and the substituent of the B ₁ ring.)

(In the above general formula (32),

A ₂ ring, B ₂ ring and C ₂ ring are each independently

A substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 60 carbon atoms, or

It is a substituted or unsubstituted heterocycle with 5 to 60 ring atoms,

The D ₂ ring is a substituted or unsubstituted monocyclic ring having 5 to 7 ring atoms that may be condensed with at least one substituted or unsubstituted non-aromatic ring having 5 to 60 ring atoms,

The C ₂ ring and the D ₂ ring are condensed by sharing a single bond or double bond with each other,

A ₂ ring and D ₂ ring are,

are joined to each other by a single bond, or

bonded to each other through O, S, NR ₃₃ , Si(R ₃₄ )(R ₃₅ ) or C(R ₃₇ )(R ₃₈ ) or without bonding to each other,

The substituent of R _F or R _F is,

It combines with at least one of the A ₂ ring, the substituent of the A ₂ ring, the B ₂ ring, and the substituent of the B ₂ ring to form a substituted or unsubstituted monocycle, or

Combined with at least one of the A ₂ ring, the substituent of the A ₂ ring, the B ₂ ring, and the substituent of the B ₂ ring to form a substituted or unsubstituted condensed ring, or

It does not combine with the A ₂ ring, the substituent of the A ₂ ring, the B ₂ ring, and the substituent of the B ₂ ring.)

(In the above general formula (31) or (32),

R _E which does not combine with the A ₁ ring, the substituents of the A ₁ ring, the B ₁ ring, and the substituents of the B ₁ ring, and the A ₂ ring, the substituents of the A ₂ ring, the B ₂ ring, and the B R _F that is not bonded to the substituent of _{the 2} ring is each independently

hydrogen atom,

A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,

A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,

Substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,

A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 20 carbon atoms,

A substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms,

-CR ₃₉ =Iminyl group represented by N, or

It is a substituted or unsubstituted alkynyl group with 2 to 20 carbon atoms,

Y _E and Y _F are each independently a single bond, O, S, NR ₃₃ , Si(R ₃₄ )(R ₃₅ ) or C(R ₃₇ )(R ₃₈ ),

When Y _E is a single bond, the B ₁ ring and the C ₁ ring are bonded or bonded through O, S, NR ₃₃ , Si(R ₃₄ )(R ₃₅ ) or C(R ₃₇ )(R ₃₈ ) without doing,

When Y _F is a single bond, the B ₂ ring and the C ₂ ring are bonded or bonded through O, S, NR ₃₃ , Si (R ₃₄ ) (R ₃₅ ) or C (R ₃₇ ) (R ₃₈ ) without doing,

R ₃₄ and R ₃₅ are,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

R ₃₇ and R ₃₈ are,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

In the general formula (31), R ₃₃ , R ₃₄ , R ₃₅ , R ₃₇ and R ₃₈ are each independently

Combined with at least one of the A ₁ ring, the B ₁ ring, and the C ₁ ring to form a substituted or unsubstituted monocycle, or

Combined with at least one of the A ₁ ring, the B ₁ ring, and the C ₁ ring to form a substituted or unsubstituted condensed ring, or

Not bonded to the A ₁ ring, the B ₁ ring, and the C ₁ ring,

In the general formula (32), R ₃₃ , R ₃₄ , R ₃₅ , R ₃₇ and R ₃₈ are each independently

Combined with at least one of the A ₂ ring, the B ₂ ring, and the C ₂ ring to form a substituted or unsubstituted monocycle, or

Combined with at least one of the A ₂ ring, the B ₂ ring, and the C ₂ ring to form a substituted or unsubstituted condensed ring, or

Not bonded to the A ₂ ring, the B ₂ ring and the C ₂ ring,

R ₃₉ , and R ₃₃ , R ₃₄ , R ₃₅ , R ₃₇ and R ₃₈ which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently

A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,

A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,

A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or

It is a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,

When there is a plurality of R ₃₃ , the plurality of R ₃₃ are the same or different from each other,

When there is a plurality of R ₃₄ , the plurality of R ₃₄ are the same or different from each other,

When there is a plurality of R ₃₅ , the plurality of R ₃₅ are the same or different from each other,

When there is a plurality of R ₃₇ , the plurality of R ₃₇ are the same or different from each other,

When there is a plurality of R ₃₈ , the plurality of R ₃₈ are the same or different from each other.)]

In this embodiment, the compound represented by the general formula (31) is also preferably a compound represented by the following general formula (35).

(In the above general formula (35),

A group consisting of two or more adjacent elements from R ¹ to ^{R 3} , a group consisting of two or more adjacent elements from R ⁴ to ^{R 6} , a group consisting of two or more adjacent elements from R ¹² to ^{R 15} , and a group consisting of two or more adjacent elements from R 4 to R ⁶ . Among ¹⁹ , at least 1 set of groups consisting of 2 or more adjacent items,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

One or more sets of groups consisting of two or more adjacent R ⁷ to R ¹¹ ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

The joint price of R ⁷ and R ⁶ ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

The joint price of R ¹¹ and R ¹² ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

R ¹ to ^{R 19} that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently

hydrogen atom,

A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,

A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,

Substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,

A substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms,

A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 20 carbon atoms,

Cyanogi,

N(R ²² ) ₂ ;

OR ²⁰ ,

SR ²⁰ ,

B(R ²¹ ) ₂ ;

SiR ²⁴ R ²⁵ R ²⁶ or

It is a halogen atom,

At least one set of groups consisting of two R ^22s and two sets of R ^21s ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

R ²⁰ combines with at least one of adjacent R ¹ to ^{R 19} to form a substituted or unsubstituted monocycle, or combines with each other to form a substituted or unsubstituted condensed ring, or does not combine with each other,

R ²¹ each independently combines with at least one of adjacent R ¹ to ^{R 19} to form a substituted or unsubstituted monocycle, or combines with each other to form a substituted or unsubstituted condensed ring, or does not combine with each other. ,

R ²² each independently combines with at least one of adjacent R ¹ to ^{R 19} to form a substituted or unsubstituted monocycle, or combines with each other to form a substituted or unsubstituted condensed ring, or does not combine with each other. ,

R ²⁰ to ^{R 22} that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently

A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,

A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,

A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or

It is a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,

The combination of two adjacent R ²⁴ and R ²⁵ ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

R ²⁶ , and R ²⁴ and R ²⁵ , which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring, are each independently

A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,

A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,

A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or

It is a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms.)

In this embodiment, the compound represented by the general formula (31) is preferably any one compound selected from the group consisting of compounds represented by the following general formulas (351), (352), and (353).

(In the general formulas (351) and (352),

A group consisting of two or more adjacent elements from R ¹ to ^{R 3} , a group consisting of R ⁴ and R ⁵ , a group consisting of two or more adjacent elements from R ⁸ to ^{R 11} , and a group consisting of two or more adjacent elements from R ¹² to R ¹⁵ . A group consisting of two or more adjacent R ¹⁶ to R ¹⁹ , at least one set of groups consisting of

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

R ¹ to R ⁵ and R ⁸ to ^{R 19} that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently R ¹ in the general formula (35) Same as ~R ⁵ and R ⁸ ~R ^19. )

(In the above general formula (353),

A group consisting of two or more adjacent elements from R ¹ to ^{R 3} , a group consisting of two or more adjacent elements from R ⁴ to R ⁶ , a group consisting of two or more adjacent elements from R ⁷ to ^{R 10} , R ¹³ to R ¹⁵ A group consisting of two or more adjacent elements among R ^{16 to R 19, and one or more sets consisting of two or more adjacent elements R 16} to ^{R 19} ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

R ¹ to R ¹⁰ and R ¹³ to ^{R 19} that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently R ¹ in the general formula (35) Same as ~R ¹⁰ and R ¹³ ~ ^{R 19.} )

(Method for producing a compound represented by General Formula (31))

The compound represented by the general formula (31) can be prepared by known methods. In addition, the compound represented by the general formula (31) can also be produced by using known substitution reactions and raw materials tailored to the target according to known methods.

(Specific examples of compounds represented by general formula (31))

Specific examples of the compound represented by the general formula (31) include the compounds shown below.

In this embodiment, the compound represented by the general formula (32) is also preferably a compound represented by the following general formula (322).

[(In the general formula (322) above,

A ₂ ring, B ₂ ring, C ₂ ring, R _F and Y _F are each the same as A ₂ ring, B ₂ ring, C ₂ ring, R _F and Y _F in the general formula (32),

X _F is CR ₃₂₁ or a nitrogen atom,

Z _F is CR ₃₂₂ or a nitrogen atom,

R ₃₂₁ and R ₃₂₂ are the same or different from each other,

The group consisting of R ₃₂₁ and R ₃₂₂ combine with each other to form a substituted or unsubstituted non-aromatic ring having 5 to 60 ring atoms, or do not combine with each other,

A ₂ ring and R ₃₂₁ are bonded to each other by a single bond, bonded to each other through O, S, NR ₃₃ , Si(R ₃₄ )(R ₃₅ ) or C(R ₃₇ )(R ₃₈ ) or not bonded to each other. ,

R ₃₂₂ combines with the C ₂ ring to form a substituted or unsubstituted monocyclic ring, forms a substituted or unsubstituted condensed ring, or does not combine with each other,

R ₃₂₁ and R ₃₂₂ , which do not form the substituted or unsubstituted non-aromatic group having 5 to 60 ring atoms and do not bind to the A ₂ ring and the C ₂ ring, are each independently

hydrogen atom,

A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,

A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,

Substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,

A substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms,

A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 20 carbon atoms,

-A group represented by Si(R ₃₈₁ )(R ₃₈₂ )(R ₃₈₃ ),

A group represented by -O-(R ₃₈₄ ),

A group represented by -S-(R ₃₈₅ ),

A group represented by -N(R ₃₈₆ )(R ₃₈₇ ),

-A group represented by B(R ₃₈₈ )(R ₃₈₉ ),

halogen atom, or

It is cyano group.)

(Among the third compounds,

A composition consisting of R ₃₈₁ and R ₃₈₂ ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

A composition consisting of R ₃₈₆ and R ₃₈₇ ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

A composition consisting of R ₃₈₈ and R ₃₈₉ ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

At least one selected from the group consisting of R ₃₈₄ to _{R 389} combines with an adjacent substituent to form a substituted or unsubstituted monocycle, or combines with each other to form a substituted or unsubstituted condensed ring, or combines with each other. without doing,

R ₃₈₃ , and R 381 , R ₃₈₂ , R ₃₈₄ , R ₃₈₅ , R ₃₈₆ and _{R 387 which} do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently

A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,

A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,

A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or

It is a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,

R ₃₈₈ and R ₃₈₉ , which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring, are each independently

A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,

A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,

Substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,

A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 20 carbon atoms,

A group represented by -O-(R ₃₈₄ ), or

It is a group represented by -N(R ₃₈₆ )(R ₃₈₇ ),

When there is a plurality of R ₃₈₁ , the plurality of R ₃₈₁ are the same or different from each other,

When there is a plurality of R ₃₈₂ , the plurality of R ₃₈₂ are the same or different from each other,

When there is a plurality of R ₃₈₃ , the plurality of R ₃₈₃ are the same or different from each other,

When there is a plurality of R ₃₈₄ , the plurality of R ₃₈₄ are the same or different from each other,

When a plurality of R ₃₈₅ is present, the plurality of R ₃₈₅ is the same as or different from each other,

When there is a plurality of R ₃₈₆ , the plurality of R ₃₈₆ is the same or different from each other,

When there is a plurality of R ₃₈₇ , the plurality of R ₃₈₇ are the same or different from each other,

When there is a plurality of R ₃₈₈ , the plurality of R ₃₈₈ are the same or different from each other,

When there is a plurality of R ₃₈₉ , the plurality of R ₃₈₉ are the same or different from each other.)]

In this embodiment, the compound represented by the general formula (32) is also preferably a compound represented by the following general formula (323).

(In the above general formula (323),

A ₂ ring and R _F are each the same as A ₂ ring and R _F in the general formula (32),

X _F and Z _F are each the same as X _F and Z _F in the above general formula (322),

A group consisting of R ₃₃₁ and R ₃₂₁ in Z _F , a group consisting of R ₃₃₆ and R _F , a group consisting of R ₃₃₆ and a substituent of R _F , a group consisting of two or more adjacent ones of R ₃₃₁ to _{R 333} , and Among R ₃₃₄ to R ₃₃₆ , at least one set of two or more adjacent pairs,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

R ₃₃₁ to _{R 336} that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently

hydrogen atom,

A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,

A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,

Substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,

A substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms,

A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 20 carbon atoms,

-A group represented by Si(R ₃₈₁ )(R ₃₈₂ )(R ₃₈₃ ),

A group represented by -O-(R ₃₈₄ ),

A group represented by -S-(R ₃₈₅ ),

A group represented by -N(R ₃₈₆ )(R ₃₈₇ ),

-A group represented by B(R ₃₈₈ )(R ₃₈₉ ),

halogen atom, or

It is cyano group,

At least one selected from R ₃₈₄ to _{R 389} combines with at least one selected from adjacent R ₃₃₁ to _{R 336} to form a substituted or unsubstituted monocycle, or combines with each other to form a substituted or unsubstituted condensed ring do not form or combine with each other.)

In this embodiment, the compound represented by the general formula (32) is also preferably a compound represented by the following general formula (324).

(In the above general formula (324),

R _F is the same as R _F in the above general formula (32),

R ₃₃₁ to _{R 336} are each the same as R ₃₃₁ to _{R 336} in the general formula (323) above,

X _F and Z _F are each the same as X _F and Z _F in the above general formula (322),

_{When ​ ​ ​ ​ ​ ​ ​ ​} combined or not combined with each other,

One or more groups consisting of a group consisting of R ₃₄₂ and R _F , a group consisting of R ₃₄₂ and a substituent of R _F , and a group consisting of two or more adjacent ones of R ₃₄₂ to _{R 345} ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

R ₃₄₂ to _{R 345} that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently

hydrogen atom,

A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,

A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,

Substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,

A substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms,

A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 20 carbon atoms,

-A group represented by Si(R ₃₈₁ )(R ₃₈₂ )(R ₃₈₃ ),

A group represented by -O-(R ₃₈₄ ),

A group represented by -S-(R ₃₈₅ ),

A group represented by -N(R ₃₈₆ )(R ₃₈₇ ),

-A group represented by B(R ₃₈₈ )(R ₃₈₉ ),

halogen atom, or

It is cyano group.)

In this embodiment, one or more groups of two or more adjacent R ₃₄₂ to _{R 345} combine with each other to form a substituted or unsubstituted monocycle, or combine with each other to form a substituted or unsubstituted condensed ring. It is also desirable to form

In the present embodiment, one or more groups of two or more adjacent R ₃₄₂ to _{R 345} are combined to form a substituted or unsubstituted condensed ring represented by the following general formula (326): desirable.

(In the above general formula (326),

W _F is O, S, NR ₃₄₆ or C(R ₃₄₇ )(R ₃₄₈ ),

R ₃₄₆ is

A substituted or unsubstituted alkyl group with 1 to 8 carbon atoms (preferably a substituted or unsubstituted alkyl group with 1 to 4 carbon atoms), or

It is a substituted or unsubstituted aryl group with 6 to 10 ring atoms (preferably a substituted or unsubstituted phenyl group),

R ₃₄₇ and R ₃₄₈ are each independently

A substituted or unsubstituted alkyl group with 1 to 8 carbon atoms (preferably a substituted or unsubstituted alkyl group with 1 to 4 carbon atoms, more preferably a methyl group), or

A substituted or unsubstituted aryl group having 6 to 18 ring atoms (preferably a substituted or unsubstituted aryl group having 6 to 10 ring atoms, more preferably a substituted or unsubstituted phenyl group),

R ₃₂₂ to R ₃₂₅ are each independently

hydrogen atom,

A substituted or unsubstituted aryl group with 6 to 60 ring carbon atoms (preferably a substituted or unsubstituted aryl group with 6 to 30 ring carbon atoms, more preferably a substituted or unsubstituted aryl group with 6 to 18 ring carbon atoms) aryl group),

A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms (preferably a substituted or unsubstituted heterocyclic group with 5 to 30 ring atoms, more preferably a substituted or unsubstituted heterocyclic group with 5 to 30 ring atoms) Complex ventilation of 18),

Substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,

A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 20 carbon atoms,

A group represented by -O-(R ₃₈₄ ),

A group represented by -S-(R ₃₈₅ ),

A group represented by -N(R ₃₈₆ )(R ₃₈₇ ),

halogen atom, or

It is cyano group,

* indicates binding position.)

In this embodiment, it is also preferable that the group consisting of R ₃₄₃ and R ₃₄₄ of the compound represented by the general formula (324) combine with each other to form a ring represented by the general formula (326), and in this case, the compound An example is represented by the general formula (327) below.

(In the above general formula (327),

R _F is the same as R _F in the above general formula (32),

R ₃₃₁ to _{R 336} are each the same as R ₃₃₁ to _{R 336} in the general formula (323) above,

X _F and Z _F are each the same as X _F and Z _F in the above general formula (322),

R ₃₄₂ and R ₃₄₅ are the same as R ₃₄₂ and R ₃₄₅ in the general formula (324), respectively,

W _F and R ₃₂₂ to R ₃₂₅ are the same as W _F and R ₃₂₂ to _{R 325} in the above general formula (326), respectively.)

In this embodiment, it is also preferable that none of the groups consisting of two or more adjacent R ₃₄₂ to R ₃₄₅ are bonded to each other.

In the present embodiment, R _F in the compound represented by the general formula (32) is also preferably a group represented by the following general formula (325).

(In the above general formula (325),

A group consisting of R ₃₃₇ and the B ₂ ring, a group consisting of R 337 and a substituent on the B ₂ ring, _a group consisting of R ₃₄₁ and A ₂ ring, a group consisting of R ₃₄₁ and a substituent on the A ₂ ring, R ₃₃₆ and R ₃₃₇ A group consisting of a group consisting of R ₃₄₁ and R ₃₄₂ , and at least one set of a group consisting of two or more adjacent ones of R ₃₃₇ to _{R 341} ,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

R ₃₃₇ to _{R 341} , which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring, are each independently

hydrogen atom,

A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,

A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,

Substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,

A substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms,

A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 20 carbon atoms,

-A group represented by Si(R ₃₈₁ )(R ₃₈₂ )(R ₃₈₃ ),

A group represented by -O-(R ₃₈₄ ),

A group represented by -S-(R ₃₈₅ ),

A group represented by -N(R ₃₈₆ )(R ₃₈₇ ),

-A group represented by B(R ₃₈₈ )(R ₃₈₉ ),

halogen atom, or

It is cyano group,

* indicates binding position.)

In this embodiment, when R _F of the compound represented by the general formula (324) is a group represented by the general formula (325), the compound represented by the general formula (32) has the following general formula (329) displayed.

(In the above general formula (329),

R ₃₃₁ to _{R 336} are each the same as R ₃₃₁ to _{R 336} in the general formula (323) above,

X _F and Z _F are each the same as X _F and Z _F in the above general formula (322),

R ₃₄₂ to _{R 345} are each the same as R ₃₄₂ to _{R 345} in the general formula (324) above,

R ₃₃₇ to _{R 341} are the same as R ₃₃₇ to _{R 341} in the general formula (325) above.)

In this embodiment, the compound represented by the general formula (32) is also preferably a compound represented by the following general formula (330) or (331).

(In the general formulas (330) and (331),

R ₃₃₁ to _{R 336} are each the same as R ₃₃₁ to _{R 336} in the general formula (323) above,

X _F and Z _F are each the same as X _F and Z _F in the above general formula (322),

R ₃₄₂ to _{R 345} are each the same as R ₃₄₂ to _{R 345} in the general formula (324) above,

R ₃₃₇ to _{R 341} are each the same as R ₃₃₇ to _{R 341} in the general formula (325) above.)

In the present embodiment, among the compounds represented _{by the} general _formula (32), it is preferable that at least one _{of R 321} in It is desirable that not all of them are hydrogen atoms.

In the present embodiment, the group consisting of R ₃₂₁ and R ₃₂₂ are bonded to each other and have 5 to 60 substituted or unsubstituted ring atoms (preferably 5 to 30 ring atoms, more preferably 5 ring atoms). A non-aromatic ring of ~18) may be formed.

In this embodiment, the group consisting of R ₃₂₁ and R ₃₂₂ does not need to be combined with each other.

In _{this embodiment , R 321 for} The group is preferably a substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms, or a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group with 6 to 60 ring carbon atoms. It is more preferable that it is a group represented by the following general formula (328).

(In the above general formula (328),

One or more sets of R ₃₅₀ to R ₃₅₄ consisting of two or more adjacent ones,

Combine with each other to form a substituted or unsubstituted monocycle,

Combine with each other to form a substituted or unsubstituted condensed ring, or

do not combine with each other,

R ₃₅₀ to _{R 354} that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently

hydrogen atom,

A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,

A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,

Substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,

A substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms,

A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 20 carbon atoms,

-A group represented by Si(R ₃₈₁ )(R ₃₈₂ )(R ₃₈₃ ),

A group represented by -O-(R ₃₈₄ ),

A group represented by -S-(R ₃₈₅ ),

A group represented by -N(R ₃₈₆ )(R ₃₈₇ ),

-A group represented by B(R ₃₈₈ )(R ₃₈₉ ),

halogen atom, or

It is cyano group,

* indicates binding position.)

(Method for producing a compound represented by General Formula (32))

The compound represented by the general formula (32) can be prepared by known methods. In addition, the compound represented by the general formula (32) can also be produced by using known substitution reactions and raw materials tailored to the target according to known methods.

(Specific examples of compounds represented by general formula (32))

Specific examples of the compound represented by the general formula (32) include the compounds shown below.

In one embodiment, the substituent in the case of “substituted or unsubstituted” in each of the above general formulas is an unsubstituted alkyl group with 1 to 50 carbon atoms, an unsubstituted alkenyl group with 2 to 50 carbon atoms, or an unsubstituted carbon number of 2. -50 alkynyl group, unsubstituted cycloalkyl group with 3 to 50 ring carbon atoms, -Si(R _901a )(R _902a )(R _903a ), -O-(R _904a ), -S-(R _905a ), -N(R _906a )(R _907a ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group with 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group with 5 to 50 ring atoms,

R _901a to R _907a are each independently a hydrogen atom, an unsubstituted alkyl group with 1 to 50 carbon atoms, an unsubstituted aryl group with 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group with 5 to 50 ring atoms. ,

When 2 or more R _901a are present, 2 or more R _901a are the same as or different from each other, when 2 or more R _902a are present, 2 or more R _902a are the same or different from each other, and when 2 or more R _903a are present, 2 When two or more R _903a are present, two or more R _903a are the same as or different from each other, and when two or more R _904a are present, two or more R 904a are the same as or different from each other, and when two or more R _905a are present, two or more R _905a are the same as or different from each other, When two or more R _906a are present, two or more R _906a are the same as or different from each other, and when two or more R _907a are present, the two or more R _907a are the same or different from each other.

In one embodiment, the substituent in the case of "substituted or unsubstituted" in each of the above general formulas is an unsubstituted alkyl group with 1 to 50 carbon atoms, an unsubstituted aryl group with 6 to 50 ring carbon atoms, or an unsubstituted alkyl group with 6 to 50 ring carbon atoms. It is a heterocyclic group having 5 to 50 ring forming atoms.

In one embodiment, the substituent in the case of “substituted or unsubstituted” in each of the above general formulas is an unsubstituted alkyl group with 1 to 18 carbon atoms, an unsubstituted aryl group with 6 to 18 ring carbon atoms, or an unsubstituted alkyl group with 6 to 18 ring carbon atoms. It is a heterocyclic group having 5 to 18 ring forming atoms.

(maximum peak wavelength)

In this embodiment, the maximum peak wavelength of the third compound as the fluorescent material is preferably 480 nm or less, and more preferably 475 nm or less.

In this embodiment, the maximum peak wavelength of the third compound as the fluorescent material is preferably 430 nm or more, and more preferably 440 nm or more.

In this specification, the maximum peak wavelength of fluorescence emission is sometimes referred to as the maximum peak wavelength of fluorescence emission.

In the organic EL device of this embodiment, the first compound preferably emits blue light. In this specification, blue light emission refers to light emission in which the maximum peak wavelength of the fluorescence spectrum is within the range of 430 nm to 480 nm.

(Emission spectrum half width)

In this embodiment, the emission spectrum full width at half maximum (FWHM) of the third compound as the fluorescent material is preferably 40 nm or less, and more preferably 30 nm or less.

In this embodiment, the emission spectrum full width at half maximum (FWHM) of the third compound as the fluorescent material is preferably 5 nm or more, and more preferably 10 nm or more.

FWHM is an abbreviation for full width at half maximum.

In this specification, the maximum peak wavelength of fluorescence emission refers to the emission in the fluorescence spectrum measured in a toluene solution in which the compound to be measured is dissolved at a concentration of 10 ^-6 mol/liter or more and 10 ^-5 mol/liter or less. It refers to the maximum peak wavelength of the fluorescence spectrum where the intensity is maximum. The emission spectrum full width at half maximum (FWHM) is the full width at half maximum at the maximum peak of the fluorescence spectrum. A fluorescence spectrum measuring device can be used as a device for measuring the fluorescence spectrum. For example, a fluorescence spectrum measuring device manufactured by Nippon Bunko Co., Ltd. (device name: FP-8300) can be used. Additionally, the fluorescence spectrum measuring device is not limited to the devices illustrated here.

(Stokes shift)

In this embodiment, the Stokes shift of the third compound as the fluorescent material is preferably 25 nm or less, and more preferably 20 nm or less.

In this embodiment, the Stokes shift of the third compound as the fluorescent material is preferably 5 nm or more, and more preferably 10 nm or more.

The excitation energy can be reduced when the third compound has a Stokes shift of 20 nm or less.

When the third compound has a Stokes shift of 10 nm or more, self-absorption can be suppressed and efficiency loss can be reduced.

Stokes shift can be measured by the method described below. Prepare a sample for measurement by dissolving the compound to be measured in toluene at a concentration of 2.0 × 10 ^-5 mol/L. The measurement sample placed in a quartz cell is irradiated with continuous light in the ultraviolet-visible region at room temperature (300K), and the absorption spectrum (vertical axis: absorbance, horizontal axis: wavelength) is measured. A spectrophotometer can be used to measure the absorption spectrum, for example, a spectrophotometer U-3900/3900H manufactured by Hitachi High Tech Science Co., Ltd. can be used. Additionally, a sample for measurement is prepared by dissolving the compound to be measured in toluene at a concentration of 4.9×10 ^-6 mol/L. The sample for measurement placed in a quartz cell is irradiated with excitation light at room temperature (300K), and the fluorescence spectrum (vertical axis: fluorescence intensity, horizontal axis: wavelength) is measured. A spectrophotometer can be used to measure the fluorescence spectrum, for example, a spectrofluorescence spectrophotometer type F-7000 from Hitachi High-Tech Science Co., Ltd. can be used. From these absorption spectra and fluorescence spectra, the difference between the absorption maximum wavelength and the fluorescence maximum wavelength is calculated to obtain the Stokes shift (SS). The unit of Stokes shift (SS) is nm.

(Relationship between host material, sensitizing material, and fluorescent material in the light-emitting layer)

In one embodiment, the sensitizing material is the delayed fluorescent compound described above. In one embodiment, the light-emitting layer may contain a delayed fluorescent compound as a sensitizing material and may not contain a phosphorescent metal complex.

FIG. 4 is a diagram showing an example of the energy level relationship of the host material (first compound), the delayed fluorescent compound (second compound) as the sensitizing material, and the fluorescent material (third compound) in the light-emitting layer. In Figure 4, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the host material, and T1(M1) represents the lowest excited triplet state of the host material. S1(M2) represents the lowest excited singlet state of the delayed fluorescent compound, and T1(M2) represents the lowest excited triplet state of the delayed fluorescent compound. S1(M3) represents the lowest excited singlet state of the fluorescent material, and T1(M3) represents the lowest excited triplet state of the fluorescent material. The dashed arrow pointing from S1 (M2) to S1 (M3) in FIG. 4 represents the Förster type energy transfer from the lowest singlet excitation state of the delayed fluorescent compound to the lowest singlet excitation state of the fluorescent material.

As shown in FIG. 4, when a compound with a small ΔST(M2) is used as a delayed fluorescent compound, the lowest triplet excited state T1(M2) is inversely converted to the lowest singlet excited state S1(M2) by thermal energy. Intersection is possible. Then, a Förster-type energy transfer occurs from the lowest singlet excitation state S1 (M2) of the delayed fluorescent compound to the fluorescent material, and the lowest singlet excitation state S1 (M3) is generated. As a result, fluorescence emission from the lowest excited singlet state S1 (M3) of the fluorescent material can be observed. It is thought that the internal quantum efficiency can theoretically be increased to 100% by using delayed fluorescence by this TADF mechanism.

In one embodiment, it is also preferable that the lowest singlet excitation energy S ₁ (GT2) of the delayed fluorescent compound and the lowest singlet excitation energy S ₁ (D) of the fluorescent material satisfy the relationship of the following equation (Equation 4): .

S ₁ (GT2)>S ₁ (D) … (Number 4)

In one embodiment, it is also preferable that the lowest singlet excitation energy S ₁ (H1) of the host material and the lowest singlet excitation energy S ₁ (GT2) of the delayed fluorescent compound satisfy the relationship of the following equation (Equation 4A).

S ₁ (H1)>S ₁ (GT2) … (number 4A)

In one embodiment, it is also preferable that the lowest singlet excitation energy S ₁ of the host material, delayed fluorescent compound, and fluorescent material satisfies the relationship of the following equation (Equation 4B).

S ₁ (H1)>S ₁ (GT2)> S1(D) … (Number 4B)

In this embodiment, the above equation (Equation 1) when the sensitizing material is a delayed fluorescent compound is expressed by the following equation (Equation 6).

T _77K (H1)>T _77K (GT2) … (Number 6)

In one embodiment, the energy gap T _77K (GT2) at 77 [K] of the delayed fluorescent compound and the energy gap T _77K (D) at 77 [K] of the fluorescent material are expressed by the following equation (Equation 6A) It is also desirable to satisfy the relationship.

T _77K (GT2)>T _77K (D) … (Number 6A)

In one embodiment, it is also preferable that the energy gap T _77K at 77 [K] of the host material, delayed fluorescent compound, and fluorescent material satisfies the relationship of the following equation (Equation 6B).

T _77K (H1)>T _77K (GT2)>T _77K (D) … (Number 6B)

In one embodiment, the sensitizing material is a phosphorescent metal complex. In one embodiment, the light-emitting layer contains a phosphorescent metal complex as a sensitizing material and does not need to contain a delayed fluorescent compound.

FIG. 5 is a diagram showing an example of the energy level relationship among the host material (first compound), the phosphorescent metal complex (second compound) as the sensitizing material, and the fluorescent material (third compound) in the light-emitting layer. In Figure 5, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the host material, and T1(M1) represents the lowest excited triplet state of the host material. S1(M2) represents the lowest excited singlet state of the phosphorescent metal complex, and T1(M2) represents the lowest excited triplet state of the phosphorescent metal complex. S1(M3) represents the lowest excited singlet state of the fluorescent material, and T1(M3) represents the lowest excited triplet state of the fluorescent material. The dashed arrow pointing from T1 (M2) to S1 (M3) in FIG. 5 represents the dipole-type energy transfer from the lowest triplet excited state of the phosphorescent metal complex to the lowest singlet excited state of the fluorescent material.

As shown in Figure 5, when a phosphorescent metal complex is used as a sensitizing material, the lowest excited singlet state S1(M2) of the phosphorescent metal complex is the lowest excited triplet state due to spin-orbit interaction and heavy atom effect. Interterm crossing is possible with term state T1(M2). Then, a dipole-type energy transfer occurs from the lowest triplet excited state T1 (M2) of the phosphorescent metal complex to the fluorescent material, and the lowest singlet excited state S1 (M3) is generated. As a result, fluorescence emission from the lowest excited singlet state S1 (M3) of the fluorescent material can be observed. It is thought that by using this mechanism, internal quantum efficiency can theoretically be increased to 100%.

In one embodiment, the energy gap T _77K (GP2) at 77 [K] of the phosphorescent metal complex and the lowest singlet excitation energy S ₁ (D) of the fluorescent material have the relationship of the following equation (Equation 3): It is also desirable to be satisfied.

T _77K (GP2)>S ₁ (D) … (Number 3)

In this embodiment, the above equation (Equation 1) when the sensitizing material is a phosphorescent metal complex is expressed by the following equation (Equation 3A).

T _77K (H1)>T _77K (GP2) … (number 3A)

In one embodiment, the energy gap T _77K at 77 [K] of the host material and the phosphorescent metal complex and the lowest singlet excitation energy S ₁ (D) of the fluorescent material have the relationship of the following equation (Equation 3B): It is also desirable to be satisfied.

T _77K (H1)>T _77K (GP2)>S ₁ (D) … (Number 3B)

The lowest singlet excitation energy S ₁ (D) of the fluorescent material and the energy gap T _77K (D) at 77 [K] of the fluorescent material usually satisfy the relationship of the following equation (Equation 3C).

S ₁ (D)>T _77K (D) … (Number 3C)

In one embodiment, it is also preferable that the lowest singlet excitation energy S ₁ (H1) of the host material and the lowest singlet excitation energy S ₁ (GP2) of the phosphorescent metal complex satisfy the relationship of the following equation (Equation 5): .

S ₁ (H1)>S ₁ (GP2) … (Number 5)

In one embodiment, it is also preferable that the lowest singlet excitation energy S ₁ (GP2) of the phosphorescent metal complex and the lowest singlet excitation energy S ₁ (D) of the fluorescent material satisfy the relationship of the following equation (Equation 5A): do.

S ₁ (GP2)>S ₁ (D) … (Number 5A)

In one embodiment, it is also preferable that the lowest singlet excitation energy S ₁ of the host material, phosphorescent metal complex, and fluorescent material satisfies the relationship of the following equation (Equation 5B).

S ₁ (H1)>S ₁ (GP2)>S ₁ (D) … (Number 5B)

When the organic EL device of this embodiment is made to emit light, it is preferable that the fluorescent compound mainly emits light in the light emitting layer.

The maximum peak wavelength of light emitted from an organic EL device is measured in the following manner.

The spectral radiance spectrum when a voltage is applied to the organic EL element so that the current density is 10 mA/cm ² is measured with a spectral radiance meter CS-2000 (manufactured by Konica Minolta).

In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is measured, and this is taken as the maximum peak wavelength (unit: nm).

(Content rate of compound in light-emitting layer)

The content rates of the host material (first compound), sensitizing material (second compound), and fluorescent material (third compound) contained in the light-emitting layer are preferably within the following ranges, for example.

The content of the host material (first compound) in the light-emitting layer is preferably 50% by mass or more, and more preferably 70% by mass or more.

The content of the host material (first compound) in the light-emitting layer is preferably 95% by mass or less, and more preferably 90% by mass or less.

When the sensitizing material (second compound) is a delayed fluorescent compound, the content of the delayed fluorescent compound in the light emitting layer is preferably 5% by mass or more, and more preferably 10% by mass or more.

The content of the delayed fluorescent compound in the light emitting layer is preferably 50% by mass or less, and more preferably 30% by mass or less.

When the sensitizing material (second compound) is a phosphorescent metal complex, the content of the phosphorescent metal complex in the light-emitting layer is preferably 5% by mass or more, and more preferably 10% by mass or more.

The content of the phosphorescent metal complex in the light-emitting layer is preferably 50% by mass or less, and more preferably 30% by mass or less.

The content of the fluorescent material (third compound) in the emitting layer is preferably 0.5% by mass or more, and more preferably 1% by mass or more.

The content of the fluorescent material (third compound) in the emitting layer is preferably 10% by mass or less, and more preferably 5% by mass or less.

The upper limit of the total content of the host material (first compound), sensitizing material (second compound), and fluorescent material (third compound) in the light emitting layer is 100% by mass. Additionally, this embodiment does not exclude that the light emitting layer contains materials other than the host material, sensitizing material, and fluorescent material. In this embodiment, the light emitting layer may contain only one type of host material or may contain two or more types of host material.

(Film thickness of light-emitting layer)

The film thickness of the light emitting layer in the organic EL device of this embodiment is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and even more preferably 10 nm or more and 50 nm or less. If the film thickness of the light-emitting layer is 5 nm or more, formation of the light-emitting layer and adjustment of chromaticity are likely to be easy, and if the film thickness of the light-emitting layer is 50 nm or less, the increase in driving voltage is likely to be suppressed.

The configuration of the organic EL device will be further explained.

(Board)

The substrate is used as a support for an organic EL device. As a substrate, for example, glass, quartz, and plastic can be used. Additionally, a flexible substrate may be used. A flexible substrate refers to a substrate that can be folded and bent (flexible), and examples include plastic substrates. Materials forming the plastic substrate include, for example, polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Additionally, an inorganic vapor deposition film can also be used.

(anode)

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

These materials are usually formed into a film by sputtering. For example, indium oxide-zinc oxide can be formed by a sputtering method by using a target to which 1 mass% or more and 10 mass% or less of zinc oxide is added to indium oxide. In addition, for example, indium oxide containing tungsten oxide and zinc oxide can be sputtered by using a target containing 0.5 mass% or more and 5 mass% or less of tungsten oxide and 0.1 mass% or more and 1 mass% or less of zinc oxide. It can be formed as In addition, it may be produced by vacuum deposition, coating, inkjet, spin coating, etc.

Among the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that is easy to inject holes (holes) regardless of the work function of the anode, so it can be selected from materials that can be used as electrode materials (e.g. Metals, alloys, electrically conductive compounds and mixtures thereof, as well as elements belonging to group 1 or 2 of the periodic table of elements can be used.

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

When the organic EL element is a bottom emission type, the anode is preferably formed of a metal material having light transparency or semi-transmission properties that transmits light from the light emitting layer. In this specification, light transparency or semi-transmission refers to the property of transmitting more than 50% (preferably more than 80%) of the light emitted from the light-emitting layer. A metal material having light transparency or semi-transparency can be appropriately selected and used from the materials listed in the above anode section.

When the organic EL element is a top emission type, the anode is a reflective electrode with a reflective layer. The reflective layer is preferably formed of a metal material having light reflection properties. In this specification, light reflectivity means the property of reflecting 50% or more (preferably 80% or more) of the light emitted from the light emitting layer. The metal material having light reflection can be appropriately selected and used from the materials listed in the above anode section.

The anode may be composed of only a reflective layer, but may also have a multilayer structure including a reflective layer and a conductive layer (preferably a transparent conductive layer). When the anode has a reflective layer and a conductive layer, it is preferable that the conductive layer is disposed between the reflective layer and the hole transport zone. The conductive layer can be appropriately selected and used from the materials listed in the above anode section.

(cathode)

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

Additionally, 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. Additionally, when using silver paste or the like, a coating method or an inkjet method can be used.

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

When the organic EL element is a bottom emission type, the cathode is a reflective electrode. The reflective electrode is preferably formed of a metal material having light reflection properties. A metal material having light reflection can be appropriately selected and used from the materials listed in the above cathode section.

When the organic EL element is a top emission type, the cathode is preferably formed of a metal material having light transparency or semi-transparency that transmits light from the light emitting layer. A metal material having light transparency or semi-transparency can be appropriately selected and used from the materials listed in the above cathode section.

The organic EL device according to this embodiment may be a bottom emission type organic EL device. Additionally, the organic EL device according to this embodiment may be a top emission type organic EL device.

When the organic EL element is a bottom emission type, it is preferable that the anode is a light-transmitting electrode with light transparency, and the cathode is a light-reflecting electrode with light reflection.

When the organic EL element is a top emission type, it is preferable that the anode is a light-reflective electrode with light reflection properties, and the cathode is a light-transmitting electrode with light transparency.

(capping layer)

When the organic EL device is a top emission type, the organic EL device is usually provided with a capping layer on top of the cathode.

The capping layer may contain at least one compound selected from the group consisting of, for example, polymer compounds, metal oxides, metal fluorides, metal borides, silicon nitride, and silicon compounds (silicon oxide, etc.).

Additionally, the capping layer may contain at least one compound selected from the group consisting of aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, and dibenzofuran derivatives.

Additionally, a laminate in which layers containing these materials are laminated can also be used as a capping layer.

(hole injection layer)

The hole injection layer is a layer containing a material with high hole injection properties. As materials with high hole injection properties, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. can be used.

In addition, substances with high hole injection properties include 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviated name: TDATA), a low molecular weight organic compound, and 4,4',4' '-Tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated name: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]bis Phenyl (abbreviated name: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviated name: DNTPD) , 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviated name: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N -Phenylamino]-9-phenylcarbazole (abbreviated name: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated name: Aromatic amine compounds such as PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviated name: PCzPCN1), etc. can also be mentioned. .

Additionally, as a material with high hole injection properties, high molecular compounds (oligomers, dendrimers, polymers, etc.) can be used. For example, poly(N-vinylcarbazole) (abbreviated name: PVK), poly(4-vinyltriphenylamine) (abbreviated name: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino) )phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated name: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine]( Polymer compounds such as (abbreviated name: Poly-TPD) can be mentioned. In addition, polymer compounds to which acids are added, such as poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid) (PEDOT/PSS) and polyaniline/poly(styrenesulfonic acid) (PAni/PSS), can be used.

(hole transport layer)

The hole transport layer is a layer containing a material with high hole transport properties. For the hole transport layer, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated name: NPB) or N,N'-bis(3-methylphenyl)-N,N'- Diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated name: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated name: BAFLP) ), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviated name: DFLDPBi), 4,4',4''-tris (N ,N-diphenylamino)triphenylamine (abbreviated name: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated name: MTDATA), 4 Aromatic amine compounds such as ,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviated name: BSPB), etc. can be used. The materials mentioned here are mainly materials with a hole mobility of 10 ^-6 cm ² /Vs or more.

For the hole transport layer, carbazole derivatives such as CBP, CzPA, and PCzPA, or anthracene derivatives such as t-BuDNA, DNA, and DPAnth may be used. High molecular compounds such as poly(N-vinylcarbazole) (abbreviated name: PVK) or poly(4-vinyltriphenylamine) (abbreviated name: PVTPA) can also be used.

However, materials other than these may be used as long as they have higher hole transport properties than electrons. Additionally, the layer containing a material with high hole transport properties may be a single layer or a layer containing two or more layers made of the material.

(electron transport layer)

The electron transport layer is a layer containing a material with high electron transport properties. The electron transport layer contains 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzoimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymers. Compounds can be used. Specifically, low molecular organic compounds include Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviated name: Almq ₃ ), and bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviated name: Almq 3 ). Metal complexes such as BeBq ₂ ), BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated name: PBD), 1,3-bis[5- (ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviated name: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4- Biphenylyl)-1,2,4-triazole (abbreviated name: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1 ,2,4-triazole (abbreviated name: p-EtTAZ), vasophenanthroline (abbreviated name: BPhen), vasocuproin (abbreviated name: BCP), 4,4'-bis (5-methylbenzoxazole-2 -Heteroaromatic compounds such as stilbene (abbreviated name: BzOs) can also be used. The materials mentioned here are mainly materials with an electron mobility of 10 ^-6 cm ² /Vs or more. Additionally, materials other than those mentioned above may be used as the electron transport layer as long as the material has higher electron transport properties than hole transport properties. Additionally, the electron transport layer may be a single layer or a layer composed of two or more layers made of the above-mentioned material.

Additionally, a polymer compound may be used for the electron transport layer. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated name: PF-Py), poly[(9,9-dioctylfluor orene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated name: PF-BPy), etc. can be used.

(electron injection layer)

The electron injection layer is a layer containing a material with high electron injection properties. In the electron injection layer, alkali metals such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), lithium oxide (LiOx), etc. Earth metals or their compounds can be 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. Additionally, in this case, electron injection from the cathode can be performed more efficiently.

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

(Layer formation method)

The method for forming each layer of the organic EL device according to any of the above-described embodiments is not limited other than those specifically mentioned above, but may include dry film forming methods such as vacuum deposition, sputtering, plasma, and ion plating methods. , known methods such as wet film forming methods such as spin coating, dipping, flow coating, and inkjet methods can be employed.

(film thickness)

The film thickness of each organic layer of the organic EL device according to this embodiment is not limited except as specifically mentioned above. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and if the film thickness is too thick, a high applied voltage is required and efficiency deteriorates. Therefore, the film thickness of each organic layer of an organic EL device is usually several nm. A range of 1 μm is preferred.

The organic EL device according to this embodiment can be used in electronic devices such as display devices and light-emitting devices.

[Second Embodiment]

(Electronics)

The electronic device according to this embodiment is equipped with one of the organic EL elements of the above-described embodiments. Examples of electronic devices include display devices and light-emitting devices. Examples of display devices include display components (e.g., organic EL panel modules, etc.), televisions, mobile phones, tablets, and personal computers. Examples of light-emitting devices include lighting and vehicle lighting fixtures. The light emitting device can also be used in a display device, for example, as a backlight of the display device.

The display device as an electronic device according to this embodiment is preferably an organic EL display device equipped with organic EL elements as red pixels, green pixels, and blue pixels. In this organic EL display device, the red pixel is preferably the organic EL element according to the first embodiment.

[Change in embodiment]

In addition, the present invention is not limited to the above-described embodiments, and changes, improvements, etc. within the scope of achieving the purpose of the present invention are included in the present invention.

For example, the light-emitting layer is not limited to one layer, and multiple light-emitting layers may be stacked. When the organic EL element has a plurality of light-emitting layers, at least one light-emitting layer need only satisfy the conditions described in the above embodiment. For example, the other light-emitting layer may be a fluorescent light-emitting layer or a phosphorescent light-emitting layer that utilizes light emission by electron transition from a triplet excited state directly to the ground state.

In addition, when the organic EL element has a plurality of light-emitting layers, these light-emitting layers may be installed adjacent to each other, or a so-called tandem organic EL element may be used in which a plurality of light-emitting units are stacked through an intermediate layer.

Additionally, for example, a barrier layer may be provided adjacent to at least one of the anode side and the cathode side of the light emitting layer. The barrier layer is preferably disposed in contact with the light-emitting layer to block at least one of holes, electrons, and excitons.

For example, when a barrier layer is disposed in contact with the cathode side of the light emitting layer, the barrier layer transports electrons and prevents holes from reaching the layer on the cathode side (e.g., electron transport layer) rather than the barrier layer. When the organic EL element includes an electron transport layer, it is preferable to include the barrier layer between the light emitting layer and the electron transport layer.

Additionally, when a barrier layer is disposed in contact with the anode side of the light emitting layer, the barrier layer transports holes and prevents electrons from reaching the layer on the anode side (for example, a hole transport layer) rather than the barrier layer. When the organic EL device includes a hole transport layer, it is preferable to include the barrier layer between the light emitting layer and the hole transport layer.

Additionally, a barrier layer may be installed adjacent to the light-emitting layer to prevent excitation energy from leaking from the light-emitting layer to the surrounding layers. Excitons generated in the light-emitting layer are prevented from moving from the barrier layer to layers on the electrode side (eg, electron transport layer and hole transport layer, etc.).

It is preferable that the light emitting layer and the barrier layer are joined.

In addition, the specific structure and shape in implementing the present invention may be different structures within the range of achieving the purpose of the present invention.

Example

Hereinafter, the present invention will be described in more detail through examples. The present invention is not limited to these examples at all.

<Compound>

Host material used for manufacturing the organic EL devices according to Examples 1 to 10 and Comparative Example 1 (a first material comprising one or more partial structures selected from the group consisting of partial structures represented by general formulas (101) to (118) The structure of the compound) is shown below.

The structure of the sensitizing material (second compound (phosphorescent metal complex) represented by General Formula (21)) used in the production of the organic EL device according to Examples 1, 3 to 10 and Comparative Example 1 is shown below.

The structure of the sensitizing material (second compound (delayed fluorescent compound) represented by general formula (H1)) used in the production of the organic EL device according to Example 2 is shown below.

The structure of the fluorescent material (third compound) represented by the general formula (31) or (32) used in the production of the organic EL devices according to Examples 1 to 10 is shown below.

The structure of the comparative compound used to manufacture the organic EL device according to Comparative Example 1 is shown below.

The structures of other compounds used in the production of organic EL devices according to Examples 1 to 10 and Comparative Example 1 are shown below.

<Manufacturing of organic EL devices (1)>

An organic EL device was manufactured and evaluated as follows.

(Example 1)

A 25 mm x 75 mm x 1.1 mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatech Co., Ltd.) was ultrasonic cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 1 minute. The ITO film thickness was set to 130 nm.

The glass substrate with a transparent electrode line after cleaning is mounted on a substrate holder of a vacuum deposition apparatus, and the transparent electrode is first covered on the side where the transparent electrode line is formed, thereby co-depositing compound HT-a and compound HA. Thus, a hole injection layer with a film thickness of 10 nm was formed. The proportion of compound HT-a in the hole injection layer was set to 97 mass%, and the ratio of compound HA was set to 3 mass%.

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

Next, compound HT-b was deposited on the first hole transport layer to form a second hole transport layer with a film thickness of 5 nm.

Next, compound EBL-a was deposited on the second hole transport layer to form a third hole transport layer (also referred to as an electron barrier layer) with a film thickness of 5 nm.

Next, on the third hole transport layer, compound Host-a as a host material (first compound), compound STZ-a as a sensitizing material (phosphorescent metal complex (second compound)), and a fluorescent material (third compound) ) was co-deposited with the compound BD-A to form a light emitting layer with a film thickness of 30 nm. The ratio of the compound Host-a in the light emitting layer was set to 74 mass%, the ratio of the compound STZ-a was set to 25 mass%, and the ratio of the compound BD-A was set to 1 mass%.

Next, compound ET-a was deposited on the light-emitting layer to form a hole barrier layer with a thickness of 10 nm.

Next, compound ET-b was deposited on the hole barrier layer to form an electron transport layer with a film thickness of 20 nm.

Next, LiF was deposited on the electron transport layer to form an electron injection layer with a film thickness of 1 nm.

Then, metal aluminum (Al) was deposited on the electron injection layer to form a metal Al cathode with a film thickness of 50 nm.

As described above, the organic EL device according to Example 1 was manufactured. The device configuration of the organic EL device according to Example 1 is briefly expressed as follows.

ITO(130)/HT-a:HA(10,97%:3%)/HT-a(80)/HT-b(5)/EBL-a(5)/Host-a:STZ-a:BD -A(30,74%:25%:1%)/ET-a(10)/ET-b(20)/LiF(1)/Al(50)

Additionally, in the above device configuration, the numbers in parentheses indicate the film thickness (unit: nm). Similarly, among the above device configurations, the number in parentheses (97%:3%) represents the ratio (mass %) of compound HT-a and compound HA in the hole injection layer, and the number in percent (74%:25) represents the ratio (mass %) of compound HT-a and compound HA in the hole injection layer. %:1%) represents the ratio (mass %) of compound HOST-a, compound STZ-a, and compound BD-A in the light emitting layer. Hereinafter, the same notation is used.

(Example 2)

The organic EL device of Example 2 is obtained by changing the second compound STZ-a (phosphorescent metal complex) as the sensitizing material used in the light-emitting layer of Example 1 to the compound STZ-b (delayed fluorescent compound) shown in Table 1. Other than that, it was produced in the same manner as in Example 1.

(Examples 3 to 8)

The organic EL devices of Examples 3 to 8 were produced in the same manner as Example 1, except that the compound Host-a as the host material used in the light emitting layer of Example 1 was changed to the compound shown in Table 1. .

(Example 9)

In the organic EL device of Example 9, the compound Host-a as the host material used in the light emitting layer of Example 1 was changed to two types of first compounds, compounds Host-h and Host-i, as shown in Table 1. The proportion of compound Host-h in the emitting layer is 37 mass%, the proportion of compound Host-i is 37 mass%, the proportion of compound STZ-a is 25 mass%, and the proportion of compound BD-A is set to 37 mass%. It was produced in the same manner as in Example 1, except that the ratio was set to 1% by mass.

(Example 10)

The organic EL device of Example 10 was the same as Example 1 except that the compound BD-A as the fluorescent material (third compound) used in the light-emitting layer of Example 1 was changed to the compound BD-B shown in Table 1. It was produced in this way.

(Comparative Example 1)

The organic EL device of Comparative Example 1 was prepared in Example 1 except that the compound BD-A as the fluorescent material (third compound) used in the light-emitting layer of Example 1 was changed to the compound Ref-BD-X shown in Table 1. It was produced in the same way.

<Evaluation of organic EL devices>

The following evaluation was performed on the produced organic EL device. The evaluation results are shown in Table 1. Additionally, the lowest singlet excitation energy S ₁ and energy gap T _77K of the compounds used in the light-emitting layer of each example are also shown in Table 1.

(External Quantum Efficiency EQE)

The spectral radiance spectrum when a voltage was applied to the manufactured organic EL device so that the current density was 10.00 mA/cm ² was measured with a spectral radiance meter CS-2000 (manufactured by Konica Minolta Co., Ltd.). From the obtained spectral radiation luminance spectrum, the external quantum efficiency EQE (unit: %) was calculated assuming that Lambertian radiation was performed. “EQE (relative value)” (unit: %) was calculated based on the measured value of EQE in each example and the following formula (number 1X).

EQE (relative value) = (EQE of each example/EQE of Comparative Example 1) x 100... (Can be 1X)

(CIE1931 chromaticity)

The CIE1931 chromaticity coordinates (x, y) when a voltage was applied to the organic EL device so that its current density was 10.00 mA/cm ² were measured with a spectroscopic radiance meter CS-2000 (manufactured by Konica Minolta Co., Ltd.). .

As shown in Table 1, the organic EL devices of Examples 1 to 10 contain a third compound represented by the general formula (31) or (32) as a host material, a sensitizing material, and a fluorescent material in the light emitting layer, Compared to the organic EL device of Comparative Example 1, it emitted light with high efficiency and high color purity.

<Evaluation of compounds>

The following evaluation was performed on the compound.

(lowest excitation singlet energy S ₁ )

A 10 μmol/L toluene solution of the compound to be measured was prepared, placed in a quartz cell, and the absorption spectrum of this sample (vertical axis: absorption intensity, abscissa: wavelength) was measured at room temperature (300 K). A tangent line was drawn on the long-wavelength side of the absorption spectrum, and the wavelength λedge [nm] at the intersection of the tangent line and the horizontal axis was substituted into the conversion equation (F2) shown below to calculate the lowest singlet excitation energy.

Conversion formula (F2): S ₁ [eV]=1239.85/λedge

A spectrophotometer manufactured by Hitachi (device name: U3310) was used as an absorption spectrum measurement device.

The tangent line to the fall on the long wavelength side of the absorption spectrum is drawn as follows. When moving over the spectrum curve in the long-wavelength direction from the maximum value on the longest wavelength side among the maximum values of the absorption spectrum, consider the tangent line at each point on the curve. The slope of this tangent line decreases as the curve descends (i.e., as the value of the vertical axis decreases), and then increases repeatedly. At the point where the slope value takes the minimum value on the longest wavelength side (excluding the case where the absorbance is 0.1 or less), the tangent line drawn is taken as the tangent line to the descent of the long wavelength side of the absorption spectrum.

In addition, the maximum point with an absorbance value of 0.2 or less is not included in the maximum value on the longest wavelength side.

(Energy gap T _77K at 77[K])

Dissolve the compound to be measured in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) to a concentration of 10 μmol/L to obtain a solution, and place this solution in a quartz cell as a measurement sample. I did it. For this measurement sample, measure the phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) at a low temperature (77 [K]), draw a tangent line for the rise on the short wavelength side of this phosphorescence spectrum, and draw a tangent line and Based on the wave length λedge [nm] of the intersection of the horizontal axes, the energy amount calculated from the following conversion equation (F1) was set to the energy gap T _77K at 77 [K].

Conversion formula (F1): T _77K [eV]=1239.85/λ _edge

The tangent line for the rise of the short wavelength side of the phosphorescence spectrum is drawn as follows. When moving along the spectrum curve from the short wavelength side of the phosphorescence spectrum to the maximum value on the shortest wavelength side among the extreme values of the spectrum, consider the tangent line at each point on the curve toward the long wavelength side. This tangent line increases in slope as the curve rises (i.e., as the longitudinal axis increases). The tangent line drawn at the point where the value of this slope takes the maximum value (that is, the tangent line at the inflection point) is taken as the tangent line to the rise of the short wavelength side of the phosphorescence spectrum.

In addition, the local maximum point with a peak intensity of 15% or less of the maximum peak intensity of the spectrum is not included in the local maximum on the shortest wavelength side described above, and the slope value closest to the local maximum on the shortest wavelength side takes the local maximum. The drawn tangent line is taken as the tangent line to the rise of the short wavelength side of the phosphorescence spectrum.

For the measurement of phosphorescence, an F-4500 type spectrofluorescence meter manufactured by Hitachiha Technology Co., Ltd. was used.

(ΔST)

ΔST=S ₁ -T _77K was calculated based on the measured values of the lowest singlet excitation energy S ₁ and energy gap T _77K . The ΔST of compound STZ-b was 0.03 eV.

(Delayed fluorescence of compounds)

Delayed fluorescence was confirmed by measuring transient PL using the device shown in Figure 2. The compound STZ-b was dissolved in toluene, and a diluted solution with an absorbance of 0.05 or less at the excitation wavelength was prepared to eliminate the contribution of self-absorption. Additionally, in order to prevent quenching due to oxygen, the sample solution was frozen and degassed and then enclosed in a cell with a cover under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon.

The fluorescence spectrum of the sample solution was measured with a spectrofluorometer FP-8600 (manufactured by Nippon Bunko Co., Ltd.), and the fluorescence spectrum of the ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. Using the fluorescence area intensity of both spectra, Morris et al. J. Phys. The overall fluorescence quantum yield was calculated using equation (1) in Chem.80 (1976) 969.

Prompt luminescence (immediate luminescence), which is observed immediately in this excited state after being excited with pulsed light (light irradiated from a pulse laser) of a wavelength absorbed by the compound STZ-b, and which is not observed immediately after said excitation; There is delay emission that is observed later. Delayed fluorescence in this embodiment means that the amount of delay emission (delayed emission) is 5% or more relative to the amount of prompt emission (immediate emission). Specifically _, when the amount of Prompt light emission (immediate light emission) is set to X _P and the amount of Delay light emission (delayed light emission ₎ is set to X _D , it means that the value of

The amount and ratio of prompt emission and delay emission can be obtained by the same method as described in “Nature 492, 234-238, 2012” (Reference 1). Additionally, the device used to calculate the amount of prompt light emission and delay light emission is not limited to the device described in Reference 1 or the device described in FIG. 2.

Regarding compound STZ-b, it was confirmed that the amount of delay emission (delayed emission) was 5% or more relative to the amount of prompt emission (immediate emission). Specifically, for compound STZ-b, the value of X _D /X _P was 0.05 or more.

(Fluorescence emission maximum peak wavelength λ _FL and emission spectrum half width FWHM)

The compound to be measured was dissolved in toluene to prepare a solution of 5.0 × 10 ^-6 mol/L. The obtained solution is placed in a quartz cell (optical path length 1.0 cm) and excited at 400 nm using a fluorescence spectrum measuring device “Spectrofluorescence Meter FP-8300” (manufactured by Nippon Bunko Co., Ltd.). Maximum fluorescence emission peak. The wavelength λ _FL (unit: nm) and the emission spectrum full width at half maximum FWHM (unit: nm) were measured.

(Stokes Shift)

A sample for measurement was prepared by dissolving the compound to be measured in toluene at a concentration of 2.0 × 10 ^-5 mol/L. The absorption spectrum (vertical axis: absorbance, horizontal axis: wavelength) was measured by irradiating continuous light in the ultraviolet-visible region at room temperature (300K) to the measurement sample placed in a quartz cell. To measure the absorption spectrum, a spectrophotometer U-3900/3900H manufactured by Hitachi High Tech Sciences was used. Additionally, the compound to be measured was dissolved in toluene at a concentration of 4.9×10 ^-6 mol/L to prepare a sample for measurement. The sample for measurement placed in a quartz cell was irradiated with excitation light at room temperature (300K) to measure the fluorescence spectrum (vertical axis: fluorescence intensity, horizontal axis: wavelength). To measure the fluorescence spectrum, a spectrofluorescence spectrophotometer type F-7000 from Hitachi High-Tech Science was used.

From these absorption spectra and fluorescence spectra, the difference between the maximum absorption wavelength and the maximum fluorescence wavelength was calculated to determine the Stokes shift (SS). The unit of Stokes shift (SS) was nm.

The maximum peak wavelength (λ _FL ) of compound BD-A was 448 nm, the emission spectrum full width at half maximum (FWHM) was 19 nm, and the Stokes shift was 11 nm.

The maximum peak wavelength (λ _FL ) of compound BD-B was 459 nm, the full width at half maximum (FWHM) of the emission spectrum was 22 nm, and the Stokes shift was 14 nm.

The maximum peak wavelength (λ _FL ) of compound Ref-BD-X was 455 nm, the emission spectrum full width at half maximum (FWHM) was 35 nm, and the Stokes shift was 29 nm.

Claims (31)

anode,
cathode,
Comprising a light-emitting layer disposed between the anode and the cathode,
The light-emitting layer contains a host material, a sensitizing material, and a fluorescent material,
The host material is a first compound containing one or more partial structures selected from the group consisting of partial structures represented by the following general formulas (101) to (118) in one molecule,
The sensitizing material is one or more compounds selected from the group consisting of phosphorescent metal complexes and delayed fluorescent compounds,
The fluorescent material is one or more compounds selected from the group consisting of third compounds represented by the following general formula (31) or (32),
The host material, the sensitizing material, and the fluorescent material are different compounds,
The energy gap T _77K (H1) at 77 [K] of the host material and the energy gap T _77K (G2) at 77 [K] of the sensitizing material satisfy the relationship of the following equation (Equation 1), Organic electroluminescence device.
T _77K (H1)>T _77K (G2) … (Number 1)

(In the above general formula (101),
A ₁₁ to _{A 16} are each independently a nitrogen atom, CR ₁₁ , or a carbon atom bonded to another atom or other structure in the molecule of the first compound,
However, at least one of A ₁₁ to _{A 16} is a carbon atom bonded to another atom or other structure in the molecule of the first compound,
When there is a plurality of R ₁₁ , the plurality of R ₁₁ is the same as or different from each other, and at least one set of two or more adjacent R 11s among the plurality of R ₁₁ is present,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
In the general formula (102),
A ₁ to _{A 4} are each independently a nitrogen atom, CR ₁₂ , or a carbon atom bonded to another atom or other structure in the molecule of the first compound,
R ₁₂ is each independently a hydrogen atom or a substituent, or one or more groups of adjacent R ₁₂ are bonded to each other to form a ring,
When there is a plurality of R ₁₂ , the plurality of R ₁₂ are the same or different from each other, and at least one set of two or more adjacent R _12s is present,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
X ₁₀ is NR ₁₃ , C(R ₁₄ )(R ₁₅ ), Si(R ₁₆ )(R ₁₇ ), oxygen atom, sulfur atom, nitrogen bonded to another atom or other structure in the molecule of the first compound. atom, R ₁₈ and a carbon atom each bonding to another atom or other structure in the molecule of the first compound, or R ₁₉ and each bonding to another atom or other structure in the molecule of the first compound It is a silicon atom,
However, at least one of the carbon atom for A ₁ to _{A 4} , the nitrogen atom for X ₁₀ , _{the carbon atom for X 10 and} the silicon atom for combine with other atoms or other structures,
A group consisting of R ₁₄ and R ₁₅ ,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
A group consisting of R ₁₆ and R ₁₇ ,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
In the general formula (103),
A composition consisting of R ₁₁₅ and R ₁₁₆ ,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
In the general formulas (101) to (104),
R ₁₁ , R ₁₂ , R ₁₄ , R 15 , R ₁₆ , R ₁₇ , _{R 115 and} R ₁₁₆ , and R which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring ₁₃ , R ₁₈ , R ₁₉ and R ₁₁₇ are each independently
hydrogen atom,
A substituted or unsubstituted alkyl group with 1 to 50 carbon atoms,
A substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
-A group represented by Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),
A group represented by -O-(R ₉₀₄ ),
A group represented by -S-(R ₉₀₅ ),
A group represented by -N(R ₉₀₆ )(R ₉₀₇ ),
A group represented by -C(=O)R ₉₀₈ ,
-The group represented by COOR ₉₀₉ ,
A group represented by -P(=O)(R ₉₁₀ )(R ₉₁₁ ),
A group represented by -P(=O)(OR ₉₁₂ )(OR ₉₁₃ ),
A group represented by -Ge(R ₉₁₄ )(R ₉₁₅ )(R ₉₁₆ ),
-A group represented by B(R ₉₁₇ )(R ₉₁₈ ),
Substituted or unsubstituted aralkyl group with 7 to 50 carbon atoms,
halogen Atom,
Cyanogi,
nitro group,
A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or
It is a substituted or unsubstituted heterocyclic group with 5 to 50 ring atoms,
In the above general formulas (103) to (118),
* is a binding site with another atom or other structure in the molecule of the first compound,
When the first compound has a plurality of partial structures each represented by the general formulas (101) to (104),
A plurality of partial structures represented by the general formula (101) are the same or different from each other,
A plurality of partial structures represented by the general formula (102) are the same or different from each other,
A plurality of partial structures represented by the general formula (103) are the same or different from each other,
A plurality of partial structures represented by the general formula (104) are the same or different from each other.)
(In the first compound, R ₉₀₁ to R ₉₁₈ are each independently
hydrogen atom,
Substituted or unsubstituted alkyl group with 1 to 50 carbon atoms,
A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or
It is a substituted or unsubstituted heterocyclic group with 5 to 50 ring atoms,
When there is a plurality of R ₉₀₁ , the plurality of R ₉₀₁ are the same or different from each other,
When there is a plurality of R ₉₀₂ , the plurality of R ₉₀₂ are the same or different from each other,
When there is a plurality of R ₉₀₃ , the plurality of R ₉₀₃ are the same or different from each other,
When there is a plurality of R ₉₀₄ , the plurality of R ₉₀₄ are the same or different from each other,
When there is a plurality of R ₉₀₅ , the plurality of R ₉₀₅ are the same or different from each other,
When there is a plurality of R ₉₀₆ , the plurality of R ₉₀₆ are the same or different from each other,
When there is a plurality of R ₉₀₇ , the plurality of R ₉₀₇ are the same or different from each other,
When there is a plurality of R ₉₀₈ , the plurality of R ₉₀₈ are the same or different from each other,
When there is a plurality of R ₉₀₉ , the plurality of R ₉₀₉ are the same or different from each other,
When there is a plurality of R ₉₁₀ , the plurality of R ₉₁₀ are the same or different from each other,
When there is a plurality of R ₉₁₁ , the plurality of R ₉₁₁ are the same as or different from each other,
When there is a plurality of R ₉₁₂ , the plurality of R ₉₁₂ are the same or different from each other,
When there is a plurality of R ₉₁₃ , the plurality of R ₉₁₃ are the same or different from each other,
When there is a plurality of R ₉₁₄ , the plurality of R ₉₁₄ are the same or different from each other,
When a plurality of R _915s exist, the plurality of R _915s are the same or different from each other,
When there is a plurality of R ₉₁₆ , the plurality of R ₉₁₆ are the same or different from each other,
When there is a plurality of R ₉₁₇ , the plurality of R ₉₁₇ are the same or different from each other,
When there is a plurality of R ₉₁₈ , the plurality of R ₉₁₈ are the same or different from each other.)

[(In the general formula (31) above,
C ₁ ring and D ₁ ring are,
are joined to each other by a single bond, or
bonded to each other through O, S, NR ₃₃ , Si(R ₃₄ )(R ₃₅ ) or C(R ₃₇ )(R ₃₈ ) or without bonding to each other,
The C 1 ring and the D 1 ring which are not bonded to each other by a single bond and are not bonded to each other through O, S _, NR ₃₃ , Si(R ₃₄ )(R ₃₅ ) or C ₍ R ₃₇ )(R ₃₈ ), And A ₁ ring and B ₁ ring are each independently
A substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 60 carbon atoms, or
It is a substituted or unsubstituted heterocycle with 5 to 60 ring atoms,
The substituent of R _E or R _E is,
It combines with at least one of the A ₁ ring, the substituent of the A ₁ ring, the B ₁ ring, and the substituent of the B ₁ ring to form a substituted or unsubstituted monocycle, or
Combined with at least one of the A ₁ ring, the substituent of the A ₁ ring, the B ₁ ring, and the substituent of the B ₁ ring to form a substituted or unsubstituted condensed ring, or
It does not combine with the A ₁ ring, the substituent of the A ₁ ring, the B ₁ ring, and the substituent of the B ₁ ring.)
(In the above general formula (32),
A ₂ ring, B ₂ ring and C ₂ ring are each independently
A substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 60 carbon atoms, or
It is a substituted or unsubstituted heterocycle with 5 to 60 ring atoms,
The D ₂ ring is a substituted or unsubstituted monocyclic ring having 5 to 7 ring atoms that may be condensed with at least one substituted or unsubstituted non-aromatic ring having 5 to 60 ring atoms,
The C ₂ ring and the D ₂ ring are condensed by sharing a single bond or double bond with each other,
A ₂ ring and D ₂ ring are,
are joined to each other by a single bond, or
bonded to each other through O, S, NR ₃₃ , Si(R ₃₄ )(R ₃₅ ) or C(R ₃₇ )(R ₃₈ ) or without bonding to each other,
The substituent of R _F or R _F is,
It combines with at least one of the A ₂ ring, the substituent of the A ₂ ring, the B ₂ ring, and the substituent of the B ₂ ring to form a substituted or unsubstituted monocycle, or
Combined with at least one of the A ₂ ring, the substituent of the A ₂ ring, the B ₂ ring, and the substituent of the B ₂ ring to form a substituted or unsubstituted condensed ring, or
It does not combine with the A ₂ ring, the substituent of the A ₂ ring, the B ₂ ring, and the substituent of the B ₂ ring.)
(In the above general formula (31) or (32),
R _E which does not combine with the A ₁ ring, the substituents of the A ₁ ring, the B ₁ ring, and the substituents of the B ₁ ring, and the A ₂ ring, the substituents of the A ₂ ring, the B ₂ ring, and the B R _F that is not bonded to the substituent of _{the 2} ring is each independently
hydrogen atom,
A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,
A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,
Substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 20 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms,
-CR ₃₉ = Iminyl group represented by N or
It is a substituted or unsubstituted alkynyl group with 2 to 20 carbon atoms,
Y _E and Y _F are each independently a single bond, O, S, NR ₃₃ , Si(R ₃₄ )(R ₃₅ ) or C(R ₃₇ )(R ₃₈ ),
When Y _E is a single bond, the B ₁ ring and the C ₁ ring are bonded or bonded through O, S, NR ₃₃ , Si(R ₃₄ )(R ₃₅ ) or C(R ₃₇ )(R ₃₈ ) without doing,
When Y _F is a single bond, the B ₂ ring and the C ₂ ring are bonded or bonded through O, S, NR ₃₃ , Si (R ₃₄ ) (R ₃₅ ) or C (R ₃₇ ) (R ₃₈ ) without doing,
R ₃₄ and R ₃₅ are,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
R ₃₇ and R ₃₈ are,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
In the general formula (31), R ₃₃ , R ₃₄ , R ₃₅ , R ₃₇ and R ₃₈ are each independently
Combined with at least one of the A ₁ ring, the B ₁ ring, and the C ₁ ring to form a substituted or unsubstituted monocycle, or
Combined with at least one of the A ₁ ring, the B ₁ ring, and the C ₁ ring to form a substituted or unsubstituted condensed ring, or
Not bonded to the A ₁ ring, the B ₁ ring, and the C ₁ ring,
In the general formula (32), R ₃₃ , R ₃₄ , R ₃₅ , R ₃₇ and R ₃₈ are each independently
Combined with at least one of the A ₂ ring, the B ₂ ring, and the C ₂ ring to form a substituted or unsubstituted monocycle, or
Combined with at least one of the A ₂ ring, the B ₂ ring, and the C ₂ ring to form a substituted or unsubstituted condensed ring, or
Not bonded to the A ₂ ring, the B ₂ ring and the C ₂ ring,
R ₃₉ , and R ₃₃ , R ₃₄ , R ₃₅ , R ₃₇ and R ₃₈ which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently
A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,
A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or
It is a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,
When there is a plurality of R ₃₃ , the plurality of R ₃₃ are the same or different from each other,
When there is a plurality of R ₃₄ , the plurality of R ₃₄ are the same or different from each other,
When there is a plurality of R ₃₅ , the plurality of R ₃₅ are the same or different from each other,
When there is a plurality of R ₃₇ , the plurality of R ₃₇ are the same or different from each other,
When there is a plurality of R ₃₈ , the plurality of R ₃₈ are the same or different from each other.)] The organic electroluminescence device according to claim 1, wherein the compound represented by the general formula (31) is a compound represented by the following general formula (35).

(In the above general formula (35),
A group consisting of two or more adjacent elements from R ¹ to ^{R 3} , a group consisting of two or more adjacent elements from R ⁴ to ^{R 6} , a group consisting of two or more adjacent elements from R ¹² to ^{R 15} , and a group consisting of two or more adjacent elements from R 4 to R ⁶ . Among ¹⁹ , at least 1 set of groups consisting of 2 or more adjacent items,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
One or more sets of groups consisting of two or more adjacent R ⁷ to R ¹¹ ,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
The joint price of R ⁷ and R ⁶ ,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
The joint price of R ¹¹ and R ¹² ,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
R ¹ to ^{R 19} that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently
hydrogen atom,
A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,
A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,
Substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 20 carbon atoms,
Cyanogi,
N(R ²² ) ₂ ;
OR ²⁰ ,
SR ²⁰ ,
B(R ²¹ ) ₂ ;
SiR ²⁴ R ²⁵ R ²⁶ or
It is a halogen atom,
At least one set of groups consisting of two R ^22s and two sets of R ^21s ,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
R ²⁰ combines with at least one of adjacent R ¹ to ^{R 19} to form a substituted or unsubstituted monocycle, or combines with each other to form a substituted or unsubstituted condensed ring, or does not combine with each other,
R ²¹ each independently combines with at least one of adjacent R ¹ to ^{R 19} to form a substituted or unsubstituted monocycle, or combines with each other to form a substituted or unsubstituted condensed ring, or does not combine with each other. ,
R ²² each independently combines with at least one of adjacent R ¹ to ^{R 19} to form a substituted or unsubstituted monocycle, or combines with each other to form a substituted or unsubstituted condensed ring, or does not combine with each other. ,
R ²⁰ to ^{R 22} that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently
A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,
A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or
It is a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,
The combination of two adjacent R ²⁴ and R ²⁵ ,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
R ²⁶ , and R ²⁴ and R ²⁵ , which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring, are each independently
A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,
A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or
It is a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms.) The organic electroluminescent device according to claim 2, wherein the compound represented by the general formula (31) is any one compound selected from the group consisting of compounds represented by the following general formulas (351), (352), and (353). Nessence element.

(In the general formulas (351) and (352),
A group consisting of two or more adjacent elements from R ¹ to ^{R 3} , a group consisting of R ⁴ and R ⁵ , a group consisting of two or more adjacent elements from R ⁸ to ^{R 11} , and a group consisting of two or more adjacent elements from R ¹² to R ¹⁵ . A group consisting of two or more adjacent R ¹⁶ to R ¹⁹ , at least one set of groups consisting of
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
R ¹ to R ⁵ and R ⁸ to ^{R 19} that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently R ¹ in the general formula (35) Same as ~R ⁵ and R ⁸ ~R ^19. )

(In the above general formula (353),
A group consisting of two or more adjacent elements from R ¹ to ^{R 3} , a group consisting of two or more adjacent elements from R ⁴ to R ⁶ , a group consisting of two or more adjacent elements from R ⁷ to ^{R 10} , R ¹³ to R ¹⁵ A group consisting of two or more adjacent elements among R ^{16 to R 19, and one or more sets consisting of two or more adjacent elements among R 16} to ^{R 19} ,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
R ¹ to R ¹⁰ and R ¹³ to ^{R 19} that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently R ¹ in the general formula (35) Same as ~R ¹⁰ and R ¹³ ~ ^{R 19.} ) The organic electroluminescent device according to claim 1, wherein the compound represented by the general formula (32) is a compound represented by the following general formula (322).

[(In the general formula (322) above,
A ₂ ring, B ₂ ring, C ₂ ring, R _F and Y _F are each the same as A ₂ ring, B ₂ ring, C ₂ ring, R _F and Y _F in the general formula (32),
X _F is CR ₃₂₁ or a nitrogen atom,
Z _F is CR ₃₂₂ or a nitrogen atom,
R ₃₂₁ and R ₃₂₂ are the same or different from each other,
The group consisting of R ₃₂₁ and R ₃₂₂ combine with each other to form a substituted or unsubstituted non-aromatic ring having 5 to 60 ring atoms, or do not combine with each other,
A ₂ ring and R ₃₂₁ are bonded to each other by a single bond, bonded to each other through O, S, NR ₃₃ , Si(R ₃₄ )(R ₃₅ ) or C(R ₃₇ )(R ₃₈ ) or not bonded to each other. ,
R ₃₂₂ combines with the C ₂ ring to form a substituted or unsubstituted monocyclic ring, forms a substituted or unsubstituted condensed ring, or does not combine with each other,
R ₃₂₁ and R ₃₂₂ , which do not form the substituted or unsubstituted non-aromatic group having 5 to 60 ring atoms and do not bind to the A ₂ ring and the C ₂ ring, are each independently
hydrogen atom,
A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,
A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,
Substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 20 carbon atoms,
-A group represented by Si(R ₃₈₁ )(R ₃₈₂ )(R ₃₈₃ ),
A group represented by -O-(R ₃₈₄ ),
A group represented by -S-(R ₃₈₅ ),
A group represented by -N(R ₃₈₆ )(R ₃₈₇ ),
-A group represented by B(R ₃₈₈ )(R ₃₈₉ ),
halogen atom, or
It is cyano group.)
(Among the third compounds,
A composition consisting of R ₃₈₁ and R ₃₈₂ ,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
A composition consisting of R ₃₈₆ and R ₃₈₇ ,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
A composition consisting of R ₃₈₈ and R ₃₈₉ ,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
At least one selected from the group consisting of R ₃₈₄ to _{R 389} combines with an adjacent substituent to form a substituted or unsubstituted monocycle, or combines with each other to form a substituted or unsubstituted condensed ring, or does not combine with each other. Without,
R ₃₈₃ , and R 381 , R ₃₈₂ , R ₃₈₄ , R ₃₈₅ , R ₃₈₆ and _{R 387 which} do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently
A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,
A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or
It is a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,
R ₃₈₈ and R ₃₈₉ , which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring, are each independently
A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,
A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,
Substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 20 carbon atoms,
A group represented by -O-(R ₃₈₄ ) or
It is a group represented by -N(R ₃₈₆ )(R ₃₈₇ ),
When there is a plurality of R ₃₈₁ , the plurality of R ₃₈₁ are the same or different from each other,
When there is a plurality of R ₃₈₂ , the plurality of R ₃₈₂ are the same or different from each other,
When there is a plurality of R ₃₈₃ , the plurality of R ₃₈₃ are the same or different from each other,
When there is a plurality of R ₃₈₄ , the plurality of R ₃₈₄ are the same or different from each other,
When a plurality of R ₃₈₅ is present, the plurality of R ₃₈₅ is the same as or different from each other,
When there is a plurality of R ₃₈₆ , the plurality of R ₃₈₆ is the same or different from each other,
When there is a plurality of R ₃₈₇ , the plurality of R ₃₈₇ are the same or different from each other,
When there is a plurality of R ₃₈₈ , the plurality of R ₃₈₈ are the same or different from each other,
When there is a plurality of R ₃₈₉ , the plurality of R ₃₈₉ are the same or different from each other.)] The organic electroluminescent device according to claim 4, wherein the compound represented by the general formula (32) is a compound represented by the following general formula (323).

(In the above general formula (323),
A ₂ ring and R _F are each the same as A ₂ ring and R _F in the general formula (32),
X _F and Z _F are each the same as X _F and Z _F in the above general formula (322),
A group consisting of R ₃₃₁ and R ₃₂₁ in Z _F , a group consisting of R ₃₃₆ and R _F , a group consisting of R ₃₃₆ and a substituent of R _F , a group consisting of two or more adjacent ones of R ₃₃₁ to _{R 333} , and Among R ₃₃₄ to R ₃₃₆ , at least one set of two or more adjacent pairs,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
R ₃₃₁ to _{R 336} that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently
hydrogen atom,
A substituted or unsubstituted ring-forming aryl group with 6 to 60 carbon atoms,
A substituted or unsubstituted heterocyclic group with 5 to 60 ring atoms,
Substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 20 carbon atoms,
-A group represented by Si(R ₃₈₁ )(R ₃₈₂ )(R ₃₈₃ ),
A group represented by -O-(R ₃₈₄ ),
A group represented by -S-(R ₃₈₅ ),
A group represented by -N(R ₃₈₆ )(R ₃₈₇ ),
-A group represented by B(R ₃₈₈ )(R ₃₈₉ ),
halogen atom, or
It is cyano group,
At least one selected from R ₃₈₄ to _{R 389} combines with at least one selected from adjacent R ₃₃₁ to _{R 336} to form a substituted or unsubstituted monocycle, or combines with each other to form a substituted or unsubstituted condensed ring. do not form or combine with each other.) The method according to any one of claims 1 to 5, wherein the host material has at least one partial structure represented by the general formula (101),
An organic electroluminescence element, wherein the partial structure represented by the general formula (101) is at least one selected from the group consisting of partial structures represented by the following general formulas (A11) to (A19).

(In the general formulas (A11) to (A16), A ₁₂ to A ₁₆ are each independently a nitrogen atom or CR ₁₁ , R ₁₁ is the same as R ₁₁ in the general formula (101), and * is It is a binding site with another atom or other structure in the molecule of the first compound,
In the general formulas (A17) and (A18), A ₁₁ to A ₂₂ are each independently a nitrogen atom, CR ₁₁ or a carbon atom bonded to another atom or other structure in the molecule of the first compound, and R ₁₁ is each independently the same as R ₁₁ in the general formula (101), and at least one of A ₁₁ to _{A 22} is a carbon atom bonded to another atom or another structure in the molecule of the first compound. ,
In the general formula (A19), A ₁₁ to _{A 18} are each independently a nitrogen atom or CR ₁₁ or a carbon atom bonded to another atom or other structure in the molecule of the first compound, and R ₁₁ is each is independently the same as R ₁₁ in the general formula ( ₁₀₁ ), and X ₁₁ and X ₁₂ are each independently the same as X ₁₀ in the general formula ( ₁₀₂ ), and also At least one of the carbon atom, the nitrogen atom at X ₁₁ and X ₁₂ , the carbon atom at X _{11 and} X ₁₂ , and the silicon atom at X _{11 and} combines with other atoms or other structures) The method according to any one of claims 1 to 6, wherein the host material has at least one partial structure represented by the general formula (102),
An organic electroluminescence element, wherein the partial structure represented by the general formula (102) is at least one selected from the group consisting of partial structures represented by the following general formulas (B11) to (B24).

(In the general formulas (B11) to (B16), Ax ₁ to _{Ax 4} are each independently a nitrogen atom or CR ₁₂ , and R ₁₂ is each independently the same as R ₁₂ in the general formula (102). , X ₁₀ has _the same meaning as
In the general formula (B17), Ax ₁ , Ax ₂ and Ay ₁ to _{Ay 4} are each independently a nitrogen atom or CR ₁₂ or a carbon atom bonded to another atom or other structure in the molecule of the first compound. , R ₁₂ is each independently the same as R ₁₂ in the general formula (102), and X ₁₀ is the same as X ₁₀ in the general formula (102), provided that Ax ₁ , Ax ₂ and Ay At least one of the carbon atom for ₁ to Ay ₄ , the nitrogen atom for X ₁₀ , the carbon atom for X ₁₀ , and _the silicon atom for combines with other structures,
In the general formula (B18), Ay ₁ to _{Ay 8} are each independently a nitrogen atom or CR ₁₂ or a carbon atom bonded to another atom or other structure in the molecule of the first compound, and R ₁₂ is each Independently the same as R ₁₂ in _the general formula ( ₁₀₂ ) above, X ₁₀ is _{the same} as At least one of _the nitrogen atom, _the carbon atom for

(In the general formulas (B19) to (B24), Ay ₁ to Ay ₈ and Ay ₉ to _{Ay 12} are each independently a nitrogen atom or CR ₁₂ or another atom or other structure in the molecule of the first compound. is a carbon atom bonded to, R ₁₂ is each independently the same as R ₁₂ in the general formula (102), and X ₉ and X ₁₀ are each independently the same as X ₁₀ in the general formula (102) ego,
Carbon atoms at Ay ₁ to Ay ₈ and Ay ₉ to Ay ₁₂ , nitrogen atoms at X ₉ and X ₁₀ , carbon atoms at X ₉ and X ₁₀ , and silicon atoms at X ₉ and X ₁₀ At least one of them is bonded to another atom or other structure in the molecule of the first compound.) The method according to any one of claims 1 to 7, wherein the first compound is:
Cyanogi,
amino group,
A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, and
It has at least one substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms, or
Substituted or unsubstituted benzene,
Substituted or unsubstituted naphthalene,
Substituted or unsubstituted indole,
Substituted or unsubstituted carbazole,
Substituted or unsubstituted dibenzofuran,
Substituted or unsubstituted dibenzothiophene,
Substituted or unsubstituted fluorene,
Substituted or unsubstituted silafluorene,
Substituted or unsubstituted triazine,
Substituted or unsubstituted pyrimidine,
Substituted or unsubstituted pyridine,
Substituted or unsubstituted pyridazine,
Substituted or unsubstituted pyrazine,
Substituted or unsubstituted imidazole,
Substituted or unsubstituted benzimidazole,
Substituted or unsubstituted phenanthrene, and
An organic electroluminescent device having at least one monovalent or higher residue derived from either substituted or unsubstituted triphenylene. The method of claim 8, wherein the first compound is:
has at least one cyano group, or
Substituted or unsubstituted carbazole,
Substituted or unsubstituted dibenzofuran,
Substituted or unsubstituted dibenzothiophene,
Substituted or unsubstituted fluorene,
Substituted or unsubstituted silafluorene,
Substituted or unsubstituted triazine,
Substituted or unsubstituted pyrimidine,
Substituted or unsubstituted pyridine, and
An organic electroluminescent device having at least one monovalent or higher residue derived from either substituted or unsubstituted triphenylene. The method of claim 8 or 9, wherein the first compound is,
Substituted or unsubstituted carbazole,
Substituted or unsubstituted dibenzofuran,
Substituted or unsubstituted dibenzothiophene,
Substituted or unsubstituted triazine, and
An organic electroluminescent device having at least one monovalent or higher residue derived from either substituted or unsubstituted pyrimidine. The organic electroluminescence device according to any one of claims 8 to 10, wherein the first compound has at least one monovalent or higher residue derived from substituted or unsubstituted carbazole. The organic electroluminescent device according to any one of claims 8 to 10, wherein the first compound has at least one partial structure represented by the following general formula (15).

(In the general formula (15), at least one of R ₁₅₀ to _{R 158} is a single bond bonded to another atom or other structure in the molecule of the first compound,
R ₁₅₀ ∼ R ₁₅₈ , which are not single bonds, are each independently
hydrogen atom,
Substituted or unsubstituted alkyl group with 1 to 50 carbon atoms,
A substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
-A group represented by Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),
A group represented by -O-(R ₉₀₄ ),
A group represented by -S-(R ₉₀₅ ),
A group represented by -N(R ₉₀₆ )(R ₉₀₇ ),
A group represented by -C(=O)R ₉₀₈ ,
-The group represented by COOR ₉₀₉ ,
A group represented by -P(=O)(R ₉₁₀ )(R ₉₁₁ ),
A group represented by -Ge(R ₉₁₂ )(R ₉₁₃ )(R ₉₁₄ ),
-A group represented by B(R ₉₁₅ )(R ₉₁₆ ),
Substituted or unsubstituted aralkyl group with 7 to 50 carbon atoms,
halogen Atom,
Cyanogi,
nitro group,
A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or
It is a substituted or unsubstituted heterocyclic group with 5 to 50 ring atoms.) The organic electroluminescent device according to any one of claims 1 to 5, wherein the first compound is a compound represented by the following general formula (161) or the following general formula (162).

(In the general formula (161), Ar ₁₆₁ is,
A substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 30 carbon atoms, or
It is a substituted or unsubstituted heterocycle with 5 to 30 ring atoms,
m1 is 1, 2, 3, 4, 5 or 6,
R ₁₆₁ is an electron donating group, and R ₁₆₁ is each bonded to an element constituting Ar ₁₆₁ ,
When m1 is 2 or more, a plurality of R ₁₆₁ are the same or different from each other,
However, Ar ₁₆₁ is not an electron-accepting aromatic hydrocarbon ring or heterocycle, and when Ar ₁₆₁ has a substituent, the substituent is not an electron acceptor,
In the general formula (162), Ar ₁₆₂ is,
A substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 30 carbon atoms, or
It is a substituted or unsubstituted heterocycle with 5 to 30 ring atoms,
n1 is 1, 2, 3, 4, 5 or 6,
R ₁₆₂ is an electron acceptor, and R ₁₆₂ each binds to an element constituting Ar ₁₆₂ ,
When n1 is 2 or more, a plurality of R ₁₆₂ are the same or different from each other,
However, Ar ₁₆₂ is not an electron-donating aromatic hydrocarbon ring or heterocycle, and when Ar ₁₆₂ has a substituent, the substituent is not an electron-donating group.) The method of claim 13, wherein R ₁₆₁ in the general formula (161) is each independently derived from any one of the compounds represented by the following general formulas (DN1) to (DN6) and (DN8) to (DN10). It is one or more residues or a group represented by the general formula (DN7) below,
R ₁₆₂ in the general formula (162) is each independently a monovalent or higher residue derived from any one of the compounds represented by the general formulas (AC4) to (AC18) and (AC22) to (AC23) below, or An organic electroluminescent device, which is one of the groups represented by the general formulas (AC1) to (AC3), (AC19) to (AC21) and (AC24).

(In the general formula (DN7), * represents a binding site with the elements constituting Ar ₁₆₁ , respectively.)

(In the general formula (AC1), n _A is 1, 2, or 3,
In the general formulas (AC22) to (AC23), X ₁ to X ₈ are each independently CR ₁₆₃ or a carbon atom bonded to another atom or other structure in the molecule of the first compound, provided that At least one of the _carbon atoms in _{1 to}
In the general formula ( _{AC24 )} , X _{1 to}
In the above general formulas (AC22) to (AC24), when a plurality of R ₁₆₃ is present, the plurality of R ₁₆₃ is the same as or different from each other, and at least one set of two or more adjacent R 163s among the plurality of R ₁₆₃ is present,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
R ₁₆₃ that does not form the substituted or unsubstituted monocyclic ring or does not form the substituted or unsubstituted condensed ring is each independently the same as R ₁₂ in the general formula (102),
In the general formulas (AC1) to (AC3), (AC19) to (AC21) and (AC24), * represents the binding site with the element constituting Ar ₁₆₂ , respectively.) The organic electroluminescent device according to any one of claims 1 to 5, wherein the first compound is a compound represented by the following general formula (12).

(In the above general formula (12),
Ar ₁₁ and Ar ₁₂ are each independently
A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or
It is a substituted or unsubstituted heterocyclic group with 5 to 50 ring atoms,
L ₁₁ and L ₁₂ are each independently
single bond,
A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or
It is a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,
L ₁₃ is,
A substituted or unsubstituted monocyclic hydrocarbon group with 6 or less ring-forming carbon atoms, or
It is a substituted or unsubstituted monocyclic heterocyclic group with 6 or less ring atoms,
m is 0, 1, 2 or 3, and the plurality of L ₁₃ are the same or different from each other,
X ₁ to X ₈ and Y ₁ to _{Y 8} are each independently N or CRa,
However, one of X ₅ to X ₈ and one of Y ₁ to _{Y 4} are a carbon atom bonded through L ₁₃ or a carbon atom bonded directly,
Ra is each independently
hydrogen atom,
Substituted or unsubstituted alkyl group with 1 to 50 carbon atoms,
-A group represented by Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),
halogen Atom,
A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or
It is a substituted or unsubstituted heterocyclic group with 5 to 50 ring atoms,
When there are multiple Ra's, the multiple Ra's are the same or different from each other,
The compound represented by the general formula (12) satisfies one or both of (i) and (ii) below.
(i) At least one of Ar ₁₁ and Ar ₁₂ is an aryl group having 6 to 50 ring carbon atoms substituted with a cyano group, or a heterocyclic group having 5 to 50 ring atoms substituted with a cyano group.
( _ii ) At least one of X ₁ to _{X 4} and Y ₅ to _{Y 8} is CRa, and at least one of Ra in X ₁ to It is an aryl group of ∼50 or a heterocyclic group of 5 to 50 ring atoms substituted with a cyano group.) The organic electroluminescent device according to any one of claims 1 to 5, wherein the first compound is a compound represented by the following general formula (13).

(In the above general formula (13),
X ₁₃ is an oxygen atom, a sulfur atom, or a group represented by N-Rb,
Z ₁ to _{Z 12} are each independently a nitrogen atom or a group represented by C-Rc,
Ar ₁₄ and Ar ₁₅ are each independently
A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or
It is a substituted or unsubstituted heterocyclic group with 5 to 50 ring atoms,
L ₁₄ and L ₁₅ are each independently
single bond,
A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or
It is a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,
Rb and Rc are each independently
hydrogen atom,
Substituted or unsubstituted alkyl group with 1 to 50 carbon atoms,
A substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Substituted or unsubstituted aralkyl group with 7 to 50 carbon atoms,
-A group represented by Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),
A group represented by -C(=O)R ₉₀₈ ,
-The group represented by COOR ₉₀₉ ,
A group represented by -P(=O)(R ₉₁₀ )(R ₉₁₁ ),
A group represented by -Ge(R ₉₁₂ )(R ₉₁₃ )(R ₉₁₄ ),
Cyanogi,
nitro group,
A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or
It is a substituted or unsubstituted heterocyclic group with 5 to 50 ring atoms,
When there are multiple Rcs, the multiple Rcs are the same or different from each other.) The organic electroluminescent device according to any one of claims 1 to 16, wherein the phosphorescent metal complex contains a heavy metal atom. The method according to any one of claims 1 to 17, wherein the phosphorescent metal complex is platinum (Pt), iridium (Ir), osmium (Os), ruthenium (Ru), rhodium (Rh), palladium (Pd), Selected from the group consisting of copper (Cu), silver (Ag), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm). An organic electroluminescent device comprising one or more metal atoms. The organic electroluminescence device according to any one of claims 1 to 18, wherein the phosphorescent metal complex is a compound represented by the following general formula (21).
M(L ₁ ) _n1 (L ₂ ) _n2 … (21)

(In the general formulas (21), (211), (212), (213),
M is a transition metal selected from the group consisting of a first transition metal, a second transition metal, and a third transition metal,
L ₁ is at least one type of ligand selected from the group consisting of a ligand represented by the general formula (211), a ligand represented by the general formula (212), and a ligand represented by the general formula (213),
n1 is 1, 2 or 3,
L ₂ is at least one type of ligand selected from the group consisting of monodentate ligands, bidentate ligands, and tridentate ligands,
n2 is 0, 1, 2, 3 or 4,
The CY ₁ ring, CY ₂ ring, CY ₃ ring, and CY ₄ ring are each independently selected from the group consisting of a carbocyclic group having 5 to 30 ring carbon atoms and a heterocyclic group having 1 to 30 ring carbon atoms,
Y ₁ to _{Y 4} are each independently
single bond,
double bond,
A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms,
A substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,
*aO-*b,
*aS-*b,
*aC(=O)-*b,
*aS(=O)-*b,
*aC(R ₅ )(R ₆ )-*b,
*aC(R ₅ )=C(R ₆ )-*b,
*aC(R ₅ )=*b,
*a-Si(R ₅ )(R ₆ )-*b,
*aB(R ₅ )-*b;
*aN(R ₅ )-*b, and
selected from the group consisting of *aP(R ₅ )-*b,
a1, a2 and a3 are each independently 1, 2 or 3,
a4 is 0, 1, 2, or 3, and when a4 is 0, the CY ₁ ring and the CY ₄ ring are not connected to each other,
T ₁ , T ₂ , T ₃ and T ₄ are each independently
chemical bond,
*aO-*b,
*aS-*b,
*aB(R ₇ )-*b;
*aN(R ₇ )-*b;
*aP(R ₇ )-*b;
*aC(R ₇ )(R ₈ )-*b,
*a-Si(R ₇ )(R ₈ )-*b,
*a-Ge(R ₇ )(R ₈ )-*b,
*aC(=O)-*b and
is selected from the group consisting of *aC(=S)-*b,
*a and *b are each independently bonding positions with adjacent atoms,
*1, *2, *3 and *4 are binding sites with M,
R ₁ to R ₈ are each independently
hydrogen atom,
halogen Atom,
Cyanogi,
nitro group,
amidino group,
hydrazino group,
Hydrazonogi,
Substituted or unsubstituted alkyl group with 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
A substituted or unsubstituted heterocycloalkyl group having 3 to 50 ring atoms,
A substituted or unsubstituted ring-forming cycloalkenyl group having 3 to 50 carbon atoms,
A substituted or unsubstituted heterocycloalkenyl group having 3 to 50 ring atoms,
A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms,
A substituted or unsubstituted heterocyclic group with 5 to 50 ring atoms,
Substituted or unsubstituted monovalent non-aromatic condensed polycyclic group,
Substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group,
-A group represented by Si(R ₂₅₁ )(R ₂₅₂ )(R ₂₅₃ ),
A group represented by -O-(R ₂₅₄ ),
A group represented by -S-(R ₂₅₅ ),
A group represented by -N(R ₂₅₆ )(R ₂₅₇ ),
A group represented by -C(=O)R ₂₅₈ ,
A group represented by -C(=O)(OR ₂₅₉ ),
A group represented by -S(=O) ₂ (OR ₂₆₀ ),
A group represented by -OP(=O)(OR ₂₆₁ )(OR ₂₆₂ ),
A group represented by -C(R ₂₆₃ )(R ₂₆₄ )(R ₂₆₅ ),
-A group represented by B(R ₂₆₆ )(R ₂₆₇ ),
-A group represented by P(R ₂₆₈ )(R ₂₆₉ ),
A group represented by -S(=O)(R ₂₇₀ ),
A group represented by -S(=O) ₂ (R ₂₇₁ ),
A group represented by -P(=O)(R ₂₇₂ )(R ₂₇₃ ), and
-P(=S)(R ₂₇₄ )(R ₂₇₅ ) is selected from the group represented by,
One or more sets of groups consisting of two or more adjacent R ₁ to R ₈ ,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
One or more sets of adjacent two or more _of R ₁ to R 8 and Y ₁ to _{Y 4} ,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
b1, b2, b3 and b4 are each independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10,
R ₂₅₁ to R ₂₇₅ are each independently
hydrogen atom,
halogen Atom,
A group represented by -O-(R ₂₇₆ ),
A group represented by -N(R ₂₇₇ )(R ₂₇₈ ),
Cyanogi,
nitro group,
amidino group,
hydrazino group,
Hydrazonogi,
Substituted or unsubstituted alkyl group with 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
A substituted or unsubstituted heterocycloalkyl group having 3 to 50 ring atoms,
A substituted or unsubstituted ring-forming cycloalkenyl group having 3 to 50 carbon atoms,
A substituted or unsubstituted heterocycloalkenyl group having 3 to 50 ring atoms,
A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms,
A ring-forming aryl group with 6 to 50 carbon atoms substituted with a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms,
An aryl group having 6 to 50 ring carbon atoms substituted with a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
A substituted or unsubstituted heterocyclic group with 5 to 50 ring atoms,
Substituted or unsubstituted monovalent non-aromatic condensed polycyclic group,
Substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group,
selected from the group consisting of biphenylyl group and terphenylyl group,
R ₂₇₆ to R ₂₇₈ are each independently
hydrogen atom,
Substituted or unsubstituted alkyl group with 1 to 50 carbon atoms,
A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or
It is a substituted or unsubstituted heterocyclic group with 5 to 50 ring atoms.) The method according to any one of claims 1 to 19, wherein the lowest singlet excitation energy S ₁ (GT2) of the delayed fluorescent compound and the energy gap T _77K (GT2) at 77 [K] of the delayed fluorescent compound The difference ΔST(GT2) is an organic electroluminescent element that satisfies the following equation (Equation 2).
ΔST(GT2)=S ₁ (GT2)-T _77K (GT2)<0.5 eV... (Number 2) The organic electroluminescent device according to any one of claims 1 to 20, wherein the delayed fluorescent compound is a compound represented by the following general formula (H1).

(In the above general formula (H1),
A _H has the following general formulas (a-1), (a-2), (a-3), (a-4), (a-5), (a-6), (a-7) and (a) -8) is a group having at least one partial structure selected from the group consisting of,
D _H is a group represented by the following general formula (221), (222) or (223),
L _H is,
single bond,
A substituted or unsubstituted ring-forming aryl ring having 6 to 50 carbon atoms, or
It is a substituted or unsubstituted heterocycle with 5 to 50 ring atoms,
m is 1, 2, 3, 4 or 5, and the plurality of A _H is the same or different from each other,
n is 1, 2, 3, 4 or 5, and the plurality of D _H are the same or different from each other.)

(In the general formulas (a-1) to (a-8), * each independently represents a bonding position with another atom in the molecule of the delayed fluorescent compound.)

(At least one set of two or more adjacent R ₂₁ to R ₂₈ in the general formula (221) above,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
One or more groups consisting of two or more adjacent R ₂₂₁ to R ₂₂₈ in the general formula (222) above,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
One or more groups consisting of two or more adjacent R ₂₃₁ to R ₂₃₈ in the general formula (223) above,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
R ₂₁ to _{R 28} that do not form a substituted or unsubstituted monocyclic ring in the general formula (221) and do not form a substituted or unsubstituted condensed ring, and are substituted or unsubstituted in the general formula (222) R ₂₂₁ to _{R 228} , which does not form a monocycle and does not form a substituted or unsubstituted condensed ring, and which does not form a substituted or unsubstituted monocycle in the general formula (223) and does not form a substituted or unsubstituted ring R ₂₃₁ to R ₂₃₈ that do not form a condensed ring are each independently
hydrogen atom,
Substituted or unsubstituted alkyl group with 1 to 50 carbon atoms,
A substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
-A group represented by Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),
A group represented by -O-(R ₉₀₄ ),
A group represented by -S-(R ₉₀₅ ),
A group represented by -N(R ₉₀₆ )(R ₉₀₇ ),
Substituted or unsubstituted aralkyl group with 7 to 50 carbon atoms,
A group represented by -C(=O)R ₉₀₈ ,
-The group represented by COOR ₉₀₉ ,
halogen Atom,
Cyanogi,
nitro group,
A group represented by -P(=O)(R ₉₃₁ )(R ₉₃₂ ),
A group represented by -Ge(R ₉₃₃ )(R ₉₃₄ )(R ₉₃₅ ),
-A group represented by B(R ₉₃₆ )(R ₉₃₇ ),
A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or
It is a substituted or unsubstituted heterocyclic group with 5 to 50 ring atoms,
In the general formula (222) and the general formula (223),
Ring A, Ring B, and Ring C are each independently any one ring structure selected from the group consisting of ring structures represented by the following general formulas (224) and (225),
Ring A, Ring B and Ring C are condensed with adjacent rings at any position,
p, px and py are each independently 1, 2, 3 or 4,
When p is 2, 3 or 4, the plurality of rings A are the same or different from each other,
When px is 2, 3 or 4, the plurality of rings B are the same or different from each other,
When py is 2, 3 or 4, the plurality of rings C are the same or different from each other,
* in the general formulas (221) to (223) indicates the bonding position with L _H. )

(In the above general formula (224),
r is 0, 2 or 4,
A group consisting of a plurality of R ₂₉ ,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
In the general formula (225), X _A is a sulfur atom, an oxygen atom, or C(R ₂₉₁ )(R ₂₉₂ ),
A composition consisting of R ₂₉₁ and R ₂₉₂ ,
Combine with each other to form a substituted or unsubstituted monocycle,
Combine with each other to form a substituted or unsubstituted condensed ring, or
do not combine with each other,
R ₂₉ , R ₂₉₁ and R ₂₉₂ , which do not form a substituted or unsubstituted single ring and do not form a substituted or unsubstituted condensed ring, each independently
hydrogen atom,
Substituted or unsubstituted alkyl group with 1 to 50 carbon atoms,
A substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
-A group represented by Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),
A group represented by -O-(R ₉₀₄ ),
A group represented by -S-(R ₉₀₅ ),
A group represented by -N(R ₉₀₆ )(R ₉₀₇ ),
Substituted or unsubstituted aralkyl group with 7 to 50 carbon atoms,
A group represented by -C(=O)R ₉₀₈ ,
-The group represented by COOR ₉₀₉ ,
halogen Atom,
Cyanogi,
nitro group,
A group represented by -P(=O)(R ₉₃₁ )(R ₉₃₂ ),
A group represented by -Ge(R ₉₃₃ )(R ₉₃₄ )(R ₉₃₅ ),
-A group represented by B(R ₉₃₆ )(R ₉₃₇ ),
A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or
It is a substituted or unsubstituted heterocyclic group with 5 to 50 ring atoms,
A plurality of R ₂₉ are the same or different from each other,
A plurality of R ₂₉₁ are the same or different from each other,
A plurality of R ₂₉₂ are the same or different from each other,
A plurality of X _A are the same or different from each other.)
(Among the delayed fluorescent compounds, R ₉₀₁ , R ₉₀₂ , R ₉₀₃ , R 904, R ₉₀₅ , R ₉₀₆ , R ₉₀₇ , R ₉₀₈ , R ₉₀₉ , R ₉₃₁ , R ₉₃₂ , R ₉₃₃ , _{R 934 ,} R ₉₃₅ , R ₉₃₆ and R ₉₃₇ , each independently
hydrogen atom,
Substituted or unsubstituted alkyl group with 1 to 50 carbon atoms,
A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or
It is a substituted or unsubstituted heterocyclic group with 5 to 50 ring atoms,
When there is a plurality of R ₉₀₁ , the plurality of R ₉₀₁ are the same or different from each other,
When there is a plurality of R ₉₀₂ , the plurality of R ₉₀₂ are the same or different from each other,
When there is a plurality of R ₉₀₃ , the plurality of R ₉₀₃ are the same or different from each other,
When there is a plurality of R ₉₀₄ , the plurality of R ₉₀₄ are the same or different from each other,
When there is a plurality of R ₉₀₅ , the plurality of R ₉₀₅ are the same or different from each other,
When there is a plurality of R ₉₀₆ , the plurality of R ₉₀₆ are the same or different from each other,
When there is a plurality of R ₉₀₇ , the plurality of R ₉₀₇ are the same or different from each other,
When there is a plurality of R ₉₀₈ , the plurality of R ₉₀₈ are the same or different from each other,
When there is a plurality of R ₉₀₉ , the plurality of R ₉₀₉ are the same or different from each other,
When there is a plurality of R ₉₃₁ , the plurality of R ₉₃₁ are the same or different from each other,
When there is a plurality of R ₉₃₂ , the plurality of R ₉₃₂ are the same or different from each other,
When there is a plurality of R ₉₃₃ , the plurality of R ₉₃₃ are the same or different from each other,
When there is a plurality of R ₉₃₄ , the plurality of R ₉₃₄ are the same or different from each other,
When there is a plurality of R ₉₃₅ , the plurality of R ₉₃₅ are the same or different from each other,
When there is a plurality of R ₉₃₆ , the plurality of R ₉₃₆ are the same or different from each other,
When there is a plurality of R ₉₃₇ , the plurality of R ₉₃₇ are the same or different from each other.) The organic electroluminescence device according to claim 21, wherein the delayed fluorescent compound is a compound represented by the following general formula (H10).

(In the above general formula (H10),
CN is a cyano group,
L _H is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms,
D ₁₁ and D ₁₂ are each independently a group represented by the general formula (221), (222) or (223),
m is 1, 2, 3, 4 or 5,
nx is 0, 1, 2, 3, 4 or 5,
ny is 0, 1, 2, 3, 4, or 5,
nx+ny is 1, 2, 3, 4 or 5,
D ₁₁ and D ₁₂ are the same or different from each other,
A plurality of D ₁₁ are the same or different from each other,
A plurality of D ₁₂ are the same or different from each other.) The organic electroluminescent element according to any one of claims 1 to 22, wherein the sensitizing material is the phosphorescent metal complex. The method according to claim 23, wherein the energy gap T _77K (GP2) at 77 [K] of the phosphorescent metal complex and the lowest singlet excitation energy S ₁ (D) of the fluorescent material are expressed by the following formula (Equation 3) An organic electroluminescence device that satisfies the relationship.
T _77K (GP2)>S ₁ (D) … (Number 3) The organic electroluminescent element according to any one of claims 1 to 22, wherein the sensitizing material is the delayed fluorescent compound. The method of claim 25, wherein the lowest singlet excitation energy S ₁ (GT2) of the delayed fluorescent compound and the lowest singlet excitation energy S ₁ (D) of the fluorescent material satisfy the relationship of the following equation (Equation 4): , Organic electroluminescence device.
S ₁ (GT2)>S ₁ (D) … (Wed 4) The organic electroluminescent device according to any one of claims 1 to 26, wherein the light-emitting layer contains two or more types of the first compounds having different molecular structures. The organic electroluminescent element according to any one of claims 1 to 27, wherein the host material, the sensitizing material, and the fluorescent material are contained in a single layer. The organic electroluminescent element according to any one of claims 1 to 28, wherein a hole transport layer is disposed between the anode and the light emitting layer. The organic electroluminescent element according to any one of claims 1 to 29, wherein an electron transport layer is disposed between the cathode and the light-emitting layer. An electronic device equipped with the organic electroluminescent element according to any one of claims 1 to 30.