JP2016129262A - Organic electroluminescent element and electronic device - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an organic electroluminescent element capable of improving luminous efficiency, and an electronic device including the organic electroluminescent element.SOLUTION: The organic electroluminescent element includes an anode, a light-emitting layer, and a cathode. The light-emitting layer contains a first material, a second material, and a third material. The first material is a fluorescent light-emitting material, the second material is a delayed fluorescent material, and the third material has a singlet energy larger than that of the second material.SELECTED DRAWING: None

Description

  The present invention relates to an organic electroluminescence element and an electronic apparatus.

When a voltage is applied to an organic electroluminescence element (hereinafter sometimes referred to as an organic EL element), holes from the anode and electrons from the cathode are injected into the light emitting layer. Then, in the light emitting layer, the injected holes and electrons are recombined to form excitons. At this time, singlet excitons and triplet excitons are generated at a ratio of 25%: 75% according to the statistical rule of electron spin.
Fluorescent organic EL devices that use light emitted from singlet excitons are said to have a limit of 25% internal quantum efficiency and are being applied to full-color displays such as mobile phones and TVs. In addition to singlet excitons, Therefore, further efficiency improvement using triplet excitons was expected.

  Against this background, highly efficient fluorescent organic EL elements using delayed fluorescence have been proposed and studied.

For example, a TADF (Thermally Activated Delayed Fluorescence, heat activated delayed fluorescence) mechanism has been studied. In this TADF mechanism, when a material having a small energy difference (ΔST) between a singlet level and a triplet level is used, a reverse intersystem crossing from a triplet exciton to a singlet exciton is thermally generated. It uses the phenomenon. The thermally activated delayed fluorescence is described in, for example, “Adachi Chinami, edited by“ Physical Properties of Organic Semiconductor Devices ”, Kodansha, March 22, 2012, pages 261-262”.
For example, Patent Documents 1 to 3 disclose organic EL elements using the TADF mechanism.
Patent Document 1 discloses an organic EL element including a light-emitting layer containing a compound having a small ΔST as a host material and a fluorescent compound as a dopant material. According to Patent Document 1, it is described that the internal quantum efficiency is improved by using a compound having a small ΔST as a host material and expressing the TADF mechanism in the host material.
Patent Document 2 and Patent Document 3 also disclose an organic EL device including a light emitting layer containing a specific compound as a host material and a fluorescent compound as a dopant material. According to Patent Document 2 and Patent Document 3, as in Patent Document 1, the TADF mechanism is used to improve the performance of the organic EL element.

International Publication No. 2012/133188 International Publication No. 2013/180241 Chinese Patent Application No. 10709485

  However, as an organic EL element, it is necessary to further improve the luminous efficiency.

  An object of the present invention is to provide an organic electroluminescence device capable of improving luminous efficiency. Another object of the present invention is to provide an electronic device provided with the organic electroluminescence element.

An organic electroluminescence device according to one embodiment of the present invention includes an anode, a light emitting layer, and a cathode, and the light emitting layer includes a first material, a second material, and a third material, One material is a fluorescent material, and the second material is a delayed fluorescent material, and the singlet energy of the third material is the singlet energy of the second material. The energy gap Eg _77K (M2) at 77 [K] of the second material is larger than the energy gap Eg _77K (M1) at 77 [K] of the first material, and the third material energy gap _Eg 77K in 77 [K] of the material (M3), the second greater than the energy gap _Eg 77K (M2) in 77 [K] of the material, provided that the emission layer The following compound A, the following compound B, and not the layer which contains the following compounds C.
An electronic device according to one embodiment of the present invention includes the organic electroluminescence element according to one embodiment of the present invention described above.

  ADVANTAGE OF THE INVENTION According to this invention, the organic electroluminescent element which can improve luminous efficiency can be provided.

It is a figure which shows schematic structure of an example of the organic electroluminescent element which concerns on embodiment of this invention. It is the schematic of the apparatus which measures transient PL. It is a figure which shows an example of the attenuation curve of transient PL. It is a figure which shows the relationship of the energy level and energy transfer of the 1st material in a light emitting layer, a 2nd material, and a 3rd material.

  Hereinafter, embodiments of the organic EL device of the present invention will be described.

[First embodiment]
(Element structure of organic EL element)
The configuration of the organic EL element according to the first embodiment of the present invention will be described.
The organic EL element includes an organic layer between a pair of electrodes. This organic layer is formed by laminating a plurality of layers composed of organic compounds. The organic layer may further contain an inorganic compound.
In the organic EL device of the present embodiment, at least one of the organic layers is a light emitting layer. Therefore, the organic layer may be composed of, for example, a single light emitting layer, and is employed in organic EL elements such as a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a barrier layer. It may have a layer.

In FIG. 1, schematic structure of an example of the organic EL element in this embodiment is shown.
The organic EL element 1 includes a translucent 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 includes a light emitting layer 5, a hole injection / transport layer 6 provided between the light emitting layer 5 and the anode 3, and an electron injection / transport layer provided between the light emitting layer 5 and the cathode 4. 7 In the organic EL element of the present embodiment, the light emitting layer 5 contains a first material, a second material, and a third material. The light emitting layer 5 may contain a phosphorescent metal complex. However, in the embodiment of the present invention, even if it does not contain a phosphorescent metal complex, it is possible to obtain a light emitting performance exceeding that of a conventional fluorescent element.
The above “hole injection / transport layer” means “at least one of a hole injection layer and a hole transport layer”, and “electron injection / transport layer” means “an electron injection layer and an electron transport layer”. "At least one of them". Here, when it has a positive hole injection layer and a positive hole transport layer, it is preferable that the positive hole injection layer is provided in the anode side. Moreover, when it has an electron injection layer and an electron carrying layer, it is preferable that the electron injection layer is provided in the cathode side. Further, each of the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer may be composed of a single layer, or a plurality of layers may be laminated.

(Light emitting layer)
-1st material The 1st material which concerns on this embodiment is a luminescent material of fluorescence emission.
The first material need not be particularly limited in emission color, but preferably exhibits fluorescence with a main peak wavelength of 550 nm or less, and more preferably exhibits fluorescence with a main peak wavelength of 480 nm or less. In particular, it is considered that a blue organic EL element having a problem in luminous efficiency has the maximum effect.
The main peak wavelength is the emission spectrum that maximizes the emission intensity in the measured emission spectrum of a toluene solution in which the first material is dissolved at a concentration of 10 ⁻⁵ mol / liter to 10 ⁻⁶ mol / liter. Refers to the peak wavelength.
The first material preferably exhibits blue fluorescence. Moreover, it is preferable that a 1st material is a material with a high fluorescence quantum yield.

  As the first material according to the present embodiment, a fluorescent material can be used. Specifically, for example, bisarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, bisarylaminoanthracene derivatives, aryl group-substituted anthracene derivatives, bisarylaminopyrene derivatives, aryl group-substituted pyrene derivatives, bisarylaminochrysene derivatives, aryl-substituted Chrysene derivative, bisarylaminofluoranthene derivative, aryl-substituted fluoranthene derivative, indenoperylene derivative, acenaphthofluoranthene derivative, pyromethene boron complex compound, compound having a pyromethene skeleton or metal complex thereof, diketopyrrolopyrrole derivative, perylene Derivatives and naphthacene derivatives.

  Moreover, as the first material according to the present embodiment, a compound represented by the following general formula (10) may be used.

In the general formula (10), _{A D} is a substituted or an aromatic hydrocarbon group unsubstituted ring carbon 12-50, an aromatic hydrocarbon group ring carbon 12-50 in the _{A D} As, for example, derived from naphthalene, anthracene, benzoanthracene, phenanthrene, chrysene, pyrene, fluoranthene, benzofluoranthene, perylene, picene, triphenylene, fluorene, benzofluorene, stilbene, naphthacene, acenaphthofluoranthene, etc. Further, a group obtained by benzoating these aromatic hydrocarbon groups and a group obtained by expanding a ring can also be mentioned.
In the general formula (10), _BD is a group represented by the following general formula (11).
In the general formula (10), pa is an integer of 1 to 4, and pb is an integer of 0 to 4.

In the general formula (11), Ar ₁ , Ar ₂ and Ar ₃ are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, a substituted or unsubstituted carbon number of 1 to A substituent selected from the group consisting of 50 alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, and substituted or unsubstituted heterocyclic groups having 5 to 50 ring atoms; pc is an integer of 0 or more and 4 or less, and in the general formula (11), the wavy line part represents the bonding site with the aromatic hydrocarbon group represented by _AD .
In the general formula (10) and (11), when A _D there is a plurality may be the same or different from each other, if the B _D there is a plurality may be the same or different from each other, When there are a plurality of pas, they may be the same as or different from each other. When there are a plurality of pbs, they may be the same as or different from each other. When there are a plurality of Ar _{1 s} , they may be the same as or different from each other. If there are a plurality of Ar _{2 s} , they may be the same as or different from each other. If there are a plurality of Ar _{3 s} , they may be the same as or different from each other. May be the same as or different from each other.

Examples of the compound represented by the general formula (10) include compounds having the following general formulas, but the first material is not limited to these examples. In the following description, A _{D1 to} A _D4 are each independently synonymous with A _D , and B _{D1 to} B _D4 are each independently synonymous with _BD .

The aromatic hydrocarbon group in _AD is preferably an aromatic hydrocarbon group having 12 to 30 ring carbon atoms, more preferably an aromatic hydrocarbon group having 12 to 24 ring carbon atoms, Aromatic hydrocarbon groups having 18 to 20 carbon atoms are more preferred. Examples of the aromatic hydrocarbon group in _AD include naphthylphenyl group, naphthyl group, acenaphthylenyl group, anthryl group, benzoanthryl group, aceanthryl group, phenanthryl group, benzo [c] phenanthryl group, phenalenyl group, and fluorenyl. Group, picenyl group, pentaphenyl group, pyrenyl group, chrysenyl group, benzo [g] chrysenyl group, s-indacenyl group, as-indacenyl group, fluoranthenyl group, benzo [k] fluoranthenyl group, triphenylenyl group, benzo [B] Triphenylenyl group, benzofluorenyl group, styrylphenyl group, naphthacenyl group, perylenyl group, and those obtained by further ring expansion such as anthryl group, picenyl group, pyrenyl group, chrysenyl group, fluoranthenyl The group benzo [k] Preferred are a olanthenyl group, a benzofluorenyl group, a styrylphenyl group, a naphthacenyl group, a perylenyl group, and a benzoated group or a ring-expanded group thereof. Anthryl group, pyrenyl group, chrysenyl group, benzo [k] fluoranthenyl Group, benzofluorenyl group, styrylphenyl group, acenaphtho [1,2-k] fluoranthenyl group, and those obtained by further benzoation or ring expansion are more preferable, anthryl group, pyrenyl group, chrysenyl group, A benzo [k] fluoranthenyl group, a benzofluorenyl group, an acenaphtho [1,2-k] fluoranthenyl group, and a naphthacenyl group are particularly preferable.

As the aromatic hydrocarbon group in Ar ₁ , Ar ₂ and Ar _3, an aromatic hydrocarbon group having 6 to 24 ring carbon atoms is preferable and the ring forming carbon number is 6 to 12 independently. Aromatic hydrocarbon groups are more preferred. Examples of the aromatic hydrocarbon group in Ar ₁ , Ar ₂ and Ar ₃ are each independently a phenyl group, a naphthylphenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, an acenaphthylenyl group, an anthryl group, or a benzoanthryl group. , Aceanthryl group, phenanthryl group, benzo [c] phenanthryl group, phenalenyl group, fluorenyl group, picenyl group, pentaphenyl group, pyrenyl group, chrysenyl group, benzo [g] chrysenyl group, s-indacenyl group, as-indacenyl group Fluoranthenyl group, benzo [k] fluoranthenyl group, triphenylenyl group, benzo [b] triphenylenyl group, benzofluorenyl group, styrylphenyl group, naphthacenyl group, perylenyl group, and a group obtained by further benzoating them Ring expansion A phenyl group, a biphenylyl group, a terphenylyl group, and a naphthyl group are preferable, a phenyl group, a biphenylyl group, and a terphenylyl group are more preferable, and a phenyl group is particularly preferable.
Examples of the aromatic hydrocarbon group having a substituent include phenyl naphthyl group, naphthylphenyl group, tolyl group, xylyl group, silylphenyl group, trimethylsilylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorine. Examples include oleenyl group, 9,9′-spirobifluorenyl group, cyanophenyl group, tolyl group, xylyl group, trimethylsilylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluoride. Olenyl group, 9,9′-spirobifluorenyl group, cyanophenyl group, silylphenyl group and the like are preferable.

As the alkyl group in Ar ₁ , Ar ₂ and Ar _3, an alkyl group having 1 to 10 carbon atoms is preferable, and an alkyl group having 1 to 5 carbon atoms is more preferable. Examples of the alkyl group in Ar ₁ and Ar ₂ include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group (isomers ), Hexyl group (including isomer), heptyl group (including isomer), octyl group (including isomer), nonyl group (including isomer), decyl group (including isomer), undecyl group (Including isomers), dodecyl group (including isomers), and the like, and include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t- A butyl group and a pentyl group (including isomers) are preferable, and a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, and t-butyl group are more preferable. Properly, a methyl group, an ethyl group, an isopropyl group and t- butyl group is particularly preferable.
The alkyl group in Ar ₁ , Ar ₂ and Ar ₃ may each independently be a cycloalkyl group having 3 to 50 ring carbon atoms. The cycloalkyl groups in Ar ₁ , Ar ₂ and Ar ₃ are each independently preferably a cycloalkyl group having 3 to 6 ring carbon atoms, and more preferably a cycloalkyl group having 5 or 6 ring carbon atoms. . Examples of the cycloalkyl group in Ar ₁ , Ar ₂ and Ar ₃ include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like, and a cyclopentyl group and a cyclohexyl group include preferable.
The alkenyl groups in Ar ₁ , Ar ₂ and Ar ₃ are each independently preferably an alkenyl group having 2 to 20 carbon atoms, and more preferably an alkenyl group having 2 to 10 carbon atoms. Examples of the alkenyl group in Ar ₁ , Ar ₂ and Ar ₃ include vinyl group, allyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1,3-butanedienyl group, 1-methylvinyl group, 1 -Methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, 1,2-dimethylallyl group and the like.
Examples of substituted alkenyl groups include styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl. Group, 1-phenyl-1-butenyl group, 3-phenyl-1-butenyl group and the like.
As the alkynyl group in Ar ₁ , Ar ₂ and Ar _3, an alkynyl group having 2 to 20 carbon atoms is preferable, and an alkynyl group having 2 to 10 carbon atoms is more preferable. Examples of the alkynyl group in Ar ₁ , Ar ₂ and Ar ₃ include a propargyl group and a 3-pentynyl group.

As the heterocyclic group in Ar ₁ , Ar ₂ and Ar ₃ , a heterocyclic group having 5 to 24 ring atoms is preferable, and a heterocyclic group having 5 to 18 ring atoms is independently selected. More preferred. Examples of the heterocyclic group in Ar ₁ , Ar ₂ and Ar ₃ include heterocyclic groups containing 1 to 5 heteroatoms (for example, nitrogen atom, oxygen atom, sulfur atom). Furthermore, the heterocyclic groups in Ar ₁ , Ar ₂ and Ar ₃ are each independently, for example, pyrrolyl group, furyl group, thienyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, imidazolyl group , Oxazolyl, thiazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, indolyl, isoindolyl, benzofuranyl, isobenzofuranyl, benzothiophenyl, isobenzo Thiophenyl, indolizinyl, quinolidinyl, quinolyl, isoquinolyl, cinnolyl, phthalazinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, benzoxazolyl, benzthia Zolyl group, indazolyl group, benzisoxazolyl group, benzisothiazolyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, Examples include phenothiazinyl, phenoxazinyl, and xanthenyl groups. Furyl, thienyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzo A thiophenyl group is preferable, and a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group are more preferable.

In the compound represented by the general formula (10), an arbitrary substituent when “substituted or unsubstituted” is
An alkyl group having 1 to 50 carbon atoms (preferably 1 to 10, more preferably 1 to 5);
An alkenyl group having 2 to 20 carbon atoms (preferably 2 to 10 carbon atoms);
An alkynyl group having 2 to 20 carbon atoms (preferably 2 to 10 carbon atoms);
A cycloalkyl group having 3 to 50 ring carbon atoms (preferably 3 to 6, more preferably 5 or 6);
An aromatic hydrocarbon group having 6 to 50 ring carbon atoms (preferably 6 to 24, more preferably 6 to 12);
Aralkyl having 1 to 50 carbon atoms (preferably 1 to 10, more preferably 1 to 5) having an aromatic hydrocarbon group having 6 to 50 ring carbon atoms (preferably 6 to 24, more preferably 6 to 12). Group;
An amino group;
A monoalkylamino group or dialkylamino group having an alkyl group having 1 to 50 carbon atoms (preferably 1 to 10, more preferably 1 to 5 carbon atoms);
Monoarylamino or diarylamino group having an aromatic hydrocarbon group having 6 to 50 ring carbon atoms (preferably 6 to 24, more preferably 6 to 12);
An alkoxy group having an alkyl group having 1 to 50 carbon atoms (preferably 1 to 10, more preferably 1 to 5 carbon atoms);
An aryloxy group having an aromatic hydrocarbon group having 6 to 50 ring carbon atoms (preferably 6 to 24, more preferably 6 to 12);
An alkylthio group having an alkyl group having 1 to 50 carbon atoms (preferably 1 to 10, more preferably 1 to 5 carbon atoms);
An arylthio group having an aromatic hydrocarbon group having 6 to 50 ring carbon atoms (preferably 6 to 24, more preferably 6 to 12);
An alkyl group having 1 to 50 carbon atoms (preferably 1 to 10, more preferably 1 to 5) and an aromatic hydrocarbon group having 6 to 50 ring carbon atoms (preferably 6 to 24, more preferably 6 to 12). A mono-substituted silyl group, a di-substituted silyl group or a tri-substituted silyl group having a group selected from:
It has 5 to 50 ring atoms (preferably 5 to 24, more preferably 5 to 18), and 1 to 5 (preferably 1 to 3, more preferably) heteroatoms (for example, nitrogen atom, oxygen atom, sulfur atom). 1 to 2) containing heterocyclic group;
A haloalkyl group having 1 to 50 carbon atoms (preferably 1 to 10, more preferably 1 to 5);
Halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom, preferably fluorine atom);
A cyano group;
Those selected from the group consisting of nitro groups are preferred.
Among the above substituents, in particular, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, an aromatic hydrocarbon group having 6 to 12 ring carbon atoms, and 5 to 24 ring atoms. Preferred is a substituent selected from the group consisting of heterocyclic groups containing 1 to 3 heteroatoms (nitrogen atom, oxygen atom, sulfur atom).

Alkyl group having 1 to 50 carbon atoms as a substituent of the term "substituted or unsubstituted" are synonymous with those described as the alkyl group in the _Ar 1, Ar ₂ and Ar _3. The alkenyl group having 2 to 20 carbon atoms as a substituent in the case of “substituted or unsubstituted” has the same meaning as described for the alkenyl group in Ar ₁ , Ar ₂ and Ar ₃ .
The alkynyl group having 2 to 20 carbon atoms as a substituent in the case of “substituted or unsubstituted” has the same meaning as described for the alkynyl group in Ar ₁ , Ar ₂ and Ar ₃ .
The cycloalkyl group having 3 to 50 ring carbon atoms as a substituent in the case of “substituted or unsubstituted” has the same meaning as described as the cycloalkyl group in Ar ₁ , Ar ₂ and Ar ₃ .
The aromatic hydrocarbon group having 6 to 50 ring carbon atoms as a substituent in the case of “substituted or unsubstituted” has the same meaning as described for the aromatic hydrocarbon group in Ar ₁ , Ar ₂ and Ar ₃ . is there.
The aralkyl group having 6 to 50 ring carbon atoms as a substituent when “substituted or unsubstituted” has an aromatic hydrocarbon group having 6 to 50 ring carbon atoms and an alkyl group having 1 to 50 carbon atoms. A specific example of this alkyl group moiety is the same as the above-described alkyl group, and a specific example of the aromatic hydrocarbon group moiety is synonymous with the above-described aromatic hydrocarbon group.
In the monoalkylamino group or dialkylamino group as a substituent when “substituted or unsubstituted”, specific examples of the alkyl group moiety are the same as the above-described alkyl group.
In the monoarylamino group or diarylamino group as a substituent when “substituted or unsubstituted”, specific examples of the aryl group (aromatic hydrocarbon group) moiety are the same as the above-mentioned aromatic hydrocarbon group.

In the alkoxy group as a substituent when “substituted or unsubstituted”, specific examples of the alkyl group moiety are the same as those of the alkyl group described above, and the alkoxy group is preferably, for example, a methoxy group or an ethoxy group.
In the aryloxy group as a substituent when “substituted or unsubstituted”, specific examples of the aryl group (aromatic hydrocarbon group) portion are the same as the above-mentioned aromatic hydrocarbon group, and the aryloxy group is For example, a phenoxy group etc. are mentioned.
In the alkylthio group as a substituent in the case of “substituted or unsubstituted”, specific examples of the alkyl group moiety are the same as the above-described alkyl group.
Specific examples of the aryl group (aromatic hydrocarbon group) moiety in the arylthio group as a substituent when “substituted or unsubstituted” are the same as the above-described aromatic hydrocarbon group.
A mono-substituted silyl group, a di-substituted silyl group or a tri-substituted silyl group as a substituent in the case of “substituted or unsubstituted” includes an alkylsilyl group having 1 to 50 carbon atoms and an arylsilyl having 6 to 50 ring carbon atoms. The group can be mentioned. Examples of the alkylsilyl group having 1 to 50 carbon atoms include a monoalkylsilyl group, a dialkylsilyl group, and a trialkylsilyl group. For example, specific examples of each alkyl group are the same as those described above. Examples of the arylsilyl group having 6 to 50 ring carbon atoms include a monoarylsilyl group, a diarylsilyl group, and a triarylsilyl group, and specific examples of each aryl group are the same as the aryl group described below. , Trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, isopropyldimethylsilyl group, triphenylsilyl group, phenyldimethylsilyl group, t-butyldiphenylsilyl group, tolylsilylsilyl Groups and the like.

The heterocyclic group as a substituent in the case of “substituted or unsubstituted” has the same meaning as described for the heterocyclic group in Ar ₁ , Ar ₂ and Ar ₃ .
Examples of the haloalkyl group as a substituent in the case of “substituted or unsubstituted” include those obtained by halogenating the above-described alkyl group, and specific examples include a trifluoromethyl group.

  Moreover, as the first material according to the present embodiment, a compound represented by the following general formula (12) may be used.

In the general formula (12), R _{110 to} R ₁₂₁ are each independently a hydrogen atom or a substituent, and the substituents in R _{110 to} R ₁₂₁ are
Halogen atoms,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms,
A substituted or unsubstituted trialkylsilyl group,
A substituted or unsubstituted arylalkylsilyl group,
A substituted or unsubstituted triarylsilyl group,
Substituted or unsubstituted diarylphosphine oxide groups,
An amino group,
A monoalkylamino group or a dialkylamino group having a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
It is a substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

Second material The second material according to this embodiment is a delayed fluorescent material.

-Delayed fluorescence emission Delayed fluorescence (thermally activated delayed fluorescence) is explained on pages 261 to 268 of "Device properties of organic semiconductors" (edited by Chiya Adachi, published by Kodansha). In that document, if the energy difference ΔE ₁₃ between the excited singlet state and the excited triplet state of the fluorescent material can be reduced, the reverse energy from the excited triplet state to the excited singlet state, which usually has a low transition probability. It has been described that migration occurs with high efficiency and that thermally activated delayed fluorescence (TADF) is expressed. In addition, FIG. 10.38 in this document explains the mechanism of delayed fluorescence generation. The second material in the present embodiment is a compound that exhibits thermally activated delayed fluorescence generated by such a mechanism.
The delayed fluorescence emission can be confirmed by transient PL measurement.

FIG. 2 shows a schematic diagram of an exemplary apparatus for measuring transient PL.
The transient PL measurement apparatus 100 of the present embodiment includes a pulse laser unit 101 that can irradiate light of a predetermined wavelength, a sample chamber 102 that houses a measurement sample, a spectrometer 103 that separates light emitted from the measurement sample, A streak camera 104 for forming a two-dimensional image and a personal computer 105 for capturing and analyzing the two-dimensional image are provided. Note that the measurement of the transient PL is not limited to the apparatus described in this embodiment.
The sample accommodated in the sample chamber 102 is obtained by forming a thin film in which a doping material is doped at a concentration of 12 mass% with respect to a matrix material on a quartz substrate.
The thin film sample accommodated in the sample chamber 102 is excited by being irradiated with a pulse laser from the pulse laser unit 101. The emitted light is extracted from the direction of 90 degrees of the excitation light, dispersed by the spectroscope 103, and a two-dimensional image is formed in 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 emission intensity. When this two-dimensional image is cut out along a predetermined time axis, an emission spectrum in which the vertical axis represents the emission intensity and the horizontal axis represents the wavelength can be obtained. Further, when the two-dimensional image is cut out along the wavelength axis, an attenuation curve (transient PL) in which the vertical axis represents the logarithm of the emission intensity and the horizontal axis represents time can be obtained.

  For example, the thin film sample A was prepared as described above using the following reference compound H1 as a matrix material and the following reference compound D1 as a doping material, and transient PL measurement was performed.

The behavior of delayed fluorescence can also be analyzed based on the decay curve obtained from the transient PL measurement. Transient PL is a technique for measuring the decay behavior (transient characteristics) of PL emission after irradiating a sample with a pulsed laser and exciting it and stopping the irradiation. PL emission in the TADF material is classified into a light emission component from a singlet exciton generated by the first PL excitation and a light emission component from a singlet exciton generated via a triplet exciton. The lifetime of singlet excitons generated by the first PL excitation is on the order of nanoseconds and is very short. Therefore, light emitted from the singlet excitons is rapidly attenuated after irradiation with the pulse laser.
On the other hand, delayed fluorescence is gradually attenuated due to light emission from singlet excitons generated via a long-lived triplet exciton. Thus, there is a large time difference between the light emission from the singlet exciton generated by 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 obtained.

Here, the attenuation curve was analyzed using the thin film sample A and the thin film sample B described above. Thin film sample B was prepared as described above using reference compound H2 as a matrix material and reference compound D1 as a doping material.
FIG. 3 shows attenuation curves obtained from the transient PL measured for the thin film sample A and the thin film sample B.

As described above, by the transient PL measurement, it is possible to obtain a light emission decay curve with the vertical axis representing the emission intensity and the horizontal axis representing the time. Based on this emission decay curve, the fluorescence intensity of fluorescence emitted from the singlet excited state generated by photoexcitation and delayed fluorescence emitted from the singlet excited state generated by reverse energy transfer via the triplet excited state The ratio can be estimated. In the delayed fluorescence emitting material, the ratio of the delayed fluorescence intensity that attenuates slowly is somewhat larger than the fluorescence intensity that decays quickly.
The delayed fluorescence emission amount in this embodiment can be obtained using the apparatus shown in FIG. The second material includes Prompt light emission (immediate light emission) that is immediately observed from the excited state after being excited with pulsed light (light irradiated from a pulse laser) having a wavelength that is absorbed by the second material. After the excitation, there is delay light emission (delayed light emission) that is not observed immediately but is observed thereafter. In the present embodiment, the amount of delay light emission (delayed light emission) is preferably 5% or more with respect to the amount of Promp light emission (immediate light emission).
The amounts of Prompt light emission and Delay light emission can be obtained by the same method as described in “Nature 492, 234-238, 2012”. In addition, the apparatus used for calculation of the amount of Promp light emission and Delay light emission is not limited to the thing as described in the said literature.
The sample used for the measurement of delayed fluorescence is, for example, co-evaporation of a second material and a compound TH-2 described later on a quartz substrate so that the ratio of the second material is 12% by mass. And what formed the thin film with a film thickness of 100 nm can be used.

  In the present embodiment, the second material preferably has a partial structure represented by the following general formula (2) and a partial structure represented by the following general formula (2Y) in one molecule.

In the general formula (2), CN is a cyano group.
n is an integer of 1 or more. n is preferably an integer of 1 or more and 5 or less, and more preferably an integer of 2 or more and 4 or less.
Z _{1 to} Z ₆ are each independently a nitrogen atom, a carbon atom bonded to CN, or a carbon atom bonded to another atom in the molecule of the second material. For example, when Z ₁ is a carbon atom bonded to CN, at least one of the remaining five (Z _{2 to} Z ₆ ) is a carbon atom bonded to another atom in the molecule of the second material. Become. The other atom may be an atom constituting a partial structure represented by the following general formula (2Y), or may be an atom constituting a linking group or a substituent intervening with the partial structure.
The second material according to the present embodiment may have a 6-membered ring composed of Z _{1 to} Z ₆ as a partial structure, or a condensed structure obtained by further condensing a ring with the 6-membered ring. You may have a ring as a partial structure.

(In the general formula (2Y), F and G each independently represent a ring structure.
m is 0 or 1.
When m is 1, Y ₂₀ represents a single bond, an oxygen atom, a sulfur atom, a selenium atom, a carbon atom, a silicon atom, or a germanium atom. )

  When m is 0 in the general formula (2Y), the general formula (2Y) is represented by the following general formula (20Y).

  The ring structure F and the ring structure G in the general formula (20Y) have the same meaning as the ring structure F and the ring structure G in the general formula (2Y).

  In the general formula (2Y), when m is 1, the general formula (2Y) is represented by any one of the following general formulas (22) to (28).

  The ring structure F and the ring structure G in the general formulas (22) to (28) have the same meaning as the ring structure F and the ring structure G in the general formula (2Y).

  In the present embodiment, the ring structure F and the ring structure G are preferably a 5-membered ring or a 6-membered ring, and the 5-membered ring or 6-membered ring is preferably an unsaturated ring, More preferably, it is a member ring.

  The second material according to the present embodiment is preferably a compound represented by the following general formula (20).

In the general formula (20),
A is represented by the general formula (2). However, in the general formula (2), CN is a cyano group, n is an integer of 1 or more, and Z _{1 to} Z ₆ are independent of each other. Are a carbon atom bonded to CN, a carbon atom bonded to CN, a carbon atom bonded to R, a carbon atom bonded to L, or a carbon atom bonded to D, and a carbon atom bonded to CN among Z _{1 to} Z ₆ And at least one carbon atom bonded to L or D,
Each R is independently a hydrogen atom or a substituent. The substituent in R is a halogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted ring formation. Aromatic heterocyclic group having 5 to 30 atoms, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, substituted or unsubstituted ring forming carbon number 6-60 arylsilyl groups, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 ring carbon atoms, substituted or unsubstituted 2 to 30 carbon atoms Alkylamino group, substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, and substituted or unsubstituted It is a substituent selected from the group consisting of ring-forming arylthio group having 6 to 30 carbon atoms.

In the general formula (20), D is represented by the general formula (2Y), provided that the ring structure F and the ring structure G in the general formula (2Y) may be unsubstituted or have a substituent. Well, m is 0 or 1, and when m is 1, Y ₂₀ is a single bond, oxygen atom, sulfur atom, selenium atom, carbonyl group, CR ₂₁ R ₂₂ , SiR ₂₃ R ₂₄ or GeR _25. represents _{R 26,} R 21 ~R ₂₆ is synonymous with the groups mentioned in the R. In the general formula (2Y), when m is 1, the general formula (2Y) is represented by any one of the general formulas (22) to (25) and the following general formulas (21Y) to (24Y). Is done.

In the general formula (20),
(I) When L is interposed between A and D,
L is a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 14 ring atoms, CR ₈₁ R ₈₂ , NR _{83, O, S, SiR 84} R 85, CR 86 R 87 -CR 88 R 89, CR 90 = CR 91, a substituted or unsubstituted aliphatic hydrocarbon ring group or a substituted or unsubstituted aliphatic heterocyclic group, And
R _{81 to} R ₉₁ each independently have the same meaning as R.
In the general formula (20),
(Ii) when L is located at the end in the molecule of the second material;
L is synonymous with the group mentioned by said R.

In the general formula (20),
f is an integer of 1 or more,
e and g are each independently an integer of 0 or more.
When A is plural, they may be the same or different.
When D is plural, they may be the same or different.
When L is plural, they may be the same or different.

  The general formula (20) is represented by the following general formulas (201) to (220), for example.

  In the general formula (20), in the repeating unit enclosed in parentheses having the repeating number f, D may be bonded to A via L, or via L to D. A may be bonded. For example, you may branch like the following general formula (221)-(228).

The second material according to this embodiment is not limited to the compounds represented by the general formulas (201) to (228).
For the purpose of keeping ΔST of one molecule small, it is preferable that L is not a condensed aromatic ring in terms of molecular design, but a condensed aromatic ring is also employed as long as thermally active delayed fluorescence can be obtained. Can do. Moreover, since the molecular design which arrange | positions A and D correctly in one molecule is needed, it is preferable that the 2nd material which concerns on this embodiment is a low molecular material. Accordingly, the molecular weight is preferably 5000 or less, and the molecular weight is more preferably 3000 or less. The second material according to the present embodiment includes the partial structures of the general formula (2) and the general formula (2Y). As a result, the organic EL element including the second material emits thermally activated delayed fluorescence. Can do.

  In the present embodiment, the general formula (2Y) is preferably represented by at least one of the following general formula (2a) and the following general formula (2x).

In the general formula (2x), A and B each independently represent a ring structure represented by the following general formula (2c) or a ring structure represented by the following general formula (2d), The ring structure B is condensed with an adjacent ring structure at an arbitrary position.
px and py are each independently an integer of 0 or more and 4 or less, and represent the numbers of the ring structure A and the ring structure B, respectively. When px is an integer of 2 or more and 4 or less, the plurality of ring structures A may be the same as or different from each other. When py is an integer of 2 or more and 4 or less, the plurality of ring structures B may be the same as or different from each other. Therefore, for example, when px is 2, the ring structure A may have two ring structures represented by the following general formula (2c) or two ring structures represented by the following general formula (2d). Alternatively, a combination of one ring structure represented by the following general formula (2c) and one ring structure represented by the following general formula (2d) may be used.

In the general formula (2d), Z ₇ represents a carbon atom, a nitrogen atom, a sulfur atom, or an oxygen atom.

  In the general formula (2x), when px is 0 and c is py, it is represented by the following general formula (2b).

In the general formula (2b), c is an integer of 1 or more and 4 or less. When c is an integer of 2 or more and 4 or less, the plurality of ring structures E may be the same as or different from each other.
In the general formula (2b), E represents a ring structure represented by the general formula (2c) or a ring structure represented by the general formula (2d), and the ring structure E represents an adjacent ring structure and Condensation at any position.
Therefore, for example, when c is 2, the two ring structures E may have two ring structures represented by the general formula (2c) or two ring structures represented by the general formula (2d). One ring structure represented by the general formula (2c) may be combined with one ring structure represented by the general formula (2d).

  By simultaneously holding the partial structures of the general formula (2) and the general formula (2Y) in one molecule, ΔST can be designed to be effectively small.

  The second material according to the present embodiment preferably has a structure represented by the following general formula (2e) in the molecule.

In the general formula (2e), R _{1 to} R ₉ are each independently
Hydrogen atom,
A substituent, or a single bond that binds to another atom in the molecule of the second material,
The substituent in R _{1 to} R ₉ is a halogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 ring atoms, substituted Or an unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted group. An alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted ring carbon number A 6 to 60 arylamino group, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, and a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms. It is a substituent selected from the group.
However, at least one of R _{1 to} R ₉ is the single bond.
In the general formula (2e), at least one of the combinations of substituents selected from R _{1 to} R ₉ may be bonded to each other to form a ring structure. In the case of constructing this ring structure, that is, in the general formula (2e), among the 6-membered ring carbon atoms or 5-membered ring nitrogen atoms to which R _{1 to} R ₉ are respectively bonded, Substituents selected from R _{1 to} R ₈ and R ₉ bonded to a 5-membered ring nitrogen atom can form a ring structure. Specifically, in the general formula (2e), R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₄ and R ₅ , R ₅ and R ₆ , R ₆ and R ₇ , R Among the combinations of substituents consisting of ₇ and R ₈ , R ₈ and R ₉ , R ₁ and R ₉ , at least one set may be bonded to each other to construct a ring structure.
In the present embodiment, the ring structure constructed by bonding substituents to each other is preferably a condensed ring. For example, as a case where the ring structure is constructed in the general formula (2e), a case where a condensed 6-membered ring structure is constructed can be considered.

  Moreover, it is preferable that the 2nd material which concerns on this embodiment has the structure represented by the following general formula (2y) in the molecule | numerator.

R _{11 to} R ₁₉ in the general formula (2y) are independently the same as R _{1 to} R ₉ in the general formula (2e).
However, at least one of R _{11 to} R ₁₉ is a single bond that is bonded to another atom in the molecule of the second material.
In the general formula (2y), at least one of the combinations of substituents selected from R _{11 to} R ₁₉ may be bonded to each other to form a ring structure.
In the general formula (2y), A and B each independently represent a ring structure represented by the following general formula (2g) or a ring structure represented by the following general formula (2h), The ring structure B is condensed with an adjacent ring structure at an arbitrary position.
px is the number of the ring structure A, and is an integer of 0 or more and 4 or less. When px is an integer of 2 or more and 4 or less, the plurality of ring structures A may be the same as or different from each other. When py is an integer of 2 or more and 4 or less, the plurality of ring structures B may be the same as or different from each other. py is the number of ring structures B and is an integer of 0 or more and 4 or less. Therefore, for example, when px is 2, the two ring structures A may have two ring structures represented by the following general formula (2g), or two ring structures represented by the following general formula (2h). Or a combination of one ring structure represented by the following general formula (2g) and one ring structure represented by the following general formula (2h).

In the general formula (2g), R ₂₀₁ and R ₂₀₂ are each independently synonymous with R _{1 to} R ₉ , and R ₂₀₁ and R ₂₀₂ may be bonded to each other to form a ring structure. . R ₂₀₁ and R ₂₀₂ are each bonded to a carbon atom constituting the 6-membered ring of the general formula (2g).
In the general formula (2h), Z ₈ represents CR ₂₀₃ R ₂₀₄ , NR ₂₀₅ , a sulfur atom, or an oxygen atom, and R _{202 to} R ₂₀₅ are each independently a substituent in R _{1 to} R ₉ . It is synonymous.
In the general formula (2y), at least one of the combinations of substituents selected from R _{11 to} R ₁₉ and R _{201 to} R ₂₀₅ may be bonded to each other to form a ring structure.

  In the general formula (2y), when px is 0 and py is c, it is represented by the following general formula (2f).

R _{11 to} R ₁₉ in the general formula (2f) are independently the same as R _{1 to} R ₉ in the general formula (2e).
However, at least one of R _{11 to} R ₁₉ is a single bond that is bonded to another atom in the molecule of the second material.
In the general formula (2f), at least one of the combinations of substituents selected from R _{11 to} R ₁₉ may be bonded to each other to form a ring structure.
In the general formula (2f), E represents a ring structure represented by the general formula (2g) or a ring structure represented by the general formula (2h), and the ring structure E represents an adjacent ring structure. And condensed at any position.
c is the number of the ring structure E, and is an integer of 1 or more and 4 or less. When c is an integer of 2 or more and 4 or less, the plurality of ring structures E may be the same as or different from each other. Therefore, for example, when c is 2, the two ring structures E may have two ring structures represented by the general formula (2g) or two ring structures represented by the general formula (2h). Or a combination of one ring structure represented by the following general formula (2g) and one ring structure represented by the general formula (2h).

  The second material according to the present embodiment is preferably represented by the following general formula (2A).

In the general formula (2A), n is an integer of 1 or more, t is an integer of 1 or more, and u is an integer of 0 or more.
L _A is a substituted or unsubstituted ring formed C6-30 aromatic hydrocarbon ring or aromatic heterocyclic ring atoms 6 to 30.
CN is a cyano group.
D ₁ and D ₂ are each independently represented by the general formula (2Y), provided that the ring structure F and the ring structure G in the general formula (2Y) may be unsubstituted or have a substituent. Well, m is 0 or 1, and when m is 1, Y ₂₀ is a single bond, oxygen atom, sulfur atom, selenium atom, carbonyl group, CR ₂₁ R ₂₂ , SiR ₂₃ R ₂₄ or GeR _25. R ₂₆ represents R ₂₆ , and R _{21 to} R ₂₆ have the same meaning as R. When m is 1, the general formula (2Y) is represented by any one of the general formulas (22) to (25) and the general formulas (21Y) to (24Y).
D ₁ and D ₂ may be the same or different. When t is 2 or more, the plurality of D ₁ may be the same as or different from each other. When u is 2 or more, the plurality of D ₂ may be the same as or different from each other.

In this embodiment, L _A is preferably a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 14 ring carbon atoms. Examples of the aromatic hydrocarbon ring having 6 to 14 ring carbon atoms include benzene, naphthalene, fluorene, and phenanthrene. More preferably, it is an aromatic hydrocarbon ring having 6 to 10 ring carbon atoms.
The aromatic heterocyclic ring atoms 6 to 30 in the L _A, pyridine, pyrimidine, pyrazine, quinoline, quinazoline, phenanthroline, benzofuran, etc. dibenzofuran and the like.

In the present embodiment, in the general formula (2A), L the D ₁ or the D ₂ is coupled to the first carbon atom of which are building an aromatic hydrocarbon ring represented by _A, the first The CN may be bonded to the second carbon atom adjacent to the carbon atom. For example, in the compound according to this embodiment, as in the partial structure represented by the following general formula (2B), D is bonded to the first carbon atom C _1, and the compound adjacent to the _first carbon atom C ₁ is adjacent to the _first carbon atom C ₁ . second cyano group to the carbon atom C ₂ may be bonded. D in the following general formula (2B) has the same meaning as D ₁ or D ₂ . In the following general formula (2B), a wavy line portion represents a bonding position with another structure or atom.

And D ₁ or D ₂ having the structure as shown in formula (2a) or Formula (2b), bonded to the aromatic hydrocarbon ring is a cyano group represented by adjacent said L _A As a result, the value of ΔST of the compound can be reduced.

In the present embodiment, the t is preferably an integer of 2 or more. If the said D ₁ of the 2 or more aromatic hydrocarbon ring represented by L _A is attached, a plurality of D ₁ may be a different structure may be the same structure.

  The second material according to the present embodiment is preferably represented by the following general formula (21).

In the general formula (21), A ₂₁ and B ₂₁ are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring forming atom number of 5 to 5. 30 aromatic heterocyclic groups are represented.
X _{21 to} X ₂₈ and Y _{21 to} Y ₂₈ each independently represent a nitrogen atom, a carbon atom bonded to ^RD , or a carbon atom bonded to L ₂₃ . However, at least one of X _{25 to} X ₂₈ is a carbon atom bonded to L _23, and at least one of Y _{21 to} Y ₂₄ is a carbon atom bonded to L ₂₃ .
R ^D is each independently a hydrogen atom or a substituent, and the substituent in R ^D is
Halogen atoms,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted aromatic heterocyclic group having 5 to 30 ring atoms;
It is a substituent selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted silyl group.
L ₂₁ and L ₂₂ are each independently a single bond or a linking group;
As the linking group for L ₂₁ and L ₂₂ ,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
A multiple linking group in which 2 to 4 groups selected from the aromatic hydrocarbon groups are bonded;
A multiple linking group in which 2 to 4 groups selected from the heterocyclic group are bonded, or a group in which 2 to 4 groups selected from the aromatic hydrocarbon group and the heterocyclic group are bonded It is a multiple linking group.
L ₂₃ represents a substituted or unsubstituted monocyclic hydrocarbon group having 6 or less ring-forming carbon atoms, or a substituted or unsubstituted monocyclic heterocyclic group having 6 or less ring-forming atoms.
w represents an integer of 0 to 3. When w is 0, at least one of X _{25 to} X ₂₈ and at least one of Y _{21 to} Y ₂₄ are directly bonded.
A monocyclic hydrocarbon group is not a condensed ring but a group derived from a single hydrocarbon ring (aliphatic cyclic hydrocarbon or aromatic hydrocarbon), and a monocyclic heterocyclic group is a single ring A group derived from a heterocyclic ring.

Further, in the general formula (21), at least one of the following conditions (i) and (ii) is satisfied.
(I) At least one of A ₂₁ and B ₂₁ is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with a cyano group, or an aromatic having 6 to 30 ring atoms substituted with a cyano group Group heterocyclic group.
_(Ii) at least one of X 21 _{to X 24} and _Y 25 _{to Y 28} is a carbon atom bonded with ^{R D,} the ^R at least one of ^D is, ring carbon 6 is substituted with a cyano group Or an aromatic heterocyclic group having 6 to 30 ring atoms substituted with an aromatic hydrocarbon group having ˜30 or a cyano group.
However, if R ^D there are a plurality, or different in each of the plurality of R ^D identical.

In the general formula (21), the aromatic hydrocarbon group having 6 to 30 ring carbon atoms or the aromatic heterocyclic group having 6 to 30 ring atoms represented by A ₂₁ and B ₂₁ has a substituent. In the case, the substituent is a cyano group, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, Haloalkoxy group having 1 to 20 carbon atoms, alkylsilyl group having 1 to 10 carbon atoms, aryl group having 6 to 30 ring carbon atoms, aryloxy group having 6 to 30 ring carbon atoms, and aralkyl having 6 to 30 carbon atoms One or more groups selected from the group consisting of a group and a heterocyclic group having 5 to 30 ring atoms are preferable. When it has a plurality of substituents, they may be the same or different.

In the general formula (21), it is preferable that the condition (i) is satisfied and the condition (ii) is not satisfied.
Alternatively, in the general formula (21), it is preferable that the condition (ii) is satisfied and the condition (i) is not satisfied.
Alternatively, it is also preferable to satisfy the condition (i) and the condition (ii).

In the general formula (21), at least one of A ₂₁ and B ₂₁ is
A phenyl group substituted with a cyano group,
A naphthyl group substituted with a cyano group,
A phenanthryl group substituted with a cyano group,
A dibenzofuranyl group substituted with a cyano group,
A dibenzothiophenyl group substituted with a cyano group,
A biphenyl group substituted with a cyano group,
A terphenyl group substituted with a cyano group,
A 9,9-diphenylfluorenyl group substituted with a cyano group,
A 9,9′-spirobi [9H-fluoren] -2-yl group substituted with a cyano group,
A 9,9-dimethylfluorenyl group substituted with a cyano group or a triphenylenyl group substituted with a cyano group is preferred.

In the general formula _(21), at least one of X 21 _{to X 24} and _Y 25 _{to Y 28} are CR _^D, at least one of ^{R D} in X 21 _{to X 24} and _Y 25 _{to Y 28} are,
A phenyl group substituted with a cyano group,
A naphthyl group substituted with a cyano group,
A phenanthryl group substituted with a cyano group,
A dibenzofuranyl group substituted with a cyano group,
A dibenzothiophenyl group substituted with a cyano group,
A biphenyl group substituted with a cyano group,
A terphenyl group substituted with a cyano group,
A 9,9-diphenylfluorenyl group substituted with a cyano group,
A 9,9′-spirobi [9H-fluoren] -2-yl group substituted with a cyano group,
A 9,9-dimethylfluorenyl group substituted with a cyano group or a triphenylenyl group substituted with a cyano group is preferred.

In the general formula (21), X ₂₆ and Y ₂₃ are preferably bonded via L ₂₃ or directly bonded.
Further, in the general formula _(21), and _{X 26} and _{Y 22} is _either attached via a _{L 23,} or is preferably bonded directly.
Further, in the general formula _(21), and _{X 27} and _{Y 23} is _either attached via a _{L 23,} or is preferably bonded directly.

In the general formula (21), w is preferably 0.
Alternatively, in the general formula (21), w is preferably 1.

In the general formula (21), L ₂₁ and L ₂₂ are preferably a single bond or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.

  Specific examples of the second material according to this embodiment are shown below. The second material in the present invention is not limited to these specific examples.

- The second manufacturing method the second material of the material, for example, a partial structure represented by the general formula (2), is at least one of carbon atom bonded with the halogen atom of Z ₁ to Z ₆ A compound in which a commercially available compound is represented by the general formula (2Y) in the presence of a catalyst such as tetrakis (triphenylphosphine) palladium and a base, and a hydrogen atom is bonded to a nitrogen atom bonded to the ring structure F and the ring structure G Can be made to react.

-3rd material The singlet energy of the 3rd material which concerns on this embodiment is larger than the singlet energy of said 2nd material.

  In the present embodiment, the third material may include at least one of a partial structure represented by the following general formula (31) and a partial structure represented by the following general formula (32) in one molecule. preferable.

(In the general formula _{(31), X} 31 ~X ₃₆ are independently a carbon atom bonded with other atoms on the nitrogen atom or the molecule of the third material, with the _{proviso, X} 31 to X _At least one of ₃₆ is a carbon atom bonded to another atom in the molecule of the third material;
In the general formula (32), Y _{31 to} Y ₃₈ are each independently a nitrogen atom or a carbon atom bonded to another atom in the molecule of the third material, provided that Y _{31 to} Y _38. At least one of them is a carbon atom bonded to another atom in the molecule of the third material, and Y ₃₉ is a nitrogen atom, an oxygen atom, or a sulfur atom. )

In this embodiment, the partial structure represented by the general formula (31) is the third material as at least one group selected from the group consisting of the following general formula (33) and the following general formula (34). It is preferable that it is contained in.
As represented by the following general formula (33) and the following general formula (34), it is possible to keep the energy gap Eg _77K (M3) at 77 [K] high because the bonding sites are located at the meta positions. Therefore, it is preferable as the third material.

(In the general formula (33) and the general formula (34), X ₃₁ , X ₃₂ , X ₃₄ , and X ₃₆ are each independently a nitrogen atom or CR ₃₁ ,
R ₃₁ is a hydrogen atom or a substituent, and the substituent in R ₃₁ is
Halogen atoms,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted trialkylsilyl group,
A substituted or unsubstituted arylalkylsilyl group,
A substituted or unsubstituted triarylsilyl group,
Substituted or unsubstituted diarylphosphine oxide groups,
A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, provided that The substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R ₃₁ is a non-condensed ring,
In the said General formula (33) and the said General formula (34), a wavy line part represents the coupling | bond part with the other atom or other structure in the molecule | numerator of the said 3rd material. )

In the present embodiment, R ₃₁ is a hydrogen atom or a substituent, and the substituent in R ₃₁ is a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted group. It is preferably a substituent selected from the group consisting of a substituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. ₃₁ is more preferably a hydrogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. preferable.

In the present embodiment, in the general formula (33), it is preferable that X ₃₁ , X ₃₂ , X ₃₄ , and X ₃₆ are each independently CR ₃₁ .
In the present embodiment, in the general formula (34), it is preferable that X ₃₂ , X ₃₄ , and X ₃₆ are each independently CR ₃₁ .

In this embodiment, the partial structure represented by the general formula (32) includes the following general formula (35), the following general formula (36), the following general formula (37), the following general formula (38), and the following general formula. (39) and at least one group selected from the group consisting of the following general formula (30a) is preferably included in the third material.
Bonding sites as represented by the following general formula (35), the following general formula (36), the following general formula (37), the following general formula (38), the following general formula (39), and the following general formula (30a) Is preferable as the third material because the energy gap Eg _77K at 77 [K] can be kept high.

(In the general formulas (35) to (39) and (30a),
Y _{31 to} Y ₃₈ are each independently a nitrogen atom or CR ₃₂ ,
R ₃₂ is a hydrogen atom or a substituent, and the substituent in R ₃₂ is
Halogen atoms,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted trialkylsilyl group,
A substituted or unsubstituted arylalkylsilyl group,
A substituted or unsubstituted triarylsilyl group,
Substituted or unsubstituted diarylphosphine oxide groups,
A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, provided that The substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R ₃₂ is a non-condensed ring,
In the general formulas (35) to (36), Y ₃₉ is a nitrogen atom,
In the general formulas (37) to (39) and (30a), Y ₃₉ is NR ₃₃ , an oxygen atom, or a sulfur atom,
R ₃₃ is a substituent, the substituent in the _{R 33} is
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms,
A substituted or unsubstituted arylsilyl group having 6 to 50 ring carbon atoms,
A substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, provided that R ₃₃ The substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in is a non-condensed ring,
In the general formulas (35) to (39) and (30a), the wavy line part represents a bonding site with another atom or another structure in the molecule of the third material. )

In the present embodiment, R ₃₂ is a hydrogen atom or a substituent, and the substituent in R ₃₂ is a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted group. It is preferably a substituent selected from the group consisting of a substituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. ₃₂ is more preferably a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In the present embodiment, in the general formula (35), Y _{31 to} Y ₃₈ are preferably each independently CR ₃₂ .
Further, in the general formula (36) and the general formula _{(37), Y 31 ~Y 35} , Y 37, Y 38 each independently is preferably _{CR 32.}
In the general formula (38), Y ₃₁ , Y ₃₂ , Y ₃₄ , Y ₃₅ , Y ₃₇ , Y ₃₈ are preferably each independently CR ₃₂ .
Further, in the general formula _{(39), Y} 32 ~Y ₃₈ each independently is preferably _{CR 32.}
In the general formula (30a), Y _{32 to} Y ₃₇ are preferably each independently CR ₃₂ .
In these cases, the plurality of R ₃₂ may be the same or different.

In the present embodiment, the third material preferably includes a group represented by the following general formula (30b).
It is preferable for the third material to be located as represented by the following general formula (30b) because the energy gap Eg _77K at 77 [K] can be kept high.

(In the general formula (30b),
X ₃₁ , X ₃₂ , X ₃₄ , and X ₃₆ are each independently a nitrogen atom or CR ₃₁ ,
Y ₃₁ , Y ₃₂ , Y _{34 to} Y ₃₈ are each independently a nitrogen atom, CR ₃₂ , or a carbon atom that binds to another atom in the molecule of the third material,
R ₃₁ and R ₃₂ are each independently a hydrogen atom or a substituent, and the substituent in R ₃₁ and R ₃₂ is a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, substituted or unsubstituted trialkylsilyl group, substituted or unsubstituted arylalkylsilyl group, substituted or unsubstituted triarylsilyl group, substituted or unsubstituted Selected from the group consisting of a substituted diarylphosphine oxide group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. a substituent, provided that the _{R 31} and substituted or unsubstituted forming the aromatic ring having 6 to 30 carbon atoms in the _{R 32} Hydrocarbon group is a non-fused ring,
Y ₃₉ is NR ₃₃ , an oxygen atom, or a sulfur atom,
R ₃₃ is a substituent, and the substituent in R ₃₃ is a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms. Substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted An arylthio group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted ring A substituent selected from the group consisting of an aromatic hydrocarbon group having 6 to 30 carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, Aromatic hydrocarbon group or a substituted or unsubstituted ring formed of 6 to 30 carbon atoms for the R ₃₃ is non-fused rings,
X ₃₂ and Y ₃₄ may be cross-linked via an oxygen atom, a sulfur atom, or CR ₅₁ R ₅₂ ,
X ₃₄ and Y ₃₂ may be bridged via an oxygen atom, a sulfur atom, or CR ₅₃ R ₅₄ ,
R _{51 to} R ₅₄ are each independently synonymous with the substituent in R ₃₃ ,
In the general formula (30b), a wavy line portion represents a bonding site with another atom or another structure in the molecule of the third material. )

For example, in the general formula (30b), when X ₃₂ and Y ₃₄ are cross-linked via an oxygen atom, a sulfur atom, or CR ₅₁ R ₅₂ , they are represented by the following general formula (30b-1). .

However, in the general formula _{(30b-1), Z 31} represents an oxygen atom, a sulfur atom, or a _CR 51 _{R 52.}

In the present embodiment, the third material preferably includes a group represented by the following general formula (30c).
Positioning the bonding site as represented by the following general formula (30c) is preferable as the third material because the energy gap Eg _77K at 77 [K] can be kept high.

(In the general formula (30c),
X ₃₁ , X ₃₂ , X ₃₄ , and X ₃₆ are each independently a nitrogen atom or CR ₃₁ ,
Y ₃₁ , Y ₃₂ , Y ₃₄ , Y ₃₅ , Y ₃₇ , Y ₃₈ are each independently a nitrogen atom or CR ₃₂ ,
Y _{41 to} Y ₄₅ , Y ₄₇ and Y ₄₈ are each independently a nitrogen atom, CR ₃₄ , or a carbon atom bonded to another atom in the molecule of the third material;
R ₃₁ , R ₃₂ , and R ₃₄ are each independently a hydrogen atom or a substituent, and the substituent in R ₃₁ , R ₃₂ , and R ₃₄ is a halogen atom, a cyano group, a substituted or unsubstituted carbon number of 1 -30 alkyl group, substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, substituted or unsubstituted trialkylsilyl group, substituted or unsubstituted arylalkylsilyl group, substituted or unsubstituted triaryl From a silyl group, a substituted or unsubstituted diarylphosphine oxide group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms comprising a substituent selected from the group, provided that the _{R 31,} wherein _{R 32,} a substituted or unsubstituted ring-shaped in the _{R 34} Aromatic hydrocarbon group having 6 to 30 carbon atoms is a non-fused ring,
Y ₃₉ is NR ₃₃ , an oxygen atom, or a sulfur atom,
Y ₄₉ is NR ₃₅ , an oxygen atom, or a sulfur atom,
R ₃₃ and R ₃₅ are each independently a substituent, and the substituent in R ₃₃ and R ₃₅ is a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring. A cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted carbon number of 1 -20 alkylthio group, substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 50 carbon atoms A group consisting of an arylsilyl group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. Is a substituent et selected, provided that the R _33, an aromatic hydrocarbon group or a substituted or unsubstituted ring formed of 6 to 30 carbon atoms for the R ₃₅ represents a non-fused ring,
X ₃₂ and Y ₃₄ may be cross-linked via an oxygen atom, a sulfur atom, or CR ₅₁ R ₅₂ ,
X ₃₄ and Y ₃₂ may be bridged via an oxygen atom, a sulfur atom, or CR ₅₃ R ₅₄ ,
R _{51 to} R ₅₄ each independently have the same meaning as the substituent in R ₃₃ and R ₃₅ ,
In the general formula (30c), a wavy line portion represents a bonding site with another atom or another structure in the molecule of the third material. )

For example, in the general formula (30c), when X ₃₂ and Y ₃₄ are cross-linked via an oxygen atom, a sulfur atom, or CR ₅₁ R ₅₂ , they are represented by the following general formula (30c-1). .

However, in the general formula _{(30c-1), Z 32} represents an oxygen atom, a sulfur atom, or a _CR 51 _{R 52.}

In the present embodiment, it is preferable that the third material includes a group represented by the following general formula (30d).
Positioning the bonding site as represented by the following general formula (30d) is preferable as the third material because the energy gap Eg _77K at 77 [K] can be kept high.

(In the general formula (30d),
X ₃₁ , X ₃₂ , X ₃₄ , and X ₃₆ are each independently a nitrogen atom or CR ₃₁ ,
X ₄₁ , X ₄₃ , X ₄₄ , and X ₄₅ are each independently a nitrogen atom or CR ₃₆ ,
R ₃₁ and R ₃₆ are each independently a substituent, and the substituent in R ₃₁ and R ₃₆ is a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted group. Substituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted trialkylsilyl group, substituted or unsubstituted arylalkylsilyl group, substituted or unsubstituted triarylsilyl group, substituted or unsubstituted diaryl A substituent selected from the group consisting of a phosphine oxide group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. There, however, the _{R 31,} an aromatic hydrocarbon group substituted or unsubstituted ring formed of 6 to 30 carbon atoms for the _{R 36} is unfused rings Yes,
X ₃₂ and X ₄₁ may be cross-linked via an oxygen atom, a sulfur atom, or CR ₅₅ R ₅₆ ,
X ₃₄ and X ₄₅ may be cross-linked via an oxygen atom, a sulfur atom, or CR ₅₇ R ₅₈ ,
R ₅₅ to R ₅₈ are each independently a substituent, the substituent in the _R 55 _{to R 58} is a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted Substituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted An alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms, a substituted or unsubstituted ring carbon number 6 ˜50 arylsilyl groups, substituted or unsubstituted aromatic hydrocarbon groups having 6 to 30 ring carbon atoms, and substituted or unsubstituted heterocyclic groups having 5 to 30 ring atoms Is a substituent selected from the group consisting of groups, provided that an aromatic hydrocarbon group substituted or unsubstituted ring formed of 6 to 30 carbon atoms for the R ₅₅ to R ₅₈ is a non-fused ring,
In the general formula (30d), the wavy line portion represents a bonding site with another atom or another structure in the molecule of the third material. )

For example, in the general formula (30d), when X ₃₂ and X ₄₁ are cross-linked via an oxygen atom, a sulfur atom, or CR ₅₅ R ₅₆ , they are represented by the following general formula (30d-1). .

However, in the general formula _{(30d-1), Z 33} represents an oxygen atom, a sulfur atom, or a _CR 55 _{R 56.}

In the present embodiment, the third material preferably includes a group represented by the following general formula (30e).
It is preferable for the third material to be located as represented by the following general formula (30e) because the energy gap Eg _77K at 77 [K] can be kept high.

(In the general formula (30e),
X ₃₁ , X ₃₂ , X ₃₄ , and X ₃₆ are each independently a nitrogen atom or CR ₃₁ ,
X ₄₁ , X ₄₃ , X ₄₄ , and X ₄₅ are each independently a nitrogen atom or CR ₃₆ ,
Y _{31 to} Y ₃₅ , Y ₃₇ and Y ₃₈ are each independently a nitrogen atom, CR ₃₂ , or a carbon atom bonded to another atom in the molecule of the third material,
R ₃₁ , R ₃₂ and R ₃₆ are each independently a hydrogen atom or a substituent, and the substituent in R ₃₁ , R ₃₂ and R ₃₆ is a halogen atom, a cyano group, a substituted or unsubstituted carbon number of 1 -30 alkyl group, substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, substituted or unsubstituted trialkylsilyl group, substituted or unsubstituted arylalkylsilyl group, substituted or unsubstituted triaryl From a silyl group, a substituted or unsubstituted diarylphosphine oxide group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms comprising a substituent selected from the group, provided that the _{R 31,} wherein _{R 32,} a substituted or unsubstituted ring-shaped in the _{R 36} Aromatic hydrocarbon group having 6 to 30 carbon atoms is a non-fused ring,
Y ₃₉ is NR ₃₃ , an oxygen atom, or a sulfur atom,
R ₃₃ is a substituent, and the substituent in R ₃₃ is a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms. Substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted An arylthio group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted ring A substituent selected from the group consisting of an aromatic hydrocarbon group having 6 to 30 carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, Aromatic hydrocarbon group or a substituted or unsubstituted ring formed of 6 to 30 carbon atoms for the R ₃₃ is non-fused rings,
X ₃₂ and X ₄₁ may be cross-linked via an oxygen atom, a sulfur atom, or CR ₅₅ R ₅₆ ,
X ₃₄ and X ₄₅ may be cross-linked via an oxygen atom, a sulfur atom, or CR ₅₇ R ₅₈ ,
X ₄₁ and Y ₃₇ may be cross-linked via an oxygen atom, a sulfur atom, or CR ₅₉ R ₆₀ ,
X ₄₃ and Y ₃₅ may be cross-linked via an oxygen atom, a sulfur atom, or CR ₆₁ R ₆₂ ,
R ₅₅ to R ₆₂ each independently has the same meaning as the substituent in the _{R 33,}
In the general formula (30e), the wavy line portion represents a bonding site with another atom or another structure in the molecule of the third material. )

For example, in the general formula (30e), when X ₃₂ and X ₄₁ are cross-linked via an oxygen atom, a sulfur atom, or CR ₅₅ R ₅₆ , they are represented by the following general formula (30e-1). .

However, in the general formula _{(30e-1), Z 34} represents an oxygen atom, a sulfur atom, or a _CR 55 _{R 56.}

For example, in the general formula (30e), when X ₄₁ and Y ₃₇ are cross-linked through an oxygen atom, a sulfur atom, or CR ₅₉ R ₆₀ , they are represented by the following general formula (30e-2). .

However, in the general formula _{(30e-2), Z 35} represents an oxygen atom, a sulfur atom, or a _CR 59 _{R 60.}

In the present embodiment, it is preferable that the third material includes a group represented by the following general formula (30f).
Positioning the bonding site as represented by the following general formula (30f) is preferable as the third material because the energy gap Eg _77K at 77 [K] can be kept high.

(In the general formula (30f),
Y ₃₁ , Y ₃₂ , Y ₃₄ , Y ₃₅ , Y ₃₇ , Y ₃₈ are each independently a nitrogen atom or CR ₃₂ ,
Y _{41 to} Y ₄₅ , Y ₄₇ and Y ₄₈ are each independently a nitrogen atom, CR ₃₄ , or a carbon atom bonded to another atom in the molecule of the third material;
R ₃₂ and R ₃₄ are each independently a hydrogen atom or a substituent, and the substituent in R ₃₂ and R ₃₄ is a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, substituted or unsubstituted trialkylsilyl group, substituted or unsubstituted arylalkylsilyl group, substituted or unsubstituted triarylsilyl group, substituted or unsubstituted Selected from the group consisting of a substituted diarylphosphine oxide group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. a substituent, provided that the _{R 32,} a substituted or unsubstituted ring formed C6-30 aromatic hydrocarbon in the _{R 34} It is a non-fused ring,
Y ₃₉ is NR ₃₃ , an oxygen atom, or a sulfur atom,
Y ₄₉ is NR ₃₅ , an oxygen atom, or a sulfur atom,
R ₃₃ and R ₃₅ are each independently a hydrogen atom or a substituent. The substituent in R ₃₃ and R ₃₅ is a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted group. Substituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted An alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms, a substituted or unsubstituted ring carbon number 6 ~ 50 arylsilyl groups,
A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, provided that The substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R ₃₃ and R ₃₅ is a non-condensed ring,
In the general formula (30f), a wavy line portion represents a bonding site with another atom or another structure in the molecule of the third material. )

  In the present embodiment, the third material may include a group represented by at least one of the following general formula (30g), the following general formula (30h), and the following general formula (30i).

In the general formula (30g), the general formula (30h), and the general formula (30i), Y _{31 to} Y ₃₈ , Y _{41 to} Y ₄₈ , and Y _{51 to} Y ₅₈ are each independently a nitrogen atom, CR ₃₇ Or a carbon atom bonded to another atom in the molecule of the third material,
R ₃₇ each independently represents a hydrogen atom or a substituent. The substituent in R ₃₇ is a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted ring. C3-C30 cycloalkyl group, substituted or unsubstituted trialkylsilyl group, substituted or unsubstituted arylalkylsilyl group, substituted or unsubstituted triarylsilyl group, substituted or unsubstituted diarylphosphine oxide group A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, The substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R ₃₇ is a non-condensed ring,
Y ₄₉ and Y ₅₉ are each independently NR ₃₈ , an oxygen atom, or a sulfur atom, and R ₃₈ is each independently a hydrogen atom or a substituent, and the substituent in R ₃₈ is a halogen atom, A cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or Unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, substituted or unsubstituted An alkylsilyl group having 3 to 50 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted ring carbon number 6 to 3 A substituent selected from the group consisting of 0 aromatic hydrocarbon groups and substituted or unsubstituted heterocyclic groups having 5 to 30 ring atoms, provided that R ₃₈ is substituted or unsubstituted. The aromatic hydrocarbon group having 6 to 30 carbon atoms is a non-condensed ring,
In the general formula (30g), the general formula (30h), and the general formula (30i), a wavy line portion represents a bonding site with another atom or another structure in the molecule of the third material.
The general formula (32), the general formula (35), the general formula (36), the general formula (37), the general formula (38), the general formula (39), and the general formula (30a). In the general formula (30b), the general formula (30c), the general formula (30e), the general formula (30f), the general formula (30h), and the general formula (30i), Y ₃₉ and Y ₄₉ are When each is independently an oxygen atom or a sulfur atom, the ionization potential Ip is large, so that it is preferable as the third material, and when it is an oxygen atom, the ionization potential Ip is larger, more preferable.

  In the present embodiment, the third material is also preferably an aromatic hydrocarbon compound or an aromatic heterocyclic compound.

-Production method of third material The third material of the general formula is, for example, International Publication No. 2012/153780 (WO2012 / 153780A1) or International Publication No. 2013/038650 (WO2013-03).
8650 A1).

  Specific examples of the substituent in the third material according to the present embodiment are as follows, for example, but the present invention is not limited to these specific examples.

Specific examples of the aromatic hydrocarbon group (aryl group) include phenyl, tolyl, xylyl, naphthyl, phenanthryl, pyrenyl, chrysenyl, benzo [c] phenanthryl, benzo [g] chrysenyl. Group, benzoanthryl group, triphenylenyl group, fluorenyl group, 9,9-dimethylfluorenyl group, benzofluorenyl group, dibenzofluorenyl group, biphenyl group, terphenyl group, quarterphenyl group, fluoranthenyl group Preferably, a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, a naphthyl group, a triphenylenyl group, a fluorenyl group and the like can be mentioned.
Examples of the aromatic hydrocarbon group having a substituent include a tolyl group, a xylyl group, and a 9,9-dimethylfluorenyl group.
As specific examples indicate, aryl groups include both fused and non-fused aryl groups.
As the aromatic hydrocarbon group, a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, a naphthyl group, a triphenylenyl group, and a fluorenyl group are preferable.
In the case of an organic EL device in which the light emitting layer emits blue light, the aromatic hydrocarbon group as a substituent in the third material is preferably a non-condensed aromatic hydrocarbon group.

Specific examples of the aromatic heterocyclic group (heteroaryl group, heteroaromatic ring group, heterocyclic group) include pyrrolyl group, pyrazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, pyridyl group, triazinyl group, indolyl group, Isoindolyl group, imidazolyl group, benzimidazolyl group, indazolyl group, imidazo [1,2-a] pyridinyl group, furyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, azadibenzofuranyl group, thiophenyl group, Benzothiophenyl group, dibenzothiophenyl group, azadibenzothiophenyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, quinazolinyl group, naphthyridinyl group, carbazolyl group, azacarbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl Group, fe Examples include a dinyl group, a phenothiazinyl group, a phenoxazinyl group, an oxazolyl group, an oxadiazolyl group, a furanyl group, a benzoxazolyl group, a thienyl group, a thiazolyl group, a thiadiazolyl group, a benzthiazolyl group, a triazolyl group, and a tetrazolyl group. Examples thereof include a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, an azadibenzofuranyl group, and an azadibenzothiophenyl group.
As the aromatic heterocyclic group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, pyridyl group, pyrimidinyl group, triazinyl group, azadibenzofuranyl group, azadibenzothiophenyl group are preferable, dibenzofuranyl group, dibenzofuranyl group A thiophenyl group, an azadibenzofuranyl group, and an azadibenzothiophenyl group are more preferable.

  Specific examples of the trialkylsilyl group include a trimethylsilyl group and a triethylsilyl group. Specific examples of the substituted or unsubstituted arylalkylsilyl group include a diphenylmethylsilyl group, a ditolylmethylsilyl group, and a phenyldimethylsilyl group. Specific examples of the substituted or unsubstituted triarylsilyl group include a triphenylsilyl group and a tolylsilylsilyl group.

  Specific examples of the diarylphosphine oxide group include a diphenylphosphine oxide group and a ditolylphosphine oxide group.

Further, when R ₁ , R _a , Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ have a substituent, the substituent is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted. A cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted trialkylsilyl group, a substituted or unsubstituted arylalkylsilyl group, a substituted or unsubstituted triarylsilyl group, a substituted or unsubstituted diarylphosphine An oxide group, a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 ring atoms, and preferably substituted. Or an unsubstituted aromatic hydrocarbon ring group having 6 to 30 carbon atoms or a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 ring atoms, and aromatic Specific examples of the hydrogenated ring group include phenyl group, tolyl group, xylyl group, naphthyl group, phenanthryl group, pyrenyl group, chrysenyl group, benzo [c] phenanthryl group, benzo [g] chrysenyl group, benzoanthryl group, Triphenylenyl group, fluorenyl group, 9,9-dimethylfluorenyl group, benzofluorenyl group, dibenzofluorenyl group, biphenyl group, terphenyl group, quarterphenyl group, fluoranthenyl group, etc., and aromatic Specific examples of the heterocyclic group include pyrrolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridyl, triazinyl, indolyl, isoindolyl, imidazolyl, benzimidazolyl, indazolyl, imidazol [1, 2-a] pyridinyl group, furyl group, benzofura Nyl group, isobenzofuranyl group, dibenzofuranyl group, azadibenzofuranyl group, thiophenyl group, benzothiophenyl group, dibenzothiophenyl group, azadibenzothiophenyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, quinazolinyl group , Naphthyridinyl group, carbazolyl group, azacarbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, phenothiazinyl group, phenoxazinyl group, oxazolyl group, oxadiazolyl group, furazanyl group, benzoxazolyl group, Examples include thienyl group, thiazolyl group, thiadiazolyl group, benzthiazolyl group, triazolyl group, tetrazolyl group and the like.
In the case of an organic EL device in which the light emitting layer emits blue light, the aromatic heterocyclic group as a substituent in the third material is preferably a non-condensed aromatic heterocyclic group.

  Specific examples of the third material according to this embodiment are shown below. The third material in the present invention is not limited to these specific examples.

(Relationship between the first material, the second material, and the third material in the light emitting layer)
In the present embodiment, the third material is considered to have a function as a dispersion material that suppresses molecular association of the second materials according to the above-described embodiment in the light emitting layer.
Since the second material according to the present embodiment is a thermally activated delayed fluorescent material, it tends to cause molecular association. The excitation energy (singlet energy or triplet energy) of the molecular aggregate is smaller than that of the monomer. Therefore, when the concentration of the second material is increased in the thin film, energy loss due to molecular association is predicted.
Therefore, particularly when a blue fluorescent material having a large excitation energy is used, energy loss due to the use of the third material can be suppressed, and the efficiency of the light emitting element can be improved. Further, even in a light emitting material that emits light in a wavelength range from a wavelength region that emits red light to a wavelength region that emits yellow light, a carrier balance factor is improved, which can contribute to an improvement in efficiency of the light emitting element.
In conventional fluorescent and phosphorescent light-emitting elements, it is difficult to consider the improvement in luminous efficiency as shown in this embodiment by adding a third material having a function other than the host material and the light-emitting material to the light-emitting layer. It was. However, in the thermally activated delayed fluorescence type light emitting device of this embodiment, the thermally activated delayed fluorescent material having a relatively small singlet energy is responsible for carrier transport in the light emitting layer, and a third material having a larger singlet energy. However, there is a possibility that the carrier balance factor will be greatly changed. As a result, the efficiency of the light emitting element can be improved.
Since the singlet energy of the third material is higher than the singlet energy of the second material, the excited third material is unstable compared to the first material and the second material. Therefore, it is preferable that the third material does not participate in exciton generation or carrier transport in the light emitting layer. Such a third material is specific from the selection criteria of the material to be included in the light emitting layer in the conventional organic EL element. In conventional fluorescent light emitting organic EL elements, a material having a high electrical and photochemical function is selected and contained in the light emitting layer. This is because the third material is intentionally included in the light emitting layer.

In the present embodiment, the singlet energy EgS (M2) of the second material is preferably larger than the singlet energy EgS (M1) of the first material.
That is, it is preferable to satisfy the relationship of EgS (M1) <EgS (M2) <EgS (M3).

In this embodiment, the energy gap Eg _77K (M2) at 77 [K] of the second material is larger than the energy gap Eg _77K (M1) at 77 [K] of the first material, and the third material The energy gap Eg _77K (M3) at 77 [K] of the material is preferably larger than the energy gap Eg _77K (M2) at 77 [K] of the second material.
That is, it is preferable to satisfy the relationship of Eg _77K (M1) <Eg _77K (M2) <Eg _77K (M3).

In this embodiment, the difference ΔST (M2) between the singlet energy EgS (M2) of the second material and the energy gap Eg _77K (M2) at 77 [K] of the second material is expressed by the following formula ( It is preferable to satisfy the relationship of equation (1).
ΔST (M2) = EgS (M2) −Eg _77K (M2) <0.3 [eV] (Equation 1)
ΔST (M2) is preferably less than 0.2 [eV].

In this embodiment, the difference ΔST (M1) between the singlet energy EgS (M1) of the first material and the energy gap Eg _77K (M1) at 77 [K] of the first material is expressed by the following formula ( It is preferable to satisfy the relationship of Formula 2).
ΔST (M1) = EgS (M1) −Eg _77K (M1)> 0.3 [eV] (Equation 2)

In this embodiment, the difference ΔST (M3) between the singlet energy EgS (M3) of the third material and the energy gap Eg _77K (M3) at 77 [K] of the third material is expressed by the following formula ( It is preferable to satisfy the relationship of Equation 3).
ΔST (M3) = EgS (M3) −Eg _77K (M3)> 0.3 [eV] (Equation 3)

In the present embodiment, the energy gap Eg _77K (M3) at 77 [K] of the third material is preferably 2.9 eV or more. When the third material has such an energy gap Eg _77K (M3), the third material can be hardly involved in exciton generation or carrier transport in the light emitting layer.

・ ΔST
In order to reduce ΔST which is equivalent to the difference between the singlet energy EgS and the triplet energy EgT, quantum exchange is realized by a small exchange interaction between the singlet energy EgS and the triplet energy EgT. The physical details of the relationship between ΔST and exchange interaction are described in, for example, the following Reference 1 and Reference 2.
Reference 1: Chiyaya Adachi et al., Organic EL Discussion Session 10th Annual Meeting Proceedings, S2-5, p11-12
Reference 2: Katsumi Tokumaru, Organic Photochemical Reaction Theory, Tokyo Kagaku Doujin Publishing, (1973)
Such a material can be synthesized by molecular design by quantum calculation. Specifically, it is a compound localized so as not to overlap the LUMO and HOMO electron orbitals.
An example of a compound having a small ΔST used for the second material of the present embodiment is a compound in which a donor element and an acceptor element are combined in the molecule, and further, electrochemical stability (redox stability) is considered. And compounds having ΔST of 0 eV or more and less than 0.3 eV.
Further, a more preferable compound is a compound that forms an aggregate in which dipoles formed in an excited state of a molecule interact with each other and exchange interaction energy becomes small. According to the study by the present inventors, such a compound has approximately the same dipole direction, and ΔST can be further reduced by molecular interaction. In such a case, ΔST can be extremely small, from 0 eV to 0.2 eV.

-TADF mechanism In the organic EL device of the present embodiment, it is preferable to use a compound having a small ΔST (M2) as the second material, and from the triplet level of the second material to the second material by externally applied thermal energy. Inverse intersystem crossing to the singlet level of this material is likely to occur. An energy state conversion mechanism in which the excited triplet state of the electrically excited exciton inside the organic EL element is spin-exchanged to the excited singlet state by crossing between inverse terms is called a TADF mechanism.
FIG. 4 shows an example of the relationship between the energy levels of the first material, the second material, and the third material in the light emitting layer. In FIG. 4, S0 represents the ground state, S1 (M1) represents the lowest excited singlet state of the first material, T1 (M1) represents the lowest excited triplet state of the first material, S1 (M2) represents the lowest excited singlet state of the second material, T1 (M2) represents the lowest excited triplet state of the second material, and S1 (M3) represents the lowest material of the third material. It represents an excited singlet state, and T1 (M3) represents the lowest excited triplet state of the third material. The dashed arrow from S1 (M2) to S1 (M1) in FIG. 4 represents the Forster energy transfer from the lowest excited singlet state of the second material to the lowest excited singlet state of the first material. .
As shown in FIG. 4, when a material having a small ΔST (M2) is used as the second material, the lowest excited triplet state T1 (M2) is changed to the lowest excited singlet state S1 (M2) by thermal energy. Intersection is possible. Then, a Forster energy transfer occurs from the second material lowest excited singlet state S1 (M2) to the lowest excited singlet state S1 (M1) of the first material. As a result, fluorescence emission from the lowest excited singlet state S1 (M1) of the first material can be observed. It is believed that the internal efficiency can theoretically be increased to 100% also by utilizing delayed fluorescence due to this TADF mechanism.

-Relationship between triplet energy and energy gap at 77 [K] Here, the relationship between triplet energy and energy gap at 77 [K] will be described. In the present embodiment, the energy gap at 77 [K] is different from the normally defined triplet energy.
For the first material and the third material to be measured, the triplet energy is measured as follows. A compound to be measured is dissolved in EPA (diethyl ether: isopentane: ethanol = 5: 5: 2 (volume ratio)) so as to have a concentration of 10 μmol / L, and this solution is placed in a quartz cell and measured. A sample was used. With respect to this measurement sample, a phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) is measured at a low temperature (77 [K]), and a tangent line is drawn with respect to the rising edge of the phosphorescence spectrum on the short wavelength side. Based on the wavelength value λ _edge [nm] at the intersection of the tangent and the horizontal axis, the energy amount calculated from the following conversion formula 1 was defined as an energy gap Eg _77K at 77 [K].
Conversion formula 1: Eg _77K [eV] = 1239.85 / λ _edge
For measurement of phosphorescence, an F-4500 spectrofluorometer main body manufactured by Hitachi High-Technology Co., Ltd. was used. Note that the phosphorescence measuring apparatus is not limited to the apparatus used here.
The tangent to the rising edge on the short wavelength side of the phosphorescence spectrum is drawn as follows. When moving on 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, tangents at each point on the curve are considered toward the long wavelength side. The slope of this tangent line increases as the curve rises (that is, as the vertical axis increases). A tangent drawn at a point where the value of the slope takes a maximum value (that is, a tangent at the inflection point) is a tangent to the rising edge of the phosphorescence spectrum on the short wavelength side.
Note that the maximum point having a peak intensity of 15% or less of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and has the maximum slope value closest to the maximum value on the shortest wavelength side. The tangent drawn at the point where the value is taken is taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side.
Regarding the second material to be measured, the triplet energy is measured as follows. A compound (second material) to be measured and the compound TH-2 are co-evaporated on a quartz substrate, and a sample sealed in an NMR tube is prepared. This sample was produced under the following conditions.
Quartz substrate / TH-2: second material (film thickness 100 nm, second material concentration: 12% by mass)
With respect to this measurement sample, a phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) is measured at a low temperature (77 [K]), and a tangent line is drawn with respect to the rising edge of the phosphorescence spectrum on the short wavelength side. Based on the wavelength value λ _edge [nm] at the intersection of the tangent and the horizontal axis, the energy amount calculated from the following conversion formula 2 was defined as an energy gap Eg _77K at 77 [K].
Conversion formula 2: Eg _77K [eV] = 1239.85 / λ _edge
For measurement of phosphorescence, an F-4500 spectrofluorometer main body manufactured by Hitachi High-Technology Co., Ltd. was used. Note that the phosphorescence measuring apparatus is not limited to the apparatus used here.
The tangent to the short-wavelength rise of the phosphorescence spectrum is drawn in the same manner as the tangent drawing in the phosphorescence spectra of the first material and the third material.
Here, the second material used in the present embodiment is preferably a compound having a small ΔST. When ΔST is small, intersystem crossing and reverse intersystem crossing easily occur even in a low temperature (77 [K]) state, and an excited singlet state and an excited triplet state are mixed. As a result, the spectrum measured in the same manner as described above includes light emission from both the excited singlet state and the excited triplet state, and it is difficult to distinguish from which state the light is emitted. However, basically, the triplet energy value is considered to be dominant.
Therefore, in the present embodiment, the measurement method is the same as that of the normal triplet energy EgT, but in order to distinguish the difference in strict meaning, the value measured as follows is referred to as an energy gap Eg _77K. .

・ Singlet energy EgS
Singlet energy EgS is measured as follows.
A 10 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell, and the absorption spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample was measured at room temperature (300 K). A single line energy was calculated by drawing a tangent line to the long wavelength falling edge of the absorption spectrum and substituting the wavelength value λ _edge [nm] at the intersection of the tangent line and the horizontal axis into the following conversion formula 3. .
Conversion formula 3: EgS [eV] = 1239.85 / λ _edge
In this example, the absorption spectrum was measured with a spectrophotometer manufactured by Hitachi (device name: U3310). Note that the absorption spectrum measuring apparatus is not limited to the apparatus used here.

In this embodiment, the difference between the singlet energy EgS and the energy gap Eg _77K is defined as ΔST.

In the present embodiment, it is preferable that the ionization potential Ip (M3) of the third material and the ionization potential Ip (M2) of the second material satisfy the relationship of the following mathematical formula (Formula 4). By satisfying this relationship, it is possible to make the third material hardly participate in exciton generation and carrier transport in the light emitting layer.
Ip (M3) ≧ Ip (M2) (Equation 4)

  In the present embodiment, the ionization potential Ip (M3) of the third material is preferably 6.3 eV or more. When the third material has such an ionization potential Ip (M3), the third material can be hardly involved in exciton generation and carrier transport in the light emitting layer.

  The ionization potential can be measured using a photoelectron spectrometer in the atmosphere. Specifically, the measurement was performed by irradiating the material with light and measuring the amount of electrons generated by charge separation at that time. Examples of the measuring device include a photoelectron spectrometer (device name: AC-3) manufactured by Riken Keiki Co., Ltd.

In this embodiment, it is preferable that the electron affinity Af (M3) of the third material and the electron affinity Af (M2) of the second material satisfy the relationship of the following mathematical formula (Formula 5). By satisfying this relationship, it is possible to make the third material hardly participate in exciton generation and carrier transport in the light emitting layer.
Af (M3) ≦ Af (M2) (Equation 5)

  In the present embodiment, the electron affinity Af (M3) of the third material is preferably 6.3 eV or more. When the third material has such an electron affinity Af (M3), it is possible to make the third material hardly participate in exciton generation or carrier transport in the light emitting layer.

The electron affinity (affinity) can be calculated from the following calculation formula (Formula 8) using the ionization potential Ip of the compound and the measured singlet energy EgS measured by the method described above.
Af = Ip−EgS (Equation 8)

-Film thickness of light emitting layer The film thickness of the light emitting layer in the organic EL device of the present embodiment is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and most preferably 10 nm to 50 nm. If the thickness is less than 5 nm, it is difficult to form a light emitting layer and the adjustment of chromaticity may be difficult, and if it exceeds 50 nm, the driving voltage may increase.

-Content rate of the material in a light emitting layer In the organic EL element of this embodiment, it is preferable that the content rate of a 1st material is 0.01 to 10 mass% in a light emitting layer, and is 2nd material. The content of is preferably 1% by mass or more and 75% by mass or less, and the content of the third material is preferably 1% by mass or more and 75% by mass or less. The upper limit of the total content of the first material, the second material, and the third material in the light emitting layer is 100% by mass. In addition, this embodiment does not exclude that a material other than the first material, the second material, and the third material is included in the light emitting layer.

(substrate)
The substrate is used as a support for the organic EL element. For example, glass, quartz, plastic, or the like can be used as the substrate. Further, a flexible substrate may be used. The flexible substrate is a substrate that can be bent (flexible), and is made of, for example, polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, or polyethylene naphthalate. Examples include a plastic substrate. Moreover, an inorganic vapor deposition film can also be used.

(anode)
For the anode formed on the substrate, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a high work function (specifically, 4.0 eV or more). Specifically, for example, indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, and indium oxide containing zinc oxide. And graphene. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium ( Pd), titanium (Ti), or a metal material nitride (for example, titanium nitride).
These materials are usually formed by sputtering. For example, indium oxide-zinc oxide can be formed by a sputtering method by using a target in which 1% by mass to 10% by mass of zinc oxide is added to indium oxide. For example, indium oxide containing tungsten oxide and zinc oxide contains 0.5% by mass to 5% by mass of tungsten oxide and 0.1% by mass to 1% by mass of zinc oxide with respect to indium oxide. By using a target, it can be formed by a sputtering method. In addition, you may produce by the vacuum evaporation method, the apply | coating method, the inkjet method, a spin coat method etc.
Of the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that facilitates hole injection regardless of the work function of the anode. Any material that can be used as an electrode material (for example, a metal, an alloy, an electrically conductive compound, and a mixture thereof, and other elements belonging to Group 1 or Group 2 of the periodic table) can be used.
An element belonging to Group 1 or Group 2 of the periodic table, which is a material having a low work function, that is, an alkali metal such as lithium (Li) or cesium (Cs), and magnesium (Mg), calcium (Ca), or strontium Alkaline earth metals such as (Sr), and alloys containing these (eg, MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these can also be used. Note that when an anode is formed using an alkali metal, an alkaline earth metal, and an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Furthermore, when using a silver paste etc., the apply | coating method, the inkjet method, etc. can be used.

(cathode)
It is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a low work function (specifically, 3.8 eV or less) for the cathode. Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg) and calcium (Ca ), Alkaline earth metals such as strontium (Sr), and alloys containing these (for example, rare earth metals such as MgAg, AlLi), europium (Eu), ytterbium (Yb), and alloys containing these.
Note that in the case where the cathode is formed using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Moreover, when using a silver paste etc., the apply | coating method, the inkjet method, etc. can be used.
By providing an electron injection layer, a cathode is formed using various conductive materials such as Al, Ag, ITO, graphene, silicon or indium oxide-tin oxide containing silicon oxide regardless of the work function. can do. These conductive materials can be formed by a sputtering method, an inkjet method, a spin coating method, or the like.

(Hole injection layer)
The hole injection layer is a layer containing a substance having a high hole injection property. Substances with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, Tungsten oxide, manganese oxide, or the like can be used.
As a substance having a high hole injection property, 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4,4 ′, which is a low molecular organic compound, is used. , 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA), 4,4′-bis [N- (4-diphenylaminophenyl) -N-phenyl Amino] biphenyl (abbreviation: DPAB), 4,4′-bis (N- {4- [N ′-(3-methylphenyl) -N′-phenylamino] phenyl} -N-phenylamino) biphenyl (abbreviation: DNTPD), 1,3,5-tris [N- (4-diphenylaminophenyl) -N-phenylamino] benzene (abbreviation: DPA3B), 3- [N- (9-phenylcarbazol-3-yl) -N -F Enylamino] -9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA2), 3- Aromatic amine compounds such as [N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) amino] -9-phenylcarbazole (abbreviation: PCzPCN1), and dipyrazino [2,3-f: 20 , 30-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN).
As the substance having a high hole injecting property, a high molecular compound (an oligomer, a dendrimer, a polymer, or the like) can also be used. For example, poly (N-vinylcarbazole) (abbreviation: PVK), poly (4-vinyltriphenylamine) (abbreviation: PVTPA), poly [N- (4- {N ′-[4- (4-diphenylamino)] Phenyl] phenyl-N′-phenylamino} phenyl) methacrylamide] (abbreviation: PTPDMA), poly [N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl) benzidine] (abbreviation: Polymer compounds such as Poly-TPD). In addition, a polymer compound to which an acid such as poly (3,4-ethylenedioxythiophene) / poly (styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly (styrenesulfonic acid) (PAni / PSS) is added is used. You can also

(Hole transport layer)
The hole transport layer is a layer containing a substance having a high hole transport property. An aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used for the hole transport layer. Specifically, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) or N, N′-bis (3-methylphenyl) -N, N′— Diphenyl- [1,1′-biphenyl] -4,4′-diamine (abbreviation: TPD), 4-phenyl-4 ′-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: BAFLP), 4 , 4′-bis [N- (9,9-dimethylfluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: DFLDPBi), 4,4 ′, 4 ″ -tris (N, N-diphenylamino) ) Triphenylamine (abbreviation: TDATA), 4,4 ′, 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA), 4,4′-bis [N- (Spiro-9,9'-Biff Oren-2-yl) -N- phenylamino] biphenyl (abbreviation: BSPB) can be used aromatic amine compounds such as. The substances described here are mainly substances having a hole mobility of 10 −6 cm 2 / Vs or higher.
For the hole transport layer, CBP, 9- [4- (N-carbazolyl)] phenyl-10-phenylanthracene (CzPA), 9-phenyl-3- [4- (10-phenyl-9-anthryl) phenyl] A carbazole derivative such as -9H-carbazole (PCzPA) or an anthracene derivative such as t-BuDNA, DNA, or DPAnth may be used. A high molecular compound such as poly (N-vinylcarbazole) (abbreviation: PVK) or poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
Note that other than these substances, any substance that has a property of transporting more holes than electrons may be used. Note that the layer containing a substance having a high hole-transport property is not limited to a single layer, and two or more layers containing the above substances may be stacked.
When two or more hole transport layers are arranged, it is preferable to arrange a material having a larger energy gap on the side closer to the light emitting layer. An example of such a material is HT-2 used in Examples described later.

(Electron transport layer)
The electron transport layer is a layer containing a substance having a high electron transport property. For the electron transport layer, 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymer compounds Can be used. Specifically, as a low-molecular organic compound, Alq, tris (4-methyl-8-quinolinolato) aluminum (abbreviation: Almq ₃ ), bis (10-hydroxybenzo [h] quinolinato) beryllium (abbreviation: BeBq ₂ ), A metal complex such as BAlq, Znq, ZnPBO, ZnBTZ, or the like can be used. In addition to metal complexes, 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis [5- (Pert-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 3- (4-tert-butylphenyl) -4-phenyl-5- (4- Biphenylyl) -1,2,4-triazole (abbreviation: TAZ), 3- (4-tert-butylphenyl) -4- (4-ethylphenyl) -5- (4-biphenylyl) -1,2,4- Triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), 4,4′-bis (5-methylbenzoxazol-2-yl) stilbene (abbreviation: B) Heteroaromatic compounds such as zOs) can also be used. In this embodiment, a benzimidazole compound can be suitably used. The substances mentioned here are mainly substances having an electron mobility of 10 ⁻⁶ cm ² / Vs or higher. Note that any substance other than the above substances may be used for the electron-transport layer as long as the substance has a higher electron-transport property than the hole-transport property. Further, the electron-transport layer is not limited to a single layer, and two or more layers including the above substances may be stacked.
Moreover, a high molecular compound can also be used for an electron carrying layer. For example, poly [(9,9-dihexylfluorene-2,7-diyl) -co- (pyridine-3,5-diyl)] (abbreviation: PF-Py), poly [(9,9-dioctylfluorene-2) , 7-diyl) -co- (2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy) and the like can be used.

(Electron injection layer)
The electron injection layer is a layer containing a substance having a high electron injection property. For the electron injection layer, lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), lithium oxide (LiOx), etc. An alkali metal, an alkaline earth metal, or a compound thereof can be used. In addition, a substance in which an alkali metal, an alkaline earth metal, or a compound thereof is contained in a substance having an electron transporting property, specifically, a substance in which magnesium (Mg) is contained in Alq may be used. In this case, electron injection from the cathode can be performed more efficiently.
Alternatively, a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer. Such a composite material is excellent in electron injecting property and electron transporting property because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material excellent in transporting the generated electrons. Specifically, for example, a substance (metal complex, heteroaromatic compound, or the like) constituting the electron transport layer described above is used. be able to. The electron donor may be any substance that exhibits an electron donating property to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferable, and lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like can be given. Alkali metal oxides and alkaline earth metal oxides are preferable, and lithium oxide, calcium oxide, barium oxide, and the like can be given. A Lewis base such as magnesium oxide can also be used. Alternatively, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.

(Layer formation method)
The method for forming each layer of the organic EL element of the present embodiment is not limited except as specifically mentioned above, but a dry film forming method such as a vacuum evaporation method, a sputtering method, a plasma method, an ion plating method, a spin method, Known methods such as a coating method, a dipping method, a flow coating method, and a wet film forming method such as an ink jet method can be employed.

(Film thickness)
The film thickness of each organic layer of the organic EL element of the present 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 conversely, if it is too thick, it is high. Since an applied voltage is required and the efficiency is deteriorated, the range of several nm to 1 μm is usually preferable.

In this specification, the number of ring-forming carbon atoms constitutes the ring itself of a compound having a structure in which atoms are bonded cyclically (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, or a heterocyclic compound). Represents the number of carbon atoms in the atom. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbons. The “ring-forming carbon number” described below is the same unless otherwise specified. For example, the benzene ring has 6 ring carbon atoms, the naphthalene ring has 10 ring carbon atoms, the pyridinyl group has 5 ring carbon atoms, and the furanyl group has 4 ring carbon atoms. Further, when an alkyl group is substituted as a substituent on the benzene ring or naphthalene ring, the carbon number of the alkyl group is not included in the number of ring-forming carbons. In addition, for example, when a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring), the carbon number of the fluorene ring as a substituent is not included in the number of ring-forming carbons.
In this specification, the number of ring-forming atoms means a compound (for example, a monocyclic compound, a condensed ring compound, a bridging compound, a carbocyclic compound, a heterocyclic compound) having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic ring, a condensed ring, or a ring assembly). Of the ring compound) represents the number of atoms constituting the ring itself. An atom that does not constitute a ring (for example, a hydrogen atom that terminates a bond of an atom that constitutes a ring) or an atom contained in a substituent when the ring is substituted by a substituent is not included in the number of ring-forming atoms. The “number of ring-forming atoms” described below is the same unless otherwise specified. For example, the pyridine ring has 6 ring atoms, the quinazoline ring has 10 ring atoms, and the furan ring has 5 ring atoms. A hydrogen atom bonded to a carbon atom of a pyridine ring or a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms. Further, when, for example, a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring), the number of atoms of the fluorene ring as a substituent is not included in the number of ring-forming atoms.
Next, each substituent described in the general formula will be described.

Examples of the aromatic hydrocarbon group having 6 to 30 ring carbon atoms (aryl group) in the present embodiment include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a fluorenyl group, and a pyrenyl group. , Chrysenyl group, fluoranthenyl group, benzo [a] anthryl group, benzo [c] phenanthryl group, triphenylenyl group, benzo [k] fluoranthenyl group, benzo [g] chrysenyl group, benzo [b] triphenylenyl group, picenyl Group, perylenyl group and the like.
As an aryl group in this embodiment, it is preferable that ring formation carbon number is 6-20, More preferably, it is still more preferable that it is 6-12. Among the aryl groups, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a terphenyl group, and a fluorenyl group are particularly preferable. For the 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group and 4-fluorenyl group, the 9-position carbon atom is substituted with a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms in the present embodiment described later. It is preferable that

Examples of the heterocyclic group having 5 to 30 ring atoms (heteroaryl group) in the present embodiment include a pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolyl group, isoquinolinyl group, naphthyridinyl group, and phthalazinyl. Group, quinoxalinyl group, quinazolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, indolyl group, benzimidazolyl group, indazolyl group, imidazolpyridyl group Zinyl, benztriazolyl, carbazolyl, furyl, thienyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzofuranyl, benzothiophenyl , Benzoxazolyl group, benzothiazolyl group, benzisoxazolyl group, benzisothiazolyl group, benzoxiadiazolyl group, benzothiadiazolyl group, dibenzofuranyl group, dibenzothiophenyl group, piperidinyl group, pyrrolidinyl group , Piperazinyl group, morpholyl group, phenazinyl group, phenothiazinyl group, phenoxazinyl group and the like.
The number of ring-forming atoms of the heterocyclic group in this embodiment is preferably 5-20, and more preferably 5-14. Among the above heterocyclic groups, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3- A dibenzothiophenyl group, 4-dibenzothiophenyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, and 9-carbazolyl group are particularly preferable. With respect to the 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group and 4-carbazolyl group, the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms in the present embodiment or substitution on the 9th-position nitrogen atom Alternatively, an unsubstituted heterocyclic group having 5 to 30 ring atoms is preferably substituted.

In the present embodiment, the alkyl group having 1 to 30 carbon atoms may be linear, branched or cyclic. Examples of the linear or branched alkyl group include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, amyl group, isoamyl group, 1-methylpentyl group, 2-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1- A heptyloctyl group and a 3-methylpentyl group.
The linear or branched alkyl group in the present embodiment preferably has 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms. Among the linear or branched alkyl groups, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group , An amyl group, an isoamyl group, and a neopentyl group are particularly preferable.
Examples of the cycloalkyl group in this embodiment include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, an adamantyl group, and a norbornyl group. The ring-forming carbon number of the cycloalkyl group is preferably 3 to 10, and more preferably 5 to 8. Among the cycloalkyl groups, a cyclopentyl group and a cyclohexyl group are particularly preferable.
Examples of the halogenated alkyl group in which the alkyl group is substituted with a halogen atom include those in which the alkyl group having 1 to 30 carbon atoms is substituted with one or more halogen groups. Specific examples include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a trifluoromethylmethyl group, a trifluoroethyl group, and a pentafluoroethyl group.

  Examples of the alkylsilyl group having 3 to 30 carbon atoms in the present embodiment include a trialkylsilyl group having an alkyl group exemplified as the alkyl group having 1 to 30 carbon atoms, specifically, a trimethylsilyl group and a triethylsilyl group. , Tri-n-butylsilyl group, tri-n-octylsilyl group, triisobutylsilyl group, dimethylethylsilyl group, dimethylisopropylsilyl group, dimethyl-n-propylsilyl group, dimethyl-n-butylsilyl group, dimethyl-t- Examples thereof include a butylsilyl group, a diethylisopropylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, and a triisopropylsilyl group. The three alkyl groups in the trialkylsilyl group may be the same or different.

Examples of the arylsilyl group having 6 to 30 ring carbon atoms in the present embodiment include a dialkylarylsilyl group, an alkyldiarylsilyl group, and a triarylsilyl group.
The dialkylarylsilyl group includes, for example, a dialkylarylsilyl group having two alkyl groups exemplified for the alkyl group having 1 to 30 carbon atoms and one aryl group having 6 to 30 ring carbon atoms. . The carbon number of the dialkylarylsilyl group is preferably 8-30.
Examples of the alkyldiarylsilyl group include an alkyldiarylsilyl group having one alkyl group exemplified for the alkyl group having 1 to 30 carbon atoms and two aryl groups having 6 to 30 ring carbon atoms. . The alkyldiarylsilyl group preferably has 13 to 30 carbon atoms.
Examples of the triarylsilyl group include a triarylsilyl group having three aryl groups having 6 to 30 ring carbon atoms. The carbon number of the triarylsilyl group is preferably 18-30.

Alkoxy group having 1 to 30 carbon atoms in the present embodiment is represented as -OZ _1. Examples of _{Z 1,} include alkyl groups of 1 to 30 carbon atoms. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and a hexyloxy group.
Examples of the halogenated alkoxy group in which the alkoxy group is substituted with a halogen atom include those in which the C 1-30 alkoxy group is substituted with one or more halogen groups.

Aryloxy group ring forming C6-30 in this embodiment is expressed as -OZ _2. Examples of the Z ₂ include the aryl group having 6 to 30 ring carbon atoms. Examples of the aryloxy group include a phenoxy group.

Alkylamino group having 2 to 30 carbon atoms is represented as -NHR _V or -N _{(R V) 2,.} Examples of _{R V,} include alkyl groups of 1 to 30 carbon atoms.

The arylamino group having 6 to 60 ring carbon atoms is represented as —NHR _W or —N (R _W ) ₂ . Examples of R _W, and an aryl group the ring-forming C6-30.

Alkylthio group having 1 to 30 carbon atoms is represented as -SR _V. Examples of _{R V,} include alkyl groups of 1 to 30 carbon atoms.
Ring formation arylthio group having 6 to 30 carbon atoms is expressed as -SR _W. Examples of R _W, and an aryl group the ring-forming C6-30.

In the present invention, “ring-forming carbon” means a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring. “Ring-forming atom” means a carbon atom and a hetero atom constituting a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring).
In the present invention, the hydrogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (Protium), deuterium (Deuterium), and tritium (Tritium).

In addition, examples of the substituent in the present embodiment such as a substituent in the case of “substituted or unsubstituted”, a ring structure A, a ring structure B, a ring structure E, a ring structure F, a substituent in the ring structure G, etc. Aryl group, heterocyclic group, alkyl group (straight chain or branched chain alkyl group, cycloalkyl group, haloalkyl group), alkylsilyl group, arylsilyl group, alkoxy group, aryloxy group, alkylamino group, arylamino In addition to groups, alkylthio groups, and arylthio groups, alkenyl groups, alkynyl groups, aralkyl groups, halogen atoms, cyano groups, hydroxyl groups, nitro groups, and carboxy groups are exemplified.
Among the substituents mentioned here, an aryl group, a heterocyclic group, an alkyl group, a halogen atom, an alkylsilyl group, an arylsilyl group, and a cyano group are preferable, and further, specific examples that are preferable in the description of each substituent Are preferred.
These substituents may be further substituted with the above substituents. A plurality of these substituents may be bonded to each other to form a ring.

  The alkenyl group is preferably an alkenyl group having 2 to 30 carbon atoms, which may be linear, branched or cyclic, for example, vinyl group, propenyl group, butenyl group, oleyl group, eicosapentaenyl group. , Docosahexaenyl group, styryl group, 2,2-diphenylvinyl group, 1,2,2-triphenylvinyl group, 2-phenyl-2-propenyl group, cyclopentadienyl group, cyclopentenyl group, cyclohexenyl group And cyclohexadienyl group.

  The alkynyl group is preferably an alkynyl group having 2 to 30 carbon atoms, and may be linear, branched or cyclic, and examples thereof include ethynyl, propynyl, 2-phenylethynyl and the like.

As the aralkyl group, an aralkyl group having 6 to 30 ring carbon atoms is preferable and represented by -Z ₃ -Z ₄ . Examples of Z ₃ include alkylene groups corresponding to the alkyl groups having 1 to 30 carbon atoms. Examples of this Z ₄ include the above aryl group having 6 to 30 ring carbon atoms. This aralkyl group is an aralkyl group having 7 to 30 carbon atoms (the aryl moiety is 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms), and the alkyl moiety is 1 to 30 carbon atoms (preferably 1 to 1 carbon atoms). 20, more preferably 1-10, still more preferably 1-6). Examples of the aralkyl group include benzyl group, 2-phenylpropan-2-yl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, and phenyl-t-butyl. Group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β- Examples include naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.

  Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom is preferable.

The term “unsubstituted” in the case of “substituted or unsubstituted” means that a hydrogen atom is bonded without being substituted with the substituent.
In the present specification, “carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having XX to YY” represents the number of carbon atoms when the ZZ group is unsubstituted. The carbon number of the substituent when substituted is not included. Here, “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
In the present specification, “atom number XX to YY” in the expression “a ZZ group having a substituted or unsubstituted atom number XX to YY” represents the number of atoms when the ZZ group is unsubstituted, In this case, the number of substituent atoms is not included. Here, “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
In the compound described below or a partial structure thereof, the case of “substituted or unsubstituted” is the same as described above.

  In the present embodiment, a multiple linking group in which 2 to 4 groups selected from the aromatic hydrocarbon group are bonded, and a multiple in which 2 to 4 groups selected from the heterocyclic group are bonded. Examples of a linking group or a multiple linking group formed by bonding two to four groups selected from the aromatic hydrocarbon group and the heterocyclic group include the aromatic hydrocarbon group and the heterocyclic group. Examples thereof include a divalent group formed by bonding 2 to 4 groups selected. Examples of the multiple linking group formed by bonding 2 to 4 groups selected from the aromatic hydrocarbon group and the heterocyclic group include heterocyclic group-aromatic hydrocarbon group, aromatic hydrocarbon group-heterocycle Group, aromatic hydrocarbon group-heterocyclic group-aromatic hydrocarbon group, heterocyclic group-aromatic hydrocarbon group-heterocyclic group, aromatic hydrocarbon group-heterocyclic group-aromatic hydrocarbon group-heterocycle Group, heterocyclic group-aromatic hydrocarbon group-heterocyclic group-aromatic hydrocarbon group, and the like. Preferably, a divalent group formed by bonding the aromatic hydrocarbon group and the heterocyclic group one by one, that is, a heterocyclic group-aromatic hydrocarbon group, and an aromatic hydrocarbon group-heterocyclic group. . Specific examples of the aromatic hydrocarbon group and the heterocyclic group in these multiple linking groups include the groups described above for the aromatic hydrocarbon group and the heterocyclic group.

[Modification of Embodiment]
In addition, this invention is not limited to the above-mentioned embodiment, The change in the range which can achieve the objective of this invention, improvement, etc. are included in this invention.

The light emitting layer is not limited to one layer, and a plurality of light emitting layers may be stacked. When the organic EL element has a plurality of light-emitting layers, it is sufficient that at least one light-emitting layer contains the first material, the second material, and the third material, and the other light-emitting layers emit fluorescent light. Even a layer may be a phosphorescent light-emitting layer that utilizes light emission by electron transition from a triplet excited state to a direct ground state.
In addition, when the organic EL element has a plurality of light emitting layers, these light emitting layers may be provided adjacent to each other, or a so-called tandem organic material in which a plurality of light emitting units are stacked via an intermediate layer. It may be an EL element.

Further, for example, a barrier layer may be provided adjacent to the anode side or the cathode side of the light emitting layer. The barrier layer is preferably disposed in contact with the light emitting layer and blocks at least one of holes, electrons, excitons, and exciplexes.
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 the holes reach a layer (for example, an electron transport layer) on the cathode side of the barrier layer. Stop that.
In addition, when a barrier layer is arranged in contact with the anode side of the light emitting layer, the barrier layer transports holes, and the electrons reach a layer on the anode side of the barrier layer (for example, a hole transport layer). To stop doing.
Further, a barrier layer may be provided adjacent to the light emitting layer so that excitation energy does not leak from the light emitting layer to the peripheral layer. The excitons generated in the light emitting layer are prevented from moving to a layer (for example, an electron transport layer or a hole transport layer) closer to the electrode than the barrier layer.
The light emitting layer and the barrier layer are preferably joined.

  An organic EL element according to an embodiment of the present invention is a display component such as an organic EL panel module, a display device such as a television, a mobile phone, a tablet or a personal computer, and an electronic device such as a light emitting device for lighting or a vehicle lamp. Can be used for

  In addition, the specific structure and shape in the implementation of the present invention may be other structures as long as the object of the present invention can be achieved.

  Hereinafter, examples according to the present invention will be described, but the present invention is not limited to these examples.

  The compounds used in this example are as follows.

<Evaluation of compound>
Next, the physical properties of the compounds used in this example were measured. The measurement method and calculation method are shown below, and the measurement results and calculation results are shown in Table 5.

・ Singlet energy EgS
Singlet energy EgS is measured as follows.
A 10 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell, and the absorption spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample was measured at room temperature (300 K). A single line energy was calculated by drawing a tangent line to the long wavelength falling edge of the absorption spectrum and substituting the wavelength value λ _edge [nm] at the intersection of the tangent line and the horizontal axis into the following conversion formula 3. .
Conversion formula 3: EgS [eV] = 1239.85 / λ _edge
In this example, the absorption spectrum was measured with a spectrophotometer manufactured by Hitachi (device name: U3310).

In addition, the tangent with respect to the fall of the long wavelength side of an absorption spectrum was drawn as follows. When moving on 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, tangents at each point on the curve are considered. This tangent repeats as the curve falls (ie, as the value on the vertical axis decreases), the slope decreases and then increases. The tangent drawn at the point where the slope value takes the minimum value on the long wavelength side (except when the absorbance is 0.1 or less) is taken as the tangent to the fall on the long wavelength side of the absorption spectrum.
In addition, the maximum point whose absorbance value is 0.2 or less was not included in the maximum value on the longest wavelength side.

・ Energy gap Eg at 77 [K] _77K
Regarding the first material and the third material to be measured, the triplet energy was measured as follows. Here, Compound MT-1 and Compound MT-3 were measured. A compound to be measured is dissolved in EPA (diethyl ether: isopentane: ethanol = 5: 5: 2 (volume ratio)) so as to have a concentration of 10 μmol / L, and this solution is placed in a quartz cell and measured. A sample was used. With respect to this measurement sample, a phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) is measured at a low temperature (77 [K]), and a tangent line is drawn with respect to the rising edge of the phosphorescence spectrum on the short wavelength side. Based on the wavelength value λ _edge [nm] at the intersection of the tangent and the horizontal axis, the energy amount calculated from the following conversion formula 1 was defined as an energy gap Eg _77K at 77 [K].
Conversion formula 1: Eg _77K [eV] = 1239.85 / λ _edge
Regarding the second material to be measured, the triplet energy was measured as follows. Here, compound MT-2 was used as a measurement target. A sample (second material) to be measured and the compound TH-2 were co-deposited on a quartz substrate, and a sample sealed in an NMR tube was produced. This sample was prepared under the following conditions.
Quartz substrate / TH-2: second material (film thickness 100 nm, second material concentration: 12% by mass)
With respect to this measurement sample, a phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) is measured at a low temperature (77 [K]), and a tangent line is drawn with respect to the rising edge of the phosphorescence spectrum on the short wavelength side. Based on the wavelength value λ _edge [nm] at the intersection of the tangent and the horizontal axis, the energy amount calculated from the following conversion formula 2 was defined as an energy gap Eg _77K at 77 [K].
Conversion formula 2: Eg _77K [eV] = 1239.85 / λ _edge
For measurement of phosphorescence, an F-4500 spectrofluorometer main body manufactured by Hitachi High-Technology Co., Ltd. was used.

The tangent to the rising edge on the short wavelength side of the phosphorescence spectrum is drawn as follows. When moving on 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, tangents at each point on the curve are considered toward the long wavelength side. The slope of this tangent line increases as the curve rises (that is, as the vertical axis increases). A tangent drawn at a point where the value of the slope takes a maximum value (that is, a tangent at the inflection point) is a tangent to the rising edge of the phosphorescence spectrum on the short wavelength side.
Note that the maximum point having a peak intensity of 15% or less of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and has the maximum slope value closest to the maximum value on the shortest wavelength side. The tangent drawn at the point where the value was taken was taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side.
For measurement of phosphorescence, an F-4500 spectrofluorometer main body manufactured by Hitachi High-Technology Co., Ltd. was used.

Measurement was performed using a photoelectron spectrometer (Riken Keiki Co., Ltd .: AC-3) under an ionization potential atmosphere. Specifically, the measurement was performed by irradiating the compound to be measured with light and measuring the amount of electrons generated by charge separation.

・ Affinity (electron affinity)
Using the measured values of the ionization potential Ip and singlet energy EgS of the compound measured by the method described above, the calculation was performed from the following formula.
Af = Ip-EgS

-Delayed fluorescence emission Delayed fluorescence emission was confirmed by measuring transient PL using the apparatus shown in FIG. The compound MT-2 and the compound TH-2 were co-evaporated on a quartz substrate so that the ratio of the compound MT-2 was 12% by mass, and a thin film having a thickness of 100 nm was formed to prepare a sample.
Delayed fluorescence can be obtained using the apparatus shown in FIG. Prompt light emission (immediate light emission) immediately observed from the excited state after excitation with pulsed light (light emitted from a pulse laser) of the wavelength absorbed by the compound MT-2, and immediately after the excitation Is not observed, and there is delay light emission (delayed light emission) observed thereafter. Delayed fluorescence emission in this embodiment means that the amount of delay emission (delayed emission) is 5% or more with respect to the amount of Promp emission (immediate emission), and the compound MT-2 has an amount of delay emission (delayed emission). Is 5% or more of the amount of Prompt light emission (immediate light emission).
The amounts of Prompt light emission and Delay light emission can be obtained by the same method as described in “Nature 492, 234-238, 2012”. The apparatus used for calculating the amount of Promp light emission and Delay light emission is not limited to the apparatus shown in FIG.

<Production and Evaluation of Organic EL Element>
An organic EL element was produced and evaluated as follows.

Example 1
A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) having a thickness of 25 mm × 75 mm × 1.1 mm was subjected to ultrasonic cleaning for 5 minutes in isopropyl alcohol, and then UV ozone cleaning was performed for 30 minutes. The film thickness of ITO was 130 nm.
The glass substrate with the transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum deposition apparatus, and first, the compound HI is deposited so as to cover the transparent electrode on the surface where the transparent electrode line is formed, and the film thickness is 5 nm. The hole injection layer was formed.
Next, Compound HT-1 was vapor-deposited on the hole injection layer, and a first hole transport layer having a thickness of 80 nm was formed on the HI film.
Next, Compound HT-2 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a thickness of 15 nm.
Further, on this second hole transport layer, the compound MT-1 as the first material, the compound MT-2 as the second material, and the compound MT-3 as the third material are combined. Evaporation was performed to form a light emitting layer with a thickness of 25 nm. The concentration of compound MT-1 in the light emitting layer was 1% by mass, the concentration of compound MT-2 was 50% by mass, and the concentration of compound MT-3 was 49% by mass.
Next, Compound HB-1 was vapor-deposited on the light emitting layer to form a 5 nm thick barrier layer.
Next, Compound ET-1 was vapor-deposited on the barrier layer to form an electron transport layer having a thickness of 20 nm.
Next, lithium fluoride (LiF) was vapor-deposited on the electron transport layer to form an electron injecting electrode (cathode) having a thickness of 1 nm.
And metal aluminum (Al) was vapor-deposited on this electron injecting electrode, and the metal Al cathode with a film thickness of 80 nm was formed.
A device arrangement of the organic EL device of Example 1 is schematically shown as follows.
ITO (130) / HI (5) / HT-1 (80) / HT-2 (15) / MT-1: MT-2: MT-3 (25, 1%: 50%: 49%) / HB- 1 (5) / ET-1 (20) / LiF (1) / Al (80)
The numbers in parentheses indicate the film thickness (unit: nm). Similarly, in the parentheses, the number displayed as a percentage indicates the ratio (mass%) of each material in the light emitting layer.

(Comparative Example 1)
In the organic EL device of Comparative Example 1, in place of the light emitting layer in Example 1, the compound MT-1 as the first material and the compound MT-2 as the second material were co-evaporated to have a film thickness of 25 nm. This was prepared in the same manner as in Example 1 except that the light emitting layer was formed. In the light emitting layer of the organic EL element of Comparative Example 1, the concentration of the compound MT-1 in the light emitting layer was 1 mass%, and the concentration of the compound MT-2 was 99 mass%.
A device arrangement of the organic EL device of Comparative Example 1 is schematically shown as follows.
ITO (130) / HI (5) / HT-1 (80) / HT-2 (15) / MT-1: MT-2 (25, 1%: 99%) / HB-1 (5) / ET- 1 (20) / LiF (1) / Al (80)

[Evaluation of organic EL elements]
The organic EL elements produced in Example 1 and Comparative Example 1 were evaluated as follows. The evaluation results are shown in Table 6.

Drive voltage The voltage (unit: V) was measured when current was passed between the ITO transparent electrode and the metal Al cathode so that the current density was 0.1 mA / cm ² , 1 mA / cm ² or 10 mA / cm ² . .

Luminance and CIE1931 chromaticity Luminance and CIE1931 chromaticity coordinates (x, y) when a voltage is applied to the device so that the current density is 0.1 mA / cm ² , 1 mA / cm ^2, or 10 mA / cm ² Was measured with a spectral radiance meter CS-1000 (manufactured by Konica Minolta).

・ Current efficiency L / J and power efficiency η
Spectral radiance spectrum when a voltage is applied to the element so that the current density is 0.1 mA / cm ² , 1 mA / cm ² or 10 mA / cm ² is measured with the above spectral radiance meter, and the obtained spectral radiation Current efficiency (unit: cd / A) and power efficiency η (unit: lm / W) were calculated from the luminance spectrum.

・ Main peak wavelength λ _p
The main peak wavelength λ _p was determined from the obtained spectral radiance spectrum.

・ External quantum efficiency EQE
The spectral radiance spectrum when a voltage was applied to the device so that the current density was 0.1 mA / cm ² , 1 mA / cm ^2, or 10 mA / cm ² was measured with the above spectral radiance meter. From the obtained spectral radiance spectrum, the external quantum efficiency EQE (unit:%) was calculated on the assumption that Lambtian radiation was performed.

  As shown in Table 6, when the organic EL element according to Example 1 was driven at any current density, compared with the organic EL element according to Comparative Example 1, the current efficiency L / J, the power efficiency η, and External quantum efficiency EQE became high. In the organic EL device according to Comparative Example 1, it is considered that the light emitting efficiency is low because the light emitting layer contains only the first material and the second material. In the organic EL device according to Example 1, not only the first material and the second material but also the third material was contained in the light emitting layer, so that the luminous efficiency was improved as compared with Comparative Example 1. it is conceivable that. In Example 1, the wavelength was shorter than that in Comparative Example 1, and light emission with strong bluish color was observed. That is, it is considered that it is caused by dispersing the second material. As described above, Example 1 was able to provide an organic EL element that emits blue light with high efficiency.

  Next, other organic EL devices were produced using the compounds used in the Examples and Comparative Examples and the following compounds.

<Evaluation of compound>
Next, physical properties from the compound MT-4 to the compound MT-13 were measured. The measurement method and calculation method are shown below, and the measurement result and calculation result are shown in Table 7. The measurement method and calculation method are the same as those described above. The compound MT-9 and the compound MT-12 were compounds having delayed fluorescence (delayed emission) of 5% or more with respect to the amount of Promp emission (immediate emission) and delayed fluorescence.

(Example 2)
A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) having a thickness of 25 mm × 75 mm × 1.1 mm was subjected to ultrasonic cleaning for 5 minutes in isopropyl alcohol, and then UV ozone cleaning was performed for 30 minutes. The film thickness of ITO was 70 nm.
The glass substrate with the transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum deposition apparatus, and first, the compound HI is deposited so as to cover the transparent electrode on the surface where the transparent electrode line is formed, and the film thickness is 5 nm. The hole injection layer was formed.
Next, Compound HT-1 was vapor-deposited on the hole injection layer, and a first hole transport layer having a thickness of 65 nm was formed on the HI film.
Next, Compound HT-2 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a thickness of 10 nm.
Further, Compound MT-4, Compound MT-9, and Compound MT-10 were co-evaporated on the second hole transport layer to form a light emitting layer having a thickness of 25 nm. The concentration of compound MT-10 in the light emitting layer was 1% by mass, the concentration of compound MT-9 was 50% by mass, and the concentration of compound MT-4 was 49% by mass.
Next, Compound HB-2 was vapor-deposited on the light emitting layer to form a barrier layer having a thickness of 5 nm.
Next, Compound ET-1 was vapor-deposited on the barrier layer to form an electron transport layer having a thickness of 30 nm.
Next, lithium fluoride (LiF) was vapor-deposited on the electron transport layer to form an electron injecting electrode (cathode) having a thickness of 1 nm.
And metal aluminum (Al) was vapor-deposited on this electron injecting electrode, and the metal Al cathode with a film thickness of 80 nm was formed.
A device arrangement of the organic EL device of Example 2 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-4: MT-9: MT-10 (25, 49%: 50%: 1%) / HB- 2 (5) / ET-1 (30) / LiF (1) / Al (80)

Example 3
The organic EL device of Example 3 was produced in the same manner as in Example 2 except that Compound MT-6 was used instead of Compound MT-4 in the light emitting layer of Example 2.
A device arrangement of the organic EL device of Example 3 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-6: MT-9: MT-10 (25, 49%: 50%: 1%) / HB- 2 (5) / ET-1 (30) / LiF (1) / Al (80)

Example 4
The organic EL device of Example 4 was produced in the same manner as Example 2 except that Compound MT-5 was used instead of Compound MT-4 in the light emitting layer of Example 2.
A device arrangement of the organic EL device of Example 4 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-5: MT-9: MT-10 (25, 49%: 50%: 1%) / HB- 2 (5) / ET-1 (30) / LiF (1) / Al (80)

(Example 5)
The organic EL device of Example 5 was produced in the same manner as Example 2 except that Compound MT-7 was used instead of Compound MT-4 in the light emitting layer of Example 2.
A device arrangement of the organic EL device of Example 5 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-7: MT-9: MT-10 (25, 49%: 50%: 1%) / HB- 2 (5) / ET-1 (30) / LiF (1) / Al (80)

(Example 6)
The organic EL device of Example 6 was produced in the same manner as Example 2 except that Compound MT-8 was used instead of Compound MT-4 in the light emitting layer of Example 2.
A device arrangement of the organic EL device of Example 6 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-8: MT-9: MT-10 (25, 49%: 50%: 1%) / HB- 2 (5) / ET-1 (30) / LiF (1) / Al (80)

(Comparative Example 2)
The organic EL device of Comparative Example 2 was replaced with the light emitting layer in Example 2, except that compound MT-9 and compound MT-10 were co-evaporated to form a light emitting layer having a thickness of 25 nm. This was prepared in the same manner as in No. 2. In the light emitting layer of the organic EL element of Comparative Example 2, the concentration of the compound MT-10 in the light emitting layer was 1% by mass, and the concentration of the compound MT-9 was 99% by mass.
A device arrangement of the organic EL device of Comparative Example 2 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-9: MT-10 (25, 99%: 1%) / HB-2 (5) / ET- 1 (30) / LiF (1) / Al (80)

[Evaluation of organic EL elements]
The organic EL elements produced in Examples 2 to 6 and Comparative Example 2 were evaluated in the same manner as described above. The evaluation items were drive voltage, luminance, CIE 1931 chromaticity, current efficiency L / J, power efficiency η, main peak wavelength λ _p , and external quantum efficiency EQE. The evaluation results are shown in Table 8.

  As shown in Table 8, the organic EL elements of Examples 2 to 6 had higher luminous efficiency than the organic EL element of Comparative Example 2. The organic EL device of Comparative Example 2 only includes compound MT-9 and compound MT-10 in the light emitting layer. Compared to the organic EL element of Comparative Example 2, the organic EL elements of Examples 2 to 6 further contained a third material in the light emitting layer. Specifically, compound MT-4 in Example 2, compound MT-6 in Example 3, compound MT-5 in Example 4, compound MT-7 in Example 5, compound MT-7 in Example 6 MT-8 was contained in the light emitting layer as a third material. As a result, the organic EL elements of Examples 2 to 6 had higher current efficiency and external quantum efficiency than the organic EL elements of Comparative Example 2.

(Example 7)
The organic EL device of Example 7 was produced in the same manner as Example 2 except that Compound HB-3 was used instead of Compound HB-2 in the barrier layer of Example 2.
A device arrangement of the organic EL device of Example 7 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-4: MT-9: MT-10 (25, 49%: 50%: 1%) / HB- 3 (5) / ET-1 (30) / LiF (1) / Al (80)

(Example 8)
The organic EL device of Example 8 was produced in the same manner as Example 7 except that Compound MT-6 was used instead of Compound MT-4 in the light emitting layer of Example 7.
A device arrangement of the organic EL device of Example 8 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-6: MT-9: MT-10 (25, 49%: 50%: 1%) / HB- 3 (5) / ET-1 (30) / LiF (1) / Al (80)

Example 9
The organic EL device of Example 9 was produced in the same manner as in Example 7, except that Compound MT-5 was used instead of Compound MT-4 in the light emitting layer of Example 7.
A device arrangement of the organic EL device of Example 9 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-5: MT-9: MT-10 (25, 49%: 50%: 1%) / HB- 3 (5) / ET-1 (30) / LiF (1) / Al (80)

(Example 10)
The organic EL device of Example 10 was produced in the same manner as in Example 7 except that Compound MT-7 was used instead of Compound MT-4 in the light emitting layer of Example 7.
A device arrangement of the organic EL device of Example 10 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-7: MT-9: MT-10 (25, 49%: 50%: 1%) / HB- 3 (5) / ET-1 (30) / LiF (1) / Al (80)

(Example 11)
The organic EL device of Example 11 was produced in the same manner as in Example 7 except that Compound MT-8 was used instead of Compound MT-4 in the light emitting layer of Example 7.
A device arrangement of the organic EL device of Example 11 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-8: MT-9: MT-10 (25, 49%: 50%: 1%) / HB- 3 (5) / ET-1 (30) / LiF (1) / Al (80)

(Comparative Example 3)
The organic EL device of Comparative Example 3 was replaced with the light emitting layer in Example 7, except that compound MT-9 and compound MT-10 were co-evaporated to form a light emitting layer with a thickness of 25 nm. This was prepared in the same manner as in Example 7. In the light emitting layer of the organic EL element of Comparative Example 3, the concentration of the compound MT-10 in the light emitting layer was 1% by mass, and the concentration of the compound MT-9 was 99% by mass.
A device arrangement of the organic EL device of Comparative Example 3 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-9: MT-10 (25, 99%: 1%) / HB-3 (5) / ET- 1 (30) / LiF (1) / Al (80)

[Evaluation of organic EL elements]
The organic EL elements produced in Examples 7 to 11 and Comparative Example 3 were evaluated in the same manner as described above. The evaluation items were drive voltage, luminance, CIE 1931 chromaticity, current efficiency L / J, power efficiency η, main peak wavelength λ _p , and external quantum efficiency EQE. Table 9 shows the evaluation results.

  As shown in Table 9, the organic EL elements of Examples 7 to 11 had higher luminous efficiency than the organic EL element of Comparative Example 3. The organic EL device of Comparative Example 3 only includes compound MT-9 and compound MT-10 in the light emitting layer. Compared with the organic EL element of Comparative Example 3, the organic EL elements of Examples 7 to 11 further contained a third material in the light emitting layer. Specifically, compound MT-4 in Example 7, compound MT-6 in Example 8, compound MT-5 in Example 9, compound MT-7 in Example 10, compound MT-7 in Example 11 MT-8 was contained in the light emitting layer as a third material. As a result, the organic EL elements of Examples 7 to 11 had higher current efficiency and external quantum efficiency than the organic EL elements of Comparative Example 3.

(Example 12)
The organic EL device of Example 12 was produced in the same manner as Example 2 except that Compound MT-11 was used instead of Compound MT-10 in the light emitting layer of Example 2.
A device arrangement of the organic EL device of Example 12 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-4: MT-9: MT-11 (25, 49%: 50%: 1%) / HB- 2 (5) / ET-1 (30) / LiF (1) / Al (80)

(Example 13)
The organic EL device of Example 13 was produced in the same manner as in Example 12 except that Compound MT-6 was used instead of Compound MT-4 in the light emitting layer of Example 12.
A device arrangement of the organic EL device of Example 13 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-6: MT-9: MT-11 (25, 49%: 50%: 1%) / HB- 2 (5) / ET-1 (30) / LiF (1) / Al (80)

(Example 14)
The organic EL device of Example 14 was produced in the same manner as in Example 12 except that Compound MT-7 was used instead of Compound MT-4 in the light emitting layer of Example 12.
A device arrangement of the organic EL device of Example 14 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-7: MT-9: MT-11 (25, 49%: 50%: 1%) / HB- 2 (5) / ET-1 (30) / LiF (1) / Al (80)

(Example 15)
The organic EL device of Example 15 was produced in the same manner as in Example 12 except that Compound MT-8 was used instead of Compound MT-4 in the light emitting layer of Example 12.
A device arrangement of the organic EL device of Example 15 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-8: MT-9: MT-11 (25, 49%: 50%: 1%) / HB- 2 (5) / ET-1 (30) / LiF (1) / Al (80)

(Comparative Example 4)
The organic EL device of Comparative Example 4 was replaced with the light emitting layer in Example 12, except that Compound MT-9 and Compound MT-11 were co-evaporated to form a light emitting layer having a thickness of 25 nm. This was prepared in the same manner as in No. 12. In the light emitting layer of the organic EL element of Comparative Example 4, the concentration of the compound MT-11 in the light emitting layer was 1% by mass, and the concentration of the compound MT-9 was 99% by mass.
A device arrangement of the organic EL device of Comparative Example 4 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-9: MT-11 (25, 99%: 1%) / HB-2 (5) / ET- 1 (30) / LiF (1) / Al (80)

[Evaluation of organic EL elements]
The organic EL elements produced in Examples 12 to 15 and Comparative Example 4 were evaluated in the same manner as described above. The evaluation items were drive voltage, luminance, CIE 1931 chromaticity, current efficiency L / J, power efficiency η, main peak wavelength λ _p , and external quantum efficiency EQE. Table 10 shows the evaluation results.

  As shown in Table 10, the organic EL elements of Examples 12 to 15 had higher luminous efficiency than the organic EL element of Comparative Example 4. The organic EL device of Comparative Example 4 only includes compound MT-9 and compound MT-11 in the light emitting layer. Compared to the organic EL element of Comparative Example 4, the organic EL elements of Examples 12 to 15 further contained a third material in the light emitting layer. Specifically, the compound MT-4 in Example 12, the compound MT-6 in Example 13, the compound MT-7 in Example 14, the compound MT-8 in Example 15, and the third material, respectively. In the light emitting layer. As a result, the organic EL elements of Examples 12 to 15 had higher current efficiency and external quantum efficiency than the organic EL elements of Comparative Example 4.

(Example 16)
The organic EL device of Example 16 was produced in the same manner as in Example 12 except that Compound HB-3 was used instead of Compound HB-2 in the barrier layer of Example 12.
A device arrangement of the organic EL device of Example 16 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-4: MT-9: MT-11 (25, 49%: 50%: 1%) / HB- 3 (5) / ET-1 (30) / LiF (1) / Al (80)

(Example 17)
The organic EL device of Example 17 was produced in the same manner as in Example 16 except that Compound MT-6 was used instead of Compound MT-4 in the light emitting layer of Example 16.
A device arrangement of the organic EL device of Example 17 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-6: MT-9: MT-11 (25, 49%: 50%: 1%) / HB- 3 (5) / ET-1 (30) / LiF (1) / Al (80)

(Example 18)
The organic EL device of Example 18 was produced in the same manner as in Example 16 except that Compound MT-7 was used instead of Compound MT-4 in the light emitting layer of Example 16.
A device arrangement of the organic EL device of Example 18 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-7: MT-9: MT-11 (25, 49%: 50%: 1%) / HB- 3 (5) / ET-1 (30) / LiF (1) / Al (80)

(Example 19)
The organic EL device of Example 19 was produced in the same manner as in Example 16 except that Compound MT-8 was used instead of Compound MT-4 in the light emitting layer of Example 16.
A device arrangement of the organic EL device of Example 19 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-8: MT-9: MT-11 (25, 49%: 50%: 1%) / HB- 3 (5) / ET-1 (30) / LiF (1) / Al (80)

(Comparative Example 5)
The organic EL device of Comparative Example 5 was replaced with the light emitting layer in Example 16, except that compound MT-9 and compound MT-11 were co-evaporated to form a light emitting layer having a thickness of 25 nm. 16 was produced in the same manner. In the light emitting layer of the organic EL element of Comparative Example 5, the concentration of compound MT-11 in the light emitting layer was 1% by mass, and the concentration of compound MT-9 was 99% by mass.
A device arrangement of the organic EL device of Comparative Example 5 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-9: MT-11 (25, 99%: 1%) / HB-3 (5) / ET- 1 (30) / LiF (1) / Al (80)

[Evaluation of organic EL elements]
The organic EL elements produced in Examples 16 to 19 and Comparative Example 5 were evaluated in the same manner as described above. The evaluation items were drive voltage, luminance, CIE 1931 chromaticity, current efficiency L / J, power efficiency η, main peak wavelength λ _p , and external quantum efficiency EQE. The evaluation results are shown in Table 11.

  As shown in Table 11, the organic EL elements of Examples 16 to 19 had higher luminous efficiency than the organic EL element of Comparative Example 5. The organic EL device of Comparative Example 5 only includes compound MT-9 and compound MT-11 in the light emitting layer. Compared to the organic EL element of Comparative Example 5, the organic EL elements of Examples 16 to 19 further contained a third material in the light emitting layer. Specifically, the compound MT-4 in Example 16, the compound MT-6 in Example 17, the compound MT-7 in Example 18, the compound MT-8 in Example 19, and the third material, respectively. In the light emitting layer. As a result, the organic EL elements of Examples 16 to 19 had higher current efficiency and external quantum efficiency than the organic EL element of Comparative Example 5.

(Example 20)
A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) having a thickness of 25 mm × 75 mm × 1.1 mm was subjected to ultrasonic cleaning for 5 minutes in isopropyl alcohol, and then UV ozone cleaning was performed for 30 minutes. The film thickness of ITO was 70 nm.
The glass substrate with the transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum deposition apparatus, and first, the compound HI is deposited so as to cover the transparent electrode on the surface where the transparent electrode line is formed, and the film thickness is 5 nm. The hole injection layer was formed.
Next, Compound HT-1 was vapor-deposited on the hole injection layer, and a first hole transport layer having a thickness of 65 nm was formed on the HI film.
Next, Compound HT-2 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a thickness of 5 nm.
Further, a compound CBP was vapor-deposited on the second hole transport layer to form a first barrier layer having a thickness of 5 nm.
Next, Compound MT-13, Compound MT-12, and Compound MT-10 were co-evaporated on the first barrier layer to form a light emitting layer having a thickness of 25 nm. The concentration of compound MT-10 in the light emitting layer was 1% by mass, the concentration of compound MT-12 was 50% by mass, and the concentration of compound MT-13 was 49% by mass.
Next, the compound HB-2 was vapor-deposited on this light emitting layer, and the 5 nm-thick 2nd barrier layer was formed.
Next, Compound ET-1 was vapor-deposited on this second barrier layer to form an electron transport layer having a thickness of 30 nm.
Next, lithium fluoride (LiF) was vapor-deposited on the electron transport layer to form an electron injecting electrode (cathode) having a thickness of 1 nm.
And metal aluminum (Al) was vapor-deposited on this electron injecting electrode, and the metal Al cathode with a film thickness of 80 nm was formed.
A device arrangement of the organic EL device of Example 20 is roughly shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (5) / CBP (5) / MT-13: MT-12: MT-10 (25, 49%: 50%: 1 %) / HB-2 (5) / ET-1 (30) / LiF (1) / Al (80)

(Example 21)
In the organic EL device of Example 21, the concentration of the compound contained in the light emitting layer of Example 20 was 1% by mass of Compound MT-10, 25% by mass of Compound MT-12, and of Compound MT-13. It was produced in the same manner as in Example 20 except that the concentration was 74% by mass.
A device arrangement of the organic EL device of Example 21 is roughly shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (5) / CBP (5) / MT-13: MT-12: MT-10 (25, 74%: 25%: 1 %) / HB-2 (5) / ET-1 (30) / LiF (1) / Al (80)

(Example 22)
In the organic EL device of Example 22, the compound MT-5 was used instead of the compound MT-13 in the light emitting layer of Example 20, and the concentration of the compound MT-10 was 1% by mass with respect to the concentration of the compound contained in the light emitting layer. This was prepared in the same manner as in Example 20 except that the concentration of compound MT-12 was 24 mass% and the concentration of compound MT-5 was 75 mass%.
A device arrangement of the organic EL device of Example 22 is roughly shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (5) / CBP (5) / MT-5: MT-12: MT-10 (25, 75%: 24%: 1 %) / HB-2 (5) / ET-1 (30) / LiF (1) / Al (80)

(Comparative Example 6)
The organic EL device of Comparative Example 6 was replaced with the light-emitting layer in Example 20, except that Compound MT-12 and Compound MT-10 were co-evaporated to form a light-emitting layer with a thickness of 25 nm. 20 was prepared in the same manner as in No. 20. In the light emitting layer of the organic EL element of Comparative Example 6, the concentration of the compound MT-10 in the light emitting layer was 1% by mass, and the concentration of the compound MT-12 was 99% by mass.
A device arrangement of the organic EL device of Comparative Example 6 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (5) / CBP (5) / MT-12: MT-10 (25, 99%: 1%) / HB-2 ( 5) / ET-1 (30) / LiF (1) / Al (80)

[Evaluation of organic EL elements]
The organic EL elements produced in Examples 20 to 22 and Comparative Example 6 were evaluated in the same manner as described above. The evaluation items were drive voltage, luminance, CIE 1931 chromaticity, current efficiency L / J, power efficiency η, main peak wavelength λ _p , and external quantum efficiency EQE. The evaluation results are shown in Table 12.

  As shown in Table 12, the organic EL elements of Examples 20 to 22 had higher luminous efficiency than the organic EL element of Comparative Example 6. The organic EL device of Comparative Example 6 only includes compound MT-10 and compound MT-12 in the light emitting layer. Compared to the organic EL element of Comparative Example 6, the organic EL elements of Examples 20 to 22 further contained a third material in the light emitting layer. Specifically, Example 20 and 21 contained Compound MT-13 in Example 22, and Compound MT-5 in Example 22 as a third material, respectively. As a result, the organic EL elements of Examples 20 to 22 had higher current efficiency, power efficiency, and external quantum efficiency than the organic EL elements of Comparative Example 6.

(Example 23)
The organic EL device of Example 23 was produced in the same manner as in Example 20 except that Compound HB-3 was used instead of Compound HB-2 in the barrier layer of Example 20.
A device arrangement of the organic EL device of Example 23 is roughly shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (5) / CBP (5) / MT-13: MT-12: MT-10 (25, 49%: 50%: 1 %) / HB-3 (5) / ET-1 (30) / LiF (1) / Al (80)

(Example 24)
In the organic EL device of Example 24, regarding the concentration of the compound contained in the light emitting layer of Example 23, the concentration of Compound MT-10 was 1% by mass, the concentration of Compound MT-12 was 25% by mass, and the concentration of Compound MT-13 was It was produced in the same manner as in Example 23 except that the concentration was 74% by mass.
A device arrangement of the organic EL device of Example 24 is roughly shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (5) / CBP (5) / MT-13: MT-12: MT-10 (25, 74%: 25%: 1 %) / HB-3 (5) / ET-1 (30) / LiF (1) / Al (80)

(Example 25)
The organic EL device of Example 25 uses Compound MT-5 instead of Compound MT-13 in the light emitting layer of Example 23, and the concentration of Compound MT-10 is 1% by mass with respect to the concentration of the compound contained in the light emitting layer. This was prepared in the same manner as in Example 23 except that the concentration of compound MT-12 was 24 mass% and the concentration of compound MT-5 was 75 mass%.
A device arrangement of the organic EL device of Example 25 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (5) / CBP (5) / MT-5: MT-12: MT-10 (25, 75%: 24%: 1 %) / HB-3 (5) / ET-1 (30) / LiF (1) / Al (80)

(Comparative Example 7)
The organic EL device of Comparative Example 7 was replaced with the light-emitting layer in Example 23, except that compound MT-12 and compound MT-10 were co-evaporated to form a light-emitting layer with a thickness of 25 nm. This was prepared in the same manner as in No.23. In the light emitting layer of the organic EL element of Comparative Example 7, the concentration of the compound MT-10 in the light emitting layer was 1% by mass, and the concentration of the compound MT-12 was 99% by mass.
A device arrangement of the organic EL device of Comparative Example 7 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (5) / CBP (5) / MT-12: MT-10 (25, 99%: 1%) / HB-3 ( 5) / ET-1 (30) / LiF (1) / Al (80)

[Evaluation of organic EL elements]
The organic EL elements produced in Examples 23 to 25 and Comparative Example 7 were evaluated in the same manner as described above. The evaluation items were drive voltage, luminance, CIE 1931 chromaticity, current efficiency L / J, power efficiency η, main peak wavelength λ _p , and external quantum efficiency EQE. The evaluation results are shown in Table 13.

  As shown in Table 13, the organic EL elements of Examples 23 to 25 had higher luminous efficiency than the organic EL element of Comparative Example 7. The organic EL device of Comparative Example 7 only includes compound MT-10 and compound MT-12 in the light emitting layer. Compared to the organic EL element of Comparative Example 7, the organic EL elements of Examples 23 to 25 further contained a third material in the light emitting layer. Specifically, in Example 23 and 24, Compound MT-13 was contained in the light emitting layer as a third material, and in Example 25, Compound MT-5 was contained in the light emitting layer. As a result, the organic EL elements of Examples 23 to 25 had higher current efficiency, power efficiency, and external quantum efficiency than the organic EL elements of Comparative Example 7.

(Example 26)
The organic EL device of Example 26 uses Compound MT-11 instead of Compound MT-10 in the light emitting layer of Example 20, and the concentration of Compound MT-11 is 1% by mass with respect to the concentration of the compound contained in the light emitting layer. This was prepared in the same manner as in Example 20 except that the concentration of compound MT-12 was 25 mass% and the concentration of compound MT-13 was 74 mass%.
A device arrangement of the organic EL device of Example 26 is roughly shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (5) / CBP (5) / MT-13: MT-12: MT-11 (25, 74%: 25%: 1 %) / HB-2 (5) / ET-1 (30) / LiF (1) / Al (80)

(Comparative Example 8)
The organic EL device of Comparative Example 8 was replaced with the light emitting layer in Example 26, except that compound MT-12 and compound MT-11 were co-evaporated to form a light emitting layer having a thickness of 25 nm. 26. In the light emitting layer of the organic EL element of Comparative Example 8, the concentration of the compound MT-11 in the light emitting layer was 1 mass%, and the concentration of the compound MT-12 was 99 mass%.
A device arrangement of the organic EL device of Comparative Example 8 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (5) / CBP (5) / MT-12: MT-11 (25, 99%: 1%) / HB-2 ( 5) / ET-1 (30) / LiF (1) / Al (80)

[Evaluation of organic EL elements]
The organic EL elements produced in Example 26 and Comparative Example 8 were evaluated in the same manner as described above. The evaluation items were drive voltage, luminance, CIE 1931 chromaticity, current efficiency L / J, power efficiency η, main peak wavelength λ _p , and external quantum efficiency EQE. The evaluation results are shown in Table 14.

  As shown in Table 14, the organic EL element of Example 26 had higher luminous efficiency than the organic EL element of Comparative Example 8. The organic EL device of Comparative Example 8 only includes compound MT-11 and compound MT-12 in the light emitting layer. Compared to the organic EL element of Comparative Example 8, the organic EL element of Example 26 further contained compound MT-13 in the light emitting layer. As a result, the organic EL element of Example 26 had higher current efficiency, power efficiency, and external quantum efficiency than the organic EL element of Comparative Example 8.

(Example 27)
The organic EL device of Example 27 was produced in the same manner as in Example 26 except that Compound HB-3 was used instead of Compound HB-2 in the barrier layer of Example 26.
A device arrangement of the organic EL device of Example 27 is roughly shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (5) / CBP (5) / MT-13: MT-12: MT-11 (25, 74%: 25%: 1 %) / HB-3 (5) / ET-1 (30) / LiF (1) / Al (80)

(Comparative Example 9)
The organic EL device of Comparative Example 9 was replaced with the light emitting layer in Example 27, except that compound MT-12 and compound MT-11 were co-evaporated to form a light emitting layer having a thickness of 25 nm. This was prepared in the same manner as in No.27. In the light emitting layer of the organic EL element of Comparative Example 9, the concentration of the compound MT-11 in the light emitting layer was 1 mass%, and the concentration of the compound MT-12 was 99 mass%.
A device arrangement of the organic EL device of Comparative Example 9 is schematically shown as follows.
ITO (70) / HI (5) / HT-1 (65) / HT-2 (5) / CBP (5) / MT-12: MT-11 (25, 99%: 1%) / HB-3 ( 5) / ET-1 (30) / LiF (1) / Al (80)

[Evaluation of organic EL elements]
The organic EL elements produced in Example 27 and Comparative Example 9 were evaluated in the same manner as described above. The evaluation items were drive voltage, luminance, CIE 1931 chromaticity, current efficiency L / J, power efficiency η, main peak wavelength λ _p , and external quantum efficiency EQE. The evaluation results are shown in Table 15.

  As shown in Table 15, the organic EL element of Example 27 had higher luminous efficiency than the organic EL element of Comparative Example 9. The organic EL device of Comparative Example 9 only includes compound MT-11 and compound MT-12 in the light emitting layer. Compared to the organic EL element of Comparative Example 9, the organic EL element of Example 27 further contained compound MT-13 in the light emitting layer. As a result, the organic EL device of Example 27 had higher current efficiency, power efficiency, and external quantum efficiency than the organic EL device of Comparative Example 9.

DESCRIPTION OF SYMBOLS 1 ... Organic EL element 2 ... Substrate 3 ... Anode 4 ... Cathode 5 ... Light emitting layer 6 ... Hole injection / transport layer 7 ... Electron injection / transport layer 10 ... Organic layer

The organic electroluminescence device according to one embodiment of the present invention includes an anode, a light emitting layer, and a cathode, and the light emitting layer includes a first material, a second material, and a third material, provided that The light emitting layer is not a layer containing the following compound A, the following compound B, and the following compound C. The second material is a delayed fluorescent material, and the singlet energy of the third material. Is larger than the singlet energy of the second material, the first material is a fluorescent light-emitting material, and the first material is represented by the following general formulas (101) to (105). A compound selected from the group consisting of: In the following general formulas (101) to (105), A _D and A _{D1 to} A _D4 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 12 to 50 ring carbon atoms, and A _D , When A _{D1 to} A _D4 have a substituent, the substituent is an alkyl group having 1 to 50 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a ring forming carbon number of 3 to 50. A cycloalkyl group, an aromatic hydrocarbon group having 6 to 50 ring carbon atoms, an aralkyl group having 1 to 50 carbon atoms having an aromatic hydrocarbon group having 6 to 50 ring carbon atoms, and an alkyl having 1 to 50 carbon atoms Group having an alkoxy group, an aryloxy group having an aromatic hydrocarbon group having 6 to 50 ring carbon atoms, an alkylthio group having an alkyl group having 1 to 50 carbon atoms, and an aromatic hydrocarbon having 6 to 50 ring carbon atoms Ally with group A mono-substituted silyl group, a di-substituted silyl group or a tri-substituted silyl group having a group selected from a ruthio group, an alkyl group having 1 to 50 carbon atoms, and an aromatic hydrocarbon group having 6 to 50 ring carbon atoms, a ring atom number of 5 It is selected from the group consisting of a heterocyclic group having 1 to 5 heteroatoms, a haloalkyl group having 1 to 50 carbon atoms, a halogen atom, a cyano group, and a nitro group.
Moreover, the organic electroluminescence element according to one embodiment of the present invention includes an anode, a light emitting layer, and a cathode, and the light emitting layer includes a first material, a second material, and a third material, However, the light emitting layer is not a layer containing the following compound A, the following compound B, and the following compound C, and the second material is a delayed fluorescent material, and is a single layer of the third material. The term energy is larger than the singlet energy of the second material, and the energy gap Eg _77K (M2) at 77 [K] of the second material is the energy gap at 77 [K] of the first material. The energy gap Eg _77K (M3) at 77 [K] of the third material is larger than Eg _77K (M1), and the energy gap Eg at 77 [K] of the second material is The first material is a fluorescent material that is larger than _77K (M2), and the first material is selected from the group consisting of compounds represented by the following general formulas (101) to (105). The selected compound.
Moreover, the organic electroluminescence element according to one embodiment of the present invention includes an anode, a light emitting layer, and a cathode, and the light emitting layer includes a first material, a second material, and a third material, However, the light emitting layer is not a layer containing the following compound A, the following compound B, and the following compound C, and the second material is a delayed fluorescent material, and is a single layer of the third material. The term energy is larger than the singlet energy of the second material, the first material is a fluorescent material, and the first material is an aryl-substituted naphthalene derivative or an aryl-group-substituted anthracene derivative. , Aryl-substituted pyrene derivatives, aryl-substituted chrysene derivatives, aryl-substituted fluoranthene derivatives, indenoperylene derivatives, acenaphthofluoranthene derivatives, pyromethene boron complex Compound, compound or metal complex having a pyrromethene skeleton, diketopyrrolopyrrole derivative is selected from perylene derivatives, and the group consisting of naphthacene derivatives.
Moreover, the organic electroluminescence element according to one embodiment of the present invention includes an anode, a light emitting layer, and a cathode, and the light emitting layer includes a first material, a second material, and a third material, However, the light emitting layer is not a layer containing the following compound A, the following compound B, and the following compound C, and the second material is a delayed fluorescent material, and is a single layer of the third material. The term energy is larger than the singlet energy of the second material, and the energy gap Eg _77K (M2) at 77 [K] of the second material is the energy gap at 77 [K] of the first material. The energy gap Eg _77K (M3) at 77 [K] of the third material is larger than Eg _77K (M1), and the energy gap Eg at 77 [K] of the second material is Larger than _77K (M2), the first material is a fluorescent material, and the first material is an aryl-substituted naphthalene derivative, an aryl-substituted anthracene derivative, an aryl-substituted pyrene derivative, an aryl-substituted Group consisting of chrysene derivatives, aryl-substituted fluoranthene derivatives, indenoperylene derivatives, acenaphthofluoranthene derivatives, pyromethene boron complex compounds, compounds having a pyromethene skeleton or metal complexes thereof, diketopyrrolopyrrole derivatives, perylene derivatives, and naphthacene derivatives Selected from.
An electronic device according to one embodiment of the present invention includes the organic electroluminescence element according to one embodiment of the present invention described above.

In this embodiment, the third material preferably has an electron affinity Af (M3) of 2.8 eV or more. When the third material has such an electron affinity Af (M3), it is possible to make the third material hardly participate in exciton generation or carrier transport in the light emitting layer.

Claims (34)

The anode,
A light emitting layer;
A cathode, and
The light emitting layer includes a first material, a second material, and a third material,
The first material is a fluorescent light-emitting material,
The second material is a delayed fluorescent material,
The singlet energy of the third material is greater than the singlet energy of the second material,
The energy gap Eg _77K (M2) at 77 [K] of the second material is larger than the energy gap Eg _77K (M1) at 77 [K] of the first material,
The energy gap Eg _77K (M3) at 77 [K] of the third material is larger than the energy gap Eg _77K (M2) at 77 [K] of the second material,
However, the said light emitting layer is an organic electroluminescent element which is not a layer containing the following compound A, the following compound B, and the following compound C.
The organic electroluminescent device according to claim 1,
The organic electroluminescence device wherein the singlet energy EgS (M2) of the second material is larger than the singlet energy EgS (M1) of the first material. In the organic electroluminescent element according to claim 1 or 2,
The difference ΔST (M2) between the singlet energy EgS (M2) of the second material and the energy gap Eg _77K (M2) at 77 [K] of the second material is expressed by the following equation (Equation 1). An organic electroluminescence device that meets the requirements.
ΔST (M2) = EgS (M2) −Eg _77K (M2) <0.3 [eV] (Equation 1) In the organic electroluminescent element according to any one of claims 1 to 3,
The difference ΔST (M1) between the singlet energy EgS (M1) of the first material and the energy gap Eg _77K (M1) at 77 [K] of the first material is expressed by the following equation (Equation 2). An organic electroluminescence device that meets the requirements.
ΔST (M1) = EgS (M1) −Eg _77K (M1)> 0.3 [eV] (Equation 2) In the organic electroluminescent element according to any one of claims 1 to 4,
The difference ΔST (M3) between the singlet energy EgS (M3) of the third material and the energy gap Eg _77K (M3) at 77 [K] of the third material is expressed by the following equation (Equation 3). An organic electroluminescence device that meets the requirements.
ΔST (M3) = EgS (M3) −Eg _77K (M3)> 0.3 [eV] (Equation 3) In the organic electroluminescent element according to any one of claims 1 to 5,
An organic electroluminescence device in which the ionization potential Ip (M3) of the third material and the ionization potential Ip (M2) of the second material satisfy the relationship of the following mathematical formula (Formula 4).
Ip (M3) ≧ Ip (M2) (Equation 4) In the organic electroluminescent element according to any one of claims 1 to 6,
The organic electroluminescent element whose energy gap _Eg77K (M3) in 77 [K] of said 3rd material is 2.9 eV or more. In the organic electroluminescent element according to any one of claims 1 to 7,
The organic electroluminescence device having an ionization potential Ip (M3) of the third material of 6.3 eV or more. In the organic electroluminescent element according to any one of claims 1 to 8,
The organic electroluminescence device having an electron affinity Af (M3) of the third material of 2.8 eV or more. In the organic electroluminescent element according to any one of claims 1 to 9,
The organic electroluminescence device, wherein the third material is an aromatic hydrocarbon compound or an aromatic heterocyclic compound. In the organic electroluminescent element according to any one of claims 1 to 10,
The third material is an organic electroluminescence device including, in one molecule, at least one of a partial structure represented by the following general formula (31) and a partial structure represented by the following general formula (32).

(In the general formula _{(31), X} 31 ~X ₃₆ are independently a carbon atom bonded with other atoms on the nitrogen atom or the molecule of the third material, with the _{proviso, X} 31 to X _At least one of ₃₆ is a carbon atom bonded to another atom in the molecule of the third material;
In the general formula (32), Y _{31 to} Y ₃₈ are each independently a nitrogen atom or a carbon atom bonded to another atom in the molecule of the third material, provided that Y _{31 to} Y _38. At least one of them is a carbon atom bonded to another atom in the molecule of the third material, and Y ₃₉ is a nitrogen atom, an oxygen atom, or a sulfur atom. ) The organic electroluminescence device according to claim 11,
The partial structure represented by the general formula (31) is an organic electro- gen contained in the third material as at least one group selected from the group consisting of the following general formula (33) and the following general formula (34). Luminescence element.

(In the general formula (33) and the general formula (34), X ₃₁ , X ₃₂ , X ₃₄ , and X ₃₆ are each independently a nitrogen atom or CR ₃₁ ,
R ₃₁ is a hydrogen atom or a substituent, and the substituent in R ₃₁ is
Halogen atoms,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted trialkylsilyl group,
A substituted or unsubstituted arylalkylsilyl group,
A substituted or unsubstituted triarylsilyl group,
Substituted or unsubstituted diarylphosphine oxide groups,
A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, provided that The substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R ₃₁ is a non-condensed ring,
In the said General formula (33) and the said General formula (34), a wavy line part represents the coupling | bond part with the other atom or other structure in the molecule | numerator of the said 3rd material. ) The organic electroluminescence device according to claim 12,
R ₃₁ is a hydrogen atom or a substituent, and the substituent in R ₃₁ is
Halogen atoms,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, provided that The organic electroluminescent device wherein the substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R ₃₁ is a non-condensed ring. The organic electroluminescence device according to claim 12,
The organic electroluminescence device wherein R ₃₁ is a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. . In the organic electroluminescent element according to any one of claims 12 to 14,
The organic electroluminescence device, wherein X ₃₁ , X ₃₂ , X ₃₄ , and X ₃₆ are each independently CR ₃₁ . In the organic electroluminescent element according to any one of claims 11 to 15,
The partial structure represented by the general formula (32) includes the following general formula (35), the following general formula (36), the following general formula (37), the following general formula (38), the following general formula (39), and The organic electroluminescent element contained in said 3rd material as at least any group selected from the group which consists of the following general formula (30a).

(In the general formulas (35) to (39) and (30a),
Y _{31 to} Y ₃₈ are each independently a nitrogen atom or CR ₃₂ ,
R ₃₂ is a hydrogen atom or a substituent, and the substituent in R ₃₂ is
Halogen atoms,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted trialkylsilyl group,
A substituted or unsubstituted arylalkylsilyl group,
A substituted or unsubstituted triarylsilyl group,
Substituted or unsubstituted diarylphosphine oxide groups,
A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, provided that The substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R ₃₂ is a non-condensed ring,
In the general formulas (35) to (36), Y ₃₉ is a nitrogen atom,
In the general formulas (37) to (39) and (30a), Y ₃₉ is NR ₃₃ , an oxygen atom, or a sulfur atom,
R ₃₃ is a substituent, the substituent in the _{R 33} is
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms,
A substituted or unsubstituted arylsilyl group having 6 to 50 ring carbon atoms,
A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, provided that The substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R ₃₃ is a non-condensed ring,
In the general formulas (35) to (39) and (30a), the wavy line part represents a bonding site with another atom or another structure in the molecule of the third material. ) The organic electroluminescence device according to claim 16,
R ₃₂ is a hydrogen atom or a substituent, and the substituent in R ₃₂ is
Halogen atoms,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, provided that The organic electroluminescence device wherein the substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R ₃₂ is a non-condensed ring. The organic electroluminescence device according to claim 16,
R ₃₂ is a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. . In the organic electroluminescent element according to any one of claims 16 to 18,
In the general formula (35), Y _{31 to} Y ₃₈ are each independently CR ₃₂ ,
In the general formula (36) and the general formula (37), Y _{31 to} Y ₃₅ , Y ₃₇ , and Y ₃₈ are each independently CR ₃₂ ,
In the general formula (38), Y ₃₁ , Y ₃₂ , Y ₃₄ , Y ₃₅ , Y ₃₇ , Y ₃₈ are each independently CR ₃₂ ,
In the general formula (39), Y _{32 to} Y ₃₈ are each independently CR ₃₂ ,
In the general formula (30a), Y _{32 to} Y ₃₇ are each independently an organic electroluminescent element that is CR ₃₂ . In the organic electroluminescent element according to any one of claims 11 to 19,
Said 3rd material is an organic electroluminescent element containing group represented by the following general formula (30b).

(In the general formula (30b),
X ₃₁ , X ₃₂ , X ₃₄ , and X ₃₆ are each independently a nitrogen atom or CR ₃₁ ,
Y ₃₁ , Y ₃₂ , Y _{34 to} Y ₃₈ are each independently a nitrogen atom, CR ₃₂ , or a carbon atom that binds to another atom in the molecule of the third material,
R ₃₁ and R ₃₂ are each independently a hydrogen atom or a substituent, and the substituent in R ₃₁ and R ₃₂ is
Halogen atoms,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted trialkylsilyl group,
A substituted or unsubstituted arylalkylsilyl group,
A substituted or unsubstituted triarylsilyl group,
Substituted or unsubstituted diarylphosphine oxide groups,
A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, provided that The substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R ₃₁ and R ₃₂ is a non-condensed ring,
Y ₃₉ is NR ₃₃ , an oxygen atom, or a sulfur atom,
R ₃₃ is a substituent, the substituent in the _{R 33} is
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms,
A substituted or unsubstituted arylsilyl group having 6 to 50 ring carbon atoms,
A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, provided that The substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R ₃₃ is a non-condensed ring,
X ₃₂ and Y ₃₄ may be cross-linked via an oxygen atom, a sulfur atom, or CR ₅₁ R ₅₂ ,
X ₃₄ and Y ₃₂ may be bridged via an oxygen atom, a sulfur atom, or CR ₅₃ R ₅₄ ,
R _{51 to} R ₅₄ are each independently synonymous with the substituent in R ₃₃ ,
In the general formula (30b), a wavy line portion represents a bonding site with another atom or another structure in the molecule of the third material. ) In the organic electroluminescent element according to any one of claims 11 to 20,
Said 3rd material is an organic electroluminescent element containing group represented by the following general formula (30c).


(In the general formula (30c),
X ₃₁ , X ₃₂ , X ₃₄ , and X ₃₆ are each independently a nitrogen atom or CR ₃₁ ,
Y ₃₁ , Y ₃₂ , Y ₃₄ , Y ₃₅ , Y ₃₇ , Y ₃₈ are each independently a nitrogen atom or CR ₃₂ ,
Y _{41 to} Y ₄₅ , Y ₄₇ and Y ₄₈ are each independently a nitrogen atom, CR ₃₄ , or a carbon atom bonded to another atom in the molecule of the third material;
R ₃₁ , R ₃₂ , and R ₃₄ are each independently a hydrogen atom or a substituent, and the substituents in R ₃₁ , R ₃₂ , and R ₃₄ are
Halogen atoms,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted trialkylsilyl group,
A substituted or unsubstituted arylalkylsilyl group,
A substituted or unsubstituted triarylsilyl group,
Substituted or unsubstituted diarylphosphine oxide groups,
A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, provided that The substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R ₃₁ , R ₃₂ , and R ₃₄ is a non-condensed ring,
Y ₃₉ is NR ₃₃ , an oxygen atom, or a sulfur atom,
Y ₄₉ is NR ₃₅ , an oxygen atom, or a sulfur atom,
R ₃₃ and R ₃₅ are each independently a substituent, and the substituent in R ₃₃ and R ₃₅ is
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms,
A substituted or unsubstituted arylsilyl group having 6 to 50 ring carbon atoms,
A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, provided that The substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R ₃₃ and R ₃₅ is a non-condensed ring,
X ₃₂ and Y ₃₄ may be cross-linked via an oxygen atom, a sulfur atom, or CR ₅₁ R ₅₂ ,
X ₃₄ and Y ₃₂ may be bridged via an oxygen atom, a sulfur atom, or CR ₅₃ R ₅₄ ,
R _{51 to} R ₅₄ each independently have the same meaning as the substituent in R ₃₃ and R ₃₅ ,
In the general formula (30c), a wavy line portion represents a bonding site with another atom or another structure in the molecule of the third material. ) In the organic electroluminescent element according to any one of claims 11 to 21,
Said 3rd material is an organic electroluminescent element containing group represented by the following general formula (30d).
(In the general formula (30d),
X ₃₁ , X ₃₂ , X ₃₄ , and X ₃₆ are each independently a nitrogen atom or CR ₃₁ ,
X ₄₁ , X ₄₃ , X ₄₄ , and X ₄₅ are each independently a nitrogen atom or CR ₃₆ ,
R ₃₁ and R ₃₆ are each independently a hydrogen atom or a substituent, and the substituent in R ₃₁ and R ₃₆ is
Halogen atoms,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted trialkylsilyl group,
A substituted or unsubstituted arylalkylsilyl group,
A substituted or unsubstituted triarylsilyl group,
Substituted or unsubstituted diarylphosphine oxide groups,
A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, provided that The substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R ₃₁ and R ₃₆ is a non-condensed ring,
X ₃₂ and X ₄₁ may be cross-linked via an oxygen atom, a sulfur atom, or CR ₅₅ R ₅₆ ,
X ₃₄ and X ₄₅ may be cross-linked via an oxygen atom, a sulfur atom, or CR ₅₇ R ₅₈ ,
R ₅₅ to R ₅₈ are each independently a substituent, the substituent in the _R 55 _{to R 58} are,
Halogen atoms,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms,
A substituted or unsubstituted arylsilyl group having 6 to 50 ring carbon atoms,
A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, provided that the aromatic hydrocarbon group _R 55 substituted or unsubstituted in _{to R 58} ring-forming having 6 to 30 carbon atoms is a non-fused ring,
In the general formula (30d), the wavy line portion represents a bonding site with another atom or another structure in the molecule of the third material. ) The organic electroluminescence device according to any one of claims 11 to 22,
The third material is an organic electroluminescence element including a group represented by the following general formula (30e).
(In the general formula (30e),
X ₃₁ , X ₃₂ , X ₃₄ , and X ₃₆ are each independently a nitrogen atom or CR ₃₁ ,
X ₄₁ , X ₄₃ , X ₄₄ , and X ₄₅ are each independently a nitrogen atom or CR ₃₆ ,
Y _{31 to} Y ₃₅ , Y ₃₇ and Y ₃₈ are each independently a nitrogen atom, CR ₃₂ , or a carbon atom bonded to another atom in the molecule of the third material,
R ₃₁ , R ₃₂ , and R ₃₆ are each independently a hydrogen atom or a substituent, and the substituents in R ₃₁ , R ₃₂ , and R ₃₆ are
Halogen atoms,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted trialkylsilyl group,
A substituted or unsubstituted arylalkylsilyl group,
A substituted or unsubstituted triarylsilyl group,
Substituted or unsubstituted diarylphosphine oxide groups,
A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, provided that The substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R ₃₁ , R ₃₂ and R ₃₆ is a non-condensed ring,
Y ₃₉ is NR ₃₃ , an oxygen atom, or a sulfur atom,
R ₃₃ is a substituent, the substituent in the _{R 33} is
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms,
A substituted or unsubstituted arylsilyl group having 6 to 50 ring carbon atoms,
A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, provided that The substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R ₃₃ is a non-condensed ring,
X ₃₂ and X ₄₁ may be cross-linked via an oxygen atom, a sulfur atom, or CR ₅₅ R ₅₆ ,
X ₃₄ and X ₄₅ may be cross-linked via an oxygen atom, a sulfur atom, or CR ₅₇ R ₅₈ ,
X ₄₁ and Y ₃₇ may be cross-linked via an oxygen atom, a sulfur atom, or CR ₅₉ R ₆₀ ,
X ₄₃ and Y ₃₅ may be cross-linked via an oxygen atom, a sulfur atom, or CR ₆₁ R ₆₂ ,
R ₅₅ to R ₆₂ each independently has the same meaning as the substituent in the _{R 33,}
In the general formula (30e), the wavy line portion represents a bonding site with another atom or another structure in the molecule of the third material. ) In the organic electroluminescent element according to any one of claims 11 to 23,
The third material is an organic electroluminescence device including a group represented by the following general formula (30f).
(In the general formula (30f),
Y ₃₁ , Y ₃₂ , Y ₃₄ , Y ₃₅ , Y ₃₇ , Y ₃₈ are each independently a nitrogen atom or CR ₃₂ ,
Y _{41 to} Y ₄₅ , Y ₄₇ and Y ₄₈ are each independently a nitrogen atom, CR ₃₄ , or a carbon atom bonded to another atom in the molecule of the third material;
R ₃₂ and R ₃₄ are each independently a hydrogen atom or a substituent, and the substituent in R ₃₂ and R ₃₄ is
Halogen atoms,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted trialkylsilyl group,
A substituted or unsubstituted arylalkylsilyl group,
A substituted or unsubstituted triarylsilyl group,
Substituted or unsubstituted diarylphosphine oxide groups,
A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, provided that The substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R ₃₂ and R ₃₄ is a non-condensed ring,
Y ₃₉ is NR ₃₃ , an oxygen atom, or a sulfur atom,
Y ₄₉ is NR ₃₅ , an oxygen atom, or a sulfur atom,
R ₃₃ and R ₃₅ are each independently a hydrogen atom or a substituent, and the substituent in R ₃₃ and R ₃₅ is,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms,
A substituted or unsubstituted arylsilyl group having 6 to 50 ring carbon atoms,
A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, provided that The substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R ₃₃ and R ₃₅ is a non-condensed ring,
In the general formula (30f), a wavy line portion represents a bonding site with another atom or another structure in the molecule of the third material. ) In the organic electroluminescence device according to claim 11, claim 20, or claim 23,
Y ₃₉ is an organic electroluminescence device in which oxygen atom or sulfur atom. In the organic electroluminescence device according to claim 11, claim 20, or claim 23,
Y ₃₉ is an organic electroluminescence device in which an oxygen atom is present. In the organic electroluminescence device according to claim 21 or claim 24,
The organic electroluminescence device, wherein Y ₃₉ and Y ₄₉ are each independently an oxygen atom or a sulfur atom. In the organic electroluminescence device according to claim 21 or claim 24,
Wherein _{Y 39} and the _{Y 49} is an organic electroluminescent device is an oxygen atom. The organic electroluminescence device according to any one of claims 1 to 28,
The third material is an organic electroluminescence device having no condensed aromatic hydrocarbon ring in the molecule. The organic electroluminescence device according to any one of claims 1 to 29,
The light emitting layer is an organic electroluminescence device that does not contain a phosphorescent metal complex. In the organic electroluminescent element according to any one of claims 1 to 30,
The first material is an organic electroluminescence device exhibiting fluorescence emission having a main peak wavelength of 550 nm or less. The organic electroluminescent element according to any one of claims 1 to 31,
The first material is an organic electroluminescence device exhibiting fluorescence emission having a main peak wavelength of 480 nm or less. In the organic electroluminescent element according to any one of claims 1 to 32,
The first material is at least one selected from the group consisting of pyrene derivatives, aminoanthracene derivatives, aminochrysene derivatives, aminopyrene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, and styrylamine derivatives. An organic electroluminescence device which is a compound.   An electronic device comprising the organic electroluminescence element according to any one of claims 1 to 33.