JP2021118354A - Organic electroluminescent devices and anthracene compounds - Google Patents

Abstract

An organic EL device having high external quantum efficiency is provided. An organic electroluminescence device (100) having a pair of electrodes consisting of an anode (102) and a cathode (108) and a light-emitting layer (105) disposed between the pair of electrodes, wherein the light-emitting layer comprises a host material of the following formula ( An organic electroluminescence device comprising an anthracene compound represented by 1) and a polycyclic aromatic compound represented by the following formula (2) or a multimer thereof as a dopant material. [Selection figure] None

Description

The present invention relates to an organic electroluminescent device, a display device using the organic electroluminescent device, and a lighting device. The present invention also relates to an anthracene compounds that can be used as light emitting materials.

Conventionally, display devices using electroluminescent elements that emit electroluminescence have been studied in various ways because they can save power and become thinner. Further, organic electroluminescent elements made of organic materials (hereinafter referred to as "organic EL elements") are used. ) Has been actively studied because it is easy to reduce the weight and increase the size. In particular, the development of organic materials with luminescent properties such as blue, which is one of the three primary colors of light, and the combination of multiple materials with optimal luminescent properties have been actively pursued regardless of whether they are high molecular weight compounds or low molecular weight compounds. Has been studied.

The organic EL element has a structure composed of a pair of electrodes composed of an anode and a cathode, and one layer or a plurality of layers containing an organic compound, which is arranged between the pair of electrodes. Layers containing organic compounds include light emitting layers and charge transport / injection layers that transport or inject charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

Patent Document 1 describes that an anthracene compound is used as a light emitting material for an organic electroluminescent device. Further, in recent years, a polycyclic aromatic compound obtained by condensing a plurality of aromatic rings with boron or the like as a central atom has been reported as a material for an organic electroluminescent element (Patent Document 2).

International Publication No. 2006/003842 International Publication No. 2015/102118

As described above, various materials used for organic EL devices have been developed, but in order to increase the choices of materials for organic EL devices, it is desired to develop a material made of a compound different from the conventional one. It is rare. An object of the present invention is to provide an organic EL device using a new combination of materials. An object of the present invention is to provide an organic EL device having high external quantum efficiency.

As a result of diligent studies to solve the above problems, the present inventors use a light emitting layer containing a specific anthracene compound as a host material and a polycyclic aromatic compound in which a plurality of aromatic rings are condensed as a dopant material. As a result, it was found that an excellent organic EL element can be obtained, and the present invention has been completed. That is, the present invention provides the following organic electroluminescent device and anthracene-based compound.

<1> An organic electroluminescent element having a pair of electrodes composed of an anthracene and a cathode and a light emitting layer arranged between the pair of electrodes. The light emitting layer is represented by the following formula (1) as a host material. An organic compound containing an anthracene compound and a multimer of a polycyclic aromatic compound represented by the following formula (2) or a polycyclic aromatic compound having a plurality of structures represented by the following formula (2) as a dopant material. Electroluminescent element.

In equation (1),
Ar ^c is a heteroaryl optionally are also aryl or substituted optionally be substituted,
R ^c is hydrogen, alkyl, or cycloalkyl,
Ar ¹¹ , Ar ¹² , Ar ¹³ , Ar ¹⁴ , Ar ¹⁵ , Ar ¹⁶ , Ar ¹⁷ , and Ar ¹⁸ are independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, respectively. Diarylamino which may be substituted, diheteroarylamino which may be substituted, arylheteroarylamino which may be substituted, alkyl which may be substituted, cycloalkyl which may be substituted, cycloalkyl which may be substituted, An alkenyl which may be substituted, an alkoxy which may be substituted, an aryloxy which may be substituted, an arylthio which may be substituted, or a silyl which may be substituted.
At least one hydrogen in the compound represented by the formula (1) may be substituted with halogen, cyano, or deuterium.

In equation (2),
Rings A, B, and C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted.
X ¹ and X ² are independently>O,>N-R,> C (-R) ₂ ,> S, or> Se, even if the R of> N-R is substituted. A good aryl, a heteroaryl which may be substituted, an alkyl which may be substituted, or a cycloalkyl which may be substituted, and the R of> C (-R) ₂ is hydrogen, even if it is substituted. A good aryl, an alkyl which may be substituted, or a cycloalkyl which may be substituted, and the R of> N-R and / or the R of> C (-R) ₂ may be a linking group or a simple substance. It may be bonded to the A ring, the B ring, and / or the C ring by the bond.
At least one of the aryl ring and the heteroaryl ring in the compound represented by the formula (2) or a multimer thereof may be condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane is substituted. At least one −CH ₂ − in the cycloalkane may be substituted with −O−.
At least one hydrogen in the compound or structure represented by the formula (2) may be substituted with deuterium, cyano, or halogen.

<2> The polycyclic aromatic compound represented by the formula (2) or the multimer of the polycyclic aromatic compound having a plurality of structures represented by the formula (2) is represented by the formulas (2-a) and (2-a). b), formula (2-c), formula (2-d), formula (2-e), or polycyclic aromatic compound represented by formula (2-f) or formula (2-a), formula (2-a). A multimer of a polycyclic aromatic compound having a plurality of structures represented by 2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f). The organic electric field light emitting element according to <1>;

In formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f),
R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , and R ¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, respectively. Diheteroarylamino, arylheteroarylamino, diallylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyls, which are these. At least one hydrogen in is optionally substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R. ^{Adjacent groups of 8} , R ⁹ , R ¹⁰ , and R ¹¹ may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, b ring, or c ring, and the formed ring may be formed. At least one hydrogen in is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, and. It may be substituted with cycloalkyl, alkoxy, aryloxy, or substituted silyls, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyls.
X _X is independently,>O,> S, a> N-R or> C _{(-R) 2,,} wherein> N-R of R is optionally substituted aryl, optionally substituted It may be heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and the R of> C (-R) ₂ may be independently hydrogen, alkyl or cyclo, respectively. Aryl, alkyl or cycloalkyl, optionally substituted, heteroaryl, alkyl, or cycloalkyl, which may be substituted with alkyl.
X ¹ and X ² are independently>O,>N-R,> C (-R) ₂ ,> S, or> Se, and the R of> N-R has 1 to 1 carbon atoms. It may be substituted with an alkyl of 6 or a cycloalkyl having 3 to 14 carbon atoms, an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms. Heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, and R of> C (-R) ₂ is hydrogen, alkyl having 1 to 6 carbon atoms. Alternatively, it may be substituted with a cycloalkyl having 3 to 14 carbon atoms, an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and the above-mentioned> N- R of R and / or R of> C (-R) ₂ is -O-, -S-, -C (-R) _2- , or the a ring, b ring, and / or c ring by a single bond. The -C (-R) _2- R may be independently an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms.
A compound represented by the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e), or the formula (2-f) or a large amount thereof. At least one of the aryl and heteroaryl rings in the body may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one in the cycloalkane. One −CH ₂₋ may be replaced by −O−
In a compound or structure represented by the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e), or the formula (2-f). At least one hydrogen may be substituted with deuterium, cyano, or halogen.
In the case of a trimer, the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e), or the formula (2-f) It is a dimer or trimer having 2 or 3 structures represented.

<3> The compound represented by the formula (2) is a polycyclic aromatic compound represented by the formula (2-a) or the formula (2-b) or the formula (2-a) or the formula (2-b). The organic electroluminescent element according to <2>, which is a multimer of a polycyclic aromatic compound having a plurality of structures represented by.

<4> The organic electroluminescent device according to <3>, wherein the compound represented by the formula (2) is any of the compounds represented by the following formula;

上記式中、Ｍｅはメチルであり、ｔＢｕはｔ−ブチルであり、ｔＡｍはｔ−アミルであり、Ｄは重水素である。

In the above formula, Me is methyl, tBu is t-butyl, tAm is t-amyl, and D is deuterium.

<5> In the formula (1), any two of Ar ¹¹ , Ar ¹² , Ar ¹³ , Ar ¹⁴ , Ar ¹⁵ , Ar ¹⁶ , Ar ¹⁷ , and Ar ¹⁸ may be substituted aryl or substituted. A good heteroaryl, the other six being hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, or optionally substituted alkoxy, <1. > The organic electric field light emitting element according to any one of <4>.

<6> The anthracene-based compound represented by the formula (1) is an anthracene-based compound represented by the following formulas (1A), (1B), (1C), (1D), or (1E), <5>. The organic electroluminescent device according to the above;

In formula (1A), (1B), (1C), (1D) or (1E),
^{Ar c ', Ar 11',} Ar 12 ', Ar 13', Ar 14 ', Ar 15', Ar 17 ', and ^{Ar 18'} each independently phenyl, biphenylyl, terphenylyl, quaterphenylene phenylene Lil, naphthyl, A group represented by phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or formula (A), and at least one hydrogen in these groups is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl. , Phenyltril, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by the formula (A), wherein the two hydrogens of methylene in fluorenyl and benzofluorenyl are here. When both are substituted with phenyls, these phenyls may be single bonded to each other.
^{Ar c ', Ar 11',} Ar 12 ', Ar 13', Ar 14 ', Ar 15', Ar 17 ', or ^{Ar 18'} is a carbon atom on the anthracene ring which is not bound methyl instead of hydrogen Alternatively, t-butyl may be bonded,
At least one hydrogen in the compound represented by the formulas (1A), (1B), (1C), (1D) or (1E) may be halogen, cyano, or deuterium substituted.
The group represented by the formula (A) is a group obtained by removing one hydrogen at any position of the formula (A), and * indicates the position.
In formula (A), Y is -O-, -S- or> N-R ³⁹ , and R ^{21 to} R ²⁸ are independently hydrogen, optionally substituted alkyl, optionally substituted, respectively. Cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tri. Cycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano, the ^{adjacent groups of R 21-} R ²⁸ are bonded to each other to form a hydrocarbon ring. An aryl ring or a heteroaryl ring may be formed, and at least one hydrogen in the formed hydrocarbon ring, aryl ring or heteroaryl ring may be an alkyl substituted or a cycloalkyl substituted. , Aryl which may be substituted, heteroaryl which may be substituted, alkoxy which may be substituted, aryloxy which may be substituted, arylthio which may be substituted, trialkylsilyl, tricycloalkyl. It may be substituted with silyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy, or cyano, and R ³⁹ is hydrogen or optionally substituted aryl.

<7> The group represented by the formula (A) is a group represented by any of the formulas (A-1) to (A-14).
The groups represented by the formulas (A-1) to (A-14) are groups obtained by removing one hydrogen at any position of the formulas (A-1) to (A-14). And * indicates the position,
In formulas (A-1) to (A-14), Y is -O-, -S-, or> N-R ³⁹ , R ³⁹ is hydrogen or aryl, and formulas (A-1) to-. At least one hydrogen in the group represented by the formula (A-14) is alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyl. It may be substituted with dicycloalkylsilyl, diaryl substituted amino, diheteroaryl substituted amino, aryl heteroaryl substituted amino, halogen, hydroxy, or cyano,
The organic electroluminescent device according to <6>.

^{<8> Ar c ', Ar} 11', Ar 12 ', Ar 13', Ar 14 ', Ar 15', Ar 17 ', and ^{Ar 18'} are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, Fluolenyl, or a group represented by any of formulas (A-1) to (A-4), at least one hydrogen in these groups is phenyl, biphenylyl, naphthyl, phenanthryl, fluorenyl, or formula ( It may be substituted with a group represented by any of A-1) to (A-4).
At least one hydrogen in the compound represented by the formulas (1A), (1B), (1C), (1D) or (1E) may be substituted with halogen, cyano, or deuterium.
The organic electroluminescent device according to <6> or <7>.

<9> Ar ¹⁴ and Ar ¹⁵ are optionally substituted aryls or optionally substituted heteroaryls, and Ar ¹¹ , Ar ¹² , Ar ¹³ , Ar ¹⁶ , Ar ^17, and Ar ¹⁸ are all hydrogen. The organic electroluminescent element according to <5>.
<10> The organic electroluminescent device according to <9>, wherein at least one selected from the group consisting of ^{Ar C} , Ar ¹⁴ , and Ar ^{15 is a group containing an anthracene ring.}

<11> The organic electroluminescent device according to <9>, wherein at least one selected from the group consisting of ^{Ar C} , Ar ¹⁴ , and Ar ^{15 contains a group represented by the formula (A');}

In formula (A'), R ^{21 to} R ²⁸ are independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted, respectively. Heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, substituted It may be amino, halogen, hydroxy or cyano, and ^{adjacent groups of R 21 to} R ²⁸ may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring, which may be formed. At least one hydrogen in a hydrocarbon ring, an aryl ring or a heteroaryl ring may be an alkyl optionally substituted, a cycloalkyl optionally substituted, an aryl optionally substituted, a heteroaryl optionally substituted. , Substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, substituted It may be substituted with amino, halogen, hydroxy, or cyano.

<12> The organic electroluminescent device according to <9>, wherein at least one hydrogen in the compound represented by the formula (1) is replaced with deuterium.
<13> It has an electron transporting layer and / or an electron injecting layer arranged between the cathode and the light emitting layer, and at least one of the electron transporting layer and the electron injecting layer is a borane derivative, a pyridine derivative, or fluoranthene. Derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzoimidazole derivatives, phenanthroline derivatives, quinolinol metal complexes, thiazole derivatives, benzothiazole derivatives, silol derivatives, and The organic electric field light emitting element according to any one of <1> to <12>, which contains at least one selected from the group consisting of azoline derivatives.

<14> The electron transporting layer and / or electron injecting layer further comprises an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, and an alkaline soil. Contains at least one selected from the group consisting of metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes. , <13>.
<15> A display device provided with the organic electroluminescent device according to any one of <1> to <14>.
<16> A lighting device provided with the organic electroluminescent device according to any one of <1> to <14>.

<17> Anthracene-based compound represented by the following formula (1);

In equation (1),
Ar ^c is a heteroaryl optionally are also aryl or substituted optionally be substituted,
R ^c is hydrogen, alkyl, or cycloalkyl,
Ar ¹¹ , Ar ¹² , Ar ¹³ , Ar ¹⁴ , Ar ¹⁵ , Ar ¹⁶ , Ar ¹⁷ , and Ar ¹⁸ are independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, respectively. Diarylamino which may be substituted, diheteroarylamino which may be substituted, arylheteroarylamino which may be substituted, alkyl which may be substituted, cycloalkyl which may be substituted, cycloalkyl which may be substituted, An alkenyl which may be substituted, an alkoxy which may be substituted, an aryloxy which may be substituted, an arylthio which may be substituted, or a silyl which may be substituted.
At least one hydrogen in the compound represented by the formula (1) may be substituted with halogen, cyano, or deuterium.

<18> The anthracene compound according to <17> represented by the following formula (1Aa);

Wherein ^{(1Aa), Ar c ',} Ar 14', and ^{Ar 15} 'are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or formula, ( It is a group represented by any of A-1) to the formula (A-14), and at least one hydrogen in these groups is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzo. It may be substituted with fluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any of formulas (A-1) to (A-14), wherein in fluorenyl and benzofluorenyl. when the hydrogen of the methylene is substituted with either a phenyl, these phenyl may be attached by a single bond to each ^{other, Ar c ', Ar 14'} , or Ar 15 ^'is unbound on anthracene ring Methyl or t-butyl may be bonded to the carbon atom of the above instead of hydrogen.
At least one hydrogen in the compound represented by the formula (1Aa) may be substituted with halogen, cyano, or deuterium.
The groups represented by the formulas (A-1) to (A-14) are groups obtained by removing one hydrogen at any position of the formulas (A-1) to (A-14). And * indicates the position,
In formulas (A-1) to (A-14), Y is -O-, -S-, or> N-R ³⁹ , R ³⁹ is hydrogen or aryl, and formulas (A-1) to-. At least one hydrogen in the group represented by the formula (A-14) is alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyl. It may be substituted with dicycloalkylsilyl, diaryl substituted amino, diheteroaryl substituted amino, aryl heteroaryl substituted amino, halogen, hydroxy, or cyano.
However, at least one hydrogen in the compound represented by the formula (1Aa) may be substituted with halogen or cyano, and at least one hydrogen in the compound represented by the formula (1Aa) is substituted with deuterium. ..

Table with either ^{<19> Ar c ', Ar} 14' and ^{Ar 15} 'are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl or formula (A-1) ~ formula, (A-4) At least one hydrogen in these groups is substituted with phenyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any of formulas (A-1) to (A-4). The anthracene-based compound according to <18> may be used.
<20> The anthracene-based compound according to <18> or <19>, wherein at least the hydrogen bonded to the 10-position of the anthracene ring is replaced with deuterium in the formula (1Aa).

<21> The anthracene-based compound according to <18> represented by any of the following formulas.

（上記式中、Ｄは重水素を示す。）

(In the above formula, D represents deuterium.)

<22> The anthracene-based compound according to <17> represented by any of the following formulas.

（上記式中、Ｄは重水素を示す。）

(In the above formula, D represents deuterium.)

<23> The anthracene-based compound according to <17> represented by any of the following formulas.

<24> The anthracene-based compound according to <17> represented by any of the following formulas.

（上記式中、Ｄは重水素を示す。）

(In the above formula, D represents deuterium.)

<25> The anthracene-based compound according to <17> represented by any of the following formulas.

（上記式中、Ｄは重水素を示す。）

(In the above formula, D represents deuterium.)

（上記式中、Ｍｅはメチル、ｔＢｕはｔ−ブチル、ＣｙＨｅｘはシクロヘキシルを示す。） <26> The anthracene-based compound according to <17> represented by any of the following formulas.

(In the above formula, Me is methyl, tBu is t-butyl, and CyHex is cyclohexyl.)

<27> The anthracene-based compound according to <17> represented by any of the following formulas.

（上記式中、Ｄは重水素を示す。）

(In the above formula, D represents deuterium.)

The present invention provides an organic EL device using a new combination of materials. The organic EL device of the present invention has high external quantum efficiency and is capable of emitting light at a low voltage. The present invention also provides an anthracene-based compound that can be used in the production of the organic EL device.

It is the schematic sectional drawing which shows an example of the organic EL element of this invention.

Hereinafter, the present invention will be described in detail. The description of the constituent elements described below may be based on typical embodiments or specific examples, but the present invention is not limited to such embodiments. In this specification, the numerical range represented by using "~" means a range including the numerical values before and after "~" as the lower limit value and the upper limit value. Further, in the present specification, "hydrogen" in the description of the structural formula means "hydrogen atom (H)".

In the present specification, the chemical structure or substituent may be represented by the number of carbon atoms, but the number of carbon atoms when the chemical structure is substituted with a substituent or when the substituent is further substituted with a substituent is the chemical structure or substitution. It means the carbon number of each group, and does not mean the total carbon number of the chemical structure and the substituent or the total carbon number of the substituent and the substituent. For example, "substituent B of carbon number Y substituted with substituent A of carbon number X" means that "substituent A of carbon number X" is substituted with "substituent B of carbon number Y". However, the number of carbon atoms Y is not the total number of carbon atoms of the substituent A and the substituent B. Further, for example, "substituent B having a carbon number Y substituted with a substituent A" means that "substituent A (with no limitation on the number of carbon atoms)" is substituted for "substituent B having a carbon number Y". However, the number of carbon atoms Y is not the total number of carbon atoms of the substituent A and the substituent B.

<< Organic electroluminescent device >>
The organic electroluminescent device of the present invention has a pair of electrodes including an anode and a cathode, and a light emitting layer arranged between the pair of electrodes. FIG. 1 is a schematic cross-sectional view showing an example of the organic EL device of the present invention.

The organic EL element 100 shown in FIG. 1 is placed on a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, and a hole injection layer 103. The hole transport layer 104 is provided, the light emitting layer 105 is provided on the hole transport layer 104, the electron transport layer 106 is provided on the light emitting layer 105, and the electron transport layer 106 is provided. It has an electron injection layer 107 and a cathode 108 provided on the electron injection layer 107.

The organic EL element 100 is manufactured in the reverse order, for example, the substrate 101, the cathode 108 provided on the substrate 101, the electron injection layer 107 provided on the cathode 108, and the electron injection layer 107. Above the electron transport layer 106 provided on the electron transport layer 106, the light emitting layer 105 provided on the electron transport layer 106, the hole transport layer 104 provided on the light emitting layer 105, and the hole transport layer 104. The hole injection layer 103 provided in the hole injection layer 103 and the anode 102 provided on the hole injection layer 103 may be provided.

Not all of the above layers are required, and the minimum structural unit is composed of the anode 102, the light emitting layer 105, and the cathode 108, and the hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection. The layer 107 is an arbitrarily provided layer. Further, each of the above layers may be composed of a single layer or a plurality of layers.

As the mode of the layer constituting the organic EL element, in addition to the above-mentioned "board / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode", " Substrate / anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode "," substrate / anode / hole injection layer / light emitting layer / electron transport layer / electron injection layer / cathode "," substrate / Anode / hole injection layer / hole transport layer / light emitting layer / electron injection layer / cathode "," substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode "," substrate / Anode / light emitting layer / electron transport layer / electron injection layer / cathode "," substrate / anode / hole transport layer / light emitting layer / electron injection layer / cathode "," substrate / anode / hole transport layer / light emitting layer / electron "Transportation layer / Anode", "Substrate / Anode / Hole injection layer / Light emitting layer / Electron injection layer / Cathode", "Substrate / Anode / Hole injection layer / Light emitting layer / Electron transport layer / Cathode", "Substrate / Anode" The configuration may be "/ light emitting layer / electron transporting layer / cathode" or "substrate / anode / light emitting layer / electron injection layer / cathode".

1. 1. The light emitting layer light emitting layer 105 in the organic electroluminescent element emits light by recombining the holes injected from the anode 102 and the electrons injected from the cathode 108 between the electrodes to which an electric field is applied. .. The material for forming the light emitting layer 105 may be a compound (light emitting compound) that is excited by recombination of holes and electrons to emit light, and can form a stable thin film shape and is in a solid state. It is preferable that the compound exhibits a strong emission (fluorescence) efficiency.

There are mainly two light emitting mechanisms of the organic EL element: fluorescence light emission using light emission from the excited singlet state and phosphorescence light emission using light emission from the excited triplet state. A general fluorescent material has a low exciton utilization efficiency, which is 25% at the maximum. However, a maximum of 40 to 62.5% of energy can be used for light emission by using the phenomenon that singlet excitons are generated from a plurality of triplet excitons (triplet-triplet fusion (TTF)).

The generation of singlet excitons from triplet excitons can occur in two ways: on the host material molecule and on the dopant material molecule. At this time, the triplet energy level of the dopant material is preferably higher than the triplet energy level of the host material. When this triplet energy level relationship is satisfied, triplet excitons generated on the host material do not move to the dopant material with higher triplet energy. In addition, triplet excitons generated on the dopant material molecule rapidly transfer energy to the host material molecule. That is, the triplet excitons of the host material do not move to the dopant material, and the triplet excitons collide with each other efficiently on the host material to generate singlet excitons. Further, when the singlet energy level of the dopant material is lower than the singlet energy level of the host material, the singlet exciter generated by the TTF phenomenon rapidly transfers energy from the host material to the dopant material and fluoresces the dopant material. Contributes to sexual emission. The energy transfer from the host to the dopant at this time is a Felster type energy transfer. Generally, in an organic EL device, the overlap integral of the fluorescence spectrum of the host and the absorption spectrum of the dopant is large, and highly efficient Felster-type energy transfer occurs when the host and the dopant are close to each other and have an appropriate orientation. It has been known.

If a host material which is an anthracene-based compound represented by the formula (1) of the present invention and a dopant material which is a polycyclic aromatic compound having boron represented by the formula (2) are used, the above-mentioned host and dopant can be used. It is possible to design materials and elements that satisfy the relationship of appropriate energy levels and the conditions under which highly efficient Felster-type energy transfer occurs. As a result, the TTF phenomenon can be efficiently generated in the light emitting layer of the present invention, and good element characteristics can be provided.

The light emitting layer of the organic electroluminescent element of the present invention is represented by an anthracene compound represented by the formula (1) as a host material and a polycyclic aromatic compound represented by the formula (2) or a polycyclic aromatic compound represented by the formula (2) as a dopant material. It contains a multimer of a polycyclic aromatic compound having a plurality of structures to be formed.

1-1-1. Anthracene-based compound The anthracene-based compound contained in the light emitting layer of the organic EL device of the present invention is a compound represented by the following formula (1).

In formula (1), Ar ^c is an aryl that may be substituted or a heteroaryl that may be substituted, and R ^c is hydrogen, alkyl, or cycloalkyl, which is Ar ¹¹ , Ar ¹² , Ar. ¹³ , Ar ¹⁴ , Ar ¹⁵ , Ar ¹⁶ , Ar ¹⁷ , and Ar ¹⁸ are independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diaryl, respectively. Amino, optionally substituted diheteroarylamino, optionally substituted aryl heteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, substituted The alkoxy may be, the aryloxy may be substituted, the arylthio may be substituted, or the silyl may be substituted, and at least one hydrogen in the compound represented by the formula (1) is. It may be substituted with halogen, cyano, or heavy hydrogen.

Examples of the "aryl" of the "optionally substituted aryl" in the formula (1) include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 16 carbon atoms, and 6 to 12 carbon atoms. Aryl is more preferable, and aryl having 6 to 10 carbon atoms is particularly preferable.

Specific examples of "aryl" include phenyl, which is a monocyclic system, biphenylyl, which is a bicyclic system, naphthyl, which is a condensed bicyclic system, and terfenylyl, which is a tricyclic system (m-terphenylyl, o-terphenylyl, p-terphenylyl). , Condensed tricyclics such as anthracenyl, acenaphthylenyl, fluorenyl, phenylenyl, phenanthrenyl, condensed tetracyclics triphenylenyl, pyrenyl, naphthalenyl, benzofluorenyl, condensed pentacyclics perylenyl, pentasenyl and the like. In addition, in this specification, the term "fluorenyl" means that one or two of the two hydrogens of fluorenyl or methylene of fluorenyl are substituted with methyl. Further, the term "benzofluorenyl" means that one or two of the two hydrogens of benzofluorenyl or methylene of benzofluorenyl are substituted with methyl.

Examples of the "heteroaryl" of the "optionally substituted heteroaryl" in the formula (1) include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and carbon. Heteroaryls having a number of 2 to 20 are more preferable, heteroaryls having 2 to 15 carbon atoms are further preferable, and heteroaryls having 2 to 10 carbon atoms are particularly preferable. Examples of the heteroaryl include a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms.

Specific "heteroaryl" includes, for example, pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indrill, isoindrill, 1H-. Indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, synnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyldinyl, prynyl, pteridinyl, carbazolyl, acridinyl, phenoxatinyl, phenoxadinyl, phenoxadinyl Examples thereof include phenazinyl, indolidinyl, frill, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzo [b] thienyl, dibenzothienyl, frazanyl, oxadiazolyl, thiantranyl, naphthobenzofuranyl and naphthobenzothienyl.

The aryls and heteroaryls in the "optionally substituted diarylamino", "optionally substituted diheteroarylamino", and "optionally substituted aryl heteroarylamino" in the formula (1) are Those described above as "aryl" and "heteroaryl" can be cited.

Specific examples thereof include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino and naphthylpyridylamino.

The "alkyl" of the "alkyl" and the "optionally substituted alkyl" in the formula (1) may be either a straight chain or a branched chain, for example, a straight chain alkyl having 1 to 24 carbon atoms or a carbon number of carbon atoms. Examples include 3 to 24 branched chain alkyls. An alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms) is preferable, an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms) is more preferable, and an alkyl having 1 to 6 carbon atoms is more preferable. (Branched chain alkyl having 3 to 6 carbon atoms) is more preferable, and alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms) is particularly preferable.

Specific "alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1 -Methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2 -Propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, Examples thereof include n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl and n-eicocil.

Examples of the "cycloalkyl" of the "cycloalkyl" and the "optionally substituted cycloalkyl" in the formula (1) include cycloalkyl having 3 to 24 carbon atoms, and cycloalkyl having 3 to 20 carbon atoms. Alkyl is preferable, cycloalkyl having 3 to 16 carbon atoms is more preferable, cycloalkyl having 3 to 14 carbon atoms is more preferable, cycloalkyl having 5 to 10 carbon atoms is more preferable, and cycloalkyl having 5 to 8 carbon atoms is particularly preferable. Preferably, cycloalkyl having 5 to 6 carbon atoms is most preferable.

Specific cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, alkyl (particularly methyl) substituents having 1 to 4 carbon atoms, norbornenyl, and bicyclo [1]. .0.1] Butyl, Bicyclo [1.1.1] Pentyl, Bicyclo [2.0.1] Pentyl, Bicyclo [1.2.1] Hexyl, Bicyclo [3.0.1] Hexyl, Bicyclo [2] .1.2] Heptyl, bicyclo [2.2.2] Octyl, adamantyl, diamantyl, decahydronaphthalenyl, decahydroazulenyl and the like.

Examples of the "alkenyl" of the "optionally substituted alkenyl" in the formula (1) include straight chain alkenyl having 2 to 24 carbon atoms and branched chain alkenyl having 4 to 24 carbon atoms. An alkenyl having 2 to 18 carbon atoms is preferable, an alkenyl having 2 to 12 carbon atoms is more preferable, an alkenyl having 2 to 6 carbon atoms is further preferable, and an alkenyl having 2 to 4 carbon atoms is particularly preferable.
Specific examples of the "alkenyl" include vinyl, allyl, butadienyl and the like.

Examples of the “alkoxy” of the “optionally substituted alkoxy” in the formula (1) include a straight chain having 1 to 24 carbon atoms or a branched chain alkoxy having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (alkoxy of branched chains having 3 to 18 carbon atoms) is preferable, and alkoxy having 1 to 12 carbon atoms (alkoxy of branched chains having 3 to 12 carbon atoms) is more preferable, and alkoxy having 1 to 6 carbon atoms is more preferable. Alkoxy (alkoxy of a branched chain having 3 to 6 carbon atoms) is more preferable, and alkoxy having 1 to 4 carbon atoms (alkoxy of a branched chain having 3 to 4 carbon atoms) is particularly preferable.

Specific examples of "alkoxy" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy and the like.

The "aryloxy" of the "optionally substituted aryloxy" in the formula (1) is a group in which the hydrogen of the -OH group is substituted with an aryl, and this aryl is described as the above-mentioned "aryl". You can quote things.

The "arylthio" of the "optionally substituted arylthio" in the formula (1) is a group in which the hydrogen of the -SH group is substituted with an aryl, and this aryl is the "aryl" in ^{Ar 4 and X described above.} You can quote what was explained as.

Examples of the "optionally substituted silyl" in the formula (1) include trialkylsilyl. Examples of the "trialkylsilyl" include those in which the three hydrogens in the silyl are independently substituted with alkyl, and this alkyl can be cited as described as "alkyl" in ^{Ar 4 and X described above.} can. Preferred alkyls to be substituted are alkyls having 1 to 4 carbon atoms, and specific examples thereof include methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, cyclobutyl and the like. Be done.

Specific "trialkylsilyl" includes trimethylsilyl, triethylsilyl, tripropylsilyl, trii-propylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyl. Dimethylsilyl, butyldimethylsilyl, s-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, s-butyldiethylsilyl, t-butyldiethylsilyl, methyl Dipropyl silyl, ethyl dipropyl silyl, butyl dipropyl silyl, s-butyl dipropyl silyl, t-butyl dipropyl silyl, methyl di-propyl silyl, ethyl di-propyl silyl, butyl di-propyl silyl, s-butyl di i -Propylsilyl, t-butyldii-propylsilyl and the like can be mentioned.

^{Regarding Ar c} , Ar ¹¹ , Ar ¹² , Ar ¹³ , Ar ¹⁴ , Ar ¹⁵ , Ar ¹⁶ , Ar ¹⁷ , and Ar ^{18 in the} formula (1), the substituents when "may be substituted" are used. , Alkyl, aryl, or heteroaryl. As the alkyl, aryl, or heteroaryl, those mentioned above can be cited as "alkyl,""aryl," and "heteroaryl." The number of substituents may be, for example, any number up to the maximum substitutable number, preferably 0 to 3, more preferably 0 to 2, and even more preferably 0 to 1. When there are a plurality of substituents, the plurality of substituents may be bonded to each other. For example, when the hydrogen of methylene in both fluorenyl and benzofluorenyl is substituted with phenyl, these phenyls may be bound to each other in a single bond.

Preferred examples of the "optionally substituted aryl" include groups represented by any of the following formulas (1-X1) to (1-X7).

In the formulas (1-X1) to (1-X7), * indicates a bonding position.
In formulas (1-X1) to (1-X3), Ar ²¹ , Ar ²² , and Ar ²³ independently contain hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, respectively. It is a group represented by benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, anthracenyl, or the formula (A) described later.

In formulas (1-X4) to (1-X7), Ar ²⁴ , Ar ²⁵ , Ar ²⁶ , Ar ²⁷ and Ar ²⁸ are independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, respectively. It is a group represented by chrysenyl, triphenylenyl, pyrenyl, anthracenyl, or the formula (A) described later.

In formulas (1-X1) to (1-X7), if Ar ²¹ , Ar ²² , Ar ²³ , Ar ²⁴ , Ar ²⁵ , Ar ²⁶ , Ar ²⁷ and Ar ²⁸ are anthracenyl, then at least 1 in the anthracenyl. One hydrogen is substituted with phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by the formula (A) described later. May be good.

Further, any one or more hydrogens in each of the groups represented by the formulas (1-X1) to (1-X7) are alkyls having 1 to 6 carbon atoms (preferably methyl or t-butyl). ) May be replaced.

Further, preferred examples of the "optionally substituted aryl" are phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, and a group consisting of groups represented by the formula (A) described below. Included is terphenylyl (particularly m-terphenyl-5'-lyl), which may be substituted with one or more substituents of choice.

Examples of the "optionally substituted heteroaryl" include groups represented by any of the formulas (A), (B), (C), (D), and (E) described later. ..

Further, as the "optionally substituted aryl" or "optionally substituted heteroaryl", a group in which aryl or heteroaryl is bonded to a carbon atom adjacent to the carbon atom at the bonding position of the group is preferable. Take as an example. Specifically, it is a group represented by the following formula (1-XB), and the group represented by the formula (1-X6) is an example of a group represented by the formula (1-XB).

In formula (1-XB), Ar ^B1 is an aryl that may have a substituent or a heteroaryl that may have a substituent, and ^{the benzene ring to which Ar B1} is attached is another aryl ring or hetero. It may be fused with an aryl ring to form a fused ring, Ar ^B2 is an aryl which may have a substituent or a heteroaryl which may have a substituent, and Ar ^B2 is the benzene ring. Alternatively, it is bonded to any of the ring-constituting atoms of the fused ring, n is an integer of 0 to 2, and when n is 2, a plurality of Ar ^B2 may be the same or different. The dotted line shows the skeleton of the aryl ring or the skeleton of the heteroaryl ring that forms a fused ring together with the benzene ring, and * indicates the bonding position of the group represented by the formula (1-XB). In the formula (1-XB), the substituent when "may have a substituent" is aryl or heteroaryl. Formula (1-XB) preferably has at least one fused ring. For example, ^{it is preferable that the benzene ring to which Ar B1} is bonded is fused with another aryl ring or heteroaryl ring to form a fused ring, or Ar ^B1 or one or more Ar ^B2 contains a fused ring. Examples of the fused ring include a naphthalene ring, a phenanthrene ring, a triphenylene ring, and a dibenzofuran ring. Formula (1-XB) preferably has at least one fused ring and n is 1.

For example, Ar ¹⁴ and Ar ¹⁵ are optionally substituted aryls or optionally substituted heteroaryls, and Ar ¹¹ , Ar ¹² , Ar ¹³ , Ar ¹⁶ , Ar ^17, and Ar ¹⁸ are all hydrogen. , Ar ^C , Ar ¹⁴ and Ar ¹⁵ are selected from the group and at least one of which is a group represented by the formula (1-XB) is an anthracene-based compound, which is one of the preferred embodiments. At this time, R ^c is preferably hydrogen.

Specific examples include compounds represented by the following formula numbers in Table 1: (1-124), (1-4133), (1-148), (1-150), (1-136). ), (1-4155), (1-3268), (1-4114), (1-4121), (1-4119), (1-4120), (1-4107), (1-4317), (1-4327), (1-3991), (1-2984), (1-3452), (1-2883) (1-4205), (1-4232), (1-4219), (1-4219) 4254), (1-4263), (1-4271), (1-2995), (1-3005), (1-3020), (1-4204), (1-4198), (1-4280). , (1-3821), (1-3078), (1-4209), (1-4093), (1-4092), (1-2977), (1-4036), (1-4335), ( 1-4347), (1-4354), (1-3751), (1-4368), (1-4372), (1-4334), (1-4330), (1-4106), (1- 3830), (1-3389), (1-4381), (1-4390), (1-3837), (1-3854), (1-4091), (1-3859), (1-4701). , (1-4688), (1-4715), (1-4565), (1-4736), (1-4112).

The anthracene-based compound represented by the formula (1) preferably has a substituent containing an anthracene ring as "optionally substituted aryl" or "optionally substituted heteroaryl".
For example, Ar ¹⁴ and Ar ¹⁵ are optionally substituted aryls or optionally substituted heteroaryls, and Ar ¹¹ , Ar ¹² , Ar ¹³ , Ar ¹⁶ , Ar ^17, and Ar ¹⁸ are all hydrogen. It is also preferable that at least one selected from the group consisting of Ar ^C , Ar ¹⁴ and Ar ^{15 is a group containing an anthracene ring.} At this time, it is preferable that ^{R c is hydrogen.}

The group containing an anthracene ring is anthracenyl which may have a substituent, any of the formulas (1-X1) to (1-X7), and Ar ²¹ , Ar ²² , and Ar 22 in the formula. A group in which Ar ²³ , Ar ²⁴ , Ar ²⁵ , Ar ²⁶ , or Ar ²⁷ and / or Ar ²⁸ is an anthraceneyl which may have a substituent, and a group represented by the formula (A) described later. , ^{One or two selected from the group consisting of R 21 to} R ²⁸ and R ³⁹ is an anthracenyl group which may have a substituent and the like.
Examples of such anthracene-based compounds represented by the formula (1) include compounds represented by any of the following formulas.

In each of the above formulas, X is an aryl or an aryl which may be substituted with an aryl or a heteroaryl, or a heteroaryl which may be substituted with an aryl or a heteroaryl, respectively, and A is independently and simply. Arylene optionally substituted with a bond, aryl or heteroaryl or heteroarylene optionally substituted with aryl or heteroaryl. Here, the aryl and heteroaryl may refer respectively to the description of aryl and heteroaryl in Ar ^c and the like of the formula (1).

Preferred examples of the aryl in X of each of the above formulas include phenyl, 1-naphthyl, 2-naphthyl and the like, and preferred examples of the heteroaryl include a group represented by the formula (A). X is preferably an unsubstituted aryl or an unsubstituted heteroaryl, and when it has a substituent, it is preferably substituted with 1 or 2 phenyls.

Arylene of A in the above formulas, The heteroarylene, be mentioned in the formula (1), one of the divalent groups obtained by removing hydrogen in groups each described as aryl and heteroaryl in Ar ^c, etc. Can be done. Preferred groups are 1,3-phenylene, 1,4-phenylene, 1,6-naphthylene, 2,5-naphthylene, 2,6-naphthylene, 2,7-naphthylene, and a group represented by the formula (A). Examples thereof include a divalent group obtained by removing any of the hydrogens in the above. A is preferably an unsubstituted arylene or an unsubstituted heteroarylene, and when it has a substituent, it is preferably substituted with 1 or 2 phenyls.

Specific examples include compounds represented by the following formula numbers in Table 1: (1-2495), (1-2404), (1-2440), (1-2499), (1-2413). , (1-2516), (1-2519), (1-2525), (1-2541), (1-2557), (1-2573), (1-2586), (1-2694), (1-2599), (1-2728), (1-2579), (1-2696), (1-2738), (1-2743), (1-2699), (1-2756), (1 -2627), (1-2757), (1-2686), (1-2615), (1-2640), (1-2747), (1-2641), (1-2775), (1-2779). ), (1-2787), (1-2776), (1-2812), (1-3914), (1-3951), (1-3903), (1-2416), (1-2520), (1-2603), (1-3953), (1-3875).

In addition, specific examples of the "optionally substituted aryl" and the "optionally substituted heteroaryl" include each substituent represented by the structural formula described later as an explanation of the symbols in Table 1.

At least one hydrogen in the compound represented by the formula (1) may be substituted with halogen, cyano, or deuterium. Examples of the "halogen" in this case include fluorine, chlorine, bromine, and iodine. In particular, a compound in which all hydrogen in the compound represented by the formula (1) is replaced with deuterium is preferable.

The ^{formula in which Ar 14} and Ar ¹⁵ are optionally substituted aryls or optionally substituted heteroaryls, and Ar ¹¹ , Ar ¹² , Ar ¹³ , Ar ¹⁶ , Ar ^17, and Ar ¹⁸ are all hydrogens ( Among the compounds represented by 1), a compound in which at least one hydrogen is replaced with deuterium is preferable. At this time, the substitution position of deuterium is not limited. For example, ^{a compound in which at least R c} is deuterium, a compound in which at least one hydrogen selected from the group consisting of ^{Ar c} and Ar ^{11 to} Ar ^{18 is replaced with deuterium, or all hydrogen.} Examples include compounds in which deuterium is substituted.

In formula (1), ^Rc is hydrogen, alkyl, or cycloalkyl, preferably hydrogen, methyl, or t-butyl, and more preferably hydrogen.

On the other hand, Ar ¹⁴ and Ar ¹⁵ are optionally substituted aryls or optionally substituted heteroaryls, and Ar ¹¹ , Ar ¹² , Ar ¹³ , Ar ¹⁶ , Ar ^17, and Ar ¹⁸ are all hydrogens. Occasionally, ^{anthracene-based compounds in which R c} is alkyl or cycloalkyl can also be mentioned as a preferred example. Specific examples include compounds represented by the following formula numbers in Table 1: (1-4434), (1-4429), (1-4458), (1-4409), (1-4404). ), (1-4427).

In formula (1), at least two of Ars ^{11 to 18} are preferably aryls that may be substituted or heteroaryls that may be substituted. That is, in the anthracene-based compound represented by the formula (1), at least three substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl are bonded to the anthracene ring. It is preferable to have a structure.

The anthracene-based compound represented by the formula (1) ^{is an aryl in which two of Ar 11 to} Ar ¹⁸ may be substituted or a heteroaryl which may be substituted, and the other six are hydrogen and substituted. More preferably, it is an alkyl which may be substituted, a cycloalkyl which may be substituted, an alkenyl which may be substituted, or an alkoxy which may be substituted. That is, the anthracene-based compound represented by the formula (1) has a structure in which three substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl are bonded to the anthracene ring. It is more preferable to have.

The anthracene-based compound represented by the formula (1) ^{is an aryl in which any two of Ar 11 to} Ar ¹⁸ may be substituted or a heteroaryl which may be substituted, and the other six are hydrogen, methyl, and Alternatively, it is more preferably t-butyl. Any two of Ars ^{11 to Ar 18} are optionally substituted aryls or optionally substituted heteroaryls, R ^c is hydrogen, and the other six of Ars ^{11 to Ar 18 are hydrogens.} Is particularly preferred.

As a preferable range of the anthracene-based compound represented by the formula (1), the anthracene-based compound represented by the following formula (1A), formula (1B), formula (1C), formula (1D), or formula (1E) is used. It can also be defined.

In Equation (1A), Equation (1B), Equation (1C), Equation (1D) and Equation (1E), Ar ^c ', Ar ¹¹ ', Ar ¹² ', Ar ¹³ ', Ar ¹⁴ ', Ar ¹⁵ ', Ar ¹⁷ ', and ^{Ar 18'} are each independently phenyl, biphenylyl, terphenylyl, quaterphenylene phenylene Lil, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or, below formula (a) The group represented by, and at least one hydrogen in these groups is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or described below. It may be substituted with a group represented by the formula (A). Here, when the hydrogen of methylene in fluorenyl and benzofluorenyl are both substituted with phenyl, these phenyls may be bonded to each other in a single bond. ^{Ar c ', Ar 11',} Ar 12 ', Ar 13', Ar 14 ', Ar 15', Ar 17 ', and ^{Ar 18'} is to the carbon atom of the anthracene ring which is not bound methyl instead of hydrogen or t-Butyl may be bonded.

^{Ar c ', Ar 11',} Ar 12 ', Ar 13', Ar 14 ', Ar 15', the ^{Ar 17} ', and ^{Ar 18',} are each a substituted or unsubstituted phenyl or substituted or unsubstituted naphthyl In some cases, it is preferable that the group is represented by any of the above formulas (1-X1) to (1-X7).

^{Ar c ', Ar 11',} Ar 12 ', Ar 13', Ar 14 ', Ar 15', Ar 17 ', and ^{Ar 18'} are each independently phenyl, biphenylyl (especially, biphenyl-2-yl or biphenyl -4-yl), terphenylyl (particularly m-terphenyl-5'-lyl), naphthyl, phenanthryl, fluorenyl, or represented by any of the formulas (A-1) to (A-4) described below. At least one hydrogen in these groups is phenyl, biphenylyl, naphthyl, phenanthryl, fluorenyl, or of the formulas (A-1) to (A-4) described below. It may be substituted with a group represented by either.

Further, at least one hydrogen in the compound represented by the formula (1A), (1B), (1C), (1D), or (1E) may be substituted with halogen, cyano, or deuterium.

Hereinafter, the group represented by the above formula (A) will be described.

In formula (A), Y is -O-, -S-, or> N-R ³⁹ . R ³⁹ is hydrogen or an optionally substituted aryl. Further, in the formula (A), R ^{21 to} R ²⁸ are independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, and substituted. Heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, It may be substituted amino, halogen, hydroxy or cyano, and ^{adjacent groups of R 21 to} R ²⁸ may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. Further, at least one hydrogen in the formed hydrocarbon ring, aryl ring or heteroaryl ring is an alkyl which may be substituted, a cycloalkyl which may be substituted, an aryl which may be substituted, or an aryl. May be heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl. , May be substituted. May be substituted with amino, halogen, hydroxy, or cyano.
The group represented by the formula (A) is a group obtained by removing one hydrogen at any position of the formula (A), and * indicates the position.

^{Of R 21 to} R ²⁸ in the formula (A), it is preferable that all of them are hydrogen, or at least one of them is an aryl which may be substituted or a heteroaryl which may be substituted, and all of them are preferable. It is more preferably hydrogen, or at least one optionally substituted aryl or optionally substituted heteroaryl, and the other hydrogen, all of which are hydrogen, or either. It is more preferred that one or two are optionally substituted aryl or optionally substituted heteroaryl, and the others are hydrogen. When ^{adjacent groups of R 21 to} R ²⁸ are bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring, the hydrogen in the formed ring is not substituted with a substituent and the rest. R ^21- R ²⁸ may be hydrogen, or at least one of the substituents substituting hydrogen in the formed ring and the remaining R ^21- R ²⁸ may be substituted aryl or substituted. It is preferably heteroaryl, the hydrogen in the formed ring is not substituted with a substituent, and the remaining R ^21- R ²⁸ are hydrogen, or a substituent that substitutes for hydrogen in the formed ring. And it is more preferred that one or two of the remaining R ^21- R ^{28 are optionally substituted aryl or optionally substituted heteroaryl.}

^{The "alkyl" of the "optionally substituted alkyl" in R 21 to} R ²⁸ in the formula (A) may be either a straight chain or a branched chain, for example, a linear alkyl having 1 to 24 carbon atoms or a straight chain alkyl having 1 to 24 carbon atoms. Branched chain alkyls having 3 to 24 carbon atoms can be mentioned. An alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms) is preferable, an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms) is more preferable, and an alkyl having 1 to 6 carbon atoms is more preferable. (Branched chain alkyl having 3 to 6 carbon atoms) is more preferable, and alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms) is particularly preferable.

Specific "alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1 -Methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2 -Propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, Examples thereof include n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl and n-eicocil.

^{Examples of the "aryl" of the "optionally substituted aryl" in R 21 to} R ²⁸ in the formula (A) include aryls having 6 to 30 carbon atoms, and aryls having 6 to 16 carbon atoms are preferable. , Aryl having 6 to 12 carbon atoms is more preferable, and aryl having 6 to 10 carbon atoms is particularly preferable.

Specific examples of "aryl" include phenyl, which is a monocyclic system, biphenylyl, which is a bicyclic system, naphthyl, which is a condensed bicyclic system, and terfenylyl, which is a tricyclic system (m-terphenylyl, o-terphenylyl, p-terphenylyl). , Condensed tricyclics such as anthracenyl, acenaphthylenyl, fluorenyl, phenylenyl, phenanthrenyl, condensed tetracyclics triphenylenyl, pyrenyl, naphthalenyl, benzofluorenyl, condensed pentacyclics perylenyl, pentasenyl and the like.

^{Examples of the "heteroaryl" of the "optionally substituted heteroaryl" in R 21 to} R ²⁸ in the formula (A) include heteroaryl having 2 to 30 carbon atoms and having 2 to 25 carbon atoms. Heteroaryl is preferable, heteroaryl having 2 to 20 carbon atoms is more preferable, heteroaryl having 2 to 15 carbon atoms is further preferable, and heteroaryl having 2 to 10 carbon atoms is particularly preferable. Examples of the heteroaryl include a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

Specific "heteroaryl" includes, for example, pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indrill, isoindrill, 1H-. Indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, synnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyldinyl, prynyl, pteridinyl, carbazolyl, acridinyl, phenoxatinyl, phenoxadinyl, phenoxadinyl Examples thereof include phenazinyl, indolidinyl, frill, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzo [b] thienyl, dibenzothienyl, frazanyl, thiantrenyl, naphthobenzofuranyl and naphthobenzothienyl.

^{As the "alkoxy" of the "optionally substituted alkoxy" in R 21 to} R ²⁸ in the formula (A), for example, a straight-chain alkoxy having 1 to 24 carbon atoms or a branched-chain alkoxy having 3 to 24 carbon atoms is used. can give. Alkoxy having 1 to 18 carbon atoms (alkoxy of branched chains having 3 to 18 carbon atoms) is preferable, and alkoxy having 1 to 12 carbon atoms (alkoxy of branched chains having 3 to 12 carbon atoms) is more preferable, and alkoxy having 1 to 6 carbon atoms is more preferable. Alkoxy (alkoxy of a branched chain having 3 to 6 carbon atoms) is more preferable, and alkoxy having 1 to 4 carbon atoms (alkoxy of a branched chain having 3 to 4 carbon atoms) is particularly preferable.

Specific examples of "alkoxy" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy and the like.

^{The "aryloxy" of the "optionally substituted aryloxy" in R 21 to} R ²⁸ in the formula (A) is a group in which the hydrogen of the -OH group is substituted with an aryl, and this aryl is described above. The groups described as "aryl" in ^{R 21-} R ^{28 can be cited.}

^{The "arylthio" of the "optionally substituted arylthio" in R 21 to} R ²⁸ in the formula (A) is a group in which the hydrogen of the -SH group is substituted with an aryl, and this aryl is the above-mentioned R ^21. The group described as "aryl" in ~ R ^{28 can be cited.}

Examples ^{of the "trialkylsilyl" in R 21 to R 28} in the formula (A) include groups in which each of the three hydrogens in the silyl is independently substituted with an alkyl, and this alkyl is the above-mentioned R ^{21 to} R ^28. The group described as "alkyl" in. Preferred alkyls for substitution are alkyls having 1 to 4 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, n-butyl, s-butyl, t-butyl, cyclobutyl and the like.

Specific "trialkylsilyl" includes trimethylsilyl, triethylsilyl, tripropylsilyl, trii-propylsilyl, tributylsilyl, tris-butylsilyl, trit-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyl. Dimethylsilyl, butyldimethylsilyl, s-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, s-butyldiethylsilyl, t-butyldiethylsilyl, methyl Dipropyl silyl, ethyl dipropyl silyl, butyl dipropyl silyl, s-butyl dipropyl silyl, t-butyl dipropyl silyl, methyl di-propyl silyl, ethyl di-propyl silyl, butyl di-propyl silyl, s-butyl di i -Propylsilyl, t-butyldii-propylsilyl and the like can be mentioned.

Examples of the "substituted amino" of the "optionally substituted amino" in ^{R 21 to} R ²⁸ in the formula (A) include aminos in which two hydrogens are substituted with aryl or heteroaryl. Aminos in which two hydrogens are substituted with aryls are diaryl substituted aminos, aminos in which two hydrogens are substituted with heteroaryls are diheteroaryl substituted aminos, and aminos in which two hydrogens are substituted with aryls and heteroaryls. Is an aryl heteroaryl substituted amino. As the aryl or heteroaryl, the groups described as "aryl" or "heteroaryl" in ^{R 21 to} R ^{28 described above can be cited.}

Specific examples of the "substituted amino" include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino and the like.

^{Examples of the "halogen" in R 21 to} R ²⁸ in the formula (A) include fluorine, chlorine, bromine and iodine.

^{Among the groups described as R 21 to} R ²⁸ in the formula (A), some may be substituted as described above, and examples of the substituent in this case include alkyl, aryl or heteroaryl. The alkyl, aryl or heteroaryl can be cited as the groups described above as "alkyl,""aryl" or "heteroaryl" in ^{R 21-} R ^28.

R ³⁹ in the "> N-R ^39" as Y in formula (A) is hydrogen or aryl which may be substituted, described as "aryl" in R ²¹ to R ²⁸ described above as the aryl A group can be cited, and as the substituent, the group described as a substituent for ^{R 21 to} R ^{28 can be cited.}

^{Adjacent groups of R 21 to} R ²⁸ in the formula (A) may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring. The case where the ring is not formed is the group represented by the following formula (A-1), and the case where the ring is formed is, for example, the group represented by the following formulas (A-2) to (A-14). Be done. At least one hydrogen in the group represented by any of the formulas (A-1) to (A-14) is alkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, diaryl substituted amino. , Diheteroaryl substituted amino, aryl heteroaryl substituted amino, halogen, hydroxy or cyano may be substituted, and these can be cited as the groups described as the respective groups in ^{R 21 to} R ^{28 described above.}

Examples of the ring formed by bonding adjacent groups to each other include a cyclohexane ring in the case of a hydrocarbon ring, and "aryl" and "hetero" in ^{R 21 to} R ^{28 described above in the case of an aryl ring or a heteroaryl ring.} The ring structures described in "Aryl" are mentioned, and these rings are formed so as to condense with one or two benzene rings in the formula (A-1).

Examples of the group represented by the formula (A) include groups represented by any of the following formulas (A-1) to (A-14), and formulas (A-1) to (A-). The group represented by any one of the formulas (A-1) to (A-4) is preferable, and the group represented by any of the formulas (A-1) to (A-4) is more preferable. ) And the group represented by the formula (A-4) are more preferable, and the group represented by the formula (A-1) is most preferable.

The group represented by the formula (A) is a group obtained by removing one hydrogen at any position of the formula (A), and * indicates the position. That is, the group represented by the formula (A) may have any position as the bonding position. Among them, any carbon atom on the two benzene rings in the structure of the formula (A), or any of R ^{21 to} R ^{28 in} the structure of the formula (A) formed by bonding adjacent groups to each other. It is preferable that it is an atom on the ring of the above, or a group that directly bonds with N (they have a bond) ^{in "> N-R 39} " as Y in the structure of the formula (A).

It is preferable that Y in the formula (A) and Y in each of the formulas (A-1) to (A-14) are −O−.

Examples of the group represented by the formula (A) include a group represented by the following formula. Y and * in the formula have the same definitions as above, and Y is preferably −O−.

A compound containing a group represented by the formula (A) (particularly, a group represented by the formula (A) in which Y is −O−) is given as a preferable example of the anthracene-based compound represented by the formula (1). In addition to the compounds already described, the following anthracene compounds (a) or (b) are also preferable.

(A) In formula (1), Ar ¹⁴ and Ar ¹⁵ are optionally substituted aryls or optionally substituted heteroaryls, Ar ¹¹ , Ar ¹² , Ar ¹³ , Ar ¹⁶ , Ar ^17, and Ar. ¹⁸ is all hydrogen, and ^{at least one selected from the group consisting of Ar C} , Ar ¹⁴ and Ar ¹⁵ is a group represented by the formula (A), and R ^{21 to} R ²⁸ in the formula (A) and An anthracene-based compound in which at least one selected from the group consisting of R ³⁹ when Y is> N-R ^{39 is aryl or heteroaryl.} R ^c is preferably hydrogen.

Specific examples include compounds represented by the following formula numbers in Table 1: (1-3445), (1-3467), (1-3434), (1-3481), (1-3408). ), (1-3777), (1-3594), (1-3589), (1-3440), (1-3435), (1-3572), (1-3453), (1-3562), (1-3559), (1-3522), (1-4014), (1-4018), (1-3762), (1-4145), (1-4573), (1-4579), (1 -3444), (1-3450), (1-4747).

(B) In formula (1), Ar ¹⁴ and Ar ¹⁵ are optionally substituted aryls or optionally substituted heteroaryls, Ar ¹¹ , Ar ¹² , Ar ¹³ , Ar ¹⁶ , Ar ^17, and Ar. ¹⁸ is all hydrogen, and ^{at least one selected from the group consisting of Ar C} , Ar ¹⁴ and Ar ¹⁵ has an aryl group represented by the formula (A) as a substituent or is represented by the formula (A). Anthracene-based compound that is a heteroaryl having a group as a substituent. R ^c is preferably hydrogen. An example of an aryl having a group represented by the formula (A) as a substituent is a group represented by any of the formulas (1-X1) to (1-X6) and Ar in the formula. ^{Examples thereof include a group in which 21} , Ar ²² , Ar ²³ , Ar ²⁴ , Ar ²⁵ , or Ar ²⁶ is a group represented by the formula (A).

Specific examples include compounds represented by the following formula numbers in Table 1: (1-2912) (1-3284), (1-3736), (1-3770), (1-2873). , (1-3249), (1-3296), (1-2917), (1-3768), (1-3780), (1-3963), (1-4112), (1-4052), ( 1-4847), (1-3778), (1-4168), (1-4510).

Hereinafter, the group represented by the above-mentioned formula (B), the group represented by the formula (C), the group represented by the formula (D), and the group represented by the formula (E) will be described. For the following description of each substituent, the description of R ^{21 to} R ²⁸ of the formula (A) can be referred to.

In formula (B), Y is -O-, -S- or> N-R ³⁹ . R ³⁹ is hydrogen or an optionally substituted aryl. Further, in the formula (B), R ^{29 to} R ³⁸ are independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, and optionally substituted, respectively. Good heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, substituted It may be amino, halogen, hydroxy or cyano, and ^{adjacent groups of R 29 to} R ³⁸ may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring. Further, at least one hydrogen in the formed hydrocarbon ring, aryl ring or heteroaryl ring is an alkyl which may be substituted, a cycloalkyl which may be substituted, an aryl which may be substituted, or an aryl. May be heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl. , May be substituted. May be substituted with amino, halogen, hydroxy, or cyano. The group represented by the formula (B) is a group obtained by removing one hydrogen at any position of the formula (B), and * indicates the position.

In formula (B), Y is preferably −O−.
^{Of R 29 to} R ³⁸ in the formula (B), it is preferable that all of them are hydrogen, or at least one of them is an aryl which may be substituted or a heteroaryl which may be substituted, and all of them are preferable. It is more preferably hydrogen, or at least one optionally substituted aryl or optionally substituted heteroaryl, and the other hydrogen, all of which are hydrogen, or either. It is more preferred that one or two are optionally substituted aryl or optionally substituted heteroaryl, and the others are hydrogen. When ^{adjacent groups of R 29 to} R ³⁸ are bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring, the hydrogen in the formed ring is not substituted with a substituent and the rest. R ^29- R ³⁸ is a hydrogen, or at least one of the substituents substituting the hydrogen in the formed ring and the remaining R ^29- R ³⁸ may be substituted aryl or substituted. It is preferably heteroaryl, the hydrogen in the formed ring is not substituted with a substituent, and the remaining R ^29- R ³⁸ are hydrogen, or a substituent that substitutes for hydrogen in the formed ring. And it is more preferred that one or two of the remaining R ^29- R ^{38 are optionally substituted aryl or optionally substituted heteroaryl.}

Examples of the group represented by the formula (B) include a group represented by the following formula (B-1).

As a group represented by the formula (B). More specifically, a group represented by the following formula can be given as an example. Y and * in the formula have the same definitions as above, and Y is preferably −O−.

In formula (C), Y is -O-, -S-, or> N-R ³⁹ . R ³⁹ is hydrogen or an optionally substituted aryl. Further, in the formula (C), R ^{41 to} R ⁴⁸ are independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, and substituted. Heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, It may be substituted amino, halogen, hydroxy or cyano, and ^{adjacent groups of R 41 to} R ⁴⁸ may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. Further, at least one hydrogen in the formed hydrocarbon ring, aryl ring or heteroaryl ring is an alkyl which may be substituted, a cycloalkyl which may be substituted, an aryl which may be substituted, or an aryl. May be heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl. , May be substituted. May be substituted with amino, halogen, hydroxy, or cyano.

The group represented by the formula (C) is a group obtained by removing one hydrogen at any position of the formula (C), and * indicates the position.
In formula (C), when Y is> N-R ³⁹ , R ³⁹ is preferably a optionally substituted phenyl, more preferably an unsubstituted phenyl. The optionally substituted phenyl that is ^{R 39} may be attached to the benzene ring with ^{R 42} , R ⁴³ , R ⁴⁶ , or R ^{47 as the bond.} It is preferable that at least one Y is -O-, and either Y is -O-, or one Y is -O- and the other is> N-R ^39. preferable. It is preferable that all of R ^{41 to} R ^{48 are hydrogen.}

Examples of the group represented by the formula (C) include a group represented by the following formula (C-1).

As a group represented by the formula (C). More specifically, a group represented by the following formula can be given as an example. Y and * in the formula have the same definitions as above, and Y is preferably −O−.

In formula (D), Y is -O-, -S-, or> N-R ³⁹ . R ³⁹ is hydrogen or an optionally substituted aryl. Further, in the formula (D), R ^{51 to} R ⁵⁸ are independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, and substituted. Heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, It may be substituted amino, halogen, hydroxy or cyano, and ^{adjacent groups of R 51 to} R ⁵⁸ may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. Further, at least one hydrogen in the formed hydrocarbon ring, aryl ring or heteroaryl ring is an alkyl which may be substituted, a cycloalkyl which may be substituted, an aryl which may be substituted, or an aryl. May be heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl. , May be substituted. May be substituted with amino, halogen, hydroxy, or cyano.

The group represented by the formula (D) is a group obtained by removing one hydrogen at any position of the formula (D), and * indicates the position.
In formula (D), Y is preferably −O−. It is preferable that all of R ^{51 to} R ^{58 are hydrogen.}

In formula (E), Y is -O-, -S-, or> N-R ³⁹ . R ³⁹ is hydrogen or an optionally substituted aryl. Further, in the formula (E), R ^{61 to} R ⁷¹ are independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, and substituted. Heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, It may be substituted amino, halogen, hydroxy or cyano, and ^{adjacent groups of R 61 to} R ⁷¹ may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. Further, at least one hydrogen in the formed hydrocarbon ring, aryl ring or heteroaryl ring is an alkyl which may be substituted, a cycloalkyl which may be substituted, an aryl which may be substituted, or an aryl. May be heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl. , May be substituted. May be substituted with amino, halogen, hydroxy, or cyano.

The group represented by the formula (E) is a group obtained by removing one hydrogen at any position of the formula (E), and * indicates the position.
In formula (E), when Y is> N-R ³⁹ , R ³⁹ is preferably a optionally substituted phenyl, more preferably an unsubstituted phenyl. The optionally substituted phenyl that is ^{R 39} may be attached to the benzene ring with ^{R 61} , R ⁶² , R ⁶⁹ , or R ^{70 as the bond.} It is preferable that at least one of Y is −O−, and it is more preferable that all of them are −O−. R ^{61 to} R ⁷¹ are preferably hydrogen, phenyl, biphenyl, or naphthyl, and more preferably hydrogen.

As a particularly preferable anthracene-based compound represented by the formula (1), an anthracene-based compound represented by the following formula (1Aa) can be mentioned.

Wherein ^{(1Aa), Ar c ',} Ar 14', and ^{Ar 15} 'are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or the above formulas, It is a group represented by any of (A-1) to (A-11), and at least one hydrogen in these groups is phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, It may be substituted with chrysenyl, triphenylenyl, pyrenyl, or a group represented by any of formulas (A-1) to (A-11). Here, when the hydrogen of methylene in fluorenyl and benzofluorenyl are both substituted with phenyl, these phenyls may be bonded to each other in a single bond. ^{Further, Ar c ', Ar 14'} , and Ar 15 ^'are the carbon atoms on the anthracene ring which is not bound methyl or t- butyl instead of hydrogen may be substituted. At least one hydrogen in the compound represented by the formula (1Aa) may be substituted with halogen or cyano, and at least one hydrogen in the compound represented by the formula (1Aa) is substituted with deuterium.

Wherein ^{(1Aa), Ar c ',} Ar 14', and ^{Ar 15} 'each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl or above equation, (A-1) ~ formula (A-4) The group represented by any of the above is preferable, and at least one hydrogen in these groups is phenyl, naphthyl, phenanthryl, fluorenyl, or any of formulas (A-1) to (A-4). It may be substituted with the represented group.

In the compound represented by the formula (1Aa), at least, it is preferable that the hydrogen bonded to the carbon of 10-position of the anthracene ring (Ar c ^'is a carbon position 9 binding) are replaced with deuterium .. That is, the compound represented by the formula (1Aa) is preferably a compound represented by the following formula (1Ab). In the formula (1Ab), D is ^{deuterium, Ar c ', Ar 14'} , and ^{Ar 15} 'are the same as defined in formula (1Aa). D in the formula (1Ab) indicates that at least this position is deuterium, and any one or more other hydrogens in the formula (1Aa) may be deuterium at the same time, and the hydrogen in the formula (1Aa) is deuterium. It is also preferable that both are deuterium.

The compounds represented by the formulas (1-1) to (1-5179), which are specific examples of the compounds represented by the formula (1), are shown in Table 1 below. However, the present invention is not limited by the disclosure of these specific structures. In Table 1, D indicates deuterium, Me indicates methyl, tBu indicates t-butyl, CyHex indicates cyclohexyl, and other symbols will be described later.

The substituents represented by the symbols used in Table 1 are shown below. When a symbol in which Y of the symbol attached to the structural formula of the substituent shown below is O is listed in Table 1, a substituent in which -Y- is -O- in the structural formula (for example, HCO-1) is represented, and when the symbol in which Y is S is shown in Table 1, it represents a substituent (for example, HCS-1) in which −Y− is −S− in the structural formula, and Y When the symbol in which is N is shown in Table 1, -Y- in the structural formula represents a substituent (for example, HCN-1) in which> N-Ph (Ph is phenyl). Further, when the symbol in which Z of the symbol attached to the structural formula of the substituent shown below is O is listed in Table 1, -Z- in the structural formula is -O-. For example, it represents DHCO-1), and when the symbol in which Z is S is shown in Table 1, it represents a substituent (for example, DHCS-1) in which -Z- is -S- in the structural formula. When the symbol in which Z is N is shown in Table 1, it represents a substituent (for example, DHCN-1) in which _{-Z- in the structural formula is> NC 6} D _5. Further, in the following structural formula, D is deuterium, Me is methyl, tBu is t-butyl, and * is the bond position.

Among the above compounds, compounds represented by the following formulas are preferable. In the following formula, D is deuterium, Me is methyl, tBu is t-butyl, and CyHex is cyclohexyl.

1-1-2. Method for Producing Anthracene Compound The anthracene compound represented by the formula (1) is described in International Publication No. 2006/003842, Korean Publication No. 2017-116885, International Publication No. 2009/142230 and the like. It can be manufactured by a method similar to the manufacturing method.

1-2-1. Polycyclic aromatic compound represented by the formula (2) and its multimer The organic EL element of the present invention has a polycyclic aromatic compound represented by the following formula (2) and the formula (2) as a dopant material for the light emitting layer. ) Contains a multimer of a polycyclic aromatic compound having a plurality of structures represented by). The polycyclic aromatic compound is preferably of the following formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-e). A polycyclic aromatic compound represented by 2-f), or the following formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e). , Or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the formula (2-f).

In each structural formula, "A" to "C" and "a" to "c" are symbols indicating a ring structure represented by a ring, a benzene ring, or a 5-membered ring, respectively, and other symbols are the definitions described above. Is the same as.

The A ring, B ring, and C ring in the formula (2) are independently aryl rings or heteroaryl rings, and at least one hydrogen in these rings may be substituted with a substituent. The substituents are substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted aryl heteroarylamino (with aryl). Amino with heteroaryl), substituted or unsubstituted diarylboryl (two aryls may be attached via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, Substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl is preferable. Examples of the substituent when these groups have a substituent include aryl, heteroaryl, alkyl, cycloalkyl, and substituted silyl.

The A ring, B ring, and C ring in the formula (2) are independently aryl rings or heteroaryl rings, respectively. At least one hydrogen in these rings may be substituted with a substituent.

At least one of the A ring, the B ring, and the C ring is preferably an aryl ring having at least one substituent or a heteroaryl ring having at least one substituent, and is preferably an A ring, a B ring, and a C ring. It is more preferable that each of the above is an aryl ring having at least one substituent or a heteroaryl ring having at least one substituent, and an aryl ring or an aryl ring in which each of the A ring, the B ring, and the C ring has one substituent. More preferably, it is a heteroaryl ring having one substituent.

The substituents at this time include substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, and substituted or unsubstituted aryl heteroarylamino. (Aryl with aryl and heteroaryl), substituted or unsubstituted diarylboryl (two aryls may be attached via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted. Cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl are preferred. Examples of the substituent when these groups have a substituent include aryl, heteroaryl, alkyl, cycloalkyl, diarylamino, and substituted silyl.

In particular, as the substituent, substituted or unsubstituted alkyl (particularly neopentyl) and cycloalkyl such as adamantyl are preferable. Further, tertiary-alkyl (tR) is preferable. This is because such a bulky substituent prevents deactivation due to aggregation of molecules and improves the emission quantum yield (PLQY). Further, as the substituent, a substituted or unsubstituted diarylamino is also preferable.

The tertiary alkyl is represented by the following formula (tR).

In formula (tR), ^Ra , R ^b , and R ^c are independently alkyls having 1 to 24 carbon atoms, and any −CH _{2− in the} alkyl may be substituted with −O−. , The group represented by the formula (tR) is replaced with at least one hydrogen in the compound or structure represented by the formula (2) in *.

The "alkyl having 1 to 24 carbon atoms" of R ^a , R ^b , and R ^c may be either a straight chain or a branched chain, for example, a linear alkyl having 1 to 24 carbon atoms or a linear alkyl having 3 to 24 carbon atoms. Branched chain alkyl, alkyl with 1 to 18 carbon atoms (branched chain alkyl with 3 to 18 carbon atoms), alkyl with 1 to 12 carbon atoms (branched chain alkyl with 3 to 12 carbon atoms), alkyl with 1 to 6 carbon atoms (branched chain alkyl) Examples thereof include a branched chain alkyl having 3 to 6 carbon atoms and an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms).

^{The total number of carbon atoms of Ra} , R ^b , and R ^c in the formula (tR) of the formula (2) is preferably 3 to 20 carbon atoms, and particularly preferably 3 to 10 carbon atoms.

Specific alkyls of R ^a , R ^b , and R ^c include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t. -Pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1- Methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, Examples thereof include 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl and n-eicosyl.

Examples of the group represented by the formula (tR) include t-butyl, t-amyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-. Methylbutyl, 1,1,3,3-tetramethylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1- Dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1- Methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl- Examples thereof include 1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl and 1,1-dimethylhexyl groups. Of these, t-butyl and t-amyl are preferred.

Other preferred examples of substituents on the A, B, and C rings are, for example, diarylamino substituted with a group of formula (tR), carbazolyl substituted with a group of formula (tR) or carbazolyl substituted with a group of formula (tR) or tR. ) Substituted with a group of benzocarbazolyl. Examples of the "diarylamino" include groups described below as the "first substituent". As a form of substitution of a group of the formula (tR) with diarylamino, carbazolyl and benzocarbazolyl, a part or all of hydrogen of the aryl ring or the benzene ring in these groups was substituted with the group of the formula (tR). For example.

The aryl ring or heteroaryl ring in the A ring, B ring and C ring shares a bond with the condensed bicyclic structure in the center of the formula (2) composed of ^{"B", "X 1} " and "X ^{2" 5} It preferably has a membered ring or a 6-membered ring.

Here, the "condensed two-ring structure" means that two saturated hydrocarbon rings ^{including "B", "X 1} " and "X ^{2" shown in the center of the formula (2) are condensed.} Means structure. The "6-membered ring sharing a bond with the condensed two-ring structure" is, for example, the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), and the formula (2-d). 2-e) and a ring (benzene ring (6-membered ring)) condensed into the condensed two-ring structure as shown by the formula (2-f). Further, "the aryl ring (which is the A ring) or the heteroaryl ring has the 6-membered ring" means that the A-ring is formed only by the 6-membered ring or includes the 6-membered ring. This means that another ring or the like is further condensed with this 6-membered ring to form an A ring. In other words, the "aryl ring having a 6-membered ring (which is an A ring) or a heteroaryl ring" as used herein means that a 6-membered ring constituting all or a part of the A ring is condensed into the condensed two-ring structure. It means that you are doing it. The same explanation applies to the "5-membered ring". Further, the same description applies to "B ring (b ring)" and "C ring (c ring)".

The A ring in the formula (2) is the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e), and the formula (2-). corresponding to a ring and substituents thereof ^R 1 to R ³ in f). The B ring in the formula (2) is the b ring in the formula (2-a), the formula (2-b), and the formula (2-c) and its substituents R ^{8 to} R ¹¹ , formula (2-d). b rings in its substituents ^{R 10} and ^{R 11,} as well as the formula (2-e), and the corresponding b ring in the formula (2-f) and their substituents ^{R 8} and ^{R 9.} Wherein C ring in the (2), the formula (2-a) c rings in its substituents ^R 4 to R ^7, wherein (2-b), formula (2-d), and the formula (2-f) c ring in its substituents ^{R 4} and ^{R 5,} and corresponds to the c ring and substituents thereof ^{R 6} and ^{R 7} in the formula (2-c) and formula (2-e). That is, the formula (2-a) corresponds to a structure in which a ring having at least a 6-membered ring structure is selected as the A to C rings of the formula (2), and the formula (2-b) and the formula (2-c) correspond to the structure. ), Formula (2-d), Formula (2-e), and Formula (2-f) each have a ring having at least a 6-membered ring structure and a ring having at least a 5-membered ring structure as the A to C rings of the formula (2). The ring it has corresponds to the selected structure. In that sense, each ring in the formula (2-a) and the like is represented by lowercase letters a to c.

_XX in Eqs. (2-b), Eq. (2-c), Eq. (2-d), Eq. (2-e), and Eq. (2-f) are independently>O,> S, respectively. ,> N-R, or> C (-R) ₂ . Here, R of> N-R is an aryl which may be substituted, a heteroaryl which may be substituted, an alkyl which may be substituted, or a cycloalkyl which may be substituted, and is substituted. It is preferably an aryl, which may be optionally, and more preferably an unsubstituted aryl. Further, the R of> C (-R) ₂ is independently substituted with an aryl, alkyl or cycloalkyl which may be substituted with hydrogen, alkyl or cycloalkyl, or a heteroaryl, alkyl, which may be substituted with an alkyl or cycloalkyl, respectively. Alternatively, it is cycloalkyl, preferably alkyl, and more preferably methyl. > It is preferable that the two Rs in C (−R) _{2 are the same.} It is also preferable that the two Rs at> C (−R) _{2 form a ring with each other.}
X _X is independently,>O,> S preferably, or> is N-R,> O or> more preferably from S,, further preferably> S.

In formulas (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f), R ^{1 to} R ¹¹ are , Independently, hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl , Cycloalkyl, alkoxy, aryloxy, or substituted silyls, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyls.

R ^{1 to} R ¹¹ are independently hydrogen, alkyl (particularly, tertiary-alkyl (tR), neopentyl, etc.), cycloalkyl (eg, adamantyl, etc.), substituted or unsubstituted diarylamino, or substituted silyl. (Triphenylsilyl, trimethylsilyl, etc.) is preferable.

^{In R 1 to} R ³ in each of the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e), and the formula (2-f). , 0 to 1 are other than hydrogen (special above-mentioned preferable substituent), and others are hydrogen, and ^{0 to 1 out of R 4 to} R ⁷ are other than hydrogen (special above-mentioned preferable substituent). It is ^{preferable that 0 to 1 of R 8 to} R ¹¹ are other than hydrogen (particularly the above-mentioned preferable substituent), and the others are hydrogen.
Of R ^{1 to} R ³ , one is non-hydrogen (specially preferred above-mentioned substituent) and the other is hydrogen, and one of R ^{4 to} R ⁷ is other than hydrogen (specially above-mentioned preferred substituent). It is more preferable that one of R ^{8 to} R ¹¹ is other than hydrogen (particularly the above-mentioned preferable substituent), and the other is hydrogen.

In the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e), and the formula (2-f), the a ring, the b ring, and the formula (2-f) Substituents of ring c R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ Adjacent groups are bonded to each other to form a ring. , B ring or c ring may form an aryl ring or a heteroaryl ring, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, Diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyls, at least one hydrogen in these. May be substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl.

For example, the compounds represented by the formula (2-a) are represented by the following formulas (2-a-1) and (2-a-2) depending on the mutual binding form of the substituents in the a ring, the b ring and the c ring. ), The ring structure constituting the compound changes. The A'ring, B'ring and C'ring in each formula correspond to the A ring, B ring and C ring in the formula (2), respectively. In addition, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ , a, b, c, X ¹ and X ^{2 in each equation.} The definition of is the same as the definition in Eq. (2-a).

Ring A ', B' in the formula (2-a-1) and formula (2-a-2) ring, and C 'ring, will be described by the formula (2-a), substituents ^R 1, R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , and R ¹¹ with adjacent groups bonded together, a ring, b ring, and c, respectively. It shows an aryl ring or a heteroaryl ring formed together with a ring (it can also be said to be a fused ring formed by condensing another ring structure with an a ring, a b ring, or a c ring). Although not shown in the formula, there are some compounds in which all of the a ring, b ring, and c ring are changed to A'ring, B'ring, and C'ring. Further, as can be seen from the formulas (2-a-1) and (2-a-2), for example, R ⁸ of the b ring and R ^{7 of} the c ring, R ¹¹ of the b ring and R ^{1 of} the a ring, etc. c R ⁴ and a ring of R ³ rings do not apply to the "adjacent groups", does not it are attached. That is, the "adjacent group" means an adjacent group on the same ring.

The compounds represented by the formulas (2-a-1) and (2-a-2) are, for example, formulas (2-67) to formulas (2-74) and formulas (2) listed as specific compounds described later. -76) to formula (2-83), formula (2-273) to formula (2-276), formula (2-290) to formula (2-295) and formula (2-350) to formula (2-350) Corresponds to compounds such as those represented by 355). That is, for example, a benzene ring, an indol ring, a pyrrole ring, a furan ring, a thiophene ring, a benzofuran ring, a benzothiophene ring, etc. A compound having an A'ring (or B'or C'ring) formed by condensing a cyclopentadiene ring or an inden ring, and the formed fused ring A'(or fused ring B'or fused. Ring C') is a naphthalene ring, a carbazole ring, an indole ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring, an inden ring, or a fluorene ring, respectively.

Similarly, in the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e), and the formula (2-f), the a ring, the b ring, or the c A fused ring formed by condensing another ring structure may be formed on the ring. For example, the benzene ring which is the a ring or the b ring may be formed by condensing other ring structures in the same manner as the benzene ring in the above formula (1-a) to form a condensed ring.

In the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e), and the formula (2-f), in the 5-membered ring which is the b ring or the c ring, It is particularly preferable that adjacent groups of R ^{4 to} R ¹¹ are bonded to each other to form a ring to form a fused ring. For example, in the c-rings of formulas (2-b) and (2-c), the b-rings and c-rings of formulas (2-d), formulas (2-e), and formulas (2-f), R ³ By bonding adjacent groups of ~ R ¹¹ to form a ring, a B'ring or a C'ring, which is a fused ring, can be formed. Examples of the fused ring when the ring formed is a benzene ring include an indole ring, a benzofuran ring, and a benzothiophene ring. Examples of such a structure include compounds represented by any of the formulas (2-572) to (1-588) described later.

For example, in formulas (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f), for example, _{when XX} is> O, The b ring or c ring is a furan ring, and the ring corresponding to the B'ring or C'ring of the formula (2-a-1) formed by condensing a benzene ring with this furan ring is a benzofuran ring. Is.
Further, for example, in the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e), and the formula (2-f), for example, _XX is> S. At that time, the b ring or the c ring becomes a thiophene ring, and the ring corresponding to the B'ring or C'ring of the formula (2-a-1) formed by condensing the benzene ring with the thiophene ring is It is a benzothiophene ring.

As an example, in 5-membered ring is a c ring of formula (2-b), showing an example in which a condensed ring is formed to form a benzene ring by bonding R ⁴ and R ⁵ together below.

In formula (2-b-1), R ¹ , R ² , R ³ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , X _X , Y ¹ , X ¹ and X ² are in formula (2-b). It is synonymous with each of the above, and the preferable range is also the same. R ^4b , R ^5b , R ^6b , R ^7b are hydrogen, or aryl, heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, diarylboryl (two aryls bonded via a single bond or a linking group). It is a substituent selected from the group consisting of alkyl, cycloalkyl, alkoxy, aryloxy, and substituted silyl, and at least one hydrogen in these substituents is aryl, heteroaryl, alkyl, cyclo. It may be substituted with alkyl or substituted silyl. Of R ^4b , R ^5b , R ^6b , and R ^7b , it is preferable that 0 to 2 are substituents other than hydrogen and the others are hydrogen, one is a substituent other than hydrogen, and the others are. More preferably, it is hydrogen. As a preferred range of substituents other than hydrogen, the description of the substituent described later as the first substituent (which may have a second substituent) can be referred to. As the substituent other than hydrogen, alkyl (particularly, the above-mentioned tertiary-alkyl (tR), neopentyl, etc.), cycloalkyl (for example, adamantyl, etc.), or substituted or unsubstituted diarylamino is particularly preferable.

^{X 1} and X ² in the formula (2) are independently>O,>N-R,> C (-R) ₂ ,> S, or> Se, and the R of> N-R is , aryl which may be substituted, an optionally substituted heteroaryl, optionally substituted alkyl or cycloalkyl which may be substituted, the> C (-R) ₂ for R, Hydrogen, optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl, R of> N-R and / or R of> C (-R) ₂ . May be bonded to the B ring and / or C ring by a linking group or a single bond, and the linking group is preferably _{−O−, −S−, or −C (−R) 2−.} In addition, R of the said "−C (−R) ₂₋ ” is hydrogen, alkyl, or cycloalkyl. This description formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and ^{X 1} and X in the formula (2-f) ^The same is true for 2.

In formula (2), formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f), X ¹ and X ² are preferably> O or> N-R, respectively, more preferably> N-R, which is a phenyl in which R may be substituted, and at least one R is 1. More preferably, one or two t-butyl, t-amyl, methyl or phenyl substituted phenyl> N-R, where at least one R is one t-butyl or t-amyl substituted phenyl. It is particularly preferable that> NR. X ¹ and X ² may be the same group or different from each other.

Here, the R of "> N-R and / or the R of> C (-R) ₂ in the formula (2) is bonded to the A ring, the B ring, and / or the C ring by a linking group or a single bond. In the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e), and the formula (2-f) > N-R R and / or> C (-R) ₂ R is -O-, -S-, -C (-R) _2- or single bond a ring, b ring, and / or c ring Corresponds to the provision of "combined with".

^{This specification can be expressed by a compound having a ring structure in which X 1} and X ² are incorporated into the condensed ring B'and the condensed ring C', which are represented by the following formula (2-a-3-1). That is, for example, the B'ring formed by condensing other rings so as to incorporate ^{X 1} (or X ² ) into the benzene ring which is the b ring (or c ring) in the formula (2-a). Or a compound having a C'ring). The formed fused ring B'(or fused ring C') is, for example, a carbazole ring, a phenothiazine ring, a phenothiazine ring, or an acridine ring.

^{Further, the above specification is a ring in which X 1} and / or X ² are incorporated into the fused ring A', which is represented by the following formula (2-a-3-2) or formula (2-a-3-3). It can also be expressed as a compound having a structure. That is, for example, a compound having an A'ring formed by condensing other rings so as to incorporate ^{X 1} (and / or X ² ) with respect to the benzene ring which is the a ring in the formula (2-a). be. The formed fused ring A'is, for example, a carbazole ring, a phenothiazine ring, a phenothiazine ring, or an acridine ring.

Examples of the "aryl ring" which is the A ring, the B ring, and the C ring of the formula (2) include an aryl ring having 6 to 30 carbon atoms, and an aryl ring having 6 to 16 carbon atoms is preferable. Aryl rings of 6 to 12 are more preferable, and aryl rings having 6 to 10 carbon atoms are particularly preferable. The "aryl ring" includes the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e), and the formula (2-f). ), And " ^{an aryl ring formed by bonding adjacent groups of R 1 to} R ¹¹ together with an a ring, a b ring, or a c ring".

Specific examples of the "aryl ring" include a benzene ring which is a monocyclic system, a biphenyl ring which is a bicyclic system, a naphthalene ring which is a fused bicyclic system, a tetraline ring, and a terphenyl ring (m-tel) which is a tricyclic system. (Phenyl, o-terphenyl, p-terphenyl), fused tricyclics, anthracene ring, acenaftylene ring, fluorene ring, phenalene ring, phenanthrene ring, fused tetracyclic triphenylene ring, pyrene ring, naphthalene ring, Examples thereof include a fused pentacyclic system such as a perylene ring and a pentasen ring.

Examples of the "heteroaryl ring" which is the A ring, the B ring and the C ring of the formula (2) include a heteroaryl ring having 2 to 30 carbon atoms, and a heteroaryl ring having 2 to 25 carbon atoms is preferable. A heteroaryl ring having 2 to 20 carbon atoms is more preferable, a heteroaryl ring having 2 to 15 carbon atoms is further preferable, and a heteroaryl ring having 2 to 10 carbon atoms is particularly preferable. Examples of the "heteroaryl ring" include a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms. The "heteroaryl ring" includes the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e), and the formula (2-e). f) The 5-membered ring in, and the adjacent groups of ^{"R 1} , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , and R ^11". Corresponds to the "heteroaryl ring formed with the a ring, b ring, or c ring".

Specific examples of the "heteroaryl ring" include a pyrrole ring, an oxazole ring, an isooxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxazole ring, a thiazazole ring, a triazole ring, a tetrazole ring, and a pyrazole ring. Ppyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring , Cinnoline ring, quinazoline ring, quinoxalin ring, phthalazine ring, naphthylidine ring, purine ring, pteridine ring, carbazole ring, aclysine ring, phenoxatiein ring, phenoxazine ring, phenothiazine ring, phenazine ring, indridin ring, furan ring, Examples thereof include a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a flazan ring, an oxazole ring, and a thiantolen ring.

In the above, the "aryl ring" and the "heteroaryl ring" which are the A ring, the B ring and the C ring may share a bond with the condensed bicyclic structure in the center of the formula (2) at any position. For example, when the "aryl ring" and the "heteroaryl ring" are fused rings in which two or more rings are condensed, any of the rings may share a bond with the condensed bicyclic structure in the center of the formula (1). .. Of these, as described above, the A ring, the B ring, and the C ring are 5-membered rings or 6 rings that share a bond with the condensed two-ring structure in the center of the formula (2) composed of ^{B, X 1} , and X ^2. It is preferable to have a member ring. That is, for example, in the formula (2-a), ^{the adjacent groups of R 1 to} R ³ , R ^{4 to} R ⁷ , and R ^{8 to} R ¹¹ are bonded to each other to form a ring, b ring, or c ring. When an aryl ring or a heteroaryl ring is formed together with (a 6-membered benzene ring shares a bond with the condensed bicyclic structure in the center of formula (2)), and formula (2-b), (2-c), formula (2-d), formula (2-e), or with b ring and c ring adjacent groups are bonded to one of ^R 4 ^{to R 11} of the formula (2-f) It is preferable that an aryl ring or a heteroaryl ring is formed (a 5-membered ring shares a bond with the condensed bicyclic structure in the center of formula (2)). Examples of the 5-membered ring at this time include a pyrrole ring, a furan ring, and a thiophene ring.

At least one hydrogen in the "aryl ring" or "heteroaryl ring" is the first substituent, a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted. "Diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboryl (two aryls via a single bond or a linking group) May be bonded) ", substituted or unsubstituted" alkyl ", substituted or unsubstituted" cycloalkyl ", substituted or unsubstituted" alkoxy ", substituted or unsubstituted" aryloxy ", or substituted silyl Although it may be substituted with, the first substituent of "aryl", "heteroaryl", "diarylamino" aryl, "diheteroarylamino" heteroaryl, "arylheteroarylamino" Aryl and heteroaryl, aryl of "diarylboryl", and aryl of "aryloxy" include the monovalent group of the above-mentioned "aryl ring" or "heteroaryl ring".

The "alkyl" as the first substituent may be either a straight chain or a branched chain, and examples thereof include a linear alkyl having 1 to 24 carbon atoms and a branched chain alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms) is preferable, an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms) is more preferable, and an alkyl having 1 to 6 carbon atoms is more preferable. (Branched chain alkyl having 3 to 6 carbon atoms) is more preferable, and alkyl having 1 to 5 carbon atoms (branched chain alkyl having 3 to 5 carbon atoms) is particularly preferable.

Specific alkyls include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-. Hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2- Ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n -Dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl and the like can be mentioned.

Examples of the "cycloalkyl" as the first substituent include cycloalkyl having 3 to 24 carbon atoms, preferably cycloalkyl having 3 to 20 carbon atoms, and more preferably cycloalkyl having 3 to 16 carbon atoms. Preferably, cycloalkyl having 3 to 14 carbon atoms is more preferable, cycloalkyl having 5 to 10 carbon atoms is more preferable, cycloalkyl having 5 to 8 carbon atoms is particularly preferable, and cycloalkyl having 5 to 6 carbon atoms is most preferable.

Specific cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, alkyl (particularly methyl) substituents having 1 to 4 carbon atoms, norbornenyl, and bicyclo [1]. .0.1] Butyl, Bicyclo [1.1.1] Pentyl, Bicyclo [2.0.1] Pentyl, Bicyclo [1.2.1] Hexyl, Bicyclo [3.0.1] Hexyl, Bicyclo [2] .1.2] Heptyl, bicyclo [2.2.2] Octyl, adamantyl, diamantyl, decahydronaphthalenyl, decahydroazulenyl and the like.

Examples of the "alkoxy" as the first substituent include alkoxy having a linear chain having 1 to 24 carbon atoms or a branched chain having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (alkoxy of branched chains having 3 to 18 carbon atoms) is preferable, and alkoxy having 1 to 12 carbon atoms (alkoxy of branched chains having 3 to 12 carbon atoms) is more preferable, and alkoxy having 1 to 6 carbon atoms is more preferable. Alkoxy (alkoxy of a branched chain having 3 to 6 carbon atoms) is more preferable, and alkoxy having 1 to 4 carbon atoms (alkoxy of a branched chain having 3 to 4 carbon atoms) is particularly preferable.

Specific examples of alkoxy include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, and octyloxy.

Examples of the "substituted silyl" as the first substituent include silyls substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl. For example, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl.

Examples of the "trialkylsilyl" include groups in which each of the three hydrogens in the silyl is independently substituted with an alkyl, and this alkyl refers to the group described as "alkyl" in the first substituent described above. Can be done. The alkyl preferred for substitution is an alkyl having 1 to 5 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and t-amyl.

Specific trialkylsilyls include trimethylsilyl, triethylsilyl, tripropylsilyl, trii-propylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, trit-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethyl Cyril, t-butyldipropylsilyl, t-amyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, t-amyldipropylsilyl, Examples thereof include methyldii-propylsilyl, ethyldii-propylsilyl, butyldii-propylsilyl, sec-butyldii-propylsilyl, t-butyldii-propylsilyl, and t-amyldii-propylsilyl.

Examples of the "tricycloalkylsilyl" include groups in which each of the three hydrogens in the silyl is independently substituted with cycloalkyl, and this cycloalkyl is a group described as "cycloalkyl" in the first substituent described above. Can be quoted. Preferred cycloalkyls for substitution are cycloalkyls having 5 to 10 carbon atoms, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo [1.1.1] pentyl, bicyclo [. 2.0.1. Examples thereof include decahydronaphthalenyl and decahydroazurenyl.

Specific examples of the tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

Specific examples of the dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl and the alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls are selected from the specific alkyls and cycloalkyls described above. Examples thereof include silyl in which the group to be substituted is substituted.

Specific examples of the dialkylarylsilyl substituted with two alkyls and one aryl, the alkyldiarylsilyl substituted with one alkyl and two aryls, and the triarylsilyl substituted with three aryls include the specific alkyls described above. And silyl substituted with a group selected from aryl. Specific examples of triarylsilyl include triphenylsilyl.

Further, as "aryl" in "diarylboryl" as the first substituent, the above-mentioned description of aryl can be cited. Further, the two aryls may be bonded via a single bond or a linking group (for example,> C (-R) ₂ ,>O,> S or> N-R). Here, R of> C (-R) ₂ and> N-R is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl (above, first substituent). , The first substituent may be further substituted with aryl, heteroaryl, alkyl, cycloalkyl, or a substituted silyl (above, the second substituent), and specific examples of these groups include the above-mentioned first substituent. Descriptions of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy or aryloxy as mono-substituted groups can be cited.

Specifically, the emission wavelength can be adjusted by the steric hindrance, electron donating property, and electron attracting property of the structure of the first substituent, and the group is preferably represented by the following structural formula, more preferably. , Methyl, t-butyl, t-pentyl (t-amyl), t-octyl, neopentyl, cyclohexyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-kisilyl, 2,5-xylyl, 2, 6-Xyryl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis (p- (t-butyl) phenyl) amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di -T-Butylcarbazolyl and phenoxy, more preferably methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, 2,6-xylyl, 2,4. With 6-mesityl, diphenylamino, di-p-tolylamino, bis (p- (t-butyl) phenyl) amino, carbazolyl, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl be. From the viewpoint of ease of synthesis, a larger steric hindrance is preferable for selective synthesis, and specifically, t-butyl, t-pentyl (t-amyl), t-octyl, adamantyl, o- Trill, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis (p- (t-butyl) phenyl) amino , 3,6-Dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl are preferred.

In the following structural formula, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, "tOct" represents t-octyl, and * represents the binding position.

In the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e), and the formula (2-f), R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , and R ^11, of which 1 to 4 are groups represented by any of the above structural formulas. The rest is preferably hydrogen, with ^1-3 of R 1, R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ being It is a group represented by any of the above structural formulas, and the rest is more preferably hydrogen, and R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , and R ¹¹ are more preferably methyl, t-butyl or t-amyl, and the rest are hydrogen.

The first substituent, a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diarylamino", a substituted or unsubstituted "diheteroarylamino", a substitution Alternatively, an unsubstituted "aryl heteroarylamino", a substituted or unsubstituted "diarylboryl (two aryls may be bonded via a single bond or a linking group)", a substituted or unsubstituted "alkyl", Substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", or substituted or unsubstituted "aryloxy" are described as substituted or unsubstituted, in which at least one hydrogen is the first. It may be substituted with a substituent of 2. Examples of the second substituent include aryl, heteroaryl, alkyl, cycloalkyl, and substituted silyl, and specific examples thereof include the monovalent of the above-mentioned "aryl ring" or "heteroaryl ring". References can be made to the description of the group, as well as the "alkyl", "cycloalkyl", or substituted silyl as the first substituent. Further, in aryl and heteroaryl as the second substituent, at least one hydrogen in them is aryl such as phenyl (specific example is the group described above) or alkyl such as methyl (specific example is the group described above). Alternatively, a structure substituted with a cycloalkyl (specific example is the group described above) such as cyclohexyl is also included in aryl or heteroaryl as the second substituent. As an example, when the second substituent is carbazolyl, carbazolyl in which at least one hydrogen at the 9-position is substituted with aryl such as phenyl, alkyl such as methyl or cycloalkyl such as cyclohexyl is also the second. Included in heteroaryl as a substituent.

Formula (2-a), formula (2-b), formula (2-c), formula (2-d), ^R 1 of formula (2-e), and the formula ^{(2-f), R 2} , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , and R ¹¹ of aryl, heteroaryl, diarylamino aryl, diheteroarylamino heteroaryl, aryl heteroarylamino Examples of the aryl and heteroaryl, the aryl of diarylboryl, or the aryl of aryloxy include monovalent groups of the "aryl ring" or "heteroaryl ring" described in the formula (2). Further, as the ^{alkyl, cycloalkyl or alkoxy in R 1 to} R ¹¹ , the description of “alkyl”, “cycloalkyl” or “alkoxy” as the first substituent in the above-mentioned explanation of the formula (2) is referred to. be able to. The same applies to aryl, heteroaryl, alkyl or cycloalkyl as substituents to these groups. In addition, ^{adjacent groups of R 1} , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , and R ¹¹ are bonded to each other to form a ring and b. Heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, diarylboryl, alkyl, cycloalkyl, which are substituents to these rings when an aryl ring or heteroaryl ring is formed together with the ring or c ring. The same applies to alkoxy or aryloxy, and additional substituents such as aryl, heteroaryl, alkyl, or cycloalkyl.

^{The R of> N-R in X 1} and X ² of formula (2) is aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in aryl or heteroaryl is, for example, alkyl, cycloalkyl, or substitution. It may be substituted with silyl. Examples of the aryl, heteroaryl, alkyl, and cycloalkyl include the groups described above. In particular, aryls with 6 to 10 carbon atoms (eg, phenyl, naphthyl, etc.), heteroaryls with 2 to 15 carbon atoms (eg, carbazolyl, etc.), alkyls with 1 to 5 carbon atoms (eg, methyl, ethyl, etc.), or 5 to 5 carbon atoms. A cycloalkyl of 10 (preferably cyclohexyl or adamantyl) is preferred. This description formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and ^{X 1} and X in the formula (2-f) ^The same is true for 2. Formula (2-a), in the ^{X 1} and ^{X 2} in the formula (2-b), formula (2-c), formula (2-d), formula (2-e), and the formula (2-f)> R of N-R may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or 3 to 3 carbon atoms. Heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, which may be substituted with 14 cycloalkyl, and alkyl having 1 to 4 carbon atoms or carbon number of carbon atoms. It is preferably an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, which may be substituted with 5 to 10 cycloalkyls.

> C (-R) ₂ ^{R in X 1} and X ² of formula (2) is hydrogen, aryl, alkyl, or cycloalkyl, and at least one hydrogen in aryl is, for example, alkyl, cycloalkyl, or substituted silyl. It may be replaced with. Examples of the aryl, alkyl, and cycloalkyl include the groups described above. In particular, aryls having 6 to 10 carbon atoms (for example, phenyl, naphthyl, etc.), alkyls having 1 to 5 carbon atoms (for example, methyl, ethyl, etc.), or cycloalkyls having 5 to 10 carbon atoms (preferably cyclohexyl, adamantyl, etc.) are preferable. This description formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and ^{X 1} and X in the formula (2-f) ^The same is true for 2. Formula (2-a), in the ^{X 1} and ^{X 2} in the formula (2-b), formula (2-c), formula (2-d), formula (2-e), and the formula (2-f)> R of C (-R) ₂ is hydrogen, an alkyl having 1 to 6 carbon atoms or an aryl having 6 to 12 carbon atoms which may be substituted with a cycloalkyl having 3 to 14 carbon atoms, and an alkyl having 1 to 6 carbon atoms. , Or an aryl having 6 to 10 carbon atoms, which may be substituted with hydrogen, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, which is a cycloalkyl having 3 to 14 carbon atoms, and has 1 to 1 carbon atoms. It is preferably an alkyl of 4 or a cycloalkyl having 5 to 10 carbon atoms.

_{The R of "-C (-R) 2-} " which is a linking group in the formula (2) is hydrogen, alkyl, or cycloalkyl, and examples of the alkyl and cycloalkyl include the above-mentioned groups. In particular, alkyl having 1 to 5 carbon atoms (for example, methyl, ethyl, etc.) or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferable. This description is a linking group in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f). The same applies to "-C (-R) _2- ".

The dopant material may be a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by the formula (2). The multimer is preferably of formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f). It is a multimer of a polycyclic aromatic compound having a plurality of unit structures represented. The multimer is preferably a 2-hexamer, more preferably a 2-3mer, and particularly preferably a dimer. The multimer may be in the form of having a plurality of the above unit structures in one compound. For example, the multimer may be a linking group such as a single bond, an alkylene group having 1 to 3 carbon atoms, a phenylene group, or a naphthylene group. In addition to the plurality of bonded forms, any ring (A ring, B ring or C ring, a ring, b ring or c ring) included in the unit structure is bonded so as to be shared by the plurality of unit structures. It may be a form in which arbitrary rings (A ring, B ring or C ring, a ring, b ring or c ring) included in the unit structure are bonded to each other so as to condense with each other. good.

Examples of such a multimer include the following formulas (2-4), formulas (2-4-1), formulas (2-4-2), formulas (2-5-1) to formulas (2-5). -4) or a multimeric compound represented by the formula (2-6) can be mentioned. Each reference numeral in these formulas has the same meaning as each of the formulas (2-a), and the preferable range is also the same. The multimeric compound represented by the following formula (2-4) is represented by a plurality of formulas (2-a) so as to share the benzene ring which is the a ring, if it is explained by the formula (2-a). It is a multimeric compound having a unit structure to be obtained in one compound. Further, the multimeric compound represented by the following formula (2-4-1) is described by the formula (2-a) so as to share the benzene ring which is the a ring, and has two formulas (2-). It is a multimeric compound having a unit structure represented by a) in one compound. Further, the multimeric compound represented by the following formula (2-4-2) is described by the formula (2-a) so as to share the benzene ring which is the a ring, and has three formulas (2-4-2). It is a multimeric compound having a unit structure represented by a) in one compound. Further, the multimeric compound represented by the following formulas (2-5-1) to (2-5-4) is benzene which is a b-ring (or c-ring) according to the formula (2-a). It is a multimeric compound having a unit structure represented by a plurality of formulas (2) in one compound so as to share a ring. Further, the multimeric compound represented by the following formula (2-6) is, for example, a benzene ring which is a b ring (or a ring or c ring) having a certain unit structure, if it is described by the formula (2-a). A multimeric compound having a unit structure represented by a plurality of formulas (2-a) in one compound so as to be condensed with a benzene ring which is a b ring (or a ring or c ring) of the unit structure. be.

The multimeric compound has a quantified form represented by the formula (2-4), the formula (2-4-1) or the formula (2-4-2), and the formulas (2-5-1) to (2). It may be a multimer in combination with any of −5-4) or the quantified form represented by the formula (2-6), and formulas (2-5-1) to (2-5-). It may be a multimer in which the quantifier form represented by any one of 4) and the quantifier form represented by the formula (2-6) are combined, and the formulas (2-4) and (2) may be used. 4-1) or the quantified form represented by the formula (2-4-2) and the quantified form represented by any of the formulas (2-5-1) to (2-5-4). It may be a multimer in combination with the quantifier form represented by the formula (2-6).

Further, in the formula (2), the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e), or the formula (2-f). The hydrogen in the chemical structure of the represented polycyclic aromatic compound and its multimer may be deuterium, cyano or halogen in whole or in part. For example, in the formula (2), the A ring, the B ring, the C ring (the A to C rings are aryl rings or heteroaryl rings), the substituents to the A to C rings, and X ³ and X ⁴ are> N. Hydrogen in R (= alkyl, cycloalkyl, aryl) when −R or> C (−R) ₂ can be replaced with deuterium, cyano or halogen, among which all or one in aryl or heteroaryl. An embodiment in which the hydrogen in the portion is replaced with deuterium, cyano or halogen can be mentioned. The halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine.

Further, in the formula (2), the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e), or the formula (2-f). At least one selected from the group consisting of aryl rings and heteroaryl rings in the chemical structure of the represented polycyclic aromatic compound and its multimer may be condensed with at least one cycloalkane.

For example, the aryl ring and the heteroaryl ring in the aryl ring and the heteroaryl ring which are the A ring, the B ring, the C ring, the a ring, the b ring, and the c ring, and the first and second substitutions in the A ring to the C ring. Aryl as a group (aryl, diarylamino, arylheteroarylamino, arylboryl or aryloxy) and heteroaryl (heteroaryl, diheteroarylamino or heteroaryl moiety in arylheteroarylamino), a ring, b. Aryl (same as above) and heteroaryl (same as above) as first and second substituents on rings, c-rings, and> N-R and> C (- ^{) which are X 1} , X ^2. R) At least one of the aryl (similar to above) and heteroaryl (similar to above _{) as R of 2 may be condensed with at least one cycloalkane.}

Preferably, the A-ring, B-ring, C-ring, a-ring, b-ring, c-ring aryl ring and heteroaryl ring, and aryl (aryl, diarylamino,) as the first substituent in the A-ring to C-ring. Aryl (aryl moiety in diarylboryl or aryloxy) and heteroaryl (heteroaryl moiety in heteroaryl or diheteroarylamino), aryl as the first substituent on rings a-c (similar to above) and heteroaryl (similar to above). as described above), ^and, X 1, a ^{X 2} is> N-R and> C _(-R) same as the aryl (above the _second R) and at least one of the heteroaryl (as above) , May be condensed with at least one cycloalkane.

More preferably, an aryl ring which is an A ring, a B ring, a C ring, an a ring, a b ring, or a c ring, or an aryl as a first substituent in the A to C rings (aryl moiety in aryl or diarylamino). And heteroaryls (heteroaryl moieties in heteroaryls), aryls as first substituents on rings a, b, and c (same as above) and heteroaryls (similar to above), and X ¹ , X. ^At least one of the aryl as R of> N-R and> C (-R) ₂ (similar to the above) of 2 may be condensed with at least one cycloalcan.

More preferably, the aryl ring as the A ring, the B ring, the C ring, the a ring, the b ring, the c ring, and the aryl as the first substituent in the A to C rings (aryl moiety in aryl or diarylamino). , Aryl as the first substituent on rings a, b, c (similar to above), and as R of> N-R and> C (-R) ₂ ^{which are X 1} , X ^2. At least one of the aryls (similar to the above) may be condensed with at least one cycloalkane.

Examples of the "cycloalkane" include cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, and cycloalkanes having 5 to 10 carbon atoms. Examples thereof include alkanes, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, and cycloalkanes having 5 carbon atoms.

Specific cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptan, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo [1.0.1] butane, bicyclo [1.1.1] pentane, and so on. Bicyclo [2.0.1] pentane, bicyclo [1.2.1] hexane, bicyclo [3.0.1] hexane, bicyclo [2.1.2] heptane, bicyclo [2.2.2] octane, Examples thereof include adamantane, diamantane, decahydronaphthalene and decahydroazulene, and alkyl (particularly methyl) substituents, halogen (particularly fluorine) substitutes and dehydrohydrogen substitutes having 1 to 5 carbon atoms thereof.

Among these, a structure in which at least one hydrogen is substituted in the carbon at the α-position of the cycloalkane (the carbon at the position adjacent to the carbon at the condensation site in the cycloalkyl condensed to the aromatic ring or the heteroaromatic ring) is preferable. , A structure in which two hydrogens are substituted in the carbon at the α-position is more preferable, and a structure in which a total of four hydrogens are substituted in the carbon at the α-position is further preferable. Examples of this substituent include alkyl (particularly methyl) substituents having 1 to 5 carbon atoms, halogen (particularly fluorine) substituents and deuterium substituents.

In particular, it is preferable that the aryl ring or the heteroaryl ring has a structure in which a partial structure represented by the following formula (B10) or formula (B11) is bonded to an adjacent carbon atom.

In formula (B10) and formula (B11), Me represents methyl. * Indicates the bond position and is bonded to two adjacent elements on the ring of the aryl ring or heteroaryl ring to which the group represented by the formula (B10) or the formula (B11) is bonded, respectively.
Examples of compounds having such a structure include the following compounds.

The number of cycloalkanes condensed on one aromatic ring or complex aromatic ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, an example in which one or more cycloalkanes are condensed on one benzene ring (phenyl) is shown below. Cycloalkanes condensed as in the formulas (Cy-1-4) and (Cy-2-4) may be condensed with each other. Even if the ring (group) to be condensed is an aromatic ring or a heteroaromatic ring other than the benzene ring (phenyl), the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane. Even if there is, it is the same.

At least one −CH ₂₋ in the cycloalkane may be substituted with −O−. _{For example, an example in which one or more -CH 2} − in a cycloalkane condensed on one benzene ring (phenyl) is replaced with -O- is shown below. Even if the ring (group) to be condensed is an aromatic ring or a heteroaromatic ring other than the benzene ring (phenyl), the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane. Even if there is, it is the same.

At least one hydrogen in the cycloalkane may be substituted, and the substituents include, for example, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are single-bonded). (Or may be attached via a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, dehydrogen, cyano or halogen, the details of which are described above in the first substituent. The explanation can be quoted. Among these substituents, alkyl (for example, alkyl having 1 to 6 carbon atoms), cycloalkyl (for example, cycloalkyl having 3 to 14 carbon atoms), halogen (for example, fluorine), deuterium and the like are preferable. Further, when cycloalkyl is substituted, a substituted form forming a spiro structure may be used, and an example thereof is shown below.

Other forms of cycloalkane condensation include formula (2), formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), Alternatively, the polycyclic aromatic compound represented by the formula (2-f) and its multimer are, for example,> NR in which R is a cycloalkane-condensed aryl> NR, and a cycloalkane-condensed diarylamino (this). Examples include carbazolyl condensed with cycloalkane (condensation to this benzene ring portion) or benzocarbazolyl condensed with cycloalkane (condensation to this benzene ring portion). As for "diarylamino", the group described as the above "first substituent" can be mentioned.

Further, as more specific examples, the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e), or the formula (2-). R ² in polycyclic aromatics and multimers thereof represented by f) a fused to a fused diarylamino (fused to the aryl moiety) or condensed carbazolyl (this benzene ring moiety in cycloalkane with cycloalkane ).

As a more specific example of the polycyclic aromatic compound represented by the formula (2), for example, a compound represented by the following formula can be mentioned. In the formula below, "Me" is methyl, "tBu" is t-butyl, "iPr" is isopropyl, "Ph" is phenyl, "tAm" is t-amyl (terrific pentyl), and "D" is deuterium. Indicates hydrogen.

1-2-2. Method for producing a polycyclic aromatic compound represented by the formula (2) and its multimer The polycyclic aromatic compound represented by the formula (2) and its multimer are described in, for example, International Publication No. 2019/909052. It can be synthesized by the method disclosed as "Method for producing a polycyclic aromatic compound represented by (2) and its multimer".

1-3. Light-emitting layer The light-emitting layer may be either a single layer or a plurality of layers, and each is formed of a light-emitting layer material (host material, dopant material). The host material may be one compound represented by the formula (1) or a combination of two or more compounds represented by the formula (1), and the compound represented by the formula (1) and the formula. It may be a combination of compounds other than the compound represented by (1). The host material is preferably one compound represented by the formula (1) or a combination of two or more compounds represented by the formula (1). The dopant material may be one compound represented by the formula (2) or a combination of two or more compounds represented by the formula (2), and may be represented by the formula (2). It may be a combination of a compound and a compound other than the compound represented by the formula (2). The dopant material is preferably a combination of one compound represented by the formula (2) or two or more compounds represented by the formula (2).

The dopant material may be included in the entire host material, partially, or in any part. As a doping method, it can be formed by a co-evaporation method with a host material, but it may be mixed with the host material in advance and then vapor-deposited at the same time.

The amount of the host material used depends on the type of host material and may be determined according to the characteristics of the host material. The guideline for the amount of the host material used is preferably 50 to 99.99% by mass, more preferably 80 to 99.95% by mass, and further preferably 90 to 99.9% by mass of the entire material for the light emitting layer. Is.

The amount of the dopant material used varies depending on the type of the dopant material, and may be determined according to the characteristics of the dopant material. The guideline for the amount of the dopant used is preferably 0.001 to 50% by mass, more preferably 0.05 to 20% by mass, and further preferably 0.1 to 10% by mass of the entire light emitting layer material. be. The above range is preferable in that, for example, the density quenching phenomenon can be prevented.

Host materials that can be used in combination with the compound represented by the formula (1) include fused ring derivatives such as pyrene and dibenzoglycene, bisstyrylanthracene derivatives and distyrylbenzene derivatives, which have been known as luminescent materials for a long time. Examples thereof include bisstyryl derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, and benzofluorene derivatives.

Examples of the dopant material that can be used in combination with the compound represented by the formula (2) include fused ring derivatives such as anthracene and pyrene, which have been known as illuminants, and bisstyryl such as bisstyryl anthracene derivatives and distyrylbenzene derivatives. Derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzofluorene derivatives and the like can be mentioned.

2. The electron injection layer and the electron transport layer in the organic electroluminescent device The electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a role of efficiently transporting the electrons injected from the cathode 108 or the electrons injected from the cathode 108 through the electron injection layer 107 to the light emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are formed by laminating and mixing one or more of the electron transport / injection materials or a mixture of the electron transport / injection material and the polymer binder, respectively.

The electron injection / transport layer is a layer in which electrons are injected from the cathode and is in charge of further transporting electrons, and it is desirable that the electron injection efficiency is high and the injected electrons are efficiently transported. For that purpose, it is preferable that the substance has a high electron affinity, a high electron mobility, excellent stability, and is less likely to generate trap impurities during production and use. However, when considering the transport balance between holes and electrons, the electron transport capacity is so high when it mainly plays a role of efficiently blocking the holes from the anode from flowing to the cathode side without recombination. Even if it is not high, it has the same effect of improving luminous efficiency as a material having high electron transport capacity. Therefore, the electron injection / transport layer in the present embodiment may also include a layer function that can efficiently block the movement of holes.

As the material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107, it is used for a compound conventionally used as an electron transfer compound in a photoconductive material, an electron injection layer and an electron transport layer of an organic EL element. It can be arbitrarily selected and used from the known compounds known.

The material used for the electron transport layer or the electron injection layer is a compound composed of an aromatic ring or a complex aromatic ring composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon and phosphorus. It is preferable to contain at least one selected from a pyrrole derivative, a condensed ring derivative thereof, and a metal complex having an electron-accepting nitrogen. Specifically, fused ring-based aromatic ring derivatives such as naphthalene and anthracene, styryl-based aromatic ring derivatives typified by 4,4'-bis (diphenylethenyl) biphenyl, perinone derivatives, coumarin derivatives, and naphthalimide derivatives. , Quinone derivatives such as anthracene and diphenoquinone, phosphine oxide derivatives, arylnitrile derivatives and indole derivatives. Examples of the metal complex having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complex, azomethine complex, tropolone metal complex, flavonol metal complex and benzoquinoline metal complex. These materials may be used alone, but may be mixed with different materials.

Specific examples of other electron transfer compounds include borane derivatives, pyridine derivatives, naphthalene derivatives, fluorantene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, and anthraquinone derivatives. , Diphenoquinone derivative, diphenylquinone derivative, perylene derivative, oxadiazole derivative (1,3-bis [(4-t-butylphenyl) 1,3,4-oxadiazolyl] phenylene, etc.), thiophene derivative, triazole derivative (N- Naphthyl-2,5-diphenyl-1,3,4-triazole, etc.), thiazazole derivatives, metal complexes of oxine derivatives, quinolinol-based metal complexes, quinoxalin derivatives, quinoxalin derivative polymers, benzazole compounds, gallium complexes, pyrazole derivatives, Perfluoroylated phenylene derivative, triazine derivative, pyrazine derivative, benzoquinoline derivative (2,2'-bis (benzo [h] quinoline-2-yl) -9,9'-spirobifluorene, etc.), imidazole pyridine derivative, benzo Imidazole derivatives (tris (N-phenylbenzoimidazol-2-yl) benzene, etc.), benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as telpyridine, bipyridine derivatives, telpyridine derivatives (1,3- Bis (4'-(2,2': 6', 2 "-terpyridinyl)) benzene, etc.), naphthylidine derivatives (bis (1-naphthyl) -4- (1,8-naphthylidine-2-yl) phenylphosphine oxide Etc.), aldazine derivatives, pyrimidine derivatives, arylnitrile derivatives, indol derivatives, phosphoroxide derivatives, bisstyryl derivatives, silol derivatives, azoline derivatives and the like.

Further, a metal complex having electron-accepting nitrogen can also be used. can give.

The above-mentioned materials may be used alone, but may be mixed with different materials.

Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluorantene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzoimidazole derivatives, phenanthroline derivatives, quinolinol-based metals Complexes, thiazole derivatives, benzothiazole derivatives, silol derivatives and azoline derivatives are preferred.

<Borane derivative>
The borane derivative is, for example, a compound represented by the following formula (ETM-1), and is disclosed in detail in JP-A-2007-27587.

In formula (ETM-1), R ¹¹ and R ¹² are independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, respectively. At least one of the rings, or cyanos, R ^{13 to} R ¹⁶ are independently optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl, respectively. , X are optionally substituted arylene, Y is optionally substituted aryl having 16 or less carbon atoms, substituted boron, or optionally substituted carbazolyl, and n. Are independently integers from 0 to 3. In addition, examples of the substituent in the case of "may be substituted" or "substituted" include aryl, heteroaryl, alkyl, cycloalkyl and the like.

Among the compounds represented by the formula (ETM-1), the compound represented by the following formula (ETM-1-1) and the compound represented by the following formula (ETM-1-2) are preferable.

In formula (ETM-1-1), R ¹¹ and R ¹² are independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen, respectively. At least one of the containing heterocycles, or cyano, R ^{13 to} R ¹⁶ are independently optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl, respectively. R ²¹ and R ²² are independently of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano. At least one, X ¹ is an arylene having 20 or less carbon atoms which may be substituted, n is an integer of 0 to 3 independently, and m is 0 to 4 independently. Is an integer of. In addition, examples of the substituent in the case of "may be substituted" or "substituted" include aryl, heteroaryl, alkyl, cycloalkyl and the like.

In formula (ETM-1-2), R ¹¹ and R ¹² are independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen, respectively. At least one of the containing heterocycles, or cyano, R ^{13 to} R ¹⁶ are independently optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl, respectively. X ¹ is an arylene having 20 or less carbon atoms which may be substituted, and n is an integer of 0 to 3 independently. In addition, examples of the substituent in the case of "may be substituted" or "substituted" include aryl, heteroaryl, alkyl, cycloalkyl and the like.

（各式中、Ｒ^ａは、それぞれ独立してアルキル、シクロアルキルまたは置換されていてもよいフェニルであり、＊は結合位置を表す。） Specific examples of X ¹ include divalent groups represented by any of the following formulas (X-1) to (X-9).

(In each formula, ^Ra is an independently alkyl, cycloalkyl or optionally substituted phenyl, and * represents the bond position.)

Specific examples of this borane derivative include the following compounds.

This borane derivative can be produced by using a known raw material and a known synthesis method.

<Pyridine derivative>
The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), preferably a compound represented by the formula (ETM-2-1) or the formula (ETM-2-2).

φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4. be.

In the formula (ETM-2-1), R ^{11 to} R ¹⁸ are independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), and cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms). ) Or aryl (preferably aryl with 6 to 30 carbon atoms).

In the formula (ETM-2-2), R ¹¹ and R ¹² are independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), and cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), respectively. ) Or aryl (preferably aryl having 6 to 30 carbon atoms), and R ¹¹ and R ¹² may be bonded to form a ring.

In each formula, the "pyridine-based substituent" is any of the following formulas (Py-1) to (Py-15) (* in the formula represents a bond position), and the pyridine-based substituent is Each may be independently substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms. Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl and the like, with methyl being preferred. Further, the pyridine-based substituent may be bonded to φ, anthracene ring or fluorene ring in each formula via a phenylene group or a naphthylene group.

The pyridine-based substituent is any of the formulas (Py-1) to (Py-15), and among these, any of the following formulas (Py-21) to (Py-44) (in the formula). * Indicates the bonding position.).

At least one hydrogen in each pyridine derivative may be substituted with deuterium, and of the two "pyridine-based substituents" in the formula (ETM-2-1) and the formula (ETM-2-2). One may be replaced with aryl.

The "alkyl" in R ^{11 to} R ¹⁸ may be either a straight chain or a branched chain, and examples thereof include a straight chain alkyl having 1 to 24 carbon atoms and a branched chain alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms). A more preferable "alkyl" is an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms). A more preferable "alkyl" is an alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms). A particularly preferable "alkyl" is an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms).

Specific "alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1 -Methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2 -Propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, Examples thereof include n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl and n-eicocil.

As the alkyl having 1 to 4 carbon atoms to be substituted with the pyridine-based substituent, the above description of the alkyl can be cited.

Examples of the "cycloalkyl" in R ^{11 to} R ¹⁸ include cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferable "cycloalkyl" is a cycloalkyl having 3 to 8 carbon atoms. A more preferable "cycloalkyl" is a cycloalkyl having 3 to 6 carbon atoms.
Specific examples of the "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, dimethylcyclohexyl and the like.

As the ^{"aryl" in R 11 to} R ¹⁸ , the preferred aryl is an aryl having 6 to 30 carbon atoms, the more preferable aryl is an aryl having 6 to 18 carbon atoms, and more preferably an aryl having 6 to 14 carbon atoms. Yes, particularly preferably an aryl having 6 to 12 carbon atoms.

Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, which is a monocyclic aryl, (1-, 2-) naphthyl, which is a fused dicyclic aryl, and acenaphthylene- (which is a condensed tricyclic aryl). 1-, 3-, 4-, 5-) yl, fluorene- (1-, 2-, 3-, 4-, 9-) yl, phenalene- (1-, 2-) yl, (1-, 2) -, 3-, 4-, 9-) phenanthryl, triphenylene- (1-, 2-) yl, which is a fused tetracyclic aryl, pyrene- (1-, 2-, 4-) yl, naphthacene- (1-, 1-) , 2-, 5-) yl, perylene- (1-, 2-, 3-) yl which is a fused pentacyclic aryl, pentacene- (1-, 2-, 5-, 6-) yl and the like. ..

Preferred "aryls having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, chrysenyl, triphenylenyl and the like, more preferably phenyl, 1-naphthyl, 2-naphthyl or phenanthryl, and particularly preferably phenyl, 1 -Naphtyl or 2-naphthyl can be mentioned.

^{R 11} and R ¹² in the formula (ETM-2-2) may be combined to form a ring, and as a result, the 5-membered ring of the fluorene skeleton has cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane. , Fluorene, inden, etc. may be spiro-bonded.

Specific examples of this pyridine derivative include the following compounds.

This pyridine derivative can be produced by using a known raw material and a known synthesis method.

<Fluoranthene derivative>
The fluoranthene derivative is, for example, a compound represented by the following formula (ETM-3), and is disclosed in detail in International Publication No. 2010/134352.

In formula (ETM-3), X ^12- X ²¹ are hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted hetero. Represents aryl. Here, examples of the substituent when substituted include aryl, heteroaryl, alkyl, cycloalkyl and the like.

Specific examples of this fluoranthene derivative include the following compounds.

<BO derivative>
The BO derivative is, for example, a multimer of a polycyclic aromatic compound represented by the following formula (ETM-4) or a polycyclic aromatic compound having a plurality of structures represented by the following formula (ETM-4).

R ^{61 to} R ⁷¹ are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these. May be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

Further, ^{adjacent groups of R 61 to} R ⁷¹ may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, b ring or c ring, and at least one hydrogen in the formed ring. May be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, in which at least one hydrogen is aryl, heteroaryl, alkyl or It may be substituted with cycloalkyl.

Further, at least one hydrogen in the compound or structure represented by the formula (ETM-4) may be substituted with halogen or deuterium.

For the explanation of the substituent and the form of ring formation in the formula (ETM-4), the description of the polycyclic aromatic compound represented by the formula (1) or the formula (2) can be cited.

Specific examples of this BO-based derivative include the following compounds.

This BO-based derivative can be produced by using a known raw material and a known synthesis method.

<Anthracene derivative>
One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5).

Ar ¹ is independently a single bond, divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

Ar ² is independently an aryl having 6 to 20 carbon atoms, preferably an aryl having 6 to 16 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms. .. Specific examples of the "aryl having 6 to 20 carbon atoms" include phenyl, which is a monocyclic aryl, (o-, m-, p-) trill, and (2,3-,2,4-,2,5-). , 2,6-, 3,4-, 3,5-) xsilyl, mesityl (2,4,6-trimethylphenyl), (o-, m-, p-) cumenyl, bicyclic aryl (2) -, 3-, 4-) Biphenylyl, fused bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenyl (m-terphenyl-2'-yl, m-terphenyl-4) '-Il, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2 -Il, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p- Terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), fused tricyclic aryl, anthracene- (1-, 2-, 9-) yl, acenaphthylene- (1-, 3-, 4-, 5-) yl, fluoren- (1-, 2-, 3-, 4-, 9-) yl, phenalen- (1-, 2-) yl, (1-, 2-) 2-, 3-, 4-, 9-) phenanthryl, fused tetracyclic aryl triphenylene- (1-, 2-) yl, pyrene- (1-, 2-, 4-) yl, tetracene- (1) -, 2-, 5-) yl, perylene- (1-, 2-, 3-) yl, which is a fused pentacyclic aryl, and the like can be mentioned. Specific examples of the "aryl having 6 to 10 carbon atoms" include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetrasenyl, perylenyl and the like.

R ^{1 to} R ⁴ are independently hydrogen, an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 6 carbon atoms, or an aryl having 6 to 20 carbon atoms.

The alkyl having 1 to 6 carbon atoms in R ^{1 to} R ⁴ may be either a straight chain or a branched chain. That is, it is a straight chain alkyl having 1 to 6 carbon atoms or a branched chain alkyl having 3 to 6 carbon atoms. More preferably, it is an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, Examples thereof include 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, etc., preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl. , Methyl, ethyl, or t-butyl is more preferred.

Specific examples of cycloalkyl having 3 to 6 carbon atoms in R ^{1 to} R ⁴ include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl and dimethylcyclohexyl.

Regarding the aryl having 6 to 20 carbon atoms in R ^{1 to} R ^4, the aryl having 6 to 16 carbon atoms is preferable, the aryl having 6 to 12 carbon atoms is more preferable, and the aryl having 6 to 10 carbon atoms is particularly preferable. As a specific example of "aryl having 6 to 20 carbon atoms", a specific example of "aryl having 6 to 20 carbon atoms" ^{in Ar 2 can be cited.} Preferred "aryl of 6-20 carbon atoms" are phenyl, biphenylyl, terphenylyl or naphthyl, more preferably phenyl, biphenylyl, 1-naphthyl, 2-naphthyl or m-terphenyl-5'-yl. More preferably, it is phenyl, biphenylyl, 1-naphthyl or 2-naphthyl, and most preferably phenyl.

Specific examples of these anthracene derivatives include the following compounds.

These anthracene derivatives can be produced using known raw materials and known synthetic methods.

<Benzofluorene derivative>
The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6).

Ar ¹ is an aryl having 6 to 20 carbon atoms independently, and the same explanation as “aryl having 6 to 20 carbon atoms” ^{in Ar 2 of the formula (ETM-5) can be quoted.} Aryl having 6 to 16 carbon atoms is preferable, aryl having 6 to 12 carbon atoms is more preferable, and aryl having 6 to 10 carbon atoms is particularly preferable. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphtylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetrasenyl, perylenyl and the like.

Ar ² is independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms). ), and the two Ar ² may form a ring.

The "alkyl" in Ar ² may be either straight chain or branched chain, and examples thereof include straight chain alkyl having 1 to 24 carbon atoms and branched chain alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms). A more preferable "alkyl" is an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms). A more preferable "alkyl" is an alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms). A particularly preferable "alkyl" is an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms). Specific "alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1 -Methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl and the like can be mentioned.

Examples of the "cycloalkyl" in Ar ² include cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferable "cycloalkyl" is a cycloalkyl having 3 to 8 carbon atoms. A more preferable "cycloalkyl" is a cycloalkyl having 3 to 6 carbon atoms. Specific examples of the "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, dimethylcyclohexyl and the like.

As ^{the "aryl" in Ar 2} , the preferred aryl is an aryl having 6 to 30 carbon atoms, the more preferable aryl is an aryl having 6 to 18 carbon atoms, and more preferably an aryl having 6 to 14 carbon atoms, particularly. It is preferably an aryl having 6 to 12 carbon atoms.

Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, pentasenyl and the like.

Two Ar ² may form a ring, as a result, the 5-membered ring of the fluorene skeleton, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene or indene are spiro-linked You may.

Specific examples of this benzofluorene derivative include the following compounds.

This benzofluorene derivative can be produced by using a known raw material and a known synthetic method.

<Phosphine oxide derivative>
The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1). Details are also described in WO 2013/07927 and WO 2013/079678.

R ⁵ is a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl, heteroaryl aryl or 5 to 20 carbon atoms of 6 to 20 carbon atoms 3 to 16 carbon atoms,
R ⁶ is CN, substituted or unsubstituted, alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, heteroalkyl having 1 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, and 5 to 5 carbon atoms. 20 heteroaryls, alkoxys with 1 to 20 carbons or aryloxys with 6 to 20 carbons.
R ⁷ and R ⁸ are independently substituted or unsubstituted aryls having 6 to 20 carbon atoms or heteroaryls having 5 to 20 carbon atoms, respectively.
R ⁹ is oxygen or sulfur
j is 0 or 1, k is 0 or 1, r is an integer from 0 to 4, and q is an integer from 1 to 3.
Here, examples of the substituent when substituted include aryl, heteroaryl, alkyl, cycloalkyl and the like.

The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2).

R ^{1 to} R ³ may be the same or different, hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, cycloalkylthio, aryl ether group, aryl thio ether group, aryl, heterocycle. It is selected from fused rings formed between groups, halogens, cyanos, formyls, carbonyls, carboxyls, aminos, nitros, silyls, and adjacent substituents.

Ar ¹ may be the same or different and is an arylene or a heteroarylene. Ar ² may be the same or different and is aryl or heteroaryl. However, ^{at least one of Ar 1} and Ar ² has a substituent or forms a fused ring with an adjacent substituent. n is an integer from 0 to 3, and when n is 0, the unsaturated structure portion does not exist, and when n is 3, R ¹ does not exist.

Among these substituents, alkyl means, for example, a saturated aliphatic hydrocarbon group such as methyl, ethyl, propyl, butyl, etc., which may be unsubstituted or substituted. The substituent when substituted is not particularly limited, and examples thereof include alkyl, aryl, and heterocyclic groups, and this point is also common to the following description. The number of carbon atoms of the alkyl is not particularly limited, but is usually in the range of 1 to 20 from the viewpoint of availability and cost.

Further, the cycloalkyl means, for example, a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, and adamantyl, which may be substituted or substituted. The carbon number of the alkyl moiety is not particularly limited, but is usually in the range of 3 to 20.

Further, aralkyl refers to an aromatic hydrocarbon group mediated by an aliphatic hydrocarbon such as benzyl or phenylethyl, and both the aliphatic hydrocarbon and the aromatic hydrocarbon may be substituted or substituted. do not have. The carbon number of the aliphatic portion is not particularly limited, but is usually in the range of 1 to 20.

Further, the alkenyl refers to an unsaturated aliphatic hydrocarbon group containing a double bond such as vinyl, allyl, or butadienyl, which may be unsubstituted or substituted. The carbon number of the alkenyl is not particularly limited, but is usually in the range of 2 to 20.

Further, the cycloalkenyl indicates, for example, an unsaturated alicyclic hydrocarbon group containing a double bond such as cyclopentenyl, cyclopentadienyl, cyclohexene, etc., which may be substituted or substituted.

Further, the alkynyl indicates an unsaturated aliphatic hydrocarbon group containing a triple bond such as acetylenyl, which may be unsubstituted or substituted. The carbon number of alkynyl is not particularly limited, but is usually in the range of 2 to 20.

Further, the alkoxy refers to an aliphatic hydrocarbon group via an ether bond such as methoxy, and the aliphatic hydrocarbon group may be substituted or substituted. The number of carbon atoms of the alkoxy is not particularly limited, but is usually in the range of 1 to 20.

Alkoxythio is a group in which the oxygen atom of the ether bond of alkoxy is replaced with a sulfur atom.

Further, the cycloalkylthio is a group in which the oxygen atom of the ether bond of the cycloalkoxy group is replaced with a sulfur atom.

Further, the aryl ether group indicates, for example, an aromatic hydrocarbon group via an ether bond such as phenoxy, and the aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms of the aryl ether group is not particularly limited, but is usually in the range of 6 to 40.

The arylthioether group is a group in which the oxygen atom of the ether bond of the aryl ether group is replaced with a sulfur atom.

Further, the aryl means, for example, an aromatic hydrocarbon group such as phenyl, naphthyl, biphenylyl, phenanthryl, terphenylyl, and pyrenyl. Aryl may be unsubstituted or substituted. The number of carbon atoms of the aryl is not particularly limited, but is usually in the range of 6 to 40.

Further, the heterocyclic group refers to a cyclic structural group having an atom other than carbon such as furanyl, thienyl, oxazolyl, pyridyl, quinolinyl, and carbazolyl, which may be unsubstituted or substituted. The number of carbon atoms of the heterocyclic group is not particularly limited, but is usually in the range of 2 to 30.

Halogen refers to fluorine, chlorine, bromine, and iodine.

Formil, carbonyl, and amino can also include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles, and the like.

Further, the aliphatic hydrocarbon, the alicyclic hydrocarbon, the aromatic hydrocarbon, and the heterocycle may be substituted or substituted.

The silyl refers to a silicon compound group such as trimethylsilyl, which may be unsubstituted or substituted. The number of carbon atoms of silyl is not particularly limited, but is usually in the range of 3 to 20. The number of silicon is usually 1 to 6.

The fused rings formed between the adjacent substituents are, for example, Ar ¹ and R ² , Ar ¹ and R ³ , Ar ² and R ² , Ar ² and R ³ , R ² and R ³ , and Ar ¹ . It is a conjugated or non-conjugated fused ring formed between Ar ^{2 and the like.} Here, when n is 1, may be formed conjugated or non-conjugated fused ring with two of R ¹ each other. These fused rings may contain nitrogen, oxygen, and sulfur atoms in the ring structure, or may be condensed with another ring.

Specific examples of this phosphine oxide derivative include the following compounds.

This phosphine oxide derivative can be produced by using a known raw material and a known synthetic method.

<Pyrimidine derivative>
The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), preferably a compound represented by the following formula (ETM-8-1). Details are also described in International Publication No. 2011/021689.

Ar is an aryl which may be substituted or a heteroaryl which may be substituted independently of each other. n is an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 2 or 3.

Examples of the "aryl" of the "optionally substituted aryl" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, and more preferably aryls having 6 to 20 carbon atoms. More preferably, it is an aryl having 6 to 12 carbon atoms.

Specific examples of "aryl" include phenyl, which is a monocyclic aryl, biphenylyl (2-, 3-, 4-) biphenylyl, and (1-, 2-) naphthyl, which is a fused bicyclic aryl. , Tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o -Terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) , Condensed tricyclic aryl, acenaphthylene- (1-, 3-, 4-, 5-) yl, fluorene- (1-, 2-, 3-, 4-, 9-) yl, phenalene- (1) -, 2-) Il, (1-, 2-, 3-, 4-, 9-) phenanthryl, quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, which is a tetracyclic aryl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), triphenylene- (1-, 2), a fused tetracyclic aryl -) Ill, pyrene- (1-, 2-, 4-) yl, naphthacene- (1-, 2-, 5-) yl, perylene- (1-, 2-, 3-), which is a fused pentacyclic aryl ) Il, pentasen- (1-, 2-, 5-, 6-) il and the like.

Examples of the "heteroaryl" of the "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. Aryl is more preferable, heteroaryl having 2 to 15 carbon atoms is further preferable, and heteroaryl having 2 to 10 carbon atoms is particularly preferable. Examples of the heteroaryl include a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

Specific heteroaryls include, for example, frills, thienyl, pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, frazayl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, benzofuranyl, Isobenzofuranyl, benzo [b] thienyl, indrill, isoindrill, 1H-indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, synnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthylidine, prynyl. , Pteridinyl, carbazolyl, acridinyl, phenoxadinyl, phenothiazinyl, phenazinyl, phenoxatiinyl, thiantranyl, indridinyl and the like.

Further, the above-mentioned aryl and heteroaryl may be substituted, and may be substituted with, for example, the above-mentioned aryl and heteroaryl, respectively.

Specific examples of this pyrimidine derivative include the following compounds.

This pyrimidine derivative can be produced by using a known raw material and a known synthetic method.

<Aryl Nitrile Derivative>
The arylnitrile derivative is, for example, a compound represented by the following formula (ETM-9), or a multimer in which a plurality of the compounds are bonded by a single bond or the like. Details can be found in US Application Publication No. 2014/0197386.

Ar _ni preferably has a large number of carbon atoms from the viewpoint of fast electron transportability, and preferably has a small number of carbon atoms from the viewpoint of high T1. Specifically, Ar _ni is preferably a high T1 for use in a layer adjacent to the light emitting layer, is an aryl having 6 to 20 carbon atoms, and is preferably an aryl having 6 to 14 carbon atoms, more preferably. It is an aryl having 6 to 10 carbon atoms. Further, the number of substitutions n of the nitrile groups is preferably large from the viewpoint of high T1 and preferably small from the viewpoint of high S1. Specifically, the number of substitutions n of the nitrile group is an integer of 1 to 4, preferably an integer of 1 to 3, more preferably an integer of 1 to 2, and even more preferably 1.

Ar is an aryl which may be substituted or a heteroaryl which may be substituted independently of each other. From the viewpoint of high S1 and high T1, donor heteroaryl is preferable, and donor heteroaryl is preferably small because it is used as an electron transport layer. From the viewpoint of charge transportability, aryl or heteroaryl having a large number of carbon atoms is preferable, and it is preferable to have a large number of substituents. Specifically, the number of substitutions m of Ar is an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 1 to 2.

Examples of the "aryl" of the "optionally substituted aryl" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, and more preferably aryls having 6 to 20 carbon atoms. More preferably, it is an aryl having 6 to 12 carbon atoms.

Specific examples of "aryl" include phenyl, which is a monocyclic aryl, biphenylyl (2-, 3-, 4-) biphenylyl, and (1-, 2-) naphthyl, which is a fused bicyclic aryl. , Tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o -Terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) , Condensed tricyclic aryl, acenaphthylene- (1-, 3-, 4-, 5-) yl, fluorene- (1-, 2-, 3-, 4-, 9-) yl, phenalene- (1) -, 2-) Il, (1-, 2-, 3-, 4-, 9-) phenanthryl, quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, which is a tetracyclic aryl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), triphenylene- (1-, 2), a fused tetracyclic aryl -) Ill, pyrene- (1-, 2-, 4-) yl, naphthacene- (1-, 2-, 5-) yl, perylene- (1-, 2-, 3-), which is a fused pentacyclic aryl ) Il, pentasen- (1-, 2-, 5-, 6-) il and the like.

Examples of the "heteroaryl" of the "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. Aryl is more preferable, heteroaryl having 2 to 15 carbon atoms is further preferable, and heteroaryl having 2 to 10 carbon atoms is particularly preferable. Examples of the heteroaryl include a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

Specific heteroaryls include, for example, frills, thienyl, pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, frazayl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, benzofuranyl, Isobenzofuranyl, benzo [b] thienyl, indrill, isoindrill, 1H-indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, synnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthylidine, prynyl. , Pteridinyl, carbazolyl, acridinyl, phenoxadinyl, phenothiazinyl, phenazinyl, phenoxatiinyl, thiantranyl, indridinyl and the like.

Further, the above-mentioned aryl and heteroaryl may be substituted, and may be substituted with, for example, the above-mentioned aryl and heteroaryl, respectively.

The arylnitrile derivative may be a multimer in which a plurality of compounds represented by the formula (ETM-9) are bonded by a single bond or the like. In this case, in addition to the single bond, an aryl ring (preferably a polyvalent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring) may be bonded.

Specific examples of this arylnitrile derivative include the following compounds.

This arylnitrile derivative can be produced by using a known raw material and a known synthesis method.

<Triazine derivative>
The triazine derivative is, for example, a compound represented by the following formula (ETM-10), preferably a compound represented by the following formula (ETM-10-1). Details are described in US Application Publication No. 2011/015601.

Ar is an aryl which may be substituted or a heteroaryl which may be substituted independently of each other. n is an integer of 1-3, preferably 2 or 3.

Examples of the "aryl" of the "optionally substituted aryl" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, and more preferably aryls having 6 to 20 carbon atoms. More preferably, it is an aryl having 6 to 12 carbon atoms.

Specific examples of "aryl" include phenyl, which is a monocyclic aryl, biphenylyl (2-, 3-, 4-) biphenylyl, and (1-, 2-) naphthyl, which is a fused bicyclic aryl. , Tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o -Terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) , Condensed tricyclic aryl, acenaphthylene- (1-, 3-, 4-, 5-) yl, fluorene- (1-, 2-, 3-, 4-, 9-) yl, phenalene- (1) -, 2-) Il, (1-, 2-, 3-, 4-, 9-) phenanthryl, quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, which is a tetracyclic aryl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), triphenylene- (1-, 2), a fused tetracyclic aryl -) Ill, pyrene- (1-, 2-, 4-) yl, naphthacene- (1-, 2-, 5-) yl, perylene- (1-, 2-, 3-), which is a fused pentacyclic aryl ) Il, pentasen- (1-, 2-, 5-, 6-) il and the like.

Examples of the "heteroaryl" of the "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. Aryl is more preferable, heteroaryl having 2 to 15 carbon atoms is further preferable, and heteroaryl having 2 to 10 carbon atoms is particularly preferable. Examples of the heteroaryl include a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

Specific heteroaryls include, for example, frills, thienyl, pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, frazayl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, benzofuranyl, Isobenzofuranyl, benzo [b] thienyl, indrill, isoindrill, 1H-indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, synnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthylidine, prynyl. , Pteridinyl, carbazolyl, acridinyl, phenoxadinyl, phenothiazinyl, phenazinyl, phenoxatiinyl, thiantranyl, indridinyl and the like.

Further, the above-mentioned aryl and heteroaryl may be substituted, and may be substituted with, for example, the above-mentioned aryl and heteroaryl, respectively.

Specific examples of this triazine derivative include the following compounds.

This triazine derivative can be produced by using a known raw material and a known synthetic method.

<Benzimidazole derivative>
The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11).

φ is an n-valent aryl ring (preferably an n-valent benzene ring, a naphthalene ring, an anthracene ring, a fluorene ring, a benzfluorene ring, a phenanthrene ring, a phenanthrene ring or a triphenylene ring), and n is an integer of 1 to 4. Yes, in the "benzimidazole-based substituent", pyridyl in the "pyridine-based substituent" in the formula (ETM-2), the formula (ETM-2-1) and the formula (ETM-2-2) is replaced with benzimidazolyl. At least one hydrogen in the benzimidazole derivative may be substituted with dehydrogen.

^{R 11} in the above benzimidazolyl is hydrogen, alkyl having 1 to 24 carbon atoms, cycloalkyl or aryl having 6 to 30 carbon atoms having 3 to 12 carbon atoms, the formula (ETM-2-1) and formula (ETM-2 ^{The explanation of R 11} in -2) can be quoted.

φ is further preferably an anthracene ring or a fluorene ring, and the structure in this case can be quoted from the description in the formula (ETM-2-1) or the formula (ETM-2-2), and each formula can be cited. In R ^{11 to} R ¹⁸ , the explanation in the formula (ETM-2-1) or the formula (ETM-2-2) can be quoted. Further, in the formula (ETM-2-1) or the formula (ETM-2-2), two pyridine-based substituents are described in a bonded form, but when these are replaced with benzoimidazole-based substituents, both are described. The pyridine-based substituent may be replaced with a benzoimidazole-based substituent (that is, n = 2), or any one pyridine-based substituent may be replaced with a benzoimidazole-based substituent and the other pyridine-based substituent may be replaced with R ¹¹ to R 11 to It ^{may be replaced with R 18} (ie n = 1). ^{Further, for example, at least one of R 11 to} R ¹⁸ in the formula (ETM-2-1) may be replaced with a benzimidazole-based substituent, and the “pyridine-based substituent” may be replaced ^{with R 11 to} R ^18.

Specific examples of this benzimidazole derivative include, for example, 1-phenyl-2- (4- (10-phenylanthracene-9-yl) phenyl) -1H-benzo [d] imidazole, 2- (4- (10- (10-). Naphthalene-2-yl) anthracene-9-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole, 2- (3- (10- (naphthalen-2-yl) anthracene-9-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole, 5- (10- (naphthalene-2-yl) anthracene-9-yl) -1,2-diphenyl-1H-benzazole, 1- (4) -(10- (Naphthalene-2-yl) anthracene-9-yl) phenyl) -2-phenyl-1H-benzo [d] imidazole, 2- (4- (9,10-di (naphthalen-2-yl)) Anthracene-2-yl) phenyl) -1-phenyl-1H-benzazole, 1-(4- (9,10-di (naphthalene-2-yl) anthracene-2-yl) phenyl) -2- Examples thereof include phenyl-1H-benz [d] imidazole and 5- (9,10-di (naphthalen-2-yl) anthracene-2-yl) -1,2-diphenyl-1H-benzo [d] imidazole.

This benzimidazole derivative can be produced by using a known raw material and a known synthetic method.

<Phenanthroline derivative>
The phenanthroline derivative is, for example, a compound represented by the following formula (ETM-12) or formula (ETM-12-1). Details are described in International Publication No. 2006/021982.

φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4. be.

^{R 11 to} R ¹⁸ of each formula are independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably carbon number 3 to 12). The number 6 to 30 aryl). Further, in the formula (ETM-12-1), ^{any one of R 11 to} R ¹⁸ serves as a bond with φ, which is an aryl ring.

At least one hydrogen in each phenanthroline derivative may be substituted with deuterium.

Alkyl in R ¹¹ to R ^18, cycloalkyl and aryl may be cited to the description of ^R 11 ^{to R 18} in the formula (ETM-2). Further, in addition to the above-mentioned example, φ can be given, for example, the following structural formula. In addition, R in the following structural formula is hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl or terphenylyl independently, and * represents a binding position.

Specific examples of this phenanthroline derivative include, for example, 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di (1,10-). Phenanthroline-2-yl) anthracene, 2,6-di (1,10-phenanthroline-5-yl) pyridine, 1,3,5-tri (1,10-phenanthroline-5-yl) benzene, 9,9' -Difluoro-bi (1,10-phenanthroline-5-yl), bathocuproine, 1,3-bis (2-phenyl-1,10-phenanthroline-9-yl) benzene, compounds represented by the following structural formulas, etc. can give.

This phenanthroline derivative can be produced by using a known raw material and a known synthetic method.

式中、Ｒ^１〜Ｒ^６は、それぞれ独立して、水素、フッ素、アルキル、シクロアルキル、アラルキル、アルケニル、シアノ、アルコキシまたはアリールであり、ＭはＬｉ、Ａｌ、Ｇａ、ＢｅまたはＺｎであり、ｎは１〜３の整数である。 <Kinolinol-based metal complex>
The quinolinol-based metal complex is, for example, a compound represented by the following formula (ETM-13).

In the formula, R ^{1 to} R ⁶ are independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy or aryl, and M is Li, Al, Ga, Be or Zn. n is an integer of 1-3.

Specific examples of the quinolinol-based metal complex include 8-quinolinol lithium, tris (8-quinolinolate) aluminum, tris (4-methyl-8-quinolinolate) aluminum, tris (5-methyl-8-quinolinolate) aluminum, and tris (3). , 4-Dimethyl-8-quinolinolate) aluminum, tris (4,5-dimethyl-8-quinolinolate) aluminum, tris (4,5-dimethyl-8-quinolinolate) aluminum, bis (2-methyl-8-quinolinolate) ( Phenolate) Aluminum, bis (2-methyl-8-quinolinolate) (2-methylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-methylphenorate) aluminum, bis (2-methyl-8- Kinolinolate) (4-methylphenorate) aluminum, bis (2-methyl-8-quinolinolate) (2-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-phenylphenolate) aluminum, bis (2-Methyl-8-quinolinolate) (4-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,3-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolate) ( 2,6-Dimethylphenolate) Aluminum, bis (2-methyl-8-quinolinolate) (3,4-dimethylphenorate) Aluminum, bis (2-methyl-8-quinolinolate) (3,5-dimethylphenolate) Aluminum, bis (2-methyl-8-quinolinolate) (3,5-di-t-butylphenolate) Aluminum, bis (2-methyl-8-quinolinolate) (2,6-diphenylphenolate) Aluminum, bis ( 2-Methyl-8-quinolinolate) (2,4,6-triphenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,4,6-trimethylphenolate) aluminum, bis (2-methyl -8-quinolinolate) (2,4,5,6-tetramethylphenorate) aluminum, bis (2-methyl-8-quinolinolate) (1-naphtholate) aluminum, bis (2-methyl-8-quinolinolate) (2) -Naftrat) Aluminum, bis (2,4-dimethyl-8-quinolinolate) (2-phenylphenylate) Aluminum, bis (2,4-dimethyl-8-quinolinolate) ) (3-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (4-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-dimethylphenolate) Latte) Aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-di-t-butylphenolate) aluminum, bis (2-methyl-8-quinolinolate) aluminum-μ-oxo-bis (2) -Methyl-8-quinolinolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) aluminum-μ-oxo-bis (2,4-dimethyl-8-quinolinolate) aluminum, bis (2-methyl-4-ethyl) -8-Kinolinolate) Aluminum-μ-oxo-bis (2-methyl-4-ethyl-8-quinolinolate) Aluminum, bis (2-methyl-4-methoxy-8-quinolinolate) Aluminum-μ-oxo-bis (2) -Methyl-4-methoxy-8-quinolinolate) aluminum, bis (2-methyl-5-cyano-8-quinolinolate) aluminum-μ-oxo-bis (2-methyl-5-cyano-8-quinolinolate) aluminum, bis (2-Methyl-5-trifluoromethyl-8-quinolinolate) Aluminum-μ-oxo-bis (2-methyl-5-trifluoromethyl-8-quinolinolate) Aluminum, bis (10-hydroxybenzo [h] quinolinate) Berylium and the like can be mentioned.

This quinolinol-based metal complex can be produced by using a known raw material and a known synthesis method.

ベンゾチアゾール誘導体は、例えば下記式（ＥＴＭ−１４−２）で表される化合物である。

<Thiazole derivative and benzothiazole derivative>
The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1).

The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2).

Φ of each formula is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is 1 to 4 The "thiazole-based substituent" and "benzothiazole-based substituent" are the "pyridine-based substituents" in the formulas (ETM-2), (ETM-2-1) and (ETM-2-2). The pyridyl in the "group" is a substituent in which the following thiazolyl or benzothiazolyl is replaced, and at least one hydrogen in the thiazole derivative and the benzothiazole derivative may be substituted with dehydrogen.

φ is further preferably an anthracene ring or a fluorene ring, and the structure in this case can be quoted from the description in the formula (ETM-2-1) or the formula (ETM-2-2), and each formula can be cited. In R ^{11 to} R ¹⁸ , the explanation in the formula (ETM-2-1) or the formula (ETM-2-2) can be quoted. Further, in the formula (ETM-2-1) or the formula (ETM-2-2), two pyridine-based substituents are described in a bonded form, and these are described as a thiazole-based substituent (or a benzothiazole-based substituent). ), Both pyridine-based substituents may be replaced with a thiazole-based substituent (or benzothiazole-based substituent) (that is, n = 2), or any one of the pyridine-based substituents may be replaced with a thiazole-based substituent. It may be replaced with (or a benzothiazole-based substituent) and the other pyridine-based substituent ^{may be replaced with R 11 to} R ¹⁸ (that is, n = 1). ^{Further, for example, at least one of R 11 to} R ¹⁸ in the formula (ETM-2-1) is replaced with a thiazole-based substituent (or a benzothiazole-based substituent), and the "pyridine-based substituent" is replaced with R ^{11 to} R ¹⁸ . It may be replaced.

These thiazole derivatives or benzothiazole derivatives can be produced by using known raw materials and known synthetic methods.

<Siror derivative>
The siror derivative is, for example, a compound represented by the following formula (ETM-15). Details are described in JP-A-9-194487.

X and Y are independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, heteroaryl, which may be substituted. For details of these groups, the explanations in the formulas (1) and (2) and the explanations in the formula (ETM-7-2) can be cited. In addition, alkenyloxy and alkynyloxy are groups in which the alkyl moiety in alkoxy is replaced with alkenyl or alkynyl, respectively, and the details of these alkenyl and alkynyl can be referred to in the formula (ETM-7-2).
Further, X and Y may be bonded to form a cycloalkyl ring (and a ring in which a part thereof is unsaturated), and the details of the cycloalkyl ring are described in the formulas (1) and (2). You can refer to the description of cycloalkyl.

R ^{1 to} R ⁴ are independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, azo group, alkylcarbonyloxy, arylcarbonyl. Oxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, sulfanyl, silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate group, isocyanate group, thiocyanate group, It is an isothiocyanate group or a cyano, which may be substituted with an alkyl, cycloalkyl, aryl or halogen and may form a fused ring with an adjacent substituent.

In R ¹ to R ^4, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, details of the alkenyl and alkynyl can cite the description in Equation (1) and (2).

In R ¹ to R ^4, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, during alkoxycarbonyloxy and aryloxycarbonyloxy, alkyl, for the details of aryl and alkoxy, wherein The explanations in (1) and equation (2) can be cited.

Examples of the silyl include an unsubstituted silyl and a group in which at least one of the three hydrogens of the silyl is independently substituted with aryl, alkyl or cycloalkyl, and a tri-substituted silyl is preferable, and a triarylsilyl is preferable. , Trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl and the like. For details of aryl, alkyl and cycloalkyl in these, the explanations in formulas (1) and (2) can be cited.

The fused ring formed between the adjacent substituents is, for example, a conjugated or non-conjugated fused ring formed between ^{R 1} and R ² , R ² and R ³ , R ³ and R ^{4, and the like.} .. These fused rings may contain nitrogen, oxygen, and sulfur atoms in the ring structure, or may be condensed with another ring.

However, preferably, when R ¹ and R ⁴ are phenyl, X and Y are not alkyl or phenyl. Also, preferably, when R ¹ and R ⁴ are thienyl, X and Y are alkyl, and R ² and R ³ are alkyl, aryl, alkenyl or ^{cyclo in which R 2} and R ³ are bonded to form a ring. It is a structure that does not satisfy alkyl at the same time. Also, preferably, when R ¹ and R ⁴ are silyls, R ² , R ³ , X and Y are independently hydrogen or alkyl having 1 to 6 carbon atoms, respectively. Also, preferably, in the case of a structure in which benzene rings are condensed at ^{R 1} and R ^{2, X and Y are not alkyl and phenyl.}

These siror derivatives can be produced using known raw materials and known synthetic methods.

<Azolin derivative>
The azoline derivative is, for example, a compound represented by the following formula (ETM-16). Details are described in International Publication No. 2017/014226.

In formula (ETM-16),
φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen of φ has 1 carbon atom. It may be substituted with an alkyl of ~ 6, a cycloalkyl of 3-14 carbons, an aryl of 6-18 carbons or a heteroaryl of 2-18 carbons.
Y is independently of -O-, -S- or> N-Ar, where Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen of Ar. ^May be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and R ^{1 to} R 5 are independent of each other. Hydrogen, an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, however, ^{any one of Ar and R 1 to} R ⁵ in the above> N-Ar is bonded to L. It is a part to be
L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2).

In formula (L-1), X ^{1 to} X ⁶ are independently = CR ⁶ − or = N −, and at least two of ^{X 1 to} X ^{6 are = CR 6} −, and X ^{1 R 6} in two = CR ⁶ − of ~ X ⁶ is the site that binds to φ or the azoline ring, and ^{R 6} in the ^{other = CR 6} − is hydrogen.
In formula (L-2), X ^{7 to} X ¹⁴ are independently = CR ⁶ − or = N −, and at least two of ^{X 7 to} X ^{14 are = CR 6} −, and X ^{7 R 6} in two = CR ⁶ − of ~ X ¹⁴ is the site that binds to φ or the azoline ring, and ^{R 6} in the ^{other = CR 6} − is hydrogen.
At least one hydrogen of L may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 10 carbon atoms or a heteroaryl having 2 to 10 carbon atoms.
m is an integer of 1 to 4, and when m is 2 to 4, the groups formed by the azoline ring and L may be the same or different, and
At least one hydrogen in the compound represented by the formula (ETM-16) may be substituted with deuterium.

The specific azoline derivative is a compound represented by the following formula (ETM-16-1) or formula (ETM-16-2).

In the formula (ETM-16-1) and the formula (ETM-16-2),
φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen of φ has 1 carbon atom. It may be substituted with an alkyl of ~ 6, a cycloalkyl of 3-14 carbons, an aryl of 6-18 carbons or a heteroaryl of 2-18 carbons.
In formula (ETM-16-1), Y is independently -O-, -S- or> N-Ar, where Ar is an aryl having 6 to 12 carbon atoms or a hetero with 2 to 12 carbon atoms. It is an aryl, even if at least one hydrogen of Ar is substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms. Often,
In the formula (ETM-16-1), R ^{1 to} R ⁴ are independently hydrogen, an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, respectively, except that R ¹ and R ² are the same. And R ³ and R ⁴ are the same,
In the formula (ETM-16-2), R ^{1 to} R ⁵ are independently hydrogen, an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, respectively, except that R ¹ and R ² are the same. And R ³ and R ⁴ are the same,
In the formula (ETM-16-1) and the formula (ETM-16-2),
L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2).

In formula (L-1), X ^{1 to} X ⁶ are independently = CR ⁶ − or = N −, and at least two of ^{X 1 to} X ^{6 are = CR 6} −, and X ^{1 R 6} in two = CR ⁶ − of ~ X ⁶ is the site that binds to φ or the azoline ring, and ^{R 6} in the ^{other = CR 6} − is hydrogen.
In formula (L-2), X ^{7 to} X ¹⁴ are independently = CR ⁶ − or = N −, and at least two of ^{X 7 to} X ^{14 are = CR 6} −, and X ^{7 R 6} in two = CR ⁶ − of ~ X ¹⁴ is the site that binds to φ or the azoline ring, and ^{R 6} in the ^{other = CR 6} − is hydrogen.
At least one hydrogen of L may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 10 carbon atoms or a heteroaryl having 2 to 10 carbon atoms.
m is an integer of 1 to 4, and when m is 2 to 4, the groups formed by the azoline ring and L may be the same or different, and
At least one hydrogen in the compound represented by the formula (ETM-16-1) or the formula (ETM-16-2) may be substituted with deuterium.

Preferably, φ is a monovalent group represented by the following formulas (φ1-1) to (φ1-18) and a divalent group represented by the following formulas (φ2-1) to (φ2-34). It consists of a trivalent group represented by the following formulas (φ3-1) to (φ3-3) and a tetravalent group represented by the following formulas (φ4-1) to (φ4-2). Selected from the group, at least one hydrogen of φ is substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, an aryl having 6 to 18 carbon atoms or a heteroaryl having 2 to 18 carbon atoms. May be good.

Z in the formula is> CR ₂ ,>N-Ar,> N-L, -O- or -S-, and _{R in> CR 2} is an alkyl having 1 to 4 carbon atoms, respectively. It is a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and R may be bonded to each other to form a ring, and Ar in> N-Ar is It is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and L in> NL is the formula (ETM-16), the formula (ETM-16-1) or the formula (ETM-16-2). Is L in. * In the formula represents the connection position.

Preferably, L is a divalent group of rings selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthylidine, phthalazine, quinoxaline, quinazoline, cinnoline, and pteridine. At least one hydrogen of L may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 10 carbon atoms or a heteroaryl having 2 to 10 carbon atoms.

Preferably, Ar in> N-Ar as Y or Z consists of the group consisting of phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridadinyl, triazinyl, quinolinyl, isoquinolinyl, naphthyldinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, and pteridinyl. Selected, at least one hydrogen of Ar in> N—Ar as Y may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms or an aryl having 6 to 10 carbon atoms.

Preferably, R ^{1 to} R ⁴ are independently hydrogen, an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, where R ¹ and R ² are the same, and R ³ and R are R 3 and R. ⁴ is the same, and ^{not all of R 1 to} R ⁴ are hydrogen at the same time, and when m is 1 or 2 and m is 2, the group formed by the azoline ring and L. Are the same.

Specific examples of the azoline derivative include the following compounds. In addition, "Me" in the structural formula represents methyl.

More preferably, φ is a divalent group represented by the following formula (φ2-1), formula (φ2-31), formula (φ2-32), formula (φ2-33) and formula (φ2-34). Selected from the group consisting of, at least one hydrogen of φ may be substituted with an aryl having 6 to 18 carbon atoms.

L is a divalent group of a ring selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine, and triazine, and at least one hydrogen of L is an alkyl having 1 to 4 carbon atoms and 5 to 4 carbon atoms. It may be substituted with 10 cycloalkyl, an aryl having 6 to 10 carbon atoms or a heteroaryl having 2 to 14 carbon atoms.
Ar in> N-Ar as Y is selected from the group consisting of phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridadinyl, and triazinyl, and at least one hydrogen of the Ar is an alkyl having 1 to 4 carbon atoms and 5 to 5 carbon atoms. It may be substituted with 10 cycloalkyl or an aryl having 6 to 10 carbon atoms.
R ^{1 to} R ⁴ are independently hydrogen, alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, where R ¹ and R ² are the same, and R ³ and R ⁴ are the same. , and the addition of all of ^R 1 to R ⁴ are not simultaneously hydrogen, and,
m is 2, and the groups formed by the azoline ring and L are the same.

Other specific examples of the azoline derivative include, for example, the following compounds. In addition, "Me" in the structural formula represents methyl.

For details of alkyl, cycloalkyl, aryl or heteroaryl in each of the above formulas defining this azoline derivative, the explanations in formulas (1) and (2) can be cited.

This azoline derivative can be produced by using a known raw material and a known synthesis method.

<Reducing substance>
The electron transport layer or electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or electron injection layer. As this reducing substance, various substances are used as long as they have a certain reducing property. For example, alkali metal, alkaline earth metal, rare earth metal, alkali metal oxide, alkali metal halide, alkali. From the group consisting of earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes At least one selected can be preferably used.

Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV) or Cs (1.95 eV), and Ca (2.95 eV). Alkali earth metals such as 9 eV), Sr (2.0 to 2.5 eV) or Ba (2.52 eV) are mentioned, and those having a work function of 2.9 eV or less are particularly preferable. Of these, the more preferable reducing substance is an alkali metal of K, Rb or Cs, more preferably Rb or Cs, and most preferably Cs. These alkali metals have a particularly high reducing ability, and by adding a relatively small amount to the material forming the electron transport layer or the electron injection layer, the emission brightness and the life of the organic EL device can be extended. Further, as a reducing substance having a work function of 2.9 eV or less, a combination of these two or more kinds of alkali metals is also preferable, and in particular, a combination containing Cs, for example, Cs and Na, Cs and K, Cs and Rb, or A combination of Cs, Na and K is preferred. By containing Cs, the reducing ability can be efficiently exhibited, and by adding to the material forming the electron transport layer or the electron injection layer, the emission brightness and the life of the organic EL device can be improved.

3. 3. The substrate 101 of the organic electroluminescent element serves as a support for the organic EL element 100, and usually quartz, glass, metal, plastic, or the like is used. The substrate 101 is formed in a plate shape, a film shape, or a sheet shape depending on the purpose, and for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used. Of these, a glass plate and a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferable. As for the glass substrate, soda lime glass, non-alkali glass, or the like is used, and the thickness may be sufficient to maintain the mechanical strength. Therefore, for example, 0.2 mm or more may be used. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. As for the material of the glass, non-alkali glass is preferable because it is better that there are few elution ions from the glass, but _{soda lime glass with a barrier coat such as SiO 2} is also commercially available, so this can be used. can. Further, in order to enhance the gas barrier property, the substrate 101 may be provided with a gas barrier film such as a dense silicon oxide film on at least one side, and a synthetic resin plate, film or sheet having a particularly low gas barrier property may be used as the substrate 101. When used, it is preferable to provide a gas barrier film.

4. The anode-anode 102 in the organic electroluminescent device plays a role of injecting holes into the light emitting layer 105. When the hole injection layer 103 and / or the hole transport layer 104 is provided between the anode 102 and the light emitting layer 105, holes are injected into the light emitting layer 105 through these. ..

Examples of the material forming the anode 102 include an inorganic compound and an organic compound. Examples of the inorganic compound include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxidation, etc.). (IZO, etc.), metals halide (copper iodide, etc.), copper sulfide, carbon black, ITO glass, nesa glass, etc. Examples of the organic compound include polythiophene such as poly (3-methylthiophene) and conductive polymers such as polypyrrole and polyaniline. In addition, it can be appropriately selected and used from the substances used as the anode of the organic EL element.

The resistance of the transparent electrode is not limited as long as a sufficient current can be supplied to emit light from the light emitting element, but it is desirable that the resistance is low from the viewpoint of power consumption of the light emitting element. For example, an ITO substrate of 300 Ω / □ or less functions as an element electrode, but since it is now possible to supply a substrate of about 10 Ω / □, for example, 100 to 5 Ω / □, preferably 50 to 5 Ω. It is especially desirable to use a low resistance product of / □. The thickness of ITO can be arbitrarily selected according to the resistance value, but it is usually used in the range of 50 to 300 nm.

5. Hole injection layer and hole transport layer in the organic electroluminescent device The hole injection layer 103 plays a role of efficiently injecting holes moving from the anode 102 into the light emitting layer 105 or the hole transport layer 104. It will be fulfilled. The hole transport layer 104 plays a role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 via the hole injection layer 103 to the light emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are formed by laminating and mixing one or more of the hole injection / transport materials or a mixture of the hole injection / transport material and the polymer binder, respectively. Will be done. Further, an inorganic salt such as iron (III) chloride may be added to the hole injection / transport material to form a layer.

As a hole injection / transporting substance, it is necessary to efficiently inject / transport holes from the positive electrode between electrodes to which an electric field is applied, and the hole injection efficiency is high, and the injected holes are efficiently transported. It is desirable to do. For that purpose, it is preferable that the substance has a small ionization potential, a large hole mobility, excellent stability, and is less likely to generate trap impurities during production and use.

Examples of the material forming the hole injection layer 103 and the hole transport layer 104 include a compound, a p-type semiconductor, and a hole injection layer of an organic EL element that have been conventionally used as a hole charge transport material in a photoconductive material. And any known material used for the hole transport layer can be selected and used. Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis (N-arylcarbazole) or bis (N-alkylcarbazole), and triarylamine derivatives (aromatic tertiary). Polymers with amino in the main or side chains, 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane, N, N'-diphenyl-N, N'-di (3-methylphenyl) -4 , 4'-diaminobiphenyl, N, N'-diphenyl-N, N'-dinaphthyl-4,4'-diaminobiphenyl, N, N'-diphenyl-N, N'-di (3-methylphenyl) -4 , 4'-diphenyl-1,1'-diamine, N, N'-dinaphthyl -N, ^{N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N} 4, N ^{4 '-} diphenyl - N ^4, N ^{4 '-} bis (9-phenyl -9H- carbazol-3-yl) - [1,1'-biphenyl] ^{-4,4'-diamine, N 4, N 4, N} 4', N 4 ^' -Tetra [1,1'-biphenyl] -4-yl)-[1,1'-biphenyl] -4,4'-diamine, 4,4', 4 "-tris (3-methylphenyl (phenyl) Amino) triphenylamine, N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-N- (4- (9-phenyl-9H-carbazole-3-yl) phenyl)- 9H-fluoren-2-amine, N, N-bis (4- (dibenzo [b, d] furan-4-yl) phenyl)-[1,1': 4', 1 "-terphenyl] -4- Triphenylamine derivatives such as amines, starburstamine derivatives, etc.), stillben derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives and thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives ( For example, 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile), heterocyclic compounds such as porphyrin derivatives, polysilanes and the like. In the polymer system, polycarbonate or styrene derivative having the monomer in the side chain, polyvinylcarbazole, polysilane, etc. are preferable, but a thin film necessary for producing a light emitting element can be formed, holes can be injected from the anode, and holes can be further injected. The compound is not particularly limited as long as it can transport the compound.

It is also known that the conductivity of organic semiconductors is strongly affected by its doping. Such an organic semiconductor matrix substance is composed of a compound having a good electron donating property or a compound having a good electron accepting property. Strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known for doping electron donors. (For example, the document "M.Pfeiffer, A.Beyer, T.Fritz, K.Leo, Appl.Phys.Lett., 73 (22), 3202-3204 (1998)" and the document "J. Blochwitz, M." See .Pfeiffer, T.Fritz, K.Leo, Appl.Phys.Lett., 73 (6), 729-731 (1998) "). They generate so-called holes by an electron transfer process in an electron-donating base material (hole-transporting material). Depending on the number of holes and the mobility, the conductivity of the base material changes considerably. Known matrix materials having hole transport properties include, for example, benzidine derivatives (TPD, etc.) or starburst amine derivatives (TDATA, etc.), or specific metal phthalocyanines (particularly zinc phthalocyanines (ZnPc), etc.) (such as zinc phthalocyanines). Japanese Unexamined Patent Publication No. 2005-167175).

6. The cathode and cathode 108 in the organic electroluminescent device plays a role of injecting electrons into the light emitting layer 105 via the electron injection layer 107 and the electron transport layer 106.

The material for forming the cathode 108 is not particularly limited as long as it is a substance capable of efficiently injecting electrons into the organic layer, but a material similar to the material for forming the anode 102 can be used. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium and magnesium or their alloys (magnesium-silver alloy, magnesium). -Indium alloys, aluminum-lithium alloys such as lithium fluoride / aluminum, etc.) are preferred. Alloys containing lithium, sodium, potassium, cesium, calcium, magnesium or these low work function metals are effective for increasing electron injection efficiency and improving device characteristics. However, these low work function metals are generally often unstable in the atmosphere. In order to improve this point, for example, a method of doping an organic layer with a trace amount of lithium, cesium or magnesium and using a highly stable electrode is known. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide and cesium oxide can also be used. However, it is not limited to these.

In addition, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium for electrode protection, or alloys using these metals, and inorganic substances such as silica, titania and silicon nitride, polyvinyl alcohol, vinyl chloride. , Laminating a hydrocarbon-based polymer compound or the like is given as a preferable example. The method for producing these electrodes is also not particularly limited as long as conduction can be obtained, such as resistance heating, electron beam deposition, sputtering, ion plating and coating.

7. The materials used for the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, and the electron injection layer, which may be used in each layer of the organic electric field light emitting element, can form each layer independently. However, as polymer binders, polyvinyl chloride, polycarbonate, polystyrene, poly (N-vinylcarbazole), polymethylmethacrylate, polybutylmethacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin. , Polyethylene, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin and other solvent-soluble resins, phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, etc. It is also possible to disperse it in a curable resin or the like.

<< Manufacturing method of organic electroluminescent device >>
Each layer constituting the organic EL element is made of a material to be formed of each layer, such as a vapor deposition method, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, printing method, inkjet method, spin coating method or casting method, coating method, etc. It can be formed by forming a thin film by the method. The film thickness of each layer thus formed is not particularly limited and can be appropriately set according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured with a crystal oscillation type film thickness measuring device or the like. When a thin film is formed by using a thin film deposition method, the vapor deposition conditions differ depending on the type of material, the target crystal structure and association structure of the film, and the like. The vapor deposition conditions are generally: boat heating temperature +50 to + 400 ° C., vacuum degree ^10-6 to ^10-3 Pa, vapor deposition rate 0.01 to 50 nm / sec, substrate temperature -150 to + 300 ° C., film thickness 2 nm to 5 μm. It is preferable to set appropriately within the range.

Next, as an example of a method for producing an organic EL device, an organic EL device composed of an anode / a hole injection layer / a hole transport layer / a light emitting layer composed of a host material and a dopant material / an electron transport layer / an electron injection layer / a cathode. The manufacturing method of the above will be described. A thin film of an anode material is formed on an appropriate substrate by a vapor deposition method or the like to prepare an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. A host material and a dopant material are co-deposited on this to form a thin film to form a light emitting layer, an electron transport layer and an electron injection layer are formed on the light emitting layer, and a thin film made of a cathode material is formed by a vapor deposition method or the like. By forming the cathode into a cathode, the desired organic EL element can be obtained. In the above-mentioned production of the organic EL element, the production order can be reversed, and the cathode, the electron injection layer, the electron transport layer, the light emitting layer, the hole transport layer, the hole injection layer, and the anode can be manufactured in this order. Is.

When a DC voltage is applied to the organic EL element thus obtained, the anode may be applied with a positive polarity and the cathode may be applied with a negative polarity, and when a voltage of about 2 to 40 V is applied, a transparent or translucent electrode is applied. Emission can be observed from the side (anode or cathode, or both). The organic EL element also emits light when a pulse current or an alternating current is applied. The waveform of the alternating current to be applied may be arbitrary.

<< Application example of organic electroluminescent device >>
The present invention can also be applied to a display device provided with an organic EL element, a lighting device provided with an organic EL element, and the like.
A display device or a lighting device provided with an organic EL element can be manufactured by a known method such as connecting an organic EL element according to the present embodiment to a known drive device, and can be manufactured by a known method such as DC drive, pulse drive, AC drive, or the like. It can be driven by using a known driving method as appropriate.

Examples of the display device include a panel display such as a color flat panel display and a flexible display such as a flexible color organic electroluminescent (EL) display (for example, JP-A-10-335066 and JP-A-2003-321546). (See Japanese Patent Application Laid-Open No. 2004-281806, etc.). Moreover, as a display system of a display, for example, a matrix and / or a segment system and the like can be mentioned. The matrix display and the segment display may coexist in the same panel.

The matrix means that the pixels for display are arranged two-dimensionally such as in a grid pattern or a mosaic pattern, and characters and images are displayed as a set of pixels. The shape and size of the pixels are determined by the application. For example, for displaying images and characters on a personal computer, monitor, or television, quadrangular pixels with a side of 300 μm or less are usually used, and in the case of a large display such as a display panel, pixels with a side on the order of mm should be used. become. In the case of monochrome display, pixels of the same color may be arranged, but in the case of color display, red, green, and blue pixels are displayed side by side. In this case, there are typically a delta type and a stripe type. Then, as the driving method of this matrix, either a line sequential driving method or an active matrix may be used. Line sequential drive has the advantage of a simpler structure, but when considering operating characteristics, the active matrix may be superior, so it is also necessary to use it properly depending on the application.

In the segment method (type), a pattern is formed so as to display predetermined information, and a predetermined area is made to emit light. Examples include time and temperature displays on digital clocks and thermometers, operating status displays of audio equipment and electromagnetic cookers, and panel displays of automobiles.

Examples of the lighting device include a lighting device such as an indoor lighting device, a backlight of a liquid crystal display device, and the like (for example, JP-A-2003-257621, JP-A-2003-277741, JP-A-2004-119211). Etc.). The backlight is mainly used for the purpose of improving the visibility of a display device that does not emit light by itself, and is used for a liquid crystal display device, a clock, an audio device, an automobile panel, a display board, a sign, and the like. In particular, as a backlight for liquid crystal display devices, especially for personal computers, for which thinning is an issue, considering that it is difficult to thin the backlight because the conventional type is composed of a fluorescent lamp and a light guide plate. The backlight using the light emitting element according to the embodiment is characterized by being thin and lightweight.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited thereto. First, an example of synthesizing the compound used in the examples will be described below.

Synthesis example (1-1): Synthesis of compound (1-1)

Compound (1-1) was synthesized according to the method described in WO 2006/003842.

Synthesis example (1-2): Synthesis of compound (1-12)

Compound (1-12) was synthesized according to the method described in WO 2006/003842.

Synthesis example (1-3): Synthesis of compound (1-16)

Compound (1-16) was synthesized according to the method described in WO 2006/003842.

Synthesis example (1-4): Synthesis of compound (1-47)

Compound (1-47) was synthesized according to the method described in WO 2006/003842.

Synthesis example (1-5): Synthesis of compound (1-153)

Compound (1-153) was synthesized according to the method described in WO 2006/003842.

Synthesis example (1-6): Synthesis of compound (1-255)

Compound (1-255) was synthesized according to the method described in WO 2006/003842.

Synthesis example (1-7): Synthesis of compound (1-263)

Compound (1-263) was synthesized according to the method described in WO 2006/003842.

Synthesis example (1-8): Synthesis of compound (1-319)

Compound (1-319) was synthesized according to the method described in WO 2006/003842.

Synthesis example (1-9): Synthesis of compound (1-454)

Compound (1-454) was synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 496.

Synthesis example (1-10): Synthesis of compound (1-457)

Compound (1-457) was synthesized by appropriately modifying the compound as a raw material of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 596.

Synthesis example (1-11): Synthesis of compound (1-456)

Compound (1-456) was synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 596.

Synthesis example (1-12): Synthesis of compound (1-490)

Compound (1-490) was synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 546.

Synthesis example (1-13): Synthesis of compound (1-493)

Compound (1-493) was synthesized by appropriately modifying the compound as a raw material of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 646.

Synthesis example (1-14): Synthesis of compound (1-492)

Compound (1-492) was synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 646.

Synthesis example (1-15): Synthesis of compound (1-641)

Compound (1-641) was synthesized according to the method described in WO 2009/142230.

Synthesis example (1-16): Synthesis of compound (1-646)

Compound (1-646) was synthesized according to the method described in WO 2009/142230.

Synthesis example (1-17): Synthesis of compound (1-649)

Compound (1-649) was synthesized according to the method described in WO 2009/142230.

Synthesis example (1-18): Synthesis of compound (1-640)

Compound (1-640) was synthesized according to the method described in WO 2009/142230.

Synthesis example (1-19): Synthesis of compound (1-535)

Compound (1-535) was synthesized according to the method described in WO 2009/142230.

Synthesis example (1-20): Synthesis of compound (1-534)

Compound (1-534) was synthesized according to the method described in WO 2009/142230.

Synthesis example (1-21): Synthesis of compound (1-677)

Compound (1-677) was synthesized by appropriately modifying the compound of the raw material of the method described in WO 2009/142230. EI-MS: m / z = 708.

Synthesis example (1-22): Synthesis of compound (1-682)

Compound (1-682) was synthesized by appropriately modifying the compound of the raw material of the method described in WO 2009/142230. EI-MS: m / z = 784.

Synthesis example (1-23): Synthesis of compound (1-1334)

Compound (1-1334) was synthesized according to the method described in Korean Publication No. 2017-116885. EI-MS: m / z = 587.

Synthesis Example (1-24): Synthesis of compound (1-1336)

Compound (1-1336) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 637.

Synthesis example (1-25): Synthesis of compound (1-279)

Compound (1-279) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 737.

Synthesis example (1-26): Synthesis of compound (1-125)

Compound (1-125) was synthesized according to the method described in WO 2006/003842.

Synthesis example (1-27): Synthesis of compound (1-155)

Compound (1-155) was synthesized according to the method described in WO 2006/003842.

Synthesis example (1-28): Synthesis of compound (1-29)

Compound (1-29) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 587.

Synthesis Example (1-29): Synthesis of compound (1-276)

Compound (1-276) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 637.

Synthesis example (1-30): Synthesis of compound (1-448)

Compound (1-448) was synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 671.

Synthesis example (1-31): Synthesis of compound (1-13)

Compound (1-13) was synthesized by appropriately modifying the compound as a raw material of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 658.

Synthesis example (1-32): Synthesis of compound (1-287)

Compound (1-287) was synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 532.

Synthesis example (1-33): Synthesis of compound (1-124)

Compound (1-124) was synthesized by appropriately modifying the compound as a raw material of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 482.

Synthesis example (1-34): Synthesis of compound (1-4)

Compound (1-4) was synthesized by appropriately modifying the compound as a raw material of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 558.

Synthesis example (1-35): Synthesis of compound (1-807)

Compound (1-807) was synthesized by appropriately modifying the compound as a raw material of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 546.

Synthesis example (1-36): Synthesis of compound (1-802)

Compound (1-802) was synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 496.

Synthesis example (1-37): Synthesis of compound (1-2400)

Compound (1-2400) was synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 532.

Synthesis example (1-38): Synthesis of compound (1-2401)

Compound (1-2401) was synthesized by appropriately modifying the compound as a raw material of the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 482.

Synthesis Example (1-39): Synthesis of Compound (1-4133) Compound (1-4133) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 609.

Synthesis Example (1-40): Synthesis of Compound (1-148) Compound (1-148) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 533.

Synthesis Example (1-41): Synthesis of Compound (1-150) Compound (1-150) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 633.

Synthesis Example (1-42): Synthesis of Compound (1-136) Compound (1-136) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 533.

Synthesis Example (1-43): Synthesis of Compound (1-4155) Compound (1-4155) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 583.

Synthesis Example (1-44): Synthesis of Compound (1-3268) Compound (1-3268) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 573.

Synthesis Example (1-45): Synthesis of Compound (1-4114) Compound (1-4114) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 573.

Synthesis Example (1-46): Synthesis of Compound (1-4121) Compound (1-4121) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 573.

Synthesis Example (1-47): Synthesis of Compound (1-4119) Compound (1-4119) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 573.

Synthesis Example (1-48): Synthesis of Compound (1-4120) Compound (1-4120) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 663.

Synthesis Example (1-49): Synthesis of Compound (1-4107) Compound (1-4107) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 663.

Synthesis Example (1-50): Synthesis of Compound (1-4317) Compound (1-4317) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 583.

Synthesis Example (1-51): Synthesis of Compound (1-4327) Compound (1-4327) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 633.

Synthesis Example (1-52): Synthesis of Compound (1-3991) Compound (1-3991) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 573.

Synthesis Example (1-53): Synthesis of Compound (1-2984) Compound (1-2984) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 573.

Synthesis Example (1-54): Synthesis of Compound (1-3452) Compound (1-3452) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 649.

Synthesis Example (1-55): Synthesis of Compound (1-2883) Compound (1-2883) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 649.

Synthesis Example (1-56): Synthesis of Compound (1-4205) Under a nitrogen atmosphere, the intermediate (I-2) (1.0 g) was dissolved in toluene (100 ml) to dissolve the intermediate (I-1) (1). .0 g), potassium carbonate (1.4 g), tetrabutylammonium bromide (TBAB, 0.4 g) and bis (di-t-butyl (4-dimethylaminophenyl) phosphine) dichloropalladium (Pd-132, 0.35 g) Was added, and the mixture was stirred under heating and reflux for 5 hours. After the reaction, water was added to the reaction solution to stop the reaction, toluene was further added to perform liquid separation extraction, and then the organic layer was concentrated to obtain a crude product. The obtained crude product was purified by a silica gel short column (eluent: chlorobenzene) to obtain compound (1-4205) (0.85 g). EI-MS: m / z = 608.

Synthesis Example (1-57): Synthesis of Compound (1-4232) Compound (1-4232) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 658.

Synthesis Example (1-58): Synthesis of Compound (1-4219) Compound (1-4219) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 608.

Synthesis Example (1-59): Synthesis of Compound (1-4254) Compound (1-4254) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 634.

Synthesis Example (1-60): Synthesis of Compound (1-4263) Compound (1-4263) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 658.

Synthesis Example (1-61): Synthesis of Compound (1-4271) Compound (1-4271) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 708.

Synthesis Example (1-62): Synthesis of Compound (1-2995) Compound (1-2995) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 648.

Synthesis Example (1-63): Synthesis of Compound (1-3005) Compound (1-3005) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 648.

Synthesis Example (1-64): Synthesis of Compound (1-3020) Compound (1-3020) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 750.

Synthesis Example (1-65): Synthesis of Compound (1-4204) Compound (1-4204) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 708.

Synthesis Example (1-66): Synthesis of Compound (1-4198) Compound (1-4198) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 788.

Synthesis Example (1-67): Synthesis of Compound (1-4280) Compound (1-4280) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 734.

Synthesis Example (1-68): Synthesis of Compound (1-3821) Compound (1-3821) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 838.

Synthesis Example (1-69): Synthesis of Compound (1-3078) Compound (1-3078) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 648.

Synthesis Example (1-70): Synthesis of Compound (1-4209) Compound (1-4209) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 658.

Synthesis Example (1-71): Synthesis of Compound (1-4093) Compound (1-4093) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 609.

Synthesis Example (1-72): Synthesis of Compound (1-4092) Compound (1-4092) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 811.

Synthesis Example (1-73): Synthesis of Compound (1-2977) Compound (1-2977) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 699.

Synthesis Example (1-74): Synthesis of Compound (1-4036) Compound (1-4036) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 649.

Synthesis Example (1-75): Synthesis of Compound (1-4335) Compound (1-4335) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 609.

Synthesis Example (1-76): Synthesis of Compound (1-4347) Compound (1-4347) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 609.

Synthesis Example (1-77): Synthesis of Compound (1-4354) Compound (1-4354) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 659.

Synthesis Example (1-78): Synthesis of Compound (1-3751) Compound (1-3751) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 649.

Synthesis Example (1-79): Synthesis of Compound (1-4106) Compound (1-4106) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 609.

Synthesis Example (1-80): Synthesis of Compound (1-3830) Compound (1-3830) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 533.

Synthesis Example (1-81): Synthesis of Compound (1-3839) Compound (1-3839) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 533.

Synthesis Example (1-82): Synthesis of Compound (1-4381) Compound (1-4381) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 583.

Synthesis Example (1-83): Synthesis of Compound (1-4390) Compound (1-4390) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 633.

Synthesis Example (1-84): Synthesis of Compound (1-3837) Compound (1-3837) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 713.

Synthesis Example (1-85): Synthesis of Compound (1-4091) Compound (1-4091) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 533.

Synthesis Example (1-86): Synthesis of Compound (1-3859) Compound (1-3859) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 583.

Synthesis Example (1-87): Synthesis of Compound (1-2416) Compound (1-2416) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2019-0563338. did. EI-MS: m / z = 583.

Synthesis Example (1-88): Synthesis of Compound (1-2495) Compound (1-2495) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2019-0563338. did. EI-MS: m / z = 749.

Synthesis Example (1-89): Synthesis of Compound (1-2404) Compound (1-2404) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2019-0563338. did. EI-MS: m / z = 673.

Synthesis Example (1-90): Synthesis of Compound (1-2440) Compound (1-2440) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2019-0563338. did. EI-MS: m / z = 965.

Synthesis Example (1-91): Synthesis of Compound (1-2499) Compound (1-2499) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2019-0563338. did. EI-MS: m / z = 749.

Synthesis Example (1-92): Synthesis of Compound (1-2413) Compound (1-2413) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2019-0563338. did. EI-MS: m / z = 723.

Synthesis Example (1-93): Synthesis of Compound (1-2520) Compound (1-2520) was synthesized by the method described in Korean Patent Publication No. 2010-007791. EI-MS: m / z = 659.

Synthesis Example (1-94): Synthesis of Compound (1-2516) Compound (1-2516) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2010-007791. did. EI-MS: m / z = 839.

Synthesis Example (1-95): Synthesis of Compound (1-2519) Compound (1-2519) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2010-007791. did. EI-MS: m / z = 749.

Synthesis Example (1-96): Synthesis of Compound (1-2525) Compound (1-2525) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2010-007791. did. EI-MS: m / z = 749.

Synthesis Example (1-97): Synthesis of Compound (1-2541) Compound (1-2541) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 659.

Synthesis Example (1-98): Synthesis of Compound (1-2557) Compound (1-2557) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 659.

Synthesis Example (1-99): Synthesis of Compound (1-2573) Compound (1-2573) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 709.

Synthesis Example (1-100): Synthesis of Compound (1-2586) Compound (1-2586) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 709.

Synthesis Example (1-101): Synthesis of Compound (1-2594) Compound (1-2594) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 709.

Synthesis Example (1-102): Synthesis of Compound (1-2599) Compound (1-2599) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 709.

Synthesis Example (1-103): Synthesis of Compound (1-2728) Compound (1-2728) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 749.

Synthesis Example (1-104): Synthesis of Compound (1-2579) Compound (1-2579) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 889.

Synthesis Example (1-105): Synthesis of Compound (1-2696) Compound (1-2696) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 889.

Synthesis Example (1-106): Synthesis of Compound (1-2738) Compound (1-2738) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 799.

Synthesis Example (1-107): Synthesis of Compound (1-2743) Compound (1-2743) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 799.

Synthesis Example (1-108): Synthesis of Compound (1-2699) Compound (1-2699) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 1041.

Synthesis Example (1-109): Synthesis of Compound (1-2603) Compound (1-2603) was synthesized by the method described in Korean Patent Publication No. 2018-0131963. EI-MS: m / z = 749.

Synthesis Example (1-110): Synthesis of Compound (1-2756) Compound (1-2756) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2018-0131963. did. EI-MS: m / z = 925.

Synthesis Example (1-111): Synthesis of Compound (1-2627) Compound (1-2627) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2018-0131963. did. EI-MS: m / z = 749.

Synthesis Example (1-112): Synthesis of Compound (1-2757) Compound (1-2757) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2018-0131963. did. EI-MS: m / z = 799.

Synthesis Example (1-113): Synthesis of Compound (1-2686) Compound (1-2686) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2018-0131963. did. EI-MS: m / z = 749.

Synthesis Example (1-114): Synthesis of Compound (1-2615) Compound (1-2615) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2018-0131963. did. EI-MS: m / z = 749.

Synthesis Example (1-115): Synthesis of Compound (1-2640) Compound (1-2640) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2018-0131963. did. EI-MS: m / z = 749.

Synthesis Example (1-116): Synthesis of Compound (1-2747) Compound (1-2747) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2018-0131963. did. EI-MS: m / z = 839.

Synthesis Example (1-117): Synthesis of Compound (1-2641) Compound (1-2641) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2018-0131963. did. EI-MS: m / z = 929.

Synthesis Example (1-118): Synthesis of compound (1-2775) Compound (1-2775) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 735.

Synthesis Example (1-119): Synthesis of compound (1-2779) Compound (1-2779) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 735.

Synthesis Example (1-120): Synthesis of Compound (1-2787) Compound (1-2787) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 785.

Synthesis Example (1-121): Synthesis of compound (1-2776) Compound (1-2776) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 915.

Synthesis Example (1-212): Synthesis of Compound (1-2812) Compound (1-2812) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 825.

Synthesis Example (1-123): Synthesis of Compound (1-3914) Compound (1-3914) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 659.

Synthesis Example (1-124): Synthesis of compound (1-3951) Compound (1-3951) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 749.

Synthesis Example (1-125): Synthesis of Compound (1-3903) Compound (1-3903) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 659.

Synthesis Example (1-126): Synthesis of Compound (1-1335) Compound (1-1335) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 587.

Synthesis Example (1-127): Synthesis of Compound (1-1337) Compound (1-1337) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 637.

Synthesis Example (1-128): Synthesis of compound (1-28) Compound (1-28) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 587.

Synthesis Example (1-129): Synthesis of compound (1-275) Compound (1-275) was synthesized according to the method described in Korean Patent Publication No. 2017-116885. EI-MS: m / z = 637.

Synthesis Example (1-130): Synthesis of Compound (1-3445) Compound (1-3445) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 573.

Synthesis Example (1-113): Synthesis of Compound (1-3467) Compound (1-3467) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 573.

Synthesis Example (1-132): Synthesis of Compound (1-3434) Compound (1-3434) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 573.

Synthesis Example (1-133): Synthesis of Compound (1-3481) Compound (1-3481) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 573.

Synthesis Example (1-134): Synthesis of Compound (1-3408) Compound (1-3408) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 573.

Synthesis Example (1-135): Synthesis of Compound (1-3777) Compound (1-3777) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 589.

Synthesis Example (1-136): Synthesis of Compound (1-3594) Compound (1-3594) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 623.

Synthesis Example (1-137): Synthesis of Compound (1-3589) Compound (1-3589) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 623.

Synthesis Example (1-138): Synthesis of Compound (1-3440) Compound (1-3440) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 673.

Synthesis Example (1-139): Synthesis of Compound (1-3435) Compound (1-3435) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 753.

Synthesis Example (1-140): Synthesis of Compound (1-3572) Compound (1-3572) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 699.

Synthesis Example (1-141): Synthesis of Compound (1-3453) Compound (1-3453) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 825.

Synthesis Example (1-142): Synthesis of Compound (1-3562) Compound (1-3562) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 623.

Synthesis Example (1-143): Synthesis of Compound (1-3559) Compound (1-3559) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 623.

Synthesis Example (1-144): Synthesis of compound (1-3522) Compound (1-3522) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 573.

Synthesis Example (1-145): Synthesis of Compound (1-4014) Compound (1-4014) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 739.

Synthesis Example (1-146): Synthesis of compound (1-4018) Compound (1-4018) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 573.

Synthesis Example (1-147): Synthesis of compound (1-3762) Compound (1-3762) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 623.

Synthesis Example (1-148): Synthesis of compound (1-2912) Compound (1-2912) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 573.

Synthesis Example (1-149): Synthesis of Compound (1-3284) Compound (1-3284) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 573.

Synthesis Example (1-150): Synthesis of Compound (1-3736) Compound (1-3736) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 649.

Synthesis Example (1-151): Synthesis of Compound (1-3770) Compound (1-3770) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 589.

Synthesis Example (1-152): Synthesis of Compound (1-2873) Compound (1-2873) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 648.

Synthesis Example (1-153): Synthesis of Compound (1-3249) Compound (1-3249) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 623.

Synthesis Example (1-154): Synthesis of Compound (1-3296) Compound (1-3296) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 623.

Synthesis Example (1-155): Synthesis of Compound (1-2917) Compound (1-2917) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 803.

Synthesis Example (1-1156): Synthesis of Compound (1-3768) Compound (1-3768) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 723.

Synthesis Example (1-157): Synthesis of compound (1-3780) Compound (1-3780) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 789.

Synthesis Example (1-158): Synthesis of Compound (1-3963) Compound (1-3963) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 573.

Synthesis Example (1-159): Synthesis of Compound (1-4112) Compound (1-4112) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 649.

Synthesis Example (1-160): Synthesis of Compound (1-4052) Compound (1-4052) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 699.

Synthesis Example (1-161): Synthesis of Compound (1-4047) Compound (1-4047) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 649.

Synthesis Example (1-162): Synthesis of Compound (1-3778) Compound (1-3778) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 748.

Synthesis Example (1-163): Synthesis of Compound (1-4008) Compound (1-4008) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 497.

Synthesis Example (1-164): Synthesis of Compound (1-802) Compound (1-802) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 497.

Synthesis Example (1-165): Synthesis of Compound (1-804) Compound (1-804) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 513.

Synthesis Example (1-166): Synthesis of compound (1-3784) Compound (1-3784) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 547.

Synthesis Example (1-167): Synthesis of Compound (1-808) Compound (1-808) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 547.

Synthesis Example (1-168): Synthesis of Compound (1-801) Compound (1-801) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 572.

Synthesis Example (1-169): Synthesis of compound (1-4142) Compound (1-4142) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 713.

Synthesis Example (1-170): Synthesis of Compound (1-4145) Compound (1-4145) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 865.

Synthesis Example (1-171): Synthesis of Compound (1-4138) Compound (1-4138) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 713.

Synthesis Example (1-172): Synthesis of Compound (1-4165) Compound (1-4165) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 713.

Synthesis Example (1-173): Synthesis of Compound (1-4168) Compound (1-4168) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 713.

Synthesis Example (1-174): Synthesis of compound (1-4152) Compound (1-4152) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 713.

Synthesis Example (1-175): Synthesis of compound (1-4143) Compound (1-4143) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 623.

Synthesis Example (1-176): Synthesis of Compound (1-3849) Compound (1-3849) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 863.

Synthesis Example (1-177): Synthesis of compound (1-4434) Compound (1-4434) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 601.

Synthesis Example (1-178): Synthesis of Compound (1-4429) Compound (1-4429) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 601.

Synthesis Example (1-179): Synthesis of Compound (1-4458) Compound (1-4458) is synthesized by appropriately modifying the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 665.

Synthesis Example (1-180): Synthesis of compound (1-4409) Compound (1-4409) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 587.

Synthesis Example (1-181): Synthesis of Compound (1-4404) Compound (1-4404) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 587.

Synthesis Example (1-182): Synthesis of Compound (1-4427) Compound (1-4427) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 615.

Synthesis Example (1-183): Synthesis of Compound (1-2973) Compound (1-2973) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 497.

Synthesis Example (1-184): Synthesis of compound (1-4747) Compound (1-4747) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 573.

Synthesis Example (1-185): Synthesis of Compound (1-3444) Compound (1-3444) is synthesized by appropriately modifying the compound of the raw material of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 673.

Synthesis Example (1-186): Synthesis of compound (1-3450) Compound (1-3450) is synthesized by appropriately changing the raw material compound of the method described in Korean Patent Publication No. 2017-116885. did. EI-MS: m / z = 725.

Synthesis Example (1-187): Synthesis of compound (1-1355) Compound (1-12) (1 g), 5% platinum-carbon (5% Pt / C, 300 mg), heavy water (40 mL), cyclohexane (cHex,) 20 mL) and isopropyl alcohol (IPA, 5 mL) were placed in a flask under an argon atmosphere and heated at 100 ° C. After the reaction, water and chloroform are added for liquid separation extraction, the organic layer is dried over magnesium sulfate and filtered, and then the organic layer is concentrated and the obtained crude product is recrystallized to obtain the desired compound (1-1355). ) Was obtained.
EI-MS: m / z = 532.

Synthesis Example (1-1388): Synthesis of compound (1-1359) A compound represented by the formula (1-1359) was synthesized using the same method as in the above-mentioned synthesis example (1-1387). EI-MS: m / z = 532.

Synthesis Example (1-189): Synthesis of compound (1-1390) The compound represented by the formula (1-1390) was synthesized using the same method as in the above-mentioned synthesis example (1-187). EI-MS: m / z = 668.

Synthesis Example (1-196): Synthesis of compound (1-1996) The compound represented by the formula (1-1996) was synthesized using the same method as in the above-mentioned synthesis example (1-187). EI-MS: m / z = 749.

Synthesis Example (1-191): Synthesis of compound (1-1598) Using the same method as in the above-mentioned synthesis example (1-187), the compound represented by the formula (1-1598) was synthesized. EI-MS: m / z = 584.

Synthesis Example (1-1192): Synthesis of compound (1-1658) The compound represented by the formula (1-1658) was synthesized using the same method as in the synthesis example (1-1187) described above. EI-MS: m / z = 584.

Synthesis Example (1-193): Synthesis of compound (1-1789) The compound represented by the formula (1-1789) was synthesized using the same method as in the synthesis example (1-187) described above. EI-MS: m / z = 520.

Synthesis Example (1-1794): Synthesis of compound (1-1791) The compound represented by the formula (1-1791) was synthesized using the same method as in the synthesis example (1-1187) described above. EI-MS: m / z = 624.

Synthesis Example (1-195): Synthesis of compound (1-1825) Using the same method as in the above-mentioned synthesis example (1-187), the compound represented by the formula (1-1825) was synthesized. EI-MS: m / z = 572.

Synthesis Example (1-196): Synthesis of compound (1-1468) The compound represented by the formula (1-1468) was synthesized using the same method as in the above-mentioned synthesis example (1-1487). EI-MS: m / z = 668.

Synthesis Example (1-197): Synthesis of compound (1-1998) A compound represented by the formula (1-1998) was synthesized using the same method as in the above-mentioned synthesis example (1-1987). EI-MS: m / z = 908.

Synthesis Example (1-198): Synthesis of compound (1-2389) The compound represented by the formula (1-2389) was synthesized using the same method as in the above-mentioned synthesis example (1-1187). EI-MS: m / z = 664.

Synthesis Example (1-199): Synthesis of compound (1-1618) The compound represented by the formula (1-1618) was synthesized using the same method as in the above-mentioned synthesis example (1-1187). EI-MS: m / z = 768.

Synthesis Example (1-200): Synthesis of Compound (1-1372) Using the same method as in Synthesis Example (1-187) described above, the compound represented by the formula (1-1372) was synthesized. EI-MS: m / z = 612.

Synthesis Example (1-201): Synthesis of Compound (1-1615) A compound represented by the formula (1-1615) was synthesized using the same method as in the above-mentioned Synthesis Example (1-187). EI-MS: m / z = 664.

Synthesis Example (1-202): Synthesis of Compound (1-1783) A compound represented by the formula (1-1783) was synthesized using the same method as in the above-mentioned Synthesis Example (1-187). EI-MS: m / z = 704.

Synthesis Example (1-203): Synthesis of compound (1-1356) A compound represented by the formula (1-1356) was synthesized using the same method as in the above-mentioned synthesis example (1-1187). EI-MS: m / z = 692.

Synthesis Example (1-204): Synthesis of Compound (1-1626) A compound represented by the formula (1-1626) was synthesized using the same method as in the above-mentioned Synthesis Example (1-187). EI-MS: m / z = 560.

Synthesis Example (1-205): Synthesis of compound (1-1467) The compound represented by the formula (1-1467) was synthesized using the same method as in the above-mentioned synthesis example (1-1487). EI-MS: m / z = 508.

Synthesis Example (1-206): Synthesis of Compound (1-1347) A compound represented by the formula (1-1347) was synthesized using the same method as in the above-mentioned Synthesis Example (1-1187). EI-MS: m / z = 588.

Synthesis Example (1-207): Synthesis of compound (1-1860) The compound represented by the formula (1-1860) was synthesized using the same method as in the above-mentioned synthesis example (1-187). EI-MS: m / z = 572.

Synthesis Example (1-208): Synthesis of Compound (1-1855) A compound represented by the formula (1-1855) was synthesized using the same method as in Synthesis Example (1-187) described above. EI-MS: m / z = 520.

Synthesis Example (1-209): Synthesis of Compound (1-2397) Using the same method as in Synthesis Example (1-187) described above, the compound represented by the formula (1-2397) was synthesized. EI-MS: m / z = 560.

Synthesis Example (1-210): Synthesis of Compound (1-2398) A compound represented by the formula (1-2398) was synthesized using the same method as in the above-mentioned Synthesis Example (1-187). EI-MS: m / z = 508.

Synthesis Example (1-211): Synthesis of Compound (1-4655) Compound (1-4655) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 526.

Synthesis Example (1-212): Synthesis of Compound (1-4660) Compound (1-4660) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 592.

Synthesis Example (1-213): Synthesis of Compound (1-2388) The compound represented by the formula (1-2388) was synthesized by using the same method as in the above-mentioned Synthesis Example (1-187). EI-MS: m / z = 613.

Synthesis Example (1-214): Synthesis of Compound (1-4573) The compound represented by the formula (1-4573) was synthesized by using the same method as in the above-mentioned Synthesis Example (1-187). EI-MS: m / z = 601.

Synthesis Example (1-215): Synthesis of Compound (1-4579) Compound (1-4579) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 588.

Synthesis Example (1-216): Synthesis of Compound (1-4510) Using the same method as in Synthesis Example (1-187) described above, the compound represented by the formula (1-4510) was synthesized. EI-MS: m / z = 601.

Synthesis Example (1-217): Synthesis of Compound (1-4701) Using the same method as in Synthesis Example (1-187) described above, the compound represented by the formula (1-4701) was synthesized. EI-MS: m / z = 640.

Synthesis Example (1-218): Synthesis of Compound (1-4688) Compound (1-4688) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 631.

Synthesis Example (1-219): Synthesis of Compound (1-4715) Compound (1-4715) is synthesized by appropriately changing the raw material compound of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 624.

Synthesis Example (1-220): Synthesis of Compound (1-4565) A compound represented by the formula (1-4565) was synthesized by using the same method as in the above-mentioned Synthesis Example (1-187). EI-MS: m / z = 680.

Synthesis Example (1-221): Synthesis of Compound (1-4736) Compound (1-4736) is synthesized by appropriately changing the compound of the raw material of the method described in the above-mentioned Synthesis Example (1-56). did. EI-MS: m / z = 498.

化合物（２−４１）は、国際公開第２０１５／１０２１１８号の「合成例（３２）」に記載された方法に準じて合成した。 Synthesis example (2-1): Synthesis of compound (2-41)

Compound (2-41) was synthesized according to the method described in "Synthesis Example (32)" of International Publication No. 2015/102118.

The structure of the compound obtained by NMR measurement was confirmed.
^{1 1} H-NMR (500 MHz, CDCl ₃ ): δ = 1.47 (s, 36H), 2.17 (s, 3H), 5.97 (s, 2H), 6.68 (d, 2H), 7 .28 (d, 4H), 7.49 (dd, 2H), 7.67 (d, 4H), 8.97 (d, 2H).

Synthesis example (2-2): Synthesis of compound (2-31)

Compound (2-31) was synthesized according to the method described in "Synthesis Example (32)" of International Publication No. 2015/102118.

The structure of the compound obtained by NMR measurement was confirmed.
^{1 1} H-NMR (500 MHz, CDCl ₃ ): δ = 1.46 (s, 18H), 1.47 (s, 18H), 6.14 (d, 2H), 6.75 (d, 2H), 7 .24 (t, 1H), 7.29 (d, 4H), 7.52 (dd, 2H), 7.67 (d, 4H), 8.99 (d, 2H).

Synthesis example (2-3): Synthesis of compound (2-46)

Compound (2-46) was synthesized according to the method described in "Synthesis Example (32)" of International Publication No. 2015/102118.

The structure of the compound obtained by NMR measurement was confirmed.
^{1 1} H-NMR (CDCl ₃ ): δ = 1.20 (s, 9H), 1.37 (s, 18H), 1.46 (s, 9H), 1.47 (s, 9H), 2.18 (S, 3H), 5.97 (s, 1H), 6.08 (d, 1H), 6.63 (d, 1H), 6.66 (d, 1H), 7.20 (d, 2H) , 7.27 (d, 2H), 7.32 (dd, 1H), 7.48 (dd, 1H), 7.61 (t, 1H), 7.67 (d, 2H), 8.84 ( d, 1H), 8.94 (d, 1H).

Synthesis example (2-4): Synthesis of compound (2-37)

Compound (2-37) was synthesized according to the method described in "Synthesis Example (32)" of International Publication No. 2015/102118.

The structure of the compound obtained by NMR measurement was confirmed.
^{1 1} H-NMR (CDCl ₃ ): δ = 1.20 (s, 9H), 1.36 (s, 18H), 1.46 (s, 9H), 1.47 (s, 9H), 6.14 (D, 1H), 6.25 (d, 1H), 6.68 (d, 1H), 6.73 (d, 1H), 7.21 (d, 2H), 7.29 (d, 3H) , 7.34 (dd, 1H), 7.51 (dd, 1H), 7.61 (t, 1H), 7.67 (d, 2H), 8.86 (d, 1H), 8.96 ( d, 1H).

Synthesis example (2-5): Synthesis of compound (2-42)

Using the same method as in Synthesis Example (2-1), the compound represented by the formula (2-42) was synthesized.

The structure of the compound obtained by NMR measurement was confirmed.
^{1 1} H-NMR (CDCl ₃ ): δ = 1.37 (s, 18H), 1.46 (s, 9H), 1.47 (s, 9H), 2.17 (s, 3H), 5.56 (S, 1H), 5.99 (s, 1H), 6.68 (d, 1H), 6.74 (d, 1H), 7.19 (d, 2H), 7.24-7.29 ( m, 3H), 7.42 (t, 1H), 7.49 (dd, 1H), 7.61 (t, 1H), 7.68 (d, 2H), 8.91 (dd, 1H), 8.92 (d, 1H).

Synthesis example (2-6): Synthesis of compound (2-49)

Compound (2-49) was synthesized according to the method described in "Comparative Synthesis Example (1)" of JP-A-2016-88927.

The structure of the compound obtained by NMR measurement was confirmed.
^{1 1} H-NMR (CDCl ₃ ): δ = 1.33 (s, 18H), 1.46 (s, 18H), 5.55 (s, 2H), 6.75 (d, 2H), 6.89 (T, 2H), 6.94 (d, 4H), 7.06 (t, 4H), 7.13 (d, 4H), 7.43 to 7.46 (m, 6H), 8.95 ( d, 2H).

Synthesis example (2-7): Synthesis of compound (2-50)

Compound (2-50) was synthesized according to the method described in "Synthesis Example (32)" of International Publication No. 2015/102118.

The structure of the compound obtained by NMR measurement was confirmed.
^{1 1} H-NMR (CDCl ₃ ): δ = 1.3 (s, 18H), 1.3 (s, 18H), 1.5 (s, 18H), 5.8 (s, 2H), 6.6 (D, 2H), 6.8 (dd, 4H), 7.1 (dd, 4H), 7.1 (dd, 4H), 7.4 to 7.5 (m, 6H), 8.9 ( d, 2H).

Synthesis example (2-8): Synthesis of compound (2-53)

Compound (2-53) was synthesized according to the method described in "Synthesis Example (32)" of International Publication No. 2015/102118.

The structure of the compound obtained by NMR measurement was confirmed.
^{1 1} H-NMR (CDCl ₃ ): δ = 1.35 (s, 18H), 1.50 (s, 18H), 6.34 (s, 2H), 6.85 (d, 2H), 7.16 (T, 2H), 7.23 (t, 2H), 7.32 to 7.35 (m, 6H), 7.56 (dd, 2H), 7.63 (d, 4H), 7.99 ( d, 2H), 9.05 (d, 2H).

Synthesis example (2-9): Synthesis of compound (2-33)

Compound (2-33) was synthesized according to the method described in "Synthesis Example (32)" of International Publication No. 2015/102118.

The structure of the compound obtained by NMR measurement was confirmed.
^{1 1} H-NMR (CDCl ₃ ): δ = 1.22 (s, 9H), 1.37 (s, 9H), 1.46 (s, 9H), 1.47 (s, 9H), 6.14 (D, 1H), 6.18 (d, 1H), 6.72 (d, 1H), 6.74 (d, 1H), 7.19 (ddd, 1H), 7.23-7.30 ( m, 3H), 7.34 (dd, 1H), 7.41 (t, 1H), 7.51 (dd, 1H), 7.58 to 7.64 (m, 2H), 7.67 (d) , 2H), 8.86 (d, 1H), 8.96 (d, 1H).

Synthesis example (2-10): Synthesis of compound (2-508)

4- (T-Amil) aniline (15.0 g) was dissolved in acetonitrile (150 ml) under a nitrogen atmosphere, bromine (22.5 g) was added dropwise thereto under ice-cooling, and the mixture was stirred for 0.5 hours. After the reaction, water and ethyl acetate were added to the reaction solution, and the mixture was stirred, and then the organic layer was separated and washed with water. Then, the organic layer was concentrated to obtain a crude product. The crude product was purified on a silica gel short column (eluent: toluene) to give the intermediate (IA) (20.0 g).

Under a nitrogen atmosphere, copper (10.1 g) chloride and intermediate (IA) (20.0 g) were dissolved in acetonitrile (100 ml), and t-butyl nitrite (50 ml) was dissolved therein. 9.6 g) was added dropwise at 60 ° C., and the mixture was stirred at the same temperature for 0.5 hours. After the reaction, dilute hydrochloric acid and ethyl acetate were added to the reaction solution, and the mixture was stirred, and then the organic layer was separated and washed with water. Then, the organic layer was concentrated to obtain a crude product. The crude product was purified by silica gel short column (eluent: toluene / heptane = 1/4 (volume ratio)) to obtain an intermediate (IB) (19.0 g).

Under a nitrogen atmosphere, intermediate (IB) (10.0 g), bis (4-t-butylphenyl) amine (18.2 g), dichlorobis (di-t-butyl (4-dimethylaminophenyl)) as a palladium catalyst Palladium (phosphino) palladium (Pd-132, 0.21 g), sodium-t-butoxide (NaOtBu, 7.1 g) and xylene (100 ml) were placed in a flask and heated at 100 ° C. for 1 hour. After the reaction, water and toluene were added to the reaction solution, and the mixture was stirred, and then the organic layer was separated and washed with water. Then, the organic layer was concentrated to obtain a crude product. The crude product was purified on a silica gel short column (eluent: toluene) to give an intermediate (IC) (18.0 g).

In a flask containing the intermediate (IC) (18.0 g) and t-butylbenzene (500 ml), add a 1.56 M t-butyllithium pentane solution (28.9 ml) at 0 ° C. under a nitrogen atmosphere. added. After completion of the dropping, the temperature was raised to 70 ° C. and the mixture was stirred for 0.5 hours, and then components having a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to −50 ° C., boron tribromide (11.3 g) was added, the temperature was raised to room temperature, and the mixture was stirred for 0.5 hours. Then, the mixture was cooled to 0 ° C. again, N, N-diisopropylethylamine (5.8 g) was added, and the mixture was stirred at room temperature until the exotherm subsided, then the temperature was raised to 100 ° C. and the mixture was heated and stirred for 1 hour. The reaction mixture was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath and then ethyl acetate were added to separate the solutions. After concentrating the organic layer, it was purified by a silica gel short column (eluent: toluene). The obtained crude product was recrystallized from chlorobenzene to obtain compound (2-508) (7.1 g).

The structure of the compound obtained by NMR measurement was confirmed.
^{1 1} H-NMR (CDCl ₃ ): δ = 0.49 (t, 3H), 0.92 (s, 6H), 1.28 (q, 2H), 1.46 (s, 18H), 1.47 (S, 18H), 6.05 (s, 2H), 6.77 (d, 2H), 7.28 (m, 4H), 7.50 (m, 2H), 7.67 (m, 4H) , 8.97 (d, 2H).

Synthesis example (2-11): Synthesis of compound (2-538)

Under a nitrogen atmosphere, 3,4,5-trichloro-aniline (12.0 g), ^{d 5} - bromobenzene (30.0 g), dichlorobis as palladium catalyst (di -t- butyl (4-dimethylaminophenyl) phosphino) palladium ( Pd-132, 0.43 g), sodium-t-butoxide (NaOtBu, 14.7 g) and xylene (200 mL) were placed in a flask and heated at 120 ° C. for 3 hours. After the reaction, water and ethyl acetate were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. Then, the organic layer was concentrated to obtain a crude product. The crude product was purified by silica gel short column (eluent: toluene / heptane = 1/1 (volume ratio)) to obtain 15.0 g of an intermediate (ID).

Under a nitrogen atmosphere, intermediate (ID) (15.0 g), bis (4-t-butylphenyl) amine (25.9 g), bis (dibenzylideneacetone) palladium (0.48 g), 2-dicyclohexylphos Fino-2', 6'-dimethoxybiphenyl (SPhos, 0.86 g), sodium-t-butoxide (10.0 g) and xylene (130 mL) were placed in a flask and heated at 100 ° C. for 1 hour. After the reaction, water and toluene were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. Then, the organic layer was concentrated to obtain a crude product. The crude product was purified by silica gel short column (eluent: toluene) to obtain 23.0 g of intermediate (IE).

In a flask containing Intermediate (IE) (23.0 g) and tert-butylbenzene (250 ml), add 1.62 M tert-butyllithium pentane solution (33.5 ml) at 0 ° C. under a nitrogen atmosphere. added. After completion of the dropping, the temperature was raised to 60 ° C. and the mixture was stirred for 1 hour, and then components having a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to −50 ° C., boron tribromide (13.6 g) was added, the temperature was raised to room temperature, and the mixture was stirred for 0.5 hours. Then, the mixture was cooled to 0 ° C. again, N, N-diisopropylethylamine (7.0 g) was added, and the mixture was stirred at room temperature until the exotherm subsided, then the temperature was raised to 100 ° C. and the mixture was heated and stirred for 1 hour. The reaction mixture was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath and then ethyl acetate were added to separate the solutions. The organic layer was concentrated and then purified on a silica gel short column (eluent: heated chlorobenzene). The obtained crude product was washed with refluxed heptane and refluxed ethyl acetate, and then reprecipitated from chlorobenzene to obtain compound (2-538) (12.9 g).

The structure of the compound obtained by NMR measurement was confirmed.
^{1 1} H-NMR (CDCl ₃ ): δ = 1.3 (s, 18H), 1.5 (s, 18H), 5.6 (s, 2H), 6.8 (d, 2H), 7.1 (M, 4H), 7.4 to 7.5 (m, 6H), 9.0 (d, 2H).

Synthesis example (2-12): Synthesis of compound (2-541)

Under a nitrogen atmosphere, ^{d 5} - aniline (5.0g), ^{d 5} - bromobenzene (8.25g), Pd-132 ( 0.36g) as a palladium catalyst, flask NaOtBu (7.1 g) and xylene (100 mL) And heated at 120 ° C. for 1.5 hours. After the reaction, water and ethyl acetate were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. Then, the organic layer was concentrated to obtain a crude product. The crude product was purified by silica gel short column (eluent: toluene / heptane = 1/1 (volume ratio)) to obtain 8.1 g of an intermediate (IF).

Intermediate (IF) (8.0 g), Intermediate (IG) (20.6 g), Pd-132 (0.31 g) as palladium catalyst, NaOtBu (6.4 g) and xylene under nitrogen atmosphere (100 mL) was placed in a flask and heated at 120 ° C. for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. Then, the organic layer was concentrated to obtain a crude product. The crude product was purified by a silica gel short column (eluent: toluene / heptane = 1/1 (volume ratio)) to obtain 20.2 g of an intermediate (IH).

In a flask containing Intermediate (IH) (10.0 g) and tert-butylbenzene (150 ml), add 1.62 M tert-butyllithium pentane solution (21.2 ml) at 0 ° C. under a nitrogen atmosphere. added. After completion of the dropping, the temperature was raised to 60 ° C. and the mixture was stirred for 0.5 hours, and then components having a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to −50 ° C., boron tribromide (8.6 g) was added, the temperature was raised to room temperature, and the mixture was stirred for 0.5 hours. Then, the mixture was cooled to 0 ° C. again, N, N-diisopropylethylamine (4.4 g) was added, and the mixture was stirred at room temperature until the exotherm subsided, then the temperature was raised to 100 ° C. and the mixture was heated and stirred for 1 hour. The reaction mixture was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath and then ethyl acetate were added to separate the solutions. After concentrating the organic layer, it was purified by a silica gel short column (eluent: toluene). After dissolving the obtained crude product in toluene, heptane was added, the precipitated crystals were filtered, and the filtered crystals were washed with chilled heptane to obtain compound (2-541) (3. 1g).

The structure of the compound obtained by NMR measurement was confirmed.
^{1 1} H-NMR (CDCl ₃ ): δ = 1.46 (s, 9H), 1.47 (s, 9H), 2.16 (s, 3H), 5.92 (s, 1H), 6.00 (S, 1H), 6.69 (d, 1H), 7.25-7.28 (m, 2H), 7.49-7.51 (m, 1H), 7.66-7.69 (m) , 2H), 8.92 (d, 1H).

Synthesis example (2-13): Synthesis of compound (2-544)

Under a nitrogen atmosphere, intermediate (I) (8.4 g), intermediate (IJ) (4.6 g), bis (dibenzylideneacetone) palladium (0.23 g), 2-dicyclohexylphosphino-2 ', 6'-Dimethoxybiphenyl (SPhos, 0.32 g), sodium-t-butoxide (3.2 g) and xylene (40 ml) were placed in a flask and heated at 100 ° C. for 1.5 hours. After the reaction, water and toluene were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. Then, the organic layer was concentrated to obtain a crude product. The crude product was purified on a silica gel short pass column (eluent: toluene) to give the intermediate (IK) (8.6 g).

In a flask containing Intermediate (IK) (8.6 g) and tert-butylbenzene (90 ml), add 1.62 M tert-butyllithium pentane solution (12.9 ml) at 0 ° C. under a nitrogen atmosphere. added. After completion of the dropping, the temperature was raised to 70 ° C. and the mixture was stirred for 0.5 hours, and then components having a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to −50 ° C., boron tribromide (5.0 g) was added, the temperature was raised to room temperature, and the mixture was stirred for 0.5 hours. Then, the mixture was cooled to 0 ° C. again, N, N-diisopropylethylamine (2.6 g) was added, and the mixture was stirred at room temperature until the exotherm subsided, then the temperature was raised to 100 ° C. and the mixture was heated and stirred for 1 hour. The reaction mixture was cooled to room temperature, an aqueous sodium acetate solution cooled in an ice bath, then ethyl acetate was added, and the mixture was stirred for 1 hour. The yellow suspension was filtered, and the precipitate was washed twice with methanol and pure water, and then washed again with methanol. The yellow crystals were dissolved by heating in chlorobenzene and then purified by a silica gel short pass column (eluent: heated chlorobenzene). The obtained crude product was filtered by adding heptane, and then the crystals were washed with heptane to obtain compound (2-544) (6.5 g).

The structure of the compound obtained by NMR measurement was confirmed.
^{1 1} H-NMR (CDCl ₃ ): δ = 1.33 (s, 18H), 1.46 (s, 18H), 5.55 (s, 2H), 6.88 (t, 2H), 6.94 (D, 4H), 7.06 (dd, 4H).

Synthesis example (2-14): Synthesis of compound (2-542)

Intermediate (I-I) (10.7 g), Intermediate (ID) (6.0 g), Bis (dibenzylideneacetone) Palladium (0.58 g), 2-Dicyclohexylphosphino-2 under nitrogen atmosphere ', 6'-Dimethoxybiphenyl (SPhos, 0.82 g), sodium-t-butoxide (4.0 g) and xylene (60 ml) were placed in a flask and heated at 100 ° C. for 1.5 hours. After the reaction, water and toluene were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. Then, the organic layer was concentrated to obtain a crude product. The crude product was purified on a silica gel short pass column (eluent: toluene), and the obtained solid was washed with cooled heptane to obtain an intermediate (IL) (9.4 g).

In a flask containing Intermediate (IL) (8.6 g) and tert-butylbenzene (100 ml), add 1.62 M tert-butyllithium pentane solution (13.8 ml) at 0 ° C. under a nitrogen atmosphere. added. After completion of the dropping, the temperature was raised to 60 ° C. and the mixture was stirred for 0.5 hours, and then components having a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to −50 ° C., boron tribromide (5.4 g) was added, the temperature was raised to room temperature, and the mixture was stirred for 0.5 hours. Then, the mixture was cooled to 0 ° C. again, N, N-diisopropylethylamine (2.8 g) was added, and the mixture was stirred at room temperature until the exotherm subsided, then the temperature was raised to 100 ° C. and the mixture was heated and stirred for 1 hour. The reaction mixture was cooled to room temperature, an aqueous sodium acetate solution cooled in an ice bath, then ethyl acetate was added, and the mixture was stirred for 1 hour. The yellow suspension was filtered, and the precipitate was washed twice with methanol and pure water, and then washed again with methanol. The yellow crystals were dissolved by heating in chlorobenzene and then purified by a silica gel short pass column (eluent: heated chlorobenzene). The crude product obtained was filtered by adding heptane, and then the crystals were washed with heptane to obtain compound (2-542) (5.9 g).

The structure of the compound obtained by NMR measurement was confirmed.
^{1 1} H-NMR (CDCl ₃ ): δ = 1.32 (s, 18H), 1.46 (s, 18H), 5.55 (s, 2H).

Synthesis example (2-15): Synthesis of compound (2-290)

Compound (2-290) was synthesized according to the method described in "Synthesis Example (1)" of International Publication No. 2017/126443.

The structure of the compound (2-290) obtained by NMR measurement was confirmed.
^{1 1} H-NMR (CDCl ₃ ): δ = 8.64 (s, 2H), 7.75 (m, 3H), 7.69 (d, 2H), 7.30 (t, 8H), 7.25 (S, 2H), 7.20 (m, 10H), 7.08 (m, 6H), 1.58 (s, 12H).

Synthesis example (2-16): Synthesis of compound (2-351)

Compound (2-351) was synthesized according to the method described in "Synthesis Example (5)" of International Publication No. 2017/126443.

The structure of the compound of the formula (2-351) was confirmed by NMR measurement.

^{1 1} H-NMR (CDCl ₃ ): δ = 9.22 (s, 1H), 8.78 (s, 1H), 7.96 (d, 2H), 7.80 to 7.77 (m, 6H) , 7.71 (d, 1H), 7.59 to 7.44 (m, 8H), 7.39 (t, 1H), 7.32 to 7.29 (m, 4H), 7.71 (d) , 1H), 7.19 (dd, 4H), 7.12 to 7.06 (m, 4H), 7.00 (d, 1H), 6.45 (d, 1H), 1.57 (s, 6H).

The glass transition temperature (Tg) of the compound of the formula (2-351) was 165.6 ° C.
[Measuring equipment: Diamond DSC (manufactured by PERKIN-ELMER); Measuring conditions: Cooling rate 200 ° C./Min. , Temperature rise rate 10 ° C./Min. ]

合成例（２−１）と同様の方法を用い、化合物（２−６０）を合成した。
ＮＭＲ測定により得られた化合物の構造を確認した。
^１Ｈ−ＮＭＲ：δ＝１．１（ｓ，９Ｈ）、１．４（ｓ，９Ｈ）、１．５（ｓ，９Ｈ）、１．５（ｓ，９Ｈ）、１．５（ｓ，９Ｈ）、２．２（ｓ，３Ｈ）、５．９（ｓ，１Ｈ）、６．１（ｓ，１Ｈ）、６．７（ｍ，２Ｈ）、７．０（ｄ，２Ｈ）、７．１（ｄ，２Ｈ）、７．２（ｄ，１Ｈ）、７．３（ｍ，２Ｈ）、７．４（ｍ，１Ｈ）、７．５（ｍ，１Ｈ）、７．６（ｄｄ，１Ｈ）、７．７（ｍ，３Ｈ）、８．９（ｄ，１Ｈ）、８．９（ｄ，１Ｈ）． Synthesis example (2-17): Synthesis of compound (2-60)

Compound (2-60) was synthesized using the same method as in Synthesis Example (2-1).
The structure of the compound obtained by NMR measurement was confirmed.
^{1 1} H-NMR: δ = 1.1 (s, 9H), 1.4 (s, 9H), 1.5 (s, 9H), 1.5 (s, 9H), 1.5 (s, 9H) ), 2.2 (s, 3H), 5.9 (s, 1H), 6.1 (s, 1H), 6.7 (m, 2H), 7.0 (d, 2H), 7.1 (D, 2H), 7.2 (d, 1H), 7.3 (m, 2H), 7.4 (m, 1H), 7.5 (m, 1H), 7.6 (dd, 1H) , 7.7 (m, 3H), 8.9 (d, 1H), 8.9 (d, 1H).

合成例（２−１）と同様の方法を用い、化合物（２−５６１）を合成した。
ＮＭＲ測定により得られた化合物の構造を確認した。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３）：δ＝１．０８（ｓ，６Ｈ）、１．２７（ｓ，６Ｈ）、１．４２（ｓ，６Ｈ）、１．４６（ｓ，９Ｈ）、１．４７（ｓ，９Ｈ）、１．４８（ｓ，６Ｈ）、１．６９−１．８１（ｍ，８Ｈ）、２．１８（ｓ，３Ｈ）、５．９７（ｓ，１Ｈ）、６．０６（ｓ，１Ｈ）、６．５２（ｓ，１Ｈ）、６．６７（ｄ，１Ｈ）、７．０８（ｄｄ，１Ｈ）、７．２５−７．２９（ｍ，３Ｈ）、７．４８（ｄｄ，１Ｈ）、７．５９（ｄ，１Ｈ）、７．６７（ｄ，２Ｈ）、８．８９（ｓ，１Ｈ）、８．９７（ｄ，１Ｈ）． Synthesis example (2-18): Synthesis of compound (2-561)

Compound (2-561) was synthesized using the same method as in Synthesis Example (2-1).
The structure of the compound obtained by NMR measurement was confirmed.
^{1 1} H-NMR (CDCl ₃ ): δ = 1.08 (s, 6H), 1.27 (s, 6H), 1.42 (s, 6H), 1.46 (s, 9H), 1.47 (S, 9H), 1.48 (s, 6H), 1.69-1.81 (m, 8H), 2.18 (s, 3H), 5.97 (s, 1H), 6.06 ( s, 1H), 6.52 (s, 1H), 6.67 (d, 1H), 7.08 (dd, 1H), 7.25-7.29 (m, 3H), 7.48 (dd) , 1H), 7.59 (d, 1H), 7.67 (d, 2H), 8.89 (s, 1H), 8.97 (d, 1H).

合成例（２−１）と同様の方法を用い、化合物（２−５７４）を合成した。マススペクトル分析により、得られた化合物が化合物（２−５７４）であることを確認した。
ＥＩ−ＭＳ：ｍ/ｚ＝７５６． Synthesis Example (2-19): Synthesis of compound (2-574)

Compound (2-574) was synthesized using the same method as in Synthesis Example (2-1). Mass spectrum analysis confirmed that the obtained compound was compound (2-574).
EI-MS: m / z = 756.

合成例（２−１）と同様の方法を用い、化合物（２−５７８）を合成した。マススペクトル分析により、得られた化合物が化合物（２−５７８）であることを確認した。
ＥＩ−ＭＳ：ｍ/ｚ＝８８９． Synthesis example (2-20): Synthesis of compound (2-578)

Compound (2-578) was synthesized using the same method as in Synthesis Example (2-1). Mass spectrum analysis confirmed that the obtained compound was compound (2-578).
EI-MS: m / z = 889.

合成例（２−１）と同様の方法を用い、化合物（２−５８０）を合成した。マススペクトル分析により、得られた化合物が化合物（２−５８０）であることを確認した。
ＥＩ−ＭＳ：ｍ/ｚ＝８１１． Synthesis example (2-21): Synthesis of compound (2-580)

Compound (2-580) was synthesized using the same method as in Synthesis Example (2-1). Mass spectrum analysis confirmed that the obtained compound was compound (2-580).
EI-MS: m / z = 811.

合成例（２−１）と同様の方法を用い、化合物（２−５８９）を合成した。マススペクトル分析により、得られた化合物が化合物（２−５８９）であることを確認した。
ＥＩ−ＭＳ：ｍ/ｚ＝９４４． Synthesis example (2-22): Synthesis of compound (2-589)

Compound (2-589) was synthesized using the same method as in Synthesis Example (2-1). Mass spectrum analysis confirmed that the obtained compound was compound (2-589).
EI-MS: m / z = 944.

Synthesis example (2-23): Synthesis of compound (2-591)

Tri-p-tolylamine (0.287 g, 1.00 mmol), boron triiodide (0.783 g, 2.00 mmol) and o-dichlorobenzene (10.0 ml) are heated and stirred at 150 ° C. for 2 hours under a nitrogen atmosphere. did. The reaction was cooled to room temperature and 2-isopropenylphenylmagnesium bromide (5.25 ml, 1.2 M, 6.30 mmol) was added. Then, the mixture was filtered using a Florisil short pass column (eluent: toluene), and the solvent was distilled off under reduced pressure. The obtained crude product was isolated and purified by washing with hexane to obtain 2,8-dimethyl-10- (2- (pro-1-pen-2-yl) phenyl) -5- (p-tolyl). ) -5,10-Dihydrodibenzo [b, e] [1,4] azaborine was obtained in 0.309 g with a yield of 75%.

The structure of the compound obtained by NMR measurement was confirmed.
^{1 1} H-NMR (CDCl ₃ ): δ = 2.05 (s, 3H), 2.31 (s, 6H), 2.54 (s, 3H), 4.78 (s, 2H), 6.74. (D, 2H) 7.20-7.28 (m, 4H), 7.37-7.48 (m, 5H), 7.56 (d, 1H), 7.68 (s, 2H).
¹³ C-NMR (CDCl ₃ ): δ = 20.6 (s, 2C), 21.3 (s, 1C), 23.8 (s, 1C), 116.7 (s, 2C), 116.9 (S, 1C), 126.0 (d, 2C), 126.8 (s, 1C), 128.2 (s, 2C), 130.0 (d, 4C), 131.4 (d, 4C) , 133.0 (s, 1C), 133.7 (s, 2C), 136.4 (s, 2C), 138.6 (s, 1C), 139.3 (s, 1C), 145.1 ( s, 1C), 147.0 (d, 2C).

2,8-Dimethyl-10- (2- (pro-1-pen-2-yl) phenyl) -5- (p-tolyl) -5,10-dihydrodibenzo [b, e] [1,4] azaborin (82.2 mg, 0.20 mmol), scandium trifluoromethanesulfonate (0.100 g, 0.20 mmol) and 1,2-dichloroethane (55.0 ml) were heated and stirred at 95 ° C. for 24 hours under a nitrogen atmosphere. After cooling the reaction solution to room temperature, the mixture was filtered using a Florisil short pass column (eluent: toluene), and the solvent was distilled off under reduced pressure. The obtained crude product was isolated and purified by a silica gel column (eluent: hexane / toluene = 6/1 (volume ratio)) to obtain 32.0 mg of compound (2-591) in a yield of 39%. ..

The structure of the compound obtained by NMR measurement was confirmed.
^{1 1} H-NMR (CDCl ₃ ): δ = 1.98 (s, 6H), 2.48 (s, 3H), 2.53 (s, 3H), 2.76 (s, 3H), 6.61 (D, 1H), 6.75 (d, 1H), 7.14-7.31 (m, 4H), 7.40-7.47 (m, 3H), 7.57 (dt, 1H), 7.81 (d, 1H), 8.44 (d, 1H), 8.50 (s, 1H).
¹³ C-NMR (CDCl ₃ ): δ = 20.9 (s, 1C), 21.4 (s, 1C), 24.3 (s, 1C), 32.6 (s, 2C), 43.5 (S, 1C), 114.0 (s, 1C), 116.6 (s, 1C), 124.7 (s, 1C), 125.8 (s, 1C), 127.0 (s, 1C) , 128.4 (s, 2C), 130.1 (s, 2C), 130.5 (s, 1C), 131.4 (s, 2C), 133.0 (s, 1C), 135.2 ( s, 1C), 135.5 (s, 1C), 137.7 (s, 1C), 138.4 (s, 1C), 139.5 (s, 1C), 144.3 (s, 1C), 145.4 (s, 1C), 151.4 (s, 1C), 159.5 (s, 1C).

Synthesis example (2-24): Synthesis of compound (2-32)

Using the same method as in Synthesis Example (2-1), the compound represented by the formula (2-32) was synthesized. Mass spectrum analysis confirmed that the obtained compound was compound (2-32).
EI-MS: m / z = 645.

化合物（Ｈ−１）は、国際公開第２０１５／０６４５６０号に記載された方法の原料を便宜変更して合成した。 Comparative synthesis example (1)
Synthesis of compound (H-1)

Compound (H-1) was synthesized by conveniently modifying the raw materials of the method described in WO 2015/064560.

化合物（Ｈ−２）は、特開２００６−０４５５０３号公報に記載された方法に準じて合成した。 Comparative synthesis example (*)
Synthesis of compound (H-2)

Compound (H-2) was synthesized according to the method described in JP-A-2006-045503.

化合物（Ｈ−３）は、国際公開第２０１８／１５０８３２号に記載された方法に準じて合成した。 Comparative synthesis example (*)
Synthesis of compound (H-3)

Compound (H-3) was synthesized according to the method described in WO 2018/150832.

化合物（Ｄ−１）は、国際公開第２０１２／１１８１６４号の化合物１の合成法に準じて合成した。 Comparative synthesis example (2)
Synthesis of compound (D-1)

Compound (D-1) was synthesized according to the method for synthesizing compound 1 of International Publication No. 2012/118164.

By appropriately changing the compound of the raw material, another compound of the present invention can be synthesized by a method according to the above-mentioned synthesis example.

Hereinafter, in order to explain the present invention in more detail, examples of an organic EL device using the compound of the present invention will be shown, but the present invention is not limited thereto.

The organic EL devices according to Examples 1 to 165, Reference Examples 1 to 10 and Comparative Examples 1 to 10 were produced, and the emission wavelength (nm), voltage (V), and external quantum, which are the characteristics at the time of ^{1000 cd / m 2 emission, respectively.} Efficiency (%) was measured. Examples 18-60, Examples 79-134, Examples 142-165, Reference Examples 2-3, Reference Examples 5-7, Reference Examples 9-10, Comparative Examples 2-3, Comparative Examples 5-7, and Comparison For the organic EL devices according to Examples 9 to 10, the time for maintaining the brightness of 90% or more of the initial brightness when driven at a constant current with a current density of ^{10 mA / cm 2 was further measured as the device life (hr).}

The quantum efficiency of the light emitting element includes the internal quantum efficiency and the external quantum efficiency. In the internal quantum efficiency, the external energy injected as electrons (or holes) into the light emitting layer of the light emitting element is converted into pure photons. The ratio is shown. On the other hand, the external quantum efficiency is calculated based on the amount of these photons emitted to the outside of the light emitting element, and a part of the photons generated in the light emitting layer is continuously absorbed or reflected inside the light emitting element. Therefore, the external quantum efficiency is lower than the internal quantum efficiency because it is not emitted to the outside of the light emitting element.

The method for measuring the external quantum efficiency is as follows. A voltage / current generator R6144 manufactured by Advantest Co., Ltd. was used ^{to apply a voltage at which the brightness of the element became 1000 cd / m 2} to cause the element to emit light. The spectral radiance in the visible light region was measured from the direction perpendicular to the light emitting surface using a spectral radiance meter SR-3AR manufactured by TOPCON. Assuming that the light emitting surface is a completely diffused surface, the value obtained by dividing the measured spectral radiance value of each wavelength component by the wavelength energy and multiplying by π is the number of photons at each wavelength. Next, the number of photons was integrated over the entire observed wavelength region to obtain the total number of photons emitted from the device. The value obtained by dividing the applied current value by the elementary charge is the number of carriers injected into the device, and the value obtained by dividing the total number of photons emitted from the device by the number of carriers injected into the device is the external quantum efficiency.

Table 2 below shows the material composition and EL characteristic data of each layer in the organic EL device according to Examples 1 to 17, Reference Example 1 and Comparative Example 1 produced.

Table 3 below shows the material composition and EL characteristic data of each layer in the produced organic EL devices according to Examples 18 to 25 and Reference Example 2.

Table 4 below shows the material composition and EL characteristic data of each layer in the produced organic EL devices according to Examples 26 to 44 and Comparative Example 2.

Table 5 below shows the material composition and EL characteristic data of each layer in the produced organic EL devices according to Examples 45 to 60, Reference Example 3 and Comparative Example 3.

Table 6 below shows the material composition and EL characteristic data of each layer in the produced organic EL devices according to Examples 61 to 78, Reference Example 4 and Comparative Example 4.

Table 7 below shows the material composition and EL characteristic data of each layer of the produced organic EL devices according to Examples 79 to 103, Comparative Examples 5 to 6, and Reference Example 5.

Table 8 below shows the material composition of each layer and the EL characteristic data of the organic EL devices according to the prepared Examples 104 to 134, Reference Examples 6 to 7, and Comparative Example 7.

Table 9 below shows the material composition and EL characteristic data of each layer in the organic EL device according to Examples 135 to 141, Reference Example 8 and Comparative Example 8 produced.

Table 10 below shows the material composition and EL characteristic data of each layer in the produced organic EL devices according to Examples 142 to 154, Reference Example 9 and Comparative Example 9.

Table 11 below shows the material composition and EL characteristic data of each layer in the organic EL device according to the prepared Examples 155 to 165, Reference Example 10 and Comparative Example 10.

In each of the above tables, "HI" is N ⁴ , N ^4' -diphenyl-N ⁴ , N ^4' -bis (9-phenyl-9H-carbazole-3-yl)-[1,1'-biphenyl] -4. , 4'-diamine, "HAT-CN" is 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile, "HT-1" is N- ([1,1'- Biphenyl] -4-yl) -9,9-dimethyl-N- (4- (9-phenyl-9H-carbazole-3-yl) phenyl) -9H-fluoren-2-amine, "HT-2" Is N, N-bis (4- (dibenzo [b, d] furan-4-yl) phenyl)-[1,1': 4', 1 "-terphenyl] -4-amine, which is" ET- "1" is 4,6,8,10-tetraphenyl [1,4] benzoxabolinino [2,3,4-kl] phenoxabolinine, and "ET-2" is 3,3'-(((() 2-Phenylanthracene-9,10-diyl) bis (4,1-phenylene)) bis (4-methylpyridine), "ET-3" is 9-([1,4] benzoxabolinino [2] , 3,4-kl] phenoxabolinin-7-yl) -9H-carbazole, and "ET-4" is 9- [4-([1,4] benzoxabolinino [2,3,4-] kl] phenoxabolinin-7-yl) phenyl] -9H-carbazole. The chemical structure is shown below together with "Liq".

<Example 1>
<Host material: compound (1-47), dopant material: compound (2-41) element>
A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Opto Science, Inc.) obtained by polishing ITO formed to a thickness of 180 nm by sputtering to 150 nm was used as a transparent support substrate. This transparent support substrate is fixed to a substrate holder of a commercially available thin film deposition apparatus (manufactured by Choshu Industry Co., Ltd.), and HI, HAT-CN, HT-1, HT-2, compound (1-47), compound (2-41). ), ET-1 and ET-2, respectively, and an aluminum nitride vapor deposition boat containing Liq, magnesium, and silver, respectively.

As shown in Table 2, the following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is ^{depressurized to 5 × 10 -4} Pa, and HI, HAT-CN, HT-1 and HT-2 are vapor-deposited in this order, and the hole injection layer 1 (thickness 40 nm) and the hole injection layer 2 (film) are deposited. A hole transport layer 1 (thickness 15 nm) and a hole transport layer 2 (thickness 10 nm) were formed (thickness 5 nm). Next, the compound (1-47) and the compound (2-41) were simultaneously heated and vapor-deposited to a film thickness of 25 nm to form a light emitting layer. The deposition rate was adjusted so that the mass ratio of compound (1-47) to compound (2-41) was approximately 98: 2. Next, ET-1 was heated and vapor-deposited to a film thickness of 5 nm to form an electron transport layer 1. Next, ET-2 and Liq were heated at the same time and vapor-deposited to a film thickness of 25 nm to form an electron transport layer 2. The deposition rate was adjusted so that the mass ratio of ET-2 and Liq was approximately 50:50. The deposition rate of each layer was 0.01 to 1 nm / sec. Then, Liq is heated and vapor-deposited at a vapor deposition rate of 0.01 to 0.1 nm / sec so as to have a film thickness of 1 nm, and then magnesium and silver are simultaneously heated and vapor-deposited so as to have a film thickness of 100 nm. A cathode was formed to obtain an organic EL device. At this time, the vapor deposition rate was adjusted between 0.1 and 10 nm / sec so that the atomic number ratio of magnesium and silver was 10: 1.

A DC voltage was applied with the ITO electrode as the anode and the magnesium / silver electrode as the cathode, and ^{the characteristics at the time of 1000 cd / m 2} emission were measured. As shown in Table 3, the drive voltage was 4.11 V and the external quantum efficiency was 6. A blue emission with a wavelength of .32% and a wavelength of 461 nm was obtained.

<Examples 2 to 17>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 2, and EL characteristic data was measured (Table 2).

<Reference example 1>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 2, and EL characteristic data was measured (Table 2).

<Comparative example 1>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 2, and EL characteristic data was measured (Table 2).

<Examples 18 to 25>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 3, and EL characteristic data was measured (Table 3).

<Reference example 2>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 3, and EL characteristic data was measured (Table 3).

<Examples 26 to 44>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 4, and EL characteristic data was measured (Table 4).

<Comparative example 2>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 4, and EL characteristic data was measured (Table 4).

<Examples 45 to 60>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 5, and EL characteristic data was measured (Table 5).

<Reference example 3>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 5, and EL characteristic data was measured (Table 5).

<Comparative example 3>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 5, and EL characteristic data was measured (Table 5).

<Examples 60 to 78>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 6, and EL characteristic data was measured (Table 6).

<Reference example 4>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 6, and EL characteristic data was measured (Table 6).

<Comparative example 4>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 6, and EL characteristic data was measured (Table 6).

<Examples 79 to 103>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 7, and EL characteristic data was measured (Table 7).

<Reference example 5>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 7, and EL characteristic data was measured (Table 7).

<Comparative Examples 5 to 6>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 7, and EL characteristic data was measured (Table 7).

<Examples 104 to 134>
Each organic EL element was manufactured with the layer structure shown in Table 8 according to Example 1, and the EL characteristic data was measured (Table 8).

<Reference Examples 6 to 7>
Each organic EL element was manufactured with the layer structure shown in Table 8 according to Example 1, and the EL characteristic data was measured (Table 8).

<Comparative Example 7>
Each organic EL element was manufactured with the layer structure shown in Table 8 according to Example 1, and the EL characteristic data was measured (Table 8).

<Examples 135-141>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 9, and EL characteristic data was measured (Table 9).

<Reference example 8>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 9, and EL characteristic data was measured (Table 9).

<Comparative Example 8>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 9, and EL characteristic data was measured (Table 9).

<Examples 142 to 154>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 10, and EL characteristic data was measured (Table 10).

<Reference example 9>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 10, and EL characteristic data was measured (Table 10).

<Comparative Example 9>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 10, and EL characteristic data was measured (Table 10).

<Examples 155 to 165>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 11, and EL characteristic data was measured (Table 11).

<Reference example 10>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 11, and EL characteristic data was measured (Table 11).

<Comparative Example 10>
According to Example 1, each organic EL element was manufactured with the layer structure shown in Table 11, and EL characteristic data was measured (Table 11).

INDUSTRIAL APPLICABILITY The present invention provides an organic EL device having high external quantum efficiency and capable of emitting light at a low voltage.

100 Organic electroluminescent device 101 Substrate 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light emitting layer 106 Electron transport layer 107 Electron injection layer 108 Cathode

Claims (27)

An organic electroluminescent element having a pair of electrodes composed of an anode and a cathode and a light emitting layer arranged between the pair of electrodes. The light emitting layer is an anthracene represented by the following formula (1) as a host material. An organic electroluminescent element containing a multimer of a polycyclic aromatic compound represented by the following formula (2) or a polycyclic aromatic compound having a plurality of structures represented by the following formula (2) as a system compound and a dopant material. ..

(In equation (1),
Ar ^c is a heteroaryl optionally are also aryl or substituted optionally be substituted,
R ^c is hydrogen, alkyl, or cycloalkyl,
Ar ¹¹ , Ar ¹² , Ar ¹³ , Ar ¹⁴ , Ar ¹⁵ , Ar ¹⁶ , Ar ¹⁷ , and Ar ¹⁸ are independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, respectively. Diarylamino which may be substituted, diheteroarylamino which may be substituted, arylheteroarylamino which may be substituted, alkyl which may be substituted, cycloalkyl which may be substituted, cycloalkyl which may be substituted, An alkenyl which may be substituted, an alkoxy which may be substituted, an aryloxy which may be substituted, an arylthio which may be substituted, or a silyl which may be substituted.
At least one hydrogen in the compound represented by the formula (1) may be substituted with halogen, cyano, or deuterium. )
(In equation (2),
Rings A, B, and C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted.
X ¹ and X ² are independently>O,>N-R,> C (-R) ₂ ,> S, or> Se, even if the R of> N-R is substituted. A good aryl, a heteroaryl which may be substituted, an alkyl which may be substituted, or a cycloalkyl which may be substituted, and the R of> C (-R) ₂ is hydrogen, even if it is substituted. A good aryl, an alkyl which may be substituted, or a cycloalkyl which may be substituted, and the R of> N-R and / or the R of> C (-R) ₂ may be a linking group or a simple substance. It may be bonded to the A ring, the B ring, and / or the C ring by the bond.
At least one of the aryl ring and the heteroaryl ring in the compound represented by the formula (2) or a multimer thereof may be condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane is substituted. At least one −CH ₂ − in the cycloalkane may be substituted with −O−.
At least one hydrogen in the compound or structure represented by the formula (2) may be substituted with deuterium, cyano, or halogen. ) The polycyclic aromatic compound represented by the formula (2) or the multimer of the polycyclic aromatic compound having a plurality of structures represented by the formula (2) is represented by the formulas (2-a), the formula (2-b), and the like. A polycyclic aromatic compound represented by the formula (2-c), the formula (2-d), the formula (2-e), or the formula (2-f) or the formula (2-a), the formula (2-b). ), Formula (2-c), formula (2-d), formula (2-e), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the formula (2-f). Item 2. The organic electric field light emitting element;

In formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f),
R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , and R ¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, respectively. Diheteroarylamino, arylheteroarylamino, diallylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyls, which are these. At least one hydrogen in is optionally substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R. ^{Adjacent groups of 8} , R ⁹ , R ¹⁰ , and R ¹¹ may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, b ring, or c ring, and the formed ring may be formed. At least one hydrogen in is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, and. It may be substituted with cycloalkyl, alkoxy, aryloxy, or substituted silyls, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyls.
X _X is independently,>O,> S, a> N-R or> C _{(-R) 2,,} wherein> N-R of R is optionally substituted aryl, optionally substituted It may be heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and the R of> C (-R) ₂ may be independently hydrogen, alkyl or cyclo, respectively. Aryl, alkyl or cycloalkyl, optionally substituted, heteroaryl, alkyl, or cycloalkyl, which may be substituted with alkyl.
X ¹ and X ² are independently>O,>N-R,> C (-R) ₂ ,> S, or> Se, and the R of> N-R has 1 to 1 carbon atoms. It may be substituted with an alkyl of 6 or a cycloalkyl having 3 to 14 carbon atoms, an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms. Heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, and R of> C (-R) ₂ is hydrogen, alkyl having 1 to 6 carbon atoms. Alternatively, it may be substituted with a cycloalkyl having 3 to 14 carbon atoms, an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and the above-mentioned> N- R of R and / or R of> C (-R) ₂ is -O-, -S-, -C (-R) _2- , or the a ring, b ring, and / or c ring by a single bond. The -C (-R) _2- R may be independently an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms.
A compound represented by the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e), or the formula (2-f) or a large amount thereof. At least one of the aryl and heteroaryl rings in the body may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one in the cycloalkane. One −CH ₂₋ may be replaced by −O−
In a compound or structure represented by the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e), or the formula (2-f). At least one hydrogen may be substituted with deuterium, cyano, or halogen.
In the case of a trimer, the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e), or the formula (2-f) It is a dimer or trimer having 2 or 3 structures represented. The compound represented by the formula (2) is represented by a polycyclic aromatic compound represented by the formula (2-a) or the formula (2-b) or the formula (2-a) or the formula (2-b). The organic electroluminescent element according to claim 2, which is a multimer of a polycyclic aromatic compound having a plurality of such structures. The organic electroluminescent device according to claim 3, wherein the compound represented by the formula (2) is any of the compounds represented by the following formula;

In the above formula, Me is methyl, tBu is t-butyl, tAm is t-amyl, and D is deuterium. In formula (1), any two of Ar ¹¹ , Ar ¹² , Ar ¹³ , Ar ¹⁴ , Ar ¹⁵ , Ar ¹⁶ , Ar ¹⁷ , and Ar ¹⁸ may be substituted or substituted aryl or heteroaryl which may be substituted. The other six are hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, or optionally substituted alkoxy. The organic electric field light emitting element according to any one of the above items. The anthracene-based compound represented by the formula (1) is the anthracene-based compound represented by the following formulas (1A), (1B), (1C), (1D), or (1E), according to claim 5. Organic electroluminescent device;

In formula (1A), (1B), (1C), (1D) or (1E),
^{Ar c ', Ar 11',} Ar 12 ', Ar 13', Ar 14 ', Ar 15', Ar 17 ', and ^{Ar 18'} each independently phenyl, biphenylyl, terphenylyl, quaterphenylene phenylene Lil, naphthyl, A group represented by phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or formula (A), and at least one hydrogen in these groups is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl. , Phenyltril, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by the formula (A), wherein the two hydrogens of methylene in fluorenyl and benzofluorenyl are here. When both are substituted with phenyls, these phenyls may be single bonded to each other.
^{Ar c ', Ar 11',} Ar 12 ', Ar 13', Ar 14 ', Ar 15', Ar 17 ', or ^{Ar 18'} is a carbon atom on the anthracene ring which is not bound methyl instead of hydrogen Alternatively, t-butyl may be bonded,
At least one hydrogen in the compound represented by the formulas (1A), (1B), (1C), (1D) or (1E) may be halogen, cyano, or deuterium substituted.
The group represented by the formula (A) is a group obtained by removing one hydrogen at any position of the formula (A), and * indicates the position.
In formula (A), Y is -O-, -S- or> N-R ³⁹ , and R ^{21 to} R ²⁸ are independently hydrogen, optionally substituted alkyl, optionally substituted, respectively. Cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tri. Cycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano, the ^{adjacent groups of R 21-} R ²⁸ are bonded to each other to form a hydrocarbon ring. An aryl ring or a heteroaryl ring may be formed, and at least one hydrogen in the formed hydrocarbon ring, aryl ring or heteroaryl ring may be an alkyl substituted or a cycloalkyl substituted. , Aryl which may be substituted, heteroaryl which may be substituted, alkoxy which may be substituted, aryloxy which may be substituted, arylthio which may be substituted, trialkylsilyl, tricycloalkyl. It may be substituted with silyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy, or cyano, and R ³⁹ is hydrogen or optionally substituted aryl. The group represented by the formula (A) is a group represented by any of the formulas (A-1) to (A-14).
The groups represented by the formulas (A-1) to (A-14) are groups obtained by removing one hydrogen at any position of the formulas (A-1) to (A-14). And * indicates the position,
In formulas (A-1) to (A-14), Y is -O-, -S-, or> N-R ³⁹ , R ³⁹ is hydrogen or aryl, and formulas (A-1) to-. At least one hydrogen in the group represented by the formula (A-14) is alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyl. It may be substituted with dicycloalkylsilyl, diaryl substituted amino, diheteroaryl substituted amino, aryl heteroaryl substituted amino, halogen, hydroxy, or cyano,
The organic electroluminescent device according to claim 6.

^{Ar c ', Ar 11',} Ar 12 ', Ar 13', Ar 14 ', Ar 15', Ar 17 ', and ^{Ar 18'} each phenyl independently is biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl or, It is a group represented by any of formulas (A-1) to (A-4), and at least one hydrogen in these groups is phenyl, biphenylyl, naphthyl, phenanthryl, fluorenyl, or formula (A-1). ) To a group represented by any of the formulas (A-4).
At least one hydrogen in the compound represented by the formulas (1A), (1B), (1C), (1D) or (1E) may be substituted with halogen, cyano, or deuterium.
The organic electroluminescent device according to claim 6 or 7. Ar ¹⁴ and Ar ¹⁵ are optionally substituted aryls or optionally substituted heteroaryls, and Ar ¹¹ , Ar ¹² , Ar ¹³ , Ar ¹⁶ , Ar ^17, and Ar ¹⁸ are all hydrogens, claim. Item 5. The organic electroluminescent device according to Item 5. The organic electroluminescent device according to claim 9, wherein at least one selected from the group consisting of Ar ^C , Ar ¹⁴ , and Ar ^{15 is a group containing an anthracene ring.} The organic electroluminescent device according to claim 9, wherein at least one selected from the group consisting of Ar ^C , Ar ¹⁴ , and Ar ^{15 contains a group represented by the formula (A');}

In formula (A'), R ^{21 to} R ²⁸ are independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted, respectively. Heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, substituted It may be amino, halogen, hydroxy or cyano, and ^{adjacent groups of R 21 to} R ²⁸ may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring, which may be formed. At least one hydrogen in a hydrocarbon ring, an aryl ring or a heteroaryl ring may be an alkyl optionally substituted, a cycloalkyl optionally substituted, an aryl optionally substituted, a heteroaryl optionally substituted. , Substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, substituted It may be substituted with amino, halogen, hydroxy, or cyano. The organic electroluminescent device according to claim 9, wherein at least one hydrogen in the compound represented by the formula (1) is replaced with deuterium. It has an electron transporting layer and / or an electron injecting layer arranged between the cathode and the light emitting layer, and at least one of the electron transporting layer and the electron injecting layer is a borane derivative, a pyridine derivative, a fluorentene derivative, or BO. From system derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzoimidazole derivatives, phenanthroline derivatives, quinolinol metal complexes, thiazole derivatives, benzothiazole derivatives, silol derivatives, and azoline derivatives The organic electric field light emitting element according to any one of claims 1 to 12, which contains at least one selected from the group. The electron transporting layer and / or electron injecting layer further comprises an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, and an alkaline earth metal. Claim that it contains at least one selected from the group consisting of halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes. 13. The organic electric field light emitting element according to 13. A display device comprising the organic electroluminescent device according to any one of claims 1 to 14. A lighting device comprising the organic electroluminescent device according to any one of claims 1 to 14. Anthracene-based compound represented by the following formula (1);

In equation (1),
Ar ^c is a heteroaryl optionally are also aryl or substituted optionally be substituted,
R ^c is hydrogen, alkyl, or cycloalkyl,
Ar ¹¹ , Ar ¹² , Ar ¹³ , Ar ¹⁴ , Ar ¹⁵ , Ar ¹⁶ , Ar ¹⁷ , and Ar ¹⁸ are independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, respectively. Diarylamino which may be substituted, diheteroarylamino which may be substituted, arylheteroarylamino which may be substituted, alkyl which may be substituted, cycloalkyl which may be substituted, cycloalkyl which may be substituted, An alkenyl which may be substituted, an alkoxy which may be substituted, an aryloxy which may be substituted, an arylthio which may be substituted, or a silyl which may be substituted.
At least one hydrogen in the compound represented by the formula (1) may be substituted with halogen, cyano, or deuterium. The anthracene-based compound according to claim 17, which is represented by the following formula (1Aa);

Wherein ^{(1Aa), Ar c ',} Ar 14', and ^{Ar 15} 'are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or formula, ( It is a group represented by any of A-1) to the formula (A-14), and at least one hydrogen in these groups is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzo. It may be substituted with fluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any of formulas (A-1) to (A-14), wherein in fluorenyl and benzofluorenyl. when the hydrogen of the methylene is substituted with either a phenyl, these phenyl may be attached by a single bond to each ^{other, Ar c ', Ar 14'} , or Ar 15 ^'is unbound on anthracene ring Methyl or t-butyl may be bonded to the carbon atom of the above instead of hydrogen.
At least one hydrogen in the compound represented by the formula (1Aa) may be substituted with halogen, cyano, or deuterium.
The groups represented by the formulas (A-1) to (A-14) are groups obtained by removing one hydrogen at any position of the formulas (A-1) to (A-14). And * indicates the position,
In formulas (A-1) to (A-14), Y is -O-, -S-, or> N-R ³⁹ , R ³⁹ is hydrogen or aryl, and formulas (A-1) to-. At least one hydrogen in the group represented by the formula (A-14) is alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyl. It may be substituted with dicycloalkylsilyl, diaryl substituted amino, diheteroaryl substituted amino, aryl heteroaryl substituted amino, halogen, hydroxy, or cyano.
However, at least one hydrogen in the compound represented by the formula (1Aa) may be substituted with halogen or cyano, and at least one hydrogen in the compound represented by the formula (1Aa) is substituted with deuterium. .. ^{Ar c ',} Ar ^14' and ^{Ar 15} 'are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl or formula (A-1) a group represented by any one of the - formula (A-4), And at least one hydrogen in these groups may be substituted with phenyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any of formulas (A-1) to (A-4). , The anthracene-based compound according to claim 18. The anthracene-based compound according to claim 18 or 19, wherein at least the hydrogen bonded to the 10-position of the anthracene ring is replaced with deuterium in the formula (1Aa). The anthracene-based compound according to claim 18, which is represented by any of the following formulas.

(In the above formula, D represents deuterium.) The anthracene-based compound according to claim 17, which is represented by any of the following formulas.

(In the above formula, D represents deuterium.) The anthracene-based compound according to claim 17, which is represented by any of the following formulas.

The anthracene-based compound according to claim 17, which is represented by any of the following formulas.

(In the above formula, D represents deuterium.) The anthracene-based compound according to claim 17, which is represented by any of the following formulas.

(In the above formula, D represents deuterium.) The anthracene-based compound according to claim 17, which is represented by any of the following formulas.

(In the above formula, Me is methyl, tBu is t-butyl, and CyHex is cyclohexyl.) The anthracene-based compound according to claim 17, which is represented by any of the following formulas.

(In the above formula, D represents deuterium.)

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